US3087936A - Reaction product of an aliphatic olefinpolymer-succinic acid producing compound with an amine and reacting the resulting product with a boron compound - Google Patents
Reaction product of an aliphatic olefinpolymer-succinic acid producing compound with an amine and reacting the resulting product with a boron compound Download PDFInfo
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- US3087936A US3087936A US132305A US13230561A US3087936A US 3087936 A US3087936 A US 3087936A US 132305 A US132305 A US 132305A US 13230561 A US13230561 A US 13230561A US 3087936 A US3087936 A US 3087936A
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- nitrogen
- boron
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/72—Nitrogen atoms
- C07D213/75—Amino or imino radicals, acylated by carboxylic or carbonic acids, or by sulfur or nitrogen analogues thereof, e.g. carbamates
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C243/00—Compounds containing chains of nitrogen atoms singly-bound to each other, e.g. hydrazines, triazanes
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/16—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms
- C07D295/18—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms by radicals derived from carboxylic acids, or sulfur or nitrogen analogues thereof
- C07D295/182—Radicals derived from carboxylic acids
- C07D295/185—Radicals derived from carboxylic acids from aliphatic carboxylic acids
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- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic System
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic System
- C07F5/02—Boron compounds
- C07F5/022—Boron compounds without C-boron linkages
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F8/00—Chemical modification by after-treatment
- C08F8/30—Introducing nitrogen atoms or nitrogen-containing groups
- C08F8/32—Introducing nitrogen atoms or nitrogen-containing groups by reaction with amines
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- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M133/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing nitrogen
- C10M133/52—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing nitrogen having a carbon chain of 30 or more atoms
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- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
- C10M2207/02—Hydroxy compounds
- C10M2207/023—Hydroxy compounds having hydroxy groups bound to carbon atoms of six-membered aromatic rings
- C10M2207/026—Hydroxy compounds having hydroxy groups bound to carbon atoms of six-membered aromatic rings with tertiary alkyl groups
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- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
- C10M2207/02—Hydroxy compounds
- C10M2207/023—Hydroxy compounds having hydroxy groups bound to carbon atoms of six-membered aromatic rings
- C10M2207/027—Neutral salts thereof
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- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
- C10M2207/28—Esters
- C10M2207/282—Esters of (cyclo)aliphatic oolycarboxylic acids
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- C10M2207/34—Esters having a hydrocarbon substituent of thirty or more carbon atoms, e.g. substituted succinic acid derivatives
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- C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
- C10M2215/02—Amines, e.g. polyalkylene polyamines; Quaternary amines
- C10M2215/04—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to acyclic or cycloaliphatic carbon atoms
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- C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
- C10M2215/26—Amines
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- C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
- C10M2219/02—Sulfur-containing compounds obtained by sulfurisation with sulfur or sulfur-containing compounds
- C10M2219/022—Sulfur-containing compounds obtained by sulfurisation with sulfur or sulfur-containing compounds of hydrocarbons, e.g. olefines
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- C10M2219/04—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions containing sulfur-to-oxygen bonds, i.e. sulfones, sulfoxides
- C10M2219/044—Sulfonic acids, Derivatives thereof, e.g. neutral salts
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- C10M2219/06—Thio-acids; Thiocyanates; Derivatives thereof
- C10M2219/062—Thio-acids; Thiocyanates; Derivatives thereof having carbon-to-sulfur double bonds
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Definitions
- This invention relates to oil-soluble nitrogenand boroncontaining compositions and to the process of preparing the same.
- the compositions of this invention are useful as additives in lubricants, especially lubricants intended for use in internal combustion engines, gears, and power transmitting units.
- compositions which are adapted for use as additives in hydrocarbon oils.
- compositions which are effective as detergents in lubricating compositions are also an object of this invention to provide compositions which are effective as detergents in lubricating compositions.
- a process for preparing oil-soluble nitrogenand boron-containing compositions comprising treating an acylated nitrogen composition characterized by the presence within its structure of (A) a substatnially hydrocar-substituted suc-cinic radical selected from the class consisting of succinoyl, succinimidoyl, and succinoyloxy radicals wherein the substantially hydrocarbon substituent contains at least about 50 aliphatic carbon atoms and (B) a nitrogen-containing group characterized by a nitrogen atom attached directly to said succinic radical, with a boron compound selected from the class consisting of boron oxide, boron halides, boron acids, and esters of boron acids in an amount to provide from about 0.1 atomic proportion of boron for each mole of said acylated nitrogen composition to about 10 atomic proportions of boron for each atomic proportion of nitrogen of said acylated nitrogen composition.
- the substantially hydrocarbon substituent of the acylated nitrogen composition may contain polar groups provided, however, that the polar groups are not present in proportions sufliciently large to alter significantly the hydrocarbon character of the substituent.
- the polar groups are exemplified by chlor-o, bromo, keto, ethereal, aldehydo, and nitro, etc.
- the upper limit with respect to the proportion of such polar groups in the substituent is ap proximately 10% based on the Weight of the hydrocarbon portion of the substituent.
- the sources of the substantially hydrocarbon substituent include principally the high molecular weight substantially saturated petroleum fractions and substantially saturated olefin polymers, particularly polymers of monoolefins having from 2 to 30 carbon atoms.
- the especially useful polymers are the polymers of l-monoclefins such as ethylene, propene, 1-butene, isobutene, l-hexene, l-octene, Z-methyl-l-heptene, 3-cvcloheXyl-1-butene, and Z-methyl-S-propyl-l-hexene.
- Polymers of medial olefins i.e., olefins in which the olefinic linkage is not at the terminal position, likewise are useful. They are illustrated by Z-butene, 3-penetne, and 4-octene.
- interpolymers of the olefins such as those illustrated above with other interpolymerizable olefinlc substances such as aromatic olefins, cyclic olefins, and polyolefins.
- Such interpolymers include, for example, those prepared by polymerizing isobutene with styrene; isobutene with butadiene; propene with isoprene; ethylene with piperylene; isobutene with chloroprene; isobutene with p-methyl styrene; l-heXene with 1,3-hexadiene; 1 octene with l-hexene; 1 heptene with l-pentene;
- the relative proportions of the mono-olefins to the other monomers in the interpolymers influence the stability and oil-solubility of the final products derived from such interpolymers.
- the interpolymers contemplated for use in this invention should be substantially aliphatic and substantially saturated, i.e., they should contain at least about 80%, preferably at least about 95%, on a weight basis of units derived from the aliphatic monoolefins and no more than about of olefinic linkages based on the total number of carbon-to-carbon covalent linkages. In most instances, the percentage of olefinic linkages should be less than about 2% of the total number of carbon-to-carbon covalent linkages.
- interpolymers include copolymer of 95% (by weight) of isobutene with 5% of styrene; terpolymer of 98% of isobutene with 1% of piperylene and 1% of chloroprene; terpolyrner of 95% ofisobutene with 2% of l-butene and 3% of l-hexene; terpolymer of 80% of isobutene with 20% of l-pentene and 20% of l-octene; copolymer of 80% of l-hexene and 20% of l-heptene; terpolymer of 90% of isobutene with 2% of cyclohexene and 8% of propene; and copolymer of 80% of ethylene and 20% of propene.
- Another source of the substantially hydrocarbon radical comprises saturated aliphatic hydrocarbons such as highly refined high molecular weight white oils or synthetic alkanes such as are obtained by hydrogenation of 'high molecular Weight olefin polymers illustrated above or high molecular weight olefinic substances.
- olefin polymers having molecular weight of about 750-6000 are preferred.
- Higher molecular weight olefin polymers having molecular weights from about 10,000 to about 100,000 or higher have been found to impart also viscosity index improving properties to the final products of this invention.
- the use of such higher molecular weight olefin polymers often is desirable.
- the nitrogen-containing group of the acylated nitrogen compositions of this invention is derived from compounds characterized by a radical having the structural configuration
- the two remaining valences of the nitrogen atom of the above radical preferably are satisfied by hydrogen, amino, or organic radicals bonded to said nitrogen atom through direct carbon-to-nitrogen linkages.
- the compounds from which the nitrogen-containing group may be derived include principally ammonia, aliphatic amines, aromatic amines, heterocyclic amines, or carbocyclic amines.
- the amines may be primary or secondary amines and may also be polyarnines such as alkylene amines, arylene amines, cyclic polyamines, and the hydroxy-substituted derivatives of such polyamines.
- amines of these types are methylamine, N-methylethylamine, N-methyl-octylamine, N-cyclohexyl-aniline, dibutylamine, cyclohexylamine, aniline, di(p -rnethyl phenyl)amine, dodecylamine, octadecylamine, o-phenylenediamine, N,N' di n butyl p phenylenediamine, morpholine, piperazine, tetrahydropyrazine, indole, hexahydro-1,3,5-triazine, 1-H-1,2,4-triazole, melamine, bis- (p-aminophenyl)methane, phenyl-methylenimine, menthanediamine, cyclohexamine, pyrrolidine, 3-amino-5,6- diphenyl 1,2,4 triazine, ethanolamine, diethanolamine,
- A is a substantially hydrocarbon or hydrogen radical, and the alkylene radical is preferably a loWer alkylene radical having less than about 8 carbon atoms.
- the alkylene amines include principally methylene amines, ethylene amines, butylene amines, propylene amines, pentylene amines, hexylene amines, heptylene amines, octylene amines, other polymethylene amines, and also the cyclic and the higher homologs of such amines such as pipe-razines and amino alkyl substituted piperazines.
- ethylene diamine triethylene tetramine, propylene diamine, decamethylene diamine, octamethylene diamine, di(heptamethylene)triamine, tripropylene tetramine, tetraethylene pentamine, trimethylene diamine, pentaethylene hexamine, di(trimethylene) triamine, 2 heptyl 3 (2 aminopropyl) imidazoline, 4 methylimidazoline, 1,3 bis(2 aminoethyl).imidazoline, pyrimidine, 1-(Z-aminopropyl)piperazine, 1,4-bis(2-aminoetl1yl) piperazine, and Z-methyl-l- (Z-aminobutyl)piperazine. Higher homologues such as are obtained by condensing two or more of the aboveillustrated alkylene amines likewise are useful.
- the ethylene amines are especially useful. They are described in some detail under the heading Ethylene Amines in Encyclopedia of Chemical Technology, Kirk and Othmer, volume 5, pages 898905, Interscieuce Publishers, New York (1950). Such compounds are prepared most conveniently by the reaction of an alkylene chloride with ammonia. The reaction results in the production of somewhat complex mixtures of alkylene amines, including cyclic condensation products such as piperazines. These mixtures find use in the process of this invention. On the other hand, quite satisfactory products may be obtained also by the use of pure alkylene amines. An especially useful alkylene amine for reasons of economy as well as effectiveness of the prodthat of tetraethylene pentamine.
- Hydroxyalky -substituted alkylene amines i.e., alkylene amines having one or more hydroxyalkyl substituents on the nitrogen atoms, likewise are contemplated for use herein.
- the hydroxyalkyl-substituted alkylene amines are preferably those in which the alkyl rgoup is a lower alkyl group, i.e., having less than about 6 carbon atoms.
- Examples of such amines include N-(Z-hydroxyethyl) ethylene diamine, N,N bis(2 hydroxyethyl)ethylene diamine, 1 (2 hydroxyethyl)piperazine, mono -.hy droxypropyl substituted diethylene triamine, 1,4 bis(2- hydroxypropyl)piperazine, di-hydroxypropyl-substituted tetraethylene pentamine, N-(3-hydroxypropyl)tetramethylene diamine, and Z-heptadecyl-1-(2-hydroxyethyl) imidazoline.
- hydrazine phenylhyrazine, N,N'-diphenylhydrazine, octadecylhydrazine, benzoylhydrazine, urea, thiourea, N-butylurea, stearylamide, oleylamide, guanidine, 1,3 diphenylguanidine,
- 1,2,3 tributylguanidine 1,2,3 tributylguanidine, benzamidine, octadecamidine, N,N'-dimethylstearamidine, cyanarnide, dicyandiamide, guanylurea aminoguanidine, etc.
- the nitrogen-containing group in the acylated nitrogen compositions of this invention is characterized by a nitrogen atom attached directly to the scuccinic radical.
- the linkage between a nitrogen atom and a succinoyl radical is representative of an amide or an imide structure
- the linkage between a nitrogen atom and a succinirnidoyl radical is representative of an arnidine structure
- the linkage between a nitrogen atom and a succinoyloxy radical is representative of an ammoniumcarboxylic acid salt structure.
- the acylated nitrogen compositions of this invention are characterized by amide, amide-salt, imide, amidine, or salt linkages and in many instances a mixture of such linkages.
- a convenient method for preparing the acylated nitrogen compositions comprises reacting a high molecular weight succinic acid-producing compound characterized by the presence within its structure of a high molecular weight oil-solubilizing group having at lea-st about 50 aliphatic carbon atoms and at least one succinic acidproducing group.
- R is a subsantially hydrocarbon radical having at least about 50 aliphatic carbon atoms and X is selected from the class consisting of halogen, hydroxy, hydrocarbon-oxy, and acyloxy radicals, with a least about onehalf an equivalent amount of a nitrogen-containing compound characterized by the presence within its structure of at least one radical having the structural configuration
- the above process involves a reaction between the succinic acid-producing group with the nitrogen-containing radical to result in the direct attachment of the nitrogen atoms to the succinic radical, i.e., succinoyl, succinimidoyl, or succinolyloxy radical.
- the linkage formed between the nitrogen atom and the succinic radical may thus be that representative of a salt, amide, imide, or amidine radical.
- the product of the above process contains a mixture of linkages representative of such radicals.
- the precise relative proportions of such radicals in the product usually are not known as they depend to a large measure upon the type of the acid-producing group and the nitrogen-containing radical involved in the reaction and also upon the environment (e.g., temperature) in which the reaction is carried out.
- the reaction involving an acid or anhydride group with an amino nitrogen-containing radical at relatively low temperatures such as below about 60 C. results predominantly in a salt linkage l1 (i.e., C-ON) but at relatively high temperatures such as above about 80 C.
- the substantially saturated, aliphatic hydrcarbon-substituted succinic acids and anhydrides are especially preferred for use as the acid-producing reactant of this process for reasons of the particular elfectiveness of the products obtained from such compounds as additives in hydrocarbon oils.
- the succinic compounds are readily available from the reaction of maleic anhydride with a high molecular weight olefin or a chlorinated hydrocarbon such as the olefin polymer described hereinabove. The reaction involves merely heating the two reactants at a temperature about 100200 C.
- the product from such a reaction is an alkenyl succinic anhydride.
- the alkenyl group may be hydrogenater to an alkyl group.
- the anhydride may be hydrolyzed by treatment with water or steam to the corresponding acid. Either the anhydride or the acid may be converted to the corresponding acid halide or ester by reaction with, e.g., phosphorus halide, phenols, or alcohols.
- hydrocarbons containing an activating polar substituent i.e., a substituent which is capable of activating the hydrocarbon molecule in respect to reaction with maleic acid or anhydride, may be used in the above-illustrated reaction for preparing the succinic compounds.
- polar substituents may be illustrated by sulfide, disulfide, nitro, mercaptan, bromine, ketone, and aldehyde radicals.
- polar-substituted hydrocarbons examples include polypropene sulfide, di-polyisobutene disulfide, nitrated mineral oil, di-polyethylene sulfide, brominated polyethylene, etc.
- Another method useful for preparing the succinic acids and anhydrides involves the reaction of itaconic acid with a high molecular weight olefin or a polar-substituted hydrocarbon at a temperature usually within the range from about 100 C. to about 200 C.
- the acid halides of the succinic acids can be prepared by the reaction of the acids or their anhydrides with a halogenation agent such as phosphorus tri-bromide, phosphorus pentachloride or thionyl chloride.
- the esters of such acids can be prepared simply by the reaction of the acids or their anhydrides with an alcohol or a phenolic compound such as methanol, ethanol, octadecanol, cyclohexanol, phenol, naphthol, octylphenol, etc.
- the esteri-- fioation is usually promoted by the use of an alkaline catalyst such as sodium hydroxide or sodium alkoxide or an acidic catalyst such as sulfuric acid.
- the nature of the alcoholic or phenolic portion of the ester radical appears to have little influence on the utility of such ester as reactant in the process described hereinabove.
- the nitrogen-containing reactants useful in the above process are the compounds, described previously in this specification, from which the nitrogemcontaining group the acylated nitrogen compositions of this inven tion can be derived.
- the above process is usually carried out by heating a mixture of the acid-producing compound and the nitrogen-containing reactant at a temperature above C., preferably within the range from about C., to about 250 C.
- a temperature above C. preferably within the range from about C., to about 250 C.
- the process may be carried out at a lower temperature such as room temperature to obtain products having predominantly salt linkages or mixed salt-amide linkages.
- Such products may be converted, if desired, by heating to above 80 C. to products having predominantly amide, imide, or amidine linkages.
- a solvent such as benzene, toluene, naphtha, mineral oil, xylene, n-hexane, or the like is often desirable in the above process to facilitate the control of the reaction temperature.
- the relative proportions of the acid-producing compounds and the nitrogen-containing reactants to be used in the above process are such that at least about one-half of a stoichiometrically equivalent amount of the nitrogencontaining reactant is used for each equivalent of the acidproducing compound used.
- the equivalent weight of the nitrogen-containing reactant is based upon the number of the nitrogen-containing radicals.
- the equivalent weight of the acid-producing compound is based upon the number of the acid-producing radicals defined by the structural configuration ll -O-X
- ethylene diamine has two equivalents per mole; amino guanidine has four equivalents per mole; a suc-. cinic acid or ester has two equivalents per mole, etc.
- the upper limit of the useful amount of the nitrogencontaining reactant appears to be about two equivalents for each equivalent of the acid-producing compound used. Such amount is required, for instance, in the formation of products having predominantly amidine linkages. Beyond this limit, the excess amount of the nitrogen-containing reactant appears not to take part in the reaction and thus simply remains in the product apparently without any adverse effects.
- the lower limit of about one-half equivalent of the nitrogen-containing reactant used for each equivalent of the acid producing compound is based upon the stoichiometry for the formationof products having predominantly imide linkages. In most instances, the preferred amount of the nitrogen-containing reactant is approximately one equivalent for each equivalent of the acid-producing compound used.
- Example 1 A polyisobutenyl succinic anhydride is prepared by the reaction of a chlorinated polyisobutylene with maleic anhydride at 200 C.
- the polyisobutenyl radical has an average molecular weightof 850 and the resulting alkenyl succinic anhydride is found to have an acid number of 113 (corresponding to an equivalent weight of 500).
- the mixture then is heated and a Watertoluene azeotrope distilled from the mixture. When no more water would distill the mixture is heated to 150 C. at reduced pressure to remove the toluene. The residue is diluted with 350 grams of mineral oil and this solution is found to have a nitrogen content of 1.6%.
- Example 2 V The procedure of Example 1 is repeated using 31 grams (1 equivalent) of ethylene diamine as the amine reactant. The nitrogen content of the resulting product is 1.4%.
- Example 3 The procedure of Example 1 is repeated using 55.5 grams (1.5 equivalents) of an ethylene amine mixture having a composition corresponding to that of triethylene tetramine. The resulting product has a nitrogen content of 1.9%.
- Example 4 The procedure of Example 1 is repeated using 55.0
- the resulting product has a nitrogen Example 5 amine mixture having an average composition corresponding to that of tetraethylene pentamine.
- the mixture is heated to distill the water-toluene azeotrope and then to 150 C. at reduced pressure to remove the remaining toluene.
- the residual polyamide has a nitrogen content of 4.7%.
- Example 6 The procedure of Example 1 is repeated using 46 grams 1.5 equivalents) of ethylene diamine as the amine reactant. The product which resulted has a nitrogen content of 1.5%.
- Example 7 A polyisobutenyl succinic anhydride having an acid number of and an equivalent weight of 540 is prepared by the reaction of a chlorinated polyisobutylene (having an average molecular weight of 1,050 and a chlorine content of 4.3%) and maleic anhydride. To a mixture of 300 parts by weight of the polyisobutenyl succinic anhydride and 160 parts by weight of mineral oil there is added at 65-95 C. an equivalent amount (25 parts by weight) of the commercial ethylene amine mixture of-Example 5. This mixture then is heated to 150 C. to distill all of the Water formed in the reaction. Nitrogen is bubbled through the mixture at this temperature to insure removal of the last traces of water. The residue is diluted by 79 parts by weight of mineral oil and this oil solution found to have a nitrogen content of 1.6%.
- Example 8 A mixture of 2,112 grams (3.9 equivalents) of the polyisobutenyl succinic anhydride of-Example 7, 136 grams (3.9 equivalents) of diethylene triamine, and 1060 grams of mineral oil is heated at 140150 C. for one hour. Nitrogen is bubbled through the mixture at this temperature for four more hours to aid in the removal of water. The residue is diluted with 420 grams of min- .eral oil and this oil solution is found to have a nitrogen content of 1.3%
- Example 9 To a solution of 1,000 grams (1.87 equivalents) of the polyisobutenyl succinic anhydride of Example 7, in 500 grams of mineral oil there is added at 85-95 C. 70 grams (1.87 equivalents) of tetraethylene pentarnine. The mixture then is heated at -165 C. for four hours, blowing with nitrogen to aid in the removal of Water. The residue is diluted with 200 grams of mineral oil and the oil solution found to have a nitrogen content of 1.4%.
- Example 10 A polypropenyl succinic anhydride is prepared by the reaction of a chlorinated polypropylene (having a molecular weight of about 900 and a chlorine content of 4%) and maleic anhydride at 200 C. The product has an acid number of 75. To a mixture of 390 grams (0.52 equivalent) of this polypropenyl succinic anhydride, 500 grams of toluene, and grams of mineral oil there is added portionwise 22 grams (0.52 equivalent) the commercial ethylene amine mixture of Example 5. The reaction mixture is heated at reflux temperature for three hours and water removed from an azeotrope with toluene. The toluene then is removed by heating to 150 C./20 millimeters. The residue was found to contain 1.3% of nitrogen.
- Example 11 A substituted succinic anhydride is prepared by reacting maleic anhydride with a chlorinated copolymer of isobutylene and styrene.
- the copolymer consists of 94 parts by weight of isobutylene units and 6 parts by weight of the commercial ethylene amine mixture of Example 5.
- the mixture is heated at reflux temperature for three hours to remove by azeotropic distillation all of the water formed in the reaction, and then at 150 C./20 millimeters to remove the toluene.
- the residue contains 1.1% by weight of nitrogen.
- Example 12 A substituted succinic anhydride is prepared by reacting maleic anhydride with a chlorinated copolymer of isobutylene and isoprene.
- the copolymer consists of 99 parts by weight of isobutylene units and 1% by weight of isoprene units.
- the molecular Weight of the copolymer is 28,000 and the chlorine content of the chlorinated copolyrner is 1.95%.
- the resulting alkenyl succinic anhydride had an acid number of 54.
- Example 13 A polyisobutenyl succinic anhydride is prepared by the reaction of a chlorinated polyisobutylene with maleic anhydride.
- the chlorinated polyisobutylene has a chlorine content of 2% and an average molecular weight of 11,000.
- the polyisobutenyl succinic anhydride has an acid number of 48.
- a mixture of 410 grams (0.35 equivalent) of this anhydride, grams (0.35 equivalent) of the commercial ethylene amine mixture of Example 5 and 500 grams of toluene is heated at reflux temperature for four hours to remove water from an azeotrope with toluene. The toluene then is removed by heating to 150 C./ millimeters. The nitrogen content of the residue is 1.3%.
- Example 14 The procedure of Example 5 is repeated except that 0.94 equivalent of the amine is used instead of 1.55 equivalents.
- the nitrogen content of the product is 3%.
- Example 15 A polyisobutenyl-substituted succinic acid is prepared by hydrolysis of the corresponding anhydride (prepared in turn by the condensation of a chlorinated polyisobutylene and maleic anhydride). To 1152 grams (1.5 equivalents) of a 70% mineral oil solution of this polyisobutenyl succinic acid having an acid number of 62 there is added at room temperature 59.5 grams (1.5 equivalents) of the commercial ethylene amine mixture of Example 5. This mixture is heated at 150-167 C. for 7 hours during which time a total of 19.5 grams of water is distilled from the mixture. The residue is diluted with 174 grams of mineral oil and then filtered at 150 C. The filtrate has a nitrogen content of 1.6%.
- Example 16 A mixture of 1056 grams (2.0 equivalents) of the polyisobutenyl succinic anhydride of the preceding example (in which the polyisobutenyl group has a molecular Weight of 850), 89 grams (2.0 equivalents) of di-(1,2-propylene)- triamine (having a nitrogen content of 31.3%), 370 grams of mineral oil and 100 grams of toluene is heated at reflux temperature (180l90 C.) for 5 hours. A total of 18 grams of Water is collected from the water-toluene azeotrope. The residue is heated to 150 C./20 mm. to remove any last traces of water which might have remained. The nitrogen analysis of this residue is 1.9%.
- Example 17 A polyisobutylene having an average molecular Weight 10 of 50,000 is chlorinated to a chlorine content of 10% by weight. This chlorinated polyisobutylene is reacted with maleic anhydride to produce the corresponding polyisobutenyl succinic anhydride having an acid number of 24. To 6,000 grams (2.55 equivalents) of this anhydride there is added portionwise at 70105 C. 108 grams (2.55 equivalents) of the commercial ethylene amine mixture of Example 5 over a period of 45 minutes. The resulting mixture is heated for four hours at 160-180 C. While nitrogen is bubbled throughout to remove water. When all of the water has been removed the product is filtered and the filtrate found to have a nitrogen content of 0.6%
- Example 18 A mixture of 1 equivalent of a polyisobutene-substituted succinic anhydride having an acid number of 98 (prepared according to the procedure described in Example 1) and 1 equivalent of an acrolein-ammonia (molar ratio of 1:1) interpolymer having a nitrogen content of 23% by weight is diluted with 40% by its weight of a mineral oil. The resulting mixture is heated to 155 C. and nitrogen is bubbled through the mixture at this temperature for 5 hours. The residue is found to have a nitrogen content of 1.35%.
- Example 19 A cyanoethyl-substituted ethylene amine is prepared by mixing 212 grams of acrylonitrile with 216 grams of an ethylene amine mixture consisting of 75% by weight of triethylene tetramine and 25% by Weight of diethylene triamine at room temperature and heating the mixture at 110130 C. for 5 hours and then to C./30 mm. To a mixture of 1110 grams of the polyisobutene-substituted succinic anhydride of Example -1 and 825 grams of mineral oil there is added at 60 C. 143 grams dropwise of the above cyanoethyl-substituted ethylene amine (having a nitrogen content of 31.8%). The mixture is heated at 160 C. for 5 hours while being purged with nitrogen. A total of 6 cc. of water is removed by distillation. The residue has a nitrogen content of 1.66%.
- Example 20 To a mixture of 430 grams of the polyisobutene-substituted succinic anhydride of Example 1 and 355 grams of mineral oil there is added at 60-80 C. 108 grams of N-aminopropyl morpholine throughout a period of 1 hour. The mixture is heated at 150155 C. for 5 hours until no more distills. The residue is found to have a nitrogen content of 2.3%.
- Example 21 To a mixture of 430 grams of the polyisobutene-substituted succinic anhydride of Example 1 and 304 grams of mineral oil there is added at 60-80 C. 33 grams of dipropylene triamine. The mixture is then heated at 150 C. for 5 hours until no more water distills. The residue is found to have a nitrogen content of 1.45%.
- Example 22 To a mixture of 1000 grams of the polyisobutene-substituted succinic anhydride of Example 1 and 500 grams of mineral oil there is introduced at 150-160 C. beneath its surface a sufiicient quantity of ammonia for formation of an imide Within a period of 1 hour. The mixture is diluted with 169 grams of mineral oil, heated to 150 C. and filtered. The filtrate is found to have a nitrogen content of 0.77%.
- Example 23 A mixture of 286 grams of polyisobutene-substituted succinic anhydride of Example 1, 96 grams of N,N-dibu-tyl ethylene diamine and 252 grams of mineral oil is prepared at 60 C. and heated at 150l65 C. for 5 hours while being purged with nitrogen. The residue is found to have a nitrogen content of 2.24%.
- Example 24 A mixture of 41 7 grams of polyisobutene-substituted succinic anhydride of Example 1, 30 grams of N-(2- aminoethyl) trimethylene diamine and 293 grams of mineral oil is prepared at 60 -80 C. for 5 hours while being purged with nitrogen. The residue is found to have a nitrogen content of 1.51.
- Example 25 A mixture of 430 grams of the polyisobutene-substituted succinic anhydride of Example 1, 64 grams of 1,1- (dimethylaminoethyl)-4-methyl-piperazine and 324 grams of mineral oil is prepared at 60 C. and then heated at 150-155 C. while being blown with nitrogen. The residue is found to have a nitrogen content of 1.81%.
- Example 26 A mixture of 416 grams of polyisobutene-substituted succinic anhydride of Example 1, 124 grams of N-phenyl piperazine and 356 grams of mineral oil is prepared at 60 C. and then heated at ISO-155 C. for 5 hours while being purged with nitrogen. No water is removed by such heating. The residue is found to have a nitrogen content of 2.07%.
- Example 27 A mixture of 1110 grams of polyisobutene-substituted succinic anhydride of Example 1, 105 grams of anthranilic acid and 844 grams of mineral oil is heated at 100 C. for 2 hours. The mixture is cooled and is mixed with 72 grams of a mixture consisting of 75% by weight of triethylene tetramine and 25% by weight of diethylenetriamine at 6080 C. The resulting mixture is heated at 150-155 C. for 5 hours while being purged With nitrogen. The residue is found to have a nitrogen content of 1.72%.
- Example 28 A diisobutenyl-substituted ethylene amine is prepared by reacting 590 grams of diisobutenyl chloride and 264 grams of a mixture consisting of 75% by Weight of tri ethylene tetramine and 20% by Weight of diethylene triamine in the presence of 264 grams of potassium hydroxide (85% purity) and 2200 grams of isopropyl alcohol at 8590 C.
- a mixture of 528 grams of polyisobutene-substituted succinic anhydride of Example 1 101 grams of the above diisobutenyl-substituted ethylene amine and 411 grams of mineral oil is heated at 150- 160 C. while being purged with nitrogen until no more water distills. The residue has a nitrogen content of 1.98%.
- Example 29 A mixture of 45 grams of di-(polypropoxy)cocoamine having a molecular weight of 2265, 22 grams of polyisobutene-substituted succinic anhydride of Example 1 and 44 grams of mineral oil is heated at 150-155 C. for 7 hours. The residue is found to have a nitrogen content 'of 0.25%.
- Example 30 A mixture of 1000 grams of the polyisobutene-substituted succinic anhydride of Example 1, 159 grams of menthane diarnine and 5 00 grams of mineral oil is prepared at 70100 C. and heated at 150-490 C. while being blown with nitrogen until no water distills. The residue is diluted with 258 grams of mineral oil and the solution is found to have a nitrogen content of 1.32.
- Example 31 A polypropylene-substituted succinic anhydride having an acid number of 84 is prepared by the reaction of a chlorinated polypropylene having a chlorine content of 3% and molecular Weight of 1200 with maleic anhydride. A mixture of 813 grams of the polypropylene-substituted succinic anhydride, 50 grams of a commercial ethylene amine mixture having an average composition corre- 12 sponding to that of tetraethylene pentamine and 566 grams of mineral oil is heated at 150 C. for 5 hours. The residue is found to have a nitrogen content of 1.18%.
- Example 32 A mixture of 206 grams of N,N'-disecondary-buty1 p-phenylene diamine, 1000 grams of the polyisobutenesubstituted succinic anhydride of Example 1 and 500 grams of mineral oil is prepared at 85 C. and heated at 150-200 C. for 9.5 hours. The mixture is diluted with 290 grams of mineral oil, heated to 160 C. and filtered. The filtrate is found to have a nitrogen content of 1.29%.
- Example 33 ene pentamine at 70 80 C. The mixture is then heated at 150-160 C. While being purged with nitrogen until no more water is removed by distillation. The residue is diluted with 200 grams of mineral oil, heated to 160 C. and filtered. The filtrate has a nitrogen content of 1.16%.
- Example 34 To a solution of 1000 grams of the polyisobutene-substituted succinic anhydride of Example 1 in 500 grams of mineral oil there is added 28 grams of 1,1-dimethyl hydrazine at 5060 C. The mixture is heated at 6095 C. for 3 hours and then mixed with 40 grams of an ethylene amine mixture having an average composition corresponding to that of tetraethylene pentamine at 95 C. The mixture is then heated at 150-485 C. for 6 hours whereupon 14 grams of water is collected as the distillate. The residue is diluted with 197 grams of mineral oil, heated to 160 C. and filtered. The filtrate has a nitrogen content of 1.53%.
- Example 35 A mixture of 1000 grams of the polyisobutene-substituted succinic anhydride of Example 1, 333 grams of 1,2-di(3-aminopropoxy) ethane and 500 grams of mineral oil is heated at -170 C. for 5 hours whereupon 18 grams of water is collected as the distillate. The residue is diluted with 380 grams of mineral oil, heated to 160 C. and filtered. The filtrate has a nitrogen content of 2.3%.
- Example 36 A mixture of 1000 grams of the polyisobutene-substL tuted succinic anhydride of Example 1, 418 grams of di(3-aminopropoxy ethyl) ether and 500 grams of mineral oil is heated at -170 C. for 4 hours. A total of 17 grams of water is collected as the distillate. The residue is diluted with 433 grams of mineral oil heated to 160 C. and filtered. The filtrate has the nitrogen content of 2.18%.
- Example 37 A mixture of 1000 grams of the polyisobutene-substituted succinic anhydride of Example 1 and 361 grams of a technical tertiary-alkyl primary amine wherein the tertiary-alkyl radical contains 1214 carbon atoms and 500 grams of mineral oil is heated at -250 C. for 13 hours while being urged with nitrogen. The reisdue is then heated to 150 C./1 mm., diluted with 337 grams of mineral oil, heated to C. and filtered. The filtrate has a nitrogen content of 0.87%.
- Example 38 A mixture of 1000 grams of the polyi-sobutene-substi tuted succinic anhydride of Example 1, 254 grams of aminoguanidine bicarbonate and 500 grams of mineral 13 oil is prepared at 80 C. and heated at 130-165 C. for hours. The residue is mixed with 223 grams of mineral oil, heated to 150 C., and filtered. 'The filtrate has the nitrogen content of 338%.
- Example 39 A mixture of 1000 grams of the polyisobutene-substituted succinic anhydride of Example 1, 178 grams of 2-amino pyridine and 500 grams of mineral oil is heated at 140-175 C. for hours while being purged with nitrogen. A total of 16 grams of water is collected as the distillate. The residue is diluted wtih 273 grams of mineral oil and filtered. The filtrate has a nitrogen content of 2.55%.
- Example 40 A mixture of 1000 grams of the polyisobutene-substituted succinic anhydride of Example 1, 103 grams of 2,6- di-amino-pyridine and 500 grams of mineral oil is heated at 140-180 C. for 11 hours while being purged with nitrogen. A total of 16 grams of water is collected as the distillate. The residue is diluted with 223 grams of mineral oil, heated to 150 C. and filtered. The filtrate has a nitrogen content of 2.15%.
- Example 41 A mixture of 1000 grams of polyisobutene-substituted succinic anhydride of Example 1 159 grams of cyanoguanidine and 233 grams of toluene is heated at the reflux temperature for 14 hours while 7.15 grams of water is removed by azeotropic distillation. The mixture is diluted with 740 grams of mineral oil and toluene is then removed by heating the mixture to 150 C. The residue is filtered and the filtrate has the nitrogen content of 4.74%.
- Example 42 A mixture of 1632 grams of polyisobutene-substituted succinic anhydride of Example 1 207 grams of a condensation product of acrolein with ammonia (molar ratio of 1:1) having a nitrogen content of 604 grams of mineral oil and 1750 grams of toluene is heated at the reflux temperature for 3 hours. A total of 31 grams of water is removed as the distillate. Toluene is then removed by heating the mixture to 150 C./20 mm. The residue is found to have a nitrogen content of 1.89%.
- Example 43 A nitrogen-containing compound is prepared by mixing 100 grams of cyanoguanidine with 500 grams of ethylene amine mixture having an average composition corresponding to that of tetraethylene pentamine and heating the mixture at 7080 C. for 3 hours to obtain a homogeneous mass and filtering the mass.
- a mixture of 1000 grams of the polyisobutene-substituted succinic anhydride of Example 1 96 grams of the above filtrate and 164 grams of toluene is heated at the reflux temperature for 10 hours. Toluene is then removed by heating the mixture to 150 C./ 20 mm. The residue is diluted with 400 grams of mineral oil and filtered. The filtrate has a nitrogen content of 3.43%.
- Example 44 To a mixture of 544 grams of the polyisobutene-substituted succinic anhydride of Example 1 283 grams of mineral oil and 281 grams of toluene there is added 30 grams of urea at 45 C. The resulting mixture is heated at l30-135 C. for 11 hours whereupon 2.5 cc. of water is removed as the distill-ate. The residue is then heated to 140 C./ 20 mm. and filtered. The filtrate has a nitrogen content of 1%.
- Example 45 A mixture of 1088 grams of the polyisobutene-substituted succinic anhydride of Example 1, 106 grams of dipropylene triamine, 500 grams of toluene is heated at the reflux temperature for 4 hours until no more water distills. The residue is then heated to 150 C./ 20 mm. and
- the oil solution is found to have a nitrogen content of 1.74%.
- Example 46 A mixture of 1000 grams of the polyisobutane-substituted succinic anhydride of Example 1, 174 grams of phenylbiguanide and 270 grams of toluene is heated at the reflux temperature for 6.5 hours whereupon 25 grams of water is removed by distillation. The residue is diluted with 500 grams of mineral oil and heated to C./20 mm. to distill off toluene. The-residue is diluted further with 265 grams of mineral oil, heated to 150 C. and filtered. The filtrate has a nitrogen content of 3.4%.
- Example 47 A mixture of 920 grams of the polyisobutene-substituted succinic anhydride of Example 1, and 249 grams of bis-(dimethylaminopropyl)amine is heated at the reflux temperature until no more water distills. The residue has a nitrogen content of 4%.
- Example 48 A mixture of 1000 grams of the polyisobutene-substituted succinic "anhydride of Example 1, 363 grams of aminopropyl octadecylamine and 1314 grams of mineral oil is heated at 2000 C. for 24 hours. The residue is filtered. The filtrate has a nitrogen content of 1.02%.
- Example 49 A mixture of 1000 grams of the polyisobutene-sub-stituted succinic anhydride of Example 1, and 258 grams of di-n-butylamine is heated at C. for 12 hours and then to 200 C./ 25 mm. The residue is diluted with 1157 grams of mineral oil and filtered. The filtrate has a nitrogen content of 0.8%.
- Example 50 A mixture of 297 grams of the polyisobutene-substituted succinic anhydride of Example 1, 25 grams of melamine and 200 grams of mineral oil is heated at 250 C. for 9 hours and then at 290295C. for 7 more hours. The residue is mixed with 50 grams of water, heated at reflux for 7 hours, dried and filtered.
- the filtrate has a nitrogen content of 2%.
- Example 51 A mixture of 100 grams of the polyisobutene-substituted succinic anhydride of Example 1 and 67 grams of mineral oil is heated to 50C. To this mixture there is added 59 grams of a 85% aqueous solution of hydrazine hydrate. The mixture is heated at 100 1l0 C. for 1.25 hours, diluted with toluene, and heated at 107 C. until no more water distills. Toluene is removed by distillation. The residue has a nitrogen content of 0.8%.
- Example 52 A product is obtained by the procedure of Example 1, except that pyrrolidine (1 equivalent) is used in lieu of the diethylene triamine used.
- Example 54 A product is obtained by the procedure of Example 1, except that hexahydro-1,3,5-triazine (1 equivalent) is used in lieu of the diethylene triamine used.
- Example 55 A product is obtained by the procedure of Example 1, except that 1,3,4-dithi-azolidine (1 equivalent) is used in lieu of the diethylene triamine used.
- Example 56 A product is obtained by the procedure of Example 1, except that hexamethylene tetramine (2 equivalents) is used in lieu of the diethylene triamine used.
- Example 5 7 A product is obtained by the procedure of Example 1, except that tripentylene tetramine (3 equivalents) is used in lieu of the diethylene triamine used.
- Example 58 An equi-mol'ar mixture of the polyisobutene-substituted succinic anhydride of Example 1 :and N-octyl thiourea is diluted with an equal volume of xylene. The resulting mixture is heated at the reflux temperature :for 30 hours. The residue is a xylene solution of the product.
- Example 59 A product is obtained by the procedure of Example 58 except that oleylamide is used in lieu of the thiourea used.
- Example 60 A product is obtained by the procedure of Example 58 except that 1,3-diphenyl guanidine is used in lieu of the thiourea used.
- Example 61 A product is obtained by the procedure of Example 58 except that octadecamidine is used in lieu of the thiourea used.
- Example 62 A product is obtained by the procedure of Example 58 except that 'guanylurea is used in lieu of the thiourea used.
- Example 63 To a mixture of 396 grams of the polyisobutene-substituted succinic anhydride of Example 1 and 282 grams of mineral oil there was added 34 grams of N-methyltrimethylene diamine at 60 C. within a period of one hour. The mixture was blown with nitrogen at 150- 155 C. for 5 hours. The residue was found to have a nitrogen content of 1.41%.
- Example 64 A mixture of 386 grams of mineral oil, 528 grams of the polyisobutene-substituted succinic anhydride of Example 1, and 59 grams of N-(Z-hydroxyethyl) -trimethylenediamine was prepared at 60 C. The mixture was blown with nitrogen at 150-155 C. for 5 hours. The residue had a nitrogen content of 1.56%.
- Example 66 A mixture of 185 grams of mineral oil, 330 grams of the polyisobutene-substituted succinic anhydride of Example 1, and 88.5 grams of 1,4-bis(2-hydroxypropyl)-2- methyl piperazine was prepared at 60 C. The mixture The residue has a nitrogen content of 1.12%.
- Example 67 To a mixture of 314 grams of mineral oil and 430 grams of the polyisobutene-substituted succinic anhydride of Example 1 there was added at 60 C., 49 grams of 1-(2-hydroxyethyl) piperazine. The mixture was heated to C. and blown with nitrogen at this temperature for 5 hours. The residue had a nitrogen content of 1.38%.
- Example 68 A mixture of 382 grams of mineral oil, 528 grams of the polyisobutene-substituted succinic anhydride of Example 1, and 53 grams of 14nethyl-4-(3-a-minopropyl) piperazine was prepared at 6 0 C., heated to 150 C., and blown with nitrogen at 150-155 C. for 5 hours. The residue has a nitrogen content of 1.57%.
- Example 69 To a mixture of 800 grams of the polyisobutene-substituted succinic anhydride of Example 1 and 175 grams of toluene there was added 77 'grams of a commercial mixture of alkylene amines and hy-droxy alkyl-substituted alkylene amines consisting of approximately 2% (by weight) of diethylene triamine, 36% of 1-(2-aminoethyl)- piperazine, 11% of 1-(2-hydroxyethyl)piperazine, 11% of N-(2 hydroxyethyl)ethylenediamine, and 40% of higher homologues obtained as a result of condensation of the above-indicated amine components.
- the resulting mixture was heated at the reflux temperature for 16.5 hours whereupon 12 cc. of water was collected as the distillate. The residue was then heated to C./25 mm. and diluted with 570 grams of mineral oil. The final product was found to have a nitrogen content of 1.57%.
- Example 70 A product is obtained by the procedure of Example 58 except that an equimolar mixture of ammonia and bis(2-hydroxyethyl)amine is used in lieu of the thiourea used.
- Example 71 A product is obtained by the procedure of Example 58 except that benzidine is used in lieu of the thiourea used.
- Example 72 An acylated nitrogen composition is prepared according to the procedure of Example 1 except that the reaction mixture consists of 3880 grams of the polyisobutcnyl succinic anhydride, 376 grams of a mixture of triethylene tetramine and diethylene triamine (75:25 weight ratio), and 2785 grams of mineral oil. The product is found to have a nitrogen content of 2%.
- Example 73 An acylated nitrogen composition is prepared according to the procedure of Example 31 except that the polyisobutene-substituted succinic anhydride of Example 1 (1 equivalent for 1.5 equivalents of the amine reactant) is substituted for the polypropylene-substituted succinic anhydride used.
- Example 75 An acylated nitrogen composition is prepared according to the procedure of Example 31 except that the polyisobutene-substituted succinic anhydride of Example 1,
- Example 76 An acylated nitrogen composition is prepared according to the procedure of Example 4 except that the commercial ethylene amine mixture (1.5 equivalent per equivalent of the anhydride) of Example 7 is substituted for the triethylene tetramine used.
- Example 77 An acylated nitrogen composition is prepared according to the procedure of Example 31 except that the polyisobutene-substituted succinic anhydride of Example 1 (1 equivalent for 1 equivalent of the amine reactant) is substituted for the polypropylene-substituted succinic anhydride. The composition is found to have a nitrogen content of 1.5%.
- the boron compounds useful in reaction with the acylated nitrogen compositions include boron oxide, boron oxide hydrate, boron trifiuoride, boron tribromide, boron trichloride, boron acids such as boronic acid (e.g., alkyl- B(OH) or aryl-B(OH) boric acid (i.e., H BO tetraboric acid (i.e., H B O metaboric acid (i.e. HBO and esters of such boron acids.
- boronic acid e.g., alkyl- B(OH) or aryl-B(OH) boric acid
- H BO tetraboric acid i.e., H B O metaboric acid (i.e. HBO and esters of such boron acids.
- the use of complexes of a boron trihalide with ethers, organic acids, inorganic acids, or hydrocarbons is a convenient means of introducing the boro
- Such complexes are known and are exemplified by boron-trifiuoride-diethyl ester, boron trifluoride-phosphoric acid, boron trichloride-chloroacetic acid, boron tribromide-dioxane, and boron trifluoride-methyl ethyl ether.
- boronic acids include methyl boronic acid, phenyl-boronic acid, cyclohexyl boronic acid, p-heptylphenyl boronic acid and dodecyl boronic acid.
- the boron acid esters include especially mono-, di-, and tri-organic esters of boric acid with alcohols or phenols such as, e.g., methanol, ethanol, isopropanol, cyclohexanol, cyclopentanol, l-octanol, 2-octanol, dodecanol, behenyl alcohol, oleyl alcohol, stearyl alcohol, benzyl alcohol, 2- butyl cyclohexanol, ethylene glycol, propylene glycol, trimethylene glycol, 1,3-butanediol, 2,4-hexanediol, 1,2- cyclohexanediol, 1,3-octanediol, glycerol, pentaerythritol diethylene glycol, carbitol, Cellosolve, triethylene glycol, tripropylene glycol, phenol, naphthol, p-but
- one method involves the reaction of boron trichloride with 3 moles of an alcohol or a phenol to result in a tri-organic borate.
- Another method involves the reaction of boric oxide with an alcohol or a phenol.
- Another method involves the direct esterification of tetra boric acid with 3 moles of an alcohol or a phenol.
- Still another method involves the direct esterification of boric acid with a glycol to form, e.g., a cyclic alkylene borate.
- the reaction of the acylated nitrogen compositions with the boron compounds can be effected simply by mixing the reactants at the desired temperature.
- the use of an inert solvent is optional although it is often desirable, especially when a highly viscous or solid reactant is present in the reaction mixture.
- the inert solvent may be a hydrocarbon such as benzene, toluene, naphtha, cyclohexane, n-hexane, or mineral oil.
- the temperature of the reaction may be varied within wide ranges. Ordinarily it is preferably between about 50 C. and about 250 C. In some instances it may be 25 C. or even lower. The upper limit of the temperature is the decomposition point of the particular reaction mixture.
- the reaction is usually complete within a short period 18 such as 0.5 to 6 hours.
- the product may be dissolved in the solvent and the resulting solution purified by centrifugation or filtration if it appears to be hazy or contain insoluble substances. Ordinarily the product is sufiiciently pure so that further purification is unnecessary or optional.
- the reaction of the acylated nitrogen compositions with the boron compounds results in a product containing boron and substantially all of the nitrogen originally present in the nitrogen reactant. It is believed that the reaction results in the formation of a complex between boron and nitrogen. Such complex may involve in some instances more than one atomic proportion of boron with one atomic proportion of nitrogen and in other instances more than one atomic proportion of nitrogen with one atomic proportion of boron.
- the nature of the complex is not clearly understood. Evidence appears to indicate that the complex results from a direct linkage between boron and nitrogen and that in most instances, the radicals originally present in the boron and the nitrogen atoms do not take part directly in the complex formation. However, in the case of a boron acid as the reactant, the reaction is often accompanied with the formation of water.
- the relative proportions of the reactants to be used in the process are based primarily upon the consideration of utility of the products for the purposes of this invention.
- useful products are obtained from reaction mixtures in which the reactants are present in relative proportions as to provide from about 0.1 atomic proportions of boron for each mole of the acylated nitrogen composition used to about 10 atomic proportions of boron for each atomic proportion of nitrogen of said acylated nitrogen composition used.
- the preferred amounts of reactants are such as to provide from about 0.5 atomic proportion-of boron for each mole of the acylated nitrogen composition to about 2 atomic proportions of boron for each atomic proportion of nitrogen used.
- the amount of a boron compound having one boron atom per molecule to be used with one mole of an acylated nitrogen composition having five nitrogen atoms per molecule is within the range from about 0.1 mole to about 50 moles, preferably from about 0.5 mole to about 10 moles.
- Example A To 600 grams (1 atomic proportion of nitrogen) of the acylated nitrogen composition prepared according to the process of Example 77 there is added 45.5 grams (0.5 atomic proportion of boron) of boron trifiuoridediethyl other complex (1:1 molar ratio) at 60-75 C. The resulting mixture is heated to 103 C. and .then at C./30 mm. to distill 011 all volatile components. The residue is found to have a nitrogen content of 1.44% and a boron content of 0.49%.
- Example B A mixture of 62 grams (1 atomic proportion of boron) of boric acid and 1645 grams (2.35 atomic proportions of nitrogen) of the acylated nitrogen composition obtained by the process of Example 72 is heated at C. in nitrogen atmosphere for 6 hours. The mixture is then filtered and the filtrate is found to have a nitrogen content of 1.94% and a boron content of 0.33%.
- Example C An oleyl ester of boric acid is prepared by heating an equi-molar mixture of oleyl alcohol and boric acid in toluene at the reflux temperature while water is removed azeotropically. The reaction mixture is then heated to 150 C./20 mm. and the residue is the ester having a boron content of 3.2% and a saponification number of 62. A mixture of 344 grams (1 atomic proportion of boron) of the ester and 1645 grams (2.35 atomic proportions of nitrogen) of the acylated nitrogen composition obtained by the process of Example 72 is heated at 150 C. for 6 hours and then filtered. The filtrate is found to have a boron content of 0.6% and a nitrogen content of 1.74%.
- Example D A mixture of 344 grams (1 atomic proportion of boron) of the oleyl ester of boric acid of Example C and 1112 grams (2.86 atomic proportions of nitrogen) of the acylated nitrogen composition obtained by the proc-' ess of Example 73 is heated at 150 C. for 6 hours and filtered. The filtrate is found to have a nitrogen con tent of 1.94% and a boron content of 0.81%.
- Tri-isobutylborate is prepared by heating a mixture of 620 grams moles) of boric acid, 2220 grams (30 moles) of isobutyl alcohol, and 800 grams of toluene at the reflux temperature while water formed during esterifi cation is being removed by azeotropic distillation. The reaction mass is then heated at 100 C./20 mm. to distill off toluene and the borate is recovered by distillation at 105 -1 10 C./20 mm. The distillate is found to have a boron content of 5.2%.
- a mixture of 57 grams (0.27 atomic proportion of boron), 13 grams of mineral oil, and 1045 grams (1.56 atomic proportions of nitrogen) of the product obtained by the process of Example 74 is heated at 150-160 C. for 3 hours and then blown with nitrogen at 170 C. (no volatile substance is formed). The mixture is then heated to 150 C./20 mm. and the residue is found to have a boron content of 0.39% and a nitrogen content of 1.98%.
- Example F Boron trifiuoride (34 grams, 0.5 atomic proportion of boron) is bubbled into 1400 grams (1.5 atomic proportion of nitrogen) of the product prepared according to the process of Example 77 at 80 C. within a period of 3 hours. The resulting mixture is blown with nitrogen at 70-80 C. for 2 hours and diluted with 23 grams of mineral oil. The residue is found to have a boron content of 0.42%, a fluorine content of 1.58%, and a nitrogen content of 1.41%.
- Example G A mixture of 31 grams (0.5 atomic proportion of boron) of boric acid and 1175 grams (1.75 atomic proportions of nitrogen) of the acylated nitrogen composition prepared by the process of Example 74 is heated at 150 C. for 3 hours and filtered. The filtrate is found to have a boron content of 0.43% and a nitrogen content of 1.85%.
- Example H A complex of phosphoric acid with 3 moles of boron trifiuoride (67.3 grams, 0.62 atomic proportion of boron) is added dropwise to amixture of 1344 grams (1.92 atomic proportions of nitrogen) of the acylated nitrogen composition of Example 74 and 432 grams of mineral oil. An exothermic reaction occurs. The mixture is heatedat 80-90 C. for 0.5 hour and mixed with 520 cc. of benzene. The resulting solution is washed with, successively, 500 cc. of water, a mixture of 500 cc. of water and 250 cc. of isopropyl alcohol, 50 cc. of a saturated sodium chloride solution, and a mixture of 750 cc.
- the washed product is heated to 150 C./38'-68 mm. within a period of 6 hours, cooled, and filtered.
- the filtrate is found to have a nitrogen content of 1.34% and a boron content of 0.1%.
- Example I A mixture of 12 grams (0.38 mole) of sulfur, 124
- Example 75 20 grams (2 atomic proportions of boron) of boric acid, and 1018 grams (2 atomic proportions of nitrogen) of the acylated nitrogen composition of Example 75 is heated at 150 C. for 3 hours and filtered. The filtrate is found to have a nitrogen content of 2.4%, a boron content of 1.68%, and a sulfur content of 0.5%.
- Example I The process of Example I is repeated except that thiourea (38 grams, 0.5 mole) is substituted for the sulfur used. The product is found to have a nitrogen content of 3.3%, a sulfur content of 1.44%, and a boron content of 1.75%.
- Example K A mixture of 55 grams (0.39 atomic proportion of boron) of boron trifluoride-diethyl ether complex (1:1 molar ratio) and 480 grams (0.77 atomic proportion of nitrogen) of the'product of Example 76 is heated at 80-90 C. for 0.5 hour and then to C./30 mm. The residue is found to have a nitrogen content of 2.08% and a, boron content of 0.76%.
- Example L A mixture of 372 (6 atomic proportions of boron) of boric acid and 3111 grams (6'atomic proportions of nitrogen) of the acylated nitrogen composition obtained by the process of Example 75 is heated at C. for 3 hours and then filtered. The filtrate is found to have a boron content of 1.64% and a nitrogen content of 2.56%
- Example M Boric acid (124 grams, 2 atomic proportions of boron) is added to the acylated nitrogen composition (556 grams, 1 atomic proportion of nitrogen) obtained ac- "cording to the procedure of Example 75. The resulting mixture is heated at 150 C. for 3.5 hours and filtered at that temperature. The filtrate is found to have a boron compound of 3.23% and a nitrogen content of 2.3%.
- Example 0 A mixture of boric acid and the acylated nitrogen composition prepared according to the procedure of Example 17 in relative proportions such as to provide 1 atomic proportion of boron per atomic proportion of nitrogen is diluted with twice its volume of xylene and the resulting mixture heated at 150 C. for 3 hours and filtered. Xylene is removed by heating the filtrate to 150 C./ 0.25 mm. The residue is found to have a boron content of 0.42% and a nitrogen content of 0.44%.
- Example P A mixture of boric acid and the acylated nitrogen composition obtained according to the procedure of Example 44 in relative proportions such as to provide 1 atomic proportion of boron per atomic proportion of nitrogen is heated at 150 C. for 3 hours and filtered. The filtrate is found to have a boron content of 0.2%.
- Example Q A mixture of boric acid and an acylated nitrogen compositionobtained by the procedure of Example 41 in relative proportions such as to provide 1 atomic proportion of boron per atomic proportion of nitrogen isheated at 21 150 C. for 3 hours and filtered at this temperature. The filtrate is found to have a boron content of 3.1% and a nitrogen content of 4.1%.
- Example R A mixture of boron trifiuoride-diethyl ether complex and a polyisobutene-substituted succinimide derived from a polyisobutene having an average molecular weight of 1000 in relative proportions such as to provide 1 atomic proportion of boron per atomic proportion of nitrogen is heated at 150 C. for 3 hours and filtered at this temperature.
- Example S A mixture of boric acid and the acylated nitrogen composition obtained by the procedure of Example 37 in relative proportions such as to provide 1 atomic proportion of boron per atomic proportion of nitrogen is heated at 150 C. for 3 hours and filtered.
- Example T A mixture of boric acid and the acylated nitrogen composition obtained according to the procedure of Example 25 in relative proportions such as to provide 1 atomic proportion of boron per atomic proportion of nitrogen is heated at 150 C. for 3 hours and filtered.
- the nitrogen and boron-containing products of this invention are useful for a wide variety of purposes including pesticides, plasticizers, rust inhibiting agents for treatment of metals, corrosion-inhibiting agents, extreme pressure agents, anti-wear agents, and detergents.
- a principal utility of such products is as additives in lubricants. It has been discovered in accordance with this invention that when used for such purpose the effectiveness of the nitrogenand boron-containing products to impart a specific property to a lubricant is closely related to the size of the substantially hydrocarbon substituent in the succinic radical of the acylated nitrogen composition from which such products are derived. More particularly it has been found that products in which the substantially hydrocarbon substitutent contains more than about 50 aliphatic carbon atoms are effective to impart oxidation-inhibiting, corrosion-inhibiting, and detergent properties to a lubricant.
- the lubricating oils in which the compositions of this invention are useful as additives may be of synthetic, animal, vegetable, or mineral origin. Ordinarily mineral lubricating oils are preferred by reason of their availability, general excellence, and low cost. For certain applications, oils belonging to one of the other three groups may be preferred. For instance, synthetic polyester oils such as didodecyl adipate and di-Z-ethylhexyl sebacate are often preferred as jet engine lubricants. Normally the lubricating oils preferred will be fluid oils, ranging in viscosity from about 40 Saybolt Universal seconds at 100 F. to about 200 Saybolt Universal seconds at 210 F.
- the concentration of the nitrogenand boron-containing compositions as additives in lubricants usually ranges from about 0.1% to about 10% by weight.
- the optimum concentrations for a particular application depend to a large measure upon the type of service to which the lubricants is to be subjected.
- lubricants for use in gasoline internal combustion engines may contain from about 0.5 to about 5% of the additive, whereas lubricating compositions for use in gears in diesel engines may contain as much as or even more of the additive.
- additives include, for example, supplemental detergents of the ashcontaining type, viscosity index improving agents, pour point depressing agents, anti-foam agents, extreme pressure agents, rust-inhibiting agents, and supplemental oxidation and corrosion inhibiting agents.
- the ash-containing detergents are exemplified by oilsoluble neutral and basic salts of alkali or alkaline earth metals with sulfonic acids, carboxylic acids, or organic phosphorus acids characterized by at least one direct carbon-to-phosphorus linkage such as those prepared by the treatment of an olefin polymer (e.g., polyisobutene having a molecular weight of 1000) with a phosphorizing agent such as phosphorus trichloride, phosphorus heptasulfide, phosphorus pentasulfide, phosphorus trichloride and sulfur, White phosphorus and a sulfur halide, or phosphorothioic chloride.
- olefin polymer e.g., polyisobutene having a molecular weight of 1000
- a phosphorizing agent such as phosphorus trichloride, phosphorus heptasulfide, phosphorus pentasulfide,
- the term basic salt is used to designate the metal salts wherein the metal is present in stoichiometrically larger amounts than the organic acid radical.
- the commonly employed methods for preparing the basic salts involves heating a mineral oil solution of an acid with a stoichiometric excess of a metal neutralizing agent such as the metal oxide, hydroxide, carbonate, bicarbonate, or sulfide at a temperature about 50 C. and filtering the resulting mass.
- a metal neutralizing agent such as the metal oxide, hydroxide, carbonate, bicarbonate, or sulfide
- Examples of compounds useful as the promoter include phenolic substances such as phenol, naphthol, alkylphenol, thiophenol, sulfurized alkylphenol, and condensation products of formaldehyde with a phenolic substance; alcohols such as methanol, 2- propanol, octyl alcohol, Cellosolve, carbitol, ethylene glycol, stearyl alcohol, and cyclohexyl alcohol; amines such as aniline, phenylenediarnine, phenothiazine, phenylbeta-naphthylamine, and dodecylamine.
- phenolic substances such as phenol, naphthol, alkylphenol, thiophenol, sulfurized alkylphenol, and condensation products of formaldehyde with a phenolic substance
- alcohols such as methanol, 2- propanol, octyl alcohol, Cellosolve, carbitol, ethylene glycol, stearyl alcohol
- a particularly efiective method for preparing the basic salts comprises mixing an acid with an excess of a basic alkaline earth metal neutralizing agent, a phenolic promoter compound, and a small amount of Water and carbonatin g the mixture at an elevated temperature such as 60-200 C.
- chlorinated aliphatic hydrocarbons such as chlorinated Wax
- organic sulfides and polysulfides such as benzyl disulfide, bis- (chlorobenzyl) disulfide, dibutyl tetrasulfide, sulfurized sperm oil, sulfurized methyl ester of oleic acid, sulfurized alkylphenol, sulfurized dipentene, and sulfurized terpene
- phosphosulfurized hydrocarbons such as the reaction product of a phosphorus sulfide with turpentine or methyl oleate
- phosphorus esters including principally dihydrocarbon and trihydrocarbon phosphites such as dibutyl phosphite, diheptyl phosphite, dicyclohexyl phosphite, pentyl phenyl phosphite, dipentyl
- the lubricating compositions may also contain metal detergent additives in amounts usually within the range of about 0.1% .to about 20% by weight. In some applications such as in lubricating marine diesel engines the lubricating compositions may contain as much as 30% of the metal detergent additive. They may also contain extreme pressure addition agents, viscosity in- 23... dex improving agents, and pour point depressing agents, each in amounts within the range from about 0.1% to about 10%.
- Example III SAE 10W-30 mineral lubricating oil containing 0.4% of the product of Example C.
- Example V SAE 30 mineral lubricating oil containing 2% of the product of Example M.
- Example VI SAE 20W-30 mineral lubricating oil containing of the product of Example M.
- Example VII SAE W-30 mineral lubricating oil containing 1.5% of the product of Example E and 0.05% of phosphorus as the Zinc salt of a phosphorodithioic acid prepared by the reaction of phosphorus pentasulfide with a mixtur of 60% (mole) of p-butylphenol and 40% (mole) of npentyl alcohol.
- Example XI SAE 1OW-30 mineral lubricating oil containing 6% of the product of Example I, 0.075% of phosphorus as zinc di-n-octylphospho-rodithioate, and 5% of the barium salt of an acidic composition prepared by the reaction of 1000 parts of a polyisobutene having a molecular weight of 60,000 with 100 parts of phosphorus pentasulfide at 200 C. and hydrolyzing the product with steam at 150 C.
- Example XVII SAE 10 mineral lubricating oil containing 3% of the product of Example 0, 0.075% of phosphorus as the zinc salt of a phosphorodithioic acid prepared by the reaction of phosphorus pentasulfide with an equimolar mixture of n-butyl alcohol and dodecyl alcohol, 3% of a barium detergent prepared by canbonating a mineral oil solution containing 1 mole of sperm oil, 0. 6 mole of octylphenol, 2 moles of barium oxide, and a small amount of water at 150 C.
- Example S 25 product of Example S and 0.2% of phosphorus as the reaction product of 4 moles of turpentine with 1 mole of phosphorus pentasulfide.
- the effect veness of the nitrogenand boron-containing compositions as additives in lubricants to impart oxidationinhibiting, corrosion-inhibiting, and detergent properties is illustrated by the results obtained from an inhibitiondetergency test in which a 350 cc. sample of a lubricant containing 0.001% of iron naphthenate and 1.5% by weight of the additive vto be tested is heated at 300 F. for 48 hours in a 2 x 15 lborosilicate tube. A clean copperlead bearing is immersed in the lubricant along with an SAE 1020 steel test panel. Air is bubbled through the lubricant at the rate of 10 liters per hour. The oxidized sample is allowed to cool to 122 F.
- the quantity of sludge is an indication of the ability of the additive to prevent the formation of harmful deposits
- the bearing weight change is an indication of the corrosiveness of the lubricant
- the viscosity change of the lubricant is an indication of the oxidation resistance of the lubricant.
- the lubricant base employed in the test is a Mid-Continent, conventionally refined mineral oil having a viscosity of about 200 Saybolt Universal seconds at 100 F. The results of the test are summarized in Table I below.
- the lubricant is then rated according to (1) the extent of piston ring-filling, (2) the amount of sludge formed in the engine (on a scale of -0, 80 being indicative of no sludge and 0 being indicative of extremely heavy sludge), and 3) the total amount of deposits, i.e., sludge and varnish, formed in the engine (on a scale of -0, 100 being indicative of no deposit and 0 being indicative of extremely heavy deposits).
- the lubricant used in the test comprises .an SAE 20 mineral .oil containing 1.41% by weight of the product of Example L. The lubricant is found to pass the test with the following result: ring filling, 1%; sludge rating, 75.3; total deposit rating, 93.4.
- BTU input per minute 2900- 5000; load, 20 brake-horsepower; water jacket outlet temperature, -180 'F.; and oil temperature, 145-150 F.
- the lubricant is evaluated in terms of 1) the piston cleanliness rating on a scale of 0-100 (100 being perfectly clean and 0 representing maximum deposit) and (2) percent ring filling.
- a lubricant comprising a SAE 10W-30 mineral oil containing 2% by Weight of the product of Example L is found to pass this test with the following result: ring filling, 19%; piston cleanliness, 96.0.
- the eifectiveness of the nitrogenand boron-containing compositions of this invention as additives in lubricants for internal combustion engines is evaluated further by the CRCL4545 engine test.
- This test involves the operation of a 6-cylinder gasoline automobile engine for 36 hours under the following conditions: engine speed, 3150 r.p.m.; engine load, 30 brake-horsepower; jacket coolant temperature, outlet 200 F., inlet F.; oil sump temperature, 265 F.; and air-fuel ratio, 14.521.
- the lubricant is rated in terms of the weight loss of bearings, the cleanliness of the pistons and the overall varnish and sludge deposits on the various parts of the engine.
- a lubricant comprising a SAE 10W-3O mineral oil containing 2.08% by weight of the product of Example L is found to pass the test with the following results: piston cleanliness rating of 9.5 10 being perfectly clean), overall varnish and sludge rating of 96.7 (100 being perfectly clean), and an average weight loss per bearing of 2.5 milligrams.
- the utility of the nitrogenand boron-containing compositions of this invention as additives in lubricants for use in 2-cycle internal combustion engines illustrated by the results of an engine test in which a 7-horsepower chain saw engine (McCulloch model No. 1-80) is operated for 25 hours under the following recurring cycling conditions, each cycle consisting of 15 minutes at zero load and 1800-2200 rpm. and 5 minutes at adjustable load and 5000 rpm.
- the lubricant comprises a SAE 30 mineral oil containing 7% by volume of the product of Example M and is incorporated in the fuel mixture consisting of 20 parts by volume of a leaded gasoline having an octane number of 95 and 1 part by volume of the lubricant.
- the lubricant is found to give by this test a piston varnish rating of 7.0 (on a scale of 0 10, 10 being indicative of no varnish and 0 being indicative of extremely heavy varnish) and a crankcase cover varnish rating of 10.0 (on the same scale as above) whereas the base 27 oil, i.e., SAE 30 mineral oil, gives a piston varnish rating of 2.5 and a crankcase cover varnish rating of 8.
- a process for preparing oil-soluble nitrogenand boron-containing compositions comprising forming an acylated nitrogen intermediate by the reaction at a temperature within the range of from about 80 to about 250 C., of a substantially aliphatic olefin polymer-substituted succinic acid-producing compound having at least about 50 aliphatic carbon atoms in the polymer substituent with at least about one-half equivalent of an amine, for each equivalent of the acid-producing compound used, selected from the class consisting of alkylene amines and hydroxy-substituted ⁇ alkylene amines, and reacting, at a temperature between about 50 C.
- said acylated nitrogen intermediate with a boron compound selected from the class consisting of boron oxide, boron halide, boron acids, and esters of boron acids in an amount to provide from about 0.1 atomic proportion of boron for each mole of said acylated nitrogen intermediate to about atomic proportions of boron for each atomic proportion of nitrogen of said acylated nitrogen intermediate.
- a boron compound selected from the class consisting of boron oxide, boron halide, boron acids, and esters of boron acids in an amount to provide from about 0.1 atomic proportion of boron for each mole of said acylated nitrogen intermediate to about atomic proportions of boron for each atomic proportion of nitrogen of said acylated nitrogen intermediate.
- polymer substituent of the succinic acid-producing compound is derived from a polyisobutene having an average molecular weight within the range from about 700 to about 5000.
- An oil-soluble nitrogenand boron-containing composition prepared by the process comprising forming an acylated nitrogen intermediate by the reaction at a temperature within the range of from about 80 C. to about 250 C., of a substantially aliphatic olefin polymer-substituted succinic acid-producing compound having at least about 50 aliphatic carbon atoms in the polymer substituent with at least about one-half equivalent of an amine for each equivalent of acid-producing compound used, selected from the class consisting of alkylene amines and hydroxy-substituted alkylene amines, and reacting at a temperature between about C. and about 250 C.
- said acylated nitrogen intermediate with a boron compound selected from the class consisting of boron oxide, boron halide, boron acids, and esters of boron acids in an amount to provide from about 0.1 atomic proportion of boron for each mole of said acylated nitrogen intermediate to about 10 atomic proportions of boron for each atomic proportion of nitrogen of said acylated nitrogen intermediate.
- a boron compound selected from the class consisting of boron oxide, boron halide, boron acids, and esters of boron acids in an amount to provide from about 0.1 atomic proportion of boron for each mole of said acylated nitrogen intermediate to about 10 atomic proportions of boron for each atomic proportion of nitrogen of said acylated nitrogen intermediate.
Description
' aired States of Ghio Fired Aug. 18, 1961, er. No. 132,395
No Drawing.
1t) Claims. (Ci. 2etl326.3)
This invention relates to oil-soluble nitrogenand boroncontaining compositions and to the process of preparing the same. The compositions of this invention are useful as additives in lubricants, especially lubricants intended for use in internal combustion engines, gears, and power transmitting units.
One of the principal problems associated with present day automobile crankcase lubricants is that posed by the inevitable presence in the lubricant of foreign particles such as dirt, soot, water, and decomposition products resulting from breakdown of the lubricating oil. Even if there were none of this latter contaminant present the very nature of the design of the modern internal combustion engine is such that a significant amount of foreign matter will accumulate in the crankcase. Perhaps the most important of these contaminants is water because it seems to be responsible for the deposition of a mayonnaise-like sludge. It appears that if there were no water present the solid components of the mayonnaiselike sludge would circulate with the oil and be removed by the oil filter. It will be readily appreciated that the deposition of the sludge presents a serious problem with respect to the eificient operation of the engine and that it is desirable to prevent such deposition of sludge-like material.
The presence of water and the precursors of sludge in a lubricating oil is dependent largely upon the operating temperature of the oil. If the oil is operated at a high temperature the water, of course, will be eliminated by evaporation about as fast as it accumulates. In the absence of water as stated above the other foreign particles will be removed by the filter. At low oil temperatures, on the other hand, water will accumulate and so consequently will sludge. It is apparent that the environment in which a crankcase lubricant is maintained will determine to a large extent the ultimate performance of that lubricant.
High operating temperatures are characteristic of a lubricant in an engine that is run at relatively constant high speed. Thus, in an engine that is run at 60 miles per hour for a long period of time it is very unlikely that there will be any accumulation of water and it is similary unlikely that there will be any formation and deposition of sludge, but in ordinary stop-and-go driving such as is the case with taxicabs, delivery trucks, police cruisers, etc., the crankcase lubricant will be alternately hot and cold, an ideal environment for the accumulation of water. In such cases the formation of sludge is a serious problem. This problem has been with the automotive industry for many years and its solution has been approached by the use of known detergents such as metal phenates and sulfonates but without notable success. Although such known detergents are very eflective in solving the detergency problems associated with motor oils at high temperatures they have not been particularly effective in solving the problems associated with low temperature operation or, to put it better, those problems which are associated with crankcase lubricants in engines which are operated at alternating high and low temperatures.
It is accordingly a principal object of this invention to provide novel compositions of matter.
It is also an object of this invention to provide compositions which are adapted for use as additives in hydrocarbon oils.
It is also an object of this invention to provide compositions which are effective as detergents in lubricating compositions.
It is another object of this invention to provide a novel process for the preparation of products which are effective as dispersants in lubricant compositions.
It is another object of this invention to provide novel compositions which are effective dispersants in lubricant compositions intended for used in engines operated at alternating high and low temperatures.
It is another object of this invention to provide improve-d hydrocarbon oil compositions.
It is another object of this invention to provide improved lubricating compositions.
It is another object of this invention to provide improved fuel compositions.
These and other objects are achieved in accordance with this invention by providing a process for preparing oil-soluble nitrogenand boron-containing compositions comprising treating an acylated nitrogen composition characterized by the presence within its structure of (A) a substatnially hydrocar-substituted suc-cinic radical selected from the class consisting of succinoyl, succinimidoyl, and succinoyloxy radicals wherein the substantially hydrocarbon substituent contains at least about 50 aliphatic carbon atoms and (B) a nitrogen-containing group characterized by a nitrogen atom attached directly to said succinic radical, with a boron compound selected from the class consisting of boron oxide, boron halides, boron acids, and esters of boron acids in an amount to provide from about 0.1 atomic proportion of boron for each mole of said acylated nitrogen composition to about 10 atomic proportions of boron for each atomic proportion of nitrogen of said acylated nitrogen composition.
The substantially hydrocarbon substituent of the acylated nitrogen composition may contain polar groups provided, however, that the polar groups are not present in proportions sufliciently large to alter significantly the hydrocarbon character of the substituent. The polar groups are exemplified by chlor-o, bromo, keto, ethereal, aldehydo, and nitro, etc. The upper limit with respect to the proportion of such polar groups in the substituent is ap proximately 10% based on the Weight of the hydrocarbon portion of the substituent.
The sources of the substantially hydrocarbon substituent include principally the high molecular weight substantially saturated petroleum fractions and substantially saturated olefin polymers, particularly polymers of monoolefins having from 2 to 30 carbon atoms. The especially useful polymers are the polymers of l-monoclefins such as ethylene, propene, 1-butene, isobutene, l-hexene, l-octene, Z-methyl-l-heptene, 3-cvcloheXyl-1-butene, and Z-methyl-S-propyl-l-hexene. Polymers of medial olefins, i.e., olefins in which the olefinic linkage is not at the terminal position, likewise are useful. They are illustrated by Z-butene, 3-penetne, and 4-octene.
Also useful are the interpolymers of the olefins such as those illustrated above with other interpolymerizable olefinlc substances such as aromatic olefins, cyclic olefins, and polyolefins. Such interpolymers include, for example, those prepared by polymerizing isobutene with styrene; isobutene with butadiene; propene with isoprene; ethylene with piperylene; isobutene with chloroprene; isobutene with p-methyl styrene; l-heXene with 1,3-hexadiene; 1 octene with l-hexene; 1 heptene with l-pentene;
3-methyl-1-butene with l-octene; 3,3-dimethyl-1-pentene with 1-hexene; isobutene with styrene and piperylene, etc.
The relative proportions of the mono-olefins to the other monomers in the interpolymers influence the stability and oil-solubility of the final products derived from such interpolymers. Thus, for reasons of oil-solubility and stability the interpolymers contemplated for use in this invention should be substantially aliphatic and substantially saturated, i.e., they should contain at least about 80%, preferably at least about 95%, on a weight basis of units derived from the aliphatic monoolefins and no more than about of olefinic linkages based on the total number of carbon-to-carbon covalent linkages. In most instances, the percentage of olefinic linkages should be less than about 2% of the total number of carbon-to-carbon covalent linkages.
Specific examples of such interpolymers include copolymer of 95% (by weight) of isobutene with 5% of styrene; terpolymer of 98% of isobutene with 1% of piperylene and 1% of chloroprene; terpolyrner of 95% ofisobutene with 2% of l-butene and 3% of l-hexene; terpolymer of 80% of isobutene with 20% of l-pentene and 20% of l-octene; copolymer of 80% of l-hexene and 20% of l-heptene; terpolymer of 90% of isobutene with 2% of cyclohexene and 8% of propene; and copolymer of 80% of ethylene and 20% of propene.
Another source of the substantially hydrocarbon radical comprises saturated aliphatic hydrocarbons such as highly refined high molecular weight white oils or synthetic alkanes such as are obtained by hydrogenation of 'high molecular Weight olefin polymers illustrated above or high molecular weight olefinic substances.
The use of olefin polymers having molecular weight of about 750-6000 is preferred. Higher molecular weight olefin polymers having molecular weights from about 10,000 to about 100,000 or higher have been found to impart also viscosity index improving properties to the final products of this invention. The use of such higher molecular weight olefin polymers often is desirable.
The nitrogen-containing group of the acylated nitrogen compositions of this invention is derived from compounds characterized by a radical having the structural configuration The two remaining valences of the nitrogen atom of the above radical preferably are satisfied by hydrogen, amino, or organic radicals bonded to said nitrogen atom through direct carbon-to-nitrogen linkages. Thus, the compounds from which the nitrogen-containing group may be derived include principally ammonia, aliphatic amines, aromatic amines, heterocyclic amines, or carbocyclic amines. The amines may be primary or secondary amines and may also be polyarnines such as alkylene amines, arylene amines, cyclic polyamines, and the hydroxy-substituted derivatives of such polyamines.
Specific amines of these types are methylamine, N-methylethylamine, N-methyl-octylamine, N-cyclohexyl-aniline, dibutylamine, cyclohexylamine, aniline, di(p -rnethyl phenyl)amine, dodecylamine, octadecylamine, o-phenylenediamine, N,N' di n butyl p phenylenediamine, morpholine, piperazine, tetrahydropyrazine, indole, hexahydro-1,3,5-triazine, 1-H-1,2,4-triazole, melamine, bis- (p-aminophenyl)methane, phenyl-methylenimine, menthanediamine, cyclohexamine, pyrrolidine, 3-amino-5,6- diphenyl 1,2,4 triazine, ethanolamine, diethanolamine, quinonediimine, 1,3-indandiimine, 2-octadecylirnidazoline, 2 phenyl 4 methyl imidazolidine, oxazolidine, and Z-heptyl-oxazolidine.
A preferred source of the nitrogen-containing group H1TT (alkylene-ITT) 11H wherein n is an integer preferably less than about 10, A is a substantially hydrocarbon or hydrogen radical, and the alkylene radical is preferably a loWer alkylene radical having less than about 8 carbon atoms. The alkylene amines include principally methylene amines, ethylene amines, butylene amines, propylene amines, pentylene amines, hexylene amines, heptylene amines, octylene amines, other polymethylene amines, and also the cyclic and the higher homologs of such amines such as pipe-razines and amino alkyl substituted piperazines. They are exemplified specifically by: ethylene diamine, triethylene tetramine, propylene diamine, decamethylene diamine, octamethylene diamine, di(heptamethylene)triamine, tripropylene tetramine, tetraethylene pentamine, trimethylene diamine, pentaethylene hexamine, di(trimethylene) triamine, 2 heptyl 3 (2 aminopropyl) imidazoline, 4 methylimidazoline, 1,3 bis(2 aminoethyl).imidazoline, pyrimidine, 1-(Z-aminopropyl)piperazine, 1,4-bis(2-aminoetl1yl) piperazine, and Z-methyl-l- (Z-aminobutyl)piperazine. Higher homologues such as are obtained by condensing two or more of the aboveillustrated alkylene amines likewise are useful.
The ethylene amines are especially useful. They are described in some detail under the heading Ethylene Amines in Encyclopedia of Chemical Technology, Kirk and Othmer, volume 5, pages 898905, Interscieuce Publishers, New York (1950). Such compounds are prepared most conveniently by the reaction of an alkylene chloride with ammonia. The reaction results in the production of somewhat complex mixtures of alkylene amines, including cyclic condensation products such as piperazines. These mixtures find use in the process of this invention. On the other hand, quite satisfactory products may be obtained also by the use of pure alkylene amines. An especially useful alkylene amine for reasons of economy as well as effectiveness of the prodthat of tetraethylene pentamine.
Hydroxyalky -substituted alkylene amines, i.e., alkylene amines having one or more hydroxyalkyl substituents on the nitrogen atoms, likewise are contemplated for use herein. The hydroxyalkyl-substituted alkylene amines are preferably those in which the alkyl rgoup is a lower alkyl group, i.e., having less than about 6 carbon atoms. Examples of such amines include N-(Z-hydroxyethyl) ethylene diamine, N,N bis(2 hydroxyethyl)ethylene diamine, 1 (2 hydroxyethyl)piperazine, mono -.hy droxypropyl substituted diethylene triamine, 1,4 bis(2- hydroxypropyl)piperazine, di-hydroxypropyl-substituted tetraethylene pentamine, N-(3-hydroxypropyl)tetramethylene diamine, and Z-heptadecyl-1-(2-hydroxyethyl) imidazoline.
Higher homologues such as are obtained by condensation of the above-illustrated alkylene amines or hydroxy alkyl-substituted alkylene amines through amino radicals or through hydroxy radical-s are likewise useful. It will be appreciated that condensation through amino radicals results in an higher amine accompanied with removal of ammonia and that condensation through the hydroxy radicals results in products containing either linkages accompanied with removal of Water. 7 Other sources of the nitrogen-containing group include ureas, thioureas, hydrazines, guanidines, amidines, amides, thioamides, cyanamides, etc. Specifice examples illustrating such compounds are: hydrazine, phenylhyrazine, N,N'-diphenylhydrazine, octadecylhydrazine, benzoylhydrazine, urea, thiourea, N-butylurea, stearylamide, oleylamide, guanidine, 1,3 diphenylguanidine,
1,2,3 tributylguanidine, benzamidine, octadecamidine, N,N'-dimethylstearamidine, cyanarnide, dicyandiamide, guanylurea aminoguanidine, etc.
As indicated previously, the nitrogen-containing group in the acylated nitrogen compositions of this invention is characterized by a nitrogen atom attached directly to the scuccinic radical. It will be apperciated, of course, that the linkage between a nitrogen atom and a succinoyl radical is representative of an amide or an imide structure, that the linkage between a nitrogen atom and a succinirnidoyl radical is representative of an arnidine structure, and that the linkage between a nitrogen atom and a succinoyloxy radical is representative of an ammoniumcarboxylic acid salt structure. Thus, the acylated nitrogen compositions of this invention are characterized by amide, amide-salt, imide, amidine, or salt linkages and in many instances a mixture of such linkages.
A convenient method for preparing the acylated nitrogen compositions comprises reacting a high molecular weight succinic acid-producing compound characterized by the presence within its structure of a high molecular weight oil-solubilizing group having at lea-st about 50 aliphatic carbon atoms and at least one succinic acidproducing group. Such compounds are illustrated by one having the structural configuration wherein R is a subsantially hydrocarbon radical having at least about 50 aliphatic carbon atoms and X is selected from the class consisting of halogen, hydroxy, hydrocarbon-oxy, and acyloxy radicals, with a least about onehalf an equivalent amount of a nitrogen-containing compound characterized by the presence within its structure of at least one radical having the structural configuration The above process involves a reaction between the succinic acid-producing group with the nitrogen-containing radical to result in the direct attachment of the nitrogen atoms to the succinic radical, i.e., succinoyl, succinimidoyl, or succinolyloxy radical. The linkage formed between the nitrogen atom and the succinic radical may thus be that representative of a salt, amide, imide, or amidine radical. In most instances the product of the above process contains a mixture of linkages representative of such radicals. The precise relative proportions of such radicals in the product usually are not known as they depend to a large measure upon the type of the acid-producing group and the nitrogen-containing radical involved in the reaction and also upon the environment (e.g., temperature) in which the reaction is carried out. To illustrate, the reaction involving an acid or anhydride group with an amino nitrogen-containing radical at relatively low temperatures such as below about 60 C. results predominantly in a salt linkage l1 (i.e., C-ON) but at relatively high temperatures such as above about 80 C. results predominantly in an amide, imide, or amidine linkage u (i.e., C-N or O--N) In any event, however, the products obtained by the above process, irrespective of the nature or relative proportions of the linkages present therein, have been found to be effective as additives in hydrocarbon oils for the purposes of this invention.
The substantially saturated, aliphatic hydrcarbon-substituted succinic acids and anhydrides are especially preferred for use as the acid-producing reactant of this process for reasons of the particular elfectiveness of the products obtained from such compounds as additives in hydrocarbon oils. The succinic compounds are readily available from the reaction of maleic anhydride with a high molecular weight olefin or a chlorinated hydrocarbon such as the olefin polymer described hereinabove. The reaction involves merely heating the two reactants at a temperature about 100200 C. The product from such a reaction is an alkenyl succinic anhydride. The alkenyl group may be hydrogenater to an alkyl group. The anhydride may be hydrolyzed by treatment with water or steam to the corresponding acid. Either the anhydride or the acid may be converted to the corresponding acid halide or ester by reaction with, e.g., phosphorus halide, phenols, or alcohols.
In lieu of the olefins or chlorinated hydrocarbons, other hydrocarbons containing an activating polar substituent, i.e., a substituent which is capable of activating the hydrocarbon molecule in respect to reaction with maleic acid or anhydride, may be used in the above-illustrated reaction for preparing the succinic compounds. Such polar substituents may be illustrated by sulfide, disulfide, nitro, mercaptan, bromine, ketone, and aldehyde radicals. Examples of such polar-substituted hydrocarbons include polypropene sulfide, di-polyisobutene disulfide, nitrated mineral oil, di-polyethylene sulfide, brominated polyethylene, etc. Another method useful for preparing the succinic acids and anhydrides involves the reaction of itaconic acid with a high molecular weight olefin or a polar-substituted hydrocarbon at a temperature usually within the range from about 100 C. to about 200 C.
The acid halides of the succinic acids can be prepared by the reaction of the acids or their anhydrides with a halogenation agent such as phosphorus tri-bromide, phosphorus pentachloride or thionyl chloride. The esters of such acids can be prepared simply by the reaction of the acids or their anhydrides with an alcohol or a phenolic compound such as methanol, ethanol, octadecanol, cyclohexanol, phenol, naphthol, octylphenol, etc. The esteri-- fioation is usually promoted by the use of an alkaline catalyst such as sodium hydroxide or sodium alkoxide or an acidic catalyst such as sulfuric acid. The nature of the alcoholic or phenolic portion of the ester radical appears to have little influence on the utility of such ester as reactant in the process described hereinabove.
The nitrogen-containing reactants useful in the above process are the compounds, described previously in this specification, from which the nitrogemcontaining group the acylated nitrogen compositions of this inven tion can be derived.
The above process is usually carried out by heating a mixture of the acid-producing compound and the nitrogen-containing reactant at a temperature above C., preferably within the range from about C., to about 250 C. However, when an acid or anhydride is employed in reactions with an amino nitrogen-containing reactant, the process may be carried out at a lower temperature such as room temperature to obtain products having predominantly salt linkages or mixed salt-amide linkages. Such products may be converted, if desired, by heating to above 80 C. to products having predominantly amide, imide, or amidine linkages. The use of a solvent such as benzene, toluene, naphtha, mineral oil, xylene, n-hexane, or the like is often desirable in the above process to facilitate the control of the reaction temperature.
The relative proportions of the acid-producing compounds and the nitrogen-containing reactants to be used in the above process are such that at least about one-half of a stoichiometrically equivalent amount of the nitrogencontaining reactant is used for each equivalent of the acidproducing compound used. In this regard it will be noted that the equivalent weight of the nitrogen-containing reactant is based upon the number of the nitrogen-containing radicals. Similarly the equivalent weight of the acid-producing compound is based upon the number of the acid-producing radicals defined by the structural configuration ll -O-X Thus, ethylene diamine has two equivalents per mole; amino guanidine has four equivalents per mole; a suc-. cinic acid or ester has two equivalents per mole, etc.
The upper limit of the useful amount of the nitrogencontaining reactant appears to be about two equivalents for each equivalent of the acid-producing compound used. Such amount is required, for instance, in the formation of products having predominantly amidine linkages. Beyond this limit, the excess amount of the nitrogen-containing reactant appears not to take part in the reaction and thus simply remains in the product apparently without any adverse effects. On the other hand, the lower limit of about one-half equivalent of the nitrogen-containing reactant used for each equivalent of the acid producing compound is based upon the stoichiometry for the formationof products having predominantly imide linkages. In most instances, the preferred amount of the nitrogen-containing reactant is approximately one equivalent for each equivalent of the acid-producing compound used.
The following examples illustrate the processes useful for preparing the acylated nitrogen compositions useful in the process of this invention:
Example 1 A polyisobutenyl succinic anhydride is prepared by the reaction of a chlorinated polyisobutylene with maleic anhydride at 200 C. The polyisobutenyl radical has an average molecular weightof 850 and the resulting alkenyl succinic anhydride is found to have an acid number of 113 (corresponding to an equivalent weight of 500). To a mixture of 500 grams (1 equivalent) of this polyisobutenyl succinic anhydride and 160 grams of toluene there is added at room temperature 35 grams (1 equivalent) of diethylene triamine. The addition is made portionwise throughout a period of 15 minutes, and an initial exothermic reaction caused the temperature to rise to 50 C. The mixture then is heated and a Watertoluene azeotrope distilled from the mixture. When no more water would distill the mixture is heated to 150 C. at reduced pressure to remove the toluene. The residue is diluted with 350 grams of mineral oil and this solution is found to have a nitrogen content of 1.6%.
Example 2 V The procedure of Example 1 is repeated using 31 grams (1 equivalent) of ethylene diamine as the amine reactant. The nitrogen content of the resulting product is 1.4%.
Example 3 The procedure of Example 1 is repeated using 55.5 grams (1.5 equivalents) of an ethylene amine mixture having a composition corresponding to that of triethylene tetramine. The resulting product has a nitrogen content of 1.9%.
V 7 Example 4 The procedure of Example 1 is repeated using 55.0
grams (1.5 equivalents) of triethylene tetramine as the amine reactant. content of 2.9%
The resulting product has a nitrogen Example 5 amine mixture having an average composition corresponding to that of tetraethylene pentamine. The mixture is heated to distill the water-toluene azeotrope and then to 150 C. at reduced pressure to remove the remaining toluene. The residual polyamide has a nitrogen content of 4.7%.
Example 6 The procedure of Example 1 is repeated using 46 grams 1.5 equivalents) of ethylene diamine as the amine reactant. The product which resulted has a nitrogen content of 1.5%.
Example 7 A polyisobutenyl succinic anhydride having an acid number of and an equivalent weight of 540 is prepared by the reaction of a chlorinated polyisobutylene (having an average molecular weight of 1,050 and a chlorine content of 4.3%) and maleic anhydride. To a mixture of 300 parts by weight of the polyisobutenyl succinic anhydride and 160 parts by weight of mineral oil there is added at 65-95 C. an equivalent amount (25 parts by weight) of the commercial ethylene amine mixture of-Example 5. This mixture then is heated to 150 C. to distill all of the Water formed in the reaction. Nitrogen is bubbled through the mixture at this temperature to insure removal of the last traces of water. The residue is diluted by 79 parts by weight of mineral oil and this oil solution found to have a nitrogen content of 1.6%.
Example 8 A mixture of 2,112 grams (3.9 equivalents) of the polyisobutenyl succinic anhydride of-Example 7, 136 grams (3.9 equivalents) of diethylene triamine, and 1060 grams of mineral oil is heated at 140150 C. for one hour. Nitrogen is bubbled through the mixture at this temperature for four more hours to aid in the removal of water. The residue is diluted with 420 grams of min- .eral oil and this oil solution is found to have a nitrogen content of 1.3%
Example 9 To a solution of 1,000 grams (1.87 equivalents) of the polyisobutenyl succinic anhydride of Example 7, in 500 grams of mineral oil there is added at 85-95 C. 70 grams (1.87 equivalents) of tetraethylene pentarnine. The mixture then is heated at -165 C. for four hours, blowing with nitrogen to aid in the removal of Water. The residue is diluted with 200 grams of mineral oil and the oil solution found to have a nitrogen content of 1.4%.
Example 10 A polypropenyl succinic anhydride is prepared by the reaction of a chlorinated polypropylene (having a molecular weight of about 900 and a chlorine content of 4%) and maleic anhydride at 200 C. The product has an acid number of 75. To a mixture of 390 grams (0.52 equivalent) of this polypropenyl succinic anhydride, 500 grams of toluene, and grams of mineral oil there is added portionwise 22 grams (0.52 equivalent) the commercial ethylene amine mixture of Example 5. The reaction mixture is heated at reflux temperature for three hours and water removed from an azeotrope with toluene. The toluene then is removed by heating to 150 C./20 millimeters. The residue was found to contain 1.3% of nitrogen.
Example 11 A substituted succinic anhydride is prepared by reacting maleic anhydride with a chlorinated copolymer of isobutylene and styrene. The copolymer consists of 94 parts by weight of isobutylene units and 6 parts by weight of the commercial ethylene amine mixture of Example 5. The mixture is heated at reflux temperature for three hours to remove by azeotropic distillation all of the water formed in the reaction, and then at 150 C./20 millimeters to remove the toluene. The residue contains 1.1% by weight of nitrogen.
Example 12 A substituted succinic anhydride is prepared by reacting maleic anhydride with a chlorinated copolymer of isobutylene and isoprene. The copolymer consists of 99 parts by weight of isobutylene units and 1% by weight of isoprene units. The molecular Weight of the copolymer is 28,000 and the chlorine content of the chlorinated copolyrner is 1.95%. The resulting alkenyl succinic anhydride had an acid number of 54. To a mixture of 228 grams (0.22 equivalent) of an oil solution of this alkenyl succinic anhydride, 58 grams of additional mineral oil, 500 grams of toluene and 9.3 grams (0.22 equivalent) of the commercial ethylene amine mixture of Example 5 is heated at 110120 C. for three hours, water being re moved from an azeotrope with toluene. When all of the water has thus been removed the toluene is distilled by heating to 150 C./ 20 millimeters. The residue is found to have a nitrogen content of 1.1%.
Example 13 A polyisobutenyl succinic anhydride is prepared by the reaction of a chlorinated polyisobutylene with maleic anhydride. The chlorinated polyisobutylene has a chlorine content of 2% and an average molecular weight of 11,000. The polyisobutenyl succinic anhydride has an acid number of 48. A mixture of 410 grams (0.35 equivalent) of this anhydride, grams (0.35 equivalent) of the commercial ethylene amine mixture of Example 5 and 500 grams of toluene is heated at reflux temperature for four hours to remove water from an azeotrope with toluene. The toluene then is removed by heating to 150 C./ millimeters. The nitrogen content of the residue is 1.3%.
Example 14 The procedure of Example 5 is repeated except that 0.94 equivalent of the amine is used instead of 1.55 equivalents. The nitrogen content of the product is 3%.
Example 15 A polyisobutenyl-substituted succinic acid is prepared by hydrolysis of the corresponding anhydride (prepared in turn by the condensation of a chlorinated polyisobutylene and maleic anhydride). To 1152 grams (1.5 equivalents) of a 70% mineral oil solution of this polyisobutenyl succinic acid having an acid number of 62 there is added at room temperature 59.5 grams (1.5 equivalents) of the commercial ethylene amine mixture of Example 5. This mixture is heated at 150-167 C. for 7 hours during which time a total of 19.5 grams of water is distilled from the mixture. The residue is diluted with 174 grams of mineral oil and then filtered at 150 C. The filtrate has a nitrogen content of 1.6%.
Example 16 A mixture of 1056 grams (2.0 equivalents) of the polyisobutenyl succinic anhydride of the preceding example (in which the polyisobutenyl group has a molecular Weight of 850), 89 grams (2.0 equivalents) of di-(1,2-propylene)- triamine (having a nitrogen content of 31.3%), 370 grams of mineral oil and 100 grams of toluene is heated at reflux temperature (180l90 C.) for 5 hours. A total of 18 grams of Water is collected from the water-toluene azeotrope. The residue is heated to 150 C./20 mm. to remove any last traces of water which might have remained. The nitrogen analysis of this residue is 1.9%.
Example 17 A polyisobutylene having an average molecular Weight 10 of 50,000 is chlorinated to a chlorine content of 10% by weight. This chlorinated polyisobutylene is reacted with maleic anhydride to produce the corresponding polyisobutenyl succinic anhydride having an acid number of 24. To 6,000 grams (2.55 equivalents) of this anhydride there is added portionwise at 70105 C. 108 grams (2.55 equivalents) of the commercial ethylene amine mixture of Example 5 over a period of 45 minutes. The resulting mixture is heated for four hours at 160-180 C. While nitrogen is bubbled throughout to remove water. When all of the water has been removed the product is filtered and the filtrate found to have a nitrogen content of 0.6%
Example 18 A mixture of 1 equivalent of a polyisobutene-substituted succinic anhydride having an acid number of 98 (prepared according to the procedure described in Example 1) and 1 equivalent of an acrolein-ammonia (molar ratio of 1:1) interpolymer having a nitrogen content of 23% by weight is diluted with 40% by its weight of a mineral oil. The resulting mixture is heated to 155 C. and nitrogen is bubbled through the mixture at this temperature for 5 hours. The residue is found to have a nitrogen content of 1.35%.
Example 19 A cyanoethyl-substituted ethylene amine is prepared by mixing 212 grams of acrylonitrile with 216 grams of an ethylene amine mixture consisting of 75% by weight of triethylene tetramine and 25% by Weight of diethylene triamine at room temperature and heating the mixture at 110130 C. for 5 hours and then to C./30 mm. To a mixture of 1110 grams of the polyisobutene-substituted succinic anhydride of Example -1 and 825 grams of mineral oil there is added at 60 C. 143 grams dropwise of the above cyanoethyl-substituted ethylene amine (having a nitrogen content of 31.8%). The mixture is heated at 160 C. for 5 hours while being purged with nitrogen. A total of 6 cc. of water is removed by distillation. The residue has a nitrogen content of 1.66%.
Example 20 To a mixture of 430 grams of the polyisobutene-substituted succinic anhydride of Example 1 and 355 grams of mineral oil there is added at 60-80 C. 108 grams of N-aminopropyl morpholine throughout a period of 1 hour. The mixture is heated at 150155 C. for 5 hours until no more distills. The residue is found to have a nitrogen content of 2.3%.
Example 21 To a mixture of 430 grams of the polyisobutene-substituted succinic anhydride of Example 1 and 304 grams of mineral oil there is added at 60-80 C. 33 grams of dipropylene triamine. The mixture is then heated at 150 C. for 5 hours until no more water distills. The residue is found to have a nitrogen content of 1.45%.
Example 22 To a mixture of 1000 grams of the polyisobutene-substituted succinic anhydride of Example 1 and 500 grams of mineral oil there is introduced at 150-160 C. beneath its surface a sufiicient quantity of ammonia for formation of an imide Within a period of 1 hour. The mixture is diluted with 169 grams of mineral oil, heated to 150 C. and filtered. The filtrate is found to have a nitrogen content of 0.77%.
Example 23 A mixture of 286 grams of polyisobutene-substituted succinic anhydride of Example 1, 96 grams of N,N-dibu-tyl ethylene diamine and 252 grams of mineral oil is prepared at 60 C. and heated at 150l65 C. for 5 hours while being purged with nitrogen. The residue is found to have a nitrogen content of 2.24%.
1 1 Example 24 A mixture of 41 7 grams of polyisobutene-substituted succinic anhydride of Example 1, 30 grams of N-(2- aminoethyl) trimethylene diamine and 293 grams of mineral oil is prepared at 60 -80 C. for 5 hours while being purged with nitrogen. The residue is found to have a nitrogen content of 1.51.
Example 25 A mixture of 430 grams of the polyisobutene-substituted succinic anhydride of Example 1, 64 grams of 1,1- (dimethylaminoethyl)-4-methyl-piperazine and 324 grams of mineral oil is prepared at 60 C. and then heated at 150-155 C. while being blown with nitrogen. The residue is found to have a nitrogen content of 1.81%.
Example 26 A mixture of 416 grams of polyisobutene-substituted succinic anhydride of Example 1, 124 grams of N-phenyl piperazine and 356 grams of mineral oil is prepared at 60 C. and then heated at ISO-155 C. for 5 hours while being purged with nitrogen. No water is removed by such heating. The residue is found to have a nitrogen content of 2.07%.
Example 27 A mixture of 1110 grams of polyisobutene-substituted succinic anhydride of Example 1, 105 grams of anthranilic acid and 844 grams of mineral oil is heated at 100 C. for 2 hours. The mixture is cooled and is mixed with 72 grams of a mixture consisting of 75% by weight of triethylene tetramine and 25% by weight of diethylenetriamine at 6080 C. The resulting mixture is heated at 150-155 C. for 5 hours while being purged With nitrogen. The residue is found to have a nitrogen content of 1.72%.
Example 28 A diisobutenyl-substituted ethylene amine is prepared by reacting 590 grams of diisobutenyl chloride and 264 grams of a mixture consisting of 75% by Weight of tri ethylene tetramine and 20% by Weight of diethylene triamine in the presence of 264 grams of potassium hydroxide (85% purity) and 2200 grams of isopropyl alcohol at 8590 C. A mixture of 528 grams of polyisobutene-substituted succinic anhydride of Example 1, 101 grams of the above diisobutenyl-substituted ethylene amine and 411 grams of mineral oil is heated at 150- 160 C. while being purged with nitrogen until no more water distills. The residue has a nitrogen content of 1.98%.
Example 29 A mixture of 45 grams of di-(polypropoxy)cocoamine having a molecular weight of 2265, 22 grams of polyisobutene-substituted succinic anhydride of Example 1 and 44 grams of mineral oil is heated at 150-155 C. for 7 hours. The residue is found to have a nitrogen content 'of 0.25%.
Example 30 A mixture of 1000 grams of the polyisobutene-substituted succinic anhydride of Example 1, 159 grams of menthane diarnine and 5 00 grams of mineral oil is prepared at 70100 C. and heated at 150-490 C. while being blown with nitrogen until no water distills. The residue is diluted with 258 grams of mineral oil and the solution is found to have a nitrogen content of 1.32.
Example 31 A polypropylene-substituted succinic anhydride having an acid number of 84 is prepared by the reaction of a chlorinated polypropylene having a chlorine content of 3% and molecular Weight of 1200 with maleic anhydride. A mixture of 813 grams of the polypropylene-substituted succinic anhydride, 50 grams of a commercial ethylene amine mixture having an average composition corre- 12 sponding to that of tetraethylene pentamine and 566 grams of mineral oil is heated at 150 C. for 5 hours. The residue is found to have a nitrogen content of 1.18%.
Example 32 A mixture of 206 grams of N,N'-disecondary-buty1 p-phenylene diamine, 1000 grams of the polyisobutenesubstituted succinic anhydride of Example 1 and 500 grams of mineral oil is prepared at 85 C. and heated at 150-200 C. for 9.5 hours. The mixture is diluted with 290 grams of mineral oil, heated to 160 C. and filtered. The filtrate is found to have a nitrogen content of 1.29%.
Example 33 ene pentamine at 70 80 C. The mixture is then heated at 150-160 C. While being purged with nitrogen until no more water is removed by distillation. The residue is diluted with 200 grams of mineral oil, heated to 160 C. and filtered. The filtrate has a nitrogen content of 1.16%.
Example 34 To a solution of 1000 grams of the polyisobutene-substituted succinic anhydride of Example 1 in 500 grams of mineral oil there is added 28 grams of 1,1-dimethyl hydrazine at 5060 C. The mixture is heated at 6095 C. for 3 hours and then mixed with 40 grams of an ethylene amine mixture having an average composition corresponding to that of tetraethylene pentamine at 95 C. The mixture is then heated at 150-485 C. for 6 hours whereupon 14 grams of water is collected as the distillate. The residue is diluted with 197 grams of mineral oil, heated to 160 C. and filtered. The filtrate has a nitrogen content of 1.53%.
Example 35 A mixture of 1000 grams of the polyisobutene-substituted succinic anhydride of Example 1, 333 grams of 1,2-di(3-aminopropoxy) ethane and 500 grams of mineral oil is heated at -170 C. for 5 hours whereupon 18 grams of water is collected as the distillate. The residue is diluted with 380 grams of mineral oil, heated to 160 C. and filtered. The filtrate has a nitrogen content of 2.3%.
Example 36 A mixture of 1000 grams of the polyisobutene-substL tuted succinic anhydride of Example 1, 418 grams of di(3-aminopropoxy ethyl) ether and 500 grams of mineral oil is heated at -170 C. for 4 hours. A total of 17 grams of water is collected as the distillate. The residue is diluted with 433 grams of mineral oil heated to 160 C. and filtered. The filtrate has the nitrogen content of 2.18%.
Example 37 A mixture of 1000 grams of the polyisobutene-substituted succinic anhydride of Example 1 and 361 grams of a technical tertiary-alkyl primary amine wherein the tertiary-alkyl radical contains 1214 carbon atoms and 500 grams of mineral oil is heated at -250 C. for 13 hours while being urged with nitrogen. The reisdue is then heated to 150 C./1 mm., diluted with 337 grams of mineral oil, heated to C. and filtered. The filtrate has a nitrogen content of 0.87%.
Example 38 A mixture of 1000 grams of the polyi-sobutene-substi tuted succinic anhydride of Example 1, 254 grams of aminoguanidine bicarbonate and 500 grams of mineral 13 oil is prepared at 80 C. and heated at 130-165 C. for hours. The residue is mixed with 223 grams of mineral oil, heated to 150 C., and filtered. 'The filtrate has the nitrogen content of 338%.
Example 39 A mixture of 1000 grams of the polyisobutene-substituted succinic anhydride of Example 1, 178 grams of 2-amino pyridine and 500 grams of mineral oil is heated at 140-175 C. for hours while being purged with nitrogen. A total of 16 grams of water is collected as the distillate. The residue is diluted wtih 273 grams of mineral oil and filtered. The filtrate has a nitrogen content of 2.55%.
Example 40 A mixture of 1000 grams of the polyisobutene-substituted succinic anhydride of Example 1, 103 grams of 2,6- di-amino-pyridine and 500 grams of mineral oil is heated at 140-180 C. for 11 hours while being purged with nitrogen. A total of 16 grams of water is collected as the distillate. The residue is diluted with 223 grams of mineral oil, heated to 150 C. and filtered. The filtrate has a nitrogen content of 2.15%.
Example 41 A mixture of 1000 grams of polyisobutene-substituted succinic anhydride of Example 1 159 grams of cyanoguanidine and 233 grams of toluene is heated at the reflux temperature for 14 hours while 7.15 grams of water is removed by azeotropic distillation. The mixture is diluted with 740 grams of mineral oil and toluene is then removed by heating the mixture to 150 C. The residue is filtered and the filtrate has the nitrogen content of 4.74%.
Example 42 A mixture of 1632 grams of polyisobutene-substituted succinic anhydride of Example 1 207 grams of a condensation product of acrolein with ammonia (molar ratio of 1:1) having a nitrogen content of 604 grams of mineral oil and 1750 grams of toluene is heated at the reflux temperature for 3 hours. A total of 31 grams of water is removed as the distillate. Toluene is then removed by heating the mixture to 150 C./20 mm. The residue is found to have a nitrogen content of 1.89%.
Example 43 A nitrogen-containing compound is prepared by mixing 100 grams of cyanoguanidine with 500 grams of ethylene amine mixture having an average composition corresponding to that of tetraethylene pentamine and heating the mixture at 7080 C. for 3 hours to obtain a homogeneous mass and filtering the mass. A mixture of 1000 grams of the polyisobutene-substituted succinic anhydride of Example 1 96 grams of the above filtrate and 164 grams of toluene is heated at the reflux temperature for 10 hours. Toluene is then removed by heating the mixture to 150 C./ 20 mm. The residue is diluted with 400 grams of mineral oil and filtered. The filtrate has a nitrogen content of 3.43%.
Example 44 To a mixture of 544 grams of the polyisobutene-substituted succinic anhydride of Example 1 283 grams of mineral oil and 281 grams of toluene there is added 30 grams of urea at 45 C. The resulting mixture is heated at l30-135 C. for 11 hours whereupon 2.5 cc. of water is removed as the distill-ate. The residue is then heated to 140 C./ 20 mm. and filtered. The filtrate has a nitrogen content of 1%.
Example 45 A mixture of 1088 grams of the polyisobutene-substituted succinic anhydride of Example 1, 106 grams of dipropylene triamine, 500 grams of toluene is heated at the reflux temperature for 4 hours until no more water distills. The residue is then heated to 150 C./ 20 mm. and
diluted with 392 grams of mineral oil. The oil solution is found to have a nitrogen content of 1.74%.
Example 46 A mixture of 1000 grams of the polyisobutane-substituted succinic anhydride of Example 1, 174 grams of phenylbiguanide and 270 grams of toluene is heated at the reflux temperature for 6.5 hours whereupon 25 grams of water is removed by distillation. The residue is diluted with 500 grams of mineral oil and heated to C./20 mm. to distill off toluene. The-residue is diluted further with 265 grams of mineral oil, heated to 150 C. and filtered. The filtrate has a nitrogen content of 3.4%.
Example 47 A mixture of 920 grams of the polyisobutene-substituted succinic anhydride of Example 1, and 249 grams of bis-(dimethylaminopropyl)amine is heated at the reflux temperature until no more water distills. The residue has a nitrogen content of 4%.
Example 48 A mixture of 1000 grams of the polyisobutene-substituted succinic "anhydride of Example 1, 363 grams of aminopropyl octadecylamine and 1314 grams of mineral oil is heated at 2000 C. for 24 hours. The residue is filtered. The filtrate has a nitrogen content of 1.02%.
Example 49 A mixture of 1000 grams of the polyisobutene-sub-stituted succinic anhydride of Example 1, and 258 grams of di-n-butylamine is heated at C. for 12 hours and then to 200 C./ 25 mm. The residue is diluted with 1157 grams of mineral oil and filtered. The filtrate has a nitrogen content of 0.8%.
Example 50 A mixture of 297 grams of the polyisobutene-substituted succinic anhydride of Example 1, 25 grams of melamine and 200 grams of mineral oil is heated at 250 C. for 9 hours and then at 290295C. for 7 more hours. The residue is mixed with 50 grams of water, heated at reflux for 7 hours, dried and filtered.
The filtrate has a nitrogen content of 2%.
Example 51 A mixture of 100 grams of the polyisobutene-substituted succinic anhydride of Example 1 and 67 grams of mineral oil is heated to 50C. To this mixture there is added 59 grams of a 85% aqueous solution of hydrazine hydrate. The mixture is heated at 100 1l0 C. for 1.25 hours, diluted with toluene, and heated at 107 C. until no more water distills. Toluene is removed by distillation. The residue has a nitrogen content of 0.8%.
Example 52 A product is obtained by the procedure of Example 1, except that pyrrolidine (1 equivalent) is used in lieu of the diethylene triamine used.
Example 54 A product is obtained by the procedure of Example 1, except that hexahydro-1,3,5-triazine (1 equivalent) is used in lieu of the diethylene triamine used.
was heated at 180-276 C./40 mm. for 14.5 hours.
15 Example 55 A product is obtained by the procedure of Example 1, except that 1,3,4-dithi-azolidine (1 equivalent) is used in lieu of the diethylene triamine used.
Example 56 A product is obtained by the procedure of Example 1, except that hexamethylene tetramine (2 equivalents) is used in lieu of the diethylene triamine used.
Example 5 7 A product is obtained by the procedure of Example 1, except that tripentylene tetramine (3 equivalents) is used in lieu of the diethylene triamine used.
Example 58 An equi-mol'ar mixture of the polyisobutene-substituted succinic anhydride of Example 1 :and N-octyl thiourea is diluted with an equal volume of xylene. The resulting mixture is heated at the reflux temperature :for 30 hours. The residue is a xylene solution of the product.
Example 59 A product is obtained by the procedure of Example 58 except that oleylamide is used in lieu of the thiourea used.
Example 60 A product is obtained by the procedure of Example 58 except that 1,3-diphenyl guanidine is used in lieu of the thiourea used.
Example 61 A product is obtained by the procedure of Example 58 except that octadecamidine is used in lieu of the thiourea used.
Example 62 A product is obtained by the procedure of Example 58 except that 'guanylurea is used in lieu of the thiourea used.
Example 63 To a mixture of 396 grams of the polyisobutene-substituted succinic anhydride of Example 1 and 282 grams of mineral oil there was added 34 grams of N-methyltrimethylene diamine at 60 C. within a period of one hour. The mixture was blown with nitrogen at 150- 155 C. for 5 hours. The residue was found to have a nitrogen content of 1.41%.
Example 64 A mixture of 386 grams of mineral oil, 528 grams of the polyisobutene-substituted succinic anhydride of Example 1, and 59 grams of N-(Z-hydroxyethyl) -trimethylenediamine was prepared at 60 C. The mixture was blown with nitrogen at 150-155 C. for 5 hours. The residue had a nitrogen content of 1.56%.
Example 66 A mixture of 185 grams of mineral oil, 330 grams of the polyisobutene-substituted succinic anhydride of Example 1, and 88.5 grams of 1,4-bis(2-hydroxypropyl)-2- methyl piperazine was prepared at 60 C. The mixture The residue has a nitrogen content of 1.12%.
1 6 Example 67 To a mixture of 314 grams of mineral oil and 430 grams of the polyisobutene-substituted succinic anhydride of Example 1 there was added at 60 C., 49 grams of 1-(2-hydroxyethyl) piperazine. The mixture was heated to C. and blown with nitrogen at this temperature for 5 hours. The residue had a nitrogen content of 1.38%.
Example 68 A mixture of 382 grams of mineral oil, 528 grams of the polyisobutene-substituted succinic anhydride of Example 1, and 53 grams of 14nethyl-4-(3-a-minopropyl) piperazine was prepared at 6 0 C., heated to 150 C., and blown with nitrogen at 150-155 C. for 5 hours. The residue has a nitrogen content of 1.57%.
Example 69 To a mixture of 800 grams of the polyisobutene-substituted succinic anhydride of Example 1 and 175 grams of toluene there was added 77 'grams of a commercial mixture of alkylene amines and hy-droxy alkyl-substituted alkylene amines consisting of approximately 2% (by weight) of diethylene triamine, 36% of 1-(2-aminoethyl)- piperazine, 11% of 1-(2-hydroxyethyl)piperazine, 11% of N-(2 hydroxyethyl)ethylenediamine, and 40% of higher homologues obtained as a result of condensation of the above-indicated amine components. The resulting mixture was heated at the reflux temperature for 16.5 hours whereupon 12 cc. of water was collected as the distillate. The residue was then heated to C./25 mm. and diluted with 570 grams of mineral oil. The final product was found to have a nitrogen content of 1.57%.
Example 70 A product is obtained by the procedure of Example 58 except that an equimolar mixture of ammonia and bis(2-hydroxyethyl)amine is used in lieu of the thiourea used.
Example 71 A product is obtained by the procedure of Example 58 except that benzidine is used in lieu of the thiourea used.
Example 72 An acylated nitrogen composition is prepared according to the procedure of Example 1 except that the reaction mixture consists of 3880 grams of the polyisobutcnyl succinic anhydride, 376 grams of a mixture of triethylene tetramine and diethylene triamine (75:25 weight ratio), and 2785 grams of mineral oil. The product is found to have a nitrogen content of 2%.
Example 73 Example 74 An acylated nitrogen composition is prepared according to the procedure of Example 31 except that the polyisobutene-substituted succinic anhydride of Example 1 (1 equivalent for 1.5 equivalents of the amine reactant) is substituted for the polypropylene-substituted succinic anhydride used.
Example 75 An acylated nitrogen composition is prepared according to the procedure of Example 31 except that the polyisobutene-substituted succinic anhydride of Example 1,
(1 equivalent for 2 equivalents of the amine reactant) is substituted for the polypropylene-substituted succinic anhydride used.
1 7 Example 76 An acylated nitrogen composition is prepared according to the procedure of Example 4 except that the commercial ethylene amine mixture (1.5 equivalent per equivalent of the anhydride) of Example 7 is substituted for the triethylene tetramine used.
Example 77 An acylated nitrogen composition is prepared according to the procedure of Example 31 except that the polyisobutene-substituted succinic anhydride of Example 1 (1 equivalent for 1 equivalent of the amine reactant) is substituted for the polypropylene-substituted succinic anhydride. The composition is found to have a nitrogen content of 1.5%.
The boron compounds useful in reaction with the acylated nitrogen compositions include boron oxide, boron oxide hydrate, boron trifiuoride, boron tribromide, boron trichloride, boron acids such as boronic acid (e.g., alkyl- B(OH) or aryl-B(OH) boric acid (i.e., H BO tetraboric acid (i.e., H B O metaboric acid (i.e. HBO and esters of such boron acids. The use of complexes of a boron trihalide with ethers, organic acids, inorganic acids, or hydrocarbons is a convenient means of introducing the boron reactant into the reaction mixture. Such complexes are known and are exemplified by boron-trifiuoride-diethyl ester, boron trifluoride-phosphoric acid, boron trichloride-chloroacetic acid, boron tribromide-dioxane, and boron trifluoride-methyl ethyl ether.
Specific examples of boronic acids include methyl boronic acid, phenyl-boronic acid, cyclohexyl boronic acid, p-heptylphenyl boronic acid and dodecyl boronic acid.
The boron acid esters include especially mono-, di-, and tri-organic esters of boric acid with alcohols or phenols such as, e.g., methanol, ethanol, isopropanol, cyclohexanol, cyclopentanol, l-octanol, 2-octanol, dodecanol, behenyl alcohol, oleyl alcohol, stearyl alcohol, benzyl alcohol, 2- butyl cyclohexanol, ethylene glycol, propylene glycol, trimethylene glycol, 1,3-butanediol, 2,4-hexanediol, 1,2- cyclohexanediol, 1,3-octanediol, glycerol, pentaerythritol diethylene glycol, carbitol, Cellosolve, triethylene glycol, tripropylene glycol, phenol, naphthol, p-butylphenol, o,pdiheptylphenol, n-cyclohexylphenol, 2,2-bis-(p-hydroxyphenyl) propane, polyisobutene (molecular weight of 1500)-substituted phenol, ethylenechlorohydrin, o-chlorophenol, m-nitrophenol, 6-bromo-octanol, and 7-keto-decanol. Lower alcohols, 1,2-glycols, and 1-3-glycols, i.e., those having less than about 8 carbon atoms are especially useful for preparing the boric acid esters for the purpose of this invention.
Methods for preparing the esters of boron acid are known and disclosed in the art (such as Chemical Reviews, pages 959-1064, volume 56). Thus, one method involves the reaction of boron trichloride with 3 moles of an alcohol or a phenol to result in a tri-organic borate. Another method involves the reaction of boric oxide with an alcohol or a phenol. Another method involves the direct esterification of tetra boric acid with 3 moles of an alcohol or a phenol. Still another method involves the direct esterification of boric acid with a glycol to form, e.g., a cyclic alkylene borate.
The reaction of the acylated nitrogen compositions with the boron compounds can be effected simply by mixing the reactants at the desired temperature. The use of an inert solvent is optional although it is often desirable, especially when a highly viscous or solid reactant is present in the reaction mixture. The inert solvent may be a hydrocarbon such as benzene, toluene, naphtha, cyclohexane, n-hexane, or mineral oil. The temperature of the reaction may be varied within wide ranges. Ordinarily it is preferably between about 50 C. and about 250 C. In some instances it may be 25 C. or even lower. The upper limit of the temperature is the decomposition point of the particular reaction mixture.
The reaction is usually complete within a short period 18 such as 0.5 to 6 hours. After the reaction is complete, the product may be dissolved in the solvent and the resulting solution purified by centrifugation or filtration if it appears to be hazy or contain insoluble substances. Ordinarily the product is sufiiciently pure so that further purification is unnecessary or optional.
The reaction of the acylated nitrogen compositions with the boron compounds results in a product containing boron and substantially all of the nitrogen originally present in the nitrogen reactant. It is believed that the reaction results in the formation of a complex between boron and nitrogen. Such complex may involve in some instances more than one atomic proportion of boron with one atomic proportion of nitrogen and in other instances more than one atomic proportion of nitrogen with one atomic proportion of boron. The nature of the complex is not clearly understood. Evidence appears to indicate that the complex results from a direct linkage between boron and nitrogen and that in most instances, the radicals originally present in the boron and the nitrogen atoms do not take part directly in the complex formation. However, in the case of a boron acid as the reactant, the reaction is often accompanied with the formation of water.
Inasmuch as the precise stoichiometry of the complex formation is not known, the relative proportions of the reactants to be used in the process are based primarily upon the consideration of utility of the products for the purposes of this invention. In this regard, useful products are obtained from reaction mixtures in which the reactants are present in relative proportions as to provide from about 0.1 atomic proportions of boron for each mole of the acylated nitrogen composition used to about 10 atomic proportions of boron for each atomic proportion of nitrogen of said acylated nitrogen composition used. The preferred amounts of reactants are such as to provide from about 0.5 atomic proportion-of boron for each mole of the acylated nitrogen composition to about 2 atomic proportions of boron for each atomic proportion of nitrogen used. To illustrate, the amount of a boron compound having one boron atom per molecule to be used with one mole of an acylated nitrogen composition having five nitrogen atoms per molecule is within the range from about 0.1 mole to about 50 moles, preferably from about 0.5 mole to about 10 moles.
The following examples are illustrative of the process for preparing the nitrogenand boron-containing compositions of this invention.
Example A To 600 grams (1 atomic proportion of nitrogen) of the acylated nitrogen composition prepared according to the process of Example 77 there is added 45.5 grams (0.5 atomic proportion of boron) of boron trifiuoridediethyl other complex (1:1 molar ratio) at 60-75 C. The resulting mixture is heated to 103 C. and .then at C./30 mm. to distill 011 all volatile components. The residue is found to have a nitrogen content of 1.44% and a boron content of 0.49%.
Example B A mixture of 62 grams (1 atomic proportion of boron) of boric acid and 1645 grams (2.35 atomic proportions of nitrogen) of the acylated nitrogen composition obtained by the process of Example 72 is heated at C. in nitrogen atmosphere for 6 hours. The mixture is then filtered and the filtrate is found to have a nitrogen content of 1.94% and a boron content of 0.33%.
Example C An oleyl ester of boric acid is prepared by heating an equi-molar mixture of oleyl alcohol and boric acid in toluene at the reflux temperature while water is removed azeotropically. The reaction mixture is then heated to 150 C./20 mm. and the residue is the ester having a boron content of 3.2% and a saponification number of 62. A mixture of 344 grams (1 atomic proportion of boron) of the ester and 1645 grams (2.35 atomic proportions of nitrogen) of the acylated nitrogen composition obtained by the process of Example 72 is heated at 150 C. for 6 hours and then filtered. The filtrate is found to have a boron content of 0.6% and a nitrogen content of 1.74%.
Example D A mixture of 344 grams (1 atomic proportion of boron) of the oleyl ester of boric acid of Example C and 1112 grams (2.86 atomic proportions of nitrogen) of the acylated nitrogen composition obtained by the proc-' ess of Example 73 is heated at 150 C. for 6 hours and filtered. The filtrate is found to have a nitrogen con tent of 1.94% and a boron content of 0.81%.
Example E Tri-isobutylborate is prepared by heating a mixture of 620 grams moles) of boric acid, 2220 grams (30 moles) of isobutyl alcohol, and 800 grams of toluene at the reflux temperature while water formed during esterifi cation is being removed by azeotropic distillation. The reaction mass is then heated at 100 C./20 mm. to distill off toluene and the borate is recovered by distillation at 105 -1 10 C./20 mm. The distillate is found to have a boron content of 5.2%. A mixture of 57 grams (0.27 atomic proportion of boron), 13 grams of mineral oil, and 1045 grams (1.56 atomic proportions of nitrogen) of the product obtained by the process of Example 74 is heated at 150-160 C. for 3 hours and then blown with nitrogen at 170 C. (no volatile substance is formed). The mixture is then heated to 150 C./20 mm. and the residue is found to have a boron content of 0.39% and a nitrogen content of 1.98%.
Example F Boron trifiuoride (34 grams, 0.5 atomic proportion of boron) is bubbled into 1400 grams (1.5 atomic proportion of nitrogen) of the product prepared according to the process of Example 77 at 80 C. within a period of 3 hours. The resulting mixture is blown with nitrogen at 70-80 C. for 2 hours and diluted with 23 grams of mineral oil. The residue is found to have a boron content of 0.42%, a fluorine content of 1.58%, and a nitrogen content of 1.41%.
Example G A mixture of 31 grams (0.5 atomic proportion of boron) of boric acid and 1175 grams (1.75 atomic proportions of nitrogen) of the acylated nitrogen composition prepared by the process of Example 74 is heated at 150 C. for 3 hours and filtered. The filtrate is found to have a boron content of 0.43% and a nitrogen content of 1.85%.
Example H A complex of phosphoric acid with 3 moles of boron trifiuoride (67.3 grams, 0.62 atomic proportion of boron) is added dropwise to amixture of 1344 grams (1.92 atomic proportions of nitrogen) of the acylated nitrogen composition of Example 74 and 432 grams of mineral oil. An exothermic reaction occurs. The mixture is heatedat 80-90 C. for 0.5 hour and mixed with 520 cc. of benzene. The resulting solution is washed with, successively, 500 cc. of water, a mixture of 500 cc. of water and 250 cc. of isopropyl alcohol, 50 cc. of a saturated sodium chloride solution, and a mixture of 750 cc. of water and 250 cc. isopropyl alcohol. The washed product is heated to 150 C./38'-68 mm. within a period of 6 hours, cooled, and filtered. The filtrate is found to have a nitrogen content of 1.34% and a boron content of 0.1%.
. Example I A mixture of 12 grams (0.38 mole) of sulfur, 124
20 grams (2 atomic proportions of boron) of boric acid, and 1018 grams (2 atomic proportions of nitrogen) of the acylated nitrogen composition of Example 75 is heated at 150 C. for 3 hours and filtered. The filtrate is found to have a nitrogen content of 2.4%, a boron content of 1.68%, and a sulfur content of 0.5%.
Example I The process of Example I is repeated except that thiourea (38 grams, 0.5 mole) is substituted for the sulfur used. The product is found to have a nitrogen content of 3.3%, a sulfur content of 1.44%, and a boron content of 1.75%.
Example K A mixture of 55 grams (0.39 atomic proportion of boron) of boron trifluoride-diethyl ether complex (1:1 molar ratio) and 480 grams (0.77 atomic proportion of nitrogen) of the'product of Example 76 is heated at 80-90 C. for 0.5 hour and then to C./30 mm. The residue is found to have a nitrogen content of 2.08% and a, boron content of 0.76%.
Example L A mixture of 372 (6 atomic proportions of boron) of boric acid and 3111 grams (6'atomic proportions of nitrogen) of the acylated nitrogen composition obtained by the process of Example 75 is heated at C. for 3 hours and then filtered. The filtrate is found to have a boron content of 1.64% and a nitrogen content of 2.56%
Example M Boric acid (124 grams, 2 atomic proportions of boron) is added to the acylated nitrogen composition (556 grams, 1 atomic proportion of nitrogen) obtained ac- "cording to the procedure of Example 75. The resulting mixture is heated at 150 C. for 3.5 hours and filtered at that temperature. The filtrate is found to have a boron compound of 3.23% and a nitrogen content of 2.3%.
Example 0 A mixture of boric acid and the acylated nitrogen composition prepared according to the procedure of Example 17 in relative proportions such as to provide 1 atomic proportion of boron per atomic proportion of nitrogen is diluted with twice its volume of xylene and the resulting mixture heated at 150 C. for 3 hours and filtered. Xylene is removed by heating the filtrate to 150 C./ 0.25 mm. The residue is found to have a boron content of 0.42% and a nitrogen content of 0.44%.
Example P A mixture of boric acid and the acylated nitrogen composition obtained according to the procedure of Example 44 in relative proportions such as to provide 1 atomic proportion of boron per atomic proportion of nitrogen is heated at 150 C. for 3 hours and filtered. The filtrate is found to have a boron content of 0.2%.
Example Q A mixture of boric acid and an acylated nitrogen compositionobtained by the procedure of Example 41 in relative proportions such as to provide 1 atomic proportion of boron per atomic proportion of nitrogen isheated at 21 150 C. for 3 hours and filtered at this temperature. The filtrate is found to have a boron content of 3.1% and a nitrogen content of 4.1%.
Example R A mixture of boron trifiuoride-diethyl ether complex and a polyisobutene-substituted succinimide derived from a polyisobutene having an average molecular weight of 1000 in relative proportions such as to provide 1 atomic proportion of boron per atomic proportion of nitrogen is heated at 150 C. for 3 hours and filtered at this temperature.
Example S A mixture of boric acid and the acylated nitrogen composition obtained by the procedure of Example 37 in relative proportions such as to provide 1 atomic proportion of boron per atomic proportion of nitrogen is heated at 150 C. for 3 hours and filtered.
Example T A mixture of boric acid and the acylated nitrogen composition obtained according to the procedure of Example 25 in relative proportions such as to provide 1 atomic proportion of boron per atomic proportion of nitrogen is heated at 150 C. for 3 hours and filtered.
The nitrogen and boron-containing products of this invention are useful for a wide variety of purposes including pesticides, plasticizers, rust inhibiting agents for treatment of metals, corrosion-inhibiting agents, extreme pressure agents, anti-wear agents, and detergents.
A principal utility of such products is as additives in lubricants. It has been discovered in accordance with this invention that when used for such purpose the effectiveness of the nitrogenand boron-containing products to impart a specific property to a lubricant is closely related to the size of the substantially hydrocarbon substituent in the succinic radical of the acylated nitrogen composition from which such products are derived. More particularly it has been found that products in which the substantially hydrocarbon substitutent contains more than about 50 aliphatic carbon atoms are effective to impart oxidation-inhibiting, corrosion-inhibiting, and detergent properties to a lubricant. It has also been found that the detergent properties of the products diminish sharply vw'th a decrease in the size of the substantially hydrocarbon substituent having less than about 50 aliphatic carbon atoms so that products having less than about 35 aliphatic carbon atoms in this substituent are ineffective as detergent additives in lubricant.
The lubricating oils in which the compositions of this invention are useful as additives may be of synthetic, animal, vegetable, or mineral origin. Ordinarily mineral lubricating oils are preferred by reason of their availability, general excellence, and low cost. For certain applications, oils belonging to one of the other three groups may be preferred. For instance, synthetic polyester oils such as didodecyl adipate and di-Z-ethylhexyl sebacate are often preferred as jet engine lubricants. Normally the lubricating oils preferred will be fluid oils, ranging in viscosity from about 40 Saybolt Universal seconds at 100 F. to about 200 Saybolt Universal seconds at 210 F.
The concentration of the nitrogenand boron-containing compositions as additives in lubricants usually ranges from about 0.1% to about 10% by weight. The optimum concentrations for a particular application depend to a large measure upon the type of service to which the lubricants is to be subjected. Thus, for example, lubricants for use in gasoline internal combustion engines may contain from about 0.5 to about 5% of the additive, whereas lubricating compositions for use in gears in diesel engines may contain as much as or even more of the additive.
This invention contemplates also the presence of other additives in the lubricating compositions. Such additives include, for example, supplemental detergents of the ashcontaining type, viscosity index improving agents, pour point depressing agents, anti-foam agents, extreme pressure agents, rust-inhibiting agents, and supplemental oxidation and corrosion inhibiting agents.
The ash-containing detergents are exemplified by oilsoluble neutral and basic salts of alkali or alkaline earth metals with sulfonic acids, carboxylic acids, or organic phosphorus acids characterized by at least one direct carbon-to-phosphorus linkage such as those prepared by the treatment of an olefin polymer (e.g., polyisobutene having a molecular weight of 1000) with a phosphorizing agent such as phosphorus trichloride, phosphorus heptasulfide, phosphorus pentasulfide, phosphorus trichloride and sulfur, White phosphorus and a sulfur halide, or phosphorothioic chloride. The most commonly used salts of such acids are those of sodium, potassium, lithium, calcium, magnesium, strontium, and barium.
The term basic salt is used to designate the metal salts wherein the metal is present in stoichiometrically larger amounts than the organic acid radical. The commonly employed methods for preparing the basic salts involves heating a mineral oil solution of an acid with a stoichiometric excess of a metal neutralizing agent such as the metal oxide, hydroxide, carbonate, bicarbonate, or sulfide at a temperature about 50 C. and filtering the resulting mass. The use of a promoter in the neutralization step to aid the incorporation of a large excess of metal likewise is known. Examples of compounds useful as the promoter include phenolic substances such as phenol, naphthol, alkylphenol, thiophenol, sulfurized alkylphenol, and condensation products of formaldehyde with a phenolic substance; alcohols such as methanol, 2- propanol, octyl alcohol, Cellosolve, carbitol, ethylene glycol, stearyl alcohol, and cyclohexyl alcohol; amines such as aniline, phenylenediarnine, phenothiazine, phenylbeta-naphthylamine, and dodecylamine. A particularly efiective method for preparing the basic salts comprises mixing an acid with an excess of a basic alkaline earth metal neutralizing agent, a phenolic promoter compound, and a small amount of Water and carbonatin g the mixture at an elevated temperature such as 60-200 C.
Extreme pressure agents and corrosion-inhibiting and oxidation-inhibiting agents are exemplified by chlorinated aliphatic hydrocarbons such as chlorinated Wax; organic sulfides and polysulfides such as benzyl disulfide, bis- (chlorobenzyl) disulfide, dibutyl tetrasulfide, sulfurized sperm oil, sulfurized methyl ester of oleic acid, sulfurized alkylphenol, sulfurized dipentene, and sulfurized terpene; phosphosulfurized hydrocarbons such as the reaction product of a phosphorus sulfide with turpentine or methyl oleate; phosphorus esters including principally dihydrocarbon and trihydrocarbon phosphites such as dibutyl phosphite, diheptyl phosphite, dicyclohexyl phosphite, pentyl phenyl phosphite, dipentyl phenyl phosphite, tridecyl phosphite, distearyl phosphite, dimethyl naphthyl phosphite, oleyl 4-pentylphenyl phosphite, polypropylene (molecular weight 500)-substituted phenyl phosphite, diisobutyl substituted phenyl phosphite; metal thiocarbamates such as zinc dioctyl-dithiocarbamate, and barium heptylphenyl dithiocarbamate: Group II metal phosphorodit-hioates such as zinc dicyclohexylphosphorodithioate, zinc dioctylphosphorodithioate, barium di(heptylphenyl)phosphorodithioate, cadmium dinonylphosphorodithioate, and zinc salt of a phosphorodithioic acid produced by the reaction of phosphorus pentasulfide with an equimolar mixture of isopropyl alcohol and n-hexyl alcohol.
The lubricating compositions may also contain metal detergent additives in amounts usually within the range of about 0.1% .to about 20% by weight. In some applications such as in lubricating marine diesel engines the lubricating compositions may contain as much as 30% of the metal detergent additive. They may also contain extreme pressure addition agents, viscosity in- 23... dex improving agents, and pour point depressing agents, each in amounts within the range from about 0.1% to about 10%.
The following examples are illustrative of the lubricating compositions of this invention (all percentages are by weight):
Example I SAE 20 mineral lubricating oil containing 0.5% of the product of Example A.
Example ll SAE 30 mineral lubricating oil containing 0.75% of the product of Example B and 0.1% of phosphorus as the barium salt of di-n-nonylphosphorodithioic acid.
Example III SAE 10W-30 mineral lubricating oil containing 0.4% of the product of Example C.
Example IV SAE 90 mineral lubricating oil containing 0.1% of the product of Example D and 0.15% of the Zinc salt of an equimolar mixture of di-cyclohexylphosphorodithioic acid and di-isobuty-l phosphorodithioic acid.
Example V SAE 30 mineral lubricating oil containing 2% of the product of Example M.
Example VI SAE 20W-30 mineral lubricating oil containing of the product of Example M.
Example VII SAE W-30 mineral lubricating oil containing 1.5% of the product of Example E and 0.05% of phosphorus as the Zinc salt of a phosphorodithioic acid prepared by the reaction of phosphorus pentasulfide with a mixtur of 60% (mole) of p-butylphenol and 40% (mole) of npentyl alcohol.
Example VIll SAE 50 mineral lubricating oil containing 3% of the product of Example F and 0.1% of phosphorus as the calcium salt of di-hexylphosphorodithioate.
Example IX SAE 10W-30 mineral lubricating oil containing 2% of the product of Example G, 0.06% of phosphorus as zinc di-n-octylphosphorodithioate, and 1% of sulfate ash as barium mahogany sultonate.
Example X SAE 30 mineral lubricating oil containing 5% of the product of Example H, 0.1% of phosphorus as the zinc salt of a mixture of equimolar amounts of di-isopropylphosporodithioic acid and di-n-decylphosphorodithioic acid, and 2.5% of sulfate ash as a basic barium detergent prepared by carbonating at 150 C. a mixture comprising mineral oil, barium di-dodecylbenzene sulfonate and 1.5 moles of barium hydroxide in the presence of a small amount of water and 0.7 mole of octylphenol as the promoter.
Example XI SAE 1OW-30 mineral lubricating oil containing 6% of the product of Example I, 0.075% of phosphorus as zinc di-n-octylphospho-rodithioate, and 5% of the barium salt of an acidic composition prepared by the reaction of 1000 parts of a polyisobutene having a molecular weight of 60,000 with 100 parts of phosphorus pentasulfide at 200 C. and hydrolyzing the product with steam at 150 C.
Example XII SAE 10 mineral lubricating oil containing 2% of the product of Example I, 0.075 of phosphorus as the adduct of zinc di-cyclohexylphosphorodithioate treated with 0.3 mole of ethylene oxide, 2% of a :sulfurized sperm oil having a sulfur content of 10%, 3.5% of a poly-(alkyl methacrylate) viscosity index improver, 0.02% of a poly- (alkyl methacrylate) pour point depressant, 0.003% of a poly-(alkyl siloxane) anti-foam agent.
Example XIII SAE 10 minteral lubricating oil containing 1.5% of the product of Example K, 0.075% of phosphorus as the adduct obtained by heating zinc di-nonylphosphorodithioate with 0.25 mole of 1,2-hexene oxide at 120 C., a sulfurized methyl ester of tall oil acid having a sulfur content of 15%, 6% of a polybutene viscosity index improver, 0.005% of a poly(alkyl methacrylate) anti-foam agent, and 0.5% of lard oil.
Example XIV SAE 10 mineral lubricating oil containing 2% of the product of Example N, 0.07% of phosphorus as zinc dioctylphosphorodithioate, 2% of a barium detergent prepared by neutralizing with barium hydroxide the hydrolyzed reaction product of a polypropylene (molecular weight 2000) with 1 mole of phosphorus pentasulfide and '1 mole of sulfur, 3% of a barium sulfonate detergent prepared by carbonating a mineral oil solution of mahogany acid, and a 500% stoichiometrically excess amount of barium hydroxide in the presence of phenol as the promoter at 180 C., 3% of a supplemental ashless detergent prepared by copolymerizing a mixture of 95% (weight) of decyl-methacrylate and 5% (weight) of diethylaminoethylacrylate.
Example XVI SAE 80 mineral lubricating oil containing 2% of the product of Example M, 0.1% of phosphorus as zinc di-nhexylphosphorodithioate, 10% ot a chlorinated paraffin wax having a chlorine content of 40%, 2% of di-butyl tetrasulfide, 2% of sulfiurized dipentene, 0.2% of oleyl amide, 0.003% of an anti-foam agent, 0.02% of a pour point depressant, and 3% of a viscosity index irnprover.
, Example XVII SAE 10 mineral lubricating oil containing 3% of the product of Example 0, 0.075% of phosphorus as the zinc salt of a phosphorodithioic acid prepared by the reaction of phosphorus pentasulfide with an equimolar mixture of n-butyl alcohol and dodecyl alcohol, 3% of a barium detergent prepared by canbonating a mineral oil solution containing 1 mole of sperm oil, 0. 6 mole of octylphenol, 2 moles of barium oxide, and a small amount of water at 150 C.
Example XVIII SAE 20 mineral lubricating oil containing 2% of the product of Example P and 0. 07% of phosphorus a-s zinc di'moctylphosphorodithioate.
Example XIX SAE 30 mineral lubricating oil containing 3% of the product of Example Q and 0.1% of phosphorus as zinc 'di-(isobutylphenyl) -phosphorodithioate.
Example XX SAE 50 mineral lubricating oil containing 2% of the product of Example R.
25 product of Example S and 0.2% of phosphorus as the reaction product of 4 moles of turpentine with 1 mole of phosphorus pentasulfide.
The above lubricants are merely illustrative and the scope of invention includes the use of all of the additives previously illustrated as well as others within the broad concept of this invention described herein.
The effect veness of the nitrogenand boron-containing compositions as additives in lubricants to impart oxidationinhibiting, corrosion-inhibiting, and detergent properties is illustrated by the results obtained from an inhibitiondetergency test in which a 350 cc. sample of a lubricant containing 0.001% of iron naphthenate and 1.5% by weight of the additive vto be tested is heated at 300 F. for 48 hours in a 2 x 15 lborosilicate tube. A clean copperlead bearing is immersed in the lubricant along with an SAE 1020 steel test panel. Air is bubbled through the lubricant at the rate of 10 liters per hour. The oxidized sample is allowed to cool to 122 F. whereupon 0.5% (by volume) of water is added and dispersed into the sample. The sample is allowed to stand for 15 hours at room temperature and then filtered through dry No. 1 Whatman paper (double thickness) under slightly reduced pressure. The precipitant is washed with naphtha to constant weight and reported as milligrams of sludge per 100 ml. of oil. The bearing is scrubbed with naphtha, dried, and weighed, and the bearing weight change is reported in milligrams. The viscosity at 100 F. and 210 F. of the lubricant before and after the test is noted. Thus, the quantity of sludge is an indication of the ability of the additive to prevent the formation of harmful deposits; the bearing weight change is an indication of the corrosiveness of the lubricant; and the viscosity change of the lubricant is an indication of the oxidation resistance of the lubricant. The lubricant base employed in the test is a Mid-Continent, conventionally refined mineral oil having a viscosity of about 200 Saybolt Universal seconds at 100 F. The results of the test are summarized in Table I below.
Further illustration of the usefulness of the additive of this invention in lubricants is gained from a modified version (the modification consists of extending the test period from the usual 96 hours to 144 hours) of the CRC-EX3 engine test. This test is recognized in the field as an important test by which lubricants can be evaluated for use under light-duty service conditions. In this particular test the lubricant is used in the crankcase of a 1954 6-cylinder Chevrolet Powerglide engine operated for 144 hours under recurring cycling conditions, each cycle consisting of 2 hours at an engine speed of 500:25 r.p.m. under load and at an oil sump temperature of 100-125 F. and air fuel ratio of 10:1; 2 hours at an engine speed of 2500125 r.p.m. under a load of 40 brake-horse power and at an oil sump temperature of ISO-470 F. and air-fuel ratio of 16:1; and 2 hours at an engine speed of 2500:25 r.p.m. under a load of 40 brakehorsepower and at an oil sump temperature of 240- 250 F. and air-fuel ratio of 16: 1.
Table I Bearing Sludge Viscosity Increase Weight (milli- Additive (1.5% by weight of change grams per diluent-free chemical) (milli- 100 ml. of
grams) Lubri- 100 F. 210 F. cant) Percent Percent None 13. 2 3. 1 53. 1, 145 The acylated nitrogen com positions from which the N and B-containing additives are derived 30 20 100 Product of Example F 1. 3 0.9 13. 9 1. 8 Product of Example A 11.1 2. 8 +0. 9 2.0 Product of Example K 8. 9 2. 1 +3.3 2. 4 Product of Example N 11.2 4. 1 -1. 6 18. 7 Product of Example Q 15. 2 3. 2 -1. 7 60 After completion of the test the engine is dismantled and various parts of the engine are examined for deposit. The lubricant is then rated according to (1) the extent of piston ring-filling, (2) the amount of sludge formed in the engine (on a scale of -0, 80 being indicative of no sludge and 0 being indicative of extremely heavy sludge), and 3) the total amount of deposits, i.e., sludge and varnish, formed in the engine (on a scale of -0, 100 being indicative of no deposit and 0 being indicative of extremely heavy deposits). The lubricant used in the test comprises .an SAE 20 mineral .oil containing 1.41% by weight of the product of Example L. The lubricant is found to pass the test with the following result: ring filling, 1%; sludge rating, 75.3; total deposit rating, 93.4.
The efficacy of the nitrogen and boron-containing compositions as additives in lubricants for use under conditions of high speed .and high temperature operation is shown by the results of an engine test carried out in accordance with US. Army Ordnance tentative specification AXS-LSSI. This is known as the Caterpillar ORC- L-ll engine test and the particular test to which the lubricant is subjected is a modification of test, the modification consisting of the use of 'a fuel having a sulfur content of 1% (significantly higher than that of the specified fuel). In this test the lubricant is used in the crankcase of the 4-stroke diesel engine having a 5%" x 8" stroke and a compression ratio of 15 to 1 which is operated for 4 80 hours under the following conditions; speed, 100 r.p.m.;
. BTU input per minute, 2900- 5000; load, 20 brake-horsepower; water jacket outlet temperature, -180 'F.; and oil temperature, 145-150 F. The lubricant is evaluated in terms of 1) the piston cleanliness rating on a scale of 0-100 (100 being perfectly clean and 0 representing maximum deposit) and (2) percent ring filling. A lubricant comprising a SAE 10W-30 mineral oil containing 2% by Weight of the product of Example L is found to pass this test with the following result: ring filling, 19%; piston cleanliness, 96.0.
The eifectiveness of the nitrogenand boron-containing compositions of this invention as additives in lubricants for internal combustion engines is evaluated further by the CRCL4545 engine test. This test involves the operation of a 6-cylinder gasoline automobile engine for 36 hours under the following conditions: engine speed, 3150 r.p.m.; engine load, 30 brake-horsepower; jacket coolant temperature, outlet 200 F., inlet F.; oil sump temperature, 265 F.; and air-fuel ratio, 14.521. The lubricant is rated in terms of the weight loss of bearings, the cleanliness of the pistons and the overall varnish and sludge deposits on the various parts of the engine. By this test, a lubricant comprising a SAE 10W-3O mineral oil containing 2.08% by weight of the product of Example L is found to pass the test with the following results: piston cleanliness rating of 9.5 10 being perfectly clean), overall varnish and sludge rating of 96.7 (100 being perfectly clean), and an average weight loss per bearing of 2.5 milligrams.
The utility of the nitrogenand boron-containing compositions of this invention as additives in lubricants for use in 2-cycle internal combustion engines illustrated by the results of an engine test in which a 7-horsepower chain saw engine (McCulloch model No. 1-80) is operated for 25 hours under the following recurring cycling conditions, each cycle consisting of 15 minutes at zero load and 1800-2200 rpm. and 5 minutes at adjustable load and 5000 rpm. The lubricant comprises a SAE 30 mineral oil containing 7% by volume of the product of Example M and is incorporated in the fuel mixture consisting of 20 parts by volume of a leaded gasoline having an octane number of 95 and 1 part by volume of the lubricant. The lubricant is found to give by this test a piston varnish rating of 7.0 (on a scale of 0 10, 10 being indicative of no varnish and 0 being indicative of extremely heavy varnish) and a crankcase cover varnish rating of 10.0 (on the same scale as above) whereas the base 27 oil, i.e., SAE 30 mineral oil, gives a piston varnish rating of 2.5 and a crankcase cover varnish rating of 8.
What is claimed is:
'1. A process for preparing oil-soluble nitrogenand boron-containing compositions comprising forming an acylated nitrogen intermediate by the reaction at a temperature within the range of from about 80 to about 250 C., of a substantially aliphatic olefin polymer-substituted succinic acid-producing compound having at least about 50 aliphatic carbon atoms in the polymer substituent with at least about one-half equivalent of an amine, for each equivalent of the acid-producing compound used, selected from the class consisting of alkylene amines and hydroxy-substituted \alkylene amines, and reacting, at a temperature between about 50 C. and about 250 C., said acylated nitrogen intermediate with a boron compound selected from the class consisting of boron oxide, boron halide, boron acids, and esters of boron acids in an amount to provide from about 0.1 atomic proportion of boron for each mole of said acylated nitrogen intermediate to about atomic proportions of boron for each atomic proportion of nitrogen of said acylated nitrogen intermediate.
2. A process of claim 1 wherein the polymer substituent of the succinic acid-producing compound is derived from a polyisobutene having an average molecular weight within the range from about 700 to about 5000.
3. The process of claim 1 wherein the amine is a polyethylene polyamine.
4. The process of claim 1 wherein the boron compound is boric acid.
5. An oil-soluble nitrogenand boron-containing composition prepared by the process comprising forming an acylated nitrogen intermediate by the reaction at a temperature within the range of from about 80 C. to about 250 C., of a substantially aliphatic olefin polymer-substituted succinic acid-producing compound having at least about 50 aliphatic carbon atoms in the polymer substituent with at least about one-half equivalent of an amine for each equivalent of acid-producing compound used, selected from the class consisting of alkylene amines and hydroxy-substituted alkylene amines, and reacting at a temperature between about C. and about 250 C. said acylated nitrogen intermediate with a boron compound selected from the class consisting of boron oxide, boron halide, boron acids, and esters of boron acids in an amount to provide from about 0.1 atomic proportion of boron for each mole of said acylated nitrogen intermediate to about 10 atomic proportions of boron for each atomic proportion of nitrogen of said acylated nitrogen intermediate.
6'. The oil-soluble nitrogenand boron-containing composition of claim 5 wherein the polymer substituent of the succinic acid-producing compound is derived from a polymer of isobutene.
7. The oil-soluble nitrogenand boron-containing composition of claim 5 wherein the polymer substituent of the succinic acid-producing compound is derived from a polyisobutene having an average molecular weight within the range of from about 700' to about 5000.
8. The oil-soluble nitrogen, and boron-containing composition of claim 5 wherein the amine is a polyethylene polyamine.
9. The oil-soluble nitrogenand boron-containing composition of claim 5 wherein the boron compound is boric acid.
10. The oil-soluble nitrogenand boron-containing composition of claim 5 wherein the boron compound is boron trifluoride.
References Cited in the file of this patent UNITED STATES PATENTS 2,052,192 Piggott Aug. 25, 1936 2,216,618 Katz Oct. 1, 1940 2,234,581 Rosen Mar. 11, 1941 2,422,278 Young et a1 June 17, 1947 2,611,746 Kipp Sept. 23, 1952 3,000,916 Klass et al. Sept. 19, 1961 3,018,250 Anderson et al Jan. 23, 1962 3,018,291 Anderson et a1 Jan. 23, 1962
Claims (1)
1. A PROCESS FOR PREPARING OIL-SOLUBLE NITROGEN AND BORON-CONTAINING COMPOSITIONS COMPRISING FORMING AN ACYLATED NITROGEN INTERMEDIATE BY THE REACTION AT A TEMPERATURE WITHIN THE RANGE OF FROM ABOUT 80*F TO ABOUT 250*F C., OF A SUBSTANTIALLY ALIPHATIC OLEFIN POLYMER-SUBSITUTED SUCCINIC ACID-PRODUCING COMPOUND HAVING AT LEAST ABOUT 50 ALIPHATIC CARBON ATOMS IN THE POLYMER SUBSTITUENT WITH AT LEAST ABOUT ONE-HALF EQUIVALENT OF AN AMINE, FOR EACH EQUIVALENT OF THE ACID-PRODUCING COMPOUND USED, SELECTED FROM THE CLASS CONSISTING OF ALKYLENE AMINES AND HYRODXY-SUBSTITUTED ALKYLENE AMINES, AND REACTING, AT A TEMPERATURE BETWEEN ABOUT 50*F C. AND ABOUT 250*F C., SAID ACYLATED NITROGEN INTERMEDIATE WITH A BORON COMPOUND SELECTED FROM THE CLASS CONSISTING OF BORON OXIDE, BORON HAIDE, BORON ACIDS, AND ESTERS OF BORON ACIDS IN AN AMOUNT TO PROVIDE ROM ABOUT 0.1 ATOMIC PROPORTION OF BORON FOR EACH MOLE OF SAID ACYLATED NITROGEN INTERMEDIATE TO ABOUT 10 ATOMIC PROPORTIONS OF BORON FOR EACH ATOMIC PROPORTION OF NITROGEN OF SAID ACYLATED NITROGEN INTERMEDIATE.
Priority Applications (10)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US132305A US3087936A (en) | 1961-08-18 | 1961-08-18 | Reaction product of an aliphatic olefinpolymer-succinic acid producing compound with an amine and reacting the resulting product with a boron compound |
US185520A US3254025A (en) | 1961-08-18 | 1962-04-06 | Boron-containing acylated amine and lubricating compositions containing the same |
GB31343/62A GB1021182A (en) | 1961-08-18 | 1962-08-15 | Oil-soluble nitrogen containing products and process for preparing same |
GB39196/65A GB1021183A (en) | 1961-08-18 | 1962-08-15 | Oil-soluble nitrogen-containing products and process for preparing same |
DEL42737A DE1274776B (en) | 1961-08-18 | 1962-08-17 | Lubricating oil |
FR907156A FR1439820A (en) | 1961-08-18 | 1962-08-17 | Process for the production of compositions containing nitrogen and boron, soluble in oils |
DE19621644907 DE1644907A1 (en) | 1961-08-18 | 1962-08-17 | Lubricating oil |
JP39067633A JPS4936926B1 (en) | 1961-08-18 | 1964-12-03 | |
FR1359A FR87407E (en) | 1961-08-18 | 1965-01-08 | Process for the production of compositions containing nitrogen and boron, soluble in oils |
JP44011432A JPS4833242B1 (en) | 1961-08-18 | 1969-02-15 |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
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US132305A US3087936A (en) | 1961-08-18 | 1961-08-18 | Reaction product of an aliphatic olefinpolymer-succinic acid producing compound with an amine and reacting the resulting product with a boron compound |
US185520A US3254025A (en) | 1961-08-18 | 1962-04-06 | Boron-containing acylated amine and lubricating compositions containing the same |
Publications (1)
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US3087936A true US3087936A (en) | 1963-04-30 |
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US132305A Expired - Lifetime US3087936A (en) | 1961-08-18 | 1961-08-18 | Reaction product of an aliphatic olefinpolymer-succinic acid producing compound with an amine and reacting the resulting product with a boron compound |
US185520A Expired - Lifetime US3254025A (en) | 1961-08-18 | 1962-04-06 | Boron-containing acylated amine and lubricating compositions containing the same |
Family Applications After (1)
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US185520A Expired - Lifetime US3254025A (en) | 1961-08-18 | 1962-04-06 | Boron-containing acylated amine and lubricating compositions containing the same |
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US (2) | US3087936A (en) |
JP (2) | JPS4936926B1 (en) |
DE (2) | DE1644907A1 (en) |
FR (1) | FR87407E (en) |
GB (2) | GB1021183A (en) |
Cited By (453)
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US3163603A (en) * | 1963-12-11 | 1964-12-29 | Lubrizol Corp | Amide and imide derivatives of metal salts of substituted succinic acids |
US3188307A (en) * | 1962-04-13 | 1965-06-08 | Pure Oil Co | Alkenyl-n-sulfo-oxy-hydrocarbon-imides |
US3189544A (en) * | 1962-12-19 | 1965-06-15 | Shell Oil Co | Non-ash-containing lubricating oil composition |
US3194813A (en) * | 1962-10-18 | 1965-07-13 | Lubrizol Corp | High molecular weight alkenyl-n-omega amino hexylsuccinimide |
US3194814A (en) * | 1962-10-18 | 1965-07-13 | Lubrizol Corp | High molecular weight alkenyl-n-allyl succinimide |
US3194812A (en) * | 1962-08-31 | 1965-07-13 | Lubrizol Corp | High molecular weight alkenyl-n-para amino-phenyl succinimide |
US3231587A (en) * | 1960-06-07 | 1966-01-25 | Lubrizol Corp | Process for the preparation of substituted succinic acid compounds |
US3243371A (en) * | 1962-12-10 | 1966-03-29 | Shell Oil Co | Lubricating composition |
US3280034A (en) * | 1963-07-22 | 1966-10-18 | Monsanto Co | Alkenylsuccinimido alkyl-substituted imidazolidines and related materials |
US3281357A (en) * | 1964-12-02 | 1966-10-25 | Lubrizol Corp | Process for preparing nitrogen and aluminum containing compositions |
US3281428A (en) * | 1963-04-29 | 1966-10-25 | Lubrizol Corp | Reaction product of certain acylated nitrogen containing intermediates and a boron compound |
US3282955A (en) * | 1963-04-29 | 1966-11-01 | Lubrizol Corp | Reaction products of acylated nitrogen intermediates and a boron compound |
US3284410A (en) * | 1965-06-22 | 1966-11-08 | Lubrizol Corp | Substituted succinic acid-boron-alkylene amine-cyanamido derived additive and lubricating oil containing same |
US3284409A (en) * | 1965-06-22 | 1966-11-08 | Lubrizol Corp | Substituted succinic acid-boron-alkylene amine phosphatide derived additive and lubricating oil containing same |
US3294684A (en) * | 1963-07-11 | 1966-12-27 | Standard Oil Co | Lubricant compositions containing detergency additives |
US3306908A (en) * | 1963-12-26 | 1967-02-28 | Lubrizol Corp | Reaction products of high molecular weight hydrocarbon succinic compounds, amines and heavy metal compounds |
US3311558A (en) * | 1964-05-19 | 1967-03-28 | Rohm & Haas | N-alkylmorpholinone esters of alkenylsuccinic anhydrides |
US3322670A (en) * | 1963-08-26 | 1967-05-30 | Standard Oil Co | Detergent-dispersant lubricant additive having anti-rust and anti-wear properties |
US3338832A (en) * | 1963-04-29 | 1967-08-29 | Lubrizol Corp | Lubricating oil containing reaction product of certain acylated nitrogen containing intermediates and a boron compound |
US3338834A (en) * | 1965-11-19 | 1967-08-29 | Chevron Res | Process for preparing nitrogen and boron-containing lubricating oil additives |
US3340190A (en) * | 1965-06-01 | 1967-09-05 | Standard Oil Co | Railway diesel oil |
US3344069A (en) * | 1965-07-01 | 1967-09-26 | Lubrizol Corp | Lubricant additive and lubricant containing same |
US3367943A (en) * | 1963-11-01 | 1968-02-06 | Exxon Research Engineering Co | Process for preparing oil soluble additives which comprises reacting a c2 to c5 alkylene oxide with (a) reaction product of an alkenylsuccinic anhydride and an aliphaticpolyamine (b) reaction product of alkenylsuccinic anhydride, a c1 to c30 aliphatic hydrocarbon carboxylic acid and an aliphatic polyamine |
US3385791A (en) * | 1965-03-22 | 1968-05-28 | Standard Oil Co | Lubricant oil composition |
US3442808A (en) * | 1966-11-01 | 1969-05-06 | Standard Oil Co | Lubricating oil additives |
US3446808A (en) * | 1964-05-25 | 1969-05-27 | Universal Oil Prod Co | Borates of n-hydroxyalkyl-nitrogen-heterocyclic saturated compounds |
US3449362A (en) * | 1965-03-08 | 1969-06-10 | Standard Oil Co | Alkenyl hydrocarbon substituted succinimides of polyamino ureas and their boron-containing derivatives |
US3455831A (en) * | 1963-09-27 | 1969-07-15 | Monsanto Co | Imines containing a polyalkenylsuccinic anhydride substituent |
US3458530A (en) * | 1962-11-21 | 1969-07-29 | Exxon Research Engineering Co | Multi-purpose polyalkenyl succinic acid derivative |
DE1301535B (en) * | 1963-10-14 | 1970-02-05 | Lubrizol Corp | Process for the production of oil-soluble, nitrogen-containing reaction products |
US3718663A (en) * | 1967-11-24 | 1973-02-27 | Standard Oil Co | Preparation of oil-soluble boron derivatives of an alkylene polyamine-urea or thiourea-succinic anhydride addition product |
JPS4990704A (en) * | 1972-12-29 | 1974-08-29 | ||
US3892671A (en) * | 1972-08-25 | 1975-07-01 | Exxon Research Engineering Co | Lubricant containing dispersant-pour depressant polymer |
US3903151A (en) * | 1971-07-14 | 1975-09-02 | Chevron Res | Reaction products of alkali metal meborate and hydrocarbon substituted succinimide |
US3950341A (en) * | 1973-04-12 | 1976-04-13 | Toa Nenryo Kogyo Kabushiki Kaisha | Reaction product of a polyalkenyl succinic acid or its anhydride, a hindered alcohol and an amine |
US4025445A (en) * | 1975-12-15 | 1977-05-24 | Texaco Inc. | Boron amide lubricating oil additive |
US4059536A (en) * | 1974-03-29 | 1977-11-22 | Institut Francais Du Petrole | Improved process for preparing superbasic detergent additives |
US4080303A (en) * | 1974-07-22 | 1978-03-21 | The Lubrizol Corporation | Lubricant compositions containing boron dispersant, VI improver, and aromatic carboxylic acid esters |
US4092127A (en) * | 1976-12-20 | 1978-05-30 | Exxon Research & Engineering Co. | Anti-dieseling additive for spark ignition engines |
US4097389A (en) * | 1974-08-05 | 1978-06-27 | Mobil Oil Corporation | Novel amino alcohol reaction products and compositions containing the same |
US4184851A (en) * | 1977-07-25 | 1980-01-22 | Exxon Research & Engineering Co. | Borated derivatives of hydrocarbon substituted succinamic acids and/or acid salts thereof are flow improvers for middle distillate fuel oils (PT-364) |
US4295983A (en) * | 1980-06-12 | 1981-10-20 | Ethyl Corporation | Lubricating oil composition containing boronated N-hydroxymethyl succinimide friction reducers |
US4338205A (en) * | 1980-08-25 | 1982-07-06 | Exxon Research & Engineering Co. | Lubricating oil with improved diesel dispersancy |
EP0061346A2 (en) * | 1981-03-23 | 1982-09-29 | Edwin Cooper Inc. | Dispersant composition for lubricating oil, additive packages and lubricating oil compositions comprising the dispersant ingredients of said composition, a method of imparting dispersancy to a lubricating oil, and ingredients intended for use in a dispersant mixture |
US4368133A (en) * | 1979-04-02 | 1983-01-11 | The Lubrizol Corporation | Aqueous systems containing nitrogen-containing, phosphorous-free carboxylic solubilizer/surfactant additives |
US4414125A (en) * | 1979-12-01 | 1983-11-08 | Chemische Werke Huels Aktiengesellschaft | Alkali metal or amine salts of a mixture of 2- and 3-alkyladipic acids as corrosion inhibitors |
US4447348A (en) * | 1981-02-25 | 1984-05-08 | The Lubrizol Corporation | Carboxylic solubilizer/surfactant combinations and aqueous compositions containing same |
US4448703A (en) * | 1981-02-25 | 1984-05-15 | The Lubrizol Corporation | Carboxylic solubilizer/surfactant combinations and aqueous compositions containing same |
US4471091A (en) * | 1982-08-09 | 1984-09-11 | The Lubrizol Corporation | Combinations of carboxylic acylating agents substituted with olefin polymers of high and low molecular weight mono-olefins, derivatives thereof, and fuels and lubricants containing same |
US4486573A (en) * | 1982-08-09 | 1984-12-04 | The Lubrizol Corporation | Carboxylic acylating agents substituted with olefin polymers of high molecular weight mono-olefins, derivatives thereof, and fuels and lubricants containing same |
US4489194A (en) * | 1982-08-09 | 1984-12-18 | The Lubrizol Corporation | Carboxylic acylating agents substituted with olefin polymers of high/low molecular weight mono-olefins, derivatives thereof, and fuels and lubricants containing same |
WO1985003504A2 (en) * | 1984-02-09 | 1985-08-15 | The Lubrizol Corporation | Process for making substituted carboxylic acids and derivatives thereof |
US4559155A (en) * | 1982-08-09 | 1985-12-17 | The Lubrizol Corporation | Hydrocarbyl substituted carboxylic acylating agent derivative containing combinations, and fuels containing same |
EP0167295A2 (en) * | 1984-06-05 | 1986-01-08 | Exxon Research And Engineering Company | Improved lubricating compositions |
US4564460A (en) * | 1982-08-09 | 1986-01-14 | The Lubrizol Corporation | Hydrocarbyl-substituted carboxylic acylating agent derivative containing combinations, and fuels containing same |
US4575526A (en) * | 1982-08-09 | 1986-03-11 | The Lubrizol Corporation | Hydrocarbyl substituted carboxylic acylaging agent derivative containing combinations, and fuels containing same |
US4596663A (en) * | 1982-08-09 | 1986-06-24 | The Lubrizol Corporation | Carboxylic acylating agents substituted with olefin polymers of high molecular weight mono-olefins, derivatives thereof, and fuels and lubricants containing same |
US4613342A (en) * | 1982-08-09 | 1986-09-23 | The Lubrizol Corporation | Hydrocarbyl substituted carboxylic acylating agent derivative containing combinations, and fuels containing same |
US4623684A (en) | 1982-08-09 | 1986-11-18 | The Lubrizol Corporation | Hydrocarbyl substituted carboxylic acylating agent derivative containing combinations, and fuels containing same |
US4637886A (en) * | 1982-12-27 | 1987-01-20 | Exxon Research & Engineering Co. | Macrocyclic polyamine and polycyclic polyamine multifunctional lubricating oil additives |
US4666620A (en) * | 1978-09-27 | 1987-05-19 | The Lubrizol Corporation | Carboxylic solubilizer/surfactant combinations and aqueous compositions containing same |
WO1987003003A1 (en) | 1985-11-08 | 1987-05-21 | The Lubrizol Corporation | Fuel compositions |
US4749505A (en) * | 1985-07-08 | 1988-06-07 | Exxon Chemical Patents Inc. | Olefin polymer viscosity index improver additive useful in oil compositions |
US4755311A (en) * | 1986-08-14 | 1988-07-05 | The Lubrizol Corporation | Phosphorus-, sulfur- and boron-containing compositions, and lubricant and functional fluid compositions containing same |
US4756820A (en) * | 1985-09-06 | 1988-07-12 | Betz Laboratories, Inc. | Method for retarding corrosion and coke formation and deposition during pyrolytic hydrocarbon processing |
US4770803A (en) * | 1986-07-03 | 1988-09-13 | The Lubrizol Corporation | Aqueous compositions containing carboxylic salts |
US4820432A (en) * | 1987-07-24 | 1989-04-11 | Exxon Chemical Patents Inc. | Lactone-modified, Mannich base dispersant additives useful in oleaginous compositions |
US4855074A (en) * | 1988-03-14 | 1989-08-08 | Ethyl Petroleum Additives, Inc. | Homogeneous additive concentrates and their formation |
US4863624A (en) * | 1987-09-09 | 1989-09-05 | Exxon Chemical Patents Inc. | Dispersant additives mixtures for oleaginous compositions |
US4866139A (en) * | 1986-10-07 | 1989-09-12 | Exxon Chemical Patents Inc. | Lactone modified, esterified dispersant additives useful in oleaginous compositions |
US4866140A (en) * | 1986-10-07 | 1989-09-12 | Exxon Chemical Patents Inc. | Lactone modified adducts or reactants and oleaginous compositions containing same |
US4866141A (en) * | 1986-10-07 | 1989-09-12 | Exxon Chemical Patents Inc. | Lactone modified, esterfied or aminated additives useful in oleaginous compositions and compositions containing same |
JPH01502987A (en) * | 1986-06-13 | 1989-10-12 | ザ ルブリゾル コーポレーション | Phosphorus-containing lubricants and functional fluid compositions |
GB2183243B (en) * | 1985-10-09 | 1990-01-24 | Nippon Oil Co Ltd | Process for preparing oil-soluble nitrogen-containing compounds |
EP0351964A1 (en) | 1988-06-24 | 1990-01-24 | Exxon Chemical Patents Inc. | Synergistic combination of additives useful in power transmitting compositions |
US4906394A (en) * | 1986-10-07 | 1990-03-06 | Exxon Chemical Patents Inc. | Lactone modified mono-or dicarboxylic acid based adduct dispersant compositions |
US4925983A (en) * | 1986-11-12 | 1990-05-15 | The Lubrizol Corporation | Boronated compounds |
US4943382A (en) * | 1988-04-06 | 1990-07-24 | Exxon Chemical Patents Inc. | Lactone modified dispersant additives useful in oleaginous compositions |
US4954277A (en) * | 1986-10-07 | 1990-09-04 | Exxon Chemical Patents Inc. | Lactone modified, esterified or aminated additives useful in oleaginous compositions and compositions containing same |
US4954276A (en) * | 1986-10-07 | 1990-09-04 | Exxon Chemical Patents Inc. | Lactone modified adducts or reactants and oleaginous compositions containing same |
US4963275A (en) * | 1986-10-07 | 1990-10-16 | Exxon Chemical Patents Inc. | Dispersant additives derived from lactone modified amido-amine adducts |
US4971711A (en) * | 1987-07-24 | 1990-11-20 | Exxon Chemical Patents, Inc. | Lactone-modified, mannich base dispersant additives useful in oleaginous compositions |
EP0399764A1 (en) | 1989-05-22 | 1990-11-28 | Ethyl Petroleum Additives Limited | Lubricant compositions |
US5032320A (en) * | 1986-10-07 | 1991-07-16 | Exxon Chemical Patents Inc. | Lactone modified mono- or dicarboxylic acid based adduct dispersant compositions |
US5041622A (en) * | 1988-04-22 | 1991-08-20 | The Lubrizol Corporation | Three-step process for making substituted carboxylic acids and derivatives thereof |
US5110488A (en) * | 1986-11-24 | 1992-05-05 | The Lubrizol Corporation | Lubricating compositions containing reduced levels of phosphorus |
US5198133A (en) * | 1988-03-14 | 1993-03-30 | Ethyl Petroleum Additives, Inc. | Modified succinimide or sucinamide dispersants and their production |
US5221491A (en) * | 1991-08-09 | 1993-06-22 | Exxon Chemical Patents Inc. | Two-cycle oil additive |
US5225093A (en) * | 1990-02-16 | 1993-07-06 | Ethyl Petroleum Additives, Inc. | Gear oil additive compositions and gear oils containing the same |
EP0558835A1 (en) | 1992-01-30 | 1993-09-08 | Albemarle Corporation | Biodegradable lubricants and functional fluids |
US5304315A (en) * | 1992-04-15 | 1994-04-19 | Exxon Chemical Patents Inc. | Prevention of gel formation in two-cycle oils |
US5308521A (en) * | 1992-07-08 | 1994-05-03 | The Lubrizol Corporation | Lubricant with improved anti-corrosion properties |
US5312554A (en) * | 1987-05-26 | 1994-05-17 | Exxon Chemical Patents Inc. | Process for preparing stable oleaginous compositions |
WO1994013762A1 (en) * | 1992-12-17 | 1994-06-23 | Exxon Chemical Patents Inc. | Improved low sediment process for forming borated dispersant |
US5328619A (en) * | 1991-06-21 | 1994-07-12 | Ethyl Petroleum Additives, Inc. | Oil additive concentrates and lubricants of enhanced performance capabilities |
US5330667A (en) * | 1992-04-15 | 1994-07-19 | Exxon Chemical Patents Inc. | Two-cycle oil additive |
US5334329A (en) * | 1988-10-07 | 1994-08-02 | The Lubrizol Corporation | Lubricant and functional fluid compositions exhibiting improved demulsibility |
EP0611818A1 (en) | 1990-07-31 | 1994-08-24 | Exxon Chemical Patents Inc. | Low pressure derived mixed phosphorous- and sulfur-containing reaction products useful in power transmitting compositions and process for preparing the same |
US5370807A (en) * | 1992-05-15 | 1994-12-06 | Ministero Dell'universita' E Della Ricerca Scientifica E Technologica | Boron-containing additive for lubricating oils, and process for preparing said additive |
US5389273A (en) * | 1988-03-14 | 1995-02-14 | Ethyl Petroleum Additives, Inc. | Modified succinimide or succinamide dispersants and their production |
US5439606A (en) * | 1988-03-14 | 1995-08-08 | Ethyl Petroleum Additives, Inc. | Modified succinimide or succinamide dispersants and their production |
EP0683220A2 (en) | 1994-05-18 | 1995-11-22 | Ethyl Corporation | Lubricant additive compositions |
EP0695798A2 (en) | 1994-08-03 | 1996-02-07 | The Lubrizol Corporation | Lubricating compositions, concentrates, and greases containing the combination of an organic polysulfide and an overbased composition or a phosphorus or boron compound |
US5490945A (en) * | 1991-04-19 | 1996-02-13 | The Lubrizol Corporation | Lubricating compositions and concentrates |
US5498809A (en) * | 1992-12-17 | 1996-03-12 | Exxon Chemical Patents Inc. | Polymers derived from ethylene and 1-butene for use in the preparation of lubricant dispersant additives |
EP0713908A1 (en) | 1994-11-22 | 1996-05-29 | Ethyl Corporation | Power transmission fluids |
US5554310A (en) * | 1992-12-17 | 1996-09-10 | Exxon Chemical Patents Inc. | Trisubstituted unsaturated polymers |
US5558802A (en) * | 1995-09-14 | 1996-09-24 | Exxon Chemical Patents Inc | Multigrade crankcase lubricants with low temperature pumpability and low volatility |
US5562864A (en) * | 1991-04-19 | 1996-10-08 | The Lubrizol Corporation | Lubricating compositions and concentrates |
US5562867A (en) * | 1993-12-30 | 1996-10-08 | Exxon Chemical Patents Inc | Biodegradable two-cycle oil composition |
US5614480A (en) * | 1991-04-19 | 1997-03-25 | The Lubrizol Corporation | Lubricating compositions and concentrates |
US5629434A (en) * | 1992-12-17 | 1997-05-13 | Exxon Chemical Patents Inc | Functionalization of polymers based on Koch chemistry and derivatives thereof |
US5643859A (en) * | 1992-12-17 | 1997-07-01 | Exxon Chemical Patents Inc. | Derivatives of polyamines with one primary amine and secondary of tertiary amines |
US5646332A (en) * | 1992-12-17 | 1997-07-08 | Exxon Chemical Patents Inc. | Batch Koch carbonylation process |
US5646098A (en) * | 1990-07-23 | 1997-07-08 | Exxon Chemical Patents Inc | Carbonyl containing compounds and their derivatives as multi-functional fuel and lube additives |
US5650536A (en) * | 1992-12-17 | 1997-07-22 | Exxon Chemical Patents Inc. | Continuous process for production of functionalized olefins |
US5652202A (en) * | 1995-08-15 | 1997-07-29 | Exxon Chemical Patents Inc. | Lubricating oil compositions |
US5652201A (en) * | 1991-05-29 | 1997-07-29 | Ethyl Petroleum Additives Inc. | Lubricating oil compositions and concentrates and the use thereof |
US5658862A (en) * | 1994-12-20 | 1997-08-19 | Exxon Research And Engineering Company | Engine oil with improved fuel economy properties (law372). |
FR2747687A1 (en) * | 1996-04-19 | 1997-10-24 | Ethyl Petroleum Additives Ltd | OLEOSOLUBLE DIPERSANT FOR LUBRICATING OIL |
US5756428A (en) * | 1986-10-16 | 1998-05-26 | Exxon Chemical Patents Inc. | High functionality low molecular weight oil soluble dispersant additives useful in oleaginous composition |
US5767046A (en) * | 1994-06-17 | 1998-06-16 | Exxon Chemical Company | Functionalized additives useful in two-cycle engines |
US6008165A (en) * | 1998-07-31 | 1999-12-28 | The Lubrizol Corporation | Alcohol borate esters and borated dispersants to improve bearing corrosion in engine oils |
US6010986A (en) * | 1998-07-31 | 2000-01-04 | The Lubrizol Corporation | Alcohol borate esters to improve bearing corrosion in engine oils |
USRE36479E (en) * | 1986-07-03 | 2000-01-04 | The Lubrizol Corporation | Aqueous compositions containing nitrogen-containing salts |
US6051537A (en) * | 1985-07-11 | 2000-04-18 | Exxon Chemical Patents Inc | Dispersant additive mixtures for oleaginous compositions |
US6127321A (en) * | 1985-07-11 | 2000-10-03 | Exxon Chemical Patents Inc | Oil soluble dispersant additives useful in oleaginous compositions |
US6225437B1 (en) | 1999-06-24 | 2001-05-01 | Albemarle Corporation | Sizing agents of enhanced performance capabilities |
US6231659B1 (en) | 1999-06-24 | 2001-05-15 | Albemarle Corporation | Sizing agents and starting materials for their preparation |
US6306802B1 (en) | 1994-09-30 | 2001-10-23 | Exxon Chemical Patents Inc. | Mixed antioxidant composition |
US6362136B1 (en) | 1994-05-23 | 2002-03-26 | The Lubrizol Corporation | Compositions for extending seal life, and lubricants and functional fluids containing the same |
US6423670B2 (en) | 2000-03-20 | 2002-07-23 | Infineum International Ltd. | Lubricating oil compositions |
US6476096B1 (en) * | 1998-02-02 | 2002-11-05 | Xaar Technology Limited | Ink jet printer ink |
US6489271B1 (en) | 1994-08-03 | 2002-12-03 | The Lubrizol Corporation | Combination of a sulfur compound and specific phosphorus compounds and their use in lubricating compositions, concentrates and greases |
US20020193650A1 (en) * | 2001-05-17 | 2002-12-19 | Goze Maria Caridad B. | Low noack volatility poly alpha-olefins |
US6573223B1 (en) | 2002-03-04 | 2003-06-03 | The Lubrizol Corporation | Lubricating compositions with good thermal stability and demulsibility properties |
US20030172584A1 (en) * | 2002-03-13 | 2003-09-18 | Henly Timothy J. | Fuel lubricity additives derived from hydrocarbyl succinic anhydrides and hydroxy amines, and middle distillate fuels containing same |
US20030173251A1 (en) * | 2000-12-22 | 2003-09-18 | Antonio Gutierrez | Hydroxy aromatic mannich base condensation products and the use thereof as soot dispersants in lubricating oil compositions |
US6627584B2 (en) | 2002-01-28 | 2003-09-30 | Ethyl Corporation | Automatic transmission fluid additive comprising reaction product of hydrocarbyl acrylates and dihydrocarbyldithiophosphoric acids |
WO2003095595A1 (en) | 2002-05-09 | 2003-11-20 | The Lubrizol Corporation | Continuously variable transmission fluids comprising a combination of calcium- and magnesium-overbased detergents |
US20040033908A1 (en) * | 2002-08-16 | 2004-02-19 | Deckman Douglas E. | Functional fluid lubricant using low Noack volatility base stock fluids |
US6734148B2 (en) | 2001-12-06 | 2004-05-11 | Infineum International Ltd. | Dispersants and lubricating oil compositions containing same |
US6743757B2 (en) | 2001-12-06 | 2004-06-01 | Infineum International Ltd. | Dispersants and lubricating oil compositions containing same |
US20040147410A1 (en) * | 2003-01-15 | 2004-07-29 | Milner Jeffrey L | Extended drain, thermally stable, gear oil formulations |
US20040260027A1 (en) * | 2003-06-20 | 2004-12-23 | Michaud Vincent Jean Marie | Process for forming polyalkenyl acylating agents |
US20040260032A1 (en) * | 2003-06-20 | 2004-12-23 | Irving Matthew David | Low sediment process for thermally reacting highly reactive polymers and enophiles |
US20050041395A1 (en) * | 2003-08-21 | 2005-02-24 | The Lubrizol Corporation | Multifunctional dispersants |
US20050065043A1 (en) * | 2003-09-23 | 2005-03-24 | Henly Timothy J. | Power transmission fluids having extended durability |
US20050101494A1 (en) * | 2003-11-10 | 2005-05-12 | Iyer Ramnath N. | Lubricant compositions for power transmitting fluids |
US20050101497A1 (en) * | 2003-11-12 | 2005-05-12 | Saathoff Lee D. | Compositions and methods for improved friction durability in power transmission fluids |
US20050192185A1 (en) * | 2004-02-27 | 2005-09-01 | Saathoff Lee D. | Power transmission fluids |
US20050202979A1 (en) * | 2004-03-10 | 2005-09-15 | Ethyl Petroleum Additives, Inc. | Power transmission fluids with enhanced extreme pressure characteristics |
US20050255251A1 (en) * | 2004-05-17 | 2005-11-17 | Hodge Robert L | Composition, method of making, and treatment of wood with an injectable wood preservative slurry having biocidal particles |
US20060003905A1 (en) * | 2004-07-02 | 2006-01-05 | Devlin Cathy C | Additives and lubricant formulations for improved corrosion protection |
US20060025314A1 (en) * | 2004-07-28 | 2006-02-02 | Afton Chemical Corporation | Power transmission fluids with enhanced extreme pressure and antiwear characteristics |
US20060075923A1 (en) * | 2004-10-12 | 2006-04-13 | Richardson H W | Method of manufacture and treatment of wood with injectable particulate iron oxide |
US20060122073A1 (en) * | 2004-12-08 | 2006-06-08 | Chip Hewette | Oxidation stable gear oil compositions |
WO2006063161A2 (en) * | 2004-12-09 | 2006-06-15 | The Lubrizol Corporation | Process of preparation of an additive and its use |
WO2006094011A2 (en) | 2005-03-01 | 2006-09-08 | R.T. Vanderbilt Company, Inc. | Molybdenum dialkyldithiocarbamate compositions and lubricating compositions containing the same |
US20060217273A1 (en) * | 2005-03-23 | 2006-09-28 | Nubar Ozbalik | Lubricating compositions |
US20060223716A1 (en) * | 2005-04-04 | 2006-10-05 | Milner Jeffrey L | Tractor fluids |
US20060252660A1 (en) * | 2005-05-09 | 2006-11-09 | Akhilesh Duggal | Hydrolytically stable viscosity index improves |
EP1728848A1 (en) | 2005-06-01 | 2006-12-06 | Infineum International Limited | Use of unsaturated olefin polymers to improve the compatibility between nitrile rubber seals and lubricating oil compositions |
US20070021310A1 (en) * | 2005-07-11 | 2007-01-25 | Olliges William E | Corrosion Prevention and Friction Reduction Coating and Low Temperature Process |
US20070042917A1 (en) * | 2005-07-12 | 2007-02-22 | Ramanathan Ravichandran | Amine Tungstates and Lubricant Compositions |
US20070078066A1 (en) * | 2005-10-03 | 2007-04-05 | Milner Jeffrey L | Lubricant formulations containing extreme pressure agents |
US20070105728A1 (en) * | 2005-11-09 | 2007-05-10 | Phillips Ronald L | Lubricant composition |
US20070111906A1 (en) * | 2005-11-12 | 2007-05-17 | Milner Jeffrey L | Relatively low viscosity transmission fluids |
US20070142237A1 (en) * | 2005-11-09 | 2007-06-21 | Degonia David J | Lubricant composition |
US20070142659A1 (en) * | 2005-11-09 | 2007-06-21 | Degonia David J | Sulfur-containing, phosphorus-containing compound, its salt, and methods thereof |
US20070142660A1 (en) * | 2005-11-09 | 2007-06-21 | Degonia David J | Salt of a sulfur-containing, phosphorus-containing compound, and methods thereof |
US20070259016A1 (en) * | 2006-05-05 | 2007-11-08 | Hodge Robert L | Method of treating crops with submicron chlorothalonil |
US20080015125A1 (en) * | 2006-07-14 | 2008-01-17 | Devlin Mark T | Lubricant compositions |
US20080015124A1 (en) * | 2006-07-14 | 2008-01-17 | Devlin Mark T | Lubricant composition |
US20080015127A1 (en) * | 2006-07-14 | 2008-01-17 | Loper John T | Boundary friction reducing lubricating composition |
WO2008013698A1 (en) | 2006-07-21 | 2008-01-31 | Exxonmobil Research And Engineering Company | Method for lubricating heavy duty geared apparatus |
US20080051305A1 (en) * | 2006-08-28 | 2008-02-28 | Devlin Mark T | Lubricant composition |
US20080119377A1 (en) * | 2006-11-22 | 2008-05-22 | Devlin Mark T | Lubricant compositions |
US20080182768A1 (en) * | 2007-01-31 | 2008-07-31 | Devlin Cathy C | Lubricant composition for bio-diesel fuel engine applications |
EP1959003A2 (en) | 2007-02-08 | 2008-08-20 | Infineum International Limited | Soot dispersants and lubricating oil compositions containing same |
US20080213608A1 (en) * | 2004-10-08 | 2008-09-04 | Richardson Hugh W | Milled Submicron Chlorothalonil With Narrow Particle Size Distribution, and Uses Thereof |
US20080274921A1 (en) * | 2007-05-04 | 2008-11-06 | Ian Macpherson | Environmentally-Friendly Lubricant Compositions |
WO2008154334A1 (en) | 2007-06-08 | 2008-12-18 | Infineum International Limited | Additives and lubricating oil compositions containing same |
US20090011963A1 (en) * | 2007-07-06 | 2009-01-08 | Afton Chemical Corporation | Truck fleet fuel economy by the use of optimized engine oil, transmission fluid, and gear oil |
US20090029888A1 (en) * | 2005-07-12 | 2009-01-29 | Ramanathan Ravichandran | Amine tungstates and lubricant compositions |
US20090031614A1 (en) * | 2007-08-01 | 2009-02-05 | Ian Macpherson | Environmentally-Friendly Fuel Compositions |
EP2025737A1 (en) | 2007-08-01 | 2009-02-18 | Afton Chemical Corporation | Environmentally-friendly fuel compositions |
US20090071067A1 (en) * | 2007-09-17 | 2009-03-19 | Ian Macpherson | Environmentally-Friendly Additives And Additive Compositions For Solid Fuels |
WO2009045979A1 (en) | 2007-10-03 | 2009-04-09 | The Lubrizol Corporation | Lubricants that decrease micropitting for industrial gears |
US20090123505A1 (en) * | 2004-05-17 | 2009-05-14 | Phibrowood, Llc | Particulate Wood Preservative and Method for Producing Same |
US20090143478A1 (en) * | 2004-10-08 | 2009-06-04 | Phibrowood, Llc | Milled Submicron Organic Biocides With Narrow Particle Size Distribution, and Uses Thereof |
US20090156449A1 (en) * | 2007-12-12 | 2009-06-18 | Rowland Robert G | Alkylated 1,3-benzenediamine compounds and methods for producing same |
US20090156441A1 (en) * | 2007-12-12 | 2009-06-18 | Rowland Robert G | Cycloalkyl phenylenediamines as deposit control agents for lubricants |
EP2075315A1 (en) | 2007-12-12 | 2009-07-01 | Infineum International Limited | Additive Compositions with Michael adducts of N-substituted phenylenediamines |
EP2075264A1 (en) | 2007-12-26 | 2009-07-01 | Infineum International Limited | Method of forming polyalkene substituted carboxylic acid compositions |
EP2083063A1 (en) | 2008-01-22 | 2009-07-29 | Infineum International Limited | Lubricating oil composition |
EP2083024A1 (en) | 2008-01-24 | 2009-07-29 | Afton Chemical Corporation | Olefin copolymer dispersant VI improver and lubricant compositions and uses thereof |
EP2090642A1 (en) | 2008-02-08 | 2009-08-19 | Infineum International Limited | Engine lubrication |
US20090223408A1 (en) * | 2004-05-17 | 2009-09-10 | Phibrowood, Llc | Use of Sub-Micron Copper Salt Particles in Wood Preservation |
US20090233822A1 (en) * | 2008-03-11 | 2009-09-17 | Afton Chemical Corporation | Ultra-low sulfur clutch-only transmission fluids |
DE102009001301A1 (en) | 2008-03-11 | 2009-09-24 | Volkswagen Ag | Method for lubricating a component only for the clutch of an automatic transmission, which requires lubrication |
DE102009012567A1 (en) | 2008-03-11 | 2009-10-01 | Afton Chemical Corp. | Clutch-only transmission fluid useful for lubrication comprises oil formulated with additive components having metal detergent, phosphorus-based wear preventative, phosphorylated and boronated dispersant, sulfurized extreme pressure agent |
WO2009119831A1 (en) | 2008-03-28 | 2009-10-01 | 富士フイルム株式会社 | Composition and method for forming coating film |
EP2116590A1 (en) | 2005-02-18 | 2009-11-11 | Infineum International Limited | Soot dispersants and lubricating oil compositions containing same |
US20090280185A1 (en) * | 2003-06-17 | 2009-11-12 | Phibrowood, Llc | Particulate wood preservative and method for producing the same |
EP2161326A1 (en) | 2008-09-05 | 2010-03-10 | Infineum International Limited | Lubricating oil compositions |
EP2163602A1 (en) | 2008-09-05 | 2010-03-17 | Infineum International Limited | A lubricating oil composition |
WO2010077630A1 (en) | 2008-12-09 | 2010-07-08 | The Lubrizol Corporation | Lubricating composition containing a compound derived from a hydroxy-carboxylic acid |
EP2206764A1 (en) | 2008-12-23 | 2010-07-14 | Infineum International Limited | Aniline compounds as ashless TBN sources and lubricating oil compositions containing same |
EP2233554A1 (en) | 2009-03-27 | 2010-09-29 | Infineum International Limited | Lubricating oil compositions |
EP2236590A1 (en) | 2009-04-01 | 2010-10-06 | Infineum International Limited | Lubricating oil composition |
EP2239314A1 (en) | 2009-04-06 | 2010-10-13 | Infineum International Limited | Lubricating oil composition |
WO2010115594A1 (en) | 2009-04-07 | 2010-10-14 | Infineum International Limited | Marine engine lubrication |
US20110036262A1 (en) * | 2005-07-11 | 2011-02-17 | Advanced Lubrication Technology, Inc. | Corrosion Prevention and Friction Reduction Coating and Low Temperature Process |
EP2290041A2 (en) | 2009-08-24 | 2011-03-02 | Infineum International Limited | A lubricating oil composition |
EP2290038A2 (en) | 2009-08-24 | 2011-03-02 | Infineum International Limited | A lubricating oil composition |
EP2290043A1 (en) | 2009-08-24 | 2011-03-02 | Infineum International Limited | A lubricating oil composition comprising metal dialkyldithiophosphate and carbodiimide |
WO2011025636A1 (en) | 2009-08-28 | 2011-03-03 | Chemtura Corporation | Two-stage process and system for forming high viscosity polyalphaolefins |
WO2011034829A1 (en) | 2009-09-16 | 2011-03-24 | The Lubrizol Corporation | Lubricating composition containing an ester |
EP2302023A2 (en) | 2002-10-04 | 2011-03-30 | R.T. Vanderbilt Company, Inc. | Synergistic organoborate compositions and lubricating compositions containing same |
US20110105371A1 (en) * | 2009-11-05 | 2011-05-05 | Afton Chemical Corporation | Olefin copolymer vi improvers and lubricant compositions and uses thereof |
EP2319904A1 (en) | 2009-10-29 | 2011-05-11 | Infineum International Limited | Lubrication and lubricating oil compositions comprising phenylene diamines |
WO2011059583A1 (en) | 2009-10-29 | 2011-05-19 | Chemtura Corporation | Lubrication and lubricating oil compositions |
WO2011066145A1 (en) | 2009-11-30 | 2011-06-03 | The Lubrizol Corporation | Stabilized blends containing friction modifiers |
EP2363454A1 (en) | 2010-02-23 | 2011-09-07 | Infineum International Limited | A lubricating oil composition |
EP2366761A1 (en) | 2010-03-09 | 2011-09-21 | Infineum International Limited | Morpholine derivatives as ashless TBN sources and lubricating oil compositions containing same |
EP2371932A1 (en) | 2010-04-01 | 2011-10-05 | Infineum International Limited | A lubricating oil composition |
EP2371934A1 (en) | 2010-03-31 | 2011-10-05 | Infineum International Limited | Lubricating oil composition |
EP2374866A1 (en) | 2010-04-06 | 2011-10-12 | Infineum International Limited | A lubricating oil composition comprising alkoxylated phenol-formaldehyde condensate |
WO2011130142A1 (en) | 2010-04-15 | 2011-10-20 | The Lubrizol Corporation | Low-ash lubricating oils for diesel engines |
EP2390306A1 (en) | 2009-12-01 | 2011-11-30 | Infineum International Limited | A lubricating oil composition |
WO2011149810A1 (en) | 2010-05-24 | 2011-12-01 | The Lubrizol Corporation | Lubricating composition |
EP2420552A1 (en) | 2010-08-19 | 2012-02-22 | Infineum International Limited | EGR Equipped Diesel Engines and Lubricating Oil Compositions |
EP2453000A1 (en) | 2010-11-08 | 2012-05-16 | Infineum International Limited | Lubricating Oil Composition comprising a hydrogenated imide derived from a Diels-Alder adduct of maleic anhydride and a furan |
EP2457984A1 (en) | 2010-11-30 | 2012-05-30 | Infineum International Limited | A lubricating oil composition |
WO2012141855A1 (en) | 2011-04-15 | 2012-10-18 | R.T. Vanderbilt Company, Inc. | Molybdenum dialkyldithiocarbamate compositions and lubricating compositions containing the same |
US8299003B2 (en) | 2005-11-09 | 2012-10-30 | Afton Chemical Corporation | Composition comprising a sulfur-containing, phosphorus-containing compound, and/or its salt, and uses thereof |
WO2012162020A1 (en) | 2011-05-26 | 2012-11-29 | The Lubrizol Corporation | Stabilized blends containing antioxidants |
WO2012162027A1 (en) | 2011-05-26 | 2012-11-29 | The Lubrizol Corporation | Stabilized blends containing friction modifiers |
WO2013003392A1 (en) | 2011-06-30 | 2013-01-03 | Exxonmobil Research And Engineering Company | Method of improving pour point of lubricating compositions containing polyalkylene glycol mono ethers |
WO2013003405A1 (en) | 2011-06-30 | 2013-01-03 | Exxonmobil Research And Engineering Company | Lubricating compositions containing polyalkylene glycol mono ethers |
WO2013003394A1 (en) | 2011-06-30 | 2013-01-03 | Exxonmobil Research And Engineering Company | Lubricating compositions containing polyetheramines |
WO2013003406A1 (en) | 2011-06-29 | 2013-01-03 | Exxonmobil Research And Engineering Company | Low viscosity engine oil with superior engine wear protection |
EP2559748A1 (en) | 2011-08-19 | 2013-02-20 | Infineum International Limited | Lubricating oil composition |
EP2574656A1 (en) | 2011-09-28 | 2013-04-03 | Infineum International Limited | Lubricating oil compositions |
WO2013055482A1 (en) | 2011-10-10 | 2013-04-18 | Exxonmobil Research And Engineering Company | Lubricating compositions |
EP2584025A1 (en) | 2011-10-21 | 2013-04-24 | Infineum International Limited | Lubricating oil composition |
WO2013066915A1 (en) | 2011-11-01 | 2013-05-10 | Exxonmobil Research And Engineering Company | Lubricants with improved low-temperature fuel economy |
WO2013070376A2 (en) | 2011-11-11 | 2013-05-16 | Vanderbilt Chemicals, Llc | Lubricant composition |
WO2013074498A1 (en) | 2011-11-14 | 2013-05-23 | Exxonmobil Research And Engineering Company | Method for improving engine fuel efficiency |
WO2013090051A1 (en) | 2011-12-13 | 2013-06-20 | Chemtura Corporation | Cross products and co-oligomers of phenylenediamines and aromatic amines as antioxidants for lubricants |
DE102012223638A1 (en) | 2011-12-21 | 2013-06-27 | Infineum International Ltd. | A method of reducing the rate of decrease of the basicity of a lubricating oil composition used in an engine |
WO2013096532A1 (en) | 2011-12-22 | 2013-06-27 | Exxonmobil Research And Engineering Company | Method for improving engine fuel efficiency |
WO2013101882A1 (en) | 2011-12-29 | 2013-07-04 | The Lubrizol Corporation | Limited slip friction modifiers for differentials |
EP2620207A2 (en) | 2008-10-31 | 2013-07-31 | Calera Corporation | Non-cementitious compositions comprising CO2 sequestering additives |
WO2013123102A2 (en) | 2012-02-17 | 2013-08-22 | The Lubrizol Corporation | Lubricating composition including esterified copolymer and low dispersant levels suitable for driveline applications |
WO2013123160A1 (en) | 2012-02-17 | 2013-08-22 | The Lubrizol Corporation | Mixtures of olefin-ester copolymer with polyolefin as viscosity modifier |
WO2013151911A1 (en) | 2012-04-04 | 2013-10-10 | The Lubrizol Corporation | Bearing lubricants for pulverizing equipment |
US8586520B2 (en) | 2011-06-30 | 2013-11-19 | Exxonmobil Research And Engineering Company | Method of improving pour point of lubricating compositions containing polyalkylene glycol mono ethers |
WO2013181318A1 (en) | 2012-06-01 | 2013-12-05 | Exxonmobil Research And Engineering Company | Lubricant compostions and processes for preparing same |
WO2014008121A1 (en) | 2012-07-02 | 2014-01-09 | Exxonmobil Research And Engineering Company | Enhanced durability performance of lubricants using functionalized metal phosphate nanoplatelets |
EP2687583A1 (en) | 2012-07-17 | 2014-01-22 | Infineum International Limited | Lubricating oil compositions containing sterically hindered amines as ashless TBN sources |
EP2692839A1 (en) | 2012-07-31 | 2014-02-05 | Infineum International Limited | A lubricating oil compostion comprising a corrosion inhibitor |
EP2692840A1 (en) | 2012-07-31 | 2014-02-05 | Infineum International Limited | Lubricating oil composition |
US20140066579A1 (en) * | 2007-07-18 | 2014-03-06 | Eni S.P.A. | Polyalkenyl succinimides and use thereof as dispersants in lubricating oils |
WO2014047017A1 (en) | 2012-09-24 | 2014-03-27 | The Lubrizol Corporation | Lubricant comprising a mixture of an olefin-ester copolymer with an ethylene alpha-olefin copolymer |
WO2014066444A1 (en) | 2012-10-24 | 2014-05-01 | Exxonmobil Research And Engineering Comapny | Functionalized polymers and oligomers as corrosion inhibitors and antiwear additives |
EP2727984A1 (en) | 2012-11-02 | 2014-05-07 | Infineum International Limited | Marine engine lubrication |
EP2735603A1 (en) | 2012-11-21 | 2014-05-28 | Infineum International Limited | Marine engine lubrication |
EP2740782A1 (en) | 2012-12-10 | 2014-06-11 | Infineum International Limited | Lubricating oil compositions containing sterically hindered amines as ashless tbn sources |
WO2014105312A1 (en) | 2012-12-28 | 2014-07-03 | Chevron Oronite Company Llc | Ultra-low saps lubricants for internal combustion engines |
WO2014107315A1 (en) | 2013-01-04 | 2014-07-10 | Exxonmobil Research And Engineering Company | Method for improving engine fuel efficiency |
EP2765179A1 (en) | 2013-02-07 | 2014-08-13 | Infineum International Limited | Marine engine lubrication |
WO2014137580A1 (en) | 2013-03-07 | 2014-09-12 | The Lubrizol Corporation | Limited slip friction modifiers for differentials |
WO2014158533A1 (en) | 2013-03-14 | 2014-10-02 | Exxonmobil Research And Engineering Company | Lubricating composition providing high wear resistance |
WO2014184068A1 (en) | 2013-05-14 | 2014-11-20 | Basf Se | Lubricating oil composition with enhanced energy efficiency |
WO2014184062A1 (en) | 2013-05-17 | 2014-11-20 | Basf Se | The use of polytetrahydrofuranes in lubricating oil compositions |
EP2851412A1 (en) | 2013-09-24 | 2015-03-25 | Infineum International Limited | Marine engine lubrication |
WO2015050690A1 (en) | 2013-10-03 | 2015-04-09 | Exxonmobil Research And Engineering Company | Compositions with improved varnish control properties |
WO2015078707A1 (en) | 2013-11-26 | 2015-06-04 | Basf Se | The use of polyalkylene glycol esters in lubricating oil compositions |
WO2015095336A1 (en) | 2013-12-18 | 2015-06-25 | Chevron Phillips Chemical Company Lp | Method for making polyolefins using aluminum halide catalyzed oligomerization of olefins |
WO2015099907A1 (en) | 2013-12-23 | 2015-07-02 | Exxonmobil Research And Engineering Company | Low viscosity ester lubricant and method for using |
WO2015099821A1 (en) | 2013-12-23 | 2015-07-02 | Exxonmobil Research And Engineering Company | Method for improving engine fuel efficiency |
WO2015099820A1 (en) | 2013-12-23 | 2015-07-02 | Exxonmobil Research And Engineering Company | Method for improving engine fuel efficiency |
WO2015099819A1 (en) | 2013-12-23 | 2015-07-02 | Exxonmobil Research And Engineering Company | Method for improving engine fuel efficiency |
EP2913384A1 (en) | 2014-02-26 | 2015-09-02 | Infineum International Limited | A lubricating oil composition |
WO2015134129A2 (en) | 2014-03-05 | 2015-09-11 | The Lubrizol Corporation | Emulsifier components and methods of using the same |
US9133581B2 (en) | 2008-10-31 | 2015-09-15 | Calera Corporation | Non-cementitious compositions comprising vaterite and methods thereof |
EP2937408A1 (en) | 2014-04-22 | 2015-10-28 | Basf Se | Lubricant composition comprising an ester of a C17 alcohol mixture |
EP2940110A1 (en) | 2014-04-29 | 2015-11-04 | Infineum International Limited | Lubricating oil compositions |
WO2015171980A1 (en) | 2014-05-09 | 2015-11-12 | Exxonmobil Research And Engineering Company | Method for preventing or reducing low speed pre-ignition |
WO2015171292A1 (en) | 2014-05-08 | 2015-11-12 | Exxonmobil Research And Engineering Company | Method for preventing or reducing engine knock and pre-ignition |
WO2015171981A1 (en) | 2014-05-09 | 2015-11-12 | Exxonmobil Research And Engineering Company | Method for preventing or reducing low speed pre-ignition |
WO2015171978A1 (en) | 2014-05-09 | 2015-11-12 | Exxonmobil Research And Engineering Company | Method for preventing or reducing low speed pre-ignition |
WO2015183455A1 (en) | 2014-05-29 | 2015-12-03 | Exxonmobil Research And Engineering Company | Lubricating oil compositions with engine wear protection |
WO2016043944A1 (en) | 2014-09-17 | 2016-03-24 | Exxonmobil Research And Engineering Company | Composition and method for preventing or reducing engine knock and pre-ignition in high compression spark ignition engines |
WO2016073149A1 (en) | 2014-11-03 | 2016-05-12 | Exxonmobil Research And Engineering Company | Low transition temperature mixtures or deep eutectic solvents and processes for preparation thereof |
EP3029133A1 (en) | 2014-12-04 | 2016-06-08 | Infineum International Limited | Marine engine lubrication |
EP3034587A1 (en) | 2014-12-19 | 2016-06-22 | Infineum International Limited | Marine engine lubrication |
WO2016106211A1 (en) | 2014-12-24 | 2016-06-30 | Exxonmobil Research And Engineering Company | Methods for authentication and identification of petroleum products |
WO2016106214A1 (en) | 2014-12-24 | 2016-06-30 | Exxonmobil Research And Engineering Company | Methods for determining condition and quality of petroleum products |
WO2016109376A1 (en) | 2014-12-30 | 2016-07-07 | Exxonmobil Research And Engineering Company | Lubricating oil compositions with engine wear protection |
WO2016109322A1 (en) | 2014-12-30 | 2016-07-07 | Exxonmobil Research And Engineering Company | Lubricating oil compositions containing encapsulated microscale particles |
WO2016109382A1 (en) | 2014-12-30 | 2016-07-07 | Exxonmobil Research And Engineering Company | Lubricating oil compositions with engine wear protection |
WO2016138939A1 (en) | 2015-03-03 | 2016-09-09 | Basf Se | Pib as high viscosity lubricant base stock |
EP3085757A1 (en) | 2015-04-23 | 2016-10-26 | Basf Se | Stabilization of alkoxylated polytetrahydrofuranes with antioxidants |
US9506008B2 (en) | 2013-12-23 | 2016-11-29 | Exxonmobil Research And Engineering Company | Method for improving engine fuel efficiency |
WO2016191409A1 (en) | 2015-05-28 | 2016-12-01 | Exxonmobil Research And Engineering Company | Composition and method for preventing or reducing engine knock and pre-ignition in high compression spark ignition engines |
WO2016200606A1 (en) | 2015-06-09 | 2016-12-15 | Exxonmobil Research And Engineering Company | Inverse micellar compositions containing lubricant additives |
WO2017007670A1 (en) | 2015-07-07 | 2017-01-12 | Exxonmobil Research And Engineering Company | Composition and method for preventing or reducing engine knock and pre-ignition in high compression spark ignition engines |
EP3124581A1 (en) | 2015-07-30 | 2017-02-01 | Infineum International Limited | Dispersant additives and additive concentrates and lubricating oil compositions containing same |
EP3135750A1 (en) | 2015-08-26 | 2017-03-01 | Infineum International Limited | Lubricating oil compositions |
EP3144372A1 (en) | 2015-09-16 | 2017-03-22 | Infineum International Limited | Additive concentrates for the formulation of lubricating oil compositions |
EP3153568A1 (en) | 2015-10-05 | 2017-04-12 | Infineum International Limited | Additive concentrates for the formulation of lubricating oil compositions |
WO2017117178A1 (en) | 2015-12-28 | 2017-07-06 | Exxonmobil Research And Engineering Company | Bright stock production from deasphalted oil |
EP3192858A1 (en) | 2016-01-15 | 2017-07-19 | Infineum International Limited | Use of lubricating oil composition |
US9732300B2 (en) | 2015-07-23 | 2017-08-15 | Chevron Phillipa Chemical Company LP | Liquid propylene oligomers and methods of making same |
WO2017146897A1 (en) | 2016-02-26 | 2017-08-31 | Exxonmobil Research And Engineering Company | Lubricant compositions containing controlled release additives |
WO2017146896A1 (en) | 2016-02-26 | 2017-08-31 | Exxonmobil Research And Engineering Company | Lubricant compositions containing controlled release additives |
EP3222698A1 (en) | 2016-03-22 | 2017-09-27 | Infineum International Limited | Additive concentrates |
US9775350B2 (en) | 2004-10-14 | 2017-10-03 | Koppers Performance Chemicals Inc. | Micronized wood preservative formulations in organic carriers |
WO2017172254A1 (en) | 2016-03-31 | 2017-10-05 | Exxonmobil Research And Engineering Company | Lubricant compositions |
EP3249029A1 (en) | 2016-05-23 | 2017-11-29 | Infineum International Limited | Highly borated dispersant concentrates for lubricating oil compositions and methods for forming same |
EP3252130A1 (en) | 2016-06-03 | 2017-12-06 | Infineum International Limited | Additive package and lubricating oil composition |
EP3257921A1 (en) | 2016-06-14 | 2017-12-20 | Infineum International Limited | Lubricating oil additives |
EP3263676A2 (en) | 2016-06-30 | 2018-01-03 | Infineum International Limited | Lubricating oil compositions |
WO2018013249A1 (en) | 2016-07-12 | 2018-01-18 | Chevron Phillips Chemical Company Lp | Decene oligomers |
US9879202B2 (en) | 2014-12-04 | 2018-01-30 | Infineum International Limited | Marine engine lubrication |
US9885004B2 (en) | 2013-12-23 | 2018-02-06 | Exxonmobil Research And Engineering Company | Method for improving engine fuel efficiency |
WO2018027227A1 (en) | 2016-08-05 | 2018-02-08 | Rutgers, The State University Of New Jersey | Thermocleavable friction modifiers and methods thereof |
WO2018026982A1 (en) | 2016-08-03 | 2018-02-08 | Exxonmobil Research And Engineering Company | Lubricating engine oil for improved wear protection and fuel efficiency |
US20180044610A1 (en) * | 2015-03-09 | 2018-02-15 | The Lubrizol Corporation | Method Of Lubricating An Internal Combustion Engine |
US20180066203A1 (en) * | 2014-05-09 | 2018-03-08 | Exxonmobil Research And Engineering Company | Method for preventing or reducing low speed pre-ignition while maintaining or improving cleanliness |
US9914893B2 (en) | 2014-01-28 | 2018-03-13 | Basf Se | Use of alkoxylated polyethylene glycols in lubricating oil compositions |
EP3293246A1 (en) | 2016-09-13 | 2018-03-14 | Basf Se | Lubricant compositions containing diurea compounds |
WO2018053098A1 (en) | 2016-09-14 | 2018-03-22 | The Lubrizol Corporation | Lubricating composition comprising sulfonate detergent and ashless hydrocarbyl phenolic compound |
US9926509B2 (en) | 2015-01-19 | 2018-03-27 | Exxonmobil Research And Engineering Company | Lubricating oil compositions with engine wear protection and solubility |
WO2018057377A1 (en) | 2016-09-20 | 2018-03-29 | Exxonmobil Research And Engineering Company | Non-newtonian engine oil with superior engine wear protection and fuel economy |
WO2018067902A1 (en) | 2016-10-07 | 2018-04-12 | Exxonmobil Research And Engineering Company | Lubricating oil compositions for electric vehicle powertrains |
WO2018067903A1 (en) | 2016-10-07 | 2018-04-12 | Exxonmobil Research And Engineering Company | Method for controlling electrical conductivity of lubricating oils in electric vehicle powertrains |
WO2018067905A1 (en) | 2016-10-07 | 2018-04-12 | Exxonmobil Research And Engineering Company | Method for preventing or minimizing electrostatic discharge and dielectric breakdown in electric vehicle powertrains |
EP3315591A1 (en) | 2016-10-28 | 2018-05-02 | Basf Se | Energy efficient lubricant compositions |
EP3321347A1 (en) | 2016-11-14 | 2018-05-16 | Infineum International Limited | Lubricating oil additives based on overbased gemini surfactant |
US10000720B2 (en) | 2014-05-22 | 2018-06-19 | Basf Se | Lubricant compositions containing beta-glucans |
EP3339404A1 (en) | 2006-07-18 | 2018-06-27 | Infineum International Limited | Lubricating oil compositions |
WO2018118477A1 (en) | 2016-12-19 | 2018-06-28 | Exxonmobil Research And Engineering Company | Composition and method for preventing or reducing engine knock and pre-ignition compression spark ignition engines |
WO2018125956A1 (en) | 2016-12-30 | 2018-07-05 | Exxonmobil Research And Engineering Company | Low viscosity lubricating oil compositions for turbomachines |
WO2018144166A1 (en) | 2017-02-01 | 2018-08-09 | Exxonmobil Research And Engineering Company | Lubricating engine oil and method for improving engine fuel efficiency |
EP3366755A1 (en) | 2017-02-22 | 2018-08-29 | Infineum International Limited | Improvements in and relating to lubricating compositions |
WO2018156304A1 (en) | 2017-02-21 | 2018-08-30 | Exxonmobil Research And Engineering Company | Lubricating oil compositions and methods of use thereof |
EP3369802A1 (en) | 2017-03-01 | 2018-09-05 | Infineum International Limited | Improvements in and relating to lubricating compositions |
WO2018170110A1 (en) | 2017-03-16 | 2018-09-20 | Chevron Phillips Chemical Company Lp | Lubricant compositions containing hexene-based oligomers |
WO2018175830A1 (en) | 2017-03-24 | 2018-09-27 | Exxonmobil Research And Engineering Company | Method for improving engine fuel efficiency and energy efficiency |
WO2018197312A1 (en) | 2017-04-27 | 2018-11-01 | Shell Internationale Research Maatschappij B.V. | Lubricating composition |
US10150928B2 (en) | 2013-09-16 | 2018-12-11 | Basf Se | Polyester and use of polyester in lubricants |
EP3421576A1 (en) | 2017-06-30 | 2019-01-02 | Infineum International Limited | Refinery antifoulant process |
WO2019014092A1 (en) | 2017-07-13 | 2019-01-17 | Exxonmobil Research And Engineering Company | Continuous process for the manufacture of grease |
WO2019018145A1 (en) | 2017-07-21 | 2019-01-24 | Exxonmobil Research And Engineering Company | Method for improving deposit control and cleanliness performance in an engine lubricated with a lubricating oil |
US10190072B2 (en) | 2013-12-23 | 2019-01-29 | Exxonmobil Research And Engineering Company | Method for improving engine fuel efficiency |
EP3434755A1 (en) | 2017-07-24 | 2019-01-30 | Infineum International Limited | Motorcycle lubricant |
WO2019028310A1 (en) | 2017-08-04 | 2019-02-07 | Exxonmobil Research And Engineering Company | Novel formulation for lubrication of hyper compressors providing improved pumpability under high-pressure conditions |
WO2019055291A1 (en) | 2017-09-18 | 2019-03-21 | Exxonmobil Research And Engineering Company | Hydraulic oil compositions with improved hydrolytic and thermo-oxidative stability |
WO2019060144A1 (en) | 2017-09-22 | 2019-03-28 | Exxonmobil Research And Engineering Company | Lubricating oil compositions with viscosity and deposit control |
EP3461877A1 (en) | 2017-09-27 | 2019-04-03 | Infineum International Limited | Improvements in and relating to lubricating compositions |
EP3470499A1 (en) | 2017-10-16 | 2019-04-17 | Infineum International Limited | Use of detergent for internal compustion engine oil compositions |
EP3473694A1 (en) | 2017-10-12 | 2019-04-24 | Infineum International Limited | Lubricating oil compositions |
WO2019089180A1 (en) | 2017-10-30 | 2019-05-09 | Exxonmobil Research And Engineering Company | Lubricating oil compositions having improved cleanliness and wear performance |
WO2019090038A1 (en) | 2017-11-03 | 2019-05-09 | Exxonmobil Research And Engineering Company | Lubricant compositions with improved performance and methods of preparing and using the same |
WO2019094019A1 (en) | 2017-11-09 | 2019-05-16 | Exxonmobil Research And Engineering Company | Method for preventing or reducing low speed pre-ignition while maintaining or improving cleanliness |
WO2019103808A1 (en) | 2017-11-22 | 2019-05-31 | Exxonmobil Research And Engineering Company | Lubricating oil compositions with oxidative stability in diesel engines |
EP3492566A1 (en) | 2017-11-29 | 2019-06-05 | Infineum International Limited | Lubricating oil additives |
EP3492567A1 (en) | 2017-11-29 | 2019-06-05 | Infineum International Limited | Lubricating oil additives |
US10316712B2 (en) | 2015-12-18 | 2019-06-11 | Exxonmobil Research And Engineering Company | Lubricant compositions for surface finishing of materials |
EP3495462A1 (en) | 2017-12-11 | 2019-06-12 | Infineum International Limited | Low ash and ash-free acid neutralizing compositions and lubricating oil compositions containing same |
WO2019112711A1 (en) | 2017-12-04 | 2019-06-13 | Exxonmobil Research And Enginerring Company | Method for preventing or reducing low speed pre-ignition |
WO2019118115A1 (en) | 2017-12-15 | 2019-06-20 | Exxonmobil Research And Engineering Company | Lubricating oil compositions containing microencapsulated additives |
EP3502217A1 (en) | 2017-11-29 | 2019-06-26 | Infineum International Limited | Lubricating oil compositions |
WO2019133409A1 (en) | 2017-12-28 | 2019-07-04 | Exxonmobil Research And Engineering Company | Friction and wear reduction using liquid crystal base stocks |
WO2019133218A1 (en) | 2017-12-29 | 2019-07-04 | Exxonmobil Research And Engineering Company | Lubricating oil compositions with wear and sludge control |
WO2019133191A1 (en) | 2017-12-29 | 2019-07-04 | Exxonmobil Research And Engineering Company | Lubrication of oxygenated diamond-like carbon surfaces |
WO2019133255A1 (en) | 2017-12-29 | 2019-07-04 | Exxonmobil Research And Engineering Company | Grease compositions with improved performance comprising thixotropic polyamide, and methods of preparing and using the same |
US10364404B2 (en) | 2014-12-04 | 2019-07-30 | Infineum International Limited | Marine engine lubrication |
EP3546549A1 (en) | 2018-03-27 | 2019-10-02 | Infineum International Limited | Lubricating oil composition |
US10435491B2 (en) | 2015-08-19 | 2019-10-08 | Chevron Phillips Chemical Company Lp | Method for making polyalphaolefins using ionic liquid catalyzed oligomerization of olefins |
WO2019217058A1 (en) | 2018-05-11 | 2019-11-14 | Exxonmobil Research And Engineering Company | Method for improving engine fuel efficiency |
US10494579B2 (en) | 2016-04-26 | 2019-12-03 | Exxonmobil Research And Engineering Company | Naphthene-containing distillate stream compositions and uses thereof |
WO2019240965A1 (en) | 2018-06-11 | 2019-12-19 | Exxonmobil Research And Engineering Company | Non-zinc-based antiwear compositions, hydraulic oil compositions, and methods of using the same |
WO2020023430A1 (en) | 2018-07-23 | 2020-01-30 | Exxonmobil Research And Engineering Company | Lubricating oil compositions with oxidative stability in diesel engines using biodiesel fuel |
WO2020023437A1 (en) | 2018-07-24 | 2020-01-30 | Exxonmobil Research And Engineering Company | Lubricating oil compositions with engine corrosion protection |
US10550341B2 (en) | 2015-12-28 | 2020-02-04 | Exxonmobil Research And Engineering Company | Sequential deasphalting for base stock production |
US10550335B2 (en) | 2015-12-28 | 2020-02-04 | Exxonmobil Research And Engineering Company | Fluxed deasphalter rock fuel oil blend component oils |
WO2020033232A1 (en) | 2018-08-06 | 2020-02-13 | The Lubrizol Corporation | Composition and method for lubricating automotive gears, axles and bearings |
WO2020068439A1 (en) | 2018-09-27 | 2020-04-02 | Exxonmobil Research And Engineering Company | Low viscosity lubricating oils with improved oxidative stability and traction performance |
US10647936B2 (en) | 2016-12-30 | 2020-05-12 | Exxonmobil Research And Engineering Company | Method for improving lubricant antifoaming performance and filterability |
WO2020096804A1 (en) | 2018-11-05 | 2020-05-14 | Exxonmobil Research And Engineering Company | Lubricating oil compositions having improved cleanliness and wear performance |
US10662391B2 (en) | 2017-02-21 | 2020-05-26 | Chevron Oronite Company Llc | Lubricating oil compositions containing borated dispersants and amine compounds and methods of making and using same |
WO2020112338A1 (en) | 2018-11-28 | 2020-06-04 | Exxonmobil Research And Engineering Company | Lubricating oil compositions with improved deposit resistance and methods thereof |
WO2020123440A1 (en) | 2018-12-10 | 2020-06-18 | Exxonmobil Research And Engineering Company | Method for improving oxidation and deposit resistance of lubricating oils |
US10689593B2 (en) | 2014-08-15 | 2020-06-23 | Exxonmobil Research And Engineering Company | Low viscosity lubricating oil compositions for turbomachines |
WO2020131310A1 (en) | 2018-12-19 | 2020-06-25 | Exxonmobil Research And Engineering Company | Method for improving high temperature antifoaming performance of a lubricating oil |
WO2020131440A1 (en) | 2018-12-19 | 2020-06-25 | Exxonmobil Research And Engineering Company | Grease compositions having calcium sulfonate and polyurea thickeners |
WO2020132166A1 (en) | 2018-12-19 | 2020-06-25 | Exxonmobil Research And Engineering Company | Lubricating oil compositions with antioxidant formation and dissipation control |
WO2020131515A2 (en) | 2018-12-19 | 2020-06-25 | Exxonmobil Research And Engineering Company | Lubricant compositions with improved wear control |
WO2020131441A1 (en) | 2018-12-19 | 2020-06-25 | Exxonmobil Research And Engineering Company | Grease compositions having improved performance |
WO2020132164A1 (en) | 2018-12-19 | 2020-06-25 | Exxonmobil Research And Engineering Company | Lubricating oil compositions with viscosity control |
WO2020131439A1 (en) | 2018-12-19 | 2020-06-25 | Exxonmobil Research And Engineering Company | Grease compositions having polyurea thickeners made with isocyanate terminated prepolymers |
WO2020139333A1 (en) | 2018-12-26 | 2020-07-02 | Exxonmobil Research And Engineering Company | Formulation approach to extend the high temperature performance of lithium complex greases |
US10712105B1 (en) | 2019-06-19 | 2020-07-14 | Exxonmobil Research And Engineering Company | Heat transfer fluids and methods of use |
WO2020150123A1 (en) | 2019-01-17 | 2020-07-23 | The Lubrizol Corporation | Traction fluids |
WO2020176171A1 (en) | 2019-02-28 | 2020-09-03 | Exxonmobil Research And Engineering Company | Low viscosity gear oil compositions for electric and hybrid vehicles |
US10781397B2 (en) | 2014-12-30 | 2020-09-22 | Exxonmobil Research And Engineering Company | Lubricating oil compositions with engine wear protection |
US10793801B2 (en) | 2017-02-06 | 2020-10-06 | Exxonmobil Chemical Patents Inc. | Low transition temperature mixtures and lubricating oils containing the same |
US10808196B2 (en) | 2017-03-28 | 2020-10-20 | Exxonmobil Chemical Patents Inc. | Cold cranking simulator viscosity reducing base stocks and lubricating oil formulations containing the same |
EP3741832A2 (en) | 2019-05-24 | 2020-11-25 | Infineum International Limited | Nitrogen-containing lubricating oil additives |
US10858610B2 (en) | 2017-03-24 | 2020-12-08 | Exxonmobil Chemical Patents Inc. | Cold cranking simulator viscosity boosting base stocks and lubricating oil formulations containing the same |
WO2020257376A1 (en) | 2019-06-19 | 2020-12-24 | Exxonmobil Research And Engineering Company | Heat transfer fluids and methods of use |
WO2020257377A1 (en) | 2019-06-19 | 2020-12-24 | Exxonmobil Research And Engineering Company | Heat transfer fluids and methods of use |
WO2020257370A1 (en) | 2019-06-19 | 2020-12-24 | Exxonmobil Research And Engineering Company | Heat transfer fluids and methods of use |
WO2020257374A1 (en) | 2019-06-19 | 2020-12-24 | Exxonmobil Research And Engineering Company | Heat transfer fluids and methods of use |
WO2020257371A1 (en) | 2019-06-19 | 2020-12-24 | Exxonmobil Research And Engineering Company | Heat transfer fluids and methods of use |
WO2020257373A1 (en) | 2019-06-19 | 2020-12-24 | Exxonmobil Research And Engineering Company | Heat transfer fluids and methods of use |
WO2020257375A1 (en) | 2019-06-19 | 2020-12-24 | Exxonmobil Research And Engineering Company | Heat transfer fluids and methods of use |
WO2020257378A1 (en) | 2019-06-19 | 2020-12-24 | Exxonmobil Research And Engineering Company | Heat transfer fluids and methods of use |
WO2020257379A1 (en) | 2019-06-19 | 2020-12-24 | Exxonmobil Research And Engineering Company | Heat transfer fluids and methods of use |
US10876062B2 (en) | 2017-03-24 | 2020-12-29 | Exxonmobil Chemical Patents Inc. | Cold cranking simulator viscosity boosting base stocks and lubricating oil formulations containing the same |
WO2020264534A2 (en) | 2019-06-27 | 2020-12-30 | Exxonmobil Research And Engineering Company | Method for reducing solubilized copper levels in wind turbine gear oils |
EP3760696A1 (en) | 2018-12-20 | 2021-01-06 | Infineum International Limited | Oil anti-foulant and/or asphaltene agglomeration process |
EP3770235A1 (en) | 2018-09-24 | 2021-01-27 | Infineum International Limited | Polymers and lubricating compositions containing polymers |
EP3778841A1 (en) | 2019-08-15 | 2021-02-17 | Infineum International Limited | Method for reducing piston deposits in a marine diesel engine |
EP3835392A1 (en) | 2018-12-20 | 2021-06-16 | Infineum International Limited | Hydrocarbon marine fuel oil |
WO2021138285A1 (en) | 2020-01-03 | 2021-07-08 | Afton Chemical Corporation | Silicone functionlized viscosity index improver |
EP3851507A1 (en) | 2020-01-15 | 2021-07-21 | Infineum International Limited | Polymers and lubricating compositions containing polymers |
WO2021154497A1 (en) | 2020-01-30 | 2021-08-05 | Exxonmobil Research And Engineering Company | Sulfur-free, ashless, low phosphorus lubricant compositions with improved oxidation stability |
EP3882330A1 (en) | 2020-03-20 | 2021-09-22 | Chevron Japan Ltd. | Low viscosity lubricating oil composition |
WO2021194813A1 (en) | 2020-03-27 | 2021-09-30 | Exxonmobil Research And Engineering Company | Monitoring health of heat transfer fluids for electric systems |
EP3926026A1 (en) | 2020-06-16 | 2021-12-22 | Infineum International Limited | Oil compositions |
WO2022010606A1 (en) | 2020-07-09 | 2022-01-13 | Exxonmobil Research And Engineering Company | Engine oil lubricant compositions and methods for making same with superior engine wear protection and corrosion protection |
WO2022018624A1 (en) | 2020-07-21 | 2022-01-27 | Chevron Japan Ltd. | Magnesium and boron containing lubricating oil composition for hybrid vehicles |
WO2022072962A1 (en) | 2020-09-30 | 2022-04-07 | Exxonmobil Research And Engineering Company | Low friction and low traction lubricant compositions useful in dry clutch motorcycles |
US11299690B2 (en) | 2016-03-22 | 2022-04-12 | Infineum International Ltd. | Additive concentrates |
WO2022099291A1 (en) | 2020-11-06 | 2022-05-12 | Exxonmobil Research And Engineering Company | Engine oil lubricant compositions and methods for making same with steel corrosion protection |
WO2022112899A1 (en) | 2020-11-25 | 2022-06-02 | Chevron Japan Ltd. | Lubricating oil compositions |
EP4159832A1 (en) | 2021-10-04 | 2023-04-05 | Infineum International Limited | Lubricating oil compositions |
EP4174152A1 (en) | 2021-10-29 | 2023-05-03 | Infineum International Limited | Ionic liquid composition |
EP4174153A1 (en) | 2021-10-29 | 2023-05-03 | Infineum International Limited | Method of limiting chemical degradation due to nitrogen dioxide contamination |
EP4174154A1 (en) | 2021-10-29 | 2023-05-03 | Infineum International Limited | Method of limiting chemical degradation due to nitrogen dioxide contamination |
EP4180505A1 (en) | 2021-11-15 | 2023-05-17 | Infineum International Limited | Improvements in marine fuels |
WO2023122405A1 (en) | 2021-12-21 | 2023-06-29 | ExxonMobil Technology and Engineering Company | Engine oil lubricant compostions and methods for making same with superior oil consumption |
US11760952B2 (en) | 2021-01-12 | 2023-09-19 | Ingevity South Carolina, Llc | Lubricant thickener systems from modified tall oil fatty acids, lubricating compositions, and associated methods |
EP4303287A1 (en) | 2022-07-06 | 2024-01-10 | Infineum International Limited | Lubricating oil compositions |
EP4353804A1 (en) | 2022-10-11 | 2024-04-17 | Infineum International Limited | Functionalized c4 to c5 olefin polymers and lubricant compositions containing such |
EP4353805A1 (en) | 2022-10-11 | 2024-04-17 | Infineum International Limited | Lubricant composition containing metal alkanoate |
EP4357443A1 (en) | 2022-10-18 | 2024-04-24 | Infineum International Limited | Lubricating oil compositions |
Families Citing this family (127)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3533945A (en) * | 1963-11-13 | 1970-10-13 | Lubrizol Corp | Lubricating oil composition |
US3929650A (en) * | 1974-03-22 | 1975-12-30 | Chevron Res | Extreme pressure agent and its preparation |
IT1025257B (en) * | 1974-10-28 | 1978-08-10 | Liquichimica Spa | DISPERSING ADDITIVE FOR LUBRICANT OILS AND PROCEDURE FOR THE RELATIVE PRODUCTION |
FR2307845A1 (en) * | 1975-04-18 | 1976-11-12 | Orogil | NEW COMPOSITIONS BASED ON ALCENYLSUCCINIMIDES AS ADDITIVES FOR LUBRICATING OILS |
US5162526A (en) * | 1976-09-24 | 1992-11-10 | Exxon Chemical Patents Inc. | Macrocyclic polyamine and polycyclic polyamine multifunctional lubricating oil |
US4116876A (en) * | 1977-01-28 | 1978-09-26 | Exxon Research & Engineering Co. | Borated oxazolines as varnish inhibiting dispersants in lubricating oils |
US4173540A (en) * | 1977-10-03 | 1979-11-06 | Exxon Research & Engineering Co. | Lubricating oil composition containing a dispersing-varnish inhibiting combination of polyol ester compound and a borated acyl nitrogen compound |
CA1125735A (en) * | 1978-09-18 | 1982-06-15 | Esther D. Winans | Molybdenum complexes of ashless nitrogen dispersants as friction reducing antiwear additives for lubricating oils |
US4331545A (en) * | 1979-04-19 | 1982-05-25 | Edwin Cooper, Inc. | Lubricating compositions containing boronated N-alkanol hydrocarbylamide |
US4328113A (en) * | 1980-01-14 | 1982-05-04 | Mobil Oil Corporation | Friction reducing additives and compositions thereof |
US4505829A (en) * | 1980-05-08 | 1985-03-19 | Exxon Research & Engineering Co. | Lubricating oil composition containing sediment-reducing additive |
DE3163160D1 (en) | 1980-05-08 | 1984-05-24 | Exxon Research Engineering Co | Lubricating oil composition containing sediment-reducing additive |
US4426305A (en) | 1981-03-23 | 1984-01-17 | Edwin Cooper, Inc. | Lubricating compositions containing boronated nitrogen-containing dispersants |
US4374033A (en) * | 1981-06-18 | 1983-02-15 | Edwin Cooper, Inc. | Dispersant and lubricating oil containing the dispersant |
FR2510598A1 (en) * | 1981-07-30 | 1983-02-04 | Inst Francais Du Petrole | USE OF NITROGEN ADDITIVES AS DISORDERS OF HYDROCARBON MEDIUM DISTILLATE DISORDER POINT AND HYDROCARBON MEDIUM DISTILLATE COMPOSITIONS COMPRISING SUCH ADDITIVES |
US4581038A (en) * | 1981-09-01 | 1986-04-08 | The Lubrizol Corporation | Acylated ether amine and lubricants and fuels containing the same |
EP0074199B1 (en) * | 1981-09-01 | 1986-11-12 | The Lubrizol Corporation | Acylated ether amine and lubricants and fuels containing the same |
EP0086049B1 (en) * | 1982-02-03 | 1986-12-17 | The Lubrizol Corporation | Compositions for use in alcohol and alcohol containing fuels |
US4873009A (en) * | 1982-03-29 | 1989-10-10 | Amoco Corporation | Borated lube oil additive |
CA1199318A (en) * | 1982-03-29 | 1986-01-14 | Amoco Corporation | Borated lube oil additive |
FR2528423B1 (en) * | 1982-06-10 | 1987-07-24 | Inst Francais Du Petrole | NITROGEN ADDITIVES FOR USE AS DISORDERS TO REDUCE THE POINT OF MEDIUM HYDROCARBON DISTILLATES AND COMPOSITIONS OF MEDIUM HYDROCARBON DISTILLATES CONTAINING THE ADDITIVES |
JPS59122597A (en) * | 1982-11-30 | 1984-07-16 | Honda Motor Co Ltd | Lubricating oil composition |
US4455243A (en) * | 1983-02-24 | 1984-06-19 | Chevron Research Company | Succinimide complexes of borated fatty acid esters of glycerol and lubricating oil compositions containing same |
CA1224470A (en) * | 1983-02-24 | 1987-07-21 | Thomas V. Liston | Succinimide complexes of borated fatty acid esters of glycerol and lubricating compositions containing same |
CA1235977A (en) * | 1983-07-25 | 1988-05-03 | Robert J. Basalay | Boration of polyamine dispersants with polyborate esters |
US4612129A (en) | 1985-01-31 | 1986-09-16 | The Lubrizol Corporation | Sulfur-containing compositions, and additive concentrates and lubricating oils containing same |
GB8602627D0 (en) * | 1986-02-04 | 1986-03-12 | Exxon Chemical Patents Inc | Marine lubricating composition |
GB8628523D0 (en) * | 1986-11-28 | 1987-01-07 | Shell Int Research | Lubricating composition |
GB8804171D0 (en) * | 1988-02-23 | 1988-03-23 | Exxon Chemical Patents Inc | Dispersant for marine diesel cylinder lubricant |
US5164103A (en) * | 1988-03-14 | 1992-11-17 | Ethyl Petroleum Additives, Inc. | Preconditioned atf fluids and their preparation |
US5242612A (en) * | 1988-06-24 | 1993-09-07 | Exxon Chemical Patents Inc. | Mixed phosphorous- and sulfur-containing reaction products useful in power transmitting compositions |
US5326487A (en) * | 1988-06-24 | 1994-07-05 | Exxon Chemical Patents Inc. | Mixed phosphorous- and sulfur- containing reaction products useful in power transmitting compositions |
US5534170A (en) * | 1988-06-24 | 1996-07-09 | Exxon Chemical Patents Inc. | Mixed phosphorus- and sulfur-containing reaction products useful in power transmitting compositions |
US5314633A (en) * | 1988-06-24 | 1994-05-24 | Exxon Chemical Patents Inc. | Low pressure derived mixed phosphorous- and sulfur- containing reaction products useful in power transmitting compositions and process for preparing same |
US5320768A (en) * | 1988-06-24 | 1994-06-14 | Exxon Chemical Patents Inc. | Hydroxy ether amine friction modifier for use in power transmission fluids and anti-wear additives for use in combination therewith |
EP0360394A3 (en) * | 1988-09-21 | 1992-03-18 | Imperial Chemical Industries Plc | Water-in-oil emulsion explosive |
US4981492A (en) * | 1989-12-13 | 1991-01-01 | Mobil Oil Corporation | Borated triazole-substituted polyalkenyl succinimides as multifunctional lubricant and fuel additives |
US5176840A (en) * | 1990-02-16 | 1993-01-05 | Ethyl Petroleum Additives, Inc. | Gear oil additive composition and gear oil containing the same |
CA2040819A1 (en) * | 1990-05-17 | 1991-11-18 | Stephen Norman | Lubricant compositions |
US5024677A (en) * | 1990-06-11 | 1991-06-18 | Nalco Chemical Company | Corrosion inhibitor for alcohol and gasohol fuels |
US5232616A (en) * | 1990-08-21 | 1993-08-03 | Chevron Research And Technology Company | Lubricating compositions |
US5344467A (en) * | 1991-05-13 | 1994-09-06 | The Lubrizol Corporation | Organometallic complex-antioxidant combinations, and concentrates and diesel fuels containing same |
US5360459A (en) * | 1991-05-13 | 1994-11-01 | The Lubrizol Corporation | Copper-containing organometallic complexes and concentrates and diesel fuels containing same |
IL100669A0 (en) * | 1991-05-13 | 1992-09-06 | Lubrizol Corp | Low-sulfur diesel fuel containing organometallic complexes |
TW230781B (en) * | 1991-05-13 | 1994-09-21 | Lubysu Co | |
US5376154A (en) * | 1991-05-13 | 1994-12-27 | The Lubrizol Corporation | Low-sulfur diesel fuels containing organometallic complexes |
US5227082A (en) * | 1991-12-23 | 1993-07-13 | Exxon Research And Engineering Company | Lubricating oil having improved rust inhibition and demulsibility |
US5211834A (en) * | 1992-01-31 | 1993-05-18 | Betz Laboratories, Inc. | Method for controlling fouling deposit formation in a liquid hydrocarbonaceous medium using boronated derivatives of polyalkenylsuccinimides |
FR2699550B1 (en) * | 1992-12-17 | 1995-01-27 | Inst Francais Du Petrole | Composition of petroleum middle distillate containing nitrogenous additives usable as agents limiting the rate of sedimentation of paraffins. |
CA2130139C (en) * | 1993-08-20 | 2004-06-29 | Sean S. Bigelow | Lubricating compositions with improved thermal stability and limited slip performance |
JPH07316577A (en) * | 1994-05-20 | 1995-12-05 | Tonen Corp | Lubricant oil composition |
AU688922B2 (en) * | 1994-06-16 | 1998-03-19 | Exxon Chemical Limited | Multigrade lubricating compositions containing no viscosity modifier |
GB2293389A (en) | 1994-09-26 | 1996-03-27 | Ethyl Petroleum Additives Ltd | Mixed zinc salt lubricant additives |
WO1996017912A1 (en) * | 1994-12-09 | 1996-06-13 | Exxon Chemical Patents Inc. | Synergistic antioxidant systems |
US6855675B1 (en) * | 1995-05-24 | 2005-02-15 | Tonengeneral Sekiyu K.K. | Lubricating oil composition |
US6077455A (en) | 1995-07-17 | 2000-06-20 | Exxon Chemical Patents Inc | Automatic transmission fluid of improved viscometric properties |
GB2307685B (en) * | 1995-12-01 | 1999-07-07 | Ethyl Petroleum Additives Ltd | Seal compatible diesel dispersants |
US6613722B1 (en) * | 1997-03-07 | 2003-09-02 | Exxon Chemical Patents Inc. | Lubricating composition |
FR2762006B1 (en) * | 1997-04-11 | 2003-09-12 | Chevron Res & Tech | USE OF HIGH MOLECULAR WEIGHT SURFACTANTS AS AGREEMENTS TO IMPROVE FILTERABILITY IN HYDRAULIC LUBRICANTS |
US6127323A (en) | 1997-04-21 | 2000-10-03 | Exxon Chemical Patents Inc. | Power transmission fluids containing alkyl phosphonates |
US6042626A (en) * | 1997-08-01 | 2000-03-28 | Ethyl Corporation | Phosphorylated and/or boronated dispersants as thermal stability additives for distillate fuels |
US5885943A (en) * | 1997-12-18 | 1999-03-23 | Exxon Chemical Patents Inc. | Sulfur boron antiwear agents for lubricating compositions |
US6001780A (en) * | 1998-06-30 | 1999-12-14 | Chevron Chemical Company Llc | Ashless lubricating oil formulation for natural gas engines |
US6361573B1 (en) * | 1999-08-31 | 2002-03-26 | Ethyl Corporation | Fuel dispersants with enhanced lubricity |
JP4015355B2 (en) * | 2000-09-29 | 2007-11-28 | 新日本石油株式会社 | Lubricating oil composition |
US6677281B2 (en) | 2001-04-20 | 2004-01-13 | Exxonmobil Research And Engineering Company | Synergistic combination of metallic and ashless rust inhibitors to yield improved rust protection and demulsibility in dispersant-containing lubricants |
US7112230B2 (en) | 2001-09-14 | 2006-09-26 | Afton Chemical Intangibles Llc | Fuels compositions for direct injection gasoline engines |
US6689723B2 (en) | 2002-03-05 | 2004-02-10 | Exxonmobil Chemical Patents Inc. | Sulfide- and polysulfide-containing lubricating oil additive compositions and lubricating compositions containing the same |
US20040214729A1 (en) | 2003-04-25 | 2004-10-28 | Buitrago Juan A. | Gear oil composition having improved copper corrosion properties |
US20050070446A1 (en) * | 2003-09-25 | 2005-03-31 | Ethyl Petroleum Additives, Inc. | Boron free automotive gear oil |
US20050250656A1 (en) * | 2004-05-04 | 2005-11-10 | Masahiro Ishikawa | Continuously variable transmission fluid |
US20060063685A1 (en) | 2004-09-22 | 2006-03-23 | Pieter Purmer | Lubricant for manual or automated manual transmissions |
US7485734B2 (en) * | 2005-01-28 | 2009-02-03 | Afton Chemical Corporation | Seal swell agent and process therefor |
US20060264339A1 (en) * | 2005-05-19 | 2006-11-23 | Devlin Mark T | Power transmission fluids with enhanced lifetime characteristics |
US20070042916A1 (en) * | 2005-06-30 | 2007-02-22 | Iyer Ramnath N | Methods for improved power transmission performance and compositions therefor |
US20070000745A1 (en) * | 2005-06-30 | 2007-01-04 | Cameron Timothy M | Methods for improved power transmission performance |
US20070004603A1 (en) * | 2005-06-30 | 2007-01-04 | Iyer Ramnath N | Methods for improved power transmission performance and compositions therefor |
EP1974000B1 (en) * | 2005-12-15 | 2020-02-05 | The Lubrizol Corporation | Lubricant composition for a final drive axle |
JP2009530460A (en) * | 2006-03-22 | 2009-08-27 | シエル・インターナシヨネイル・リサーチ・マーチヤツピイ・ベー・ウイ | Functional fluid composition |
US20070270317A1 (en) * | 2006-05-19 | 2007-11-22 | Milner Jeffrey L | Power Transmission Fluids |
US9011556B2 (en) | 2007-03-09 | 2015-04-21 | Afton Chemical Corporation | Fuel composition containing a hydrocarbyl-substituted succinimide |
US20080289249A1 (en) * | 2007-05-22 | 2008-11-27 | Peter Wangqi Hou | Fuel additive to control deposit formation |
US20090005277A1 (en) * | 2007-06-29 | 2009-01-01 | Watts Raymond F | Lubricating Oils Having Improved Friction Stability |
US8623797B2 (en) * | 2007-06-29 | 2014-01-07 | Infineum International Limited | Boron-containing lubricating oils having improved friction stability |
US7878160B2 (en) | 2007-09-24 | 2011-02-01 | Afton Chemical Corporation | Surface passivation and to methods for the reduction of fuel thermal degradation deposits |
US8690968B2 (en) * | 2008-04-04 | 2014-04-08 | Afton Chemical Corporation | Succinimide lubricity additive for diesel fuel and a method for reducing wear scarring in an engine |
US8709108B2 (en) * | 2008-09-24 | 2014-04-29 | Afton Chemical Corporation | Fuel compositions |
WO2011026990A1 (en) | 2009-09-07 | 2011-03-10 | Shell Internationale Research Maatschappij B.V. | Lubricating compositions |
EP2169034B1 (en) | 2009-10-05 | 2017-05-17 | Afton Chemical Corporation | Fuel compositions |
DE202009013309U1 (en) | 2009-10-05 | 2010-03-04 | Afton Chemical Corp. | Fuel and fuel compositions |
SG183804A1 (en) | 2010-02-19 | 2012-10-30 | Infineum Int Ltd | Wet friction clutch-lubricant systems providing high dynamic coefficients of friction through the use of sodium detergents |
KR101681355B1 (en) | 2010-02-19 | 2016-11-30 | 인피늄 인터내셔날 리미티드 | Wet friction clutch-lubricant systems providing high dynamic coefficients of friction through the use of borated detergents |
US9018149B2 (en) | 2010-05-12 | 2015-04-28 | Exxonmobil Research And Engineering Company | Method for reducing one or more of deposits and friction of a lubricating oil |
US20120180382A1 (en) | 2011-01-19 | 2012-07-19 | Afton Chemical Corporation | Fuel Additives and Gasoline Containing the Additives |
US9523057B2 (en) | 2011-02-22 | 2016-12-20 | Afton Chemical Corporation | Fuel additives to maintain optimum injector performance |
US9068134B2 (en) | 2011-12-02 | 2015-06-30 | Exxonmobil Research And Engineering Company | Method for improving engine wear and corrosion resistance |
US9150812B2 (en) | 2012-03-22 | 2015-10-06 | Exxonmobil Research And Engineering Company | Antioxidant combination and synthetic base oils containing the same |
US9315756B2 (en) | 2012-04-06 | 2016-04-19 | Exxonmobil Research And Engineering Company | Bio-feeds based hybrid group V base stocks and method of production thereof |
US9422497B2 (en) | 2012-09-21 | 2016-08-23 | Exxonmobil Research And Engineering Company | Synthetic lubricant basestocks and methods of preparation thereof |
US20140113847A1 (en) | 2012-10-24 | 2014-04-24 | Exxonmobil Research And Engineering Company | High viscosity index lubricating oil base stock and viscosity modifier combinations, and lubricating oils derived therefrom |
US20140187457A1 (en) | 2013-01-03 | 2014-07-03 | Exxonmobil Research And Engineering Company | Lubricating compositions having improved shear stability |
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US11873461B1 (en) | 2022-09-22 | 2024-01-16 | Afton Chemical Corporation | Extreme pressure additives with improved copper corrosion |
US11884890B1 (en) | 2023-02-07 | 2024-01-30 | Afton Chemical Corporation | Gasoline additive composition for improved engine performance |
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Citations (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2052192A (en) * | 1935-10-23 | 1936-08-25 | Ici Ltd | Boric acid esters |
US2216618A (en) * | 1939-08-10 | 1940-10-01 | Katz Jacob | Surface active anionic boric acid ester compounds of amino alcohols |
US2234581A (en) * | 1937-09-30 | 1941-03-11 | Standard Oil Dev Co | Hydrocarbon composition containing organic boron compounds |
US2422278A (en) * | 1943-12-01 | 1947-06-17 | Standard Oil Dev Co | Lubricating oil composition |
US2611746A (en) * | 1947-06-10 | 1952-09-23 | Aluminum Co Of America | Lubricating composition |
US3000916A (en) * | 1958-06-03 | 1961-09-19 | Standard Oil Co | Composition of matter prepared by reacting polymerized linoleic acid with an amine and subsequently reacting the mixture with boric acid |
US3018291A (en) * | 1959-08-24 | 1962-01-23 | California Research Corp | Nu-dialkylaminoalkyl alkenyl succinimides |
Family Cites Families (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2459597A (en) * | 1945-05-16 | 1949-01-18 | Gulf Research Development Co | Di-alkylated mono-hydroxy phenol |
US3341633A (en) * | 1955-01-27 | 1967-09-12 | Lubrizol Corp | Reaction of o, o-dihydrocarbyl phosphorodithioic acids with epoxides |
US2956018A (en) * | 1955-07-01 | 1960-10-11 | Continental Oil Co | Metal containing organic compositions and method of preparing the same |
GB874877A (en) * | 1959-01-22 | 1961-08-10 | Exxon Research Engineering Co | Metal salts of organic dithiophosphates and lubricating compositions containing them |
FR1254094A (en) * | 1960-03-29 | 1961-02-17 | Lubrizol Corp | Metal-free additives for lubricants |
-
1961
- 1961-08-18 US US132305A patent/US3087936A/en not_active Expired - Lifetime
-
1962
- 1962-04-06 US US185520A patent/US3254025A/en not_active Expired - Lifetime
- 1962-08-15 GB GB39196/65A patent/GB1021183A/en not_active Expired
- 1962-08-15 GB GB31343/62A patent/GB1021182A/en not_active Expired
- 1962-08-17 DE DE19621644907 patent/DE1644907A1/en active Pending
- 1962-08-17 DE DEL42737A patent/DE1274776B/en active Pending
-
1964
- 1964-12-03 JP JP39067633A patent/JPS4936926B1/ja active Pending
-
1965
- 1965-01-08 FR FR1359A patent/FR87407E/en not_active Expired
-
1969
- 1969-02-15 JP JP44011432A patent/JPS4833242B1/ja active Pending
Patent Citations (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2052192A (en) * | 1935-10-23 | 1936-08-25 | Ici Ltd | Boric acid esters |
US2234581A (en) * | 1937-09-30 | 1941-03-11 | Standard Oil Dev Co | Hydrocarbon composition containing organic boron compounds |
US2216618A (en) * | 1939-08-10 | 1940-10-01 | Katz Jacob | Surface active anionic boric acid ester compounds of amino alcohols |
US2422278A (en) * | 1943-12-01 | 1947-06-17 | Standard Oil Dev Co | Lubricating oil composition |
US2611746A (en) * | 1947-06-10 | 1952-09-23 | Aluminum Co Of America | Lubricating composition |
US3000916A (en) * | 1958-06-03 | 1961-09-19 | Standard Oil Co | Composition of matter prepared by reacting polymerized linoleic acid with an amine and subsequently reacting the mixture with boric acid |
US3018291A (en) * | 1959-08-24 | 1962-01-23 | California Research Corp | Nu-dialkylaminoalkyl alkenyl succinimides |
US3018250A (en) * | 1959-08-24 | 1962-01-23 | California Research Corp | Lubricating oil compositions containing nu-dialkylaminoalkyl alkenyl succinimides |
Cited By (588)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3231587A (en) * | 1960-06-07 | 1966-01-25 | Lubrizol Corp | Process for the preparation of substituted succinic acid compounds |
US3188307A (en) * | 1962-04-13 | 1965-06-08 | Pure Oil Co | Alkenyl-n-sulfo-oxy-hydrocarbon-imides |
US3194812A (en) * | 1962-08-31 | 1965-07-13 | Lubrizol Corp | High molecular weight alkenyl-n-para amino-phenyl succinimide |
US3194813A (en) * | 1962-10-18 | 1965-07-13 | Lubrizol Corp | High molecular weight alkenyl-n-omega amino hexylsuccinimide |
US3194814A (en) * | 1962-10-18 | 1965-07-13 | Lubrizol Corp | High molecular weight alkenyl-n-allyl succinimide |
US3458530A (en) * | 1962-11-21 | 1969-07-29 | Exxon Research Engineering Co | Multi-purpose polyalkenyl succinic acid derivative |
US3243371A (en) * | 1962-12-10 | 1966-03-29 | Shell Oil Co | Lubricating composition |
US3189544A (en) * | 1962-12-19 | 1965-06-15 | Shell Oil Co | Non-ash-containing lubricating oil composition |
US3338832A (en) * | 1963-04-29 | 1967-08-29 | Lubrizol Corp | Lubricating oil containing reaction product of certain acylated nitrogen containing intermediates and a boron compound |
US3281428A (en) * | 1963-04-29 | 1966-10-25 | Lubrizol Corp | Reaction product of certain acylated nitrogen containing intermediates and a boron compound |
US3282955A (en) * | 1963-04-29 | 1966-11-01 | Lubrizol Corp | Reaction products of acylated nitrogen intermediates and a boron compound |
US3294684A (en) * | 1963-07-11 | 1966-12-27 | Standard Oil Co | Lubricant compositions containing detergency additives |
US3280034A (en) * | 1963-07-22 | 1966-10-18 | Monsanto Co | Alkenylsuccinimido alkyl-substituted imidazolidines and related materials |
US3322670A (en) * | 1963-08-26 | 1967-05-30 | Standard Oil Co | Detergent-dispersant lubricant additive having anti-rust and anti-wear properties |
US3455831A (en) * | 1963-09-27 | 1969-07-15 | Monsanto Co | Imines containing a polyalkenylsuccinic anhydride substituent |
DE1301535B (en) * | 1963-10-14 | 1970-02-05 | Lubrizol Corp | Process for the production of oil-soluble, nitrogen-containing reaction products |
US3367943A (en) * | 1963-11-01 | 1968-02-06 | Exxon Research Engineering Co | Process for preparing oil soluble additives which comprises reacting a c2 to c5 alkylene oxide with (a) reaction product of an alkenylsuccinic anhydride and an aliphaticpolyamine (b) reaction product of alkenylsuccinic anhydride, a c1 to c30 aliphatic hydrocarbon carboxylic acid and an aliphatic polyamine |
US3163603A (en) * | 1963-12-11 | 1964-12-29 | Lubrizol Corp | Amide and imide derivatives of metal salts of substituted succinic acids |
US3306908A (en) * | 1963-12-26 | 1967-02-28 | Lubrizol Corp | Reaction products of high molecular weight hydrocarbon succinic compounds, amines and heavy metal compounds |
US3311558A (en) * | 1964-05-19 | 1967-03-28 | Rohm & Haas | N-alkylmorpholinone esters of alkenylsuccinic anhydrides |
US3446808A (en) * | 1964-05-25 | 1969-05-27 | Universal Oil Prod Co | Borates of n-hydroxyalkyl-nitrogen-heterocyclic saturated compounds |
US3281357A (en) * | 1964-12-02 | 1966-10-25 | Lubrizol Corp | Process for preparing nitrogen and aluminum containing compositions |
US3449362A (en) * | 1965-03-08 | 1969-06-10 | Standard Oil Co | Alkenyl hydrocarbon substituted succinimides of polyamino ureas and their boron-containing derivatives |
US3491025A (en) * | 1965-03-08 | 1970-01-20 | Standard Oil Co | Mineral oil solutions of alkenyl substituted bis-succinimide of polyalkylene polyamino diamide from polyalkylene amine-urea condensation product |
US3385791A (en) * | 1965-03-22 | 1968-05-28 | Standard Oil Co | Lubricant oil composition |
US3340190A (en) * | 1965-06-01 | 1967-09-05 | Standard Oil Co | Railway diesel oil |
US3284410A (en) * | 1965-06-22 | 1966-11-08 | Lubrizol Corp | Substituted succinic acid-boron-alkylene amine-cyanamido derived additive and lubricating oil containing same |
US3284409A (en) * | 1965-06-22 | 1966-11-08 | Lubrizol Corp | Substituted succinic acid-boron-alkylene amine phosphatide derived additive and lubricating oil containing same |
US3344069A (en) * | 1965-07-01 | 1967-09-26 | Lubrizol Corp | Lubricant additive and lubricant containing same |
US3338834A (en) * | 1965-11-19 | 1967-08-29 | Chevron Res | Process for preparing nitrogen and boron-containing lubricating oil additives |
US3442808A (en) * | 1966-11-01 | 1969-05-06 | Standard Oil Co | Lubricating oil additives |
US3718663A (en) * | 1967-11-24 | 1973-02-27 | Standard Oil Co | Preparation of oil-soluble boron derivatives of an alkylene polyamine-urea or thiourea-succinic anhydride addition product |
US3903151A (en) * | 1971-07-14 | 1975-09-02 | Chevron Res | Reaction products of alkali metal meborate and hydrocarbon substituted succinimide |
US3892671A (en) * | 1972-08-25 | 1975-07-01 | Exxon Research Engineering Co | Lubricant containing dispersant-pour depressant polymer |
JPS4990704A (en) * | 1972-12-29 | 1974-08-29 | ||
US3950341A (en) * | 1973-04-12 | 1976-04-13 | Toa Nenryo Kogyo Kabushiki Kaisha | Reaction product of a polyalkenyl succinic acid or its anhydride, a hindered alcohol and an amine |
US3991056A (en) * | 1973-04-12 | 1976-11-09 | Toa Nenryo Kogyo Kabushiki Kaisha | Ashless detergent dispersant |
US4059536A (en) * | 1974-03-29 | 1977-11-22 | Institut Francais Du Petrole | Improved process for preparing superbasic detergent additives |
US4080303A (en) * | 1974-07-22 | 1978-03-21 | The Lubrizol Corporation | Lubricant compositions containing boron dispersant, VI improver, and aromatic carboxylic acid esters |
US4097389A (en) * | 1974-08-05 | 1978-06-27 | Mobil Oil Corporation | Novel amino alcohol reaction products and compositions containing the same |
US4025445A (en) * | 1975-12-15 | 1977-05-24 | Texaco Inc. | Boron amide lubricating oil additive |
US4092127A (en) * | 1976-12-20 | 1978-05-30 | Exxon Research & Engineering Co. | Anti-dieseling additive for spark ignition engines |
US4184851A (en) * | 1977-07-25 | 1980-01-22 | Exxon Research & Engineering Co. | Borated derivatives of hydrocarbon substituted succinamic acids and/or acid salts thereof are flow improvers for middle distillate fuel oils (PT-364) |
US4666620A (en) * | 1978-09-27 | 1987-05-19 | The Lubrizol Corporation | Carboxylic solubilizer/surfactant combinations and aqueous compositions containing same |
US4368133A (en) * | 1979-04-02 | 1983-01-11 | The Lubrizol Corporation | Aqueous systems containing nitrogen-containing, phosphorous-free carboxylic solubilizer/surfactant additives |
US4414125A (en) * | 1979-12-01 | 1983-11-08 | Chemische Werke Huels Aktiengesellschaft | Alkali metal or amine salts of a mixture of 2- and 3-alkyladipic acids as corrosion inhibitors |
US4295983A (en) * | 1980-06-12 | 1981-10-20 | Ethyl Corporation | Lubricating oil composition containing boronated N-hydroxymethyl succinimide friction reducers |
US4338205A (en) * | 1980-08-25 | 1982-07-06 | Exxon Research & Engineering Co. | Lubricating oil with improved diesel dispersancy |
US4447348A (en) * | 1981-02-25 | 1984-05-08 | The Lubrizol Corporation | Carboxylic solubilizer/surfactant combinations and aqueous compositions containing same |
US4448703A (en) * | 1981-02-25 | 1984-05-15 | The Lubrizol Corporation | Carboxylic solubilizer/surfactant combinations and aqueous compositions containing same |
EP0061346A2 (en) * | 1981-03-23 | 1982-09-29 | Edwin Cooper Inc. | Dispersant composition for lubricating oil, additive packages and lubricating oil compositions comprising the dispersant ingredients of said composition, a method of imparting dispersancy to a lubricating oil, and ingredients intended for use in a dispersant mixture |
EP0061346A3 (en) * | 1981-03-23 | 1983-07-20 | Edwin Cooper Inc. | Dispersant composition for lubricating oil, additive packages and lubricating oil compositions comprising the dispersant ingredients of said composition, a method of imparting dispersancy to a lubricating oil, and ingredients intended for use in a dispersant mixture |
US4596663A (en) * | 1982-08-09 | 1986-06-24 | The Lubrizol Corporation | Carboxylic acylating agents substituted with olefin polymers of high molecular weight mono-olefins, derivatives thereof, and fuels and lubricants containing same |
US4486573A (en) * | 1982-08-09 | 1984-12-04 | The Lubrizol Corporation | Carboxylic acylating agents substituted with olefin polymers of high molecular weight mono-olefins, derivatives thereof, and fuels and lubricants containing same |
US4489194A (en) * | 1982-08-09 | 1984-12-18 | The Lubrizol Corporation | Carboxylic acylating agents substituted with olefin polymers of high/low molecular weight mono-olefins, derivatives thereof, and fuels and lubricants containing same |
US4623684A (en) | 1982-08-09 | 1986-11-18 | The Lubrizol Corporation | Hydrocarbyl substituted carboxylic acylating agent derivative containing combinations, and fuels containing same |
US4559155A (en) * | 1982-08-09 | 1985-12-17 | The Lubrizol Corporation | Hydrocarbyl substituted carboxylic acylating agent derivative containing combinations, and fuels containing same |
US4613342A (en) * | 1982-08-09 | 1986-09-23 | The Lubrizol Corporation | Hydrocarbyl substituted carboxylic acylating agent derivative containing combinations, and fuels containing same |
US4564460A (en) * | 1982-08-09 | 1986-01-14 | The Lubrizol Corporation | Hydrocarbyl-substituted carboxylic acylating agent derivative containing combinations, and fuels containing same |
US4575526A (en) * | 1982-08-09 | 1986-03-11 | The Lubrizol Corporation | Hydrocarbyl substituted carboxylic acylaging agent derivative containing combinations, and fuels containing same |
US4471091A (en) * | 1982-08-09 | 1984-09-11 | The Lubrizol Corporation | Combinations of carboxylic acylating agents substituted with olefin polymers of high and low molecular weight mono-olefins, derivatives thereof, and fuels and lubricants containing same |
US4637886A (en) * | 1982-12-27 | 1987-01-20 | Exxon Research & Engineering Co. | Macrocyclic polyamine and polycyclic polyamine multifunctional lubricating oil additives |
WO1985003504A3 (en) * | 1984-02-09 | 1985-10-24 | Lubrizol Corp | Process for making substituted carboxylic acids and derivatives thereof |
JPH0696610B2 (en) * | 1984-02-09 | 1994-11-30 | ザ ル−ブリゾル コ−ポレイシヨン | Process for producing substituted carboxylic acid and derivative thereof |
AU574156B2 (en) * | 1984-02-09 | 1988-06-30 | Lubrizol Corporation, The | Process for producing carboxylic acids |
WO1985003504A2 (en) * | 1984-02-09 | 1985-08-15 | The Lubrizol Corporation | Process for making substituted carboxylic acids and derivatives thereof |
EP0167295A2 (en) * | 1984-06-05 | 1986-01-08 | Exxon Research And Engineering Company | Improved lubricating compositions |
EP0167295A3 (en) * | 1984-06-05 | 1987-01-28 | Exxon Research And Engineering Company | Improved lubricating compositions |
US4801390A (en) * | 1984-06-05 | 1989-01-31 | Exxon Research & Engineering Co. | Lubricating compositions |
US4749505A (en) * | 1985-07-08 | 1988-06-07 | Exxon Chemical Patents Inc. | Olefin polymer viscosity index improver additive useful in oil compositions |
US6051537A (en) * | 1985-07-11 | 2000-04-18 | Exxon Chemical Patents Inc | Dispersant additive mixtures for oleaginous compositions |
US6127321A (en) * | 1985-07-11 | 2000-10-03 | Exxon Chemical Patents Inc | Oil soluble dispersant additives useful in oleaginous compositions |
US6355074B1 (en) | 1985-07-11 | 2002-03-12 | Exxon Chemical Patents Inc | Oil soluble dispersant additives useful in oleaginous compositions |
US4756820A (en) * | 1985-09-06 | 1988-07-12 | Betz Laboratories, Inc. | Method for retarding corrosion and coke formation and deposition during pyrolytic hydrocarbon processing |
GB2183243B (en) * | 1985-10-09 | 1990-01-24 | Nippon Oil Co Ltd | Process for preparing oil-soluble nitrogen-containing compounds |
WO1987003003A1 (en) | 1985-11-08 | 1987-05-21 | The Lubrizol Corporation | Fuel compositions |
US5354484A (en) * | 1986-06-13 | 1994-10-11 | The Lubrizol Corporation | Phosphorus-containing lubricant and functional fluid compositions |
JPH01502987A (en) * | 1986-06-13 | 1989-10-12 | ザ ルブリゾル コーポレーション | Phosphorus-containing lubricants and functional fluid compositions |
JP2656522B2 (en) * | 1986-06-13 | 1997-09-24 | ザ ルブリゾル コーポレーション | Phosphorus-containing lubricants and functional fluid compositions |
US4770803A (en) * | 1986-07-03 | 1988-09-13 | The Lubrizol Corporation | Aqueous compositions containing carboxylic salts |
USRE36479E (en) * | 1986-07-03 | 2000-01-04 | The Lubrizol Corporation | Aqueous compositions containing nitrogen-containing salts |
US4755311A (en) * | 1986-08-14 | 1988-07-05 | The Lubrizol Corporation | Phosphorus-, sulfur- and boron-containing compositions, and lubricant and functional fluid compositions containing same |
US4963275A (en) * | 1986-10-07 | 1990-10-16 | Exxon Chemical Patents Inc. | Dispersant additives derived from lactone modified amido-amine adducts |
US5032320A (en) * | 1986-10-07 | 1991-07-16 | Exxon Chemical Patents Inc. | Lactone modified mono- or dicarboxylic acid based adduct dispersant compositions |
US4866140A (en) * | 1986-10-07 | 1989-09-12 | Exxon Chemical Patents Inc. | Lactone modified adducts or reactants and oleaginous compositions containing same |
US4954277A (en) * | 1986-10-07 | 1990-09-04 | Exxon Chemical Patents Inc. | Lactone modified, esterified or aminated additives useful in oleaginous compositions and compositions containing same |
US4954276A (en) * | 1986-10-07 | 1990-09-04 | Exxon Chemical Patents Inc. | Lactone modified adducts or reactants and oleaginous compositions containing same |
US4906394A (en) * | 1986-10-07 | 1990-03-06 | Exxon Chemical Patents Inc. | Lactone modified mono-or dicarboxylic acid based adduct dispersant compositions |
US4866139A (en) * | 1986-10-07 | 1989-09-12 | Exxon Chemical Patents Inc. | Lactone modified, esterified dispersant additives useful in oleaginous compositions |
US4866141A (en) * | 1986-10-07 | 1989-09-12 | Exxon Chemical Patents Inc. | Lactone modified, esterfied or aminated additives useful in oleaginous compositions and compositions containing same |
US5788722A (en) * | 1986-10-16 | 1998-08-04 | Exxon Chemical Patents Inc | High functionality low molecular weight oil soluble dispersant additives useful in oleaginous compositions |
US5756428A (en) * | 1986-10-16 | 1998-05-26 | Exxon Chemical Patents Inc. | High functionality low molecular weight oil soluble dispersant additives useful in oleaginous composition |
US4925983A (en) * | 1986-11-12 | 1990-05-15 | The Lubrizol Corporation | Boronated compounds |
US5583099A (en) * | 1986-11-12 | 1996-12-10 | The Lubrizol Corporation | Boronated compounds |
US5110488A (en) * | 1986-11-24 | 1992-05-05 | The Lubrizol Corporation | Lubricating compositions containing reduced levels of phosphorus |
US5451333A (en) * | 1987-05-26 | 1995-09-19 | Exxon Chemical Patents Inc. | Haze resistant dispersant-detergent compositions |
US5312554A (en) * | 1987-05-26 | 1994-05-17 | Exxon Chemical Patents Inc. | Process for preparing stable oleaginous compositions |
US4820432A (en) * | 1987-07-24 | 1989-04-11 | Exxon Chemical Patents Inc. | Lactone-modified, Mannich base dispersant additives useful in oleaginous compositions |
US4971711A (en) * | 1987-07-24 | 1990-11-20 | Exxon Chemical Patents, Inc. | Lactone-modified, mannich base dispersant additives useful in oleaginous compositions |
US4863624A (en) * | 1987-09-09 | 1989-09-05 | Exxon Chemical Patents Inc. | Dispersant additives mixtures for oleaginous compositions |
US4855074A (en) * | 1988-03-14 | 1989-08-08 | Ethyl Petroleum Additives, Inc. | Homogeneous additive concentrates and their formation |
US5389273A (en) * | 1988-03-14 | 1995-02-14 | Ethyl Petroleum Additives, Inc. | Modified succinimide or succinamide dispersants and their production |
US5439606A (en) * | 1988-03-14 | 1995-08-08 | Ethyl Petroleum Additives, Inc. | Modified succinimide or succinamide dispersants and their production |
US5198133A (en) * | 1988-03-14 | 1993-03-30 | Ethyl Petroleum Additives, Inc. | Modified succinimide or sucinamide dispersants and their production |
US4943382A (en) * | 1988-04-06 | 1990-07-24 | Exxon Chemical Patents Inc. | Lactone modified dispersant additives useful in oleaginous compositions |
US5041622A (en) * | 1988-04-22 | 1991-08-20 | The Lubrizol Corporation | Three-step process for making substituted carboxylic acids and derivatives thereof |
EP0351964A1 (en) | 1988-06-24 | 1990-01-24 | Exxon Chemical Patents Inc. | Synergistic combination of additives useful in power transmitting compositions |
US5334329A (en) * | 1988-10-07 | 1994-08-02 | The Lubrizol Corporation | Lubricant and functional fluid compositions exhibiting improved demulsibility |
EP0399764A1 (en) | 1989-05-22 | 1990-11-28 | Ethyl Petroleum Additives Limited | Lubricant compositions |
US5225093A (en) * | 1990-02-16 | 1993-07-06 | Ethyl Petroleum Additives, Inc. | Gear oil additive compositions and gear oils containing the same |
US5646098A (en) * | 1990-07-23 | 1997-07-08 | Exxon Chemical Patents Inc | Carbonyl containing compounds and their derivatives as multi-functional fuel and lube additives |
EP0611818A1 (en) | 1990-07-31 | 1994-08-24 | Exxon Chemical Patents Inc. | Low pressure derived mixed phosphorous- and sulfur-containing reaction products useful in power transmitting compositions and process for preparing the same |
US5562864A (en) * | 1991-04-19 | 1996-10-08 | The Lubrizol Corporation | Lubricating compositions and concentrates |
US5490945A (en) * | 1991-04-19 | 1996-02-13 | The Lubrizol Corporation | Lubricating compositions and concentrates |
US5614480A (en) * | 1991-04-19 | 1997-03-25 | The Lubrizol Corporation | Lubricating compositions and concentrates |
US5652201A (en) * | 1991-05-29 | 1997-07-29 | Ethyl Petroleum Additives Inc. | Lubricating oil compositions and concentrates and the use thereof |
US5328619A (en) * | 1991-06-21 | 1994-07-12 | Ethyl Petroleum Additives, Inc. | Oil additive concentrates and lubricants of enhanced performance capabilities |
US5221491A (en) * | 1991-08-09 | 1993-06-22 | Exxon Chemical Patents Inc. | Two-cycle oil additive |
EP0558835A1 (en) | 1992-01-30 | 1993-09-08 | Albemarle Corporation | Biodegradable lubricants and functional fluids |
US5304315A (en) * | 1992-04-15 | 1994-04-19 | Exxon Chemical Patents Inc. | Prevention of gel formation in two-cycle oils |
US5330667A (en) * | 1992-04-15 | 1994-07-19 | Exxon Chemical Patents Inc. | Two-cycle oil additive |
US5370807A (en) * | 1992-05-15 | 1994-12-06 | Ministero Dell'universita' E Della Ricerca Scientifica E Technologica | Boron-containing additive for lubricating oils, and process for preparing said additive |
US5308521A (en) * | 1992-07-08 | 1994-05-03 | The Lubrizol Corporation | Lubricant with improved anti-corrosion properties |
US5646332A (en) * | 1992-12-17 | 1997-07-08 | Exxon Chemical Patents Inc. | Batch Koch carbonylation process |
US5703256A (en) * | 1992-12-17 | 1997-12-30 | Exxon Chemical Patents Inc. | Functionalization of polymers based on Koch chemistry and derivatives thereof |
US5643859A (en) * | 1992-12-17 | 1997-07-01 | Exxon Chemical Patents Inc. | Derivatives of polyamines with one primary amine and secondary of tertiary amines |
US5629434A (en) * | 1992-12-17 | 1997-05-13 | Exxon Chemical Patents Inc | Functionalization of polymers based on Koch chemistry and derivatives thereof |
US5650536A (en) * | 1992-12-17 | 1997-07-22 | Exxon Chemical Patents Inc. | Continuous process for production of functionalized olefins |
WO1994013762A1 (en) * | 1992-12-17 | 1994-06-23 | Exxon Chemical Patents Inc. | Improved low sediment process for forming borated dispersant |
US6030930A (en) * | 1992-12-17 | 2000-02-29 | Exxon Chemical Patents Inc | Polymers derived from ethylene and 1-butene for use in the preparation of lubricant disperant additives |
US5554310A (en) * | 1992-12-17 | 1996-09-10 | Exxon Chemical Patents Inc. | Trisubstituted unsaturated polymers |
US5663130A (en) * | 1992-12-17 | 1997-09-02 | Exxon Chemical Patents Inc | Polymers derived from ethylene and 1-butene for use in the preparation of lubricant dispersant additives |
US5717039A (en) * | 1992-12-17 | 1998-02-10 | Exxon Chemical Patents Inc. | Functionalization of polymers based on Koch chemistry and derivatives thereof |
US5430105A (en) * | 1992-12-17 | 1995-07-04 | Exxon Chemical Patents Inc. | Low sediment process for forming borated dispersant |
US5696064A (en) * | 1992-12-17 | 1997-12-09 | Exxon Chemical Patents Inc. | Functionalization of polymers based on Koch chemistry and derivatives thereof |
US5698722A (en) * | 1992-12-17 | 1997-12-16 | Exxon Chemical Patents Inc. | Functionalization of polymers based on Koch chemistry and derivatives thereof |
US5498809A (en) * | 1992-12-17 | 1996-03-12 | Exxon Chemical Patents Inc. | Polymers derived from ethylene and 1-butene for use in the preparation of lubricant dispersant additives |
US5562867A (en) * | 1993-12-30 | 1996-10-08 | Exxon Chemical Patents Inc | Biodegradable two-cycle oil composition |
EP0683220A2 (en) | 1994-05-18 | 1995-11-22 | Ethyl Corporation | Lubricant additive compositions |
US6362136B1 (en) | 1994-05-23 | 2002-03-26 | The Lubrizol Corporation | Compositions for extending seal life, and lubricants and functional fluids containing the same |
US5767046A (en) * | 1994-06-17 | 1998-06-16 | Exxon Chemical Company | Functionalized additives useful in two-cycle engines |
US6489271B1 (en) | 1994-08-03 | 2002-12-03 | The Lubrizol Corporation | Combination of a sulfur compound and specific phosphorus compounds and their use in lubricating compositions, concentrates and greases |
EP0695798A2 (en) | 1994-08-03 | 1996-02-07 | The Lubrizol Corporation | Lubricating compositions, concentrates, and greases containing the combination of an organic polysulfide and an overbased composition or a phosphorus or boron compound |
US6306802B1 (en) | 1994-09-30 | 2001-10-23 | Exxon Chemical Patents Inc. | Mixed antioxidant composition |
EP0713908A1 (en) | 1994-11-22 | 1996-05-29 | Ethyl Corporation | Power transmission fluids |
US5658862A (en) * | 1994-12-20 | 1997-08-19 | Exxon Research And Engineering Company | Engine oil with improved fuel economy properties (law372). |
US5652202A (en) * | 1995-08-15 | 1997-07-29 | Exxon Chemical Patents Inc. | Lubricating oil compositions |
US5558802A (en) * | 1995-09-14 | 1996-09-24 | Exxon Chemical Patents Inc | Multigrade crankcase lubricants with low temperature pumpability and low volatility |
BE1011443A4 (en) * | 1996-04-19 | 1999-09-07 | Ethyl Petroleum Additives Ltd | DISPERSANT oil soluble FOR LUBRICATING OIL. |
FR2747687A1 (en) * | 1996-04-19 | 1997-10-24 | Ethyl Petroleum Additives Ltd | OLEOSOLUBLE DIPERSANT FOR LUBRICATING OIL |
US6476096B1 (en) * | 1998-02-02 | 2002-11-05 | Xaar Technology Limited | Ink jet printer ink |
US6008165A (en) * | 1998-07-31 | 1999-12-28 | The Lubrizol Corporation | Alcohol borate esters and borated dispersants to improve bearing corrosion in engine oils |
US6010986A (en) * | 1998-07-31 | 2000-01-04 | The Lubrizol Corporation | Alcohol borate esters to improve bearing corrosion in engine oils |
US6231659B1 (en) | 1999-06-24 | 2001-05-15 | Albemarle Corporation | Sizing agents and starting materials for their preparation |
US6225437B1 (en) | 1999-06-24 | 2001-05-01 | Albemarle Corporation | Sizing agents of enhanced performance capabilities |
US6423670B2 (en) | 2000-03-20 | 2002-07-23 | Infineum International Ltd. | Lubricating oil compositions |
US20030173251A1 (en) * | 2000-12-22 | 2003-09-18 | Antonio Gutierrez | Hydroxy aromatic mannich base condensation products and the use thereof as soot dispersants in lubricating oil compositions |
US6855674B2 (en) | 2000-12-22 | 2005-02-15 | Infineum International Ltd. | Hydroxy aromatic Mannich base condensation products and the use thereof as soot dispersants in lubricating oil compositions |
US6949688B2 (en) | 2001-05-17 | 2005-09-27 | Exxonmobil Chemical Patents Inc. | Low Noack volatility poly α-olefins |
US20020193650A1 (en) * | 2001-05-17 | 2002-12-19 | Goze Maria Caridad B. | Low noack volatility poly alpha-olefins |
US20050045527A1 (en) * | 2001-05-17 | 2005-03-03 | Goze Maria Caridad B. | Low noack volatility poly alpha-olefins |
US6824671B2 (en) | 2001-05-17 | 2004-11-30 | Exxonmobil Chemical Patents Inc. | Low noack volatility poly α-olefins |
SG126712A1 (en) * | 2001-12-06 | 2006-11-29 | Infineum Int Ltd | Dispersants and lubricating oil compositions containing same |
US6734148B2 (en) | 2001-12-06 | 2004-05-11 | Infineum International Ltd. | Dispersants and lubricating oil compositions containing same |
US6743757B2 (en) | 2001-12-06 | 2004-06-01 | Infineum International Ltd. | Dispersants and lubricating oil compositions containing same |
US6627584B2 (en) | 2002-01-28 | 2003-09-30 | Ethyl Corporation | Automatic transmission fluid additive comprising reaction product of hydrocarbyl acrylates and dihydrocarbyldithiophosphoric acids |
US6573223B1 (en) | 2002-03-04 | 2003-06-03 | The Lubrizol Corporation | Lubricating compositions with good thermal stability and demulsibility properties |
US7182795B2 (en) | 2002-03-13 | 2007-02-27 | Atton Chemical Intangibles Llc | Fuel lubricity additives derived from hydrocarbyl succinic anhydrides and hydroxy amines, and middle distillate fuels containing same |
US20030172584A1 (en) * | 2002-03-13 | 2003-09-18 | Henly Timothy J. | Fuel lubricity additives derived from hydrocarbyl succinic anhydrides and hydroxy amines, and middle distillate fuels containing same |
WO2003095595A1 (en) | 2002-05-09 | 2003-11-20 | The Lubrizol Corporation | Continuously variable transmission fluids comprising a combination of calcium- and magnesium-overbased detergents |
US20040033908A1 (en) * | 2002-08-16 | 2004-02-19 | Deckman Douglas E. | Functional fluid lubricant using low Noack volatility base stock fluids |
US6869917B2 (en) | 2002-08-16 | 2005-03-22 | Exxonmobil Chemical Patents Inc. | Functional fluid lubricant using low Noack volatility base stock fluids |
EP2460870A1 (en) | 2002-10-04 | 2012-06-06 | R.T. Vanderbilt Company, Inc. | Synergistic organoborate compositions and lubricating compositions containing same |
EP2436753A1 (en) | 2002-10-04 | 2012-04-04 | R.T. Vanderbilt Company Inc. | Synergistic organoborate compositions and lubricating compositions containing same |
EP2366762A1 (en) | 2002-10-04 | 2011-09-21 | R.T. Vanderbilt Company Inc. | Synergistic organoborate compositions and lubricating compositions containing same |
EP2302023A2 (en) | 2002-10-04 | 2011-03-30 | R.T. Vanderbilt Company, Inc. | Synergistic organoborate compositions and lubricating compositions containing same |
US20040147410A1 (en) * | 2003-01-15 | 2004-07-29 | Milner Jeffrey L | Extended drain, thermally stable, gear oil formulations |
US7888299B2 (en) | 2003-01-15 | 2011-02-15 | Afton Chemical Japan Corp. | Extended drain, thermally stable, gear oil formulations |
US20090280185A1 (en) * | 2003-06-17 | 2009-11-12 | Phibrowood, Llc | Particulate wood preservative and method for producing the same |
US8871277B2 (en) | 2003-06-17 | 2014-10-28 | Osmose, Inc. | Particulate wood preservative and method for producing the same |
US8409627B2 (en) | 2003-06-17 | 2013-04-02 | Osmose, Inc. | Particulate wood preservative and method for producing the same |
US6933351B2 (en) | 2003-06-20 | 2005-08-23 | Infineum International Limited | Process for forming polyalkenyl acylating agents |
US7339007B2 (en) | 2003-06-20 | 2008-03-04 | Infineum International Limited | Low sediment process for thermally reacting highly reactive polymers and enophiles |
US20040260027A1 (en) * | 2003-06-20 | 2004-12-23 | Michaud Vincent Jean Marie | Process for forming polyalkenyl acylating agents |
US20040260032A1 (en) * | 2003-06-20 | 2004-12-23 | Irving Matthew David | Low sediment process for thermally reacting highly reactive polymers and enophiles |
US20050041395A1 (en) * | 2003-08-21 | 2005-02-24 | The Lubrizol Corporation | Multifunctional dispersants |
US20050065043A1 (en) * | 2003-09-23 | 2005-03-24 | Henly Timothy J. | Power transmission fluids having extended durability |
EP2230292A1 (en) | 2003-11-10 | 2010-09-22 | Afton Chemical Corporation | Methods of lubricating transmissions |
US20050101494A1 (en) * | 2003-11-10 | 2005-05-12 | Iyer Ramnath N. | Lubricant compositions for power transmitting fluids |
US20080009426A1 (en) * | 2003-11-10 | 2008-01-10 | Iyer Ramnath N | Lubricant Compositions and Methods Comprising Dispersant and Detergent |
US20100279901A1 (en) * | 2003-11-10 | 2010-11-04 | Iyer Ramnath N | Methods for providing steel-on-steel friction and/or steel-on-paper friction with lubricant compositions for power transmitting fluids |
US9267093B2 (en) | 2003-11-10 | 2016-02-23 | Afton Chemical Corporation | Methods for providing steel-on-steel friction and/or steel-on-paper friction with lubricant compositions for power transmitting fluids |
US20050101497A1 (en) * | 2003-11-12 | 2005-05-12 | Saathoff Lee D. | Compositions and methods for improved friction durability in power transmission fluids |
US20080090744A1 (en) * | 2003-11-12 | 2008-04-17 | Saathoff Lee D | Compositions and Methods for Improved Friction Durability in Power Transmission Fluids |
US7947636B2 (en) | 2004-02-27 | 2011-05-24 | Afton Chemical Corporation | Power transmission fluids |
US20050192185A1 (en) * | 2004-02-27 | 2005-09-01 | Saathoff Lee D. | Power transmission fluids |
US20050202979A1 (en) * | 2004-03-10 | 2005-09-15 | Ethyl Petroleum Additives, Inc. | Power transmission fluids with enhanced extreme pressure characteristics |
US20050255251A1 (en) * | 2004-05-17 | 2005-11-17 | Hodge Robert L | Composition, method of making, and treatment of wood with an injectable wood preservative slurry having biocidal particles |
US20090123505A1 (en) * | 2004-05-17 | 2009-05-14 | Phibrowood, Llc | Particulate Wood Preservative and Method for Producing Same |
US8722198B2 (en) | 2004-05-17 | 2014-05-13 | Osmose, Inc. | Method of preserving wood by injecting particulate wood preservative slurry |
US8158208B2 (en) | 2004-05-17 | 2012-04-17 | Osmose, Inc. | Method of preserving wood by injecting particulate wood preservative slurry |
US9314030B2 (en) | 2004-05-17 | 2016-04-19 | Koppers Performance Chemicals Inc. | Particulate wood preservative and method for producing same |
US20090223408A1 (en) * | 2004-05-17 | 2009-09-10 | Phibrowood, Llc | Use of Sub-Micron Copper Salt Particles in Wood Preservation |
US20060003905A1 (en) * | 2004-07-02 | 2006-01-05 | Devlin Cathy C | Additives and lubricant formulations for improved corrosion protection |
US20060025314A1 (en) * | 2004-07-28 | 2006-02-02 | Afton Chemical Corporation | Power transmission fluids with enhanced extreme pressure and antiwear characteristics |
EP1624043A2 (en) | 2004-07-28 | 2006-02-08 | Afton Chemical Corporation | Power transmission fluids with enhanced extreme pressure and antiwear characteristics |
US20090143478A1 (en) * | 2004-10-08 | 2009-06-04 | Phibrowood, Llc | Milled Submicron Organic Biocides With Narrow Particle Size Distribution, and Uses Thereof |
US20080213608A1 (en) * | 2004-10-08 | 2008-09-04 | Richardson Hugh W | Milled Submicron Chlorothalonil With Narrow Particle Size Distribution, and Uses Thereof |
US20060075923A1 (en) * | 2004-10-12 | 2006-04-13 | Richardson H W | Method of manufacture and treatment of wood with injectable particulate iron oxide |
US9775350B2 (en) | 2004-10-14 | 2017-10-03 | Koppers Performance Chemicals Inc. | Micronized wood preservative formulations in organic carriers |
US20060122073A1 (en) * | 2004-12-08 | 2006-06-08 | Chip Hewette | Oxidation stable gear oil compositions |
EP1669436A1 (en) | 2004-12-08 | 2006-06-14 | Afton Chemical Corporation | Oxidation stable gear oil compositions |
US9481841B2 (en) * | 2004-12-09 | 2016-11-01 | The Lubrizol Corporation | Process of preparation of an additive and its use |
WO2006063161A2 (en) * | 2004-12-09 | 2006-06-15 | The Lubrizol Corporation | Process of preparation of an additive and its use |
WO2006063161A3 (en) * | 2004-12-09 | 2007-02-22 | Lubrizol Corp | Process of preparation of an additive and its use |
US20090149358A1 (en) * | 2004-12-09 | 2009-06-11 | Rhoads Gabriel B | Process of Preparation of an Additive and Its Use |
CN101072798B (en) * | 2004-12-09 | 2013-10-16 | 卢布里佐尔公司 | Process of preparation of an additive and its use |
EP2116590A1 (en) | 2005-02-18 | 2009-11-11 | Infineum International Limited | Soot dispersants and lubricating oil compositions containing same |
WO2006094011A2 (en) | 2005-03-01 | 2006-09-08 | R.T. Vanderbilt Company, Inc. | Molybdenum dialkyldithiocarbamate compositions and lubricating compositions containing the same |
US20060217273A1 (en) * | 2005-03-23 | 2006-09-28 | Nubar Ozbalik | Lubricating compositions |
US8557752B2 (en) | 2005-03-23 | 2013-10-15 | Afton Chemical Corporation | Lubricating compositions |
US20060223716A1 (en) * | 2005-04-04 | 2006-10-05 | Milner Jeffrey L | Tractor fluids |
US20060252660A1 (en) * | 2005-05-09 | 2006-11-09 | Akhilesh Duggal | Hydrolytically stable viscosity index improves |
EP1728848A1 (en) | 2005-06-01 | 2006-12-06 | Infineum International Limited | Use of unsaturated olefin polymers to improve the compatibility between nitrile rubber seals and lubricating oil compositions |
US20110036262A1 (en) * | 2005-07-11 | 2011-02-17 | Advanced Lubrication Technology, Inc. | Corrosion Prevention and Friction Reduction Coating and Low Temperature Process |
US20070021310A1 (en) * | 2005-07-11 | 2007-01-25 | Olliges William E | Corrosion Prevention and Friction Reduction Coating and Low Temperature Process |
WO2007008802A3 (en) * | 2005-07-11 | 2007-05-03 | Advanced Lubrication Technolog | Corrosion prevention and friction reduction coating and low temperature process |
US20090029888A1 (en) * | 2005-07-12 | 2009-01-29 | Ramanathan Ravichandran | Amine tungstates and lubricant compositions |
US20070042917A1 (en) * | 2005-07-12 | 2007-02-22 | Ramanathan Ravichandran | Amine Tungstates and Lubricant Compositions |
US7820602B2 (en) | 2005-07-12 | 2010-10-26 | King Industries, Inc. | Amine tungstates and lubricant compositions |
US8080500B2 (en) | 2005-07-12 | 2011-12-20 | King Industries, Inc. | Amine tungstates and lubricant compositions |
US20080194440A1 (en) * | 2005-07-12 | 2008-08-14 | Ramanathan Ravichandran | Amine tungstates and lubricant compositions |
US20070078066A1 (en) * | 2005-10-03 | 2007-04-05 | Milner Jeffrey L | Lubricant formulations containing extreme pressure agents |
US20070105728A1 (en) * | 2005-11-09 | 2007-05-10 | Phillips Ronald L | Lubricant composition |
US7928260B2 (en) | 2005-11-09 | 2011-04-19 | Afton Chemical Corporation | Salt of a sulfur-containing, phosphorus-containing compound, and methods thereof |
US8299003B2 (en) | 2005-11-09 | 2012-10-30 | Afton Chemical Corporation | Composition comprising a sulfur-containing, phosphorus-containing compound, and/or its salt, and uses thereof |
US20070142237A1 (en) * | 2005-11-09 | 2007-06-21 | Degonia David J | Lubricant composition |
US20070142659A1 (en) * | 2005-11-09 | 2007-06-21 | Degonia David J | Sulfur-containing, phosphorus-containing compound, its salt, and methods thereof |
US20070142660A1 (en) * | 2005-11-09 | 2007-06-21 | Degonia David J | Salt of a sulfur-containing, phosphorus-containing compound, and methods thereof |
US20080319216A1 (en) * | 2005-11-09 | 2008-12-25 | Degonia David J | Salt of a Sulfur-Containing, Phosphorus-Containing Compound, And Methods Thereof |
US20070111906A1 (en) * | 2005-11-12 | 2007-05-17 | Milner Jeffrey L | Relatively low viscosity transmission fluids |
US20070259016A1 (en) * | 2006-05-05 | 2007-11-08 | Hodge Robert L | Method of treating crops with submicron chlorothalonil |
US20080015127A1 (en) * | 2006-07-14 | 2008-01-17 | Loper John T | Boundary friction reducing lubricating composition |
US20080015124A1 (en) * | 2006-07-14 | 2008-01-17 | Devlin Mark T | Lubricant composition |
US7902133B2 (en) | 2006-07-14 | 2011-03-08 | Afton Chemical Corporation | Lubricant composition |
US20080015125A1 (en) * | 2006-07-14 | 2008-01-17 | Devlin Mark T | Lubricant compositions |
US7879775B2 (en) | 2006-07-14 | 2011-02-01 | Afton Chemical Corporation | Lubricant compositions |
EP3339404A1 (en) | 2006-07-18 | 2018-06-27 | Infineum International Limited | Lubricating oil compositions |
WO2008013698A1 (en) | 2006-07-21 | 2008-01-31 | Exxonmobil Research And Engineering Company | Method for lubricating heavy duty geared apparatus |
US7833953B2 (en) | 2006-08-28 | 2010-11-16 | Afton Chemical Corporation | Lubricant composition |
US20080051305A1 (en) * | 2006-08-28 | 2008-02-28 | Devlin Mark T | Lubricant composition |
US20080119377A1 (en) * | 2006-11-22 | 2008-05-22 | Devlin Mark T | Lubricant compositions |
US20080182768A1 (en) * | 2007-01-31 | 2008-07-31 | Devlin Cathy C | Lubricant composition for bio-diesel fuel engine applications |
DE102008005330A1 (en) | 2007-01-31 | 2008-08-07 | Afton Chemical Corp. | Lubricant composition for biodiesel fuel engine uses |
EP1959003A2 (en) | 2007-02-08 | 2008-08-20 | Infineum International Limited | Soot dispersants and lubricating oil compositions containing same |
EP2420553A1 (en) | 2007-05-04 | 2012-02-22 | Afton Chemical Corporation | Environmentally-Friendly Lubricant Compositions |
EP2017329A1 (en) | 2007-05-04 | 2009-01-21 | Afton Chemical Corporation | Environmentally-Friendly Lubricant Compositions |
US20080274921A1 (en) * | 2007-05-04 | 2008-11-06 | Ian Macpherson | Environmentally-Friendly Lubricant Compositions |
US20100152078A1 (en) * | 2007-05-04 | 2010-06-17 | Ian Macpherson | Environmentally-friendly lubricant compositions |
WO2008154334A1 (en) | 2007-06-08 | 2008-12-18 | Infineum International Limited | Additives and lubricating oil compositions containing same |
US20090011963A1 (en) * | 2007-07-06 | 2009-01-08 | Afton Chemical Corporation | Truck fleet fuel economy by the use of optimized engine oil, transmission fluid, and gear oil |
US20140066579A1 (en) * | 2007-07-18 | 2014-03-06 | Eni S.P.A. | Polyalkenyl succinimides and use thereof as dispersants in lubricating oils |
US20090031614A1 (en) * | 2007-08-01 | 2009-02-05 | Ian Macpherson | Environmentally-Friendly Fuel Compositions |
EP2025737A1 (en) | 2007-08-01 | 2009-02-18 | Afton Chemical Corporation | Environmentally-friendly fuel compositions |
US20090071067A1 (en) * | 2007-09-17 | 2009-03-19 | Ian Macpherson | Environmentally-Friendly Additives And Additive Compositions For Solid Fuels |
WO2009045979A1 (en) | 2007-10-03 | 2009-04-09 | The Lubrizol Corporation | Lubricants that decrease micropitting for industrial gears |
US20090156449A1 (en) * | 2007-12-12 | 2009-06-18 | Rowland Robert G | Alkylated 1,3-benzenediamine compounds and methods for producing same |
US8563489B2 (en) | 2007-12-12 | 2013-10-22 | Chemtura Corporation | Alkylated 1,3-benzenediamine compounds and methods for producing same |
EP2075315A1 (en) | 2007-12-12 | 2009-07-01 | Infineum International Limited | Additive Compositions with Michael adducts of N-substituted phenylenediamines |
US20090156441A1 (en) * | 2007-12-12 | 2009-06-18 | Rowland Robert G | Cycloalkyl phenylenediamines as deposit control agents for lubricants |
EP2075264A1 (en) | 2007-12-26 | 2009-07-01 | Infineum International Limited | Method of forming polyalkene substituted carboxylic acid compositions |
EP2083063A1 (en) | 2008-01-22 | 2009-07-29 | Infineum International Limited | Lubricating oil composition |
US20090192061A1 (en) * | 2008-01-24 | 2009-07-30 | Boegner Philip J | Olefin copolymer dispersant vi improver and lubricant compositions and uses thereof |
EP2083024A1 (en) | 2008-01-24 | 2009-07-29 | Afton Chemical Corporation | Olefin copolymer dispersant VI improver and lubricant compositions and uses thereof |
US8420583B2 (en) | 2008-01-24 | 2013-04-16 | Afton Chemical Corporation | Olefin copolymer dispersant VI improver and lubricant compositions and uses thereof |
EP2090642A1 (en) | 2008-02-08 | 2009-08-19 | Infineum International Limited | Engine lubrication |
DE102009012567A1 (en) | 2008-03-11 | 2009-10-01 | Afton Chemical Corp. | Clutch-only transmission fluid useful for lubrication comprises oil formulated with additive components having metal detergent, phosphorus-based wear preventative, phosphorylated and boronated dispersant, sulfurized extreme pressure agent |
DE102009001301A1 (en) | 2008-03-11 | 2009-09-24 | Volkswagen Ag | Method for lubricating a component only for the clutch of an automatic transmission, which requires lubrication |
US8703669B2 (en) | 2008-03-11 | 2014-04-22 | Afton Chemical Corporation | Ultra-low sulfur clutch-only transmission fluids |
US8546311B2 (en) | 2008-03-11 | 2013-10-01 | Volkswagen Aktiengesellsschaft | Method for lubricating a clutch-only automatic transmission component requiring lubrication |
US20090233822A1 (en) * | 2008-03-11 | 2009-09-17 | Afton Chemical Corporation | Ultra-low sulfur clutch-only transmission fluids |
WO2009119831A1 (en) | 2008-03-28 | 2009-10-01 | 富士フイルム株式会社 | Composition and method for forming coating film |
EP2163602A1 (en) | 2008-09-05 | 2010-03-17 | Infineum International Limited | A lubricating oil composition |
EP2161326A1 (en) | 2008-09-05 | 2010-03-10 | Infineum International Limited | Lubricating oil compositions |
EP2620207A2 (en) | 2008-10-31 | 2013-07-31 | Calera Corporation | Non-cementitious compositions comprising CO2 sequestering additives |
US9133581B2 (en) | 2008-10-31 | 2015-09-15 | Calera Corporation | Non-cementitious compositions comprising vaterite and methods thereof |
WO2010077630A1 (en) | 2008-12-09 | 2010-07-08 | The Lubrizol Corporation | Lubricating composition containing a compound derived from a hydroxy-carboxylic acid |
EP2206764A1 (en) | 2008-12-23 | 2010-07-14 | Infineum International Limited | Aniline compounds as ashless TBN sources and lubricating oil compositions containing same |
EP2233554A1 (en) | 2009-03-27 | 2010-09-29 | Infineum International Limited | Lubricating oil compositions |
EP2236590A1 (en) | 2009-04-01 | 2010-10-06 | Infineum International Limited | Lubricating oil composition |
EP2239314A1 (en) | 2009-04-06 | 2010-10-13 | Infineum International Limited | Lubricating oil composition |
WO2010115594A1 (en) | 2009-04-07 | 2010-10-14 | Infineum International Limited | Marine engine lubrication |
EP2365049A1 (en) | 2009-08-24 | 2011-09-14 | Infineum International Limited | Use of a lubricating additive |
EP2290043A1 (en) | 2009-08-24 | 2011-03-02 | Infineum International Limited | A lubricating oil composition comprising metal dialkyldithiophosphate and carbodiimide |
EP2290038A2 (en) | 2009-08-24 | 2011-03-02 | Infineum International Limited | A lubricating oil composition |
EP2290041A2 (en) | 2009-08-24 | 2011-03-02 | Infineum International Limited | A lubricating oil composition |
US8080699B2 (en) | 2009-08-28 | 2011-12-20 | Chemtura Corporation | Two-stage process and system for forming high viscosity polyalphaolefins |
US20110054126A1 (en) * | 2009-08-28 | 2011-03-03 | Chemtura Corporation | Two-stage process and system for forming high viscosity polyalphaolefins |
WO2011025636A1 (en) | 2009-08-28 | 2011-03-03 | Chemtura Corporation | Two-stage process and system for forming high viscosity polyalphaolefins |
WO2011034829A1 (en) | 2009-09-16 | 2011-03-24 | The Lubrizol Corporation | Lubricating composition containing an ester |
WO2011059583A1 (en) | 2009-10-29 | 2011-05-19 | Chemtura Corporation | Lubrication and lubricating oil compositions |
EP2319904A1 (en) | 2009-10-29 | 2011-05-11 | Infineum International Limited | Lubrication and lubricating oil compositions comprising phenylene diamines |
US8415284B2 (en) | 2009-11-05 | 2013-04-09 | Afton Chemical Corporation | Olefin copolymer VI improvers and lubricant compositions and uses thereof |
US20110105371A1 (en) * | 2009-11-05 | 2011-05-05 | Afton Chemical Corporation | Olefin copolymer vi improvers and lubricant compositions and uses thereof |
EP2325291A1 (en) | 2009-11-05 | 2011-05-25 | Afton Chemical Corporation | Olefin Copolymer VI improvers and lubricant compositions and uses thereof |
WO2011066145A1 (en) | 2009-11-30 | 2011-06-03 | The Lubrizol Corporation | Stabilized blends containing friction modifiers |
WO2011066144A1 (en) | 2009-11-30 | 2011-06-03 | The Lubrizol Corporation | Stabilized blends containing friction modifiers |
WO2011066142A1 (en) | 2009-11-30 | 2011-06-03 | The Lubrizol Corporation | Stabilized blends containing friction modifiers |
EP2390306A1 (en) | 2009-12-01 | 2011-11-30 | Infineum International Limited | A lubricating oil composition |
EP2363454A1 (en) | 2010-02-23 | 2011-09-07 | Infineum International Limited | A lubricating oil composition |
EP2366761A1 (en) | 2010-03-09 | 2011-09-21 | Infineum International Limited | Morpholine derivatives as ashless TBN sources and lubricating oil compositions containing same |
EP2371934A1 (en) | 2010-03-31 | 2011-10-05 | Infineum International Limited | Lubricating oil composition |
EP2371932A1 (en) | 2010-04-01 | 2011-10-05 | Infineum International Limited | A lubricating oil composition |
EP2374866A1 (en) | 2010-04-06 | 2011-10-12 | Infineum International Limited | A lubricating oil composition comprising alkoxylated phenol-formaldehyde condensate |
WO2011130142A1 (en) | 2010-04-15 | 2011-10-20 | The Lubrizol Corporation | Low-ash lubricating oils for diesel engines |
WO2011149810A1 (en) | 2010-05-24 | 2011-12-01 | The Lubrizol Corporation | Lubricating composition |
EP2420552A1 (en) | 2010-08-19 | 2012-02-22 | Infineum International Limited | EGR Equipped Diesel Engines and Lubricating Oil Compositions |
EP2453000A1 (en) | 2010-11-08 | 2012-05-16 | Infineum International Limited | Lubricating Oil Composition comprising a hydrogenated imide derived from a Diels-Alder adduct of maleic anhydride and a furan |
EP2457984A1 (en) | 2010-11-30 | 2012-05-30 | Infineum International Limited | A lubricating oil composition |
WO2012141855A1 (en) | 2011-04-15 | 2012-10-18 | R.T. Vanderbilt Company, Inc. | Molybdenum dialkyldithiocarbamate compositions and lubricating compositions containing the same |
WO2012162020A1 (en) | 2011-05-26 | 2012-11-29 | The Lubrizol Corporation | Stabilized blends containing antioxidants |
WO2012162027A1 (en) | 2011-05-26 | 2012-11-29 | The Lubrizol Corporation | Stabilized blends containing friction modifiers |
WO2013003406A1 (en) | 2011-06-29 | 2013-01-03 | Exxonmobil Research And Engineering Company | Low viscosity engine oil with superior engine wear protection |
WO2013003405A1 (en) | 2011-06-30 | 2013-01-03 | Exxonmobil Research And Engineering Company | Lubricating compositions containing polyalkylene glycol mono ethers |
WO2013003394A1 (en) | 2011-06-30 | 2013-01-03 | Exxonmobil Research And Engineering Company | Lubricating compositions containing polyetheramines |
US8586520B2 (en) | 2011-06-30 | 2013-11-19 | Exxonmobil Research And Engineering Company | Method of improving pour point of lubricating compositions containing polyalkylene glycol mono ethers |
WO2013003392A1 (en) | 2011-06-30 | 2013-01-03 | Exxonmobil Research And Engineering Company | Method of improving pour point of lubricating compositions containing polyalkylene glycol mono ethers |
EP2559748A1 (en) | 2011-08-19 | 2013-02-20 | Infineum International Limited | Lubricating oil composition |
EP2574656A1 (en) | 2011-09-28 | 2013-04-03 | Infineum International Limited | Lubricating oil compositions |
WO2013055481A1 (en) | 2011-10-10 | 2013-04-18 | Exxonmobil Research And Engineering Company | High efficiency engine oil compositions |
WO2013055482A1 (en) | 2011-10-10 | 2013-04-18 | Exxonmobil Research And Engineering Company | Lubricating compositions |
WO2013055480A1 (en) | 2011-10-10 | 2013-04-18 | Exxonmobil Research And Engineering Company | Low viscosity engine oil compositions |
EP2584025A1 (en) | 2011-10-21 | 2013-04-24 | Infineum International Limited | Lubricating oil composition |
WO2013066915A1 (en) | 2011-11-01 | 2013-05-10 | Exxonmobil Research And Engineering Company | Lubricants with improved low-temperature fuel economy |
WO2013070376A2 (en) | 2011-11-11 | 2013-05-16 | Vanderbilt Chemicals, Llc | Lubricant composition |
WO2013074498A1 (en) | 2011-11-14 | 2013-05-23 | Exxonmobil Research And Engineering Company | Method for improving engine fuel efficiency |
WO2013090051A1 (en) | 2011-12-13 | 2013-06-20 | Chemtura Corporation | Cross products and co-oligomers of phenylenediamines and aromatic amines as antioxidants for lubricants |
DE102012223638A1 (en) | 2011-12-21 | 2013-06-27 | Infineum International Ltd. | A method of reducing the rate of decrease of the basicity of a lubricating oil composition used in an engine |
WO2013096532A1 (en) | 2011-12-22 | 2013-06-27 | Exxonmobil Research And Engineering Company | Method for improving engine fuel efficiency |
WO2013101882A1 (en) | 2011-12-29 | 2013-07-04 | The Lubrizol Corporation | Limited slip friction modifiers for differentials |
WO2013123102A2 (en) | 2012-02-17 | 2013-08-22 | The Lubrizol Corporation | Lubricating composition including esterified copolymer and low dispersant levels suitable for driveline applications |
WO2013123160A1 (en) | 2012-02-17 | 2013-08-22 | The Lubrizol Corporation | Mixtures of olefin-ester copolymer with polyolefin as viscosity modifier |
WO2013151911A1 (en) | 2012-04-04 | 2013-10-10 | The Lubrizol Corporation | Bearing lubricants for pulverizing equipment |
US8703666B2 (en) | 2012-06-01 | 2014-04-22 | Exxonmobil Research And Engineering Company | Lubricant compositions and processes for preparing same |
WO2013181318A1 (en) | 2012-06-01 | 2013-12-05 | Exxonmobil Research And Engineering Company | Lubricant compostions and processes for preparing same |
WO2014008121A1 (en) | 2012-07-02 | 2014-01-09 | Exxonmobil Research And Engineering Company | Enhanced durability performance of lubricants using functionalized metal phosphate nanoplatelets |
US9228149B2 (en) | 2012-07-02 | 2016-01-05 | Exxonmobil Research And Engineering Company | Enhanced durability performance of lubricants using functionalized metal phosphate nanoplatelets |
EP2687583A1 (en) | 2012-07-17 | 2014-01-22 | Infineum International Limited | Lubricating oil compositions containing sterically hindered amines as ashless TBN sources |
EP2692839A1 (en) | 2012-07-31 | 2014-02-05 | Infineum International Limited | A lubricating oil compostion comprising a corrosion inhibitor |
EP2692840A1 (en) | 2012-07-31 | 2014-02-05 | Infineum International Limited | Lubricating oil composition |
WO2014047017A1 (en) | 2012-09-24 | 2014-03-27 | The Lubrizol Corporation | Lubricant comprising a mixture of an olefin-ester copolymer with an ethylene alpha-olefin copolymer |
WO2014066444A1 (en) | 2012-10-24 | 2014-05-01 | Exxonmobil Research And Engineering Comapny | Functionalized polymers and oligomers as corrosion inhibitors and antiwear additives |
US9487729B2 (en) | 2012-10-24 | 2016-11-08 | Exxonmobil Chemical Patents Inc. | Functionalized polymers and oligomers as corrosion inhibitors and antiwear additives |
EP2727984A1 (en) | 2012-11-02 | 2014-05-07 | Infineum International Limited | Marine engine lubrication |
EP2735603A1 (en) | 2012-11-21 | 2014-05-28 | Infineum International Limited | Marine engine lubrication |
EP2740782A1 (en) | 2012-12-10 | 2014-06-11 | Infineum International Limited | Lubricating oil compositions containing sterically hindered amines as ashless tbn sources |
WO2014105312A1 (en) | 2012-12-28 | 2014-07-03 | Chevron Oronite Company Llc | Ultra-low saps lubricants for internal combustion engines |
WO2014107315A1 (en) | 2013-01-04 | 2014-07-10 | Exxonmobil Research And Engineering Company | Method for improving engine fuel efficiency |
EP2765179A1 (en) | 2013-02-07 | 2014-08-13 | Infineum International Limited | Marine engine lubrication |
WO2014137580A1 (en) | 2013-03-07 | 2014-09-12 | The Lubrizol Corporation | Limited slip friction modifiers for differentials |
WO2014158533A1 (en) | 2013-03-14 | 2014-10-02 | Exxonmobil Research And Engineering Company | Lubricating composition providing high wear resistance |
US9708561B2 (en) | 2013-05-14 | 2017-07-18 | Basf Se | Lubricating oil composition with enhanced energy efficiency |
WO2014184068A1 (en) | 2013-05-14 | 2014-11-20 | Basf Se | Lubricating oil composition with enhanced energy efficiency |
WO2014184062A1 (en) | 2013-05-17 | 2014-11-20 | Basf Se | The use of polytetrahydrofuranes in lubricating oil compositions |
US9938484B2 (en) | 2013-05-17 | 2018-04-10 | Basf Se | Use of polytetrahydrofuranes in lubricating oil compositions |
US10150928B2 (en) | 2013-09-16 | 2018-12-11 | Basf Se | Polyester and use of polyester in lubricants |
EP2851412A1 (en) | 2013-09-24 | 2015-03-25 | Infineum International Limited | Marine engine lubrication |
WO2015050690A1 (en) | 2013-10-03 | 2015-04-09 | Exxonmobil Research And Engineering Company | Compositions with improved varnish control properties |
WO2015078707A1 (en) | 2013-11-26 | 2015-06-04 | Basf Se | The use of polyalkylene glycol esters in lubricating oil compositions |
US9708549B2 (en) | 2013-12-18 | 2017-07-18 | Chevron Phillips Chemical Company Lp | Method for making polyalphaolefins using aluminum halide catalyzed oligomerization of olefins |
WO2015095336A1 (en) | 2013-12-18 | 2015-06-25 | Chevron Phillips Chemical Company Lp | Method for making polyolefins using aluminum halide catalyzed oligomerization of olefins |
US10190072B2 (en) | 2013-12-23 | 2019-01-29 | Exxonmobil Research And Engineering Company | Method for improving engine fuel efficiency |
US9506008B2 (en) | 2013-12-23 | 2016-11-29 | Exxonmobil Research And Engineering Company | Method for improving engine fuel efficiency |
US10208269B2 (en) | 2013-12-23 | 2019-02-19 | Exxonmobil Research And Engineering Company | Low viscosity ester lubricant and method for using |
WO2015099907A1 (en) | 2013-12-23 | 2015-07-02 | Exxonmobil Research And Engineering Company | Low viscosity ester lubricant and method for using |
WO2015099819A1 (en) | 2013-12-23 | 2015-07-02 | Exxonmobil Research And Engineering Company | Method for improving engine fuel efficiency |
WO2015099820A1 (en) | 2013-12-23 | 2015-07-02 | Exxonmobil Research And Engineering Company | Method for improving engine fuel efficiency |
WO2015099821A1 (en) | 2013-12-23 | 2015-07-02 | Exxonmobil Research And Engineering Company | Method for improving engine fuel efficiency |
US9885004B2 (en) | 2013-12-23 | 2018-02-06 | Exxonmobil Research And Engineering Company | Method for improving engine fuel efficiency |
US9914893B2 (en) | 2014-01-28 | 2018-03-13 | Basf Se | Use of alkoxylated polyethylene glycols in lubricating oil compositions |
EP2913384A1 (en) | 2014-02-26 | 2015-09-02 | Infineum International Limited | A lubricating oil composition |
WO2015134129A2 (en) | 2014-03-05 | 2015-09-11 | The Lubrizol Corporation | Emulsifier components and methods of using the same |
EP2937408A1 (en) | 2014-04-22 | 2015-10-28 | Basf Se | Lubricant composition comprising an ester of a C17 alcohol mixture |
EP3415589A1 (en) | 2014-04-29 | 2018-12-19 | Infineum International Limited | Lubricating oil compositions |
EP2940110A1 (en) | 2014-04-29 | 2015-11-04 | Infineum International Limited | Lubricating oil compositions |
US9896634B2 (en) | 2014-05-08 | 2018-02-20 | Exxonmobil Research And Engineering Company | Method for preventing or reducing engine knock and pre-ignition |
WO2015171292A1 (en) | 2014-05-08 | 2015-11-12 | Exxonmobil Research And Engineering Company | Method for preventing or reducing engine knock and pre-ignition |
US20180066203A1 (en) * | 2014-05-09 | 2018-03-08 | Exxonmobil Research And Engineering Company | Method for preventing or reducing low speed pre-ignition while maintaining or improving cleanliness |
WO2015171980A1 (en) | 2014-05-09 | 2015-11-12 | Exxonmobil Research And Engineering Company | Method for preventing or reducing low speed pre-ignition |
US10519394B2 (en) * | 2014-05-09 | 2019-12-31 | Exxonmobil Research And Engineering Company | Method for preventing or reducing low speed pre-ignition while maintaining or improving cleanliness |
US20150322368A1 (en) * | 2014-05-09 | 2015-11-12 | Exxonmobil Research And Engineering Company | Method for preventing or reducing low speed pre-ignition |
WO2015171981A1 (en) | 2014-05-09 | 2015-11-12 | Exxonmobil Research And Engineering Company | Method for preventing or reducing low speed pre-ignition |
WO2015171978A1 (en) | 2014-05-09 | 2015-11-12 | Exxonmobil Research And Engineering Company | Method for preventing or reducing low speed pre-ignition |
US10000720B2 (en) | 2014-05-22 | 2018-06-19 | Basf Se | Lubricant compositions containing beta-glucans |
US9506009B2 (en) | 2014-05-29 | 2016-11-29 | Exxonmobil Research And Engineering Company | Lubricating oil compositions with engine wear protection |
WO2015183455A1 (en) | 2014-05-29 | 2015-12-03 | Exxonmobil Research And Engineering Company | Lubricating oil compositions with engine wear protection |
US10689593B2 (en) | 2014-08-15 | 2020-06-23 | Exxonmobil Research And Engineering Company | Low viscosity lubricating oil compositions for turbomachines |
US9944877B2 (en) | 2014-09-17 | 2018-04-17 | Exxonmobil Research And Engineering Company | Composition and method for preventing or reducing engine knock and pre-ignition in high compression spark ignition engines |
WO2016043944A1 (en) | 2014-09-17 | 2016-03-24 | Exxonmobil Research And Engineering Company | Composition and method for preventing or reducing engine knock and pre-ignition in high compression spark ignition engines |
US10920161B2 (en) | 2014-11-03 | 2021-02-16 | Exxonmobil Research And Engineering Company | Low transition temperature mixtures or deep eutectic solvents and processes for preparation thereof |
US9957459B2 (en) | 2014-11-03 | 2018-05-01 | Exxonmobil Research And Engineering Company | Low transition temperature mixtures or deep eutectic solvents and processes for preparation thereof |
WO2016073149A1 (en) | 2014-11-03 | 2016-05-12 | Exxonmobil Research And Engineering Company | Low transition temperature mixtures or deep eutectic solvents and processes for preparation thereof |
US9879202B2 (en) | 2014-12-04 | 2018-01-30 | Infineum International Limited | Marine engine lubrication |
EP3029133A1 (en) | 2014-12-04 | 2016-06-08 | Infineum International Limited | Marine engine lubrication |
US10364404B2 (en) | 2014-12-04 | 2019-07-30 | Infineum International Limited | Marine engine lubrication |
EP3034587A1 (en) | 2014-12-19 | 2016-06-22 | Infineum International Limited | Marine engine lubrication |
WO2016106214A1 (en) | 2014-12-24 | 2016-06-30 | Exxonmobil Research And Engineering Company | Methods for determining condition and quality of petroleum products |
WO2016106211A1 (en) | 2014-12-24 | 2016-06-30 | Exxonmobil Research And Engineering Company | Methods for authentication and identification of petroleum products |
US10000721B2 (en) | 2014-12-30 | 2018-06-19 | Exxonmobil Research And Engineering Company | Lubricating oil compositions with engine wear protection |
US10066184B2 (en) | 2014-12-30 | 2018-09-04 | Exxonmobil Research And Engineering Company | Lubricating oil compositions containing encapsulated microscale particles |
WO2016109325A1 (en) | 2014-12-30 | 2016-07-07 | Exxonmobil Research And Engineering Company | Lubricating oil compositions containing encapsulated microscale particles |
WO2016109376A1 (en) | 2014-12-30 | 2016-07-07 | Exxonmobil Research And Engineering Company | Lubricating oil compositions with engine wear protection |
WO2016109322A1 (en) | 2014-12-30 | 2016-07-07 | Exxonmobil Research And Engineering Company | Lubricating oil compositions containing encapsulated microscale particles |
US10781397B2 (en) | 2014-12-30 | 2020-09-22 | Exxonmobil Research And Engineering Company | Lubricating oil compositions with engine wear protection |
US10000717B2 (en) | 2014-12-30 | 2018-06-19 | Exxonmobil Research And Engineering Company | Lubricating oil compositions containing encapsulated microscale particles |
WO2016109382A1 (en) | 2014-12-30 | 2016-07-07 | Exxonmobil Research And Engineering Company | Lubricating oil compositions with engine wear protection |
US9926509B2 (en) | 2015-01-19 | 2018-03-27 | Exxonmobil Research And Engineering Company | Lubricating oil compositions with engine wear protection and solubility |
WO2016138939A1 (en) | 2015-03-03 | 2016-09-09 | Basf Se | Pib as high viscosity lubricant base stock |
US20180044610A1 (en) * | 2015-03-09 | 2018-02-15 | The Lubrizol Corporation | Method Of Lubricating An Internal Combustion Engine |
EP3085757A1 (en) | 2015-04-23 | 2016-10-26 | Basf Se | Stabilization of alkoxylated polytetrahydrofuranes with antioxidants |
US10119093B2 (en) | 2015-05-28 | 2018-11-06 | Exxonmobil Research And Engineering Company | Composition and method for preventing or reducing engine knock and pre-ignition in high compression spark ignition engines |
WO2016191409A1 (en) | 2015-05-28 | 2016-12-01 | Exxonmobil Research And Engineering Company | Composition and method for preventing or reducing engine knock and pre-ignition in high compression spark ignition engines |
WO2016200606A1 (en) | 2015-06-09 | 2016-12-15 | Exxonmobil Research And Engineering Company | Inverse micellar compositions containing lubricant additives |
WO2017007670A1 (en) | 2015-07-07 | 2017-01-12 | Exxonmobil Research And Engineering Company | Composition and method for preventing or reducing engine knock and pre-ignition in high compression spark ignition engines |
US10119090B2 (en) | 2015-07-07 | 2018-11-06 | Exxonmobil Research And Engineering Company | Composition and method for preventing or reducing engine knock and pre-ignition in high compression spark ignition engines |
US9732300B2 (en) | 2015-07-23 | 2017-08-15 | Chevron Phillipa Chemical Company LP | Liquid propylene oligomers and methods of making same |
EP3124581A1 (en) | 2015-07-30 | 2017-02-01 | Infineum International Limited | Dispersant additives and additive concentrates and lubricating oil compositions containing same |
US10435491B2 (en) | 2015-08-19 | 2019-10-08 | Chevron Phillips Chemical Company Lp | Method for making polyalphaolefins using ionic liquid catalyzed oligomerization of olefins |
EP3135750A1 (en) | 2015-08-26 | 2017-03-01 | Infineum International Limited | Lubricating oil compositions |
US10487288B2 (en) | 2015-09-16 | 2019-11-26 | Infineum International Limited | Additive concentrates for the formulation of lubricating oil compositions |
EP3144372A1 (en) | 2015-09-16 | 2017-03-22 | Infineum International Limited | Additive concentrates for the formulation of lubricating oil compositions |
US11168280B2 (en) | 2015-10-05 | 2021-11-09 | Infineum International Limited | Additive concentrates for the formulation of lubricating oil compositions |
EP3153568A1 (en) | 2015-10-05 | 2017-04-12 | Infineum International Limited | Additive concentrates for the formulation of lubricating oil compositions |
US10316712B2 (en) | 2015-12-18 | 2019-06-11 | Exxonmobil Research And Engineering Company | Lubricant compositions for surface finishing of materials |
US10947464B2 (en) | 2015-12-28 | 2021-03-16 | Exxonmobil Research And Engineering Company | Integrated resid deasphalting and gasification |
WO2017117178A1 (en) | 2015-12-28 | 2017-07-06 | Exxonmobil Research And Engineering Company | Bright stock production from deasphalted oil |
US10808185B2 (en) | 2015-12-28 | 2020-10-20 | Exxonmobil Research And Engineering Company | Bright stock production from low severity resid deasphalting |
US10647925B2 (en) | 2015-12-28 | 2020-05-12 | Exxonmobil Research And Engineering Company | Fuel components from hydroprocessed deasphalted oils |
US10590360B2 (en) | 2015-12-28 | 2020-03-17 | Exxonmobil Research And Engineering Company | Bright stock production from deasphalted oil |
US10550341B2 (en) | 2015-12-28 | 2020-02-04 | Exxonmobil Research And Engineering Company | Sequential deasphalting for base stock production |
US10550335B2 (en) | 2015-12-28 | 2020-02-04 | Exxonmobil Research And Engineering Company | Fluxed deasphalter rock fuel oil blend component oils |
EP3192858A1 (en) | 2016-01-15 | 2017-07-19 | Infineum International Limited | Use of lubricating oil composition |
WO2017146897A1 (en) | 2016-02-26 | 2017-08-31 | Exxonmobil Research And Engineering Company | Lubricant compositions containing controlled release additives |
WO2017146896A1 (en) | 2016-02-26 | 2017-08-31 | Exxonmobil Research And Engineering Company | Lubricant compositions containing controlled release additives |
US10377962B2 (en) | 2016-02-26 | 2019-08-13 | Exxonmobil Research And Engineering Company | Lubricant compositions containing controlled release additives |
US10377961B2 (en) | 2016-02-26 | 2019-08-13 | Exxonmobil Research And Engineering Company | Lubricant compositions containing controlled release additives |
EP3222698A1 (en) | 2016-03-22 | 2017-09-27 | Infineum International Limited | Additive concentrates |
US11292980B2 (en) | 2016-03-22 | 2022-04-05 | Infineum International Ltd | Additive concentrates |
US11299690B2 (en) | 2016-03-22 | 2022-04-12 | Infineum International Ltd. | Additive concentrates |
WO2017172254A1 (en) | 2016-03-31 | 2017-10-05 | Exxonmobil Research And Engineering Company | Lubricant compositions |
US9951290B2 (en) | 2016-03-31 | 2018-04-24 | Exxonmobil Research And Engineering Company | Lubricant compositions |
US10494579B2 (en) | 2016-04-26 | 2019-12-03 | Exxonmobil Research And Engineering Company | Naphthene-containing distillate stream compositions and uses thereof |
EP3249029A1 (en) | 2016-05-23 | 2017-11-29 | Infineum International Limited | Highly borated dispersant concentrates for lubricating oil compositions and methods for forming same |
US10487286B2 (en) | 2016-05-23 | 2019-11-26 | Infineum International Ltd. | Highly borated dispersant concentrates for lubricating oil compositions and methods for forming same |
EP3252130A1 (en) | 2016-06-03 | 2017-12-06 | Infineum International Limited | Additive package and lubricating oil composition |
EP3257921A1 (en) | 2016-06-14 | 2017-12-20 | Infineum International Limited | Lubricating oil additives |
EP3263676A2 (en) | 2016-06-30 | 2018-01-03 | Infineum International Limited | Lubricating oil compositions |
WO2018013249A1 (en) | 2016-07-12 | 2018-01-18 | Chevron Phillips Chemical Company Lp | Decene oligomers |
US10647626B2 (en) | 2016-07-12 | 2020-05-12 | Chevron Phillips Chemical Company Lp | Decene oligomers |
WO2018026982A1 (en) | 2016-08-03 | 2018-02-08 | Exxonmobil Research And Engineering Company | Lubricating engine oil for improved wear protection and fuel efficiency |
US10640725B2 (en) | 2016-08-05 | 2020-05-05 | Rutgers, The State University Of New Jersey | Thermocleavable friction modifiers and methods thereof |
WO2018027227A1 (en) | 2016-08-05 | 2018-02-08 | Rutgers, The State University Of New Jersey | Thermocleavable friction modifiers and methods thereof |
WO2018050484A1 (en) | 2016-09-13 | 2018-03-22 | Basf Se | Lubricant compositions containing diurea compounds |
EP3293246A1 (en) | 2016-09-13 | 2018-03-14 | Basf Se | Lubricant compositions containing diurea compounds |
WO2018053098A1 (en) | 2016-09-14 | 2018-03-22 | The Lubrizol Corporation | Lubricating composition comprising sulfonate detergent and ashless hydrocarbyl phenolic compound |
WO2018057377A1 (en) | 2016-09-20 | 2018-03-29 | Exxonmobil Research And Engineering Company | Non-newtonian engine oil with superior engine wear protection and fuel economy |
US10479956B2 (en) | 2016-09-20 | 2019-11-19 | Exxonmobil Research And Engineering Company | Non-newtonian engine oil with superior engine wear protection and fuel economy |
WO2018067902A1 (en) | 2016-10-07 | 2018-04-12 | Exxonmobil Research And Engineering Company | Lubricating oil compositions for electric vehicle powertrains |
WO2018067908A1 (en) | 2016-10-07 | 2018-04-12 | Exxonmobil Research And Engineering Company | Low conductivity lubricating oils for electric and hybrid vehicles |
WO2018067903A1 (en) | 2016-10-07 | 2018-04-12 | Exxonmobil Research And Engineering Company | Method for controlling electrical conductivity of lubricating oils in electric vehicle powertrains |
WO2018067906A1 (en) | 2016-10-07 | 2018-04-12 | Exxonmobil Research And Engineering Company | High conductivity lubricating oils for electric and hybrid vehicles |
WO2018067905A1 (en) | 2016-10-07 | 2018-04-12 | Exxonmobil Research And Engineering Company | Method for preventing or minimizing electrostatic discharge and dielectric breakdown in electric vehicle powertrains |
EP3315591A1 (en) | 2016-10-28 | 2018-05-02 | Basf Se | Energy efficient lubricant compositions |
EP3321347A1 (en) | 2016-11-14 | 2018-05-16 | Infineum International Limited | Lubricating oil additives based on overbased gemini surfactant |
US10829708B2 (en) | 2016-12-19 | 2020-11-10 | Exxonmobil Research And Engineering Company | Composition and method for preventing or reducing engine knock and pre-ignition in high compression spark ignition engines |
WO2018118477A1 (en) | 2016-12-19 | 2018-06-28 | Exxonmobil Research And Engineering Company | Composition and method for preventing or reducing engine knock and pre-ignition compression spark ignition engines |
WO2018125956A1 (en) | 2016-12-30 | 2018-07-05 | Exxonmobil Research And Engineering Company | Low viscosity lubricating oil compositions for turbomachines |
US10647936B2 (en) | 2016-12-30 | 2020-05-12 | Exxonmobil Research And Engineering Company | Method for improving lubricant antifoaming performance and filterability |
WO2018144167A1 (en) | 2017-02-01 | 2018-08-09 | Exxonmobil Research And Engineering Company | Lubricating engine oil and method for improving engine fuel efficiency |
WO2018144166A1 (en) | 2017-02-01 | 2018-08-09 | Exxonmobil Research And Engineering Company | Lubricating engine oil and method for improving engine fuel efficiency |
US10793801B2 (en) | 2017-02-06 | 2020-10-06 | Exxonmobil Chemical Patents Inc. | Low transition temperature mixtures and lubricating oils containing the same |
WO2018156304A1 (en) | 2017-02-21 | 2018-08-30 | Exxonmobil Research And Engineering Company | Lubricating oil compositions and methods of use thereof |
US10662391B2 (en) | 2017-02-21 | 2020-05-26 | Chevron Oronite Company Llc | Lubricating oil compositions containing borated dispersants and amine compounds and methods of making and using same |
US10487289B2 (en) | 2017-02-21 | 2019-11-26 | Exxonmobil Research And Engineering Company | Lubricating oil compositions and methods of use thereof |
EP3366755A1 (en) | 2017-02-22 | 2018-08-29 | Infineum International Limited | Improvements in and relating to lubricating compositions |
EP3369802A1 (en) | 2017-03-01 | 2018-09-05 | Infineum International Limited | Improvements in and relating to lubricating compositions |
WO2018170110A1 (en) | 2017-03-16 | 2018-09-20 | Chevron Phillips Chemical Company Lp | Lubricant compositions containing hexene-based oligomers |
US10240102B2 (en) | 2017-03-16 | 2019-03-26 | Chevron Phillips Chemical Company, Lp | Lubricant compositions containing hexene-based oligomers |
US10876062B2 (en) | 2017-03-24 | 2020-12-29 | Exxonmobil Chemical Patents Inc. | Cold cranking simulator viscosity boosting base stocks and lubricating oil formulations containing the same |
US10858610B2 (en) | 2017-03-24 | 2020-12-08 | Exxonmobil Chemical Patents Inc. | Cold cranking simulator viscosity boosting base stocks and lubricating oil formulations containing the same |
US10738258B2 (en) | 2017-03-24 | 2020-08-11 | Exxonmobil Research And Engineering Company | Method for improving engine fuel efficiency and energy efficiency |
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EP3778841A1 (en) | 2019-08-15 | 2021-02-17 | Infineum International Limited | Method for reducing piston deposits in a marine diesel engine |
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WO2021138285A1 (en) | 2020-01-03 | 2021-07-08 | Afton Chemical Corporation | Silicone functionlized viscosity index improver |
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EP4159832A1 (en) | 2021-10-04 | 2023-04-05 | Infineum International Limited | Lubricating oil compositions |
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EP4174152A1 (en) | 2021-10-29 | 2023-05-03 | Infineum International Limited | Ionic liquid composition |
US11859149B2 (en) | 2021-10-29 | 2024-01-02 | Infineum International Limited | Ionic liquid composition |
EP4180505A1 (en) | 2021-11-15 | 2023-05-17 | Infineum International Limited | Improvements in marine fuels |
WO2023122405A1 (en) | 2021-12-21 | 2023-06-29 | ExxonMobil Technology and Engineering Company | Engine oil lubricant compostions and methods for making same with superior oil consumption |
EP4303287A1 (en) | 2022-07-06 | 2024-01-10 | Infineum International Limited | Lubricating oil compositions |
EP4353804A1 (en) | 2022-10-11 | 2024-04-17 | Infineum International Limited | Functionalized c4 to c5 olefin polymers and lubricant compositions containing such |
EP4353805A1 (en) | 2022-10-11 | 2024-04-17 | Infineum International Limited | Lubricant composition containing metal alkanoate |
EP4357443A1 (en) | 2022-10-18 | 2024-04-24 | Infineum International Limited | Lubricating oil compositions |
Also Published As
Publication number | Publication date |
---|---|
GB1021182A (en) | 1966-03-02 |
DE1274776B (en) | 1968-08-08 |
JPS4936926B1 (en) | 1974-10-04 |
DE1644907A1 (en) | 1971-02-18 |
JPS4833242B1 (en) | 1973-10-12 |
US3254025A (en) | 1966-05-31 |
FR87407E (en) | 1966-08-05 |
GB1021183A (en) | 1966-03-02 |
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