US3448047A - Lube oil dispersants - Google Patents
Lube oil dispersants Download PDFInfo
- Publication number
- US3448047A US3448047A US628553A US3448047DA US3448047A US 3448047 A US3448047 A US 3448047A US 628553 A US628553 A US 628553A US 3448047D A US3448047D A US 3448047DA US 3448047 A US3448047 A US 3448047A
- Authority
- US
- United States
- Prior art keywords
- oil
- alkyl
- additives
- lubricating oil
- lubricating
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M159/00—Lubricating compositions characterised by the additive being of unknown or incompletely defined constitution
- C10M159/12—Reaction products
- C10M159/16—Reaction products obtained by Mannich reactions
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2205/00—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
- C10M2207/28—Esters
- C10M2207/281—Esters of (cyclo)aliphatic monocarboxylic acids
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- 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
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
- C10M2207/28—Esters
- C10M2207/283—Esters of polyhydroxy compounds
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
- C10M2207/28—Esters
- C10M2207/286—Esters of polymerised unsaturated acids
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
- C10M2207/28—Esters
- C10M2207/34—Esters having a hydrocarbon substituent of thirty or more carbon atoms, e.g. substituted succinic acid derivatives
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2209/00—Organic macromolecular compounds containing oxygen as ingredients in lubricant compositions
- C10M2209/10—Macromolecular compoundss obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
- C10M2209/103—Polyethers, i.e. containing di- or higher polyoxyalkylene groups
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- 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
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
- C10M2215/22—Heterocyclic nitrogen compounds
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
- C10M2215/22—Heterocyclic nitrogen compounds
- C10M2215/221—Six-membered rings containing nitrogen and carbon only
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
- C10M2215/22—Heterocyclic nitrogen compounds
- C10M2215/225—Heterocyclic nitrogen compounds the rings containing both nitrogen and oxygen
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
- C10M2215/22—Heterocyclic nitrogen compounds
- C10M2215/225—Heterocyclic nitrogen compounds the rings containing both nitrogen and oxygen
- C10M2215/226—Morpholines
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
- C10M2215/26—Amines
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
- C10M2215/30—Heterocyclic compounds
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2217/00—Organic macromolecular compounds containing nitrogen as ingredients in lubricant compositions
- C10M2217/04—Macromolecular compounds from nitrogen-containing monomers obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
- C10M2217/046—Polyamines, i.e. macromoleculars obtained by condensation of more than eleven amine monomers
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2217/00—Organic macromolecular compounds containing nitrogen as ingredients in lubricant compositions
- C10M2217/06—Macromolecular compounds obtained by functionalisation op polymers with a nitrogen containing compound
Landscapes
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Organic Chemistry (AREA)
- Lubricants (AREA)
Description
United States Patent U.S. Cl. 252-515 8 Claims ABSTRACT OF THE DISCLOSURE Modified Mannich type condensation products from a polymer substituted phenol, an alkylene polyamine and formaldehyde wherein a portion of the alkylene polyamine is replaced with an alkyl-substituted pyridine. These products are useful as lubricating oil dispersants.
Background of the invention This invention relates to modified Mannich condensation products as novel compounds and more particularly relates to novel condensation products C and higher alkyl-substituted phenols, formaldehyde, alkylene polyamine, and an alkyl-substituted pyridine; their preparation and their use as detergent-dispersant addition agents for lubricant oil formulations.
The prior art portrays a need for improved engine lubricating oil additives which function as dispersants to retain in suspension insoluble particles such as the prodducts of fuel combustion, those of incipient oxidation, and those of lubricant deterioration. The control of the deterioration of lubricating oils has long been a problem, particularly in the formulation of the compositions of lubricating oil additives.
It has been known for many years that deterioration of hydrocarbon lubricating oils causes the formation of substances which deleteriously affect the surfaces which the lubricants are developed to protect through the maintenance of reduced frictional forces between said surfaces. Lubricating oil deterioration not only causes the formation of surface-deleterious substances, but it also results in the agglomeration of sludge-like materials in the lubricants and the deposition of varnish on the surfaces.
For many years it has been a practice to include as additives in lubricating oils, chemical compositions which tend to reduce oil deterioration and the consequent formation of the sludgeand varnish-like material. Broadly included in the classification of additives are corrosion and oxidation inhibitors, and dispersing agents. These additives generally function to reduce the corrosion of the surfaces to be protected, to stabilize the lubricating oil, to inhibit deterioration by oxidation, and to function as dispersants which tend to prevent the agglomeration of sludge and the deposition of varnish and sludge caused by the formation of the products of deterioration.
Frequently, the inclusion into lubricating oils of corrosion, oxidation, and dispersant agents is highly desirable; however, the problems of compatibility of these three or more functional agents creates serious difficulties in the formulation of useful additive-containing lubricating oils. Much research and development effort has been expended in the search for improved lubricating oil additives which function in the above-enumerated manner. The research efforts have been directed toward the development of three or more separate agents, as well as a single agent, or a plurality of compatible agents that will perform all of the desired functions when incorporated into hydrocarbon lubricating oils.
Various Mannich condensation products are known in the prior art as lubricating oil additives; however, the
teachings of the disclosures indicate that these Mannich products have previously been considered for use as oxidation inhibitors and as anti-wear additives. The former tend to reduce the rate of formation of oxidation products and the latter tend to coat surfaces with films and reduce friction resulting in less wear; consequently, there is some reduction of particulate and product contamination of the lubricating oil medium. It is also well-known that various Mannich products produced for use as oxidation inhibitors and anti-wear additives demonstrate limited solubility in lubricating oil, which factor is also an undesirable characteristic of an additive. In view of the above, it has long been attempted to develop Mannich products and derivatives thereof which have novel functional properties as well as improved solubility in lubricating oils when incorporated therein.
Accordingly, it is an object of this invention to provide new compositions of matter.
It is an additional object of this invention to provide new compositions of matter which are useful as dispersants in lubricating oil compositions.
Another object of this invention is to provide lubricating oil dispersants which have improved solubility in said oil and which exhibit superior compatibility with other oil including additives.
An additional object of this invention is to provide a novel process for the preparation of compositions useful as dispersants.
Another object of this invention is to provide improved lubricating compositions.
Other objects and advantages of the invention disclosed and claimed herein will become apparent from the specification, including various embodiments, examples, and the claims.
Summary of the invention It has been discovered that improved dispersant-detergent compositions for lubrication oils can be made by condensing a phenol substituted with a high molecular weight hydrocarbon with an aldehyde, an alkylene polyamine, and an alkyl-substituted pyridine. Suitably, in carrying out the condensation, the reactants are used in the following ratios: 1 mole of high molecular weight substituted phenol, 1.53.0 moles of aldehyde, 0.5-1.5 moles of alkylene polyamine, and 0.5-1.5 moles of alkyl-substituted pyridine.
The high molecular weight hydrocarbon-substituted phenols suitable for use in this invention are those that have a number average molecular weight in the range from 800 to 2,500. The high molecular weight alkyl-substituted phenols are obtained by the alkylation in the presence of B1 or aluminum chloride or generally in the presence of a Friedel-Crafts type catalyst of phenol with C and higher carbon content polypropylenes or polybutenes. Copolymers of polypropylene with monomers copolymerizable therewith may be employed wherein the copolymer molecule contains at least polypropylene units. C0- polymers of butenes (butene 1, butene 2 and isobutylene) with monomers copolymerizable therewith may also be employed wherein the copolymer molecule contains at least 90% butene units.
More specifically, suitable high molecular weight alkylphenols are described in a copending application, S.N. 484,758, filed Sept. 2, 1965.
The aldehyde suitable for use in this invention is formaldehyde. Formaldehyde per se need not be used as a reactant in the process of this invention. Suitable formaldehyde yielding sources may be used such as, aqueous and alcohol solutions of formaldehyde, paraformaldehyde, and trioxymethylene. These, as Well as formaldehyde itself, may be used to provide the quantities of formaldehyde required for the purposes of this invention.
Suitable alkylene polyamine reactants include ethylene diamine, diethylene triamine, triethylene tetramine, tetraethylene pentamine, pentaethylene hexamine, hexaethylene heptamine, heptaethylene octamine, octaethylene nonamine, nonaethylene decamine and decaethylene undecamine and mixtures of such amines having nitrogen contents corresponding to the alkylene polyamines according to the formula,
where A is divalent ethylene and n is 1-10. Corresponding propylenepolyamines such as propylene diamine and di-, tritetra-, penta-propylene, tri-, tetraand penta-amines are also suitable reactants. The alkylene polyamines are usually obtained by the reaction of ammonia and dihalo alkanes, such as dichloro alkanes.
The alkyl-substituted pyridines suitable for use in this invention are pyridines wherein the alkyl group ranges in size from C to about C The preferred substituted pyridines are the methylpyridines and more specifically, alphamethylpyridine or alpha-picoline.
PREPARATION The following procedure was used in preparing the novel additive described and claimed herein.
One mole (850 grams) of a C alkylated phenol obtained in a BF catalyzed alkylation of phenol with a C polypropylene, 1 mole (93 grams) of picoline, and 1 mole (189 grams) of a tetraethylene pentamine were combined in atlask. This mixture was heated to about 35-40 C. to reduce the viscosity and to allow the components to be stirred. Two moles (162 grams) of a 37% formaldehyde solution was added slowly over a period of one hour. After stirring under a nitrogen blanket for about one additional hour the reaction products were heated. The exothermic heat generated raised the temperature to about 60 C. during the addition of the formaldehyde; however, at the end of the stirring the temperature had been reduced to about 47 C. The temperature was raised slowly over a period of about five hours to about 100 C. and the mixture was allowed to stand under a nitrogen blanket for about 12 hours. Subsequently, water was stripped from the system by heating to about 150 C. during a period of about six hours, and after nitrogen blowing at about 150 C. for about one additional hour the reaction product was cooled and removed from the flask. The product yield was about 90%.
The reaction product of the above described preparation was found to have a pH of about 10, a total base number of about 149 milligrams KOH per gram of product, a nitrogen content of about 5.84%, and an average molecular weight of about 1371. The material was dissolved in lubricating oil at concentrations shown and was then used in the following tests.
LABORATORY OXIDATION TEST A 300 gram sample of lubricating oil containing the additives of this invention was heated to about 166 C. with stirring. A glass rod was inserted in the oil to measure the varnish formed thereon. A copper ribbon having an area of about five square inches and a ribbon of iron having an area of about ten square inches were immersed in the lubricant oil additives containing sample to function as catalysts. Intermediate inspections were made and at the end of 72 hours varnish formation on the glass rod was estimated visually and reported on a scale of 1-10, where was perfectly clean. The acidity developed in the oil, the pentane insolubles, and the viscosity increase of the oil were also determined. Table I shows the results of the testing of the novel additives of this invention in accordance with the foregoing.
TABLE I.LABORATORY OXIDATION TEST RESULTS Acidity mg. Pentane insolnbles Additive Varnish KOH per g. (percent) concentration,
percent 48 72 24 48 72 24 48 72 A used oil analysis was conducted to develop comparative data for various concentrations of the novel additives of this invention and the results are portrayed below in Table II.
TABLE II.USED OIL ANALYSIS Used Additive Conc. New, 2% 2% 5% Vrs. 05 336. 9 343 401. 3 V18. 100 SSU 1516.9 1587 1860.8 Vis. 210 SSU 101. 7 101. 5 110. 2
It is apparent from the above data that the lubricant containing the novel additive of this invention has excellent stability and provides a high degree of cleanhness.
LINCOLN ENGINE TESTS Phase 1 Phase 2 Phase 3 Duration (min.) 45 1 2 75 Speed, r.p.m 500 2500 2500 Lead, brake horsepower No load 105 Temperature, F.:
Water jacket -120 130 -175 Oil sum 120-125 -180 205-210 Air/fuel ratio 9. 5:|=0. 5 15. 5i0. 5 15. 5:0. 5
1 Hour.
The 4-hour cycle is repeated a total of 48 times (192 hours running time). After each 16 hours of operation the engine is shut down for eight hours. The oil level is adjusted with fresh oil to a level of five quarts. At the termination of the test, the hot oil is drained. The engine is then disassembled and examined for deposits of varnish and sludge among other observable results.
In the Lincoln M.S. Test Sequence V, after the formulated lubricant oil has been tested and the engine disassembled for inspection of the parts thereof for sludge and varnish deposits among other inspections, the total varnish and sludge ratings are made from the individual ratings of the following engine parts.
Varnish: Sludge:
Piston Push Rod Chamber Rocker Arm Cover Rocker Arm Assembly Push Rod Cover Cylinder Walls Oil Pan Rocker Arm Cover Oil Screen Oil Pan Push Rod Cover Timing Gear Cover Valve Deck Lincoln Engine Tests No. 1, No. 2, and No. 3
A triple Lincoln engine test was run on a lubricating oil containing 2.4% by weight of the novel additive of this invention along with 3% by weight of a high temperature detergent, 3% by weight of a high base sulfonate, and 1% by weight of a. zinc dialkyl dithiophosphate oxidation inhibitor. All of the ingredients except the additive of this invention are readily available in the commercial marketplace. The results of the tests are shown below in Table IH.
TABLE IH.-LINCOLN ENGINE TEST RESULTS 8 p uggmg 1 con- Test N o. Sludge rating rating (percent) sumption 46 46 Low. 40 40 0 0. 43 39 Average.
Lincoln Engine Test No. 4
TABLE IV .-Lincoln engine test results Test No. 4 Sludge rating 43 Average rating 39 Oil ring plugging (percent) 0 Oil screen plugging 5 FORD 289 ENGINE TESTS Two tests designated Test No. 5 and Test No. 6 were conducted on lubricating oils of different formulations in the Ford 289 cubic inch displacement engine in a manner similar to the above described Lincoln tests, each of these tests are well-known to those of ordinary skill in the art. I
289 Engine Test No. 5
This test was conducted on a lubricating oil formulation containing 3% by weight of a high-temperature detergent, 3% by weight of a sulfonate anti-rust agent, 1% of a zinc dialkyl dithiophosphate oxidation inhibitor, and 0.25 of an anti-wear agent, all readily available commercially. This formulation also contained 2.4 of the novel additive of this invention. The results obtained in this test are as follows in Table V:
TABLE V.--Ford 289 engine test results Test No. 5 Sludge rating 47 Average rating 45 Oil ring plugging, percent 0 Oil screen plugging 0 289 Engine Test No. 6
This lubricating oil formulation contained about 9.22% by weight of a polymethacrylate viscosity index improver, about 3.37% by weight of a high-temperature detergent,
about 3.66% by weight of a sulfonate anti-rust agent,
about 1.27% by weight of a zinc dialkyl dithiophosphate oxidation inhibitor, and about 0.315% by weight of an anti-wear agent, all readily available commercially. The formulation also included about 2.4% by weight of the novel additive of this invention. The results of the test were as follows in Table VI:
TABLE VI.Ford 289 engine test results Test No. 6
The dispersants prepared as disclosed herein can be used as addition agents in lubricating oils and especially in .lu-bn'cating oils for use in internal combustion engines. The addition agents impart excellent low-temperature dispersancy characteristics to the lubricating oil. Although amounts of the dispersancy addition agent may be varied as desired, it is believed advantageous to use at least about 1 weight percent and up to 10 weight percent of the addition agent of this invention and preferably 2-5 weight percent in a suitable lubricating oil.
Although the preferred lubricating oils are the mineral lubricating oils, the use of the additive compositions is not restricted thereto. Other lubricating oil bases can be used, such as hydrocarbon oils, both natural and synthetic, for example, those obtained 'by the polymerization of olefins, as well as synthetic lubricating oils of the alkylene oxide type and the monoand polycarboxylic acid ester type, such as the esters of adipic acid, sebacic acid, azelaic acid; it is also contemplated that various other well-known additives, such as anti-oxidants, antifoam agents, pour point depressors, extreme pressure agents, corrosion inhibitors, anti-wear agents, etc., may be incorporated in lubricating oils containing the additives of our invention.
Concentrates of a suitable oil base containing more than 10 percent, for example, up to 75 percent or more, of the additive of this invention alone or in combination with other additives may be prepared and can be used for blending with hydrocarbon oils or other oils in the proportions desired for the particular conditions of use to give a finished lubricating product containing the additives of this invention. In order to exemplify the use of the reaction products prepared in accordance herewith as low dispersancy lubricating oil addition agents, examples of formulated lubricating oils containing such reaction products were prepared.
While in the foregoing specification this invention had been described in relation to preferred embodiments thereof, and many details have been set forth for the purpose of illustration, it will be apparent to those skilled in the art that the invention is susceptible to other embodiments and that many of the details set forth herein can be varied considerably without departing from the basic principles of the invention.
Having described the invention, what is claimed is:
1. The condensation product of (a) formaldehyde, (b) an alkyl substituted phenol wherein the alkyl substituent contains at least 50 carbon atoms, (c) an alkyl sub stituted pyridine wherein the alkyl substituent contains from 1 to 8 carbon atoms, and (d) an alkylene polyamine having the formula:
wherein A is a divalent ethylene or propylene group and n is 1-10, said reactants being used in the ratios of 1.5-3.0 moles of formaldehyde, 1 mole of alkyl substituted phenol, 0.5-1.5 moles of alkyl substituted pyridine, and 0.5-1.5 moles of alkylene polyamine.
2. The product defined in claim 1 wherein the alkyl substituted phenol has a number average molecular weight of from 800 to 2,500.
3. The product defined in claim 2 wherein the alkyl substituent for the phenol is derived from either polypropylene or polybutene.
4. The product defined in claim 3 wherein the alkyl substituted pyridine is either alpha picoline or alpha methyl pyridine.
5. A composition com rising a major portion of a lubricating oil and from about 1-10 weight percent of the condensation product of (a) formaldehyde, (b) an alkyl substituted phenol wherein the alkyl substituentcontains at least 50 carbon atoms, (c) an alkyl substituted pyridine wherein the alkyl substituent contains from 1 to 8 carbon atoms, and (d) an alkylene polyamine having the formula:
HN(ANH),,H
wherein A is a divalent ethylene or propylene group and n is l-10, said reactants being used in the ratios of 1.5-3.0 moles of formaldehyde, 1 mole of alkyl substituted phenol, 0.5-1.5 moles of alkyl substtiuted pyridine, and 0.5-1.5 moles of alkylene polyamine.
6. The composition defined in claim 5 wherein the alkyl substituted phenol has a number average molecular weight of from 800 to 2,500.
7. The composition defined in claim 6 wherein the alkyl substituent for the phenol is derived from either polypropylene or polybutene.
8. The composition defined in claim 7 wherein the alkyl substituted pyridine is either alpha picoline or alpha methyl pyridine.
References Cited UNITED STATES PATENTS 3,340,192 9/1967 Henley 252--5l.5 3,360,464 12/1967 Otto 252'51.5
US. Cl. X.R. 260-4045
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US62855367A | 1967-04-05 | 1967-04-05 |
Publications (1)
Publication Number | Publication Date |
---|---|
US3448047A true US3448047A (en) | 1969-06-03 |
Family
ID=24519385
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US628553A Expired - Lifetime US3448047A (en) | 1967-04-05 | 1967-04-05 | Lube oil dispersants |
Country Status (1)
Country | Link |
---|---|
US (1) | US3448047A (en) |
Cited By (72)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3725480A (en) * | 1968-11-08 | 1973-04-03 | Standard Oil Co | Ashless oil additives |
US4054422A (en) * | 1975-09-12 | 1977-10-18 | E. I. Du Pont De Nemours & Company | Mannich bases containing tertiary amines and fuel compositions containing said mannich bases |
US4454059A (en) * | 1976-11-12 | 1984-06-12 | The Lubrizol Corporation | Nitrogenous dispersants, lubricants and concentrates containing said nitrogenous dispersants |
EP0399764A1 (en) | 1989-05-22 | 1990-11-28 | Ethyl Petroleum Additives Limited | Lubricant compositions |
US5124055A (en) * | 1988-03-31 | 1992-06-23 | Ethyl Petroleum Additives, Inc. | Lubricating oil composition |
EP0558835A1 (en) | 1992-01-30 | 1993-09-08 | Albemarle Corporation | Biodegradable lubricants and functional fluids |
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 |
US5814111A (en) * | 1995-03-14 | 1998-09-29 | Shell Oil Company | Gasoline compositions |
US6627584B2 (en) | 2002-01-28 | 2003-09-30 | Ethyl Corporation | Automatic transmission fluid additive comprising reaction product of hydrocarbyl acrylates and dihydrocarbyldithiophosphoric acids |
US20040147410A1 (en) * | 2003-01-15 | 2004-07-29 | Milner Jeffrey L | Extended drain, thermally stable, gear oil formulations |
US20050065043A1 (en) * | 2003-09-23 | 2005-03-24 | Henly Timothy J. | Power transmission fluids having extended durability |
US20050070446A1 (en) * | 2003-09-25 | 2005-03-31 | Ethyl Petroleum Additives, Inc. | Boron free automotive gear oil |
US20050101494A1 (en) * | 2003-11-10 | 2005-05-12 | Iyer Ramnath N. | Lubricant compositions for power transmitting fluids |
US20050101496A1 (en) * | 2003-11-06 | 2005-05-12 | Loper John T. | Hydrocarbyl dispersants and compositions containing the dispersants |
US20050143265A1 (en) * | 2003-12-31 | 2005-06-30 | Loper John T. | Hydrocarbyl dispersants including pendant polar functional groups |
US20050181959A1 (en) * | 2004-02-17 | 2005-08-18 | Esche Carl K.Jr. | Lubricant and fuel additives derived from treated amines |
EP1568759A2 (en) | 2004-02-27 | 2005-08-31 | Afton Chemical Corporation | Power transmission fluids |
US20050202979A1 (en) * | 2004-03-10 | 2005-09-15 | Ethyl Petroleum Additives, Inc. | Power transmission fluids with enhanced extreme pressure characteristics |
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 |
EP1669435A1 (en) | 2004-12-10 | 2006-06-14 | Afton Chemical Corporation | Dispersant reaction product with antioxidant capability |
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 |
US20060264339A1 (en) * | 2005-05-19 | 2006-11-23 | Devlin Mark T | Power transmission fluids with enhanced lifetime characteristics |
US20070111906A1 (en) * | 2005-11-12 | 2007-05-17 | Milner Jeffrey L | Relatively low viscosity transmission fluids |
US20080015125A1 (en) * | 2006-07-14 | 2008-01-17 | Devlin Mark T | Lubricant compositions |
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 |
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 |
US20080274921A1 (en) * | 2007-05-04 | 2008-11-06 | Ian Macpherson | Environmentally-Friendly Lubricant Compositions |
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 |
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 |
US20090156445A1 (en) * | 2007-12-13 | 2009-06-18 | Lam William Y | Lubricant composition suitable for engines fueled by alternate fuels |
US20090233822A1 (en) * | 2008-03-11 | 2009-09-17 | Afton Chemical Corporation | Ultra-low sulfur clutch-only transmission fluids |
US20090233823A1 (en) * | 2008-03-11 | 2009-09-17 | Volkswagen Aktiengesellschaft | Method for lubricating a clutch-only automatic transmission component requiring 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 |
WO2010096325A1 (en) | 2009-02-18 | 2010-08-26 | The Lubrizol Corporation | Amine derivatives as friction modifiers in lubricants |
EP2366762A1 (en) | 2002-10-04 | 2011-09-21 | R.T. Vanderbilt Company Inc. | Synergistic organoborate compositions and lubricating compositions containing same |
EP2371933A1 (en) | 2006-02-06 | 2011-10-05 | The Lubrizol Corporation | Tartaric acid derivatives as fuel economy improvers and antiwear agents in crankcase oils and preparation thereof |
WO2011143051A1 (en) | 2010-05-12 | 2011-11-17 | The Lubrizol Corporation | Tartaric acid derivatives in hths fluids |
WO2012033668A1 (en) | 2010-09-07 | 2012-03-15 | The Lubrizol Corporation | Hydroxychroman derivatives as engine oil antioxidants |
WO2012141855A1 (en) | 2011-04-15 | 2012-10-18 | R.T. Vanderbilt Company, Inc. | Molybdenum dialkyldithiocarbamate compositions and lubricating compositions containing the same |
WO2012154708A1 (en) | 2011-05-12 | 2012-11-15 | The Lubrizol Corporation | Aromatic imides and esters as lubricant additives |
WO2013013026A1 (en) | 2011-07-21 | 2013-01-24 | The Lubrizol Corporation | Carboxylic pyrrolidinones and methods of use thereof |
WO2013012987A1 (en) | 2011-07-21 | 2013-01-24 | The Lubrizol Corporation | Overbased friction modifiers and methods of use thereof |
WO2013070376A2 (en) | 2011-11-11 | 2013-05-16 | Vanderbilt Chemicals, Llc | Lubricant composition |
WO2014088814A1 (en) | 2012-12-07 | 2014-06-12 | The Lubrizol Corporation | Pyran dispersants |
WO2015048011A1 (en) | 2013-09-25 | 2015-04-02 | 3M Innovative Properties Company | Multi-layered polishing pads |
WO2015047939A1 (en) | 2013-09-25 | 2015-04-02 | 3M Innovative Properties Company | Composite ceramic abrasive polishing solution |
WO2015184276A1 (en) | 2014-05-30 | 2015-12-03 | The Lubrizol Corporation | Epoxide quaternized quaternary ammonium salts |
WO2015184301A2 (en) | 2014-05-30 | 2015-12-03 | The Lubrizol Corporation | Coupled quaternary ammonium salts |
WO2015184251A1 (en) | 2014-05-30 | 2015-12-03 | The Lubrizol Corporation | Branched amine containing quaternary ammonium salts |
WO2015183908A1 (en) | 2014-05-30 | 2015-12-03 | The Lubrizol Corporation | Low molecular weight imide containing quaternary ammonium salts |
WO2015184254A1 (en) | 2014-05-30 | 2015-12-03 | The Lubrizol Corporation | High molecular weight amide/ester containing quaternary ammonium salts |
WO2015184247A1 (en) | 2014-05-30 | 2015-12-03 | The Lubrizol Corporation | High molecular weight imide containing quaternary ammonium salts |
WO2015183916A1 (en) | 2014-05-30 | 2015-12-03 | The Lubrizol Corporation | Low molecular weight amide/ester containing quaternary ammonium salts |
WO2015184280A1 (en) | 2014-05-30 | 2015-12-03 | The Lubrizol Corporation | Imidazole containing quaternary ammonium salts |
WO2015200592A1 (en) | 2014-06-27 | 2015-12-30 | The Lubrizol Corporation | Mixtures of friction modifiers to provide good friction performance to transmission fluids |
WO2017096159A1 (en) | 2015-12-02 | 2017-06-08 | The Lubrizol Corporation | Ultra-low molecular weight amide/ester containing quaternary ammonium salts having short hydrocarbon tails |
WO2017096175A1 (en) | 2015-12-02 | 2017-06-08 | The Lubrizol Corporation | Ultra-low molecular weight imide containing quaternary ammonium salts having short hydrocarbon tails |
WO2017142805A1 (en) | 2016-02-16 | 2017-08-24 | 3M Innovative Properties Company | Polishing systems and methods of making and using same |
WO2018057694A2 (en) | 2016-09-21 | 2018-03-29 | The Lubrizol Corporation | Polyacrylate antifoam components for use in diesel fuels |
WO2019060682A2 (en) | 2017-09-21 | 2019-03-28 | The Lubrizol Corporation | Polyacrylate antifoam components for use in fuels |
WO2019183050A1 (en) | 2018-03-21 | 2019-09-26 | The Lubrizol Corporation | Polyacrylamide antifoam components for use in diesel fuels |
US10556316B2 (en) | 2015-05-13 | 2020-02-11 | 3M Innovative Properties Company | Polishing pads and systems for and methods of using same |
WO2024030591A1 (en) | 2022-08-05 | 2024-02-08 | The Lubrizol Corporation | Processes for producing reaction products including quaternary ammonium salts |
Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3340192A (en) * | 1965-01-06 | 1967-09-05 | Mobil Oil Corp | Lubricating oil compositions containing as a detergent a beta-(alkylamino)alkyl alkenylphenyl ether |
US3360464A (en) * | 1965-08-02 | 1967-12-26 | Mobil Oil Corp | Lubricating oils containing alkylated phenoxy acid derivatives |
US3368972A (en) * | 1965-01-06 | 1968-02-13 | Mobil Oil Corp | High molecular weight mannich bases as engine oil additives |
-
1967
- 1967-04-05 US US628553A patent/US3448047A/en not_active Expired - Lifetime
Patent Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3340192A (en) * | 1965-01-06 | 1967-09-05 | Mobil Oil Corp | Lubricating oil compositions containing as a detergent a beta-(alkylamino)alkyl alkenylphenyl ether |
US3368972A (en) * | 1965-01-06 | 1968-02-13 | Mobil Oil Corp | High molecular weight mannich bases as engine oil additives |
US3360464A (en) * | 1965-08-02 | 1967-12-26 | Mobil Oil Corp | Lubricating oils containing alkylated phenoxy acid derivatives |
Cited By (105)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3725480A (en) * | 1968-11-08 | 1973-04-03 | Standard Oil Co | Ashless oil additives |
US4054422A (en) * | 1975-09-12 | 1977-10-18 | E. I. Du Pont De Nemours & Company | Mannich bases containing tertiary amines and fuel compositions containing said mannich bases |
US4454059A (en) * | 1976-11-12 | 1984-06-12 | The Lubrizol Corporation | Nitrogenous dispersants, lubricants and concentrates containing said nitrogenous dispersants |
US5124055A (en) * | 1988-03-31 | 1992-06-23 | Ethyl Petroleum Additives, Inc. | Lubricating oil composition |
EP0399764A1 (en) | 1989-05-22 | 1990-11-28 | Ethyl Petroleum Additives Limited | Lubricant compositions |
EP0558835A1 (en) | 1992-01-30 | 1993-09-08 | Albemarle Corporation | Biodegradable lubricants and functional fluids |
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 |
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 |
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 |
EP0713908A1 (en) | 1994-11-22 | 1996-05-29 | Ethyl Corporation | Power transmission fluids |
US5814111A (en) * | 1995-03-14 | 1998-09-29 | Shell Oil Company | Gasoline compositions |
US6627584B2 (en) | 2002-01-28 | 2003-09-30 | Ethyl Corporation | Automatic transmission fluid additive comprising reaction product of hydrocarbyl acrylates and dihydrocarbyldithiophosphoric acids |
EP2366762A1 (en) | 2002-10-04 | 2011-09-21 | 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 |
EP2460870A1 (en) | 2002-10-04 | 2012-06-06 | 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 |
US20050065043A1 (en) * | 2003-09-23 | 2005-03-24 | Henly Timothy J. | Power transmission fluids having extended durability |
US20050070446A1 (en) * | 2003-09-25 | 2005-03-31 | Ethyl Petroleum Additives, Inc. | Boron free automotive gear oil |
US20070054813A1 (en) * | 2003-09-25 | 2007-03-08 | Chip Hewette | Boron free automotive gear oil |
US20050101496A1 (en) * | 2003-11-06 | 2005-05-12 | Loper John T. | Hydrocarbyl dispersants and compositions containing the dispersants |
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 |
US20080009426A1 (en) * | 2003-11-10 | 2008-01-10 | Iyer Ramnath N | Lubricant Compositions and Methods Comprising Dispersant and Detergent |
US20050101494A1 (en) * | 2003-11-10 | 2005-05-12 | Iyer Ramnath N. | Lubricant compositions for power transmitting fluids |
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 |
EP2230292A1 (en) | 2003-11-10 | 2010-09-22 | Afton Chemical Corporation | Methods of lubricating transmissions |
US20050143265A1 (en) * | 2003-12-31 | 2005-06-30 | Loper John T. | Hydrocarbyl dispersants including pendant polar functional groups |
US7214649B2 (en) | 2003-12-31 | 2007-05-08 | Afton Chemical Corporation | Hydrocarbyl dispersants including pendant polar functional groups |
US7645728B2 (en) | 2004-02-17 | 2010-01-12 | Afton Chemical Corporation | Lubricant and fuel additives derived from treated amines |
US20050181959A1 (en) * | 2004-02-17 | 2005-08-18 | Esche Carl K.Jr. | Lubricant and fuel additives derived from treated amines |
US7947636B2 (en) | 2004-02-27 | 2011-05-24 | Afton Chemical Corporation | Power transmission fluids |
EP1568759A2 (en) | 2004-02-27 | 2005-08-31 | Afton Chemical Corporation | Power transmission fluids |
US20050202979A1 (en) * | 2004-03-10 | 2005-09-15 | Ethyl Petroleum Additives, Inc. | Power transmission fluids with enhanced extreme pressure characteristics |
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 |
EP1669435A1 (en) | 2004-12-10 | 2006-06-14 | Afton Chemical Corporation | Dispersant reaction product with antioxidant capability |
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 |
US20060264339A1 (en) * | 2005-05-19 | 2006-11-23 | Devlin Mark T | Power transmission fluids with enhanced lifetime characteristics |
US20070111906A1 (en) * | 2005-11-12 | 2007-05-17 | Milner Jeffrey L | Relatively low viscosity transmission fluids |
EP2371933A1 (en) | 2006-02-06 | 2011-10-05 | The Lubrizol Corporation | Tartaric acid derivatives as fuel economy improvers and antiwear agents in crankcase oils and preparation thereof |
US7879775B2 (en) | 2006-07-14 | 2011-02-01 | Afton Chemical Corporation | Lubricant compositions |
US7902133B2 (en) | 2006-07-14 | 2011-03-08 | Afton Chemical Corporation | Lubricant composition |
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 |
US20080015125A1 (en) * | 2006-07-14 | 2008-01-17 | Devlin Mark T | Lubricant compositions |
US20080051305A1 (en) * | 2006-08-28 | 2008-02-28 | Devlin Mark T | Lubricant composition |
US7833953B2 (en) | 2006-08-28 | 2010-11-16 | Afton Chemical Corporation | Lubricant composition |
US20080119377A1 (en) * | 2006-11-22 | 2008-05-22 | Devlin Mark T | Lubricant compositions |
US20100152078A1 (en) * | 2007-05-04 | 2010-06-17 | Ian Macpherson | Environmentally-friendly lubricant compositions |
EP2420553A1 (en) | 2007-05-04 | 2012-02-22 | Afton Chemical Corporation | Environmentally-Friendly Lubricant Compositions |
US20080274921A1 (en) * | 2007-05-04 | 2008-11-06 | Ian Macpherson | Environmentally-Friendly Lubricant Compositions |
EP2017329A1 (en) | 2007-05-04 | 2009-01-21 | Afton Chemical Corporation | Environmentally-Friendly Lubricant Compositions |
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 |
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 |
EP2072611A1 (en) | 2007-12-13 | 2009-06-24 | Afton Chemical Corporation | Lubricant composition suitable for engines fueled by alternate fuels |
US20090156445A1 (en) * | 2007-12-13 | 2009-06-18 | Lam William Y | Lubricant composition suitable for engines fueled by alternate fuels |
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 |
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 |
US20090233822A1 (en) * | 2008-03-11 | 2009-09-17 | Afton Chemical Corporation | Ultra-low sulfur clutch-only transmission fluids |
US20090233823A1 (en) * | 2008-03-11 | 2009-09-17 | Volkswagen Aktiengesellschaft | Method for lubricating a clutch-only automatic transmission component requiring lubrication |
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 |
WO2010096325A1 (en) | 2009-02-18 | 2010-08-26 | The Lubrizol Corporation | Amine derivatives as friction modifiers in lubricants |
WO2011143051A1 (en) | 2010-05-12 | 2011-11-17 | The Lubrizol Corporation | Tartaric acid derivatives in hths fluids |
WO2012033668A1 (en) | 2010-09-07 | 2012-03-15 | The Lubrizol Corporation | Hydroxychroman derivatives as engine oil antioxidants |
EP3070153A1 (en) | 2010-09-07 | 2016-09-21 | The Lubrizol Corporation | Hydroxychroman derivatives as antioxidants |
WO2012141855A1 (en) | 2011-04-15 | 2012-10-18 | R.T. Vanderbilt Company, Inc. | Molybdenum dialkyldithiocarbamate compositions and lubricating compositions containing the same |
WO2012154708A1 (en) | 2011-05-12 | 2012-11-15 | The Lubrizol Corporation | Aromatic imides and esters as lubricant additives |
WO2013013026A1 (en) | 2011-07-21 | 2013-01-24 | The Lubrizol Corporation | Carboxylic pyrrolidinones and methods of use thereof |
WO2013012987A1 (en) | 2011-07-21 | 2013-01-24 | The Lubrizol Corporation | Overbased friction modifiers and methods of use thereof |
WO2013070376A2 (en) | 2011-11-11 | 2013-05-16 | Vanderbilt Chemicals, Llc | Lubricant composition |
WO2014088814A1 (en) | 2012-12-07 | 2014-06-12 | The Lubrizol Corporation | Pyran dispersants |
WO2015047939A1 (en) | 2013-09-25 | 2015-04-02 | 3M Innovative Properties Company | Composite ceramic abrasive polishing solution |
US10293458B2 (en) | 2013-09-25 | 2019-05-21 | 3M Innovative Properties Company | Composite ceramic abrasive polishing solution |
WO2015048011A1 (en) | 2013-09-25 | 2015-04-02 | 3M Innovative Properties Company | Multi-layered polishing pads |
US10071459B2 (en) | 2013-09-25 | 2018-09-11 | 3M Innovative Properties Company | Multi-layered polishing pads |
WO2015184301A2 (en) | 2014-05-30 | 2015-12-03 | The Lubrizol Corporation | Coupled quaternary ammonium salts |
WO2015184251A1 (en) | 2014-05-30 | 2015-12-03 | The Lubrizol Corporation | Branched amine containing quaternary ammonium salts |
WO2015183916A1 (en) | 2014-05-30 | 2015-12-03 | The Lubrizol Corporation | Low molecular weight amide/ester containing quaternary ammonium salts |
WO2015184280A1 (en) | 2014-05-30 | 2015-12-03 | The Lubrizol Corporation | Imidazole containing quaternary ammonium salts |
EP3536766A1 (en) | 2014-05-30 | 2019-09-11 | The Lubrizol Corporation | Epoxide quaternized quaternary ammonium salts |
WO2015184254A1 (en) | 2014-05-30 | 2015-12-03 | The Lubrizol Corporation | High molecular weight amide/ester containing quaternary ammonium salts |
WO2015183908A1 (en) | 2014-05-30 | 2015-12-03 | The Lubrizol Corporation | Low molecular weight imide containing quaternary ammonium salts |
EP3524663A1 (en) | 2014-05-30 | 2019-08-14 | The Lubrizol Corporation | Imidazole containing quaternary ammonium salts |
EP3521404A1 (en) | 2014-05-30 | 2019-08-07 | The Lubrizol Corporation | Low molecular weight imide containing quaternary ammonium salts |
EP3517593A1 (en) | 2014-05-30 | 2019-07-31 | The Lubrizol Corporation | Low molecular weight amide/ester containing quaternary ammonium salts |
EP3514220A1 (en) | 2014-05-30 | 2019-07-24 | The Lubrizol Corporation | Low molecular weight amide/ester containing quaternary ammonium salts |
WO2015184247A1 (en) | 2014-05-30 | 2015-12-03 | The Lubrizol Corporation | High molecular weight imide containing quaternary ammonium salts |
EP3511396A1 (en) | 2014-05-30 | 2019-07-17 | The Lubrizol Corporation | Low molecular weight imide containing quaternary ammonium salts |
WO2015184276A1 (en) | 2014-05-30 | 2015-12-03 | The Lubrizol Corporation | Epoxide quaternized quaternary ammonium salts |
WO2015200592A1 (en) | 2014-06-27 | 2015-12-30 | The Lubrizol Corporation | Mixtures of friction modifiers to provide good friction performance to transmission fluids |
US10556316B2 (en) | 2015-05-13 | 2020-02-11 | 3M Innovative Properties Company | Polishing pads and systems for and methods of using same |
WO2017096175A1 (en) | 2015-12-02 | 2017-06-08 | The Lubrizol Corporation | Ultra-low molecular weight imide containing quaternary ammonium salts having short hydrocarbon tails |
WO2017096159A1 (en) | 2015-12-02 | 2017-06-08 | The Lubrizol Corporation | Ultra-low molecular weight amide/ester containing quaternary ammonium salts having short hydrocarbon tails |
WO2017142805A1 (en) | 2016-02-16 | 2017-08-24 | 3M Innovative Properties Company | Polishing systems and methods of making and using same |
WO2018057694A2 (en) | 2016-09-21 | 2018-03-29 | The Lubrizol Corporation | Polyacrylate antifoam components for use in diesel fuels |
WO2019060682A2 (en) | 2017-09-21 | 2019-03-28 | The Lubrizol Corporation | Polyacrylate antifoam components for use in fuels |
WO2019183050A1 (en) | 2018-03-21 | 2019-09-26 | The Lubrizol Corporation | Polyacrylamide antifoam components for use in diesel fuels |
WO2024030591A1 (en) | 2022-08-05 | 2024-02-08 | The Lubrizol Corporation | Processes for producing reaction products including quaternary ammonium salts |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
US3448047A (en) | Lube oil dispersants | |
US3442808A (en) | Lubricating oil additives | |
US3798165A (en) | Lubricating oils containing high molecular weight mannich condensation products | |
US3697574A (en) | Boron derivatives of high molecular weight mannich condensation products | |
US3539633A (en) | Di-hydroxybenzyl polyamines | |
US3865740A (en) | Multifunctional lubricating oil additive | |
US3493520A (en) | Ashless lubricating oil detergents | |
US2497521A (en) | Oil compositions containing amine salts of boro-diol complexes | |
US3324032A (en) | Reaction product of dithiophosphoric acid and dibasic acid anhydride | |
US3427245A (en) | Lubricant additive composed of a mixture of amine salts of monoamides and monoamides of alkenyl succinic acids | |
FI85159C (en) | Useful reaction product of triaxol and amine phosphate in lubricant | |
US4698169A (en) | Reaction products of alkenylsuccinic compounds with aromatic amines and lubricant compositions thereof | |
US5205945A (en) | Multifunctional additives | |
US3048544A (en) | Lubricant composition | |
US3790496A (en) | Alkylene polyamine polymeric reaction product corrosion inhibitor | |
US3360464A (en) | Lubricating oils containing alkylated phenoxy acid derivatives | |
US2628942A (en) | Lubricating oils containing metal derivatives of cyclic imides | |
US3220949A (en) | Lubricating oil compositions containing iodine and ashless nitrogen-containing oil-soluble derivatives of alkenyl succinic anhydride | |
US3359203A (en) | Ashless dithiophosphoric acid derivatives | |
US4803004A (en) | Reaction products of alkenylsuccinic compounds with aromatic amines and hindered alcohols and lubricant compositions thereof | |
US2849399A (en) | Improved lubricating composition | |
US2394909A (en) | Lubricating oil composition | |
US3846318A (en) | Antioxidant and extreme pressure lubricating oil additive | |
US3554945A (en) | Lubricating compositions containing alkylated polyhydroxy aromatic compounds | |
US4005021A (en) | Oil-soluble reaction products of (a) a high molecular weight olefin polymer, acrylonitrile, chlorine, an amine and maleic anhydride, with (g) an aliphatic amines; and lubricant compositions containing the same |