EP0155131A2 - Grease composition containing boron compound and hydroxy containing soap thickener - Google Patents

Grease composition containing boron compound and hydroxy containing soap thickener Download PDF

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Publication number
EP0155131A2
EP0155131A2 EP85301462A EP85301462A EP0155131A2 EP 0155131 A2 EP0155131 A2 EP 0155131A2 EP 85301462 A EP85301462 A EP 85301462A EP 85301462 A EP85301462 A EP 85301462A EP 0155131 A2 EP0155131 A2 EP 0155131A2
Authority
EP
European Patent Office
Prior art keywords
composition
sulfur
grease
group
carbon atoms
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.)
Granted
Application number
EP85301462A
Other languages
German (de)
French (fr)
Other versions
EP0155131B1 (en
EP0155131A3 (en
Inventor
John Phillips Doner
Andrew Gene Horodysky
John Antone Keller, Jr.
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
ExxonMobil Oil Corp
Original Assignee
Mobil Oil Corp
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Mobil Oil Corp filed Critical Mobil Oil Corp
Priority to AT85301462T priority Critical patent/ATE55406T1/en
Publication of EP0155131A2 publication Critical patent/EP0155131A2/en
Publication of EP0155131A3 publication Critical patent/EP0155131A3/en
Application granted granted Critical
Publication of EP0155131B1 publication Critical patent/EP0155131B1/en
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

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    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M169/00Lubricating compositions characterised by containing as components a mixture of at least two types of ingredient selected from base-materials, thickeners or additives, covered by the preceding groups, each of these compounds being essential
    • C10M169/06Mixtures of thickeners and additives
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    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M117/00Lubricating compositions characterised by the thickener being a non-macromolecular carboxylic acid or salt thereof
    • C10M117/06Lubricating compositions characterised by the thickener being a non-macromolecular carboxylic acid or salt thereof having more than one carboxyl group bound to an acyclic carbon atom or cycloaliphatic carbon atom
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    • C10M133/00Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing nitrogen
    • C10M133/02Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing nitrogen having a carbon chain of less than 30 atoms
    • C10M133/04Amines, e.g. polyalkylene polyamines; Quaternary amines
    • C10M133/06Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to acyclic or cycloaliphatic carbon atoms
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    • C10M133/00Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing nitrogen
    • C10M133/02Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing nitrogen having a carbon chain of less than 30 atoms
    • C10M133/04Amines, e.g. polyalkylene polyamines; Quaternary amines
    • C10M133/06Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to acyclic or cycloaliphatic carbon atoms
    • C10M133/08Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to acyclic or cycloaliphatic carbon atoms containing hydroxy groups
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    • C10M137/00Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing phosphorus
    • C10M137/02Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing phosphorus having no phosphorus-to-carbon bond
    • C10M137/04Phosphate esters
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    • C10M137/00Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing phosphorus
    • C10M137/02Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing phosphorus having no phosphorus-to-carbon bond
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    • C10M137/10Thio derivatives
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    • C10M2207/10Carboxylix acids; Neutral salts thereof
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    • C10M2207/121Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms having hydrocarbon chains of seven or less carbon atoms
    • C10M2207/124Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms having hydrocarbon chains of seven or less carbon atoms containing hydroxy groups; Ethers thereof
    • C10M2207/1245Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms having hydrocarbon chains of seven or less carbon atoms containing hydroxy groups; Ethers thereof used as thickening agent
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    • C10M2207/10Carboxylix acids; Neutral salts thereof
    • C10M2207/12Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms
    • C10M2207/125Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms having hydrocarbon chains of eight up to twenty-nine carbon atoms, i.e. fatty acids
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    • C10M2207/10Carboxylix acids; Neutral salts thereof
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    • C10M2207/18Tall oil acids
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    • C10M2215/00Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2215/02Amines, e.g. polyalkylene polyamines; Quaternary amines
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    • C10M2215/00Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2215/02Amines, e.g. polyalkylene polyamines; Quaternary amines
    • C10M2215/04Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to acyclic or cycloaliphatic carbon atoms
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    • C10M2215/00Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2215/22Heterocyclic nitrogen compounds
    • C10M2215/225Heterocyclic nitrogen compounds the rings containing both nitrogen and oxygen
    • C10M2215/227Phthalocyanines
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Definitions

  • the invention is concerned with a novel group of compositions. It more particularly relates to a synergistic grease composition comprising oil, hydroxy-containing soap thickener and borated amine, and optionally containing phosphorus and sulfur moieties.
  • Greases thickened with metal hydroxystearates, specifically lithium hydroxystearates, are well known, as is the use of "additive packages”. These packages are known to contain phosphorous and sulfur compounds as well as other additives that impart antioxidant, detergent, dispersant, etc. properties to such greases.
  • borated amines such as borated hydrocarbyl mono-and diamines
  • no prior art is known that teaches or suggests the unexpected results obtained by combining the known additive packages mentioned herein with the particular thickener and the borated amines of the invention.
  • an improved grease composition having a high dropping point comprising a major proportion of a grease vehicle and a minor amount of a compound prepared by reacting an amine of the formula wherein x is 0 to 2,
  • R, R 1 , R 3 and R 4 are hydrogen or a C 1 to C 30 hydrocarbyl groups including alkyl groups containing 6 to 20 carbon atoms, hydroxyalkyl groups containing 2 to 4 carbon atoms, polyalkoxylated groups containing 6 to 20 carbon atoms and the corresponding members containing sulfur or additional oxygen, and at least one of R 1 , R 2 , R 3 and R 4 is a hydrocarbyl group, i.e., is not hydrogen, and R 2 is a C 2 to C 4 alkylene group, with a boron compound which may be boric acid, boric oxide, a metaborate, a similar boron source or an alkyl borate of the formula: wherein y is 1 to 3, z is 0 to 2, their
  • the alkyl borates include the mono-, di- and trialkyl borates, i.e., those having the methyl, ethyl, propyl, butyl, pentyl and hexyl groups.
  • the amine is overborated.
  • overborated is meant the presence in the borated product of more than a stoichiometric amount of boron with respect to the amine.
  • the borated amines of the invention can be made by reacting an amine of the above formula with a boron compound such as boric oxide, boric acid, an alkyl borate or mixtures of these.
  • a boron compound such as boric oxide, boric acid, an alkyl borate or mixtures of these.
  • the resulting products are believed to be, primarily, borated amines, but other possible products present are metaborates and the like.
  • the primary amines such as hexylamine, octylamine, nonylamine, decylamine, dodecylamine, tetradecylamine, octadecylamine, eicosylamine, triacontylamine, oleylamine, stearylamine, isostearylamine, tallowamine and soyamine
  • the secondary amines corresponding to (1) having both groups the same or having mixtures of such groups
  • the corresponding tertiary amines where again all the groups in the same molecule can be the same or different
  • diamines such as N-octyl-l,2-ethylenediamine or the N-octyl-1,3-propylenediamine, N-coco-l,2-ethylenediamine or the N-coco-1,3-propylenediamine, N-oleyl-1,2-ethylened
  • Alkoxylated amines included are bis(2-hydroxyethyl) oleylamine, bis(2-hydroxypropyl)oleylamine, bis(2-hydroxyethyl) tallowamine, bis(2-hydroxypropyl)tallowamine, (hydroxyethyl)-(hydroxypropyl)tallowamine, polyethoxylated oleylamine (containing 7 ethoxyl groups) and polyethoxylated tallowamine (containing 3 ethoxyl groups). Included also are hydroxyalkyl amines made by the ethoxylation or propoxylation of hydrocarbyldiamines or hydrocarbyltriamines.
  • aromatic and alkyl- or alkylene-substituted aromatic groups containing 6 to 30 carbon atoms are included.
  • alkoxyalkylamines such as dodecyloxypropylamine and triisodecyloxypropylamine and similar oxygen- containing amines, and the corresponding alkoxydiamines, such as the N-alkoxyhydrocarbylenediamines.
  • the reaction to form the borated amine or borate ester can be carried out at from about 80°C to about 260°C, preferably from about 110°C to about 180°C.
  • the temperature chosen will depend for the most part on the particular reactants and on whether or not a solvent is used.
  • Reaction pressures can be vacuum, atmospheric or positive pressure.
  • quantities of reactants be chosen such that the molar ratio of amine to boron compound be from about 0.2 to about 2, preferably from about 0.5 to about 0.9.
  • the amine can be reacted with an excess of the borating species to form a borate amine containing from about 0.1X by weight of boron to as much as 10% or more of boron.
  • reaction can be advantageously run at from about 1 to about 5 atmospheres.
  • a solvent may be used.
  • any relatively non-polar, unreactive solvent can be used, including benzene, toluene, xylene and 1,4-dioxane.
  • Other hydrocarbon and alcoholic solvents which include propanol, butanol, hexamethylene glycol and the like, can be used. Mixtures of alcoholic and hydrocarbon solvents can also be used.
  • any phase of the process can be carried out in from about 1 to about 20 hours.
  • a narrow class of thickening agents is preferred to make the grease of this invention. Included among the preferred thickening agents are those containing at least a portion of alkali metal, alkaline earth metal or amine soaps of hydroxyl-containing fatty acids, fatty glycerides and fatty esters having from 12 to about 30 carbon atoms per molecule.
  • the metals are typified by sodium, lithium, calcium and barium. Preferred is lithium.
  • Preferred members among these acids and fatty materials are 12-hydroxystearic acid and glycerides and esters containing 12-hydroxystearates, 14-hydroxystearic acid, 16-hydroxystearic acid and 6-hydroxystearic acid.
  • thickener need not be derived from the aforementioned preferred members. Significant benefit can be attained using as little thereof as about 15% by weight of the total thickener.
  • a complementary amount, i.e., up to about 85% by weight of a wide variety of thickening agents can be used in the grease of this invention. Included among the other useful thickening agents are alkali and alkaline earth metal soaps of methyl-12-hydroxystearate, diesters of a C 4 to C 12 dicarboxylic acid and tall oil or marine oil fatty acids. Other alkali or alkaline earth metal fatty acids containing from 12 to 30 carbon atoms and no free hydroxyl may be used. These include soaps of stearic and oleic acids.
  • thickening agents include salt and salt-soap complexes as calcium stearate-acetate (U.S. Patent No. 2,197,263), barium stearate acetate (U.S. Patent No. 2,564,561), calcium, stearate-caprylate-acetate complexes (U.S. Patent No. 2,999,065), calcium caprylate-acetate (U.S. Patent No. 2,999,066), and calcium salts and soaps of low-, intermediate- and high-molecular weight acids and of nut oil acids.
  • thickening agents comprises substituted ureas, phthalocyamines, indanthrene, pigments such as perylimides, pyromellitdiimides, and ammeline, as well as certain hydrophobic clays.
  • These thickening agents can be prepared from clays which are initially hydrophilic in character, but which have been converted into a hydrophobic condition by the introduction of long-chain hydrocarbon radicals into the surface of the clay particles prior to their use as a component of a grease composition, as, for example, by being subjected to a preliminary treatment with an organic cationic surface active agent, such as an onium compound.
  • Typical onium compounds are tetraalkylammonium chlorides, such as dimethyl dioctadecyl ammonium chloride, dimethyl dibenzyl ammonium chloride and mixtures thereof. This method of conversion, being well known to those skilled in the art, is believed to require no further discussion, and does not form a part of the present invention.
  • Manufacture of the thickening agents can be done in a variety of grease making equipment such as in open kettles at reduced, atmospheric, or positive pressures; in higher pressure reaction chambers which may be operated to as high as 180 psig; or in continuous manufacturing equipment.
  • the temperature range from the bulk grease under manufacture can range from 15°C (60°F) to 238°C (460°F).
  • the third member(s) that may be present in the grease composition are the phosphorus and sulfur moieties. Both of these can be present in the same molecule, such as in a metal or non-metal phosphorodithioate of the formula wherein R6is a hydrocarbyl group containing 3 to 18 carbon atoms, M is a metal or non-metal, n is the valence of M and Z is oxygen or sulfur, at least one Z being sulfur.
  • R6 is preferably an alkyl group and may be a propyl, butyl; pentyl, hexyl, octyl, decyl, dodecyl, tetradecyl or octadecyl group, including those derived from propanol, isopropanol, butanol, isobutanol, sec-butanol, 4-methyl-2-pentanol, 2-ethylhexanol, oleyl alcohol, and mixtures thereof.
  • alkaryl groups such as butylphenyl, octylphenyl, nonylphenyl and dodecylphenyl groups.
  • the metals covered by M include those in Groups IA, IIA, IIB and VIII of the Periodic Table. Some that may be mentioned are lithium, molybdenum, sodium, calcium, zinc, cadmium, silver and gold.
  • Non-metallic ions include organic groups derived from vinyl esters such as vinyl acetate, vinyl ethers such as butyl vinyl ether, epoxides such as propylene oxide and 1,2-epoxydodecane and amine salts. They also include other nitrogenous compounds such as those derived from hydrocarbyl amines and diamines, including oleylamine and N-oleyl-l,3-propylenediamine and such as the imidazolines and oxazolines.
  • the phosphorus and sulfur can also be supplied from the combination of two separate compounds, such as the combination of (1) a dihydrocarbyl phosphite having 2 to 10 carbon atoms in each hydrocarbyl group or mixtures of phosphites and (2) a sulfide such as sulfurized isobutylene, dibenzyl disulfide, sulfurized terpenes, phosphorodithionyl disulfide and sulfurized jojoba oil.
  • the phosphites embrace the dibutyl, dihexyl, dioctyl, didecyl and similar phosphites.
  • Phosphate esters containing 4 to 20 carbon atoms in each hydrocarbyl group such as tributyl phosphate, tridecyl phosphate, tricresyl phosphate and mixtures of such phosphates, can also be used.
  • the broad invention is to a grease composition comprising the two components mentioned.
  • reaction products of the present invention may be employed in any amount which is effective for imparting the desired degree of friction reduction, antiwear activity, antioxidant activity, high temperature stability or antirust activity.
  • the borated amine and the phosphorus- and/or sulfur-containing compound(s) are effectively employed in combined amounts of from about 0.02% to about 20% by weight, and preferably from about 0.2% to about 4% of the total weight of the composition.
  • the greases of the present invention can be made from either a mineral oil or a synthetic oil, or mixtures thereof.
  • mineral oils both paraffinic, naphthenic and mixtures thereof, may be of any suitable lubricating viscosity range, as for example, from about 45 SSU at 100°F to about 6000 SSU at 100°F, and preferably from about 50 to about 250 SSU at 210°F.
  • These oils may have viscosity indexes ranging up to about 100 or higher. Viscosity indexes from about 70 to about 95 are preferred.
  • the average molecular weights of these oils may range from about 250 to about 800.
  • the lubricating oil from which it is prepared is generally employed in an amount sufficient to balance the total grease composition, after accounting for the desired quantity of the thickening agent, and other additive components to be included in the grease formulation.
  • Typical synthetic vehicles include polyisobutylene, polybutenes, hydrogenated polydecenes, polypropylene glycol, polyethylene glycol, trimethylol propane esters, neopentyl and pentaerythritol esters, di(2-ethylhexyl) sebacate, di(2-ethylhexyl) adipate, dibutyl phthalate, fluorocarbons, silicate esters, silanes, esters of phosphorus-containing acids, liquid ureas, ferrocene derivatives, hydrogenated synthetic oils, chain-type polyphenyls, siloxanes and silicones (polysiloxanes), alkyl-substituted diphenyl ethers typified by a butyl-substituted bis(p-phenoxy phenyl) ether, phenoxy phenylethers.
  • the metallic soap grease compositions containing one or more of the borated amines, and optionally, one or more of the sulfur and phosphorus combinations described herein provide advantages in increased dropping point, improved grease consistency properties, antirust characteristics and potential antifatigue, antiwear and antioxidant benefits unavailable in prior greases.
  • the grease of this invention is unique in that it can be preferably manufactured by the admixture of additive quantities of the alcohol borates to the fully formed soap grease after completion of saponification.
  • a mixture of 1295 g N-oleyl-l,3-propylenediamine (obtained as Duomeen 0 from Armak Chemical Co.), 218 g of xylene, 437 g of n-butanol, 658 g of hexamethylene glycol and 1210 g of boric acid were placed in a reactor equipped with heater, agitator and Dean-Stark tube with condenser, and refluxed for about 10 hours until all water formed in the reaction azeotroped over (maximum temperature was about 195°C).
  • the solvents were removed by vacuum distillation at 195°C and the product was filtered and then diluted with an equal amount of 100 second process oil to form a 50% concentrate of borated diamine in mineral oil.
  • the concentrate was an orange colored viscous liquid.
  • N-tallow-1,3-propylenediamine obtained as Duomeen T from Armak Chemical Co.
  • boric acid as generally described in Example 1.
  • the borated N-tallow-l,3-propylenediamine was blended with an equal wt. of 100 second process oil to form a 50% concentrate in mineral oil.
  • a lithium hydroxystearate grease thickener was prepared by saponification of a mixture containing 12-hydroxystearic acid (8%) and the glyceride thereof (9%) with lithium hydroxide in a mineral oil vehicle at about 177°C in a closed contactor.
  • a typical grease additive package consisting of an amine antioxidant, phenolic antioxidant, metallic dithiophosphate (1.5 wt% of zinc dialkyl phosphorodithioate, where the alkyl is derived from a mixture of C 3 to C 6 primary alcohols), sulfur-containing metal deactivator and nitrogen containing antirust additives, was added.
  • Example 4 To the base grease of Example 4, was added at about 110°C, 0.5 wt% of the borated N-oleyl-1,3-propylenediamine of Example 1.
  • Example 4 To the base grease of Example 4 was added, at about 115°C, 1.0 wt% of the borated N-tallow-1,3-propylenediamine of Example 2.
  • Example 3 To the base grease of Example 3 was added 0.5 wt. % of the borated N-oleyl-1,3-propylenediamine of Example 1.
  • Example 4 50 wt. % of the base grease used in Example 4 plus 50 wt. % of the grease of Example 9, producing a 50-50 mixture of hydroxy- and non-hydroxy-containing thickeners.
  • Examples 5 and 6 show a significant effect upon dropping point improvement when borated amine is added to hydroxy-containing carboxylate soap thickened grease in the presence of a phosphorus and sulfur source.
  • Examples 7 and 8 show a significant effect upon hydroxy-containing carboxylate soap thickened grease when the borated amines described are used.

Abstract

Grease compositions, wherein the grease is thickened with a metal hydroxy-containing soap grease thickener are provided. Other ingredients of the compositions include borated hydrocarbylamines and phosphorus and sulfur moieties.

Description

  • The invention is concerned with a novel group of compositions. It more particularly relates to a synergistic grease composition comprising oil, hydroxy-containing soap thickener and borated amine, and optionally containing phosphorus and sulfur moieties.
  • Greases thickened with metal hydroxystearates, specifically lithium hydroxystearates, are well known, as is the use of "additive packages". These packages are known to contain phosphorous and sulfur compounds as well as other additives that impart antioxidant, detergent, dispersant, etc. properties to such greases.
  • From U.S. 4,328,113 it is also known that borated amines, such as borated hydrocarbyl mono-and diamines, are useful as friction reducers in lubricants, especially in lubricating oils. However, no prior art is known that teaches or suggests the unexpected results obtained by combining the known additive packages mentioned herein with the particular thickener and the borated amines of the invention.
  • In accordance with the invention, there is provided an improved grease composition having a high dropping point comprising a major proportion of a grease vehicle and a minor amount of a compound prepared by reacting an amine of the formula
    Figure imgb0001
    wherein x is 0 to 2, R, R1, R3 and R4 are hydrogen or a C1 to C30 hydrocarbyl groups including alkyl groups containing 6 to 20 carbon atoms, hydroxyalkyl groups containing 2 to 4 carbon atoms, polyalkoxylated groups containing 6 to 20 carbon atoms and the corresponding members containing sulfur or additional oxygen, and at least one of R1 , R2 , R3 and R4 is a hydrocarbyl group, i.e., is not hydrogen, and R 2 is a C2 to C4 alkylene group, with a boron compound which may be boric acid, boric oxide, a metaborate, a similar boron source or an alkyl borate of the formula:
    Figure imgb0002
    wherein y is 1 to 3, z is 0 to 2, their sum being 3, and R is an alkyl group containing from 1 to 6 carbon atoms, the improvement comprising thickening said grease with a hydroxy-containing soap thickener. The presence of phosphorus and sulfur moieties provides an even higher dropping point. The alkyl borates include the mono-, di- and trialkyl borates, i.e., those having the methyl, ethyl, propyl, butyl, pentyl and hexyl groups.
  • Preferably the amine is overborated. By "overborated" is meant the presence in the borated product of more than a stoichiometric amount of boron with respect to the amine.
  • The borated amines of the invention can be made by reacting an amine of the above formula with a boron compound such as boric oxide, boric acid, an alkyl borate or mixtures of these. The resulting products are believed to be, primarily, borated amines, but other possible products present are metaborates and the like. Included within the scope of the amines as set forth in the above formula are (1) the primary amines such as hexylamine, octylamine, nonylamine, decylamine, dodecylamine, tetradecylamine, octadecylamine, eicosylamine, triacontylamine, oleylamine, stearylamine, isostearylamine, tallowamine and soyamine, (2) the secondary amines corresponding to (1) having both groups the same or having mixtures of such groups, (3) the corresponding tertiary amines where again all the groups in the same molecule can be the same or different and (4) diamines such as N-octyl-l,2-ethylenediamine or the N-octyl-1,3-propylenediamine, N-coco-l,2-ethylenediamine or the N-coco-1,3-propylenediamine, N-oleyl-1,2-ethylenediamine, or N-oley1-1,3-propylenediamine, N-soya-1,2-ethylenediamine or the N-soya-1,3-propylenediamine and N-tallow-l,2-ethylenediamine or the N-tallow-l,3-propylenediamine. The secondary amines include N-ethyl-N-oleylamine, N-methyl-N-soyamine, and the tertiary amines include N,N-diethyl-N-oleylamine.
  • Alkoxylated amines included are bis(2-hydroxyethyl) oleylamine, bis(2-hydroxypropyl)oleylamine, bis(2-hydroxyethyl) tallowamine, bis(2-hydroxypropyl)tallowamine, (hydroxyethyl)-(hydroxypropyl)tallowamine, polyethoxylated oleylamine (containing 7 ethoxyl groups) and polyethoxylated tallowamine (containing 3 ethoxyl groups). Included also are hydroxyalkyl amines made by the ethoxylation or propoxylation of hydrocarbyldiamines or hydrocarbyltriamines. Specifically included are aromatic and alkyl- or alkylene-substituted aromatic groups containing 6 to 30 carbon atoms. Further included are alkoxyalkylamines, such as dodecyloxypropylamine and triisodecyloxypropylamine and similar oxygen- containing amines, and the corresponding alkoxydiamines, such as the N-alkoxyhydrocarbylenediamines.
  • The reaction to form the borated amine or borate ester can be carried out at from about 80°C to about 260°C, preferably from about 110°C to about 180°C. The temperature chosen will depend for the most part on the particular reactants and on whether or not a solvent is used. Reaction pressures can be vacuum, atmospheric or positive pressure. In carrying out this reaction, it is preferable that quantities of reactants be chosen such that the molar ratio of amine to boron compound be from about 0.2 to about 2, preferably from about 0.5 to about 0.9. The amine can be reacted with an excess of the borating species to form a borate amine containing from about 0.1X by weight of boron to as much as 10% or more of boron.
  • While atmospheric pressure is generally preferred, the reaction can be advantageously run at from about 1 to about 5 atmospheres. Furthermore, where conditions warrant it, a solvent may be used. In general, any relatively non-polar, unreactive solvent can be used, including benzene, toluene, xylene and 1,4-dioxane. Other hydrocarbon and alcoholic solvents, which include propanol, butanol, hexamethylene glycol and the like, can be used. Mixtures of alcoholic and hydrocarbon solvents can also be used.
  • The times for the reactions are not critical. Thus, any phase of the process can be carried out in from about 1 to about 20 hours.
  • A narrow class of thickening agents is preferred to make the grease of this invention. Included among the preferred thickening agents are those containing at least a portion of alkali metal, alkaline earth metal or amine soaps of hydroxyl-containing fatty acids, fatty glycerides and fatty esters having from 12 to about 30 carbon atoms per molecule. The metals are typified by sodium, lithium, calcium and barium. Preferred is lithium. Preferred members among these acids and fatty materials are 12-hydroxystearic acid and glycerides and esters containing 12-hydroxystearates, 14-hydroxystearic acid, 16-hydroxystearic acid and 6-hydroxystearic acid.
  • The entire amount of thickener need not be derived from the aforementioned preferred members. Significant benefit can be attained using as little thereof as about 15% by weight of the total thickener. A complementary amount, i.e., up to about 85% by weight of a wide variety of thickening agents can be used in the grease of this invention. Included among the other useful thickening agents are alkali and alkaline earth metal soaps of methyl-12-hydroxystearate, diesters of a C4 to C12 dicarboxylic acid and tall oil or marine oil fatty acids. Other alkali or alkaline earth metal fatty acids containing from 12 to 30 carbon atoms and no free hydroxyl may be used. These include soaps of stearic and oleic acids.
  • Other thickening agents include salt and salt-soap complexes as calcium stearate-acetate (U.S. Patent No. 2,197,263), barium stearate acetate (U.S. Patent No. 2,564,561), calcium, stearate-caprylate-acetate complexes (U.S. Patent No. 2,999,065), calcium caprylate-acetate (U.S. Patent No. 2,999,066), and calcium salts and soaps of low-, intermediate- and high-molecular weight acids and of nut oil acids.
  • Another group of thickening agents comprises substituted ureas, phthalocyamines, indanthrene, pigments such as perylimides, pyromellitdiimides, and ammeline, as well as certain hydrophobic clays. These thickening agents can be prepared from clays which are initially hydrophilic in character, but which have been converted into a hydrophobic condition by the introduction of long-chain hydrocarbon radicals into the surface of the clay particles prior to their use as a component of a grease composition, as, for example, by being subjected to a preliminary treatment with an organic cationic surface active agent, such as an onium compound. Typical onium compounds are tetraalkylammonium chlorides, such as dimethyl dioctadecyl ammonium chloride, dimethyl dibenzyl ammonium chloride and mixtures thereof. This method of conversion, being well known to those skilled in the art, is believed to require no further discussion, and does not form a part of the present invention.
  • Manufacture of the thickening agents can be done in a variety of grease making equipment such as in open kettles at reduced, atmospheric, or positive pressures; in higher pressure reaction chambers which may be operated to as high as 180 psig; or in continuous manufacturing equipment. The temperature range from the bulk grease under manufacture can range from 15°C (60°F) to 238°C (460°F).
  • The third member(s) that may be present in the grease composition are the phosphorus and sulfur moieties. Both of these can be present in the same molecule, such as in a metal or non-metal phosphorodithioate of the formula
    Figure imgb0003
    wherein R6is a hydrocarbyl group containing 3 to 18 carbon atoms, M is a metal or non-metal, n is the valence of M and Z is oxygen or sulfur, at least one Z being sulfur.
  • In this compound, R6is preferably an alkyl group and may be a propyl, butyl; pentyl, hexyl, octyl, decyl, dodecyl, tetradecyl or octadecyl group, including those derived from propanol, isopropanol, butanol, isobutanol, sec-butanol, 4-methyl-2-pentanol, 2-ethylhexanol, oleyl alcohol, and mixtures thereof. Further included are alkaryl groups such as butylphenyl, octylphenyl, nonylphenyl and dodecylphenyl groups.
  • The metals covered by M include those in Groups IA, IIA, IIB and VIII of the Periodic Table. Some that may be mentioned are lithium, molybdenum, sodium, calcium, zinc, cadmium, silver and gold. Non-metallic ions include organic groups derived from vinyl esters such as vinyl acetate, vinyl ethers such as butyl vinyl ether, epoxides such as propylene oxide and 1,2-epoxydodecane and amine salts. They also include other nitrogenous compounds such as those derived from hydrocarbyl amines and diamines, including oleylamine and N-oleyl-l,3-propylenediamine and such as the imidazolines and oxazolines.
  • The phosphorus and sulfur can also be supplied from the combination of two separate compounds, such as the combination of (1) a dihydrocarbyl phosphite having 2 to 10 carbon atoms in each hydrocarbyl group or mixtures of phosphites and (2) a sulfide such as sulfurized isobutylene, dibenzyl disulfide, sulfurized terpenes, phosphorodithionyl disulfide and sulfurized jojoba oil. The phosphites embrace the dibutyl, dihexyl, dioctyl, didecyl and similar phosphites. Phosphate esters containing 4 to 20 carbon atoms in each hydrocarbyl group, such as tributyl phosphate, tridecyl phosphate, tricresyl phosphate and mixtures of such phosphates, can also be used.
  • In summary, it is essential to the practice of this invention, in which greases having vastly improved dropping points are obtained, that at least the first two of the above-mentioned ingredients be formulated into the composition. Thus:
    • first, with respect to the preparation of the grease, the thickener will have at least about 15% by weight of a metal or non-metal hydroxy-containing soap therein, the total thickener being from about 3% to about 20% by weight of the total grease composition;
    • second, there will be added to the grease from about 0.01% to about 10% by weight, preferably about 0.1% to about 2%, of the borated amine, in which an amine preferably has been reacted with at least an equimolar amount of a boron compound; and
    • as an optional third component, the composition may have therein from 0.01% to about 10% by weight preferably, from 0.2% to 2% by weight of phosphorus- and sulfur-containing compounds or a mixture of two or more compounds which separately supply the phosphorus and sulfur moieties. If separate compounds are used, an amount of the mixture equivalent to the above concentration levels is used to supply desired amounts of phosphorus and sulfur.
  • It was noted that, when the hydroxy-containing thickener was used with the borated amine, the dropping point of the grease was consistently unexpectedly higher than a grease from the same grease vehicle and the same borated amine, but with a different thickener, e.g., a non-hydroxy-containing thickener. Thus, the broad invention is to a grease composition comprising the two components mentioned.
  • In general, the reaction products of the present invention may be employed in any amount which is effective for imparting the desired degree of friction reduction, antiwear activity, antioxidant activity, high temperature stability or antirust activity. In many applications, however, the borated amine and the phosphorus- and/or sulfur-containing compound(s) are effectively employed in combined amounts of from about 0.02% to about 20% by weight, and preferably from about 0.2% to about 4% of the total weight of the composition.
  • The greases of the present invention can be made from either a mineral oil or a synthetic oil, or mixtures thereof. In general, mineral oils, both paraffinic, naphthenic and mixtures thereof, may be of any suitable lubricating viscosity range, as for example, from about 45 SSU at 100°F to about 6000 SSU at 100°F, and preferably from about 50 to about 250 SSU at 210°F. These oils may have viscosity indexes ranging up to about 100 or higher. Viscosity indexes from about 70 to about 95 are preferred. The average molecular weights of these oils may range from about 250 to about 800. In making the grease, the lubricating oil from which it is prepared is generally employed in an amount sufficient to balance the total grease composition, after accounting for the desired quantity of the thickening agent, and other additive components to be included in the grease formulation.
  • In instances where synthetic oils are desired, in preference to mineral oils, various compounds of this type may be successfully utilized. Typical synthetic vehicles include polyisobutylene, polybutenes, hydrogenated polydecenes, polypropylene glycol, polyethylene glycol, trimethylol propane esters, neopentyl and pentaerythritol esters, di(2-ethylhexyl) sebacate, di(2-ethylhexyl) adipate, dibutyl phthalate, fluorocarbons, silicate esters, silanes, esters of phosphorus-containing acids, liquid ureas, ferrocene derivatives, hydrogenated synthetic oils, chain-type polyphenyls, siloxanes and silicones (polysiloxanes), alkyl-substituted diphenyl ethers typified by a butyl-substituted bis(p-phenoxy phenyl) ether, phenoxy phenylethers.
  • The metallic soap grease compositions containing one or more of the borated amines, and optionally, one or more of the sulfur and phosphorus combinations described herein provide advantages in increased dropping point, improved grease consistency properties, antirust characteristics and potential antifatigue, antiwear and antioxidant benefits unavailable in prior greases. The grease of this invention is unique in that it can be preferably manufactured by the admixture of additive quantities of the alcohol borates to the fully formed soap grease after completion of saponification.
  • The following Examples will present illustrations of the invention. They are illustrative only, and are not meant to limit the invention.
  • EXAMPLE 1
  • A mixture of 1295 g N-oleyl-l,3-propylenediamine (obtained as Duomeen 0 from Armak Chemical Co.), 218 g of xylene, 437 g of n-butanol, 658 g of hexamethylene glycol and 1210 g of boric acid were placed in a reactor equipped with heater, agitator and Dean-Stark tube with condenser, and refluxed for about 10 hours until all water formed in the reaction azeotroped over (maximum temperature was about 195°C). The solvents were removed by vacuum distillation at 195°C and the product was filtered and then diluted with an equal amount of 100 second process oil to form a 50% concentrate of borated diamine in mineral oil. The concentrate was an orange colored viscous liquid.
  • EXAMPLE 2
  • N-tallow-1,3-propylenediamine (obtained as Duomeen T from Armak Chemical Co.) was borated with boric acid as generally described in Example 1. For convenience of handling, the borated N-tallow-l,3-propylenediamine was blended with an equal wt. of 100 second process oil to form a 50% concentrate in mineral oil.
  • EXAMPLE 3
  • A lithium hydroxystearate grease thickener was prepared by saponification of a mixture containing 12-hydroxystearic acid (8%) and the glyceride thereof (9%) with lithium hydroxide in a mineral oil vehicle at about 177°C in a closed contactor.
  • EXAMPLE 4
  • After depressuring and dehydration of the thickener in an open kettle, sufficient mineral oil was added to reduce the thickener content to about 9.0%. After cooling to about 99°C, a typical grease additive package, consisting of an amine antioxidant, phenolic antioxidant, metallic dithiophosphate (1.5 wt% of zinc dialkyl phosphorodithioate, where the alkyl is derived from a mixture of C3 to C6 primary alcohols), sulfur-containing metal deactivator and nitrogen containing antirust additives, was added.
  • EXAMPLE 5
  • To the base grease of Example 4, was added at about 110°C, 0.5 wt% of the borated N-oleyl-1,3-propylenediamine of Example 1.
  • EXAMPLE 6
  • To the base grease of Example 4 was added, at about 115°C, 1.0 wt% of the borated N-tallow-1,3-propylenediamine of Example 2.
  • EXAMPLE 7
  • To the base grease of Example 3 was added 0.5 wt. % of the borated N-oleyl-1,3-propylenediamine of Example 1.
  • EXAMPLE 8
  • Same as Example 7, except 2% of borated amine was used.
  • EXAMPLE 9
  • Base grease thickened with the lithium soap of 50/50 (wt) mixture of stearic and palmitic acids, which are non-hydroxy-containing thickeners.
  • EXAMPLE 10
  • 50 wt. % of the base grease used in Example 4 plus 50 wt. % of the grease of Example 9, producing a 50-50 mixture of hydroxy- and non-hydroxy-containing thickeners.
  • EXAMPLE 11
  • Base grease of Example 9 containing 2 wt. % of the borated amine of Example 2.
  • Results obtained in the ASTM D2265-78 grease dropping point test are shown in the following table.
    Figure imgb0004
  • Examples 5 and 6 show a significant effect upon dropping point improvement when borated amine is added to hydroxy-containing carboxylate soap thickened grease in the presence of a phosphorus and sulfur source.
  • Examples 7 and 8 show a significant effect upon hydroxy-containing carboxylate soap thickened grease when the borated amines described are used.
  • Examples 9, 10 and 11 clearly show no benefit of the borated amine upon the dropping point of a non-hydroxy-containing carboxylate soap thickened grease.

Claims (28)

1. An improved grease composition comprising a major proportion of a grease vehicle and from about 0.01% to about 10% by weight of a reaction product made by reacting an amine of the formula
Figure imgb0005
wherein x is 0 to 2, R, R1, R3 and R4 are hydrogen or hydrocarbyl groups containing from 1 to 30 carbon atoms, hydroxyalkyl groups containing 2 to 4 carbon atoms, a polyalkoxylated group containing 6 to 20 carbon'atoms or the latter group containing sulfur or additional oxygen, at least one of R, R1, R3 and R4 being a non-hydrogen group and R2 is a C2 to C4 alkylene group, with a boron compound, the improvement comprising thickening said grease with a thickener containing at least about 15% by weight of a hydroxy-containing soap thickener.
2. The composition of claim 1 additionally containing from about 0.01% to about 10% by weight of a compound containing both phosphorus and sulfur or a mixture of phosphorus-containing and sulfur-containing compounds to supply an equivalent amount of phosphorus and sulfur.
3. The composition of Claim 1 wherein the thickener is an alkali metal, alkaline earth metal or amine soap of a hydroxyl-containing fatty acid, fatty glyceride or fatty ester containing 12 to 30 carbon atoms.
4. The composition of Claim 3 wherein the metal is sodium, lithium, calcium or barium.
5. The composition of Claim 3 wherein the thickener is derived from 12-hydroxystearic acid, 14-hydroxystearic acid, 16-hydroxystearic acid, 6-hydroxystearic acid or the glyceride or ester thereof.
6. The composition of Claim 1 wherein R, R 1, R 3 and R 4 are hydrogen or alkyl groups containing 6 to 20 carbon atoms, at least one of which is not hydrogen.
7. The composition of Claim 1 wherein the amine is (1) hexylamine, octylamine, nonylamine, decylamine, dodecylamine, tetradecylamine, octadecylamine, eicosylamine, triacontylamine, oleylamine, stearylamine, isostearylamine, tallowamine, soyamine, (2) the secondary amines corresponding to (I) having both groups the same or having mixtures of such groups, (3) the corresponding tertiary amines wherein all the groups in each molecule are the same or different, or (4) N-octyl-1,2-ethylenediamine, N-octyl-1,3-propylenediamine, N-coco-1,2-ethylenediamine, N-coco-1,3-propylenediamine, N-oleyl-1,2-ethylenediamine, N-oleyl-1,3-propylenediamine, N-soya-1,2-ethylenediamine, N-soya-1,3-propylenediamine, N-tallow-1,2-ethylenediamine, N-tallow-1,3-propylenediamine, N-ethyl-N-oleylamine, N-methyl-N-soyamine, N,N-diethyl-N-oleylamine, bis(2-hydroxyethyl)oleylamine, bis(2-hydroxypropyl)oleylamine, bis(2-hydroxyethyl)tallowamine, bis(2-hydroxypropyl)-tallowamine, (hydroxyethyl)(hydroxypropyl)tallowamine, polyethoxylatedoleylamine containing 7 ethoxy groups, polyethoxylated tallowamine containing 3 ethoxyl groups, hydroxyalkyl amines made by the ethoxylation or propoxylation of hydrocarbyldiamines or hydrocarbyltriamines, dodecyloxypropylamine or triisodecyloxypropylamine.
8. The composition of Claim 1 wherein the boron compound is selected from the group consisting of boric acid, boric oxide, a metaborate or a mono-, di- and trimethyl borate, mono-, di- and triethyl borate, mono-, di and tripropyl borate, mono-, di- and tributyl borate, mono-, di- and tripentyl borate and mono-, di- and trihexyl borate.
9. The composition of Claim 8 wherein the boron compound is boric acid.
10. The composition of Claim 1 wherein the phosphorus and sulfur moieties are supplied by a phosphorothioate of the formula
Figure imgb0006
wherein R6 is a hydrocarbyl group containing 3 to 18 carbon atoms, M is a metal or non-metal, n is the valence of M and Z is oxygen or sulfur, at least one Z being sulfur.
11. The composition of Claim 10 wherein R is an alkyl group or an alkaryl group.
12. The composition of Claim 11 wherein R is a propyl, butyl, pentyl, hexyl, octyl, dodecyl, tetradecyl, octadecyl, butylphenyl, octylphenyl, nonylphenyl, dodecylphenyl or oleyl group or a mixture thereof.
13. The composition of Claim 12 wherein R is derived from propanol, isopropanol, butanol, isobutanol, sec-butanol, 4-methyl-2-pentanol, 2-ethylhexanol or a mixture thereof.
14. The compositon of Claim 10 wherein M is a metal from Group IA, IIA, IIB or VIII of the Periodic Table.
15. The composition of Claim 14 wherein the metal is lithium, sodium, silver, molybdenum, calcium, zinc, cadmium or gold.
16. The composition of Claim 10 wherein M is derived from vinyl acetate, butyl vinyl ether, propylene oxide, 1,2-epoxydodecane or nitrogenous compound.
17. The composition of Claim 1 wherein the phosphorus and sulfur moieties are supplied by a combination of (1) a dihydrocarbyl phosphite having 2 to 6 carbon atoms in each hydrocarbyl group, mixtures of such phosphites, or a phosphate ester having 4 to 20 carbon atoms in each hydrocarbyl group and (2) a sulfide selected from sulfurized isobutylene, dibenzyl disulfide, sulfurized terpenes, phosphorodithionyl disulfide and sulfurized jojoba oil.
18. The composition of Claim 17 wherein the phosphite is a dibutyl, dihexyl, dioctyl or didecyl phosphite or mixtures thereof.
19. The composition of Claim 17 wherein the phosphate ester is a tributyl, tridecyl or tricresyl phosphate or mixtures thereof.
20. The composition of Claim 1 wherein the amine is N-oleyl-1,3-propylenediamine, the boron compound is boric acid, the thickener is 12-hydroxystearate and the phosphorus and sulfur are supplied by zinc C3 to C6 alkyl phosphorodithioate.
21. The composition of Claim 1 wherein the amine is N-tallow-1,3-pro pylenediamine, the boron compound is boric acid, the thickener is lithium 12-hydroxystearate and the phosphorus and sulfur moieties are supplied by zinc C3 to C6 alkyl phosphorodithioate.
22. The composition of Claim 1 wherein the grease vehicle is a mineral oil.
23. The composition of Claim 1 wherein the grease vehicle is a synthetic oil.
24. The composition of Claim 1 wherein the grease vehicle is a mixture of mineral and synthetic oils.
25. The composition of Claim 1 wherein the boron compound is selected from metaborate boric acid, boric oxide and an alkyl borate of the formula
Figure imgb0007
wherein y is 1 to 3, z is 0 to 2, their sum being 3, and R is an alkyl group having 1 to 6 carbon atoms.
26. The composition of Claim 1, wherein the total amount of the thickener is from about 3% to about 20% by weight of the total grease composition.
27. A method of improving the dropping point of a grease composition comprising a major proportion of a grease vehicle and from about 0.01% to about 10% by weight of a reaction product made by reacting an amine of the formula
Figure imgb0008
wherein x is 0 to 2, R, R1, R and R4 are hydrogen or hydrocarbyl groups containing from 1 to 30 carbon atoms, hydroxyalkyl groups containing 2 to 4 carbon atoms, a polyalkoxylated group containing 6 to 20 carbon atoms or the latter group containing sulfur or additional oxygen, at least one of R, R1, R and R being a non-hydrogen group and R2 is a C2 to C4 alkylene group with a boron compound, said method comprising thickening said grease with a thickener containing at least 15% by weight of a hydroxy-containing soap thickener.
28. The method of Claim 27 in which the grease composition additionally contains from about 0.01% to about 10% by weight of a compound containing both phosphorus and sulfur or a mixture of phosphorus-containing and sulfur-containing compounds to supply an equivalent amount of phosphorus and sulfur.
EP85301462A 1984-03-07 1985-03-05 Grease composition containing boron compound and hydroxy containing soap thickener Expired - Lifetime EP0155131B1 (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AT85301462T ATE55406T1 (en) 1984-03-07 1985-03-05 A FAT COMPOSITION CONTAINING A BORON COMPOUND AND A HYDROXY-SUBSTITUTED SOAP AS A THICKENING AGENT.

Applications Claiming Priority (4)

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US58732884A 1984-03-07 1984-03-07
US587328 1984-03-07
US64107784A 1984-08-15 1984-08-15
US641077 2000-08-17

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EP0155131A3 EP0155131A3 (en) 1986-04-23
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AU (1) AU578070B2 (en)
BR (1) BR8501026A (en)
CA (1) CA1280738C (en)
DE (1) DE3579015D1 (en)
NZ (1) NZ211296A (en)
PH (1) PH22814A (en)

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FR2592891A1 (en) * 1986-01-16 1987-07-17 Ntn Toyo Bearing Co Ltd GREASE FOR HOMOCINETIC JOINT.
EP0301727A2 (en) * 1987-07-31 1989-02-01 Exxon Research And Engineering Company Improved load-carrying grease

Families Citing this family (2)

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Publication number Priority date Publication date Assignee Title
EP0157969B2 (en) * 1984-04-05 2000-01-12 The Lubrizol Corporation Organo-borate compositions and their use in lubricants
KR101819132B1 (en) 2015-02-09 2018-01-16 가부시키가이샤 모레스코 Lubricant composition, use thereof and aliphatic ether compound

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GB1400020A (en) * 1972-03-15 1975-07-16 Labofina Sa Lubricating greases
US4382006A (en) * 1979-11-06 1983-05-03 Mobil Oil Corporation Friction reduction additives and compositions thereof
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FR2592891A1 (en) * 1986-01-16 1987-07-17 Ntn Toyo Bearing Co Ltd GREASE FOR HOMOCINETIC JOINT.
EP0301727A2 (en) * 1987-07-31 1989-02-01 Exxon Research And Engineering Company Improved load-carrying grease
EP0301727A3 (en) * 1987-07-31 1989-03-08 Exxon Research And Engineering Company Improved load-carrying grease

Also Published As

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CA1280738C (en) 1991-02-26
JPH0635590B2 (en) 1994-05-11
NZ211296A (en) 1988-07-28
EP0155131B1 (en) 1990-08-08
AU578070B2 (en) 1988-10-13
EP0155131A3 (en) 1986-04-23
JPS60217298A (en) 1985-10-30
DE3579015D1 (en) 1990-09-13
BR8501026A (en) 1985-10-29
PH22814A (en) 1988-12-27
AU3952585A (en) 1985-09-12

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