EP0151859A2 - Fettzusammensetzung - Google Patents

Fettzusammensetzung Download PDF

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Publication number
EP0151859A2
EP0151859A2 EP19840306857 EP84306857A EP0151859A2 EP 0151859 A2 EP0151859 A2 EP 0151859A2 EP 19840306857 EP19840306857 EP 19840306857 EP 84306857 A EP84306857 A EP 84306857A EP 0151859 A2 EP0151859 A2 EP 0151859A2
Authority
EP
European Patent Office
Prior art keywords
composition
monooleate
sulfur
grease
phosphorus
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
EP19840306857
Other languages
English (en)
French (fr)
Other versions
EP0151859A3 (en
EP0151859B1 (de
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 AT84306857T priority Critical patent/ATE77644T1/de
Publication of EP0151859A2 publication Critical patent/EP0151859A2/de
Publication of EP0151859A3 publication Critical patent/EP0151859A3/en
Application granted granted Critical
Publication of EP0151859B1 publication Critical patent/EP0151859B1/de
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

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    • C10M169/00—Lubricating 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
    • C10M169/06—Mixtures of thickeners and additives
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    • C10M117/00—Lubricating compositions characterised by the thickener being a non-macromolecular carboxylic acid or salt thereof
    • C10M117/02—Lubricating compositions characterised by the thickener being a non-macromolecular carboxylic acid or salt thereof having only one carboxyl group bound to an acyclic carbon atom, cycloaliphatic carbon atom or hydrogen
    • C10M117/04—Lubricating compositions characterised by the thickener being a non-macromolecular carboxylic acid or salt thereof having only one carboxyl group bound to an acyclic carbon atom, cycloaliphatic carbon atom or hydrogen containing hydroxy groups
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    • C10M135/02—Sulfurised compounds
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    • C10M137/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing phosphorus
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    • 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
    • C10M2227/00—Organic non-macromolecular compounds containing atoms of elements not provided for in groups C10M2203/00, C10M2207/00, C10M2211/00, C10M2215/00, C10M2219/00 or C10M2223/00 as ingredients in lubricant compositions
    • C10M2227/06—Organic compounds derived from inorganic acids or metal salts
    • 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
    • C10M2227/00—Organic non-macromolecular compounds containing atoms of elements not provided for in groups C10M2203/00, C10M2207/00, C10M2211/00, C10M2215/00, C10M2219/00 or C10M2223/00 as ingredients in lubricant compositions
    • C10M2227/06—Organic compounds derived from inorganic acids or metal salts
    • C10M2227/061—Esters derived from boron
    • 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
    • C10M2227/00—Organic non-macromolecular compounds containing atoms of elements not provided for in groups C10M2203/00, C10M2207/00, C10M2211/00, C10M2215/00, C10M2219/00 or C10M2223/00 as ingredients in lubricant compositions
    • C10M2227/06—Organic compounds derived from inorganic acids or metal salts
    • C10M2227/061—Esters derived from boron
    • C10M2227/062—Cyclic esters
    • 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
    • C10M2227/00—Organic non-macromolecular compounds containing atoms of elements not provided for in groups C10M2203/00, C10M2207/00, C10M2211/00, C10M2215/00, C10M2219/00 or C10M2223/00 as ingredients in lubricant compositions
    • C10M2227/06—Organic compounds derived from inorganic acids or metal salts
    • C10M2227/063—Complexes of boron halides
    • 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
    • C10M2227/00—Organic non-macromolecular compounds containing atoms of elements not provided for in groups C10M2203/00, C10M2207/00, C10M2211/00, C10M2215/00, C10M2219/00 or C10M2223/00 as ingredients in lubricant compositions
    • C10M2227/06—Organic compounds derived from inorganic acids or metal salts
    • C10M2227/065—Organic compounds derived from inorganic acids or metal salts derived from Ti or Zr
    • 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
    • C10M2227/00—Organic non-macromolecular compounds containing atoms of elements not provided for in groups C10M2203/00, C10M2207/00, C10M2211/00, C10M2215/00, C10M2219/00 or C10M2223/00 as ingredients in lubricant compositions
    • C10M2227/06—Organic compounds derived from inorganic acids or metal salts
    • C10M2227/066—Organic compounds derived from inorganic acids or metal salts derived from Mo or W
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2010/00—Metal present as such or in compounds
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2010/00—Metal present as such or in compounds
    • C10N2010/02—Groups 1 or 11
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2010/00—Metal present as such or in compounds
    • C10N2010/04—Groups 2 or 12
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2010/00—Metal present as such or in compounds
    • C10N2010/12—Groups 6 or 16

Definitions

  • the invention is concerned with a novel group of compositions. It more particularly relates to a grease composition comprising oil, hydroxy-containing soap thickener and borated hydroxy-containing esters and optionally containing phosphorus and sulfur moities.
  • Alcohols are well known for their lubricity properties when formulated into lubricating oils and for their water scavenging characteristics when blended into fuels.
  • the use of vicinal hydroxyl-containing alkyl carboxylates such as gylcerol monoolerate have also found widespread use as lubricity additives.
  • U.S. 2,788,326 discloses some of the esters suitable for the present invention, such as gylcerol monooleate, as minor components of lubricating oil compositions.
  • U.S. 3,235,498 discloses the same ester as an additive to other oils.
  • U.S. 2,443,578 teaches esters wherein the free hydroxyl is found in the acid portion, as for example, in tartaric acid.
  • an improved grease composition containing a major proportion of a grease and a minor amount of a compound prepared by reacting a hydrocarbyl ester of the formula wherein R and R are hydrocarbyl groups, or hydroxyhydrocarbyl groups, containing 1 to 40 carbon atoms, preferably 8 to 20 carbon atoms, at least one of R or R being a hydroxyhydrocaruyl group, and n is 1 to 5, with a boron compound which may be a metaborate or similar boron source, boric acid, boric oxide or an alkyl borate of the formula wherein x is 1 to 3, y is 0 to 2, their sum being 3, and R is an alkyl group containing from 1 to 6 carbon atoms, the improvement comprising employing at least 15% by weight of a hydroxy-containing soap thickener to prepare the grease.
  • Hydrocarbyl and hydroxyhydrocarbyl include alkyl, aryl, aralkyl, alkaryl and cycloalkyl groups.
  • the ester is overborated, meaning the presence in the product of more than a stoichiometric amount of boron.
  • the esters may contain from 1 to 5 hydroxy groups in the molecule. They may all be attached to either R or R or they may be attached to R and R in varying proportions. Further, the hydroxy groups can be at any position or positions along the chain of R or R l . It will be understood that the esters contain at least one free hydroxy group prior to reaction with the boron compound.
  • esters can be made by methods well known in the art. In general, they are made by reacting the desired acid or acyl halide and alcohol at temperatures and for times one skilled in the art can easily select. To give an ester having a free hydroxy group, either in R or R 1 , reactant proportions are chosen accordingly, as one skilled in the art will understand.
  • Suitable hydroxy-containing esters prior to boration include trimethylolpropane monooleate, trimethylolpropane dioleate, trimethylolpropane monostearate, trimethylolpropane distearate, trimethylolpropane monopelargonate, trimethylolpropane monooleate monopelargonate, pentaerylthritol monooleate, pentaerythritol dioleate, pentaerythritol trioleate, pentaerythritol monoisostearate, pentaerythritol monooleate monopelargonate, pentaerythritol monoisostearate, monopelargonate or monohexanoate, pentaerythritol tripelargonate, glycerol monooleate, glycerol dioleate, glycerol monostearate, glycerol monoricinoleate, g
  • the borated esters of the invention can be made by reacting an ester as defined above with a boron compound, such as boric oxide, a metaborate, boric acid, an alkyl borate or mixtures thereof.
  • a boron compound such as boric oxide, a metaborate, boric acid, an alkyl borate or mixtures thereof.
  • the resulting products are primarily borate esters, but other possible products present are the products of reaction between ester dimers, or higher oligomers, and a boron compound to form the corresponding borate esters.
  • the boron compound used is boric acid, boric oxide or an alkyl borate, preferably boric acid.
  • the alkyl borates include the mono-, di- and trialkyl borates, such as the mono-, di- and trimethyl borates, mono-, di- and triethyl borates, mono-, di- and tripropyl borates, mono-, di- and tributyl borates, mono-, di- and tripentyl borates and mono-, di- and trihexyl borates.
  • the reaction to form the borate ester can be carried out at from 80°C to 260°C, preferably from 110°C to 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 ester to boron compound be from 1 to 4, preferably from 1 to 2, or more preferably, of about 1.
  • the ester may be reacted with an excess of the borating species to form a borate ester containing from 0.1% by weight of boron to more than 10% of boron.
  • reaction can be advantageously run at from 1 to 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 soluents which include propanol, butanol, and hexamethyleneglycol can be used. Mixtures of alcoholic and hydrocarbon solvents can be used also.
  • reaction time is not critical. Thus, any phase of the process can be carried out in from 1 to 20 hours.
  • a narrow class of thickening agents is used to make the grease of this invention.
  • the thickening agents contain 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 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 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 members. Significant benefit can be attained using as little thereof as 15% by weight of the total thickener.
  • a complementary amount such as up to 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 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.
  • Manufacture of the thickening agents can be done in a variety of grease-making equipment such as open kettles at reduced, atmospheric, or positive pressures; higher pressure reaction chambers which may be operated as high as 180 psig; or continuous manufacturing equipment.
  • the temperature range from the bulk grease under manufacture may range from 15°C (60°F) to 238°C (460°F).
  • 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 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 is well known to those skilled in the art.
  • 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 R 3 is a hydrocarbyl group containing 3 to 18 carbon atoms, M is preferably a metal, but may be a non-metal, such as one of those mentioned hereinbelow, n is the valence of M and Z is oxygen or sulfur, at least one Z being sulfur.
  • R 3 is preferably an alkyl group and may be a propyl, butyl, pentyl, hexyl, octyl, decyl, dodecyl, tetradecyl or octadecyl group, including those derived from isopropanol, propanol, 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.
  • Non-metallic ions include organic groups derived from vinyl esters such as vinyl acetate, vinyl ethers such as butyl vinyl ether and epoxides such as propylene oxide and 1,2-epoxydodecane.
  • the non-metallic ions may also be derived from 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, p hosphorodithionyl disulfide and sulfurized jojoba oil.
  • the phosphites include 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 thickener will have at least 15% by weight of a metal or non-metal hydroxyl-containing soap therein, the total thickener being from 3% to 20% by weight of the grease composition.
  • the composition may have therein from 0.01% to 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.
  • 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 esters and the phosphorus- and/or sulfur-containing compound(s) are effectively employed in combined amounts from 0.02% to 20% by weight, and preferably from 0.2% to 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 45 SSU at 37.8°C to 6000 SSU at 37.8°C, and preferably from 50 to 250 SSU at 99°C.
  • These oils may have viscosity indexes ranging to 100 or higher. Viscosity indexes from 70 to 95 are preferred.
  • the average molecular weights of these oils may range from 250 to 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 hydroxy-containing ester 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 any of the prior greases now known.
  • the grease composition 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.
  • Glycerol monooleate consisting of a mixture of about 60% of glycerol monooleate and about 40% of glycerol dioleate, xylene (38 g) and butanol (122 g) were charged to a reactor equipped with a heater, an agitator and a condenser. The reactor contents were heated to 50°C, and boric acid (100 g) was charged to the ester and solvent. The reaction mixture was heated to 204°C and was held there for about 3 hours until water evolution ceased. The reactor contents were cooled to 155°C and vacuum (to less than 2 mm of Hg) was applied to remove the solvents. The crude product was further cooled to 105°C and it was then filtered through diatomaceous earth to yield a viscous, amber liquid.
  • 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 177°C in a closed contactor. After depressuring and dehydration of the thickener in an open kettle, sufficient mineral oil was added to reduce the thickener content to 9.0%. After cooling to 99°C, a typical grease additive package, consisting of an amine antioxidant, phenolic antioxident, metallic dithiophospate, sulfur-containing metal deactivator and nitrogen containing antirust additives, was added. This produced a base grease for evaluating the effect of borated hydroxyl-containing esters on grease dropping point and other properties.
  • Example 3 To the grease of Example 3 was added 2 wt. % of the borated glycerol monooleate of Example 1. The addition was accomplished in a laboratory grease blender from 110°C to 116°C.
  • Example 2 Same as Example 4, except that 2 wt. % of the borated glycerol monooleate of Example 2 was used.
  • Example 8 clearly shows no dropping point improvement when the borated ester is added to a non-hydroxy-containing carboxylate soap thickened grease.

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  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Organic Chemistry (AREA)
  • Lubricants (AREA)
EP84306857A 1984-02-06 1984-10-09 Fettzusammensetzung Expired - Lifetime EP0151859B1 (de)

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US64107884A 1984-08-15 1984-08-15
US577454 1984-08-15
US641078 1984-08-15

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EP0151859A3 EP0151859A3 (en) 1986-04-16
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JP (1) JPH0694557B2 (de)
AU (1) AU575596B2 (de)
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Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0213885A2 (de) * 1985-08-27 1987-03-11 Mobil Oil Corporation Borhaltige Brenzcatechinverbindungen und hydroxysubstituierte Seifen als Verdickungsmittel enthaltende Fettzusammensetzungen
EP0597712A1 (de) * 1992-11-12 1994-05-18 The Lubrizol Corporation Schmierfettzusammensetzungen

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2943054A (en) * 1958-03-21 1960-06-28 Union Oil Co Shear stable barium 12-hydroxy stearate grease containing a boron ester compound
GB1400020A (en) * 1972-03-15 1975-07-16 Labofina Sa Lubricating greases
GB2102023A (en) * 1981-07-01 1983-01-26 Chevron Res Reduction of fuel consumption of internal combustion engines and composition therefor
GB2106133A (en) * 1981-09-22 1983-04-07 Chevron Res Method of reducing brake chatter of oil-immersed disc brakes
GB2125431A (en) * 1982-08-03 1984-03-07 Karonite Chem Co Ltd Lubricating oils with boric acid esters

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2943054A (en) * 1958-03-21 1960-06-28 Union Oil Co Shear stable barium 12-hydroxy stearate grease containing a boron ester compound
GB1400020A (en) * 1972-03-15 1975-07-16 Labofina Sa Lubricating greases
GB2102023A (en) * 1981-07-01 1983-01-26 Chevron Res Reduction of fuel consumption of internal combustion engines and composition therefor
GB2106133A (en) * 1981-09-22 1983-04-07 Chevron Res Method of reducing brake chatter of oil-immersed disc brakes
GB2125431A (en) * 1982-08-03 1984-03-07 Karonite Chem Co Ltd Lubricating oils with boric acid esters

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0213885A2 (de) * 1985-08-27 1987-03-11 Mobil Oil Corporation Borhaltige Brenzcatechinverbindungen und hydroxysubstituierte Seifen als Verdickungsmittel enthaltende Fettzusammensetzungen
EP0213885A3 (en) * 1985-08-27 1988-09-21 Mobil Oil Corporation Grease compositions containing borated compounds and hydroxy-containing soap thickeners
EP0597712A1 (de) * 1992-11-12 1994-05-18 The Lubrizol Corporation Schmierfettzusammensetzungen

Also Published As

Publication number Publication date
EP0151859A3 (en) 1986-04-16
DE3485789D1 (de) 1992-07-30
EP0151859B1 (de) 1992-06-24
BR8406567A (pt) 1985-10-15
DE3485789T2 (de) 1992-12-24
CA1231703A (en) 1988-01-19
AU3483484A (en) 1985-08-15
AU575596B2 (en) 1988-08-04
JPS60166399A (ja) 1985-08-29
NZ209963A (en) 1987-08-31
JPH0694557B2 (ja) 1994-11-24

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