US3297574A - Lubricating compositions containing ep agents - Google Patents

Lubricating compositions containing ep agents Download PDF

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Publication number
US3297574A
US3297574A US338588A US33858864A US3297574A US 3297574 A US3297574 A US 3297574A US 338588 A US338588 A US 338588A US 33858864 A US33858864 A US 33858864A US 3297574 A US3297574 A US 3297574A
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Prior art keywords
acid
esters
aliphatic
ester
agents
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US338588A
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Alexander C B Macphail
Francis T Barcroft
Charles B Milne
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Shell USA Inc
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Shell Oil Co
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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
    • C10M3/00—Liquid compositions essentially based on lubricating components other than mineral lubricating oils or fatty oils and their use as lubricants; Use as lubricants of single liquid substances
    • C—CHEMISTRY; METALLURGY
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    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/02—Hydroxy compounds
    • C10M2207/023—Hydroxy compounds having hydroxy groups bound to carbon atoms of six-membered aromatic rings
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    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/02—Hydroxy compounds
    • C10M2207/023—Hydroxy compounds having hydroxy groups bound to carbon atoms of six-membered aromatic rings
    • C10M2207/024—Hydroxy compounds having hydroxy groups bound to carbon atoms of six-membered aromatic rings having at least two phenol groups but no condensed ring
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    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/02—Hydroxy compounds
    • C10M2207/023—Hydroxy compounds having hydroxy groups bound to carbon atoms of six-membered aromatic rings
    • C10M2207/026—Hydroxy compounds having hydroxy groups bound to carbon atoms of six-membered aromatic rings with tertiary alkyl groups
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    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/10—Carboxylix acids; Neutral salts thereof
    • C10M2207/12—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms
    • C10M2207/121—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms having hydrocarbon chains of seven or less carbon atoms
    • C10M2207/123—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms having hydrocarbon chains of seven or less carbon atoms polycarboxylic
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    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/10—Carboxylix acids; Neutral salts thereof
    • C10M2207/12—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms
    • C10M2207/129—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms having hydrocarbon chains of thirty or more carbon atoms
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    • C10M2207/10—Carboxylix acids; Neutral salts thereof
    • C10M2207/22—Acids obtained from polymerised unsaturated acids
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    • C10M2207/28—Esters
    • C10M2207/281—Esters of (cyclo)aliphatic monocarboxylic acids
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    • C10M2207/28—Esters
    • C10M2207/282—Esters of (cyclo)aliphatic oolycarboxylic acids
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    • C10M2207/28—Esters
    • C10M2207/283—Esters of polyhydroxy compounds
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    • C10M2207/28—Esters
    • C10M2207/286—Esters of polymerised unsaturated acids
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    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/28—Esters
    • C10M2207/30—Complex esters, i.e. compounds containing at leasst three esterified carboxyl groups and derived from the combination of at least three different types of the following five types of compounds: monohydroxyl compounds, polyhydroxy xompounds, monocarboxylic acids, polycarboxylic acids or hydroxy carboxylic acids
    • C10M2207/302—Complex esters, i.e. compounds containing at leasst three esterified carboxyl groups and derived from the combination of at least three different types of the following five types of compounds: monohydroxyl compounds, polyhydroxy xompounds, monocarboxylic acids, polycarboxylic acids or hydroxy carboxylic acids derived from the combination of monocarboxylic acids, dicarboxylic acids and dihydroxy compounds only and having no free hydroxy or carboxyl groups
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    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/28—Esters
    • C10M2207/30—Complex esters, i.e. compounds containing at leasst three esterified carboxyl groups and derived from the combination of at least three different types of the following five types of compounds: monohydroxyl compounds, polyhydroxy xompounds, monocarboxylic acids, polycarboxylic acids or hydroxy carboxylic acids
    • C10M2207/304—Complex esters, i.e. compounds containing at leasst three esterified carboxyl groups and derived from the combination of at least three different types of the following five types of compounds: monohydroxyl compounds, polyhydroxy xompounds, monocarboxylic acids, polycarboxylic acids or hydroxy carboxylic acids derived from the combination of monohydroxy compounds, dihydroxy compounds and dicarboxylic acids only and having no free hydroxy or carboxyl groups
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    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/28—Esters
    • C10M2207/34—Esters having a hydrocarbon substituent of thirty or more carbon atoms, e.g. substituted succinic acid derivatives
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    • C10M2209/00—Organic macromolecular compounds containing oxygen as ingredients in lubricant compositions
    • C10M2209/02—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M2209/08—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds containing monomers having an unsaturated radical bound to a carboxyl radical, e.g. acrylate type
    • C10M2209/082—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds containing monomers having an unsaturated radical bound to a carboxyl radical, e.g. acrylate type monocarboxylic
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    • C10M2209/00—Organic macromolecular compounds containing oxygen as ingredients in lubricant compositions
    • C10M2209/02—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M2209/08—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds containing monomers having an unsaturated radical bound to a carboxyl radical, e.g. acrylate type
    • C10M2209/084—Acrylate; Methacrylate
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    • 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
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    • C10M2209/103—Polyethers, i.e. containing di- or higher polyoxyalkylene groups
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    • 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
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    • C10M2209/10—Macromolecular compoundss obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M2209/11—Complex polyesters
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    • C10M2211/00—Organic non-macromolecular compounds containing halogen as ingredients in lubricant compositions
    • C10M2211/02—Organic non-macromolecular compounds containing halogen as ingredients in lubricant compositions containing carbon, hydrogen and halogen only
    • C10M2211/024—Organic non-macromolecular compounds containing halogen as ingredients in lubricant compositions containing carbon, hydrogen and halogen only aromatic
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    • C10M2211/06—Perfluorinated compounds
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    • C10M2213/06—Perfluoro polymers
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    • C10M2215/02—Amines, e.g. polyalkylene polyamines; Quaternary amines
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    • C10M2215/02—Amines, e.g. polyalkylene polyamines; Quaternary amines
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    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
    • C10M2219/10—Heterocyclic compounds containing sulfur, selenium or tellurium compounds in the ring
    • C10M2219/104—Heterocyclic compounds containing sulfur, selenium or tellurium compounds in the ring containing sulfur and carbon with nitrogen or oxygen in the ring
    • 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
    • C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
    • C10M2219/10—Heterocyclic compounds containing sulfur, selenium or tellurium compounds in the ring
    • C10M2219/104—Heterocyclic compounds containing sulfur, selenium or tellurium compounds in the ring containing sulfur and carbon with nitrogen or oxygen in the ring
    • C10M2219/106—Thiadiazoles
    • 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
    • C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
    • C10M2219/10—Heterocyclic compounds containing sulfur, selenium or tellurium compounds in the ring
    • C10M2219/104—Heterocyclic compounds containing sulfur, selenium or tellurium compounds in the ring containing sulfur and carbon with nitrogen or oxygen in the ring
    • C10M2219/108—Phenothiazine
    • 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
    • C10M2223/00—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
    • C10M2223/02—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having no phosphorus-to-carbon bonds
    • C10M2223/04—Phosphate esters
    • C10M2223/047—Thioderivatives not containing metallic elements
    • 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
    • C10M2229/00—Organic macromolecular compounds containing atoms of elements not provided for in groups C10M2205/00, C10M2209/00, C10M2213/00, C10M2217/00, C10M2221/00 or C10M2225/00 as ingredients in lubricant compositions
    • C10M2229/04—Siloxanes with specific structure
    • C10M2229/041—Siloxanes with specific structure containing aliphatic substituents
    • 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
    • C10N2020/00—Specified physical or chemical properties or characteristics, i.e. function, of component of lubricating compositions
    • C10N2020/01—Physico-chemical properties
    • 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
    • C10N2030/00—Specified physical or chemical properties which is improved by the additive characterising the lubricating composition, e.g. multifunctional additives
    • C10N2030/08—Resistance to extreme temperature
    • 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
    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/12—Gas-turbines
    • 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
    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/12—Gas-turbines
    • C10N2040/13—Aircraft turbines

Definitions

  • a class of compounds of this type are commercially 7 Claims 232-465) 10 available under the trade name Aroclor from Mon- This invention relates to synthetic lubricating composisanto Chemical Company. Particularly preferred are tions capable of functioning over a wide temperature r ted (40-70%) diphenyls commercially availrange and under extreme pressure and wear conditions.
  • esters of mono o polyhydric l effects of these compounds do not substantially increase h d li h i di -b li id h as di(2 h 1- with a corresponding increase of additive concentration.
  • ester lubrrcatmg 011 by the additlon of mmor amounts Th th f th d of each of (1) a chlorinated polyaryl compound and 6 com ma O asefa mves i uces T' llent extreme-pressure propertles not attainable with (2) a trraryl ester of phosphorothiomc 301d. More spe- 40 Ce cificauy, improved lubricating Compositions of the the conventional chlorinated polyaryl additive alone.
  • In vention comprise; Tables I and H, Examples VI-VIII below, 1t 1s shown A aliphatic carboxylic lubricating base; that the rate of increase of scufimg load with increas- (B) A minor amount f one or more chlorinated balsa ing Arochlor concentration in the presence of 2% triaryl hydrocarbon represented by th f l phenyl phosphorothionate is considerably higher than in the absence of this compound.
  • the resulting lubricat- Ar-Ar ing oil has excellent extreme-pressure properties which ⁇ J (31y are only available with the use of the phosphorothionate
  • Ar is a mono or polynuclear aromatic hydrocar- 5O additive bon such as benzene, naphthalene, or anthracene
  • prefisfaveml W1th varymg Arochlor P eramy at least one f which is benzene x and y are tration, with and without tnphenyl phosphorothionate, integers of f 1 to 3 and f bl f 2 to 4, the were tested for their load-carrying capacity on an I.A.E.
  • Hcrcolube A and Hercolube C are triphenyl C -C acid esters of pentaerythritol) and Hercoluhe phosphorothionate, tritolyl phosphorthinate, tribenzyl F (C -C acid esters of dipentaerythritol) are partlcphosphorothionate, and trixylyl phosphorthionate.
  • preferred ester is triphenyl phosphorothionate.
  • the aliphatic carboxylic acid esters need not necessarily
  • the aliphatic carboxylic acid ester lubricating oil be simple esters or mixtures thereof but may be what are bases which are used in lubricating oil compositions termed complex esters made by esterifying in one or according to the invention may be esters of a monomore stages, an aliphatic dicarboxylic acid and a glycol hydric aliphatic alcohol having from 3 to 18 arbon or polyglycol optionally together with an aliphatic monoatoms in the molecule, with a monobasic aliphatic acid CaI'bOXYIiC acid and/01' an aliphatic monohydri?
  • a typical complex ester is that made by esterifying two example isodecyl pelargonate, moles of an aliphatic dicarboxylic acid, one mole of a
  • a further class of aliphatic carboxylic acid esters which glycol P y y and two moles of an aliphatic mono may be used is the aliphatic esters of monobasic carboxylic hydfic 31601101 having a formula!
  • R is an alkylene or oxyalkylene group
  • R is an dipropylene glycol, with heptylic acid, n-octoic acid and alkylene group and R2 15 an alkyl group pelaroonic acii
  • Preferred complex esters of the type are those wherein A particularly preferred class of aliphatic acid esters R 18 an alkylene oxyalkylene group having from 2 to 20 for use in the lubricating oil compositions of the invencarPon R118 an alkylene group opnonally branyhed tion is the aliphatic diester of diabasic carboxylic acids fig havmg t to 20 g f fi i and R2 i having 6 to 20 carbon atoms and monohydric alcohols
  • Particularly preferred aliphatic .esters f a so m e u F 5 diesters of dicarboxylic acids are those derived from pqsmons accor mg tot Especla.y Sulta monohydric alcohols having a branched chain, for exammixtures are those of l ahphatlc estefs of dlcarboxyhc ple 2-ethyl hexanol and especially those having no hydroacids gg q %g i, alcholls and i gen on the beta carbon atom, for example 2,2-dimethy1 g i f g b l esters.
  • pentaerythritol dipantatenh ac d ester lubricating OllS, for example thickeners, antithritol and trimethylolpropane oxidants, antilacqnermg agents, ant -foaming agents, dyes
  • esters are pentaerythrityl butyrate, anti-corrosion agents metal deactivtors and addmonal pentaerythrityl tetrabutyrate, pentaerythrityl tetravalerate, eXtremePYeSwm addmves
  • tlllckeners there be used polyalkylene glycols dicaproate, pentaerythrityl butyratecaproate divalerate, and the.
  • dipentaerythrityl mixed may be an alkylene radical, preferably an alkylene radihexaesters of C fatty acids and trimethylolpropane cal with two to eight carbon atoms. Still more preferred .heptylate.
  • polyalkylenetglycols are those wherein the alkylene radi- A class of pentaerythritol esters useful as base oils are cal is an ethylene or propylene radical.
  • the chain may, for instance, consist of both oxyethylene and oxypropylene radicals.
  • the polyoxyalkylene chain contains different alkylene radicals --these may be randomly distributed throughout the molecule or may be arranged in regularly recurring units or blocks, each consisting of one or a plurality of similar oxyalkylene radicals.
  • Particularly preferred polyalkylene glycols are those having blocks of, for example, 1 to 8 oxyethylene radicals alternating With blocks of, for example, 1 to 8 oxypropylene radicals.
  • radicals represented in the above general formula by R and/ or R are hydrocarbon radicals
  • the radicals may be saturated or unsaturated, straight chained or branched, or similar or dissimilar, nonaromatic hydrocarbon radicals.
  • R is hydrogen and R is an alkyl group such as a propyl, butyl, pentyl or decyl group.
  • radicals R and/ or R are acyl radicals
  • the radicals may be derived from any carboxylic acid.
  • the molecular weight of the polyalkylene glycols may vary over a wide range but preferably is from 350 to about 10,000; molecular weights between 800 and 6,000 are particularly preferred.
  • the polyalkylene glycol thickener may be used in a concentration of between 5% and 50%, preferably between and 40% based on the whole composition.
  • Suitable polyalkylene glycols are those sold under the name Ucon Fluids (the word Ucon is a Registered Trademark) manufactured by the Carbide and Chemical Corporation and Oxilube the word Oxilube is a trademark) manufactured by Shell Internationale Chemical Company and are described in US. Patents 2,425,755, 2,425,845 and 2,952,335.
  • Ucon fluids of the LBX series made by copolymerizing ethylene oxide and 1,2- propylene oxide and having viscosities (at 100 F.) of about 140 and 370 cs. respectively have been found to give excellent results.
  • antioxidants which may be used in the lubricating oil composition according to the invention there are mentioned alkylated phenols, for example 2,6-ditertiary butyl- 4-methyl phenol, alkylated bisphenols, for example 4,4'- methylene bis(2,6-ditertiary butyl phenol), aromatic amines, for example phenyl-wnaphthylamine, phenyl-B- naphthylarnine, diphe-nylamine and alkyl substituted derivatives thereof.
  • alkylated phenols for example 2,6-ditertiary butyl- 4-methyl phenol
  • alkylated bisphenols for example 4,4'- methylene bis(2,6-ditertiary butyl phenol)
  • aromatic amines for example phenyl-wnaphthylamine, phenyl-B- naphthylarnine, diphe-nylamine and alkyl substituted derivatives thereof.
  • antioxidants are the thiodiarylamines, for example phenothiazine and 3,6-dioctylphenothiazine.
  • Mixtures of antioxidants may also be used, particularly mixtures of thiodiarylamines and diarylamines, for example a mixture of phenothiazine and phenyl-a-naphthylamine.
  • anti-foaming agents for example polydimethylsiloxanes having viscosities from 100100,000 cs. at C.
  • anti-corrosion agents for example aluminum silicates, aluminum silicates, and zinc silicates.
  • metal deactivators for example benzotriazole and S-methylbenzotriazole.
  • a synthetic lubricating oil comprising (1) a major amount of an aliphatic carboxylic acid ester oil base,
  • composition of claim 1 wherein the aliphatic carboxylicacid ester oil base consists essentially of an aliphatic diester of dibasic carboxylic acids having from 6 to 20 carbon atoms and monohydric alcohols having from 1 to 12 carbon atoms.
  • a synthetic lubricating oil composition comprising (1) a major amount of an aliphatic carboxylic acid ester oil base,
  • a chlorinated polyaryl hydrocarbon having the formula wherein Ar is an aromatic hydrocarbon selected from the group consisting of benzene, naphthalene, and anthracene, x and y are integers of from 1 to 8, and z is an integer of from 1 to 10, and
  • composition of claim 4 wherein the triaryl ester of phosphorothionic acid is triphenyl phosphorothionate.
  • composition of claim 4 containing an antioxidant selected from the group consisting of 2,6-ditertiary butyl-4-methyl phenol; 4,4'-methylene bis(2,6-d.itertiary butyl phenol), phenyl a-naphthylamine, phenyl S-naphthylamine, diphenylamine, phenothiazine, and 3,6-dioctylphenothiazine.
  • an antioxidant selected from the group consisting of 2,6-ditertiary butyl-4-methyl phenol; 4,4'-methylene bis(2,6-d.itertiary butyl phenol), phenyl a-naphthylamine, phenyl S-naphthylamine, diphenylamine, phenothiazine, and 3,6-dioctylphenothiazine.
  • a synthetic lubricating oil comprising a major amount of an aliphatic carboxylic acid ester oil base, 0.5 to 10% by weight of diphenyls containing 40 to by weight chlorine, and l to 6% by weight of triphenyl phosphorothionate.

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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)
US338588A 1963-02-21 1964-01-20 Lubricating compositions containing ep agents Expired - Lifetime US3297574A (en)

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Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3493509A (en) * 1967-12-04 1970-02-03 Us Army Synthetic lubricating oil for timing mechanisms
US4116874A (en) * 1975-08-27 1978-09-26 Nippon Oil Co., Ltd. Compressor oil compositions
US4175047A (en) * 1978-09-25 1979-11-20 Mobil Oil Corporation Synthetic ester and hydrogenated olefin oligomer lubricant and method of reducing fuel consumption therewith

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2157452A (en) * 1934-03-31 1939-05-09 Standard Oil Co California Extreme pressure lubricating compositions
US2242260A (en) * 1937-01-22 1941-05-20 Lubri Zol Dev Corp Lubricating composition
US2820766A (en) * 1953-09-17 1958-01-21 Wakefield & Co Ltd C C Lubricating compositions
US3030304A (en) * 1958-02-11 1962-04-17 Castrol Ltd Lubricating compositions
US3218256A (en) * 1959-01-14 1965-11-16 Castrol Ltd Lubricating compositions

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2157452A (en) * 1934-03-31 1939-05-09 Standard Oil Co California Extreme pressure lubricating compositions
US2242260A (en) * 1937-01-22 1941-05-20 Lubri Zol Dev Corp Lubricating composition
US2820766A (en) * 1953-09-17 1958-01-21 Wakefield & Co Ltd C C Lubricating compositions
US3030304A (en) * 1958-02-11 1962-04-17 Castrol Ltd Lubricating compositions
US3218256A (en) * 1959-01-14 1965-11-16 Castrol Ltd Lubricating compositions

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3493509A (en) * 1967-12-04 1970-02-03 Us Army Synthetic lubricating oil for timing mechanisms
US4116874A (en) * 1975-08-27 1978-09-26 Nippon Oil Co., Ltd. Compressor oil compositions
US4175047A (en) * 1978-09-25 1979-11-20 Mobil Oil Corporation Synthetic ester and hydrogenated olefin oligomer lubricant and method of reducing fuel consumption therewith

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NL6401503A (US20110009641A1-20110113-C00185.png) 1964-08-24
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DE1247525B (de) 1967-08-17

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