US3330762A - Lubricant compositions - Google Patents

Lubricant compositions Download PDF

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Publication number
US3330762A
US3330762A US417818A US41781864A US3330762A US 3330762 A US3330762 A US 3330762A US 417818 A US417818 A US 417818A US 41781864 A US41781864 A US 41781864A US 3330762 A US3330762 A US 3330762A
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United States
Prior art keywords
dipyridylamine
oil
ester
weight
esters
Prior art date
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Expired - Lifetime
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US417818A
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English (en)
Inventor
Kenneth T Wendler
Robert C Spillman
James R Price
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Shell USA Inc
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Shell Oil Co
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Publication date
Application filed by Shell Oil Co filed Critical Shell Oil Co
Priority to US417818A priority Critical patent/US3330762A/en
Priority to FR41559A priority patent/FR1456439A/fr
Priority to GB52327/65A priority patent/GB1077606A/en
Priority to DES100877A priority patent/DE1278662B/de
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Publication of US3330762A publication Critical patent/US3330762A/en
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    • 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
    • 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
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/10—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
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/10—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
    • C—CHEMISTRY; METALLURGY
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    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/10—Carboxylix acids; Neutral salts thereof
    • C10M2207/22—Acids obtained from polymerised unsaturated acids
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/28—Esters
    • C10M2207/281—Esters of (cyclo)aliphatic monocarboxylic acids
    • C—CHEMISTRY; METALLURGY
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    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/28—Esters
    • C10M2207/282—Esters of (cyclo)aliphatic oolycarboxylic acids
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
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    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/28—Esters
    • C10M2207/283—Esters of polyhydroxy compounds
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    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/28—Esters
    • C10M2207/286—Esters of polymerised unsaturated acids
    • C—CHEMISTRY; METALLURGY
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    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/28—Esters
    • C10M2207/287—Partial esters
    • C10M2207/288—Partial esters containing free carboxyl groups
    • C—CHEMISTRY; METALLURGY
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    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/28—Esters
    • C10M2207/287—Partial esters
    • C10M2207/289—Partial esters containing free hydroxy groups
    • C—CHEMISTRY; METALLURGY
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    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/28—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
    • C—CHEMISTRY; METALLURGY
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    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/28—Esters
    • C10M2207/30—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
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
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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
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2209/00—Organic macromolecular compounds containing oxygen as ingredients in lubricant compositions
    • C10M2209/10—Macromolecular compoundss obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M2209/103—Polyethers, i.e. containing di- or higher polyoxyalkylene groups
    • C10M2209/104—Polyethers, i.e. containing di- or higher polyoxyalkylene groups of alkylene oxides containing two carbon atoms only
    • C—CHEMISTRY; METALLURGY
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    • C10M2209/00—Organic macromolecular compounds containing oxygen as ingredients in lubricant compositions
    • C10M2209/10—Macromolecular compoundss obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M2209/103—Polyethers, i.e. containing di- or higher polyoxyalkylene groups
    • C10M2209/105—Polyethers, i.e. containing di- or higher polyoxyalkylene groups of alkylene oxides containing three carbon atoms only
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    • C10M2209/00—Organic macromolecular compounds containing oxygen as ingredients in lubricant compositions
    • C10M2209/10—Macromolecular compoundss obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M2209/103—Polyethers, i.e. containing di- or higher polyoxyalkylene groups
    • C10M2209/109—Polyethers, i.e. containing di- or higher polyoxyalkylene groups esterified
    • C—CHEMISTRY; METALLURGY
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    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2215/02—Amines, e.g. polyalkylene polyamines; Quaternary amines
    • C10M2215/06—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to carbon atoms of six-membered aromatic rings
    • C10M2215/064—Di- and triaryl amines
    • C—CHEMISTRY; METALLURGY
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    • C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2215/22—Heterocyclic nitrogen compounds
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
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    • C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2215/22—Heterocyclic nitrogen compounds
    • C10M2215/221—Six-membered rings containing nitrogen and carbon only
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
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    • C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2215/22—Heterocyclic nitrogen compounds
    • C10M2215/225—Heterocyclic nitrogen compounds the rings containing both nitrogen and oxygen
    • C—CHEMISTRY; METALLURGY
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    • C10M2215/22—Heterocyclic nitrogen compounds
    • C10M2215/225—Heterocyclic nitrogen compounds the rings containing both nitrogen and oxygen
    • C10M2215/226—Morpholines
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    • C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2215/30—Heterocyclic compounds
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    • C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
    • C10M2219/06—Thio-acids; Thiocyanates; Derivatives thereof
    • C10M2219/062—Thio-acids; Thiocyanates; Derivatives thereof having carbon-to-sulfur double bonds
    • C10M2219/066—Thiocarbamic type compounds
    • C10M2219/068—Thiocarbamate metal salts
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    • C10M2223/00—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
    • C10M2223/06—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having phosphorus-to-carbon bonds
    • C10M2223/063—Ammonium or amine salts
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    • C10M2223/06—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having phosphorus-to-carbon bonds
    • C10M2223/065—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having phosphorus-to-carbon bonds containing sulfur
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    • C10M2229/02—Unspecified siloxanes; Silicones
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    • C10M2229/04—Siloxanes with specific structure
    • C10M2229/05—Siloxanes with specific structure containing atoms other than silicon, hydrogen, oxygen or carbon
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    • 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
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    • C10N2020/00—Specified physical or chemical properties or characteristics, i.e. function, of component of lubricating compositions
    • C10N2020/01—Physico-chemical properties
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    • 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
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    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/02—Bearings
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    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/12—Gas-turbines
    • C—CHEMISTRY; METALLURGY
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    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/12—Gas-turbines
    • C10N2040/13—Aircraft turbines

Definitions

  • This invention relates to synthetic ester lubricant compositions containing a novel antioxidant combination. More particularly, this invention relates to ester lubricating oils containing a combination of diphenylarnine and a dipyridylamine.
  • Synthetic lubricants have gained recent prominence in the field of lubrication because of stringent requirements of long life under extreme conditions imposed by certain new applications. These new lubricants have low pour points and desirable viscosity characteristics and can tolerate temperatures considerably above the decomposimetals under operating conditions. Dissolved metals seem phenyla-naphthylamine with an aminoquinoline, an aminopyridine, or a dipyridylamine to reduce oxidation.
  • the present invention provides an improved ester base lubricant composition containing diphenylamine and a dipyridylamine in minor amounts effective to impart increased oxidation stability to the lubricant.
  • Preferred dipyridylamines are unsubstituted compounds, preferably 2,2'-dipyridylamine and 4,4'-dipyridylamine, especially the former.
  • Each additive is advantageously present in an amount from about 0.01 to 5% by weight of the final lubricating composition, preferably 0.1 to 3% by weight of the final composition. The presence of both additives is essential to the practice of the invention.
  • the present invention provides a combination of oxidation inhibitors which is not only surprisingly superior to the individual inhibitors but which is also remarkably more effective than other known synergistic combinations of inhibitors, such as the combination of phenyl-a-naphthylamine and 2,2-dipyridylamine disclosed by Eickemeyer, cited above.
  • PAN phenyl-a-naphtl1 amine
  • DPA diphenylarnine
  • 22DPA -dipyridylamine
  • DPA+0.5 22DPA 0 .0 PAN+0.5 22DPA+O 2 to catalyze oxidative degradation of the lubricant, thereby substantially shortening its useful life.
  • Additives have traditionally been employed in small concentrations to impart resistance to oxidation to these lubricants.
  • Runs 7 to 9 and 12 to 14 illustrate that in the presence of the EP agent, the effectiveness of the combination of the invention is still further enhanced, rather than being detrimentally affected as might be expected.
  • the combination of the invention is surprisingly superior to other similar known synergistic combinations.
  • a lubricant representative of the invention was compared with one representative of the prior art in the Pratt and Whitney Type II Bearing Test.
  • the formulations were identical except that U the oil of the invention contained 1% W. diphenylamine Whereas the oil representative of the art contained 1% W. phenyl-a-naphthylamine.
  • the base oil was in each case a mixture of 67% w. pentaerythrityl tetraester of mixed C C alkanoic acids and 33% W. dipentaerythrityl hexaester of mixed C C alkanoic acids.
  • the Type II Bearing Test is employed as a final method of evaluating high-temperature synthetic lubricant prior to full scale jet engine testing. It utilizes a circulating oil system and a 100 millimeter test bearing similar to many of the bearings used in jet engines. The test is of 100 hours duration and is conducted at 440 F. tank temperature, 400 F. oil-in temperature and 500 F. bearing temperature. During the test, oil enters the bearing compartment at 0.30-0.35 ft. /min. and is scavenged with the test oil to a two-gallon test oil tank. Performance of the oil in this test is judged on the basis of resulting deposits and increase in acid number and viscosity. The results of the tests are shown in Table II below. Composition I represents the known composition (combination of PAN and 2,2'-dipyridylamine antioxidants), and Composition 11 represents an oil of the invention.
  • Suitable synthetic lubricants based on the practice of the invention are esters of alcohols having 1 to 20, especially 4 to 12 carbon atoms and aliphatic carboxylic acids having from 3 to 20, especially 4 to 12 carbon atoms, and mixtures thereof.
  • the ester base may be a simple ester (reaction product of a monohydroxy alcohol and a monocarboxylic acid), a polyester (reaction product of an alcohol and an acid, one of which has more than one functional group), or a complex ester (reaction product of a polyfunctional acid with more than one alcohol, or of a polyfunctional alcohol with more than one acid).
  • excellent synthetic lubricants may be formulated from mixtures of esters, such as major proportions of complex esters and minor amounts of diesters.
  • Monohydric alcohols suitable for making ester base stocks include methyl, butyl, isooctyl, dodecyl and octadecyl alcohols.
  • Oxo alcohols prepared by the reaction of olefins with carbon monoxide and hydrogen are suitable.
  • Neoalcohols, i.e., alcohols having no hydrogens on the beta carbon atoms are preferred. Examples of such alcohols are 2,2,4-trimethylpentanol-1 and 2,2-dimethyl propanol.
  • Polyaclohols used for the production of base oil esters preferably contain 1 to 12 carbons.
  • dialcohols are 2-ethyl-1,3-hexanediol, 2-propyl 3,3 heptanediol, 2- butyl-1,3-butanediol, 2,4-dimesityl 1,3 butanediol, and polypropylene glycols having molecular weights of from about 100 to 300.
  • Alcohols having 3, 4, 5 or more hydroxyl groups per molecule are also suitable and are preferred; examples of these polyols are pentaerythritol, dipentaerythritol, and trimethylolpropane. Mixtures of alcohols may also be used.
  • Suitable carboxylic acids for making the ester base oils include monoand di-basic aliphatic carboxylic acids.
  • appropriate acids are butyric, valeric, sebacic, azelaic, suberic, succinic, caproic, adipic, ethyl suberic, diethyl adipic, oxalic, malonic, glutaric, pentadecanedicarboxylic, diglycolic, thiodiglycolic, acetic, propionic, caprylic, lauric, palmitic, pimelic, and mixtures thereof.
  • Preferred acids are sebacic, azelaic, glutaric, adipic, and their mixtures.
  • ester base oils examples include ethyl palmitate, ethyl laurate, butyl stearate, di-(2-ethylhexyl) sebacate, di-(Z-ethylhexyl) azelate, ethyl glycol dilaurate, di-(Z- ethylhexyl) phthalate, di(l,3-methylbutyl) adipate, di- (l-ethylpropyl) azelate, diisopropyloxylate, dicyclohexyl sebacate, glycerol tri-n-heptoate, di(undecyl) azelate, and tetraethylene glycol di-(2-ethylene caproate), and mixtures thereof.
  • An especially preferred mixture of esters consists of about 50 to wt. bis(2,2,4-trimethylpentyl) azelate and 20 to 50% wt. 1,1,1,-trimethylyl
  • esters for use as base stocks in the present invention are esters of monocarboxylic acids havings 3 to 12 carbons and polyalcohols such as pentaerythritol, dipentaerythritol, and trimethylolpropane.
  • esters examples include pentaerythrityl butyrate, pentaerythrityl tetra'butyrate, pentaerythrityl tetravalerate, pentaerythrityl tetracaproate, pentaerythrityl dibutyratedicaproate, pentaerythrityl butyratecaproate divalerate, pentaerythrityl butyrate trivalerate, pentaerythrityl butyrate tricaproate, pentaerythrityl tributyratecaproate, mixed C saturated fatty acid esters of pentaerythritol, dipentaerythrityl hexavalerate, dipentaerythrityl hexacaproate, dipentaerythrityl hexaheptoate, dipentaerythrityl hexacaprylate, dipentaerythrityl tributyratecaproate, dipent
  • Ester oils may be prepared by simple reaction of the alcoholic and acidic reactants in proportions suitable for producing the desired product; preparation preferably takes place in a solvent such as an aromatic hydrocarbon, and in the presence of a catalyst, such as HCl, HF, HBr, H 80 H PO SOCl BF etc.
  • a catalyst such as HCl, HF, HBr, H 80 H PO SOCl BF etc.
  • Preparation of suitable esters is described in Eickemeyer, U.S. 3,038,859, issued June 12, 1962, and Young, U.S. 3,121,109, issued February 11, 1964.
  • compositions of the invention may also contain other additives such as El agents, VI irnprovers, anti-corrosion agents, etc., to improve other properties of the oil.
  • additives such as El agents, VI irnprovers, anti-corrosion agents, etc.
  • Composition 1 60% w. C -C acid esters of pentaerythritol 40% w. C -C acid esters of dipentaerythritol +1% W. diphenylamine +0.5 W. 2,2'-dipyridylamine +02% W. salt of mixed C C primary amines and monochloromethyl phosphonic acid (M/J 5 6 Composition IV I to 5% by Weight of dipyridylamine and .01% t0 3% by 100% W. diisooctyl azelate Weight of a mixed salt of monochloromethylphosphonic +1 0% W. diphenylamine acid and ten-0 43 alkyl primary amines. +0.5 w.
  • a lubricant composition comprising a major amount of a pentaerythrityl tetraester of Gi -C aliphatic carbox- DANIEL E WYMAN Primary Examiner ylic acids, .01% to 5% by Weight of diphenylamine, .01% P. P. GARVIN, Assistant Examiner.

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  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
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  • Organic Chemistry (AREA)
  • Lubricants (AREA)
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Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3432433A (en) * 1965-11-15 1969-03-11 Shell Oil Co Lubricant compositions
US3493511A (en) * 1966-12-28 1970-02-03 Mobil Oil Corp Organic compositions containing antioxidants
US3951829A (en) * 1975-05-05 1976-04-20 Cities Service Company Two-cycle and rotary combustion engine lubricant
US5998340A (en) * 1997-03-07 1999-12-07 Hitachi Maxell, Ltd. Lubricant and magnetic recording medium using the same

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2683691A (en) * 1951-08-18 1954-07-13 Shell Dev Extreme pressure lubricants
US2777819A (en) * 1954-04-27 1957-01-15 Shell Dev Lubricating compositions
US3115519A (en) * 1960-09-19 1963-12-24 Shell Oil Co Stable esters
US3121691A (en) * 1960-05-24 1964-02-18 Sinclair Research Inc Lubricant composition
US3226324A (en) * 1962-02-19 1965-12-28 Sinclair Research Inc Lubricant composition containing phenothiazine and dipyridylamine

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2930758A (en) * 1956-09-28 1960-03-29 Texaco Inc Ester-base lubricant containing anti-oxidant mixtures

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2683691A (en) * 1951-08-18 1954-07-13 Shell Dev Extreme pressure lubricants
US2777819A (en) * 1954-04-27 1957-01-15 Shell Dev Lubricating compositions
US3121691A (en) * 1960-05-24 1964-02-18 Sinclair Research Inc Lubricant composition
US3115519A (en) * 1960-09-19 1963-12-24 Shell Oil Co Stable esters
US3226324A (en) * 1962-02-19 1965-12-28 Sinclair Research Inc Lubricant composition containing phenothiazine and dipyridylamine

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3432433A (en) * 1965-11-15 1969-03-11 Shell Oil Co Lubricant compositions
US3493511A (en) * 1966-12-28 1970-02-03 Mobil Oil Corp Organic compositions containing antioxidants
US3951829A (en) * 1975-05-05 1976-04-20 Cities Service Company Two-cycle and rotary combustion engine lubricant
US5998340A (en) * 1997-03-07 1999-12-07 Hitachi Maxell, Ltd. Lubricant and magnetic recording medium using the same

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GB1077606A (en) 1967-08-02
DE1278662B (de) 1968-09-26

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