US2994662A - Lubricating compositions - Google Patents

Lubricating compositions Download PDF

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Publication number
US2994662A
US2994662A US699919A US69991957A US2994662A US 2994662 A US2994662 A US 2994662A US 699919 A US699919 A US 699919A US 69991957 A US69991957 A US 69991957A US 2994662 A US2994662 A US 2994662A
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United States
Prior art keywords
acid
oil
lubricating oil
mineral
radical
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired - Lifetime
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US699919A
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English (en)
Inventor
George M Calhoun
William A Hewett
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Shell USA Inc
Original Assignee
Shell Oil Co
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Filing date
Publication date
Priority to BE573460D priority Critical patent/BE573460A/xx
Priority to NL233837D priority patent/NL233837A/xx
Priority to NL110620D priority patent/NL110620C/xx
Priority to US699919A priority patent/US2994662A/en
Application filed by Shell Oil Co filed Critical Shell Oil Co
Priority to US753882A priority patent/US3041284A/en
Priority to GB38649/58A priority patent/GB863339A/en
Priority to DEN15921A priority patent/DE1104103B/de
Priority to FR780500A priority patent/FR1217730A/fr
Application granted granted Critical
Publication of US2994662A publication Critical patent/US2994662A/en
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

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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
    • C10M1/00—Liquid compositions essentially based on mineral lubricating oils or fatty oils; Their use as lubricants
    • C10M1/08—Liquid compositions essentially based on mineral lubricating oils or fatty oils; Their use as lubricants with additives
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2203/00—Organic non-macromolecular hydrocarbon compounds and hydrocarbon fractions as ingredients in lubricant compositions
    • C10M2203/06—Well-defined aromatic compounds
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2203/00—Organic non-macromolecular hydrocarbon compounds and hydrocarbon fractions as ingredients in lubricant compositions
    • C10M2203/10—Petroleum or coal fractions, e.g. tars, solvents, bitumen
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2205/00—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2205/00—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions
    • C10M2205/14—Synthetic waxes, e.g. polythene waxes
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2205/00—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions
    • C10M2205/16—Paraffin waxes; Petrolatum, e.g. slack wax
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    • C10M2205/00—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions
    • C10M2205/17—Fisher Tropsch reaction products
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    • C10M2207/02—Hydroxy compounds
    • C10M2207/021—Hydroxy compounds having hydroxy groups bound to acyclic or cycloaliphatic carbon atoms
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    • C10M2207/021—Hydroxy compounds having hydroxy groups bound to acyclic or cycloaliphatic carbon atoms
    • C10M2207/022—Hydroxy compounds having hydroxy groups bound to acyclic or cycloaliphatic carbon atoms containing at least two hydroxy groups
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    • C10M2207/027—Neutral salts thereof
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    • C10M2207/04—Ethers; Acetals; Ortho-esters; Ortho-carbonates
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    • 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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    • C10M2207/10—Carboxylix acids; Neutral salts thereof
    • C10M2207/12—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms
    • C10M2207/125—Carboxylix 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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    • C10M2207/128—Carboxylix 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 containing hydroxy groups; Ethers thereof
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    • C10M2207/283—Esters of polyhydroxy compounds
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    • C10M2207/286—Esters of polymerised unsaturated acids
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    • C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
    • C10M2219/08—Thiols; Sulfides; Polysulfides; Mercaptals
    • C10M2219/082—Thiols; Sulfides; Polysulfides; Mercaptals containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms
    • C10M2219/084—Thiols; Sulfides; Polysulfides; Mercaptals containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms containing hydroxy groups; Derivatives thereof
    • 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
    • C10M2219/08—Thiols; Sulfides; Polysulfides; Mercaptals
    • C10M2219/082—Thiols; Sulfides; Polysulfides; Mercaptals containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms
    • C10M2219/085—Thiols; Sulfides; Polysulfides; Mercaptals containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms containing carboxyl groups; Derivatives thereof
    • 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
    • C10M2229/02—Unspecified siloxanes; Silicones
    • 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
    • C10M2229/05—Siloxanes with specific structure containing atoms other than silicon, hydrogen, oxygen or carbon
    • 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

  • This invention relates to lubricants, particularly those useful for lubrication under severe operating conditions, such as under extreme high speed and at high temperatures.
  • R is an oil-solubilizing hydrocarbyl radical, preferably a C C alkyl radical
  • R is hydrogen or a short alkyl radical of from 1 to 4 carbon atoms
  • Y is an oxygen-containing radical such as -COOX, OH, etc., preferably COOH or OH
  • X is hydrogen or a hydrocarbyl radical
  • m is an integer of at least 7
  • n is an integer of from 1 to 4, preferably Land at least one of the Y groups or -COOR' carboalkoxy being a carboxylic acid or carboxy (-COOH) radical.
  • mercapto acid or ester has the formula HSR"COOR' wherein R" is an .alkylene radical of not more than 4 carbon atoms, e.g. mercaptoacetic acid, alphaand betamercaptopropionic acid, .alpha-, betaand gamma-mercaptobutyric acid and O-mercaptovaleric acid, methyl or ethyl mercapto acetate, propionat'e or butyrate.
  • R" is an .alkylene radical of not more than 4 carbon atoms, e.g. mercaptoacetic acid, alphaand betamercaptopropionic acid, .alpha-, betaand gamma-mercaptobutyric acid and O-mercaptovaleric acid, methyl or ethyl mercapto acetate, propionat'e or butyrate.
  • the unsaturated long-chain acidic compound may be a longchain unsaturated fatty acid, e.g.
  • oleic acid linoleic acid, linolenic acid, erucic acid, ricinoleic acid or an unsaturated fatty alcohol, e.g. oleyl alcohol, 'ricinoleyl alcohol, *etc.
  • unsaturated fatty alcohol e.g. oleyl alcohol, 'ricinoleyl alcohol, *etc.
  • these compounds can be used in the form of their esters, e.g. methyl or ethyl oleate, lauryl oleate, glycerol trioleate or the like.
  • Suitable initiators include various free radicalyielding initiators, for example, various organic peroxides,
  • aliphatic, aromatic, heterocyclic and alicyclic peroxides such as diethyl peroxide, tertiary butyl hydroperoxide, dibenzoyl peroxide, ditertbutyl peroxide, dimethylthienyl peroxide, dicyclohexyl peroxide, dilauroyl peroxide and urea peroxide.
  • suitable organic peroxides such as diethyl peroxide, tertiary butyl hydroperoxide, dibenzoyl peroxide, ditertbutyl peroxide, dimethylthienyl peroxide, dicyclohexyl peroxide, dilauroyl peroxide and urea peroxide.
  • initiating compounds known include emulsion redox systems, such as a mixture of sodium bisulfite and persulfate, ammonium persulfate, alkali metal perborates, azo compounds, such as alpha,alpha-azodiisobutyronitrile, etc.
  • EXAMPLE I About 600 grams of oleic acid and 223.5 grams of mercapto-acetic acid were mixed in a flask at 20-25" C. About 240 drops (30 drops at a time) of t-butyl hydroperoxide were added over a period of 2 hours and the temperature was kept at about 37 C. The reaction mixture was diluted with 2 volumes of diethyl ether, washed with 12 liters of water to pH 4, dried over Na SO filtered and the solvent stripped at 155 C. and 2 mm. pressure. The final product was a mixture of 9- and 10-carboxymethylmercaptostearic acid and analysis of the product was as follows:
  • the final product was a mixture of glyceryl tris(9- and 10-carboxymethylmercaptostearate) and the equivalent weight of the product was found to be 445 (theory EXAMPLE V
  • About 240 drops (30 drops at a time) of t-butyl hydro- .peroxide were'added over a period of 2 hours and the temperature was kept at about 37 C.
  • the reaction ' ⁇ mixture was diluted with 2 volumes of diethyl ether,
  • the final product was a mixture of 9- and lO-carboxymethylmercaptostearyl alcohol. a
  • the 'mercapto-modified acids or alcohols in general are oil-soluble and can be used in amounts of from about 0.5% to about 20%, preferably fromabout 1% to about 5% by weight.
  • these mercapto-modified j acids or alcohols are oil-soluble some of them form opaque solutions which can be overcome and the solutions rendered transparent by addition to oils containing 'these mercapto products a small amount (01-10%) of an oil-soluble branched-chain aliphatic monohydric alcohol, oil-soluble high molecular weight fatty acid or monoester of said fatty acid and polyhydr'ic alcohols.
  • the alcohols, fatty acids or monoesters can elfectively clarify oils containing mercapto acids or alcohols or derivatives thereof as described without destroying the extreme pressure properties of such oil compositions.
  • the oil-soluble alkanols particularlyuseful as clarifiers are the so-called 0x0 alcohols derived from branched-chain olefins, such as polymers of lower alkenes Table 1 Alcohol Percent, wt.
  • alkanols include 6-methyl-1- heptanol, 2-n-propyl-1-pentanol, 3-n-propyl-l-hexanol, -2,2-dimethyl-1-octanol, 10,10-dimethyl-1-undecanol, 3- isopropyl1-heptanol and mixtures thereof.
  • the fatty acids useful as clarifiers include the saturated 4 to 30 carbon atoms such as capric, lauric, oleic, linoleic, ricinoleic acids and mixtures thereof.
  • the monoesters derived from simple alkane polyols and long chain fatty acids useful as clarifiers include oil-soluble glycerol monooleate, glycerol monostearate, glycerol monoricinoleate, pentaerythritol monoand dilaurate, pentaerythritol monoand dioleate, pentaerythritol monoand distearate, mono, di-, and triethylene glycol monooleate, propylene glycol monoricinoleate, triethylene glycol monostearate, sorbitol monolaurate, mannitol monooleate, mannitol dioleate, sorbitol dioleate, etc.
  • the lubricating oils used in compositions of this invention can be a variety of synthetic or natural hydrocarbon oils having a viscosity-range of from 50 SUS at 100 F. to 250 SUS at 210 F. (SAE viscosity number ranging from SAE 5 to SAE
  • the natural hydrocarbon oils can be obtained from paraflinic, naphthenic, asphaltic or mixed base crudes, and/or mixtures thereof.
  • Synthetic oils include polymerized olefins, alkylated aromatics, isomerized waxes, copolymers of alkylene glycols and alkylene .oxide (Ucon fluids) which are described in US.
  • Patents 2,425,755, 2,425,845 and 2,774,733 such as Ucon -50HB170, Ucon 50HB660 or Ucon LB550X and which are copolymerts of ethylene and 1,2-propylene oxides the mono and diols as well as their ether derivatives; organic esters of an aliphatic dibasic acid such as di-Z-ethyl hexyl sebacate or di-Z-ethyl hexyl adipate and the like.
  • hydrocarbon oils may be blended with fixed oils such as castor oil, lard oil and the like and/ or 30v synthetic oils as mentioned or silicone polymers and the like.
  • fixed oils such as castor oil, lard oil and the like and/ or 30v synthetic oils as mentioned or silicone polymers and the like.
  • Typical oils of this type are petroleum motor oils (A) which is paraffinic in character and (B) which is naphthenic in character having the following properties:
  • composition A Percent Example I additive 2 Q1010 mineral oil Balance Composition B:
  • Example IV additive 2 5 Glycerol monooleate 5 1010 mineral oil Balance Composition E:
  • Example V additive 2 C H OH (made by 0x0 process) 3.5 v l010minera1 oil -.Ba1au,ce
  • Composition G is a composition of Composition G:
  • Example I additive 2 Di-Z-ethylhexyl sebacate Balance Compositions of this invention were evaluated for their extreme pressure properties on a Spur-Gear machine.
  • the machine consists essentially of two geometrically similar pairs of gears connected by two parallel shafts.
  • the gear pairs are placed in separate gear boxes, which also contain the supporting ball bearings.
  • One of the shafts consists of two sections connected by a coupling. Loading is accomplished by locking one side of the coupling and applying torque to the other.
  • the conditions of the test were:
  • the data show the outstanding enhancement of the load-carrying ability of the oil effected by the mercaptocontaining acids of the invention, as represented by those of Compositions A through F.
  • malonic acid, succinic acid, 3-hexadecyl adipic acid and C -alkenyl succinic acid as well as sulfur-containing acid outside the scope used by applicants such as thiodiglycolic acid, thio-alpha,alpha'bis(stearic acid), dodecylmercaptosuccinic acid, heptylmercaptosuccinic acid, alpha-mercaptobenzoic acid, glycerolmonooleate, lauric acid or Oxo" alcohol effected only a slight improvement.
  • the sulfur-containing acids of this invention are useful also for providing superior load-carrying properties in lubricating oils which contain minor amounts of other agents which are non-reactive with the dicarboxylic acids, such as silicone anti-foaming agents, alkylphenol antioxidants, polyacrylate ester viscosity-index improvers, and the like.
  • a lubricating oil composition comprising a major 75 amount of mineral lubricating oil and from about 1% to 5% of a sulfur-containing carboxylic acid having the formula S-(CHah-COOR wherein R is an 'oil-solubilizing alkyl radical having from 8 to carbon atoms, R is selected from the group consisting of hydrogen and a C -C alkyl radical, Y is an oxygen-containing radical selected from the group consisting of OH and COOX where X is selected from the group consisting of hydrogen and a hydrocarbyl radical, m is an integer of from 7 to 10 and n is an integer of from 1 to 4, one of the oxygen-containing groups being a carboxy radical.
  • a mineral lubricating oil composition comprising a major amount of mineral lubricating oil and from about 1% to 5% of a carboxy C alkyl mercapto-substituted long chain fatty acid, said carboxy C alkyl mercapto radical being from 7 to 10 carbon atoms away from the carboxyl radical of the fatty acid.
  • a mineral lubricating oil composition comprising a major amount of mineral lubricating oil and from about 1% to 5% of a carboxy C alkyl mercapto-substituted long chain fatty alcohol, said carboxy C alkyl mercapto radical being from 7 to 10 carbon atoms away from the hydroxyl radical of the fatty alcohol.
  • a mineral lubricating oil composition comprising a major amount of mineral lubricating oil and from about 1% to 5% of a carboxy C alkyl mercapto-substituted ester of a long chain fatty acid, said carboxy C alkyl mercapto radical being from 7 to 10 carbon atoms away from the ester group.
  • a mineral lubricating oil composition comprising a major amount of mineral lubrication oil and from about 1% to 5% of a carboxy methyl mercapto-substituted long chain fatty acid, said methyl mercapto radical being from 7 to 10 carbon atoms away from the carboxyl radical of the fatty acid.
  • the lubricating oil composition of claim 1 containing from about 0.1% to about 10% of an oil-soluble monoester of a fatty acid having 1030 carbon atoms and a glycerol.
  • the lubricating oil composition of a claim 1 containing from about 0.1% to about 10% of an oil-soluble branched-chain OX0 alcohol.
  • the lubricating oil composition of claim 1 containing from about 0.1% to about 10% of an oil-soluble long-chain fatty acid having '10-30 carbon atoms.
  • a mineral lubricating oil composition comprising a major amount of mineral lubricating oil and from about 11% to 5% of 9- and 10-carboxymethylmercaptostearic acid.
  • a mineral lubricating oil composition comprising a major amount of mineral lubricating oil and from about 1% to about 5% of 9- and 10-carboxymethylmercapto-Z-hydroxystearic acid.
  • a mineral lubricating oil composition comprising a major amount of mineral lubricating oil and from about 1% to about 5% of glyceryl tris(9- and l0-carboxymercaptostearate.
  • a mineral lubricating oil composition comprising a major amount of mineral lubricating oil and. from about 1% to about 5% of 9- and lO-carboxymethylmercaptostearyl alcohol.
  • the lubricating oil composition of claim 9 containing from about 0.1% to about 10% of glycerol monooleate.
  • the lubricating oil composition of claim 9 containing from about 0.1% to about 10% of lauric acid.
  • the lubricating oil composition of claim 9 containing from about 0.1% to about 10% of an oil-soluble branched-chain 0x0 alcohol.
  • the lubricating oil composition of claim 9 containing from about 0. 1% to about 10% of glycerol 7 monooleate.
  • the lubricating composition of claim 12 containing from about 0.1% to about 10% of an oil-soluble branched-chain 0x0 alcohol.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Lubricants (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
US699919A 1957-12-02 1957-12-02 Lubricating compositions Expired - Lifetime US2994662A (en)

Priority Applications (8)

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BE573460D BE573460A (is") 1957-12-02
NL233837D NL233837A (is") 1957-12-02
NL110620D NL110620C (is") 1957-12-02
US699919A US2994662A (en) 1957-12-02 1957-12-02 Lubricating compositions
US753882A US3041284A (en) 1957-12-02 1958-08-08 Lubricating compositions
GB38649/58A GB863339A (en) 1957-12-02 1958-12-01 Lubricating oil compositions
DEN15921A DE1104103B (de) 1957-12-02 1958-12-01 Hochdruckzusatzstoff fuer Schmieroele
FR780500A FR1217730A (fr) 1957-12-02 1958-12-01 Composition d'huile lubrifiante

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US699919A US2994662A (en) 1957-12-02 1957-12-02 Lubricating compositions

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DE (1) DE1104103B (is")
FR (1) FR1217730A (is")
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Cited By (14)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3112268A (en) * 1960-02-15 1963-11-26 Shell Oil Co Lubricating oil composition
US3189547A (en) * 1959-07-03 1965-06-15 Shell Oil Co Lubricating compositions
US3198737A (en) * 1960-12-23 1965-08-03 Shell Oil Co Lubricating compositions and additives therefor
US3400139A (en) * 1959-07-03 1968-09-03 Shell Oil Co Sulfides of higher fatty acids
US4129510A (en) * 1976-04-28 1978-12-12 The Lubrizol Corporation Sulfur-containing compounds and lubricants and fuels containing them
US4519925A (en) * 1976-04-28 1985-05-28 The Lubrizol Corporation Sulfur-containing compounds and lubricants containing them
US4552893A (en) * 1983-03-07 1985-11-12 Smithkline Beckman Corporation Leukotriene antagonists
US4696946A (en) * 1985-08-30 1987-09-29 Schering Corporation Topical Treatment of hyperproliferative skin diseases
US4758594A (en) * 1984-07-18 1988-07-19 Schering Corporation Inhibitors of slow reacting substance of anaphylaxis
US4798842A (en) * 1984-07-18 1989-01-17 Schering Corporation Inhibitors of slow reacting substance of anaphylaxis
US4889873A (en) * 1984-07-18 1989-12-26 Schering Corporation Inhibitors of slow reacting substance of anaphylaxis
US4988716A (en) * 1984-07-18 1991-01-29 Schering Corporation Inhibitors of slow reacting substance of anaphylaxis
EP1833950A4 (en) * 2004-12-21 2009-02-25 Exxonmobil Res & Eng Co NON-DANGEROUS ASH-FREE WEAR PROTECTION ADDITIVE CONTAINING HIGH QUALITY WEAR-RESISTANT LUBRICANT
WO2017072343A1 (fr) * 2015-10-29 2017-05-04 Pivert Nouveaux polymères soufrés ramifiés

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4031023A (en) * 1976-02-19 1977-06-21 The Lubrizol Corporation Lubricating compositions and methods utilizing hydroxy thioethers
FR2962131B1 (fr) * 2010-06-30 2013-10-18 Centre Nat Rech Scient Procede de fonctionnalisation de corps gras d'origine naturelle

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2317666A (en) * 1940-05-08 1943-04-27 Alox Corp Lubrication composition
US2449996A (en) * 1945-11-28 1948-09-28 Goodrich Co B F Preparation of sulfur containing dicarboxylic acids
US2459717A (en) * 1946-01-23 1949-01-18 Shell Dev Organic lubricant composition
US2644793A (en) * 1950-08-30 1953-07-07 Standard Oil Dev Co Rust inhibiting composition
US2737525A (en) * 1951-11-13 1956-03-06 John F Mulvaney Tricarboxylic acid esters

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2317666A (en) * 1940-05-08 1943-04-27 Alox Corp Lubrication composition
US2449996A (en) * 1945-11-28 1948-09-28 Goodrich Co B F Preparation of sulfur containing dicarboxylic acids
US2459717A (en) * 1946-01-23 1949-01-18 Shell Dev Organic lubricant composition
US2644793A (en) * 1950-08-30 1953-07-07 Standard Oil Dev Co Rust inhibiting composition
US2737525A (en) * 1951-11-13 1956-03-06 John F Mulvaney Tricarboxylic acid esters

Cited By (15)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3189547A (en) * 1959-07-03 1965-06-15 Shell Oil Co Lubricating compositions
US3400139A (en) * 1959-07-03 1968-09-03 Shell Oil Co Sulfides of higher fatty acids
US3112268A (en) * 1960-02-15 1963-11-26 Shell Oil Co Lubricating oil composition
US3198737A (en) * 1960-12-23 1965-08-03 Shell Oil Co Lubricating compositions and additives therefor
US4129510A (en) * 1976-04-28 1978-12-12 The Lubrizol Corporation Sulfur-containing compounds and lubricants and fuels containing them
US4519925A (en) * 1976-04-28 1985-05-28 The Lubrizol Corporation Sulfur-containing compounds and lubricants containing them
US4552893A (en) * 1983-03-07 1985-11-12 Smithkline Beckman Corporation Leukotriene antagonists
US4758594A (en) * 1984-07-18 1988-07-19 Schering Corporation Inhibitors of slow reacting substance of anaphylaxis
US4798842A (en) * 1984-07-18 1989-01-17 Schering Corporation Inhibitors of slow reacting substance of anaphylaxis
US4889873A (en) * 1984-07-18 1989-12-26 Schering Corporation Inhibitors of slow reacting substance of anaphylaxis
US4988716A (en) * 1984-07-18 1991-01-29 Schering Corporation Inhibitors of slow reacting substance of anaphylaxis
US4696946A (en) * 1985-08-30 1987-09-29 Schering Corporation Topical Treatment of hyperproliferative skin diseases
EP1833950A4 (en) * 2004-12-21 2009-02-25 Exxonmobil Res & Eng Co NON-DANGEROUS ASH-FREE WEAR PROTECTION ADDITIVE CONTAINING HIGH QUALITY WEAR-RESISTANT LUBRICANT
WO2017072343A1 (fr) * 2015-10-29 2017-05-04 Pivert Nouveaux polymères soufrés ramifiés
FR3043086A1 (fr) * 2015-10-29 2017-05-05 Pivert Nouveaux polymeres soufres ramifies

Also Published As

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NL110620C (is")
NL233837A (is")
DE1104103B (de) 1961-04-06
BE573460A (is")
FR1217730A (fr) 1960-05-05
GB863339A (en) 1961-03-22

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