US2971910A - Lubricating compositions - Google Patents

Lubricating compositions Download PDF

Info

Publication number
US2971910A
US2971910A US702749A US70274957A US2971910A US 2971910 A US2971910 A US 2971910A US 702749 A US702749 A US 702749A US 70274957 A US70274957 A US 70274957A US 2971910 A US2971910 A US 2971910A
Authority
US
United States
Prior art keywords
acid
oil
carbon atoms
soluble
aliphatic
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
Application number
US702749A
Other languages
English (en)
Inventor
George M Calboun
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.)
Shell USA Inc
Original Assignee
Shell Oil Co
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
Priority to BE573900D priority Critical patent/BE573900A/xx
Priority to NL108912D priority patent/NL108912C/xx
Priority to DENDAT1075255D priority patent/DE1075255B/de
Application filed by Shell Oil Co filed Critical Shell Oil Co
Priority to US702749A priority patent/US2971910A/en
Priority to GB40329/58A priority patent/GB845628A/en
Priority to FR781779A priority patent/FR1215998A/fr
Application granted granted Critical
Publication of US2971910A publication Critical patent/US2971910A/en
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

Links

Classifications

    • 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
    • C10M159/00—Lubricating compositions characterised by the additive being of unknown or incompletely defined constitution
    • C10M159/12—Reaction products
    • 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
    • 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
    • C10M2205/02—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions containing acyclic monomers
    • 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
    • C10M2207/02—Hydroxy compounds
    • C10M2207/021—Hydroxy compounds having hydroxy groups bound to acyclic or cycloaliphatic carbon atoms
    • 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
    • C10M2207/02—Hydroxy compounds
    • C10M2207/023—Hydroxy compounds having hydroxy groups bound to carbon atoms of six-membered aromatic rings
    • 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
    • C10M2207/125—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
    • 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
    • C10M2207/125—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
    • 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
    • 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
    • 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
    • C10M2207/22—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
    • 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
    • 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
    • C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2215/02—Amines, e.g. polyalkylene polyamines; Quaternary amines
    • C10M2215/04—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to acyclic or cycloaliphatic carbon atoms
    • 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
    • C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2215/26—Amines
    • 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
    • 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 suitable lubricating oil containing a small amount of a complex obtained by admixing at a temperature ranging from about room temperature to about 85 C., approximately equivalent amounts of (1) an oil-insoluble aliphatic polycarboxylic acid, preferably an oil-insoluble aliphatic dicarboxylic acid, (2) a marginally oil-soluble high molecular weight fatty acid, preferably a C,-,-C saturated or unsaturated aliphatic monocarboxylic acid, and (3) an oil-soluble long chain aliphatic amine, preferably an oil soluble highly branched-chain aliphatic amine.
  • the oil-insoluble aliphatic polycarboxylic acids include acids such as unsubstituted aliphatic dicarboxylic acids e.g. oxalic, malonic, succinic, glutaric, adipic, pimelic, sebacic, azelaic and suberic acids, and hydroxypolycarboxylic acids e.g. tartaric and citric acids and the like.
  • These acids may contain short alkyl radicals of from 1 to 4 carbon atoms each and a total of no more than about six carbons in all such alkyl radicals, as, for instance, mono-, di-, and tri-, methylor ethylor monobutyl glutaric, adipic, pimelic or suberic acids.
  • Specific acids of this class are 2-methylglutaric acid, 2-methyladipic acid, 2-methylpimelic acid, Z-methylsuberic acid, 3-methylglutaric acid, 3-methyladipic acid, 3-methylpimelic acid, 3- methylsuberic acid, 2,2-dimethy1glutaric acid, 2,2-dimethyladipic acid, 2,3-dimethylglutaric acid, 2,3-dimethyladipic acid, 3,3-dimetbyladipic acid, 2,4-dimethyladipic acid,
  • the high molecular weight fatty acids useful for purposes of the invention are saturated and unsaturated C -C fatty acids, e.g. lauric, palmitic, myristic, stearic, oleic, linoleic, ricinoleic acids and the like.
  • the other component of the complex is an alpihatic amine which may be either a primary, secondary or tertiary, saturated or unsaturated, straight or branchedchain, aliphatic amine having at least 8 carbon atoms, preferably a saturated branched-chain aliphatic primary amine having from 12 to 24 carbon atoms.
  • the saturated straight chain aliphatic tertiary amines having 12 to 24 carbon atoms are also especially useful although the primary branched-chain amines are preferred.
  • Typical of the broad class of such amines are monoamines such as octylamine, dodecylamine, tetradecylamine, hexadecylamine, octadecylarnine, octadecenylamine, octadccadienylamine, dioctylamine, didodecylamine, dioctadecylamine, dioctadecadienylamine, lauryl dimethylamine, octadecyldimethylamine and amines derived from fatty oils or fats such as cottonseed oil, soybean oil, cocoanut oil, I lard, tallow, and the like, such as soyamine, cocoamine,
  • the tertiary alkyl primary amines containing as the tertiary alkyl radical, the radical of polyisobutylene, polypropylene and mixtures thereof are particularly effective for the purpose of the present invention. They include l,l,3,3,5,5-hexamethylhexylamine (from triisobutylene), 1,1,3,3,5,5,7,7-octamethyloctylamine (from tetraisobutylene) and 1,1,3,3,5,5,7,7,9,9-decamethyldecylamine (from pentaisobutylene) are specific preferred amines, which are suitably used individually or as mixtures thereof.
  • tertiaryalkylmethyl primary amines such as 2,2,4,4-tetramethylpentylamine, 2,2,4,4,6,6-hexamethylheptylamine and the like are suitable.
  • Other tertiaryalkyl primary amines which can be used include the C, and higher amines of this type mentioned in US. Patents 2,160,058, 2,606,923 and 2,611,782, such as tert-tridecylamine I 3 as well as isoheptyldiethylcarbinylamine, isooctylethylpropylcarbinylamine, and the like.
  • the complex is simple to prepare and involves admixing the three reactants (polycarboxylic acid, monocarboxylic acid and amine) in equivalent amounts at a temperature ranging from room temperature to about 85 C. in a non-polar medium such as a light hydrocarbon such as benzene or hydrocarbon oils. It is essential that no water or amides are formed during the formation of the complex. This is accomplished by controlling the temperature during the admixture of the above materials so that the temperature does not rise above 85 C. If during the admixing the temperature is allowed to increase above 85 C., say to 100 C. or higher, then a reaction product forms which has poor extreme pressure properties.
  • Examples of complexes useful as oil additives include equivalent weight mixtures of (l) adipic acid-lauric acid- A (2) adipic acid-lauric acid-lauryldimethylamine, (3) d-tartaric acid-lauric acid-A (4) sebacic acidlauric acid-A (5) oxalic acid-stearic acid-octadecylamine, (6) adipic acid-oleic acid-A (7) citric acidlaun'c acid-hexadecylamine, (8) azelaic acid-lauric acidoctadecylamine, (9) succinic acid-stearic acid-octadecyldimethylamine, (10) tartaric acid-oleic acid-1,1,3,3,5,5,- 7,7-octamethyloctylamine.
  • Preferred complexes are: (A) 5% adipic acid-13.7% lauric acid-13.1% A (B) 5% adipic acid-13.7% lauric acid14.6% lauryldimethylamine, (C) 5% d-tartaric acid-13.25% lauric acid-12.75% A 3.3% 2-propanol, (D) 5% sebacic acid9.9% lauric acid9.5% A
  • the materials were admixed at a temperature within the range of from room temperature to 85 C. until a homogeneous liquid formed.
  • the complex is useful in oils in amounts ranging from 0.1% to 15%, preferably from 1% to 10% by weight.
  • a small amount of from 0.1% to 5% of a clarifier e.g. an alkanol can be added to lubricants of this invention.
  • Such clarifiers include aliphatic alcohols having 2 to 18 carbon atoms per molecule, such as ethanol, propanol, hexanol or the so-called x0 alcohols derived from branched-chain olefins, such as polymers of lower alkenes of 3 to carbon atoms, and copolymers of mixtures of such alkenes, by catalyzed reaction with carbon monoxide and hydrogen in accordance with the conditions of the 0x0 process, as is well known in the art.
  • the composition of a typical C -Oxo-alcohol mixture derived from a mixture of C olefins, produced by polymerization of a typical refinery cracked gas fraction of C -C hydrocarbons is given in Table II.
  • hydrocarbon oils are petroleum motor oil (A) which is paralfinic in character and petroleum motor oil (B) which is naphthenic in character; they have the following properties:
  • the complexes of this invention are useful also for providing superior load carrying properties in lubricating oils which contain minor amounts of other agents such as silicone anti-foaming agents, alkylphenol anti-oxidants, polyacrylate ester viscosity-index improvers, and the like.
  • a lubricating composition comprising a major amount of lubricating oil and a minor amount sufficient to impart extreme pressure properties to the oil of an oilsoluble complex obtained by reacting at a temperature of from about room temperature to about C. and in equivalent amounts an oil-insoluble unsubstituted aliphatic dicarboxylic acid, said aliphatic portion of the molecule which separates the two acid groups having C carbon atoms, a marginally oil-soluble fatty acid having from 8 to 18 carbon atoms and an oil-soluble aliphatic amine having 8 to 24 carbon atoms.
  • a lubricating composition comprising a major amount of a mineral lubricating oil and a minor amount sufiicient to impart extreme pressure properties to the oil of an oil-soluble complex obtained by reacting at a temperature of from about room temperature to about 85 C. and in equivalent amounts an oil-insoluble unsubstituted aliphatic dicarboxylic acid, said aliphatic portion of the molecule which separates the two acid groups having C carbon atoms, an oil-soluble fatty acid having from 12 to 18 carbon atoms and an oil-soluble aliphatic amine having 8 to 24 carbon atoms.
  • a lubricating composition comprising a major amount of a mineral lubricating oil and a minor amount, suflicient to impart extreme pressure properties to the oil of an oil-soluble complex obtained by reacting at a temperature of from about room temperature to about 85 C. and in equivalent amounts an oil-insoluble unsubstituted aliphatic dicarboxylic acid, said aliphatic portion of the molecule which separates the two acid groups having C carbon atoms, an oil-soluble fatty acid having from 5 12 to 18 carbon atoms and an oil-soluble saturated straight-chain alkyl amine having 8-24 carbon atoms.
  • a lubricating composition comprising a major amount of a mineral lubricating oil and a minor amount, sufficient to impart extreme pressure properties to the oil of an oil-soluble complex obtained by reacting at a temperature of from about room temperature to about 85 C. and in equivalent amounts an oil-insoluble unsubstituted aliphatic dicarboxylic acid, said aliphatic portion of the molecule which separates the two acid groups having C carbon atoms, an oil-soluble fatty acid having from 12 to 18 carbon atoms and an oil-soluble saturated branched-chain alkyl amine having 12-24 carbon atoms.
  • a lubricating composition comprising a major amount of a mineral lubricating oil and a minor amount suflicient to impart extreme pressure properties to the oil of an oil-soluble complex obtained by reacting at a temperature of from about room temperature to about 85 C. and in equivalent amounts adipic acid, lauric acid and a saturated straight-chain primary aliphatic amine having 12-24 carbon atoms.
  • a lubricating composition comprising a major amount of a mineral lubricating oil and a minor amount auficient to impart extreme pressure properties to the oil of an oil-soluble complex obtained by reacting at a temperature of from about room temperature to about 85' C. and in equivalent amounts adipic acid, lauric acid and a saturated branched-chain primary aliphatic amine having 12-24 carbon atoms.
  • a lubricating composition comprising a major amount of a mineral lubricating oil and a minor amount suflicient to impart extreme pressure properties to the oil of an oil-soluble complex obtained by reacting at a temperature of from about. room temperature to about 85' C. and in equivalent amounts sebacic acid, lauric acid and a saturated branched-chain primary aliphatic amine having 12-24 carbon atoms.
  • a lubricating composition comprising a major amount of a mineral lubricating oil and a minor amount suflicient to impart extreme pressure properties to the oilof an oil-soluble complex obtained by reacting at a temperature of from about room temperature to about 85 C. and in equivalent amounts adipic acid, lauric acid and lauryldimethylamine.
  • a lubricating composition comprising a major amount of a mineral lubricating oil and a minor amount sufiicient to impart extreme pressure properties to the oil of an oil-soluble complex obtained by reacting at a temperature of from about room temperature to about 85 C. and in equivalent amounts adipic acid, lauric acid and a primary tertiary C -C alkyl amine.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Organic Chemistry (AREA)
  • Lubricants (AREA)
US702749A 1957-12-16 1957-12-16 Lubricating compositions Expired - Lifetime US2971910A (en)

Priority Applications (6)

Application Number Priority Date Filing Date Title
BE573900D BE573900A (zh) 1957-12-16
NL108912D NL108912C (zh) 1957-12-16
DENDAT1075255D DE1075255B (de) 1957-12-16 Schmieröl
US702749A US2971910A (en) 1957-12-16 1957-12-16 Lubricating compositions
GB40329/58A GB845628A (en) 1957-12-16 1958-12-15 Lubricating oil compositions
FR781779A FR1215998A (fr) 1957-12-16 1958-12-16 Huiles lubrifiantes composées

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US702749A US2971910A (en) 1957-12-16 1957-12-16 Lubricating compositions

Publications (1)

Publication Number Publication Date
US2971910A true US2971910A (en) 1961-02-14

Family

ID=24822425

Family Applications (1)

Application Number Title Priority Date Filing Date
US702749A Expired - Lifetime US2971910A (en) 1957-12-16 1957-12-16 Lubricating compositions

Country Status (6)

Country Link
US (1) US2971910A (zh)
BE (1) BE573900A (zh)
DE (1) DE1075255B (zh)
FR (1) FR1215998A (zh)
GB (1) GB845628A (zh)
NL (1) NL108912C (zh)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3203896A (en) * 1962-03-28 1965-08-31 Universal Oil Prod Co Lubricating composition
US3235495A (en) * 1962-03-12 1966-02-15 Socony Mobil Oil Co Inc Stabilized fluid silicones
US20050124507A1 (en) * 2003-12-09 2005-06-09 Watts Raymond F. Power transmission fluids with improved friction characteristics

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3506756A (en) * 1969-07-07 1970-04-14 Miles Lab Use of adipic acid as a tableting lubricant
US4446038A (en) * 1982-09-27 1984-05-01 Texaco, Inc. Citric imide acid compositions and lubricants containing the same

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2490744A (en) * 1947-02-08 1949-12-06 Socony Vacuum Oil Co Inc Antirust agent
US2594286A (en) * 1948-07-08 1952-04-29 Swan Finch Oil Corp Grease and grease base
GB750340A (en) * 1953-08-20 1956-06-13 Exxon Research Engineering Co Improvements in or relating to lubricating compositions and hydraulic fluids
US2758086A (en) * 1952-06-28 1956-08-07 California Research Corp Lubricant composition
US2788326A (en) * 1950-12-26 1957-04-09 Shell Dev Extreme pressure lubricant

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2580881A (en) * 1949-05-21 1952-01-01 Du Pont Stabilized petroleum products and stabilizing compositions
GB774085A (en) * 1952-08-19 1957-05-08 California Research Corp Polyamide grease composition
US2693448A (en) * 1952-12-30 1954-11-02 Socony Vacuum Oil Co Inc Demulsified antirust turbine oil

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2490744A (en) * 1947-02-08 1949-12-06 Socony Vacuum Oil Co Inc Antirust agent
US2594286A (en) * 1948-07-08 1952-04-29 Swan Finch Oil Corp Grease and grease base
US2788326A (en) * 1950-12-26 1957-04-09 Shell Dev Extreme pressure lubricant
US2758086A (en) * 1952-06-28 1956-08-07 California Research Corp Lubricant composition
GB750340A (en) * 1953-08-20 1956-06-13 Exxon Research Engineering Co Improvements in or relating to lubricating compositions and hydraulic fluids

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3235495A (en) * 1962-03-12 1966-02-15 Socony Mobil Oil Co Inc Stabilized fluid silicones
US3203896A (en) * 1962-03-28 1965-08-31 Universal Oil Prod Co Lubricating composition
US20050124507A1 (en) * 2003-12-09 2005-06-09 Watts Raymond F. Power transmission fluids with improved friction characteristics
EP1541665A1 (en) * 2003-12-09 2005-06-15 Infineum International Limited Power transmission fluids with improved friction characteristics
JP2005171254A (ja) * 2003-12-09 2005-06-30 Infineum Internatl Ltd 摩擦特性が向上したパワートランスミッション液
AU2004237832B2 (en) * 2003-12-09 2010-01-28 Infineum International Limited Power transmission fluids with improved friction characteristics

Also Published As

Publication number Publication date
NL108912C (zh)
DE1075255B (de) 1960-02-11
BE573900A (zh)
FR1215998A (fr) 1960-04-21
GB845628A (en) 1960-08-24

Similar Documents

Publication Publication Date Title
US3224971A (en) Borate esters and lubricant compositions containing said esters
US3180832A (en) Oil compositions containing anti-wear additives
US2403067A (en) Anticorrosion composition
US3185644A (en) Lubricating compositions containing amine salts of boron-containing compounds
US3169923A (en) Oil of lubricating viscosity
US4978465A (en) Sulfurized metalworking lubricants derived from modified natural fats and oils and formulations
US4891161A (en) Cold rolling mill lubricant
US3260671A (en) Amide oxidation inhibitor for lubricants
US3203895A (en) Lubricating oils containing amine salts of phosphates
US2560202A (en) Rust inhibiting composition
GB781341A (en) Lubricating compositions
US4557846A (en) Lubricating oil compositions containing hydroxamide compounds as friction reducers
US2971910A (en) Lubricating compositions
US3484374A (en) Stabilization or organic substances
US3000824A (en) Lubricating oil composition
US3281358A (en) Hydrocarbon compositions containing anti-wear additives
US3071544A (en) Emulsifiable mixtures of mineral oil and esters
US3182020A (en) Stabilized calcium acetate oil dispersions
US2892784A (en) Oxidation resistant lubricant compositions
US3920567A (en) Novel oxazoline-alkyl acid phosphate adducts useful as ashless antiwear additives
US3203896A (en) Lubricating composition
US3502581A (en) Antioxidant composition and use thereof
US3422017A (en) Lubricant compositions containing amine salts
US3337457A (en) Crankcase lubricants comprising a mineral and synthetic ester oil blend
US3565926A (en) Amine salts of perhalogenated monobasic carboxylic acids