US3773665A - Lubricants containing amine antioxidants - Google Patents

Lubricants containing amine antioxidants Download PDF

Info

Publication number
US3773665A
US3773665A US00199732A US3773665DA US3773665A US 3773665 A US3773665 A US 3773665A US 00199732 A US00199732 A US 00199732A US 3773665D A US3773665D A US 3773665DA US 3773665 A US3773665 A US 3773665A
Authority
US
United States
Prior art keywords
naphthylamine
composition
substituted
mixture
lubricant
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
US00199732A
Other languages
English (en)
Inventor
M Braid
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.)
Mobil Oil AS
ExxonMobil Oil Corp
Original Assignee
Mobil Oil AS
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Mobil Oil AS filed Critical Mobil Oil AS
Application granted granted Critical
Publication of US3773665A publication Critical patent/US3773665A/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
    • 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
    • C10M133/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing nitrogen
    • C10M133/02—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing nitrogen having a carbon chain of less than 30 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
    • C10M133/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing nitrogen
    • C10M133/02—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing nitrogen having a carbon chain of less than 30 atoms
    • C10M133/04—Amines, e.g. polyalkylene polyamines; Quaternary amines
    • C10M133/12—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to a carbon atom of a six-membered aromatic 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
    • 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
    • C10M2205/02—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
    • 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
    • C10M2205/022—Ethene
    • 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
    • C10M2205/026—Butene
    • 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
    • C10M2205/028—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions containing acyclic monomers containing aliphatic monomers having more than four 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
    • 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
    • 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
    • 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
    • C10M2207/282—Esters of (cyclo)aliphatic oolycarboxylic 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
    • C10M2207/283—Esters of polyhydroxy 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
    • 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
    • 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
    • C10M2207/34—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
    • 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
    • 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
    • C10M2209/04—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds containing monomers having an unsaturated radical bound to an alcohol or ester thereof; bound to an aldehyde, ketonic, ether, ketal or acetal radical
    • 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
    • C10M2209/06—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds containing monomers having an unsaturated radical bound to an acyloxy radical of saturated carboxylic or carbonic acid
    • 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
    • C10M2209/06—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds containing monomers having an unsaturated radical bound to an acyloxy radical of saturated carboxylic or carbonic acid
    • C10M2209/062—Vinyl esters of saturated carboxylic or carbonic acids, e.g. vinyl acetate
    • 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
    • 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
    • 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
    • C10M2209/109—Polyethers, i.e. containing di- or higher polyoxyalkylene groups esterified
    • 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
    • C10M2215/06—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
    • 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
    • C10M2215/18—Containing nitrogen-to-nitrogen bonds, e.g. hydrazine
    • C10M2215/182—Azo 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
    • 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
    • C10N2050/00—Form in which the lubricant is applied to the material being lubricated
    • C10N2050/10—Form in which the lubricant is applied to the material being lubricated semi-solid; greasy

Definitions

  • This invention relates to lubricant compositions having improved antioxidant characteristics. More particularly, the invention relates to lubricants to which have been added a combination of additives which imparts antioxidant properties thereto.
  • Lubricating oils and greases are subject to oxidative deterioration at elevated temperatures or upon prolonged exposure in an ordinary atmosphere. Such deterioration is in many instances evidenced by an increase in acidity and in viscosity, and when the deterioration is severe enough it can cause metal parts to corrode. Additionally, there is a loss of lubricating properties which may lead to complete failure of the part or parts in contact with the oil. Numerous additives have been tried as antioxidants in lubricants, but many of them are only marginally effective except at the higher concentrations.
  • amines as lubricant antioxidants
  • U.S. Pat. No. 3,126,344 discloses the use of such amines as phenyl-anaphthylamine, p-amino diphenylamine and p,p'-dioctyldiphenylamine as antioxidants in synthetic ester lubricating oils.
  • Representative of other patents disclosing the use of single amines are U.S. Pat. No. 3,231,499 and U.S. Pat. No. 3,309,314.
  • the invention provides a lubricant composition comprising a major proportion ofa lubricant and an antioxidant amount of a mixture comprising p,p'-dioctyl diphenylamine and a substituted naphthylamine.
  • the substituted naphthylamine useful as one component of the amine mixture has the formula where R is an alkyl group having from about 4 to about carbon atoms or a nitro group, Ar is phenyl or naphthyl, R is hydrogen or a phenylazo group, 1 is O to 2 cant.
  • R is an alkyl group having from about 4 to about carbon atoms or a nitro group
  • Ar is phenyl or naphthyl
  • R is hydrogen or a phenylazo group
  • 1 is O to 2 cant.
  • the lubricants which may be improved by the addition thereto of the above-mentioned amine mixtures are mineral oils, both paraffinic and naphthenic, synthetic oils, and greases made from these oils.
  • the syn thetic oils include polyolefin fluids, polyglycols, polyacetals, the siloxanes and the like. Especially useful are those synthetic esters which are becoming more and more popular, particularly in aviation.
  • esters made from polycarboxylic acids and monohydric alcohols such as those obtained by reacting methanol, ethanol, propanol, butanol, neopentyl alcohol and the like with pimelic acid, azelaic acid, adipic acid and the like, or from polyhydric alcohols and monocarboxylic acids.
  • preferred members are those made from trimethylol alkanes, where alkane includes ethane, propane and butane, pentaerythritol, diand tripentaerythritol, or mixtures thereof and an aliphatic monocarboxylic acid containing from 1 to about 20 carbon atoms or a mixture of such acids.
  • the polyolefin fluids contemplated are those prepared from monoolefins having from about 4 to about 22 carbon atoms. Preferred are the trimers and tetramers of decene-l.
  • the reaction mixture was allowed to warm to room temperature after the addition was completed and was further diluted with water.
  • the gray solids which separated were collected, treated with ammonia in methanol suspension, and recrystallized from ethanol.
  • the N-( 4-tert-octylphenyl )-4-phenylazol -naphthylamine was obtained as a red crystalline solid melting at l35-137 C.
  • test composition A sample of the test composition was heated and air at the rate of about 5 liters per hour was passed through for a period of about 24 hours at 450 F.
  • Present in the test sample were specimens of iron, copper, aluminum, and lead.
  • the metals are typical metals of engine or machine construction, and they also provide some catalysis for the oxidation of organic materials.
  • the results are tabulated in the following table.
  • the change in kinematic viscosity, measured in centistokes at 100 F. KV change) and the change in the neutralization number (NN change) are measures of the effectiveness of an antioxidant in lubricants.
  • substituted naphthylamines useful in the mixtures of this invention are the following.
  • a lubricant composition comprising a major proportion of a lubricant and an antioxidant amount of a mixture comprising p, p-dioctyldiphenylamine and a substituted naphthylamine of the formula wherein R is N0 or an alkyl of from 4 to 20 carbon atoms, Ar is phenyl or naphthyl, R is hydrogen or phenylazo, R being hydrogen when R is nitro and x is l or 2.
  • composition of claim 1 wherein the mixture comprises from about 0.002% to about 10% by weight thereof.
  • composition of claim 1 wherein the lubricant is a lubricating oil or grease.
  • composition of claim 5 wherein the lubricating oil is a synthetic ester lubricating oil.
  • composition of claim 1 wherein the substituted naphthylamine is N-(4-tert-octylphenyl)-4- phenylazol -naphthylamine.
  • composition of claim 1 wherein thesubstituted naphthylamine is l,l-dinaphthylamine.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Organic Chemistry (AREA)
  • Lubricants (AREA)
US00199732A 1971-11-17 1971-11-17 Lubricants containing amine antioxidants Expired - Lifetime US3773665A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US19973271A 1971-11-17 1971-11-17

Publications (1)

Publication Number Publication Date
US3773665A true US3773665A (en) 1973-11-20

Family

ID=22738782

Family Applications (1)

Application Number Title Priority Date Filing Date
US00199732A Expired - Lifetime US3773665A (en) 1971-11-17 1971-11-17 Lubricants containing amine antioxidants

Country Status (9)

Country Link
US (1) US3773665A (enrdf_load_stackoverflow)
JP (1) JPS5232361B2 (enrdf_load_stackoverflow)
AU (1) AU470026B2 (enrdf_load_stackoverflow)
CA (1) CA976539A (enrdf_load_stackoverflow)
DE (1) DE2233542C3 (enrdf_load_stackoverflow)
FR (1) FR2160368B1 (enrdf_load_stackoverflow)
GB (2) GB1400178A (enrdf_load_stackoverflow)
IT (1) IT968798B (enrdf_load_stackoverflow)
NL (1) NL164895C (enrdf_load_stackoverflow)

Cited By (16)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3879307A (en) * 1973-05-18 1975-04-22 Mobil Oil Corp Organic compositions containing synergistic antioxidant mixtures
US4245939A (en) * 1978-12-13 1981-01-20 F. Jos. Lamb Company Method and apparatus for machining spherical combustion chambers
US4770802A (en) * 1986-02-04 1988-09-13 Nippon Oil Co., Ltd. Lubricating oil compositions
US5073278A (en) * 1988-07-18 1991-12-17 Ciba-Geigy Corporation Lubricant composition
US5102567A (en) * 1990-06-25 1992-04-07 Amoco Corporation High performance food-grade lubricating oil
US5273669A (en) * 1988-07-18 1993-12-28 Ciba-Geigy Corporation Lubricant composition
WO1995017488A3 (en) * 1993-12-15 1995-07-20 Exxon Research Engineering Co Lubricant composition containing a polymeric antioxidant
US5489711A (en) * 1994-12-20 1996-02-06 The B. F. Goodrich Company Synthetic lubricant antioxidant from monosubstituted diphenylamines
US5714441A (en) * 1996-07-12 1998-02-03 Exxon Research And Engineering Company Additive combination to reduce deposit forming tendencies and improve antioxidancy of aviation turbine oils
US5730906A (en) * 1996-07-12 1998-03-24 Exxon Research And Engineering Company Additive combination to reduce deposit forming tendencies and improve antioxidancy of aviation turbine oils (Law406)
US5856280A (en) * 1996-07-12 1999-01-05 Exxon Research And Engineering Company Sulfur-containing carboxylic acid derivatives to reduce deposit forming tendencies and improve antioxidancy of aviation turbine oils
US6426324B1 (en) * 1993-12-15 2002-07-30 Noveon Ip Holdings Corp. Lubricant composition
WO2003048281A1 (en) * 2001-11-29 2003-06-12 Crompton Corporation Viscosity growth inhibition in oil additive concentrates
US7307049B1 (en) * 2007-02-08 2007-12-11 Anderol, Inc. Antioxidants for synthetic lubricants and methods and manufacture
US20080045425A1 (en) * 2006-08-15 2008-02-21 Dibella Eugene P Antioxidants and Methods of Making Antioxidants
CN114479986A (zh) * 2020-10-27 2022-05-13 中国石油化工股份有限公司 抗氧剂组合物及其制备方法

Families Citing this family (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2231739B1 (enrdf_load_stackoverflow) * 1973-05-29 1980-04-04 Exxon Research Engineering Co
ZA774076B (en) * 1976-07-30 1978-05-30 Uniroyal Inc Liquid antioxidants having improved solubility in lubricating oils
JPS53128515U (enrdf_load_stackoverflow) * 1977-03-17 1978-10-12
JP5379345B2 (ja) * 2006-07-06 2013-12-25 Ｊｘ日鉱日石エネルギー株式会社 潤滑油組成物
EP2423298A1 (en) 2006-07-06 2012-02-29 Nippon Oil Corporation Compressor oil composition
US7683017B2 (en) * 2007-06-20 2010-03-23 Chevron Oronite Company Llc Synergistic lubricating oil composition containing a mixture of a nitro-substituted diarylamine and a diarylamine
RU2452767C1 (ru) * 2010-11-12 2012-06-10 Российская Федерация, От Имени Которой Выступает Министерство Промышленности И Торговли Российской Федерации Смазочная композиция универсального синтетического масла, работоспособного в газотурбинных двигателях и редукторах вертолетов, а также турбовинтовых двигателях и турбовинтовентиляторных двигателях самолетов

Family Cites Families (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
NL269857A (enrdf_load_stackoverflow) * 1960-10-07
US3126344A (en) * 1961-01-03 1964-03-24 Synthetic ester lubricating oil
US3148147A (en) * 1961-01-31 1964-09-08 Eastman Kodak Co 2, 2-dialkyl-1, 3-propanediol diesters as functional fluids
GB1028515A (en) * 1961-12-27 1966-05-04 Gen Electric Improvements in bearing assemblies of contra-rotating electric motors
US3247111A (en) * 1963-04-08 1966-04-19 Socony Mobil Oil Co High temperature jet lubricant
GB1053062A (enrdf_load_stackoverflow) * 1963-04-30
US3309314A (en) * 1964-05-29 1967-03-14 Shell Oil Co Lubricant compositions
GB1180385A (en) * 1966-07-21 1970-02-04 British Petroleum Co High Temperature Antioxidants and Lubricants containing them
IL31600A0 (en) * 1968-03-25 1969-04-30 Stauffer Chemical Co Lubricant composition containing an antioxidant

Cited By (24)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3879307A (en) * 1973-05-18 1975-04-22 Mobil Oil Corp Organic compositions containing synergistic antioxidant mixtures
US4245939A (en) * 1978-12-13 1981-01-20 F. Jos. Lamb Company Method and apparatus for machining spherical combustion chambers
US4770802A (en) * 1986-02-04 1988-09-13 Nippon Oil Co., Ltd. Lubricating oil compositions
US5073278A (en) * 1988-07-18 1991-12-17 Ciba-Geigy Corporation Lubricant composition
US5273669A (en) * 1988-07-18 1993-12-28 Ciba-Geigy Corporation Lubricant composition
US5102567A (en) * 1990-06-25 1992-04-07 Amoco Corporation High performance food-grade lubricating oil
WO1995017488A3 (en) * 1993-12-15 1995-07-20 Exxon Research Engineering Co Lubricant composition containing a polymeric antioxidant
US6426324B1 (en) * 1993-12-15 2002-07-30 Noveon Ip Holdings Corp. Lubricant composition
US5489711A (en) * 1994-12-20 1996-02-06 The B. F. Goodrich Company Synthetic lubricant antioxidant from monosubstituted diphenylamines
US5714441A (en) * 1996-07-12 1998-02-03 Exxon Research And Engineering Company Additive combination to reduce deposit forming tendencies and improve antioxidancy of aviation turbine oils
US5730906A (en) * 1996-07-12 1998-03-24 Exxon Research And Engineering Company Additive combination to reduce deposit forming tendencies and improve antioxidancy of aviation turbine oils (Law406)
US5856280A (en) * 1996-07-12 1999-01-05 Exxon Research And Engineering Company Sulfur-containing carboxylic acid derivatives to reduce deposit forming tendencies and improve antioxidancy of aviation turbine oils
WO2003048281A1 (en) * 2001-11-29 2003-06-12 Crompton Corporation Viscosity growth inhibition in oil additive concentrates
US20080045425A1 (en) * 2006-08-15 2008-02-21 Dibella Eugene P Antioxidants and Methods of Making Antioxidants
US7413682B2 (en) 2006-08-15 2008-08-19 Anderol, Inc. Antioxidants and methods of making antioxidants
US7307049B1 (en) * 2007-02-08 2007-12-11 Anderol, Inc. Antioxidants for synthetic lubricants and methods and manufacture
WO2008097390A1 (en) 2007-02-08 2008-08-14 Anderol, Inc. Antioxidants for synthetic lubricants and methods of manufacture
US20080194445A1 (en) * 2007-02-08 2008-08-14 Dibella Eugene P Antioxidants for Synthetic Lubricants and Methods of Manufacture
JP2010514775A (ja) * 2007-02-08 2010-05-06 ケムチュア コーポレイション 合成潤滑剤のための酸化防止剤及び製造方法
US7906467B2 (en) * 2007-02-08 2011-03-15 Chemtura Corporation Antioxidants for synthetic lubricants and methods of manufacture
RU2458097C2 (ru) * 2007-02-08 2012-08-10 Кемтура Корпорейшн Антиоксиданты для синтетических смазочных материалов и способы их производства
CN101617024B (zh) * 2007-02-08 2014-02-12 科聚亚公司 合成润滑剂用抗氧化剂和制造方法
CN114479986A (zh) * 2020-10-27 2022-05-13 中国石油化工股份有限公司 抗氧剂组合物及其制备方法
CN114479986B (zh) * 2020-10-27 2023-10-10 中国石油化工股份有限公司 抗氧剂组合物及其制备方法

Also Published As

Publication number Publication date
FR2160368B1 (enrdf_load_stackoverflow) 1978-07-28
JPS5232361B2 (enrdf_load_stackoverflow) 1977-08-20
GB1401755A (en) 1975-07-30
DE2233542C3 (de) 1981-11-05
GB1400178A (en) 1975-07-16
NL7215476A (enrdf_load_stackoverflow) 1973-05-21
AU470026B2 (en) 1976-03-04
FR2160368A1 (enrdf_load_stackoverflow) 1973-06-29
JPS4860107A (enrdf_load_stackoverflow) 1973-08-23
DE2233542A1 (de) 1973-05-24
CA976539A (en) 1975-10-21
AU4518572A (en) 1974-02-07
NL164895B (nl) 1980-09-15
IT968798B (it) 1974-03-20
DE2233542B2 (de) 1981-04-02
NL164895C (nl) 1981-02-16

Similar Documents

Publication Publication Date Title
US3773665A (en) Lubricants containing amine antioxidants
US4104179A (en) Lubricating and petroleum fuel oil compositions containing azole polysulfide wear inhibitors
US3312620A (en) Amide lubricants
US4519928A (en) Lubricant compositions containing N-tertiary alkyl benzotriazoles
DE3852207T2 (de) Zweckgebundene Flüssigkeiten.
US3634238A (en) Organic compositions containing amines and metals or salts thereof
US3849319A (en) Di and tri(hydrocarbylammonium)trithiocyanurate and lubricating oil compositions containing same
US5213699A (en) N-allyl substituted phenylenediamine stabilizers
JP2943004B2 (ja) 潤滑剤組成物
US4122021A (en) Antioxidant stabilized lubricating oils
US3886211A (en) Carboxylic acid hydrazide derivatives
US3330763A (en) Lubricants containing an amino thiocyanate and a cyclic amine
USRE28805E (en) Lubricants containing amine antioxidants
US3642632A (en) Anthranilic acid esters as lubricant additives
US3609077A (en) Lubricant compositions
US3882042A (en) Antioxidant composition of a rearrangement product of a tetra-aryl hydrazine with an alkali metal compound
US3216939A (en) Stabilization of lubricants
US3779919A (en) Synthetic aircraft turbine oil
US3767575A (en) Oxidation resistant lubricant compositions
US3882043A (en) Antioxidant composition of a rearrangement product of a tetra-aryl hydrazine and a thiazine or amine
DE2203468A1 (de) Acylierte Phenylendiamine
US5560848A (en) Combination diphenyl amine-phenothiazine additive for improved oxidation stability in polyol ester based greases (Law236)
DE69007214T2 (de) Butenylaromatische Aminstabilisatoren.
EP0089023B1 (en) Stabilizer systems useful in lubricating oils and method for stabilizing lubricating oils
US3798166A (en) Lubricant compositions