US3773665A - Lubricants containing amine antioxidants - Google Patents

Lubricants containing amine antioxidants Download PDF

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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
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naphthylamine
composition
substituted
mixture
lubricant
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M Braid
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ExxonMobil Oil Corp
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Mobil Oil Corp
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    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M3/00—Liquid compositions essentially based on lubricating components other than mineral lubricating oils or fatty oils and their use as lubricants; Use as lubricants of single liquid substances
    • C—CHEMISTRY; METALLURGY
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    • 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
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    • 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
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    • C10M2205/00—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions
    • C—CHEMISTRY; METALLURGY
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    • 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
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    • 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
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    • 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
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    • 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
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    • 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
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    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/28—Esters
    • C10M2207/281—Esters of (cyclo)aliphatic monocarboxylic acids
    • C—CHEMISTRY; METALLURGY
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    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/28—Esters
    • C10M2207/282—Esters of (cyclo)aliphatic oolycarboxylic acids
    • C—CHEMISTRY; METALLURGY
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    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/28—Esters
    • C10M2207/283—Esters of polyhydroxy compounds
    • C—CHEMISTRY; METALLURGY
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    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/28—Esters
    • C10M2207/286—Esters of polymerised unsaturated acids
    • C—CHEMISTRY; METALLURGY
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    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/28—Esters
    • C10M2207/34—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
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    • 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
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    • C10M2209/00—Organic macromolecular compounds containing oxygen as ingredients in lubricant compositions
    • C10M2209/02—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
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    • C10M2209/00—Organic macromolecular compounds containing oxygen as ingredients in lubricant compositions
    • C10M2209/02—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M2209/04—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
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    • 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
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    • 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
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    • C10M2209/00—Organic macromolecular compounds containing oxygen as ingredients in lubricant compositions
    • C10M2209/10—Macromolecular compoundss obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • 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
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    • C10M2209/00—Organic macromolecular compounds containing oxygen as ingredients in lubricant compositions
    • C10M2209/10—Macromolecular compoundss obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M2209/103—Polyethers, i.e. containing di- or higher polyoxyalkylene groups
    • C10M2209/109—Polyethers, i.e. containing di- or higher polyoxyalkylene groups esterified
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
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    • C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2215/02—Amines, e.g. polyalkylene polyamines; Quaternary amines
    • C10M2215/06—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to carbon atoms of six-membered aromatic rings
    • C10M2215/064—Di- and triaryl amines
    • C—CHEMISTRY; METALLURGY
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    • C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2215/18—Containing nitrogen-to-nitrogen bonds, e.g. hydrazine
    • C10M2215/182—Azo compounds
    • C—CHEMISTRY; METALLURGY
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    • 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
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    • 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—Semi-solids; 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.

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

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US19973271A 1971-11-17 1971-11-17

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

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
WO1995017488A2 (en) * 1993-12-15 1995-06-29 Exxon Research & Engineering Company 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 (xx) * 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 (xx) * 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
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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

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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
US6426324B1 (en) * 1993-12-15 2002-07-30 Noveon Ip Holdings Corp. Lubricant composition
WO1995017488A3 (en) * 1993-12-15 1995-07-20 Exxon Research Engineering Co Lubricant composition containing a polymeric antioxidant
WO1995017488A2 (en) * 1993-12-15 1995-06-29 Exxon Research & Engineering Company 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
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
GB1400178A (en) 1975-07-16
FR2160368A1 (xx) 1973-06-29
JPS4860107A (xx) 1973-08-23
IT968798B (it) 1974-03-20
AU470026B2 (en) 1976-03-04
DE2233542C3 (de) 1981-11-05
FR2160368B1 (xx) 1978-07-28
NL164895C (nl) 1981-02-16
JPS5232361B2 (xx) 1977-08-20
DE2233542A1 (de) 1973-05-24
AU4518572A (en) 1974-02-07
DE2233542B2 (de) 1981-04-02
NL164895B (nl) 1980-09-15
NL7215476A (xx) 1973-05-21
GB1401755A (en) 1975-07-30
CA976539A (en) 1975-10-21

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