GB1046353A - Tertiary substituted diarylamine derivatives and their use as antioxidants in lubricants - Google Patents

Tertiary substituted diarylamine derivatives and their use as antioxidants in lubricants

Info

Publication number
GB1046353A
GB1046353A GB5593/64A GB559364A GB1046353A GB 1046353 A GB1046353 A GB 1046353A GB 5593/64 A GB5593/64 A GB 5593/64A GB 559364 A GB559364 A GB 559364A GB 1046353 A GB1046353 A GB 1046353A
Authority
GB
United Kingdom
Prior art keywords
phenyl
naphthylamine
tertiary
diphenylamine
butyl
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
Application number
GB5593/64A
Inventor
Donald Richard Randell
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.)
Geigy Co Ltd
Original Assignee
Geigy Co Ltd
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 NL135724D priority Critical patent/NL135724C/xx
Application filed by Geigy Co Ltd filed Critical Geigy Co Ltd
Priority to GB5593/64A priority patent/GB1046353A/en
Priority to GB54004/65A priority patent/GB1090688A/en
Priority to CH142865A priority patent/CH454329A/en
Priority to BE659527D priority patent/BE659527A/xx
Priority to NL6501652A priority patent/NL6501652A/xx
Priority to DEG42809A priority patent/DE1281617B/en
Priority to CH181765A priority patent/CH455110A/en
Priority to SE01783/65A priority patent/SE336794B/xx
Priority to SE05255/70A priority patent/SE368222B/xx
Priority to SE05253/70A priority patent/SE368220B/xx
Priority to FR5124A priority patent/FR1429495A/en
Priority to SE17421/67A priority patent/SE357564B/xx
Priority to SE05254/70A priority patent/SE368221B/xx
Priority to DEG42949A priority patent/DE1282218B/en
Priority to US526401A priority patent/US3414618A/en
Priority to US588225A priority patent/US3475412A/en
Publication of GB1046353A publication Critical patent/GB1046353A/en
Priority to US753321*A priority patent/US3536706A/en
Priority to US870959A priority patent/US3577343A/en
Priority to US6308A priority patent/US3642629A/en
Priority to US6309A priority patent/US3696851A/en
Priority to NL7102393A priority patent/NL7102393A/xx
Priority to NL717102392A priority patent/NL145232B/en
Expired 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
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/16—Nitrogen-containing compounds
    • C08K5/34—Heterocyclic compounds having nitrogen in the ring
    • C08K5/3412—Heterocyclic compounds having nitrogen in the ring having one nitrogen atom in the 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
    • 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
    • C10M2207/30—Complex esters, i.e. compounds containing at leasst three esterified carboxyl groups and derived from the combination of at least three different types of the following five types of compounds: monohydroxyl compounds, polyhydroxy xompounds, monocarboxylic acids, polycarboxylic acids or hydroxy carboxylic acids
    • 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
    • C10M2207/30—Complex esters, i.e. compounds containing at leasst three esterified carboxyl groups and derived from the combination of at least three different types of the following five types of compounds: monohydroxyl compounds, polyhydroxy xompounds, monocarboxylic acids, polycarboxylic acids or hydroxy carboxylic acids
    • C10M2207/302—Complex esters, i.e. compounds containing at leasst three esterified carboxyl groups and derived from the combination of at least three different types of the following five types of compounds: monohydroxyl compounds, polyhydroxy xompounds, monocarboxylic acids, polycarboxylic acids or hydroxy carboxylic acids derived from the combination of monocarboxylic acids, dicarboxylic acids and dihydroxy compounds only and having no free hydroxy or carboxyl groups
    • C—CHEMISTRY; METALLURGY
    • 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
    • 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
    • C10M2215/02—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
    • C10M2215/065—Phenyl-Naphthyl 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
    • C10M2215/14—Containing carbon-to-nitrogen double bounds, e.g. guanidines, hydrazones, semicarbazones
    • 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
    • C10M2215/22—Heterocyclic nitrogen 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
    • C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2215/22—Heterocyclic nitrogen compounds
    • C10M2215/221—Six-membered rings containing nitrogen and carbon only
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • 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
    • C10M2215/22—Heterocyclic nitrogen compounds
    • C10M2215/225—Heterocyclic nitrogen compounds the rings containing both nitrogen and oxygen
    • 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
    • C10M2215/22—Heterocyclic nitrogen compounds
    • C10M2215/225—Heterocyclic nitrogen compounds the rings containing both nitrogen and oxygen
    • C10M2215/226—Morpholines
    • 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
    • C10M2215/30—Heterocyclic 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
    • C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
    • C10M2219/10—Heterocyclic compounds containing sulfur, selenium or tellurium compounds in the 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
    • C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
    • C10M2219/10—Heterocyclic compounds containing sulfur, selenium or tellurium compounds in the ring
    • C10M2219/104—Heterocyclic compounds containing sulfur, selenium or tellurium compounds in the ring containing sulfur and carbon with nitrogen or oxygen in the ring
    • C10M2219/108—Phenothiazine
    • 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

Abstract

A synthetic lubricant comprises as antioxidant an amine of the formula A-NH-B, where A is a C4 to C12 tertiary alkyl substituted phenyl group and B is phenyl or naphthyl, in particular wherein the lubricant is based on a carboxylic ester or esters, especially based on polyesters. Particularly specified are esters of a dibasic acid and a monolydnic alcohol, an ester of trimethylol propane and a monobasic or mixtures of such acids, esters of pentaerythritol and a monobasic acid or mixtures of such acids or complex esters of mono- and di-basic acids and polyhydric alcohols. Especially useful are di-2-ethylhexyl sebacate, trimethylolpropane tripelargonate, pentaerythritol tetracaprylate and a complex ester derived from trimethylol propane, caprylic acid and sebacic acid. Named antioxidants are 4 - tertiary - butyl - diphenylamine, N - p - tertiary - butyl - phenyl - a - naphthylamine, N - p - tertiary - butyl - phenyl - b - naphthylamine, 4 - tertiary - pentyl - diphenylamine, N-p - tertiary - pentyl - phenyl - a - naphthylamine N - p - tertiary - pentyl - phenyl - b - naphthylamine, N - p - tertiary - hexyl - phenyl - b - naphthylamine, N - p tertiary - hexyl - phenyl-a - naphthylamine, 4 - (11: 11: 31: 31 - tetra - methylbutyl) - diphenylamine, N - p - (11: 11: 31: 31 - tetramethylbutyl) - phenyl - a - naphthylamine, N - p - (11: 11: 31: 31 - tetramethylbutyl)-phenyl - b - naphthylamine, 4 - (11: 11: 31: 31: 51: 51 - hexamethylhexyl) - diphenylamine, N - p - (11: 11: 31: 31: 51: 51 - hexamethylhexyl) - phenyl - a - naphthylamine or N - p - (11: 11: 31: 31: 51: 51 - hexamethylhexyl - phenyl - b - naphthylamine. The composition may include the conventional additives, e.g. benzotriazole. The examples include comparative data on phenothiazine; iminodibenzyl diphenylamine; ditert-octyl iminodibenzyl; N-phenyl-a - and b -naphthylamines; 4,41-ditert-octyl diphenylamine.ALSO:Novel N-p-tertiary butyl-, octyl-, pentyl-, hexyl-phenyl -a - and -b -naphthylamines may be produced from phenyl a or b naphthylamine by Friedel-Crafts alkylation using alkenes or alkyl halides. The examples also describe the preparation of 4, and 4,41-ditertiary octyldiphenylamine, 4 and 4,41-ditertiary butyl diphenylamine, as well as the above. The compounds are antioxidants for synthetic ester lubricant compositions (see Division C5).
GB5593/64A 1960-12-09 1964-02-11 Tertiary substituted diarylamine derivatives and their use as antioxidants in lubricants Expired GB1046353A (en)

Priority Applications (23)

Application Number Priority Date Filing Date Title
NL135724D NL135724C (en) 1964-02-11
GB5593/64A GB1046353A (en) 1964-02-11 1964-02-11 Tertiary substituted diarylamine derivatives and their use as antioxidants in lubricants
GB54004/65A GB1090688A (en) 1964-02-11 1964-02-29 Tertiary alkyl substituted heterocyclic compounds and their use as antioxidants
CH142865A CH454329A (en) 1964-02-11 1965-02-02 Process for stabilizing synthetic lubricants
BE659527D BE659527A (en) 1964-02-11 1965-02-10
NL6501652A NL6501652A (en) 1964-02-11 1965-02-10
DEG42809A DE1281617B (en) 1964-02-11 1965-02-10 Lubricating oil
CH181765A CH455110A (en) 1964-02-11 1965-02-10 Process for stabilizing synthetic lubricants
SE05253/70A SE368220B (en) 1964-02-11 1965-02-11
SE05254/70A SE368221B (en) 1964-02-11 1965-02-11
SE05255/70A SE368222B (en) 1964-02-11 1965-02-11
SE01783/65A SE336794B (en) 1964-02-11 1965-02-11
FR5124A FR1429495A (en) 1964-02-11 1965-02-11 Alkylated heterocyclic compounds usable in particular as antioxidants
SE17421/67A SE357564B (en) 1964-02-11 1965-02-11
DEG42949A DE1282218B (en) 1964-02-11 1965-02-26 Lubricating oil
US526401A US3414618A (en) 1964-02-11 1966-02-10 Mono-p-tertiary alkyl diarylamines
US588225A US3475412A (en) 1960-12-09 1966-10-20 Dibenzazepine compounds useful as stabilizers for oxidizable organic compositions
US753321*A US3536706A (en) 1964-02-11 1968-04-26 Phenothiazine compounds
US870959A US3577343A (en) 1960-12-09 1969-10-27 Dibenzazepine compounds as stabilizer for oxidizable organic compositions
US6308A US3642629A (en) 1964-02-11 1970-01-27 Chemical compounds and compositions
US6309A US3696851A (en) 1964-02-11 1970-01-27 Chemical compounds and compositions
NL7102393A NL7102393A (en) 1964-02-11 1971-02-23
NL717102392A NL145232B (en) 1964-02-11 1971-02-23 PROCESS FOR THE PREPARATION OF AROMATIC THIAZINE DERIVATIVES AND SYNTHETIC LUBRICANTS CONTAINING THESE DERIVATIVES.

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
GB5593/64A GB1046353A (en) 1964-02-11 1964-02-11 Tertiary substituted diarylamine derivatives and their use as antioxidants in lubricants
GB857964 1964-02-29

Publications (1)

Publication Number Publication Date
GB1046353A true GB1046353A (en) 1966-10-26

Family

ID=26240010

Family Applications (1)

Application Number Title Priority Date Filing Date
GB5593/64A Expired GB1046353A (en) 1960-12-09 1964-02-11 Tertiary substituted diarylamine derivatives and their use as antioxidants in lubricants

Country Status (6)

Country Link
BE (1) BE659527A (en)
CH (2) CH454329A (en)
DE (2) DE1281617B (en)
GB (1) GB1046353A (en)
NL (2) NL6501652A (en)
SE (5) SE368222B (en)

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0097118A2 (en) * 1982-06-10 1983-12-28 Ciba-Geigy Ag Liquid antioxidants for lubricants and elastomers
US6930183B2 (en) * 2003-04-17 2005-08-16 Crompton Corporation Alkylated iminodibenzyls as antioxidants
WO2017011159A1 (en) * 2015-07-15 2017-01-19 Chemtura Corporation Diaryl amine antioxidants prepared from branched olefins
US9637704B2 (en) 2014-09-19 2017-05-02 Vanderbilt Chemicals, Llc Polyalkylene glycol-based industrial lubricant compositions
US11339345B2 (en) 2020-02-28 2022-05-24 Vanderbilt Chemicals, Llc Liquid octylated phenyl-α-naphthylamine composition

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2781318A (en) * 1952-03-28 1957-02-12 Exxon Research Engineering Co Mineral lubricating oil additive
NL247300A (en) * 1959-01-14

Cited By (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0097118A2 (en) * 1982-06-10 1983-12-28 Ciba-Geigy Ag Liquid antioxidants for lubricants and elastomers
EP0097118A3 (en) * 1982-06-10 1984-07-25 Ciba-Geigy Ag Liquid antioxidants for lubricants and elastomers
US6930183B2 (en) * 2003-04-17 2005-08-16 Crompton Corporation Alkylated iminodibenzyls as antioxidants
US9637704B2 (en) 2014-09-19 2017-05-02 Vanderbilt Chemicals, Llc Polyalkylene glycol-based industrial lubricant compositions
RU2659788C1 (en) * 2014-09-19 2018-07-04 ВАНДЕРБИЛТ КЕМИКАЛЗ, ЭлЭлСи Polyalkylene glycol based industrial lubricant compositions
WO2017011159A1 (en) * 2015-07-15 2017-01-19 Chemtura Corporation Diaryl amine antioxidants prepared from branched olefins
CN107835799A (en) * 2015-07-15 2018-03-23 朗盛解决方案美国公司 The diarylamine antioxidant prepared by branched-chain alkene
US10487043B2 (en) 2015-07-15 2019-11-26 Lanxess Solutions Us Inc. Diaryl amine antioxidants prepared from branched olefins
CN107835799B (en) * 2015-07-15 2024-02-09 朗盛公司 Diarylamine antioxidants prepared from branched olefins
US11339345B2 (en) 2020-02-28 2022-05-24 Vanderbilt Chemicals, Llc Liquid octylated phenyl-α-naphthylamine composition

Also Published As

Publication number Publication date
BE659527A (en) 1965-08-10
SE357564B (en) 1973-07-02
CH454329A (en) 1968-04-15
DE1282218B (en) 1968-11-07
SE368221B (en) 1974-06-24
CH455110A (en) 1968-04-30
SE336794B (en) 1971-07-19
NL6501652A (en) 1965-08-12
SE368222B (en) 1974-06-24
NL135724C (en)
DE1281617B (en) 1968-10-31
SE368220B (en) 1974-06-24

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