GB1332201A - Alkylated diphenylamines - Google Patents

Alkylated diphenylamines

Info

Publication number
GB1332201A
GB1332201A GB315971A GB1332201DA GB1332201A GB 1332201 A GB1332201 A GB 1332201A GB 315971 A GB315971 A GB 315971A GB 1332201D A GB1332201D A GB 1332201DA GB 1332201 A GB1332201 A GB 1332201A
Authority
GB
United Kingdom
Prior art keywords
diphenylamine
methyl
compounds
isopropylcyclohex
methylcyclohexyl
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
GB315971A
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.)
Ciba Geigy UK Ltd
Original Assignee
Ciba Geigy UK 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
Application filed by Ciba Geigy UK Ltd filed Critical Ciba Geigy UK Ltd
Publication of GB1332201A publication Critical patent/GB1332201A/en
Expired legal-status Critical Current

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    • FMECHANICAL ENGINEERING; LIGHTING; HEATING; WEAPONS; BLASTING
    • F27FURNACES; KILNS; OVENS; RETORTS
    • F27DDETAILS OR ACCESSORIES OF FURNACES, KILNS, OVENS, OR RETORTS, IN SO FAR AS THEY ARE OF KINDS OCCURRING IN MORE THAN ONE KIND OF FURNACE
    • F27D3/00Charging; Discharging; Manipulation of charge
    • F27D3/12Travelling or movable supports or containers for the charge
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    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08KUse of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00Use of organic ingredients
    • C08K5/16Nitrogen-containing compounds
    • C08K5/17Amines; Quaternary ammonium compounds
    • C08K5/18Amines; Quaternary ammonium compounds with aromatically bound amino groups
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    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09KMATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K15/00Anti-oxidant compositions; Compositions inhibiting chemical change
    • C09K15/04Anti-oxidant compositions; Compositions inhibiting chemical change containing organic compounds
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    • C10M133/02Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing nitrogen having a carbon chain of less than 30 atoms
    • C10M133/04Amines, e.g. polyalkylene polyamines; Quaternary amines
    • C10M133/12Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to a carbon atom of a six-membered aromatic ring
    • FMECHANICAL ENGINEERING; LIGHTING; HEATING; WEAPONS; BLASTING
    • F27FURNACES; KILNS; OVENS; RETORTS
    • F27BFURNACES, KILNS, OVENS, OR RETORTS IN GENERAL; OPEN SINTERING OR LIKE APPARATUS
    • F27B9/00Furnaces through which the charge is moved mechanically, e.g. of tunnel type; Similar furnaces in which the charge moves by gravity
    • F27B9/14Furnaces through which the charge is moved mechanically, e.g. of tunnel type; Similar furnaces in which the charge moves by gravity characterised by the path of the charge during treatment; characterised by the means by which the charge is moved during treatment
    • F27B9/20Furnaces through which the charge is moved mechanically, e.g. of tunnel type; Similar furnaces in which the charge moves by gravity characterised by the path of the charge during treatment; characterised by the means by which the charge is moved during treatment the charge moving in a substantially straight path tunnel furnace
    • F27B9/26Furnaces through which the charge is moved mechanically, e.g. of tunnel type; Similar furnaces in which the charge moves by gravity characterised by the path of the charge during treatment; characterised by the means by which the charge is moved during treatment the charge moving in a substantially straight path tunnel furnace on or in trucks, sleds, or containers
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    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2223/00Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
    • C10M2223/02Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having no phosphorus-to-carbon bonds
    • C10M2223/04Phosphate esters
    • C10M2223/045Metal containing thio derivatives
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    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2223/00Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
    • C10M2223/02Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having no phosphorus-to-carbon bonds
    • C10M2223/04Phosphate esters
    • C10M2223/047Thioderivatives not containing metallic elements
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    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2223/00Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
    • C10M2223/06Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having phosphorus-to-carbon bonds
    • C10M2223/065Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having phosphorus-to-carbon bonds containing sulfur
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    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10NINDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2010/00Metal present as such or in compounds
    • C10N2010/02Groups 1 or 11
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    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
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    • C10N2050/00Form in which the lubricant is applied to the material being lubricated
    • C10N2050/10Semi-solids; greasy

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  • Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Organic Chemistry (AREA)
  • Mechanical Engineering (AREA)
  • General Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Materials Engineering (AREA)
  • Polymers & Plastics (AREA)
  • Medicinal Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • General Chemical & Material Sciences (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Anti-Oxidant Or Stabilizer Compositions (AREA)
  • Lubricants (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
  • Compositions Of Macromolecular Compounds (AREA)

Abstract

1332201 Alkylated diphenylamines CIBAGEIGY (UK) Ltd 25 Jan 1972 [26 Jan 1971] 3159/71 Heading C2C [Also in Division C5] The invention comprises compounds of formula in which R 1 is a C 1 -C 4 alkyl group, R 2 is methyl and R 3 is a cycloalkyl or cycloalkenyl radical having 5-12 carbon atoms being either unsubstituted or substituted with an alkyl group, or in which R 2 and R 3 , together with the carbon atom to which they are attached form a carbocyclic ring system having from 5 to 12 carbon atoms in the ring, the ring being either unsubstituted or substituted with an alkyl group. The compounds are prepared by alkylating diphenylamine with an appropriate olefin, cyclopropane or cyclobutane in the presence of a Friedel Crafts catalyst which may be a Lewis acid (e.g. AlCl 3 or ZnCl 2 ) or a Bronsted acid (acid washed Montmorillonite), the reaction being carried out preferably by heating in the presence of an inert organic solvent. The compounds of the invention are useful as antioxidants for a wide variety of listed organic materials especially synthetic lubricants. Examples of the compounds of the invention are p,p<SP>1</SP> - di - (1 - methylcyclohexyl)diphenylamine, p,p<SP>1</SP> - di - (1 - methyl - 4 - isopropylcyclohex - 1- enyl - 4)diphenylamine, p,p<SP>1</SP> - di - (2 - methyl- 4 - isopropylcyclohex - 1 - enyl - 4)diphenylamine, p,p<SP>1</SP> - di - (2 - methyl - 3 - isopropylcyclohex - 1 - enyl - 3)diphenylamine, p,p<SP>1</SP> - di- (1 - isopropyl - 4 - methylcyclohexyl)diphenylamine, p,p<SP>1</SP> - di - (1 - isopropyl - 3 - methylcyclohexyl)diphenylamine, p,p<SP>1</SP> - di[α - methyl - (1- methylcyclohexen - 1 - yl - 4)ethyl]diphenylamine and p,p<SP>1</SP> - di - (1 - methyl - 4 - isopropenylcyclohexyl)diphenylamine.
GB315971A 1971-01-26 1971-01-26 Alkylated diphenylamines Expired GB1332201A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB315971 1971-01-26

Publications (1)

Publication Number Publication Date
GB1332201A true GB1332201A (en) 1973-10-03

Family

ID=9753058

Family Applications (1)

Application Number Title Priority Date Filing Date
GB315971A Expired GB1332201A (en) 1971-01-26 1971-01-26 Alkylated diphenylamines

Country Status (7)

Country Link
BE (1) BE778450A (en)
DE (1) DE2203407A1 (en)
ES (1) ES399559A1 (en)
FR (1) FR2124838A5 (en)
GB (1) GB1332201A (en)
IT (1) IT946915B (en)
NL (1) NL7201012A (en)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4824601A (en) * 1983-12-08 1989-04-25 Ciba-Geigy-Corporation Liquid antioxidant produced by alkylating diphenylamine with a molar excess of diisobutylene
EP0399764A1 (en) 1989-05-22 1990-11-28 Ethyl Petroleum Additives Limited Lubricant compositions
WO2010028179A1 (en) * 2008-09-03 2010-03-11 Dr. Reddy's Laboratories Ltd. Heterocyclic compounds as gata modulators

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4812543A (en) * 1988-03-01 1989-03-14 Hercules Incorporated Co-polymer-bound amine antioxidants

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4824601A (en) * 1983-12-08 1989-04-25 Ciba-Geigy-Corporation Liquid antioxidant produced by alkylating diphenylamine with a molar excess of diisobutylene
EP0399764A1 (en) 1989-05-22 1990-11-28 Ethyl Petroleum Additives Limited Lubricant compositions
WO2010028179A1 (en) * 2008-09-03 2010-03-11 Dr. Reddy's Laboratories Ltd. Heterocyclic compounds as gata modulators

Also Published As

Publication number Publication date
DE2203407A1 (en) 1972-08-17
ES399559A1 (en) 1974-10-16
IT946915B (en) 1973-05-21
BE778450A (en) 1972-07-25
FR2124838A5 (en) 1972-09-22
NL7201012A (en) 1972-07-28

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