GB797138A - Rubber antioxidants - Google Patents

Rubber antioxidants

Info

Publication number
GB797138A
GB797138A GB2088655A GB2088655A GB797138A GB 797138 A GB797138 A GB 797138A GB 2088655 A GB2088655 A GB 2088655A GB 2088655 A GB2088655 A GB 2088655A GB 797138 A GB797138 A GB 797138A
Authority
GB
United Kingdom
Prior art keywords
methyl
tetrahydroquinoline
dialkyl
hydrogenating
aliphatic ketone
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
GB2088655A
Inventor
Bertrand Ernest Wilde
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.)
Monsanto Chemicals Ltd
Original Assignee
Monsanto Chemicals 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 Monsanto Chemicals Ltd filed Critical Monsanto Chemicals Ltd
Priority to GB2088655A priority Critical patent/GB797138A/en
Priority to FR1154986D priority patent/FR1154986A/en
Publication of GB797138A publication Critical patent/GB797138A/en
Expired legal-status Critical Current

Links

Classifications

    • CCHEMISTRY; METALLURGY
    • 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
    • C08K5/34Heterocyclic compounds having nitrogen in the ring
    • C08K5/3412Heterocyclic compounds having nitrogen in the ring having one nitrogen atom in the ring
    • C08K5/3432Six-membered rings
    • C08K5/3437Six-membered rings condensed with carbocyclic rings

Landscapes

  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

A 2:4 - dialkyl - 2 - methyl - 1:2:3:4 - tetrahydroquinoline may be prepared by hydrogenating a 2:4-dialkyl-2-methyl-1:2-dihydroquinoline obtained by condensing aniline with an aliphatic ketone, e.g. acetone or methyl ethyl ketone providing on subsequent hydrogenation 2:2:4 - trimethyl - 1:2:3:4 - tetrahydroquinoline and 2:4 - diethyl - 2 - methyl - 1:2:3:4 - tetrahydroquinoline, respectively. A 2:4 - dialkyl - 2 - methyl - 1:2:3:4 - tetrahydroquinoline substituted in the aryl nucleus by one or more hydrocarbon radical or radicals may be prepared by condensing aniline having the desired substituent or substituents, e.g. o- or p-toluidine, with an aliphatic ketone and hydrogenating the condensate.ALSO:A synthetic rubber such as a polymer of 1,3-butadiene or a copolymer thereof with styrene, acrylonitrile, isobutylene, or methyl methacrylate, contains a 2 : 4-dialkyl-2-methyl-1 : 2 : 3 : 4-tetrahydroquinoline as antioxidant. The latter may be prepared by condensing aniline with an aliphatic ketone, preferably containing an alkyl group of 1 to 4 carbon atoms, e.g. acetone or methyl ethyl ketone providing on subsequent hydrogenation 2 : 2 : 4 - trimethyl - 1 : 2 : 3 : 4 - tetrahydroquinoline and 2 : 4-dimethyl-1 : 2 : 3 : 4-tetrahydroquinoline, respectively. The 2 : 4-dialkyl - 2 - methyl - 1 : 2 : 3 : 4 - tetrahydroquinoline may contain at least one hydrocarbon substituent in the acryl nucleus, such a compound being obtainable by condensing aniline having the desired substituent or substituents, e.g. o- or p-toluidine, with an aliphatic ketone and hydrogenating the condensate.ALSO:Natural or synthetic rubber contains a 2 : 4 dialkyl-2-methyl-1 : 2 : 3 : 4 tetrahydroquinoline as antioxidant. The 2 : 4 dialkyl - 2 - methyl 1 : 2 : 3 : 4 tetrahydroquinolines may be obtained by hydrogenating 2 : 4 dialkyl-2-methyl-1 : 2 dihydroquinolines prepared by condensing aniline with an aliphatic ketone preferably containing an alkyl group of 1 to 4 carbon atoms, e.g., acetone, or methyl ethyl ketone providing on subsequent hydrogenation 2 : 2 : 4 trimethyl-1 : 2 : 3 : 4 tetrahydroquinoline and 2 : 4 diethyl-2-methyl-1 : 2 : 3 : 4 tetrahydroquinoline respectively. The 2 : 4-dialkyl-2-methyl-1 : 2 : 3 : 4-tetrahydroquinoline may contain at least one hydrocarbon substituent in the aryl nucleus, such a compound being obtainable by condensing aniline having the desired substituent or substituents, e.g., o or p toluidine, with an aliphatic ketone and hydrogenating the condensate.
GB2088655A 1955-07-19 1955-07-19 Rubber antioxidants Expired GB797138A (en)

Priority Applications (2)

Application Number Priority Date Filing Date Title
GB2088655A GB797138A (en) 1955-07-19 1955-07-19 Rubber antioxidants
FR1154986D FR1154986A (en) 1955-07-19 1956-07-18 Antioxidants for rubber

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB2088655A GB797138A (en) 1955-07-19 1955-07-19 Rubber antioxidants

Publications (1)

Publication Number Publication Date
GB797138A true GB797138A (en) 1958-06-25

Family

ID=10153432

Family Applications (1)

Application Number Title Priority Date Filing Date
GB2088655A Expired GB797138A (en) 1955-07-19 1955-07-19 Rubber antioxidants

Country Status (2)

Country Link
FR (1) FR1154986A (en)
GB (1) GB797138A (en)

Also Published As

Publication number Publication date
FR1154986A (en) 1958-04-18

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