GB575736A - Improvements in the preservation of rubber compositions - Google Patents

Improvements in the preservation of rubber compositions

Info

Publication number
GB575736A
GB575736A GB19653/43A GB1965343A GB575736A GB 575736 A GB575736 A GB 575736A GB 19653/43 A GB19653/43 A GB 19653/43A GB 1965343 A GB1965343 A GB 1965343A GB 575736 A GB575736 A GB 575736A
Authority
GB
United Kingdom
Prior art keywords
phenyl
benzenesulphonyl
methyl
phenylenediamine
toluenesulphonyl
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
GB19653/43A
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.)
Uniroyal Inc
Original Assignee
United States Rubber Co
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 United States Rubber Co filed Critical United States Rubber Co
Publication of GB575736A publication Critical patent/GB575736A/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
    • C08K5/36Sulfur-, selenium-, or tellurium-containing compounds
    • C08K5/43Compounds containing sulfur bound to nitrogen

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  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Compositions Of Macromolecular Compounds (AREA)

Abstract

An antioxidant or age-resistor for incorporation in natural or synthetic rubber compositions comprises an N-aryl-N1-alkyl-N1-arylsulphonyl-arylenediamine of the general formula <FORM:0575736/IV/1> wherein A represents an open-chain aliphatic, cycloalkyl, or aralkyl hydrocarbon group, optionally substituted; "aryl" represents a benzene, naphthalene or biphenyl residue and "arylene" represents an aromatic residue containing one or more rings. As further nuclear substituents, the N-aryl group may carry alkyl, alkenyl, alkoxy, aryloxy, dialkylamino or anilino groups, or halogen atoms; the arylene nucleus may carry alkyl or alkoxy groups or halogenatoms, the N1-aryl nucleus of the arylsulphonyl group may carry, for example, alkyl groups, and the N1-alkyl radical may carry chlorine atoms or alkoxy or amino groups. The substances are prepared, in general, by treating an arylsulphonylaminodiarylmaine in alkaline solution with an aliphatic halide or sulphate. As antioxidants are specified (a) the following p-phenylenediamine derivatives, viz. the N-phenyl-N1-methyl-N1-benzenesulphonyl-, N - phenyl - N1 - ethyl - N1 - benzenesulphonyl-, N - phenyl - N1 - butyl - N1 - benzenesulphonyl-, N - phenyl - N1 - lauryl - N1 - benzenesulphonyl-, N - phenyl - N1 - allyl - N1 - benzenesulphonyl-, N - phenyl - N1 - b - methallyl - N1 - benzenesulphonyl-, N-phenyl-N1-cyclohexyl-N1-benzenesulphonyl-, N-phenyl-N1-benzyl-N1-benzenesulphonyl-, N-p-tolyl-N1-methyl-N1-benzenesulphonyl-, N-p-methoxyphenyl-N1-methyl-N1-benzenesulphonyl-, N-phenyl-N1-methyl-N1-p-toluenesulphonyl-, N-phenyl-N1-methyl-N1-p-toluenesulphonyl-, N-phenyl-N1-methyl-N1-p-biphenylsulphonyl-, N - phenyl - N1 - b - hydroxyethyl-N1-benzenesulphonyl-, N-phenyl-N1-b -methoxyethyl-N1-benzenesulphonyl- and N-phenyl-N1-b -chloroethyl-N1-benzenesulphonyl -derivatives; (b) N-phenyl-N1-methyl-N1-benzenesulphonyl-o -phenylenediamine and the corresponding m-phenylenediamine derivative; (c) N-phenyl-N1-methyl-N1-benzene - sulphonyl-1 : 4-naphthylene diamine and the corresponding benzidine derivative. N-p-tolyl-N1-b -methallyl-N1-p-toluenesulphonyl-p -phenylenediamine is obtained by heating under reflux b -methallylchloride with N-p-tolyl - N1 - p - toluenesulphonyl - p - phenylene - diamine (Cf. Specification 406,479) in alcohol, containing aqueous potassium hydroxide and sodium hydrosulphite. N-p-tolyl-N1-methyl-N1-p-toluenesulphonyl-p -phenylenediamine is obtained by interaction of dimethyl sulphate and N-p-tolyl-N1-p-toluenesulphonyl - p - phenylenediamine in aqueous potassium hydroxide. N-p-tolyl-N1-ethyl-N1-p-toluenesulphonyl-p -phenylenediamine is obtained by interaction of diethyl sulphate and N-p-tolyl-N1-p-toluenesulphonyl - p - phenylenediamine in aqueous alcoholic potassium hydroxide containing sodium hydrosulphite. N-phenyl-N1-methyl-N1-p-toluenesulphonyl-p -phenylenediamine is obtained by interaction of dimethyl sulphate and N-phenyl-N1-p-toluenesulphonyl - p - phenylenediamine (Cf. Specification 406,479) in aqueous potassium hydroxide containing sodium hydrosulphite.ALSO:Compositions of natural and synthetic rubber, including polychloroprene, olefine polysulphides, butadiene polymers, "Buna" (Registered Trade Mark) N and Buna S and also reclaims and latices of such compositions, are preserved by incorporating therein as an antioxidant or age-resister an N - aryl - N1 - alkyl - N1 - arylsul - phonyl-arylene diamine of the general formula <FORM:0575736/V/1> wherein A represents an open-chain aliphatic, cycloalkyl, or aralkyl hydrocarbon group, optionally substituted, "aryl" represents a benzene, naphthalene or biphenyl residue and "arylene" represents an aromatic residue containing one or more rings. As further nuclear substituents, the N-aryl group may carry alkyl, alkenyl, alkoxy, aryloxy, dialkylamino or anilino groups, or halogen atoms, the arylene nucleus may carry alkyl or alkoxy groups, or halogen atoms and the N1-aryl nucleus of the arylsulphonyl group may carry, for example, alkyl groups and the N1-alkyl radical may carry chronine atoms or alkoxy or amino groups. The substances are prepared, in general, by treating an arylsulphonylaminodiarylamine in alkaline solution with an aliphatic halide or sulphate (see Group IV). As antioxidants are specified (a) the following p-phenylenediamine derivatives, viz., the N-phenyl-N1-methyl-N1-benzenesulphonyl-, N - phenyl - N1 - ethyl - N1 - benzenesulphonyl-, N - phenyl - N1 - butyl - N1 - benzenesulphonyl-, N - phenyl - N1 - lauryl - N1 - benzenesulphonyl-, N - phenyl - N1 - allyl - N1 - benzenesulphonyl-, N - phenyl - N1- b - methallyl - N1 - benzenesulphonyl-, N - phenyl - N1 - cyclo - hexyl - N1 - benzenesulphonyl-, N - phenyl - N1 - benzyl - N1 - benzenesulphonyl, N - p - tolyl - N1 - methyl - N1 - benzenesulphonyl-, N - p - methoxy - phenyl - N1 - methyl - N1 - benzenesulphonyl-, N - phenyl - N1 - methyl - N1 - p - toluenesulphonyl-, N - phenyl - N1 - methyl - N1-p-biphenylsulphonyl-, N - phenyl - N1 - b - hydroxyethyl - N1 - benzenesulphonyl-, N - phenyl - N1 - b - methoxyethyl - N1 - benzenesulphonyl- and N-phenyl-N1-b -chloroethyl - N1 - benzenesulphonyl - derivatives, and the compounds; (b) N-phenyl-N1-methyl-N1-benzenesulphonyl-o -phenylenediamine and the corresponding m-phenylenediamine derivative; (c) N-phenyl-N1-methyl-N1-benzenesulphonyl-1 : 4-naphthylene diamine and the corresponding benzidine derivative. The antioxidant may advantageously be in proportion from about 0.1 per cent to 5 per cent and it may be added in solution or incorporated by milling or mastication or prepared in forms suitable for incorporation by diffusion. In examples: (1) (a) 1 per cent of N-p-tolyl-N1-methyl-N1-p-toluenesulphonyl-p -phenylenediamine, (b) 1 per cent of N-p-tolyl-N1-b -methallyl-N1-p-toluenesulphonyl-p -phenylenediamine is incorporated in a composition comprising pale crepe rubber, tetramethylthiuram monosulphide, zinc oxide, calcium carbonate, lithopone, the zinc salt of coconut oil acids and sulphur; (2) (a) 1 per cent of N-p-tolyl-N1-ethyl-N1-p-toluenesulphonylamino - p - phenylenediamine, (b) 1 per cent of N-phenyl-N1-methyl-N1-p-toluenesulphonyl-p -phenylenediamine is incorporated in a composition comprising smoked sheet rubber, mercaptobenzothiazole, carbon black, zinc oxide, pine tar, the zinc salt of coconut oil acids and sulphur.
GB19653/43A 1943-01-29 1943-11-24 Improvements in the preservation of rubber compositions Expired GB575736A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US575736XA 1943-01-29 1943-01-29

Publications (1)

Publication Number Publication Date
GB575736A true GB575736A (en) 1946-03-04

Family

ID=22011442

Family Applications (1)

Application Number Title Priority Date Filing Date
GB19653/43A Expired GB575736A (en) 1943-01-29 1943-11-24 Improvements in the preservation of rubber compositions

Country Status (1)

Country Link
GB (1) GB575736A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2654679A (en) * 1947-07-15 1953-10-06 Shell Dev Stabilized reaction products of rubbery polymers with inorganic acidifying compounds

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2654679A (en) * 1947-07-15 1953-10-06 Shell Dev Stabilized reaction products of rubbery polymers with inorganic acidifying compounds

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