GB560958A - Improvements in antioxidants - Google Patents

Improvements in antioxidants

Info

Publication number
GB560958A
GB560958A GB14822/42A GB1482242A GB560958A GB 560958 A GB560958 A GB 560958A GB 14822/42 A GB14822/42 A GB 14822/42A GB 1482242 A GB1482242 A GB 1482242A GB 560958 A GB560958 A GB 560958A
Authority
GB
United Kingdom
Prior art keywords
amino
toluene
phenol
naphthol
sulphonyl
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
GB14822/42A
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 GB560958A publication Critical patent/GB560958A/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)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

Organic substances which deteriorate by absorption of oxygen from the air are preserved by incorporation of a sulphonyl amino phenol or naphthol of the formula (OH)x-R-(NH-SO2-R1)n, where R is an aromatic nucleus, R2 is an alkyl or aryl group, and x and n are integers. These anti-oxidants may be prepared by reacting amino phenols (or naphthols) with sulphonyl chlorides in the presence of a neutralizing base such as sodium acetate or carbonate. Solvents such as alcohol, acetone, methyl ethyl ketone, dioxane or benzene may also be present. Amino phenols specified are p-, m-, and o-aminophenol, 2, 4- and 3, 4-diaminophenol, 5-amino-1-naphthol, 1,6-diamino-2-naphthol, 2-amino- and 2,4-diamino-resorcinol, 2-amino-5-hydroxytoluene, and 3,5-diamino-o-cresol. They may be polyhydroxy and contain one or more primary amine groups or such substituent groups as alkyl, alkoxy, alkenyl, alkenyloxy, aryl, secondary or tertiary amino, and mercapto, e.g. methyl, methoxy, isopropyl, isopropenyl, methallyloxy, and butylamino. Their acid salts such as hydrochlorides may also be used. Sulphonyl chlorides include those of p-toluene, benzene, naphthalene, ethyl, and methyl. In examples: (1) to a slurry of 2,4-diaminophenol dihydrochloride in alcohol, mixed with aqueous sodium acetate solution, p-toluene sulphonyl chloride is added, the temperature rising from 53 DEG to 65 DEG C., 2,4-(p-toluene sulphonylamino) phenol separates on cooling; (2) a -aminophenol similarly yields o-(p-toluene sulphonylamino) phenol; (3) p-aminophenol and naphthalene b -sulphonyl chloride give p-(b -naphthalene sulphonylamino) phenol; (4) p-aminophenol and p-toluene sulphonyl chloride yield p-(p-foluene sulphonylamino) phenol; (5) 5-amino-1-naphthol similarly gives 5-(p-toluene sulphonylamino)-1-naphthol. These anti-oxidants are incorporated in a white moulded rubber compound in proportions of one part to 100 parts of pale crepe. Data showing the tensile and elongation at break before and after ageing are given. Proportions may vary from about 0.1 to 5 per cent and the compounds used in any type of rubber composition either natural or artificially prepared. The use in preserving rubber-like gums and artificial materials, unsaturated fatty, e.g. vegetable, oils, essential oils, petroleum oils and their derivatives, e.g. gasoline, soaps, aldehydes, and paints is also referred to.ALSO:Organic substances which deteriorate by absorption of oxygen from the air are preserved by incorporation of a sulphonyl amino phenol or naphthol of the formula (OH)x-R-(NH-SO2-R1)n, where R is an aromatic nucleus, R1 is an alkyl or aryl group, and x and n are integers. These anti-oxidants may be prepared by reacting amino phenols (or naphthols) with sulphonyl chlorides in the presence of a neutralizing base such as sodium acetate or carbonate. Solvents such as alcohol, acetone, methyl ethyl ketone, dioxane or benzene may also be present. Amino phenols specified are pm- and o-aminophenol, 2,4-and 3,4-diaminophenol, 5-amino-1-naphthol, 1,6-diamino-2-naphthol, 2-amino- and 2,4-diamino-resorcinol, 2-amino-5-hydroxytoluene, and 3,5-diamino-o-cresol. They may be polyhydroxy and contain one or more primary amine groups or such substituent groups as alkyl, alkoxy, alkenyl, alkenyloxy, aryl, secondary or tertiary amino, and mercepto, e.g. methyl, methoxy, isopropyl, isopropenyl, methallyloxy, and butylamino. Their acid salts such as hydrochlorides may also be used. Sulphonylchlorides include those of p-toluene, benzene, naphthalene, ethyl and methyl. In examples (1) to a slurry of 2,4-diaminophenol dihydrochloride in alcohol, mixed with aqueous sodium acetate solution, p-toluene sulphonyl chloride is added, the temperature rising from 53 to 65 DEG C. 2,4-(p-toluene sulphonyl-amino) phenol separates on cooling; (2) o-aminophenol similarly yields o-(p-toluene sulphonylamino) phenol; (3) p-aminophenol and naphthalene b -sulphonyl chloride give p-(b -naphthalene sulphonylamino) phenol; (4) p-amino-phenol and p-toluene sulphonyl chloride yield p-(p-toluene sulphonylamino) phenol; (5)5-amino-1-naphthol similarly gives 5-(p-toluene sulphonyl-amino)-1-naphthol. There anti-oxidants are incorporated in a white moulded rubber compound in proportions of one part to 100 parts of pale crepe. Data showing the tensile and elongation at break before and after ageing are given. Proportions may vary from about 0.1 to 5 per cent and the compounds used in any type of rubber composition either natural or artificially prepared. The use in preserving rubber-like gums and artificial materials, unsaturated fatty, e.g. vegetable, oils, essential oils, petroleum oils and their derivatives, e.g. gasoline, soaps, aldehydes, and paints is also referred to.
GB14822/42A 1942-01-03 1942-10-22 Improvements in antioxidants Expired GB560958A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US560958XA 1942-01-03 1942-01-03

Publications (1)

Publication Number Publication Date
GB560958A true GB560958A (en) 1944-04-28

Family

ID=22002113

Family Applications (1)

Application Number Title Priority Date Filing Date
GB14822/42A Expired GB560958A (en) 1942-01-03 1942-10-22 Improvements in antioxidants

Country Status (1)

Country Link
GB (1) GB560958A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE961624C (en) * 1953-04-22 1957-04-11 Ici Ltd Process for the preparation of 2,2-dioxy-5, 5'-dimethyldiphenylmethane derivatives and their salts

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE961624C (en) * 1953-04-22 1957-04-11 Ici Ltd Process for the preparation of 2,2-dioxy-5, 5'-dimethyldiphenylmethane derivatives and their salts

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