Patent GB-560958-A (GB)
Title: Improvements in antioxidants
IPC: C08K5/43
Filed: 1942-10-22
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.