Patent GB-895180-A (GB)
Title: Stabilization of organic substances subject to oxidative deterioration with metal deactivators
IPC: C08K5/353
Filed: 1960-06-07
Abstract: Fats and fatty oils, waxes, lubricating oils and greases, and liquid fuels such as gasoline which are subject to catalytic oxidative deterioration in the presence of metals, are stabilized by the incorporation of (a) up to 5% by weight of a metal deactivator of formula <FORM:0895180/III/1> wherein X is oxygen or sulphur, R1 is an o-hydroxyaryl radical, and R2-5 are each either hydrogen or alkyl radicals which preferably contain 1-4 carbon atoms, and usually also (b) an antioxidant, e.g. dibutyl cresol, bisphenols, butylated octylphenols, p-isopropoxy- or octylateddiphenylamines, polyalkyl polyphenols, hydroquinone monobenzyl ether, di-sec. butyl-, di-b -naphthyl-, or diphenyl-p-phenylene diamine, alkylated phenols, N-methyl- and N-butyl-2-dodecyl-4-aminophenol, aldol- or phenyl-b -naphthylamine, or tri(p-nonylphenyl) phosphite, usually in an amount of 0,0001-10 parts per 100 parts of substance to be stabilized.  In the preferred class of activators (a), x is sulphur and R1 is a hydroxyphenyl group which may be substituted with a halogen atom or a further hydroxy group.  An exhaustive list of suitable deactivators is given, but the one particularly favoured is 2-(2-hydroxyphenylamino)benzothiazole, which is used in Example 6 together with N-n. butyl-4-aminophenol and N:N1-dibutyl-4 phenylene diamine in a thermally cracked gasoline.  U.S.A. Specifications 2,181,121, 2,533,205 and 2,754,216 are referred to.ALSO:Natural rubber, butyl rubber, acrylonitrilebutadiene polymers, polychloroprenes, acrylic ester polymers, vinyl ester elastomers, butadienestyrene polymers, and other vinyl or styrene resins subject to catalytic oxidative deterioration in the presence of a metal, are stabilized by the incorporation of (a) up to 5% by weight of a metal deactivator of formula <FORM:0895180/IV (a)/1> wherein X is oxygen or sulphur, R1 is an o-hydroxyaryl radical, and R2-5 are each either hydrogen or alkyl radicals which preferably contain 1-4 carbon atoms, and (b) an antioxidant, e.g. dibutyl cresol, bisphenols, butylated octylphenols, p-isopropoxy diphenylamine, octylated diphenylamines, polyalkyl polyphenols, hydroquinone monobenzyl ether, di-sec. butyl-, di-b -naphthyl-, or diphenyl-p-phenylene diamine, alkylated phenols, N-methyl- and N-butyl-2-dodecyl-4-aminophenol, aldol- and phenyl-b -naphthyl-amine or tri(p-nonylphenyl) phosphite, usually in an amount of 0,0001-10 parts per 100 parts of substance to be stabilized.  In the preferred class of activators (a), X is sulphur and R1 is a hydroxyphenyl group which may be substituted with a halogen atom or a further hydroxy group.  An exhaustive list of suitable deactivators is given, but the one particularly favoured is 2-(2-hydroxyphenylamine)-benzothiazole which is used in Example 2 together with a styrenated phenol antioxidant in a butadienestyrene rubber.  U.S.A. Specifications 2,181,121, 2,533,205 and 2,754,216 are referred to.ALSO:Organic substances subject to oxidative deterioration in the presence of a metal containing material are stabilized by the incorporation of (a) up to 5% by weight of a metal deactivator of formula <FORM:0895180/IV (b)/1> wherein X is oxygen or sulphur, R1 is an o-hydroxy aryl radical, and R2-5 are each either hydrogen or alkyl radicals which preferably contain 1-4 carbon atoms, and (b) an antioxidant, e.g. dibutyl cresol, bisphenols, butylated octylphenols, p-isopropoxy diphenylamine, octylated diphenylamines, polyalkyl polyphenols, hydroquinone monobenzyl ether, di-sec. buty-, di-a -naphthyl-, and diphenyl-p-phenylene diamine, alkylated phenols, N-butyl- and N-methyl-2-dodecyl-4-aminophenol, aldol- and phenyl-a -naphthylamine, or tri(p-nonylphenyl)phosphite, usually in an amount of 0.0001-10 parts per 100 parts of substance to be stabilized.  In the preferred class of deactivators (a), X is sulphur and radical R1 is a hydroxyphenyl group which may be substituted with a halogen atom or a further hydroxy group.  An exhaustive list of suitable deactivators is supplied, but the one particularly favoured is 2-(2-hydroxy-phenylamino)benzothiazole.  2 - (2 - hydroxyphenylamino) benzathiazole is obtained by heating together 110 parts of 2-amino-phenol, 170 parts of 2-chlorobenzothiazole, and 500 parts of ethylene glycol at 150 DEG C.-165 DEG C. for 1 hour then cooling, adding 1,000 parts of water, and filtering off the crystalline product which separates. U.S.A. Specifications 2,181,121, 2,533,205 and 2,754,216 are referred to.