Patent GB-1215890-A (GB)
Title: Phenolic antioxidants
IPC: D06M13/402
Filed: 1968-09-19
Abstract: 1,215,890. Phenolic antioxidant. J. G. GEIGY A.-G. 19 Sept., 1968 [20 Sept., 1967], No. 44632/68. Heading C2C. [Also in Divisions C3 and D1] The invention comprises compounds of general formula wherein A represents a sterically hindered phenol of the benzene series, Y is a linking group containing a carboxylic acid amide group, Z is an aliphatic or carbocyclic aromatic radical, the latter containing at most two mono- or bicyclic nuclei, W is a sulphonic acid group, and m and n each represent 1 or 2. These compounds are prepared by treating a compound of formula with a co mpound of formula wherein one of P and Q represents the group the other represents when y is 1, V represents an -oAr group and when y = 0 it represents a chlorine or bromine atom; Ar is an aromatic radical of the benzene or naphthalene series, R 2  and R 3  each represent hydrogen or an optionally substituted alkyl group, X, X<SP>1</SP> independently represent alkylene, oxa-alkylene or thia-alkylene and x, x<SP>1</SP> and y each represent 0 or 1. In Examples 1-34 the following compounds are prepared: (1) 1-N-(4- hydroxy - 3,5 di - tert. butyl - phenyl acetyl)- naphthylamine - 4 - sulphonic acid; (2) N- (4 - hydroxy - 3,5 - di - tert. butyl - benzyl mercaptoacetyl) - aniline - 3 - sulphonic acid; (3) N - (4 - hydroxy - 3,5 - di - tert. butyl benzoyl)- aniline - 3 - sulphonic acid; (4) 1 - N - (2- hydroxy - 3,5 - dimethyl - benzoyl) - naphthylamine - 4 - sulphonic acid; (5) 1 - N - (# - 4- hydroxy - 3,5 - di - tert. butylphenylpropionyl)- naphthylamine - 8 - sulphonic acid; (6) N - (#- 4 - hydroxy - 3,5 - di - tert. butyl - phenyl propionyl) - aniline - 3 - sulphonic acid; (7) N - (# - 4 - hydroxy - 3,5 - di - tert. butylphenylpropionyl) - aniline - 2 - sulphonic acid; (8) 2 - N - (# - 4 - hydroxy - 3,5 - di - tert. butyl phenyl propionyl) - amino - diphenyl ether - 4- sulphonic acid; (9) N - (3 - sulphophenyl)- N<SP>1</SP> - (3,5 - di - tert. butyl - 4 - hydroxyphenyl)- urea; (10) N - (S - sulpho - 2 - naphthyl) - N<SP>1</SP> (3,5 - di - tert. butyl - 4 - hydroxyphenyl) urea; (11) 2 - # - phenylethyl - 5 - # - (4 - hydroxy - 3,5- di - tert. butyl phenyl) - propionylaminobenzene sulphonic acid; (12) N - (4 - hydroxy- 3,5 - di - tert. butylphenylpropionyl) - N - methyl - 2 - aminoethane sulphonic acid; (13) 2- N - (# - 4 - hydroxy - 3,5 - di - tert. butylphenylpropionyl) - aminoethane sulphonic acid; (14) 2 - # - (4 - hydroxy - 3,5 - di - tert. butylphenylpropionyl amino) - 4,4<SP>1</SP> - dichlorodiphenyl ether- 2<SP>1</SP> - sulphonic acid; (15) 1,4 - bis - (# - 4 - hydroxy - 3,5 - di - tert. butylphenyl) - propionylaminonaphthalene - 6 - sulphonic acid; (16) 2- (# - 4 - hydroxy - 3,5 - di - tert. butylphenyl)- propionylamino - 2<SP>1</SP>,4<SP>1</SP> - dichlorodiphenyl ether- 4 - sulphonic acid; (17) 1 - (# - 4 - hydroxy- 3,5 - di - tert. butylphenyl) - propionylamino- 2 - methoxynaphthalene - 6 - sulphonic acid; (18) 2 - (# - 4 - hydroxy - 3,5 - di - tert. butylphenyl) - propionylamine - 2<SP>1</SP>- methyldiphenyl ether - 4 - sulphonic acid; (19) 4 - # - (4- hydroxy - 3,5 - di - tert. butylphenyl) - propionyl - aminostilbene - 2 - sulphonic acid; (20) N - (4 - hydroxy - 3,5 - di - tert. butylphenyl) - N<SP>1</SP> methyl - N<SP>1</SP>(2 - sulphoethyl)- urea; (21) N - (4 - hydroxy - 3,5 - di - tert. butylphenyl) - N<SP>1</SP> - (2 - sulphoethyl) - urea; (22) 4 - sulphobenzoic acid - (4 - hydroxy - 3,5 - di. tert. butyl) - anilide; (23) 2 - N - [# - (4- hydroxy - 3,5 - di - tert. butylphenyl) - propionyl] - naphthylamine - 6 - sulphonic acid; (24) 1 - N - [# - (4 - hydroxy - 3,5 - di - tert. butylphenyl) - propionyl] - naphthylamine - 4- sulphonic acid; (25) 1 - [S - (4 - hydroxy - 3,5- di - tert. butyl benzyl) - thioacetylamino]- naphthalene - 4 - sulphonic acid; (26) 1 - (2- hydroxy - 3 - tert. butyl - 5 - methylbenzoylamino) - naphthalene - 4 - sulphonic acid; (27) N - (# - 4 - hydroxy - 3,5 - di - tert. butylphenylpropionyl) - aniline - 4 - sulphonic acid; (28) 2 - (4 - hydroxy - 3,5 - di - tert. butylphenylacetamido) - naphthalene - 5 - sulphonic acid; (29) N - (2 - hydroxy - 3 - tert. butyl - 5 - methylbenzyl) - N - ethyl - p - sulphobenzoamide; (30) 4 - [# - (4 - hydroxy - 3,5 - di - tert. butylphenyl) - propionylamido] - diphenyl ether - 3- sulphonic acid; (31) N - [# - (4 - hydroxy- 3,5 - di - tert. butylphenyl) - propionyl] - N- ethyl - sulphanilic acid; (32) 1 - [# - (4 - hydroxy - 3,5 - di - tert. butylphenyl) - propionylamido] - naphthalene - 5 - sulphonic acid; (33) N - [# - (4 - hydroxy - 3,5 - di - tert. butylphenyl)- propionyl] - aniline - 4 - sulphonic acid; (34) 1- N - [# - (4 - hydroxy - 3,5 - di - isopropylphenyl)- propionyl] - naphthylamine - 4 - sulphonic acid.