Patent GB-749308-A (GB)
Title: Manufacture of triphenylmethane dyestuffs
IPC: C09B11/28
Filed: 1952-12-30
Abstract: Asymmetrical triphenylmethane dyes are made by reacting, at raised temperature, with a primary or secondary amine other than a diarylamine, a compound of the formula:- <FORM:0749308/IV(c)/1> in which R1 represents hydrogen or an aliphatic or cycloaliphatic radical, R2 represents an aromatic radical, and X represents halogen or alkoxy, and in which the benzene nucleus carrying the sulpho group may contain substituents prepared according to Specification 749,908. The invention includes the products of the formula:- <FORM:0749308/IV(c)/2> in which R1 and R3 each represent hydrogen or an aliphatic or cycloaliphatic radical, R2 is an aromatic radical, and R4 is an acyclic, isocyclic or heterocyclic radical, in which the benzene nucleus carrying the sulpho group may contain substituents e.g. halogen, alkoxy, carboxy, or sulpho in 41-position and group <FORM:0749308/IV(c)/3> is different from <FORM:0749308/IV(c)/4> The products may be sulphonated.  In examples, compounds of the first of the above formula in which X is chlorine and in which the radical <FORM:0749308/IV(c)/5> is the radical of the first of each of the following pairs of amines, are each reacted with the second amine of the same pair, the phenyl radical containing the sulpho group being otherwise unsubstituted or substituted para to the central carbon atom as indicated in squared brackets, (1) p-anisidine and 1-amino -4- methoxybenzene -3- sulphonate, (2) 1-amino -2- hydroxybenzene -3- carboxylic acid and 4-aminodiphenylamine -2- sulphonic acid, (3) o-trifluoromethylaniline and 2, 6-dimethyl-aniline, (4) o-trifluoromethylaniline and sodium methylamino ethane-sulphonate, (5) 2-amino-N-ethyl-carbazole and sodium methylamino ethane-sulphonate, (6) 2, 4, 6-trimethylaniline and 1-amino -4- cyclohexylbenzene, (7) 2-amino-N-ethylcarbazole and 1-amino -2- hydroxy -5- sulpho -3- benzoic acid, (8) 1-amino -4- hydroxybenzene -3- carboxylic acid and sodium 1-amino -2- hydroxy -5- sulpho -3- benzoate, (9) sodium 1-amino -2- hydroxy -3- carboxy -5- benzene sulphonate and p-phenetidine, (10) sodium 1-amino -2- hydroxy -3- carboxy -5- benzene sulphonate and 1-amino -2- hydroxy-benzene -3- carboxylic acid, (11) o-methyl -N- methylaniline and sodium 1-amino -4- hydroxybenzene -3- sulphonate, [sulpho] (12) o-methyl-N-methyl-aniline and sodium 1-amino-4-methylbenzene-3-sulphonate [sulpho], (13) o-methyl-N-methyl-aniline and sodium 1-amino -4- hydroxy -3- benzoate [sulpho], (14) aniline and sodium 1-amino -4- hydroxybenzene -3- sulphonate [sulpho], (15) 2, 6-dimethylaniline and sodium 1-amino -4- hydroxybenzene -3- sulphonate [methoxy], (16) 2, 4, 6-trimethylaniline and 1-amino -4- methylbenzene -3- sulphonic acid [carboxy], (17) p-anisidine and sodium 1-aminobenzene -4- sulphonate, (18) p-aminoacetanilide and sodium 1-aminobenzene -4- sulphonate, (19) 1-amino -2- methoxy -N- diethyl-sulphonamide-benzene and sodium 1-aminobenzene -4- sulphonate, (20) aniline and sodium 1-aminobenzene -4- sulphonate, (21) 2. 6-dimethylaniline and sodium methylamino ethane sulphonate, (22) p-aminoazobenzene and sodium methylamino ethane sulphonate, (23) 1-aminobezene -4- (2-hydroxyethyl)-sulphone and 2, 6-dimethylaniline, (24) 4-amino -3- methyl-diphenyl and 2, 2, 6-dimethylaniline, (25) 2-methyl -6- chlor-aniline and 2, 6-dimethylaniline, (26) 4-amino -3- methyl-diphenyl and sodium 1-amino -4- methoxybenzene -3- sulphonate, (27) p-anisidine and diethylamine, (28) N-methylaniline and diisobutylamine, (29) N-ethylaniline and n-butylamine, (30) 2-methyl -N- ethylaniline and 1-amino-2, 6-dimethylbenzene, (31) N-ethylaniline and N-butyl-aniline, (32) N-butylaniline and p-phenetidine, (33) N-ethylaniline and sodium 1-aminobenzene -2- sulphonate [chlorine], (34) 4-amino -2- sulpho-diphenylether and p-phenetidine [chlorine], (35) p-anisidine and 2, 4, 6-trimethylhexahydroaniline, (36) N-methylanline and 1, 2, 3, 4-tetrahydro -1- naphthylamine, (37) N-ethylaniline and N-cyclohexyl -otoluidine, (38) N-methylaniline and cyclohexylamine.  Other starting materials are referred to.  The products dye wool or silk blue to red shades. Specification 744,972 is referred to.