Patent GB-824327-A (GB)
Title: Improvements relating to polyazo dyestuffs containing triazole rings and their use
IPC: C09B43/06
Filed: 1956-06-26
Abstract: The invention comprises polyazo dyestuffs of formula <FORM:0824327/IV(c)/1> which contain 2 to 5 sulphonic acid groups, and wherein R1 is a radical of the benzene or naphthalene series which may contain an arylazo group para to the azo linkage or a radical of the aryltriazole or arylthiazole series, R2 is a paraphenylene or -naphthylene radical, R3 is a paraphenylene radical and R5 is an isocyclic or heterocyclic radical bound by neighbouring carbon atoms to the triazole ring.  The dyestuffs are prepared by oxidizing polyazo dyestuffs of formula R1-N=N-R2-N=N-R3-N=N-R4 which contain 2 to 5 sulphonic acid groups and wherein R1, R2 and R3 are as defined above and R4 is the radical of an azo component coupling ortho to a primary amino group.  The oxidation is carried out in aqueous alkaline solution preferably with warming, using, for example, cuprammine compounds or alkali metal hypochlorites as oxidizing agent and possibly introducing air or oxygen.  Specified components, other than those in examples, from which the dyes of the above formul  are derived by successive diazotization and coupling are:-(R1) m- or p-aminobenzoic acid, aniline-2 : 4-disulphonic acid, 4-chloroaniline-3-sulphonic acid, 4 : 6-dimethylaniline-2-sulphonic acid, 5-aminosalicylic acid, 5-amino-3-sulphosalicylic acid, 4-aminodiphenyl - 3 - sulphonic acid, 41 - acetylamino - 4 - aminodiphenyl - 3 - sulphonic acid, 4-nitro- or -acetylamino-41-aminostilbene-2 : 21-disulphonic acids, 1-aminonaphthalene-5-, -6-or -7-sulphonic acid, 2-aminonaphthalene-6- or -7-sulphonic acid, 2-(41-aminophenyl)-5-methylbenzthiazole-21-mono- and -6 : 21-di-sulphonic acids, 2 - (41 - aminophenyl) - naphthotriazole-or-naphthothiazole-5 : 7-disulphonic acid, and 4 - (naphthotriazolyl - 2) - 41 - aminostilbene - 2 : 21-disulphonic acid; (R2 and R3) o-toluidine 2 : 5-dimethyl- or -dimethoxy-aniline and 2-methoxy- or -ethoxy-1-aminonaphthalene-6-sulphonic acid; (R4) 2 : 4-diamino-toluene, 2 : 4-diamino - benzenesulphonic acid, 5 - amino - 2 - methoxy - 1 - methylbenzene, 2 - aminonaphthalene - 5 : 7 - disulphonic acid, 2 - aminonaphthalene-3-carboxylic acid, 2-amino-3-carboxy - naphthalene - 6 - sulphonic acid, 2 - aminoanthracene and 5-amino-2-phenyl-benztriazole-31- or -41-sulphonic acid.  The watersoluble alkali metal salts of the dyes may be used to dye cellulose materials in orange to orange-brown shades.  In examples: (1) the amino-trisazo dye, 2-aminonaphthalene-4 : 8-disulphonic acid --> m-toluidine --> m-toluidine --> 2-aminonaphthalene-6-sulphonic acid is prepared and oxidized with aqueous copper sulphate and ammonia or with sodium hypochlorite solution to give the corresponding disazo-triazole compound, and other dyes obtained from the above and the following additional components are similarly prepared and oxidized; starting components:-2 - aminonaphthalene - 3 : 6-, -5 : 7- or -6 : 8-disulphonic acid, 1-aminonaphthalene-4-mono- or -3 : 6-disulphonic acid, dehydrothio-p-toluidine sulphonic acid, aniline-3- or -4-mono- or -2 : 5-di-sulphonic acid, 1-amino - 2 : 4 - dimethylbenzene - 6 - sulphonic acid and 1-amino-3-carboxy-4-hydroxybenzene-5-sulphonic acid; first middle component:-3-acetylamino- or -sulphoacetylamino-aniline, o-anisidine, 2-methoxy-5-methylaniline, aniline, alpha-naphthylamine and 1-aminonaphthalene-6- or -7-sulphonic acid; second middle component:-3-acetylamino- or -sulphoacetylamino- or -carbomethoxyamino-aniline, o- or m-anisidine and 2-methoxy-5-methylaniline; end component:-beta - naphthylamine, 1 - aminonaphthalene-3- or -4-sulphonic acid, 2-aminonaphthalene-1- or -5- or -7-mono- or -3 : 6-disulphonic acid, 5-amino-benztriazole or -benzthiazole, p-aminosalicylic acid, 3-methoxy-4-methylaniline, 1 : 3-diaminobenzene, 1-phenyl-3-methyl-5-iminopyrazole, 2-amino-8-naphthol-6 - sulphonic acid, 2 - amino - 5 - naphthol - 7 - sulphonic acid and 1 : 3-diaminobenzene-4-sulphonic acid : (2) the amino-trisazo dye, 4-aminoazobenzene - 3 : 41 - disulphonic acid --> m-toluidine --> beta-naphthylamine is prepared and oxidized as in (1), and other dyes obtained from the above and the following additional components are similarly prepared and oxidized : starting components :-4-amino-41-hydroxy - 31 - carboxy - azobenzene - 3 - sulphonic acid, 4 - amino - 2 - methyl - 41 - hydroxy - 31 - carboxyazobenzene - 51 - sulphonic acid, 4 - amino - 2 - methyl - 5 - methoxy - 41 - hydroxy - 31 - carboxyazobenzene - 51 - sulphonic acid, 4 - amino - 3 : 21 - dimethylazobenzene - 5 : 41 - disulphonic acid, and 41-(411-aminophenyl)-4-hydroxy - 3 - carboxyazobenzene; middle component :-2-methoxy-5-methylaniline and 3-acetylamino - or - sulphoacetylamino - aniline; end component :-1 - aminonaphthalene - 3 - or -4-sulphonic acid, 2-aminonaphthalene-5- or -6-sulphonic acid, beta - naphthylamine, 3 - methooxy-4-methylaniline, and 2-amino-5-naphthol-7-sulphonic acid : (3) the aminotetrakisazo dye, 2 - aminonaphthalene - 4 : 8 - disulphonic acid --> m-toluidine --> m-toluidine --> 3-acetylaminoaniline --> 2-aminonaphthalene-6-sulphonic acid, is prepared and oxidized as in (1), and other dyes obtained from the above and the following additional components are similarly prepared and oxidized ; starting components:-1 - aminonaphthalene - 3 : 6 - disulphonic acid, 2-aminonaphthalene-5 . 7-disulphonic acid and 1-aminobenzene-3- or -4-mono-or -2 : 5-disulphonic acid; first middle component:-1 - aminonaphthalene - 6 - or - 7 - sulphonic acid and aniline; second middle component:-3 - acetylamino - or - methylamino-aniline, 2 - methoxy - 5 - methyl - aniline, 1 - aminonaphthalene-6-sulphonic acid and alpha-naphthylamine; third middle component:-m-toluidine; end component:-1-aminonaphthalene-3- or -4-sulphonic acid, beta-naphthylamine, and 2-aminonaphthalene-5-mono- or -3 : 6-di-sulphonic acid; the starting and first middle components are also specified together as the aminoazo compounds:-4-aminoazobenzene - 3 : 41 - disulphonic acid, 4 - amino - 41 - hydroxy - 31 - carboxyazobenzene - 3 - sulphonic acid and 4-amino-2-methylazobenzene-21 : 51-disulphonic acid.