GB819841A - Copper-containing disazo dyestuffs - Google Patents

Abstract

The invention comprises the copper complexes of disazo dyestuff of formula <FORM:0819841/IV (c)/1> wherein R is a naphthalene radical, R1 is an aromatic radical linked in the p-positions, R2 is a naphthalene radical having the hydroxyl group ortho to the azo group and R3 is an aromatic radical having a metallizable group such as a hydroxy, alkoxy or carboxy group ortho to the azo group. The unmetallized dyes are obtained by diazotizing an amine R3.NH2 and coupling with a suitable unsymmetrical urea, which may be obtained from the amines R4-N=N-R1-NH2 and H2N-R2-OH with the other or, in admixture with symmetrical ureas, by phosgenation of a mixture of the amines. Coppering of the disazo dyes is carried out in known manner. The coppered dyes dye cotton and regenerated cellulose in reddish brown, Bordeaux red to reddish violet shades. In examples: (1) the mixed urea obtained from the phenylurethane of 2-(41-amino - 61 - methylbenzene - 11 - azo) - naphthalene-4 : 8-disulphonic acid and 2-amino-5-naphthol-7-sulphonic acid is coupled with the diazo compound from 1-amino-2-hydroxy-3-chlorobenzene-5-sulphonic acid in aqueous pyridine, the dyestuff is isolated, dissolved in water and coppered by heating with copper sulphate; (2) the mixed urea obtained from the phenylurethane of 1-(41-amino-31-methoxy-61-methylbenzene - 11 - azo) - 8 - (benzenesulphonyloxy)-naphthalene - 3:6 - disulphonic acid and 2 - amino - 5 - naphthol - 7 - sulphonic acid is coupled with the diazo compound from 1-amino-2 - hydroxy - 3 - chlorobenzene - 5 - sulphonic acid, 1 - amino - 2 - hydroxy - 5 - chlorobenzene, or 1 - amino - 2 - methoxybenzene - 5 - sulphonic acid, the benzenesulphonic acid ester group is saponified by treatment with aqueous caustic soda and the dyestuff coppered (the benzenesulphonyl group may also be removed before the coupling); (3) the mixed urea obtained from the phenylurethane of 1-(41-amino-31:61-dimethylbenzene - 11 - azo) - 8 - (benzenesulphonyloxy) - naphthalene - 3:6 - disulphonic acid and 2-amino-5-naphthol-7-sulphonic acid is coupled with the diazo compound from 1-amino - 2 - hydroxy - 3 - nitrobenzene - 5 - sulphonic acid or 2-amino-1-naphthol-4-sulphonic acid and then treated as in (2); (4) the mixed urea obtained from the phenylurethane of 1-(41-amino-31:61-dimethylbenzene -11-azo1-8-(benzenesulphonyloxy) - naphthalene - 3:6-disulphonic acid and 2-amino-8-naphthol-6-sulphonic acid is coupled with the diazo compound from 1 - amino - 2 - hydroxy - 3 - chlorobenzene-5-sulphonic acid and then treated as in (2); (5) the mixed urea obtained from the phenylurethane of 1-(41-amino-71-sulphonaphthalene - 11 - azo) - 8 - (benzenesulphonyloxy)-naphthalene-3:6-disulphonic acid and 2-amino-5-naphthol-7-sulphonic acid is coupled with the diazo compound from 2-amino-4-chlorobenzoic acid and then treated as in (2).