GB864276A - Metallized azo dyestuffs containing triazole rings - Google Patents

Abstract

The invention comprises metallized azo dyes of formula: <FORM:0864276/IV(c)/1> wherein R is the residue of an amino-naphthalene coupling component in which the nitrogen atoms are in o-position to one another. R1 is the radical of an azo component which may contain further azo groups having the -O-Me-group in o-position to the azo group, Me is copper, chromium, manganese, iron, cobalt or nickel, n is 1 or 2 and the group <FORM:0864276/IV(c)/2> is an azo or azoxy group, in admixture with the corresponding symmetrical dyestuffs. The copper complexes of the dyestuff mixture may be prepared by reductive linkage, to form an azo or azoxy group, of a nitrotriazole compound prepared by coupling a diazotized 2-amino-6-nitro-naphthalene-sulphonic acid with an o-coupling naphthylamine and then triazolizing, and a nitroazo dye prepared by coupling a diazotized 2-amino-6-nitronaphthalene-sulphonic acid with an azo component coupling ortho to a hydroxyl group and subsequent oxidizing coppering. The triazolation and/or oxidizing coppering steps may be carried out at the end of the process. The copper complex may be demetallized and the other metal complexes formed by treating the dyestuff mixture with suitable metallizing agents in substance or on the fibre. The dyestuffs give green shades on cellulose fibres. In an example an equimolar mixture of the triazolation product of 2-amino-6-nitro-naphthalene -4 : 8-disulphonic acid --> 2-amino-naphthalene-6-sulphonic acid (I) and the copper complex obtained by the oxidizing coppering of 2-amino-6-nitronaphthalene-4 : 8-disulphonic acid --> 2-naphthol-3 : 6-disulphonic acid (II) is reduced using glucose and aqueous sodium hydroxide solution. In further examples the azo component of (I) is 2-aminonaphthalene-5-mono- or -3 : 6-disulphonic acid or 1-aminonaphthalene-4-sulphonic acid and the azo component of (II) is 1-chloro- 2-acetylamino- 5-naphthol- 7-sulphonic acid, 1-naphthol- 4-sulphonic acid, phenol- 4-sulphonic acid, 1-(41 : 81-disulphonaphthyl-(21))-3-methyl- 5-pyrazolone and 1-chloro- 2-amino-5-naphthol- 7-sulphonic acid --> 2-naphthol-3 : 6-disulphonic acid. Specifications 660,447 and 721,495 are referred to.