Patent GB-866386-A (GB)
Title: Metallized disazo dyestuffs containing triazole rings
IPC: C09B31/02
Filed: 1958-07-17
Abstract: Aminonaphthotriazoles are prepared by coupling a diazotised 2-amino-6-nitronaphthalene sulphonic acid with a naphthylamine coupling ortho to the amino group, triazolising and reducing the nitro group to amino, and are used in the preparation of azo dyes (see Group IV(c)).  The triazolation may be carried out using ammoniacal cupric salt solution or sodium hypochlorite solution. In an example the aminotriazole compound of formula:  <FORM:0866386/IV (b)/1> obtained by the process specified above from 2-amino-6- nitronaphthalene- 4 : 8- disulphonic acid and 2-aminonaphthalene-6-sulphonic acid is specified.  Further starting materials specified are 2-amino-6-nitronaphthalene-4- or p -8-sulphonic acid and 2-aminonaphthalene, 2-aminonaphthalene-5- or -7-mono- or -3 : 6-disulphonic acid and 1-aminonaphthalene-4-sulphonic acid.ALSO:The invention comprises the nickel and copper complexes of disazo dyes of formula:- <FORM:0866386/IV(c)/1> wherein R is an azo component radical having the hydroxy group in ortho-position to the azo group, R1 is a 1 : 4-phenylene or -naphthylene radical having X in ortho-position to the external azo group, X is a metallizable group or a group or atom convertible thereto under metallizing conditions, R2 is a 1 : 2-naphthylene radical and n is 1 or 2.  They are prepared by coupling a diazotized 2-amino-6-nitronaphthalene sulphonic acid with a naphthylamine coupling ortho to the amino group, triazolizing the aminoazo compound, reducing the nitro group to an amino group, diazotizing the aminotriazole and coupling in p-position to the amino group of an azo component having an amino group with a suitable group or atom (cf. X above) ortho thereto, further diazotizing and coupling ortho to the hydroxy group of an azo component (R) and metallizing with copper or nickel-yielding agents.  Other processes wherein the various reactions are carried out in a different order are specified. The dyes give green shades on natural or regenerated cellulose.  In an example the aminotriazole compound obtained by triazolizing and reducing the nitro group of the aminoazo compound 2-amino-6-nitronaphthalene-4 : 8-disulphonic acid (I) --> 2-aminonaphthalene-6-sulphonic acid (II) is diazotized and coupled with 1-amino-2-ethoxy-naphthalene-6-sulphonic acid (III), the aminoazo dye is diazotized and coupled with 2-naphthol-3 : 6-disulphonic acid (IV) and finally coppered.  Further starting materials specified in examples and the general description are:-(I) 2-amino-6-nitro-naphthalene-4- or -8-sulphonic acid; (II 2-aminonaphthalene, 2-aminonaphthalene-5- or -7-mono- or -3 : 6-di-sulphonic acid, 1-amino-naphthalene-4-sulphonic acid; (III) aniline, o-anisidine, 5-methyl-2-methoxyaniline, 1-amino-naphthalene, 2-chloro-1-aminonaphthalene-6- or -7-sulphonic acid, anthranilic acid, 1-amino-2-ethoxynaphthalene-7-sulphonic acid; (IV) p-cresol, 2-naphthol-4- or -5- or -6-sulphonic acid, 1-hydroxy-8-acetyl- or -benzoyl-aminonaphthalene-5-sulphonic acid, 1-naphthol-4-sulphonic acid, 1-naphthol-3 : 8- or -4 : 8-disulphonic acid, 2-naphthol-5 : 7-disulphonic acid, 1-chloro-2-acetylamino-5-naphthol-7-sulphonic acid, 1-hydroxy-7-acetyl- or -phenyl-aminonaphthalene-3-sulphonic acid, 1-phenyl- or -(41-sulphophenyl)-3-methyl-5-pyrazolone. Specifications 660,447, 721,495 and 790,386 are referred to.