Patent GB-951113-A (GB)
Title: Mono-azo dyestuffs and their metal complex compounds
IPC: C09B62/085
Filed: 1960-09-05
Abstract: The invention comprises monoazo dyes of formula <FORM:0951113/C3/1> wherein A, B, D and E are hydrogen atoms or substituents, R is an alkyl radical or an unsubstituted or substituted aryl radical or a carboxylic acid group, X is a direct linkage or the group >C=O, Y is a metal complex-forming group or a group or atom which can be transformed during the metallization process into such a group and W is a benzene residue having Y in o-position to -N = N-; and the metal complexes thereof.  The dyes are prepared by diazotizing an amine of formula <FORM:0951113/C3/2> and coupling with a suitable pyrazolo-benzimidazole or -quinazolone.  Alternatively, a 41-aminopyrazolo-benzimidazole or -quinazolone may be diazotized and coupled with an azo component of the benzene or naphthalene series. The dyes may be metallized by the usual methods in substance; chromium, cobalt, copper and nickel being specified metals.  The insoluble dyes may be used as pigments and the water-soluble dyes to dye wool, synthetic polyamides and polyurethanes in yellow, red and blue shades.  In Examples:  (1) the monoazo dye 1-amino-2-hydroxybenzene-5-sulphonamide --> 31 - methyl - pyrazolo - (11,51: 1,2)-benzimidazole is prepared and the 2:1-chromium complex formed by heating in an aqueous solution of potassium bichromate and glucose; (2) wool is dyed from an acid bath with the dye 1-amino-2-hydroxy-3-chlorobenzene - 5 - sulphonic acid --> 31 - methylpyrazolon - (11,51:1,2) - benzimidazole, potassium bichromate is added to the bath which is boiled to form the chromium complex on the fibre; (3) the copper complex of the dye 1 - amino - 2 - phenol - 3,5 - disulphonic acid --> 31 - methyl - pyrazolo (11,51:3,2) - 7 -aminoquinazolone is condensed with cyanuric chloride to give the dichlorotriazinylamino derivative which may be used to dye cotton in the presence of an alkali. Further examples of metallized, including cobalt complexes, and metal-free monoazo dyes are specified. Specifications 740,589, 758,016, 918,128 and 951,114 are referred to.ALSO:The metallisation on the fibre of monoazo dyes of formula <FORM:0951113/D1-D2/1> wherein A, B, D and E are hydrogen atoms or substituents, R is an alkyl radical or an unsubstituted or substituted aryl radical or carboxylic acid group, X is a direct linkage or the group > C = 0, Y is a metal complex-forming group or a group or atom which can be transformed during the metallisation process into such a group and W is a benzene residue having Y in o-position to -N=N-, is described.  Specified metallising agents are salts of copper, nickel, chromium and cobalt.  In examples the dyes 1-amino-2-hydroxy-3-chloro-benzene-5-sulphonic acid or 5-sulpho-anthranilic acid --> 31-methyl-pyrazolo-(11, 51 : 1, 2)-benzimidazole-31-carboxylic acid; 1-amino-2-hydroxy-3-chlorobenzene-5-sulphonic acid --> 31-methyl-pyrazolo-(11, 51 : 3, 2)-quinazolone and 5-sulpho-anthranilic acid --> 2-(31-nitrophenyl)-pyrazolo-(11, 51 : 3, 2)-quinazolone are used to dye wool and the dyed fibre is after-chromed with potassium bichromate.  Specification 951,114 is referred to.