GB870985A - New complex metal compounds of monoazo-dyestuffs derived from cyanuric halides, their manufacture and use - Google Patents

Abstract

870,985. Monoazo triazine dyes. CIBA Ltd. Aug. 12, 1957 [Aug. 10, 1956; Oct. 17, 1956; Jan. 25, 1957], No. 25422/57. Class 2(4). The invention comprises complex metal compounds of #, #<SP>1</SP>-dioxy-monoazo dyes which contain at least two, and advantageously more than two carboxylic or sulphonic acid groups and contain bound through an N bridge a residue of formula:- where R is NH 2 or the residue of an organic monoamine bound to C through its amino group and having at most 13 C atoms and, if it is aromatic, is substituted by at least one carboxylic or sulphonic acid group as the sole salt-forming substituent or substituents present. The dyes may be made by treating a 2, 4, 6-trihalogen- 1, 3, 5-triazine with an appropriate metalliferous aminoazo dye and treating the product, with or without isolation, with ammonia or an appropriate monoamine. In some instances they may be made by metallizing appropriate dyes, e.g. when the triazine halogen is not affected by the metallization process. The amino group in the dye residue may be obtained by reducing nitro or hydrolysing acylamino groups. Preferred classes of the dyes are copper complexes and 1, 2-chromium and cobalt complexes of dyes containing two sulphonic acid groups and of formula:- where R is a chloro- or nitro-benzene residue with OH #- to the azo group and X is an amino group. Preferably the triazine residue is in the coupling component moiety of the dye. Copper, chromium, cobalt, nickel, manganese, iron and aluminium complexes are mentioned. 1, 1-Complexes of copper and nickel and 1, 2-complexes of chromium and cobalt are preferred. Representative of specified or indicated amines from which R is derived are:-methyl-, methoxypropyl-, cyclohexyl-, diethyl- and chloroethyl-amines, ethanolamines, aminocarbonic acid esters, aminoacetic acid ethyl esters, aminoethane sulphonic acid, #-aminobenzoic acid, m-aminobenzene sulphonic acid and aminonaphthalene mono-, di- and tri-sulphonic acids. Representative of specified or indicated amines comprising the diazo component of the dyes are:-chloro- and nitro- #-amino-phenols and #-aminophenol, mono- or di-sulphonic acids and representative of coupling components specified and indicated are m-aminophenol, 1-(41-aminophenyl)- 3-methyl- 5-pyrazolone, #-ketocarboxylic acid arylamides, 2-amino- 8-naphthol- 6-, 2-alkylamino- 5-naphthol- 7-, 2-(3<SP>1</SP>-aminobenzoylamino)- 5-naphthol- 7- and 2-(4<SP>1</SP>-aminophenylamino)- 5-naphthol-3<SP>1</SP>, 7- di-sulphonic acids. The dyes colour polyhydroxylated fibrous materials, e.g. wood pulp, regenerated cellulose, viscose, linen and cotton, especially when used with alkalis. Examples are provided of the preparation of the dyes and their use in dyeing processes, representative of the diazo components used additional to those indicated above being -6-acetylamino- 2-aminophenol- 4-sulphonic acid, 4-methyl- 2-aminophenol- 5-sulphonic acid and 1-amino- 2- naphthol- 4-sulphonic acid and amongst the pyrazolone coupling components used is one of formula:- Specifications 299,331, 797,946, 851,537, 852,120 and 863,754 are referred to.