GB1341320A - Water-soluble fibre-reactive azo dyestuffs their metal complex compounds and processes for their manufacture - Google Patents

Abstract

1341320 Water-soluble fibre-reactive azo dyestuffs FARBWERKE HOECHST AG 23 Dec 1971 [28 Dec 1970] 60063/71 Heading C4P [Also in Division C2] Novel water-soluble, fibre-reactive azo dyestuffs of the formula (wherein D is the radical of a diazo component; R is H or alkyl; n is 1 or 2; A is optionally substituted naphthylene or mono- or di-substituted phenylene; and Z is -SO 2 CH = CH 2 or -SO 2 CH 2 CH 2 X in which X is a radical capable of being split off by an alkaline agent) and their metal complexes are prepared by reacting compounds of the formula in any desired order with a diazonium salt of an appropriate amine DNH 2 and a compound of one of the formulµ OCN-A-Z and in which Z may also be -SO 2 (CH 2 ) 2 OH and Y is a halogen atom or a phenoxy group. In the products or intermediates Z groups may be interconverted and/or metal complexes may be formed. D may be, for example, a radical of the benzene, naphthalene, azobenzene, azonaphthalene, benzene-azo-naphthalene, diphenyl or stilbene series which may be substituted by water-solubilizing groups and/or other substituents, including heterocyclic radicals. X may be, for example, a halogen atom, an alkyl- or aryl-sulphonyloxy group, an acyloxy group, e.g. acetoxy, -OPO 3 H 2 , -SSO 3 H, -OSO 3 H, phenoxy or dialkylamino. The process for preparing (1) may be conducted by coupling the diazonium compounds with the aminonaphthols (4) or their N-acylates, with subsequent hydrolysis if N-acylates are used, and then reacting the products of the formula with the isocyanates or carbamic acid derivatives, or by reacting the latter with (4) and then reacting the products with the diazonium compounds. Metal derivatives may be formed by standard procedures from the intermediates (8) or the final products. Z groups are interconverted by standard procedures, e.g. groups are converted to -SO 2 CH = CH 2 with alkaline agents; -SO 2 CH = CH 2 or may be reacted with a dialkylamine or a thiosulphate to give -SO 2 (CH 2 )N(alkyl) 2 or respectively; and -SO 2 (CH 2 )OH may be esterified, e.g. -SO 2 (CH 2 )OSO 3 H, or -SO 2 (CH 2 ) 2 Cl. Starting materials.-1 - Aminobenzene - 3- sulphonic acid is diazotized and coupled with 1-amino-8-hydroxy-naphthalene-3,6-disulphonic acid at pH 7 to 7À5 to give a dyestuff starting material. Similarly 1-amino-benzene-2,5-disulphonic acid is diazotized and coupled with 2 - (N - acetylamino) - 5 - hydroxynaphthalene- 7-sulphonic acid and the acetyl group is removed from the product by acid hydrolysis.