GB782759A - Improvements in or relating to derivatives of 1-amino-2-nitro-benzene-4-sulphonamide - Google Patents

Abstract

The invention comprises dyes for acetate rayon of the formula: <FORM:0782759/IV (b)/1> where R1 is an aliphatic, cycloaliphatic, or araliphatic radical or a radical of the benzene, naphthalene, or hydronaphthalene series which radical R1 may be further substituted, R2 is hydrogen or an aliphatic radical of not more than 3 carbon atoms which may be further substituted, R3 is an aliphatic, cycloaliphatic or araliphatic radical which may be further substituted or a radical of the benzene series of the formula: <FORM:0782759/IV (b)/2> where t is hydrogen, methoxy, ethoxy, alkyl and/or halogen, u is a direct binding or oxygen, r is hydrogen or hydroxy, V is alkoxy which may contain hydroxy or alkoxy, and when R1 is not aliphatic, V may also be hydroxy, n is one or two, R3 is different from R1, and R4 is hydrogen or an aliphatic radical which may be further substituted, with the provision that no watersolubilizing groups are present and that R1 or R3 represents or contains a cyclic radical. R1 and R2 may form together with N a heterocyclic ring, and in the case when R3 is a radical of the benzene series as defined above, V is only alkoxy which may contain hydroxy or alkoxy. The products are made by reaction of a sulphonamide of the formula: <FORM:0782759/IV (b)/3> where X is chlorine or bromine, with an amine of the formula: <FORM:0782759/IV (b)/4> Mixtures of starting materials may be employed, and the amines may be mixed with other mono- or bi-nuclear cycloaliphatic or aromatic amines. The reaction may be carried out in aqueous medium in presence of an acidbinding agent or excess of the amine. In examples (1) 1-chloro-2-nitrobenzene-4-sulphonic acid phenylamide is reacted with cyclohexylamine; (2) 1-chloro-2-nitrobenzene-4-sulphonic acid - di - (21 - hydroxyethyl) - amide is reacted with cyclohexylamine; (3) 1-amino-4-[21-(211-methoxy) - ethoxy] - ethoxybenzene, is reacted with 1-chloro-2-nitrobenzene-4-sulphonic acid - phenylamide; (4) 1 - amino - 4 - (- 2 hydroxy) - ethoxy - benzene is reacted with 1-chloro - 2 - nitrobenzene - 4 - sulphophenylamide; (5) cyclohexylamine is condensed with a mixture of 1-chloro-2-nitrobenzene-4-sulphonic acid-phenylamide, dimethylamide and benzylamide. A dyeing example using acetate rayon is given, and a number of alternative starting materials and combinations thereof are listed.