GB1017869A - Anthraquinone dyestuffs - Google Patents

Abstract

The invention provides anthraquinone dyes of general formula <FORM:1017869/C4-C5/1> in which R is an unsubstituted or substituted hydroxy-phenyl or alkoxy-phenyl radical, R2 is a hydrogen or halogen atom or an aryl mercapto, alkylmercapto, cyano or carbodialkyl amide group and R3 and R4 which may be the same or different are hydrogen, halogen or nitro groups. These dyes are obtained by heating cyclic sulphimides of general formula <FORM:1017869/C4-C5/2> in which R1-R4 are as above, in a high boiling (generally 150-200 DEG C.) polyhydric aliphatic alcohol or ether thereof as solvent. Such solvents include ethylene glycol, diethylene glycol, diethylene glycol monomethyl or monoethyl ether, glycerol or butane 1,4-diol. The sulphimides of Formula II above may be prepared in the reaction mixture from the corresponding sulphamide of formula <FORM:1017869/C4-C5/3> in which R1-R4 are as above, by the addition of an oxidizing agent, e.g. ferric salts. The sulphimides in which R2 is other than hydrogen may be produced by reacting compounds of formula <FORM:1017869/C4-C5/4> R1 is as above, X and Y are the same or different being hydrogen, halogen or nitro, with compound of formula R2H to give the sulphamide substituted by R2 which is then oxidized to the corresponding sulphamide having Formula IV <FORM:1017869/C4-C5/5> These compounds of Formula IV may also be produced by reacting cyclic sulphimides of 1,4-diamino-anthraquinones, optionally substituted in the 5 or 8 positions by halogen or nitro groups, in the presence of acid catalysts (H2SO4.AlCl3) with phenols or phenyl ethers, followed by oxidation of the sulphamides obtained to the sulphimide. The following derivatives of 1,4-diamino-anthraquinone are specifically referred to, 2-(41-methoxy-phenyl, 2 - (31 - methyl - 41 - hydroxy - phenyl), 2-(41 - methoxy - phenyl) - 3 - cyano, 2 - (41 - methoxy - phenyl) - 3 - cyano - 5,8-dichloro, 2 - (41 - methoxy - phenyl) - 3 - bromo, and 2-(41 - methoxy - phenyl) - 3 - carbodimethyl - amido. Cellulose acetates, polyamides, polyurethane and polyester materials are dyed blue-red colours with these dyes.