FIBER-REACTIVE PHTHALOCYANINESULFON-AMIDOARYLAZO - STILBENYLPYRAZOLONE DYESTUFF

1,217,546. Phthalocyanine dyestuffs. CIBA Ltd. 24 Oct., 1968 [24 Oct., 1967; 9 Sept., 1968], No. 50601/68. Heading C4P. Novel phthalocyanine dyestuffs of the formula (in which Q is the radical of a phthalocyanine, n is a number between 1 and 2 inclusive, R is an optionally substituted phenylene radical, X is a fibre-reactive group, and Y is a CH3, CO 2 alkyl or CO 2 H group) are prepared (1) by N-acylation with an acylating agent yielding the group X; or (2) by condensing a sulphochloride Q-(-S0 2 Cl) n with an appropriate amine; or (3) by coupling a diazo compound of an amine of the formula Q-(-SO 2 NH-R-NH 2 ) n with an appropriate coupling component. The starting materials for (1) and (2) are prepared similarly by coupling, the coupling components in (2) being in turn prepared by N-acylation as in (1), and the starting materials for (3) are prepared by condensing phthalocyanine sulphochlorides with diaminobenzenes H 2 NRNH 2 that may be mono-acetylated and, if necessary, subsequently splitting off the acetyl group. X may be introduced in two stages, e.g. by reaction with a 2,4,6-trihalogeno- 1 ,3,5-triazine such as cyanuric chloride and then replacement of a halogen atom in the dihalogeno triazine radical, for example by reaction with metanilic acid. Preferred dyestuffs have the formula where Pc is the radical of a metal-free phthalocyanine or of a phthalocyanine containing Co, Cu or Ni, m is 1 or 2, W 1 , W 2 and W 3 are each OH or substituted or unsubstituted NH 2 and p, q and r are each a number between zero and 3, their sum being at least 1 and the sum p+q+r+n being between 3 and 4 inclusive. Phthalocyanine sulphohalide starting materials are prepared by standard methods, and are reacted with the appropriate mono-acylated diamino benzenes, and the sulphohalide groups that do not participate in the reaction are hydrolysed, either simultaneously or subsequently, or reacted with ammonia or an aliphatic or aromatic amine, and the products are subsequently saponified, diazotized and coupled. An extensive list of fibre-reactive groups and acylating agents containing them is provided. They may be interconverted in the products, e.g. a #-chloropropionyl radical may be converted to an acryloyl radical. The novel dyestuffs are suitable for dyeing a wide variety of materials, for example silk, wool and polyamide fibres and especially polyhydroxylated materials of fibrous structure, man-made and natural; brilliant green and bluish shades are obtained.