GB1116014A - Azophthalocyanine reactive dyestuffs - Google Patents

Abstract

The invention comprises azophthalocyanine reactive dyestuffs of the general formula <FORM:1116014/C4-C5/1> wherein Pc is a radical of a metal phthalocyanine, R is H or C1-C5 alkyl, K is a radical of an enolic coupling component, R1 is a mono or bicyclic aromatic radical, R2 is H, A is a radical containing a 5- or 6-membered heterocyclic ring having attached to a carbon atom of the hetero ring at least one sulphonyl substituent capable of being split off, n is 0 to 3, m is 1 to 4 and m + n is not greater than 4. The radical Pc may be substituted by halogen, methyl, methoxy, phenyl optionally substituted sulphonamide groups, and bis-sulphonyl-imide groups and K, A and R1 may be substituted by sulphonic, carbonylic, halogen, alkyl, alkoxy, nitro, cyano, carbonylic acid ester or amide, amino or substituted amino, hydroxyl, aryl, aralkyl or cycloalkyl groups. Preferred dyes have the general formula <FORM:1116014/C4-C5/2> wherein Pc1 is a copper or nickel phthalocyanine radical, Pz is a 1-aryl-3-methyl-5-pyrazolone radical bound to SO2NH- via the 1-aryl group and linked to -N = N- in the 4-position, P is 1 or 2, R3 and R5 are splittable sulphonyl groups and R5 may be H or C1-C5 alkyl, R4 is H or chlorine and n1 is 2 or 3. The dyes are prepared by (a) coupling a phthalocyanine of the formula <FORM:1116014/C4-C5/3> with a diazo compound of an amine H2N-R1N(R2)-A the coupling component having been optionally prepared from an appropriate phthalocyanine sulphonic acid halide and an amino group containing enolic coupling component, (b) condensing a phthalocyanine azo dye of general formula <FORM:1116014/C4-C5/4> with a compound AY, wherein Y is radical which is split off as an anion in aqueous, aqueous-organic or organic medium or (c) a metal phthalocyanine sulphonic acid halide of the general formula <FORM:1116014/C4-C5/5> is condensed with an amino azo compound HN(R)-K-N = N-R1-N(R2)A any residual sulphonic acid halide groups being either hydrolysed to sulphonic acid groups or reacted with ammonia or amines to sulphonamide groups. Preferably, reaction conditions provide for 1 free sulphonic acid group in the product dyes. The dyes give yellow and green shades on hydroxyl group containing materials, e.g. natural and regenerated cellulose.