Phthalocyanine azo dyes containing 5-cyano-dichloropyrimidyl group

A compound of the formula ##STR44## or a salt thereof, or a mixture of such compounds or salts,

• wherein
• Me is Cu, Ni, Co, Fe or Al,
• Pc is the phthalocyanine ring,
• each R.sub.2 and R.sub.3 is independently hydrogen or C.sub.1-6 alkyl, or
• --NR.sub.2 R.sub.3 is a pyrrolidine, piperidine, piperazine or morpholine ring,
• R.sub.4 is hydrogen, halo, hydroxy, C.sub.1-4 alkyl, C.sub.1-4 alkoxy, --COOH or --SO.sub.3 H,
• Y is ##STR45## wherein Q.sub.3a is ##STR46## Q.sub.4 is linear or branched C.sub.2-6 alkylene;
• linear or branched C.sub.3-6 alkylene monosubstituted by hydroxy;
• linear or branched C.sub.2-6 alkylene interrupted by one radical selected from --O-- and --NR.sub.1 --;
• ##STR47## wherein W.sub.a is linear or branched C.sub.1-4 alkylene,
• m is 0 or 1, and
• the * denotes the carbon atom attached to the nitrogen atom of the pyridone ring, or
• --Q.sub.4 --NR.sub.1 -- is ##STR48## wherein W.sub.b is linear or branched C.sub.2-4 -alkylene, and
• the * denotes the carbon atom attached to the nitrogen atom of the pyridone ring,
• R.sub.5 is hydroxy or amino,
• R.sub.6 is C.sub.1-4 alkyl or --COR.sub.8,
• R.sub.9 is hydrogen;
• C.sub.1-4 alkyl;
• C.sub.5-6 cycloalkyl;
• phenyl;
• phenyl substituted by 1 to 3 substituents selected from C.sub.1-4 alkyl, C.sub.1-4 -alkoxy, halo, --COOH and --SO.sub.3 H;
• phenyl-(C.sub.1-4 alkyl);
• phenyl(C.sub.1-4 alkyl) the phenyl ring of which is substituted by 1 to 3 substituents selected from C.sub.1-4 alkyl, C.sub.1-4 alkoxy, halo, --COOH and --SO.sub.3 H;
• --COR.sub.8 ;
• --(CH.sub.2).sub.n --SO.sub.3 H;
• --(CH.sub.2).sub.n --OSO.sub.3 H or --(CH.sub.2).sub.n --COR.sub.8,
• wherein n is 1, 2, 3 or 4,
• R.sub.10 is hydrogen;
• cyano;
• --SO.sub.3 H;
• --COR.sub.8 ;
• C.sub.1-4 alkyl;
• C.sub.1-4 alkyl monosubstituted by hydroxy, halo, cyano, C.sub.1-4 alkoxy, --SO.sub.3 H, --OSO.sub.3 H, amino or ##STR49## wherein R.sub.11 is hydrogen, C.sub.1-4 alkyl or C.sub.2-4 hydroxyalkyl, and
• An.crclbar. is a non-chromophoric anion, and
• the ** denotes the carbon atoms to which the --N.dbd.N-- radical is attached,
• a is 1, 2 or 3, and
• b is 0, 1 or 2, with the proviso that the sum of a and b is a maximum of 3,
• wherein
• each R.sub.1 is independently hydrogen, C.sub.1-4 alkyl or C.sub.1-4 alkyl monosubstituted by hydroxy, halo, --SO.sub.3 H, --OSO.sub.3 H or --COOH,
• each R.sub.7 is independently hydrogen, halo, C.sub.1-4 alkyl, C.sub.1-4 alkoxy, --COOH or --SO.sub.3 H,
• each R.sub.8 is independently hydroxy, C.sub.1-4 alkoxy or amino, and
• each halo is independently fluoro, chloro or bromo.