A process for dyeing or printing a substrate comprising applying a dye to a substrate, said dye being a metal-free compound of the formula ##STR357## or a 1:1 or 1:2 metal complex thereof, or an acid addition salt of a metal-free compound of said formula or a 1:1 or 1:2 metal complex thereof, wherein B is hydrogen;
- C.sub.1-4 alkyl;
- C.sub.1-4 alkyl monosubstituted by C.sub.1-4 alkoxy;
- C.sub.2-4 alkyl substituted by hydroxy;
- C.sub.5-6 cycloalkyl;
- C.sub.5-6 cycloalkyl substituted by 1 to 3 C.sub.1-4 alkyl groups;
- phenyl(C.sub.1-3 alkyl);
- phenyl(C.sub.1-3 alkyl) the phenyl group of which is substituted by 1 to 3 substituents selected from C.sub.1-4 alkyl, C.sub.1-4 alkoxy and halo;
- --A--NH--R.sub.2 ;
- --A.sub.4 '--N(R.sub.7).sub.2 ;
- --A.sub.4 --N.sup..sym. (R.sub.8).sub.2 R.sub.9 A.sup..crclbar. or --N(R.sub.7).sub.2,
- wherein
- A is linear or branched C.sub.2-8 alkylene;
- linear or branched C.sub.2-8 alkylene interrupted by 1 or 2 hetero atoms;
- linear or branched C.sub.2-8 alkylene;
- linear or branched C.sub.2-8 alkenylene interrupted by 1 or 2 hetero atoms;
- phenylene or cyclohexylene,
- A.sub.4 is linear or branched C.sub.2-8 alkylene or linear or branched C.sub.2-8 alkenylene,
- A.sub.4 ' is linear or branched C.sub.1-8 alkylene or linear or branched C.sub.2-8 alkenylene, and
- R.sub.2 is ##STR358## wherein R.sub.11 is hydrogen, halo, nitro, C.sub.1-4 alkyl or C.sub.1-4 alkoxy, and
- R.sub.12 is --CO--(CH.sub.2).sub.a --Z or ##STR359## wherein Z is --N(R.sub.7).sub.2 or --N.sup..sym. (R.sub.8).sub.2 R.sub.9 A.sup..crclbar., and a is 1, 2 or 3,
- R is hydrogen;
- C.sub.1-4 alkyl;
- C.sub.5-6 cycloalkyl;
- C.sub.5-6 cycloalkyl substituted by 1 or 2 C.sub.1-4 alkyl groups;
- phenyl;
- phenyl substituted by 1 or 2 substituents selected from methyl, ethyl, methoxy and ethoxy;
- benzyl;
- phenylethyl;
- or benzyl or phenylethyl the phenyl group of which is substituted by 1 or 2 substituents selected from methyl, ethyl, methoxy and ethoxy,
- R.sub.1 is --N.dbd.N--D, wherein D is a diazo component radical, with the proviso that R.sub.1 must be ##STR360## when B is other than --A--NH--R.sub.2, wherein A.sub.1 is a tetrazo component radical,
- R.sub.17 is hydrogen, --N.dbd.N--K.sub.1, --N.dbd.N--A.sub.10 --N.dbd.N--K.sub.1, ##STR361## wherein A.sub.10 is a tetrazo component radical or a coupling/diazo component radical,
- K.sub.1 is a diazo component radical or a coupling component radical,
- R.sub.20 is --(NR.sub.5).sub.q --Q.sub.1 --N(R.sub.7).sub.2, --(NR.sub.5).sub.q --Q.sub.2 --N.sup..sym. (R.sub.8).sub.2 R.sub.9 A.sup..crclbar. or ##STR362## wherein Q.sub.1 is linear or branched C.sub.2-6 alkylene, --CH.sub.2 C.sup.* O-- or --CH.sub.2 CON.sup.* H--, wherein the * denotes the atom attached to the --(NR.sub.5).sub.q -- radical, and
- Q.sub.2 is linear or branched C.sub.2-6 alkylene, --CH.sub.2 C.sup.* O--, --CH.sub.2 CON.sup.* H-- or --CH.sub.2 CONHC.sup.* O--, wherein the * denotes the atom attached to the --(NR.sub.5).sub.q -- radical,
- X.sub.o is a bridging radical,
- R.sub.19 is hydrogen;
- hydroxy;
- amino;
- (C.sub.1-4 alkyl)carbonylamino;
- benzoylamino;
- phenylamino;
- or benzoylamino or phenylamino the phenyl group of which is substituted by 1 or 2 substituents selected from halo, nitro, amino, C.sub.1-4 alkyl and C.sub.1-4 alkoxy, with the proviso that R.sub.19 must be hydrogen when R.sub.17 is other than --N.dbd.N--K.sub.1 and --N.dbd.N--A.sub.10 --N.dbd.N--K.sub.1, and
- R.sub.60 is hydroxy or amino, and
- R.sub.60a is hydrogen, hydroxy or amino, with the proviso that R.sub.60a is hydrogen or amino when R.sub.60 is hydroxy and is hydroxy when R.sub.60 is amino, and
- T is hydrogen, cyano, --COOR.sub.4, --CO--N(R.sub.5).sub.2, --SO.sub.2 --N(R.sub.5).sub.2, ##STR363## wherein each R.sub.3 is independently hydrogen, C.sub.1-4 alkyl, --N(R.sub.5).sub.2 or --CO--N(R.sub.5).sub.2,
- R.sub.4 is C.sub.1-6 alkyl or phenyl(C.sub.1-3 alkyl),
- R.sub.6 is C.sub.1-4 alkyl, and
- X.sub.a is --O--, --NR.sub.5 -- or --S--,
- wherein
- each R.sub.5 is independently hydrogen or C.sub.1-4 alkyl or, when two R.sub.5 's are attached to a nitrogen atom, both R.sub.5 's taken together and with the nitrogen atom may form a saturated ring containing 1 to 3 hetero atoms,
- each R.sub.7 is independently hydrogen;
- C.sub.1-6 alkyl;
- C.sub.2-6 alkyl monosubstituted by halo, hydroxy or cyano;
- phenyl(C.sub.1-3 alkyl);
- phenyl(C.sub.1-3 alkyl) the phenyl group of which is substituted by 1 to 3 substituents selected from halo, C.sub.1-4 alkyl and C.sub.1-4 alkoxy;
- C.sub.5-6 cycloalkyl or C.sub.5-6 cycloalkyl substituted by 1 or 3 C.sub.1-4 alkyl groups, or both R.sub.7 's taken together and with the nitrogen atom to which they are attached form a 5- or 6-membered saturated ring containing 1 to 3 hetero atoms,
- each R.sub.8 is independently C.sub.1-6 alkyl;
- C.sub.2-6 alkyl monosubstituted by halo, hydroxy or cyano;
- phenyl(C.sub.1-3 alkyl);
- phenyl(C.sub.1-3 alkyl) the phenyl group of which is substituted by 1 to 3 substituents selected from halo, C.sub.1-4 alkyl and C.sub.1-4 alkoxy;
- C.sub.5-6 cycloalkyl or C.sub.5-6 cycloalkyl substituted by 1 or 3 C.sub.1-4 alkyl groups,
- each R.sub.9 is independently C.sub.1-4 alkyl or C.sub.1-4 alkyl substituted by phenyl or
- both R.sub.8 's and R.sub.9 taken together and with the nitrogen atom to which they are attached are pyridinium;
- pyridinium substituted by 1 or 2 C.sub.1-4 alkyl groups;
- or a 5- or 6-membered saturated ring containing 1 to 3 hetero atoms,
- each R.sub.13 is independently amino;
- an aliphatic, cycloaliphatic, aromatic or heterocyclic amino group the nitrogen atom of which is attached to the 1,3,5-triazine ring;
- halo;
- hydroxy;
- C.sub.1-4 alkoxy;
- phenyl or ##STR364## wherein A.sub.2 is linear or branched C.sub.2-6 alkylene or --N.sup.* HCOCH.sub.2 --, wherein the * denotes the atom attached to the --NR.sub.5 -- radical, and
- R, R.sub.1, R.sub.5 and T are as defined above,
- each R.sub.14 is independently an aliphatic, cycloaliphatic, aromatic or heterocyclic amino group the nitrogen atom of which is attached to the 1,3,5-triazine ring,
- each n is independently 0, 1 or 2,
- each q is independently 0 or 1, and
- each A.sup..crclbar. is independently a non-chromophoric anion, with the provisos that (i) when the compound of Formula I is a monoazo compound free of sulfo groups, it contains at least one water-solubilizing basic or cationic group, (ii) when the compound of Formula I is free of sulfo groups and is other than a monoazo compound, it contains at least two water-solubilizing groups, and (iii) when the compound of Formula I contains one or more sulfo groups, the total number of basic and cationic groups exceeds the number of sulfo groups by at least one.