US 5,583,207 AGranted

Fibre-reactive monoazo copper complexes containing a halo substituted pyrimidine substituent

AssigneeSandoz Ltd.

InventorsRainer Nusser, Roland Wald

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Abstract

Fibre-reactive 1:1 copper complexes of the formula ##STR1## which compounds are in free acid or salt form, and mixtures thereof, are useful for dyeing or printing hydroxy group- or nitrogen-containing organic substrates, for example leather and fibre material comprising natural or synthetic polyamides or natural or regenerated cellulose; the most preferred substrate is a textile material comprising cotton.

Claims19

Dependent claims

A 1:1 copper complex of formula I ##STR85## or a salt thereof, or a mixture of such complexes or salts, in which R.sub.1 is hydrogen, halogen, C.sub.1-4 alkyl, C.sub.1-4 alkoxy, carboxy or sulpho;

R.sub.3 is hydrogen, or sulpho;
R.sub.D is hydrogen, sulpho or --NR.sub.2 --Z.sub.x ;
and
R.sub.K is hydrogen, sulpho or ##STR86## in which each R.sub.2 is independently hydrogen, C.sub.1-4 alkyl or C.sub.2-4 hydroxyalkyl,
t is 0 or 1, and
each Z.sub.x is independently A.sub.a or ##STR87## wherein Z.sub.a is ##STR88## in which T.sub.1 is hydrogen, chloro or cyano, and the two T.sub.2 's are the same and each is fluoro or chloro,
Hal is fluoro or chloro;
and
W.sub.1 is ##STR89## wherein m is 0 or 1 and the marked nitrogen atom is bound to a carbon atom of the triazine ring,
B.sub.1 is C.sub.2-6 alkylene, --C.sub.2-3 alkylene-Q--C.sub.2-3 alkylene- in which Q is --O-- or --NR.sub.2 --, C.sub.3-4 alkylene monosubstituted by hydroxy, ##STR90## in which n is 0 or an integer 1 to 4, R.sub.4 is hydrogen, C.sub.1-4 alkyl, C.sub.1-4 alkoxy, carboxy or sulpho,
and the marked carbon atom is attached to the --NR.sub.2 group which is bound to a carbon atom of the triazine ring,
with the proviso that at least one of R.sub.D and R.sub.K is a Z.sub.X -containing radical in which Z.sub.a is ##STR91## or R.sub.D and R.sub.K, when R.sub.1 is hydrogen or sulpho, are --NR.sub.2 --Z.sub.y, where both groups Z.sub.y are the same and each Z.sub.y is Z.sub.b or ##STR92## in which Y is --NR.sub.5 R.sub.6, --W.sub.1 --Z.sub.y, or --NR.sub.2 --W.sub.2 --SO.sub.2 --X
wherein
R.sub.5 is hydrogen, C.sub.1-4 alkyl or C.sub.2-4 alkyl monosubstituted by hydroxy, cyano or sulpho;
R.sub.6 is hydrogen, C.sub.1-4 alkyl, C.sub.2-4 alkyl monosubstituted by hydroxy, cyano or sulpho;
phenyl, phenyl substituted by one or two substituents selected from chloro,
C.sub.1-4 alkyl, C.sub.1-4 alkoxy and sulpho, phenyl(C.sub.1-4 alkyl) or phenyl(C.sub.1-4 alkyl) the phenyl ring of which is substituted by one or two substituents selected from chloro, C.sub.1-4 alkyl, C.sub.1-4 alkoxy and sulpho, or
--NR.sub.5 R.sub.6 is piperidino or morpholino;
W.sub.1 and R.sub.2 are as defined above;
W.sub.2 is a linear or branched C.sub.2-8 alkylene which may be interrupted by --O-- or --NR.sub.2 --, and which may be further substituted by hydroxy or --OSO.sub.3 H aliphatic;
or a 1,3- or 1,4-phenylene which is unsubstituted or substituted or monosubstituted by sulpho or carboxy;
X is --CH.dbd.CH.sub.2 or --CH.sub.2 CH.sub.2 --T.sub.x in which T.sub.x is hydroxy, or a radical which is split off under alkaline conditions;
and
Z.sub.b is a pyrimidinyl radical of the formulae, ##STR93##

21 more elements

Dependencies are inferred from the claim text.

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Abstract

A 1:1 copper complex of formula I ##STR85## or a salt thereof, or a mixture of such complexes or salts, in which R.sub.1 is hydrogen, halogen, C.sub.1-4 alkyl, C.sub.1-4 alkoxy, carboxy or sulpho;

R.sub.3 is hydrogen, or sulpho;
R.sub.D is hydrogen, sulpho or --NR.sub.2 --Z.sub.x ;
and
R.sub.K is hydrogen, sulpho or ##STR86## in which each R.sub.2 is independently hydrogen, C.sub.1-4 alkyl or C.sub.2-4 hydroxyalkyl,
t is 0 or 1, and
each Z.sub.x is independently A.sub.a or ##STR87## wherein Z.sub.a is ##STR88## in which T.sub.1 is hydrogen, chloro or cyano, and the two T.sub.2 's are the same and each is fluoro or chloro,
Hal is fluoro or chloro;
and
W.sub.1 is ##STR89## wherein m is 0 or 1 and the marked nitrogen atom is bound to a carbon atom of the triazine ring,
B.sub.1 is C.sub.2-6 alkylene, --C.sub.2-3 alkylene-Q--C.sub.2-3 alkylene- in which Q is --O-- or --NR.sub.2 --, C.sub.3-4 alkylene monosubstituted by hydroxy, ##STR90## in which n is 0 or an integer 1 to 4, R.sub.4 is hydrogen, C.sub.1-4 alkyl, C.sub.1-4 alkoxy, carboxy or sulpho,
and the marked carbon atom is attached to the --NR.sub.2 group which is bound to a carbon atom of the triazine ring,
with the proviso that at least one of R.sub.D and R.sub.K is a Z.sub.X -containing radical in which Z.sub.a is ##STR91## or R.sub.D and R.sub.K, when R.sub.1 is hydrogen or sulpho, are --NR.sub.2 --Z.sub.y, where both groups Z.sub.y are the same and each Z.sub.y is Z.sub.b or ##STR92## in which Y is --NR.sub.5 R.sub.6, --W.sub.1 --Z.sub.y, or --NR.sub.2 --W.sub.2 --SO.sub.2 --X
wherein
R.sub.5 is hydrogen, C.sub.1-4 alkyl or C.sub.2-4 alkyl monosubstituted by hydroxy, cyano or sulpho;
R.sub.6 is hydrogen, C.sub.1-4 alkyl, C.sub.2-4 alkyl monosubstituted by hydroxy, cyano or sulpho;
phenyl, phenyl substituted by one or two substituents selected from chloro,
C.sub.1-4 alkyl, C.sub.1-4 alkoxy and sulpho, phenyl(C.sub.1-4 alkyl) or phenyl(C.sub.1-4 alkyl) the phenyl ring of which is substituted by one or two substituents selected from chloro, C.sub.1-4 alkyl, C.sub.1-4 alkoxy and sulpho, or
--NR.sub.5 R.sub.6 is piperidino or morpholino;
W.sub.1 and R.sub.2 are as defined above;
W.sub.2 is a linear or branched C.sub.2-8 alkylene which may be interrupted by --O-- or --NR.sub.2 --, and which may be further substituted by hydroxy or --OSO.sub.3 H aliphatic;
or a 1,3- or 1,4-phenylene which is unsubstituted or substituted or monosubstituted by sulpho or carboxy;
X is --CH.dbd.CH.sub.2 or --CH.sub.2 CH.sub.2 --T.sub.x in which T.sub.x is hydroxy, or a radical which is split off under alkaline conditions;
and
Z.sub.b is a pyrimidinyl radical of the formulae, ##STR93##

21 more elements