US 5,023,326 AGranted

Reactive dyes containing the 2-(cyano, carbonamido, sulfo-, hydroxy- or sulfato-C.sub.2 -C.sub.5 -alkyleneamino)-6-sulfo- or 3,6-disulfo-8-hydroxynaphthyl-(1) coupling component

AssigneeCiba-Geigy Corporation

InventorsAthanassios Tzikas, Herbert Seiler

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Abstract

Reactive dyes of the formula ##STR1## in which Y is hydrogen or sulfo, U is --CN, --CONH.sub.2, --SO.sub.3 H, --OH or --OSO.sub.3 H, D is a phenyl or naphthyl radical, which can be substituted by C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, halogen, carboxyl and sulfo, and which contains at least one reactive radical bound direclty or via a bridge member to a ring carbon atom, or to which a further radical is bound which contains a reactive radical, and u is the number 2, 3, 4 or 5, are suitable in particular for the dyeing or printing of cellulose-containing fiber materials by the exhaust method or by the continuous method and product in combination with a high colorisitc yield dyeings and prints which have good fastness properties.

Claims23

Dependent claims

A reactive dye of the formula ##STR159## in which Y is hydrogen or sulfo, U is --CN, --CONH.sub.2, --SO.sub.3 H, --OH or --OSO.sub.3 H, u is the number 2, 3, 4 or 5 and D is a radical of the formula ##STR160## in which Q is C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, halogen, carboxyl or sulfo, v is the number 0, 1 or 2 and w is the number 1 or 2 and u' is the number 2, 3, 4 or 5, and Z is .beta.-sulfatoethyl, .beta.-thiosulfatoethyl, .beta.-phosphatoethyl, .beta.-acyloxyethyl, .beta.-halogenoethyl or vinyl;

or D is a radical of the formula ##STR161## Q' is C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, halogen, carboxyl, sulfo or --SO.sub.2 --Z in which Z is as defined above, v is the number 0, 1 or 2, B is a direct bond or a radical --(CH.sub.2)--.sub.n or --O--(CH.sub.2)--.sub.n ;
n is 1, 2, 3, 4, 5 or 6;
R is a radical of the formula ##STR162## in which R' is hydrogen or C.sub.1 -C.sub.6 alkyl, alk is an alkylene radical having 1 to 7 carbon atoms or branched isomers thereof, T is hydrogen, halogen, hydroxyl, sulfato, carboxyl, cyano, C.sub.1 -C.sub.4 alkanoyloxy, C.sub.1 -C.sub.4 alkoxycarbonyl, carbamoyl or a radical --SO.sub.2 --Z, V is hydrogen or C.sub.1 -C.sub.4 alkyl or a radical of the formula ##STR163## in which (alk) is as defined above, alk', independently of one another, are polymethylene radicals having 2 to 6 C atoms or branched isomers thereof, Z is as defined above, p, q, r and t, independently of one another, are each the number 1, 2, 3, 4, 5 or 6 and s is 2, 3, 4, 5 or 6.

A reactive dye of the formula ##STR164## in which Y is hydrogen or sulfo, U is --CN, --CONH.sub.2, --SO.sub.3 H, --OH or --OSO.sub.3 H, u is the number 2, 3, 4 or 5, and D is a radical of the formula ##STR165## and X is a radical of the formula

--NHCOCBr.dbd.CH.sub.2 ( 5a),
--NHCOCHBrCH.sub.2 Br (5b),
--NHCO--(CH.sub.2).sub.3 SO.sub.2 --Z (5c) or
--N(R.sub.11)--SO.sub.2 --Z (5d),
Q is C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, halogen, carboxyl or sulfo, v is the number 0, 1 or 2, R.sub.11 is hydrogen, methyl or ethyl, x is the number 0 or 1, and Z is .beta.-sulfatoethyl, .beta.-thiosulfatoethyl, .beta.-phosphatoethyl, .beta.-acyloxyethyl, .beta.-halogenoethyl or vinyl;
or D is a radical of the formula ##STR166## in which Q, v and x are defined as given for formulae (4a), (4b) and (4c), R.sub.2 is hydrogen, methyl, or ethyl, and X' is 2,4,5-trichloro-6-pyrimidinyl or 2,4-difluoro-5-chloro-6-pyrimidinyl, or X' is a radical of the formula ##STR167## X.sub.1 is fluorine or chlorine and X.sub.2 is a radical of the formula ##STR168## in which R.sub.2, v and Q are defined as given for formulae (9a), (9b) and (9c) and X.sub.3 is a radical of the formula
--NHCOCBr.dbd.CH.sub.2 ( 5a),
--NHCOCHBr--CH.sub.2 Br (5b),
--NHCO--(CH.sub.2).sub.3 SO.sub.2 --Z (5c) or
--N(R.sub.11)--SO.sub.2 --Z (5d),
R.sub.11 is hydrogen, methyl or ethyl, and Z .beta.-sulfatoethyl, .beta.-thiosulfatoethyl, .beta.-phosphatoethyl, .beta.-acyloxyethyl, .beta.-halogenoethyl or vinyl, or X' is a radical of the formula ##STR169## in which X.sub.4 is fluorine, chlorine, bromine, sulfo, C.sub.1 -C.sub.4 alkylsulfonyl, phenylsulfonyl, carboxypyridinium, --NH.sub.2 or C.sub.1 -C.sub.4 alkylamino, N,N-di-C.sub.1 -C.sub.4 alkylamino, phenylamino, N-C.sub.1 -C.sub.4 alkyl-N-phenylamino or naphthylamino, in which the alkyl radicals are unsubstituted or substituted by C.sub.1 -C.sub.4 alkoxy, cyano, halogen, hydroxyl, sulfo or sulfato, and the phenyl or naphthyl radical can be substituted by C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, halogen, carboxyl or sulfo;
or is morpholino, or has the same meaning as X.sub.5, independently thereof, and X.sub.5 is a radical of the formula ##STR170## in which Q, v, R.sub.2, u and Z are defined as given above, or X' is a radical of the formula ##STR171## in which X.sub.6 is fluorine, chlorine, bromine, sulfo, C.sub.1 -C.sub.4 alkylsulfonyl, phenylsulfonyl, carboxypyridinium, --NH.sub.2 or C.sub.1 -C.sub.4 alkylamino, N,N-di-C.sub.1 -C.sub.4 alkylamino, phenylamino, N-C.sub.1 -C.sub.4 alkyl-N-phenylamino or naphthylamino, in which the alkyl radicals are unsubstituted or substituted by C.sub.1 -C.sub.4 alkoxy, cyano, halogen, hydroxyl, sulfo or sulfato, and the phenyl or naphthyl radical can be substituted by C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, halogen, carboxyl or sulfo;
or is morpholino, or has the same meaning as X.sub.7 independently thereof, and X.sub.7 is a radical of the formula ##STR172## in which Q' is C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, halogen, carboxyl, sulfo, --SO.sub.2 --Z or sulfato, v is the number 0, 1 or 2, R.sub.3 is hydrogen or C.sub.1 -C.sub.4 alkyl which is unsubstituted or substituted by halogen, hydroxyl, cyano, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 alkoxycarbonyl, carboxyl, sulfamoyl, sulfo or sulfato, B is a direct bond or a radical --(CH.sub.2)--.sub.n or --O--(CH.sub.2)--.sub.n ;
n is 1, 2, 3, 4, 5 or 6;
R is a radical of the formula ##STR173## in which R' is hydrogen or C.sub.1 -C.sub.6 alkyl, alk is an alkylene radical having 1 to 7 carbon atoms or branched isomers thereof, T is hydrogen, halogen, hydroxyl, sulfato, carboxyl or cyano, C.sub.1 -C.sub.4 alkanoyloxy, C.sub.1 -C.sub.4 alkoxycarbonyl, carbamoyl or a radical --SO.sub.2 --Z, V is hydrogen or C.sub.1 -C.sub.4 alkyl or a radical of the formula ##STR174## in which (alk) is as defined above, alk', independently of one another, are polymethylene radicals having 2 to 6 C atoms or branched isomers thereof, Z is as defined above, p, q, r and t, independently of one another, are each the number 1, 2, 3, 4, 5 or 6 and s is 2, 3, 4, 5 or 6, or X.sub.7 is a radical of the formula (7a), (7b), (7c), (7d), (7e) or (7f) which is bound directly to the triazine ring and in which Z, alk, T, V, R', alk', p, q, r, s and t are as defined above.

12 more elements

Dependencies are inferred from the claim text.