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US 6,063,137 AGranted
Process for dyeing or printing and novel reactive dyes
AssigneeCiba Specialty Chemicals Corporation
InventorsPeter Scheibli, Peter Aeschlimann, Urs Lehmann, Marcel Frick
Life of this patent
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Abstract
Process for dyeing or printing paper, films of plastic or fibre material containing hydroxyl groups or containing nitrogen with reactive dyes, which comprises using at least one reactive dye of the formula (1) from the following group a) and at least one reactive dye from the following groups b), c) and d): a) green- or blue-dyeing reactive dyes of the formula (1) ##STR1## b) blue-dyeing reactive dyes of the formula (2) or (3) ##STR2## c) red-dyeing reactive dyes of the formula (4) ##STR3## d) yellow- or orange-dyeing reactive dyes of the formula (5) ##STR4##
Claims23
A process for dyeing or printing paper, films of plastic or fibre material containing hydroxyl groups or containing nitrogen with reactive dyes, which comprises dyeing with a dye mixture of at least one reactive dye of the formula (1) from the following group a) and at least one reactive dye from the following groups b), c) and d):
- wherein
- a) is a green- or blue-dyeing reactive dye of the formula (1) ##STR77## in which NiPhC is the radical of a nickel phthalocyanine,
- R.sub.1 is hydrogen or substituted or unsubstituted C.sub.1 -C.sub.4 alkyl,
- V.sub.1 is C.sub.1 -C.sub.8 alkyl which is substituted by a fibre-reactive group of the formula ##STR78## in which R' is hydrogen or C.sub.1 -C.sub.4 alkyl,
- X.sub.5 is fluorine or chlorine,
- Y.sub.4 is hydrogen, C.sub.1 -C.sub.8 alkyl which is unsubstituted or substituted by hydroxyl, sulfo or sulfato and uninterrupted or interrupted by oxygen, or phenyl or naphthyl which are unsubstituted or substituted by C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, halogen, carboxyl or sulfo, and
- Z is a radical of the formula --CH.dbd.CH.sub.2 or --CH.sub.2 --CH.sub.2 --U.sub.1 and U.sub.1 is a leaving group;
- or V.sub.1 is phenyl or naphthyl which are substituted by a fibre-reactive group of the formula (8a), (8b) or (8c) in which R', X.sub.5, Y.sub.4 and
- Z are defined as above and furthermore may be substituted by C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, halogen, carboxyl or sulfo;
- and
- x is 2 to 4 and y is 1 to 2;
- b) is a blue-dyeing reactive dye of the formula (2) or (3) ##STR79## in which (R.sub.2).sub.0-3 is 0 to 3 C.sub.1 -C.sub.4 alkyl radicals which are identical or different from one another and
- (R.sub.3).sub.0-3 is 0 to 3 substituents, which are identical or different from another, selected from the group consisting of C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, halogen, carboxyl and sulfo,
- X.sub.1 is chlorine or fluorine and
- R.sub.4 is hydrogen or C.sub.1 -C.sub.4 alkyl which is unsubstituted or substituted by hydroxyl, sulfo or sulfato, ##STR80## in which R.sub.5 is hydrogen or C.sub.1 -C.sub.4 alkyl which is unsubstituted or substituted by hydroxyl, sulfo or sulfato,
- X.sub.2 is chlorine,
- Y.sub.1 is hydrogen, C.sub.1 -C.sub.8 alkyl which is unsubstituted or substituted by hydroxyl, sulfo or sulfato and uninterrupted or interrupted by oxygen, or phenyl or naphthyl which are unsubstituted or substituted by C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, halogen, carboxyl or sulfo, and
- the benzene nuclei I, II, and III contain no further substituents or are further substituted by C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, halogen or carboxyl;
- with the proviso that the reactive dye of formula (3) is not the reactive dye of the formula
- c) is a red-dyeing reactive dye of the formula (4) ##STR81## in which R.sub.6 is hydrogen or C.sub.1 -C.sub.4 alkyl which is unsubstituted or substituted by hydroxyl, sulfo or sulfato,
- R.sub.7 and R.sub.8 independently of one another are hydrogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, halogen, carboxyl or sulfo,
- X.sub.3 is chlorine or fluorine and
- Y.sub.2 is hydrogen, C.sub.1 -C.sub.8 alkyl which is unsubstituted or substituted by hydroxyl, sulfo, sulfato or a radical of the formula --SO.sub.2 --Z and is uninterrupted or interrupted by oxygen, or phenyl or naphthyl which are unsubstituted or substituted by C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, halogen, carboxyl, sulfo or a radical of the formula --SO.sub.2 --Z or --CO--NH--(CH.sub.2).sub.2-3 --SO.sub.2 --Z, or
- the radical --N(R.sub.6)--Y.sub.2 is morpholino, in which
- Z is a radical of the formula --CH.dbd.CH.sub.2 or --CH.sub.2 --CH.sub.2 --U.sub.1 and U.sub.1 is a leaving group;
- d) is a yellow- or orange-dyeing reactive dye of the formula (5) ##STR82## in which R.sub.9 is hydrogen or C.sub.1 -C.sub.4 alkyl which is unsubstituted or substituted by hydroxyl, sulfo or sulfato,
- R.sub.10 and R.sub.11 independently of one another are hydrogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, halogen, carboxyl or sulfo,
- X.sub.4 is chlorine or fluorine and
- Y.sub.3 is hydrogen, C.sub.1 -C.sub.8 alkyl which is unsubstituted or substituted by hydroxyl, sulfo or sulfato and is uninterrupted or interrupted by oxygen, or phenyl or naphthyl which are unsubstituted or substituted by C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, halogen, carboxyl, sulfo or a halogenotriazinylamino radical which is unsubstituted or further substituted, or
- the radical --N(R.sub.9)--Y.sub.3 is morpholino, and
- K.sub.1 is a radical of the formula ##STR83## in which R.sub.12 is hydroxyl or amino,
- R.sub.13 is methyl or carboxyl,
- (R.sub.14).sub.0-3 is 0 to 3 identical or different substituents from the group consisting of C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, halogen, carboxyl and sulfo,
- R.sub.15 and R.sub.17 are C.sub.1 -C.sub.4 alkyl and
- R.sub.16 is cyano, carbamoyl or sulfomethyl.
32 more elements
A process for printing paper, films of plastic or fibre material containing hydroxyl groups or containing nitrogen with reactive dyes by the ink jet printing process, which comprises printing with at least one reactive dye of the formula (1) from the following group a) and at least one reactive dye from the following groups b), c) and d) wherein a) is a green- or blue-dyeing reactive dye of the formula (1) ##STR89## in which NiPhC is the radical of a nickel phthalocyanine,
- R.sub.1 is hydrogen or substituted or unsubstituted C.sub.1 -C.sub.4 alkyl,
- V.sub.1 is C.sub.1 -C.sub.8 alkyl, phenyl or naphthyl which is substituted by at least one fibre-reactive group and may be further substituted,
- x is 2 to 4 and y is 1 to 2;
- b) is a blue-dyeing reactive dye of the formula (2) or (3) ##STR90## in which (R.sub.2).sub.0-3 is 0 to 3 C.sub.1 -C.sub.4 alkyl radicals which are identical or different from one another and
- (R.sub.3).sub.0-3 is 0 to 3 substituents, which are identical or different from another, from the group consisting of C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, halogen, carboxyl and sulfo,
- X.sub.1 is chlorine or fluorine and
- R.sub.4 is hydrogen or C.sub.1 -C.sub.4 alkyl which is unsubstituted or substituted by hydroxyl, sulfo or sulfato, ##STR91## in which R.sub.5 is hydrogen or C.sub.1 -C.sub.4 alkyl which is unsubstituted or substituted by hydroxyl, sulfo or sulfato,
- X.sub.2 is chlorine or fluorine,
- Y.sub.1 is hydrogen, C.sub.1 -C.sub.8 alkyl which is unsubstituted or substituted by hydroxyl, sulfo or sulfato and uninterrupted or interrupted by oxygen, or phenyl or naphthyl which are unsubstituted or substituted by C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, halogen, carboxyl or sulfo, and the benzene nuclei I, II and III contain no further substituents or are further substituted by C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, halogen or carboxyl;
- c) is a red-dyeing reactive dye of the formula (4) ##STR92## in which R.sub.6 is hydrogen or C.sub.1 -C.sub.4 alkyl which is unsubstituted or substituted by hydroxyl, sulfo or sulfato,
- R.sub.7 and R.sub.8 independently of one another are hydrogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, halogen, carboxyl or sulfo,
- X.sub.3 is chlorine or fluorine and
- Y.sub.2 is hydrogen, C.sub.1 -C.sub.8 alkyl which is unsubstituted or substituted by hydroxyl, sulfo, sulfato or a radical of the formula --SO.sub.2 --Z and is uninterrupted or interrupted by oxygen, or phenyl or naphthyl which are unsubstituted or substituted by C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, halogen, carboxyl, sulfo or a radical of the formula --SO.sub.2 --Z or --CO--NH--(CH.sub.2).sub.2-3 --SO.sub.2 --Z, or the radical --N(R.sub.6)--Y.sub.2 is morpholino, in which
- Z is a radical of the formula --CH.dbd.CH.sub.2 or --CH.sub.2 --CH.sub.2 --U.sub.1 and U.sub.1 is a leaving group;
- d) is a yellow- or orange-dyeing reactive dye of the formula (5) ##STR93## in which R.sub.9 is hydrogen or C.sub.1 -C.sub.4 alkyl which is unsubstituted or substituted by hydroxyl, sulfo or sulfato,
- R.sub.10 and R.sub.11 independently of one another are hydrogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, halogen, carboxyl or sulfo,
- X.sub.4 is chlorine or fluorine and
- Y.sub.3 is hydrogen, C.sub.1 -C.sub.8 alkyl which is unsubstituted or substituted by hydroxyl, sulfo or sulfato and is uninterrupted or interrupted by oxygen, or phenyl or naphthyl which are unsubstituted or substituted by C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, halogen, carboxyl, sulfo or a halogenotriazinylamino radical which is unsubstituted or further substituted, or the radical --N(R.sub.9)--Y.sub.3 is morpholino, and
- K.sub.1 is a radical of the formula ##STR94## in which R.sub.12 is hydroxyl or amino,
- R.sub.13 is methyl or carboxyl,
- (R.sub.14).sub.0-3 is 0 to 3 identical or different substituents selected from the group consisting of C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, halogen, carboxyl and sulfo,
- R.sub.15 and R.sub.17 are C.sub.1 -C.sub.4 alkyl and
- R.sub.16 is cyano, carbamoyl or sulfomethyl.
20 more elements
Dependencies are inferred from the claim text.