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US 6,870,035 B2Granted
Black dye mixtures of fiber-reactive azo dyes, methods for their preparation and use thereof for dyeing hydroxy-and/or carboxamido-containing fiber material
AssigneeDyStar Textilfarben GmbH & Co. Deutschland KG
InventorsRonald Pedemonte, Joachim Steckelberg, Werner Russ
Life of this patent
Estimating the term…
Abstract
Deep black-dyeing dye mixtures comprising a disazo dye conforming to the general formula (1), and one or more disazo dyes conforming to the general formula (2), wherein the amide group is in the 6, 7, or 8 position relative to the hydroxy group and wherein: M, n, W, R1, R2, R3, R4, R5, R11, L1, L2, L3 are as defined in claim 1 methods for their preparation and use thereof for dyeing hydroxyl- and/or carboxamido-containing fiber material.
Claims9
A disazo dye of the formula (2)
- wherein
- M is hydrogen or an alkali metal;
- R5 and R6 are identical or different and are hydrogen, methyl, methoxy, sulfo, cyano or chloro;
- R11 is hydrogen or alkyl or phenyl, which is optionally mono- or di-substituted by an alkyl, alkoxy, ester, ureido, carboxamido, hydroxy, chloro, cyano of sulfo group;
- L3 is a fiber-reactive group of the formulae (5a-d):
- wherein:
- R12 has one of the meanings of R11;
- Y is in each instance, independently of one another, vinyl or is ethyl which is substituted in the β-position by a substituent which is optionally eliminated by the action of an alkali, forming the vinyl group,
- *— is the bond to the aromatic ring;
- X is chloro or fluoro;
- Z has one of the meanings of X, is hydrogen or cyano;
- Q is chloro, fluoro, cyanamido, hydroxy, alkoxy of 1 to 4 carbon atoms, pyridino, carboxypyridino, carbamoylpyridino or is a group of the formulae (6a) or (6b),
- in which
- R13 is hydrogen, alkyl of 1 to 4 carbon atoms, alkoxy of 1 to 4 carbon atoms, sulfoalkyl of 1 to 4 carbon atoms, phenyl unsubstituted or substituted by 1 to 2 substituents selected from the group of substituents consisting of chlorine, bromine, methyl, ethyl, methoxy, sulfo, acetamido, ureido and carboxy;
- R14 has one of the meanings given for R13;
- R15 has one of the meanings given for R13, or
- R13 and R14 form a cyclic ring system of the formulae (6c) or (6d)
- wherein
- Ro is a hetero group or a methylene group;
- G is arylene, C1-C6-alkylene or alkylene-arylene, each unsubstituted or substituted or being alkylene of 2 to 6 carbon atoms, if interrupted by a hetero group,
- W1 is naphthyl group of the formula (4)
- in which
- M is defined as above;
- * denotes the bond to the diazo group;
- L9 and L10 are identical or different and are hydrogen, methyl, methoxy, sulfo, cyano, or chloro;
- n is in each case independently 0 or 1;
- and
- m is 1 and
- L5 has one of the meanings of L3.
26 more elements
A disazo dye of the formula (2-1)
- wherein
- M is hydrogen or an alkali metal;
- R5 and R6 are identical or different and are hydrogen, methyl, methoxy, sulfo, cyano or chloro;
- R11 is hydrogen or alkyl or phenyl, which is optionally mono- or di-substituted by an alkyl, alkoxy, ester, ureido, carboxamido, hydroxy, chloro, cyano of sulfo group;
- L3 is a fiber-reactive group of the formulae (5a-d):
- wherein:
- R12 has one of the meanings of R11;
- Y is in each instance, independently of one another, vinyl or is ethyl which is substituted in the β-position by a substituent which is optionally eliminated by the action of an alkali, forming the vinyl group,
- *— is the bond to the aromatic ring;
- X is chloro or fluoro;
- Z has one of the meanings of X, hydrogen or cyano;
- Q is chloro, fluoro, cyanamido, hydroxy, alkoxy of 1 to 4 carbon atoms, pyridino, carboxypyridino, carbamoylpyridino or is a group of the formulae (6a) or (6b),
- in which
- R13 is hydrogen, alkyl of 1 to 4 carbon atoms, alkoxy of 1 to 4 carbon atoms, sulfoalkyl of 1 to 4 carbon atoms, phenyl unsubstituted or substituted by 1 to 2 substituents selected from the group of substituents consisting of chlorine, bromine, methyl, ethyl, methoxy, sulfo, acetamido, ureido and carboxy;
- R14 has one of the meanings given for R13;
- R15 has one of the meanings given for R13, or
- R13 and R14 form a cyclic ring system of the formulae (6c) of (6d)
- wherein
- R0 is a hetero group or a methylene group;
- G is arylene, C1-C6-alkylene or alkylene-arylene, each unsubstituted or substituted, or being alkylene of 2 to 6 carbon atoms, if interrupted by a hetero group,
- W1 is a phenyl group of the formula (3) or naphthyl group of the formula (4)
- in which
- M is defined as above;
- * denotes the bond to the diazo group;
- R7, R8, R9 and R10 are identical or different and are hydrogen, methyl, methoxy, sulfo, cyano, or chloro;
- n is in each case independently 0 or 1;
- m is 1 and
- L4 and L5 are identical or different and have one of the meanings of L3.
25 more elements
A disazo dye of the formula (2-2),
- wherein
- M is hydrogen or an alkali metal;
- R5 and R6 are identical or different and are hydrogen, methyl, methoxy, sulfo, cyano, or chloro;
- R11 is hydrogen or alkyl or phenyl, which is optionally mono- or di-substituted by an alkyl, alkoxy, ester, ureido, carboxamido, hydroxy, chloro, cyano or sulfo group;
- L3 is a fiber-reactive group of the formulae (5a-d):
- wherein
- R12 has one of the meanings of R11;
- Y is in each instance, independently of one another, vinyl or is ethyl which is substituted in the β-position by a substituent which is optionally eliminated by the action of an alkali, forming the vinyl group,
- *— is the bond to the aromatic ring;
- X is chloro or fluoro and
- Z has one of the meanings of X or is hydrogen or cyano;
- Q is chloro, fluoro, cyanamido, hydroxy, alkoxy of 1 to 4 carbon atoms, pyridino, carboxypyridino, cabamoylpyridino or is a group of the formulae (6a) or (6b),
- in which
- R13 is hydrogen, alkyl of 1 to 4 carbon atoms, alkoxy of 1 to 4 carbon atoms, sulfoalkyl of 1 to 4 carbon atoms, phenyl unsubstituted or substituted by 1 to 2 substitutents selected from the group of substituents consisting of chlorine, bromine, methyl, ethyl, methoxy, sulfo, acetamido, ureido and carboxy;
- R14 has one of the meanings given for R13;
- R15 has one of the meanings given for R13, or
- R13 and R14 form a cyclic ring system of the formula (6c) or (6d)
- wherein
- Ro is a hetero group or a methylene group;
- G is arylene, C1-C6-alkylene or alkylene-arylene, each unsubstituted or substituted, or being alkylene of 2 to 6 carbon atoms, if interrupted by a hetero group,
- Y is in each instance, independently of one another, vinyl or is ethyl which is substituted in the β-position by a substituent which is optionally eliminated by the action of an alkali, forming the vinyl group,
- W1 is a phenyl group of the formula (3) or naphthyl group of the formula (4)
- in which
- M is defined as above;
- * denotes the bond to the diazo group;
- R7, R8, R9, and R10 are identical or different and are hydrogen, methyl, methoxy, sulfo, cyano, or chloro;
- n is in each case independently 0 or 1;
- m is 1 and
- L4 and L5 are identical or different and have one of the meanings of L3.
26 more elements
A disazo dye of the formula (2)
- wherein
- M is hydrogen or an alkali metal;
- R5 and R6 are identical or different and are hydrogen, methyl, methoxy, sulfo, cyano or chloro;
- R11 is hydrogen or alkyl or phenyl, which is optionally mono- or di-substituted by an alkyl, alkoxy, ester, ureido, carboxamido, hydroxy, chloro, cyano of sulfo group;
- L3 is a fiber-reactive group of the formulae (5a-d):
- wherein:
- R12 has one of the meanings of R11;
- *— is the bond to the aromatic ring;
- X is chloro or fluoro;
- Z has one of the meanings of X, hydrogen or cyano;
- Q is chloro, fluoro, cyanamido, hydroxy, alkoxy of 1 to 4 carbon atoms, pyridino, carboxypyridino, carbamoylpyridino or is a group of the formulae (6a) or (6b),
- in which
- R13 is hydrogen, alkyl of 1 to 4 carbon atoms, alkoxy of 1 to 4 carbon atoms, sulfoalkyl of 1 to 4 carbon atoms, phenyl unsubstituted or substituted by 1 to 2 substituents selected from the group of substituents consisting of chlorine, bromine, methyl, ethyl, methoxy, sulfo, acetamido, ureido and carboxy;
- R14 has one of the meanings given for R13;
- R15 has one of the meanings given for R13, or
- R13 and R14 form a cyclic ring system of the formulae (6c) of (6d)
- wherein
- Ro is a hetero group or a methylene group;
- G is arylene, C1-C6-alkylene or alkylene-arylene, each unsubstituted or substituted, or being alkylene of 2 to 6 carbon atoms, if interrupted by a hetero group,
- Y is in each instance, independently of one another, vinyl or is ethyl which is substituted in the βposition by a substituent which is optionally eliminated by the action of an alkali, forming the vinyl group,
- W1 is a phenyl group of the formula (3) or naphthyl group of the formula (4)
- in which
- M is defined as above;
- * denotes the bond to the diazo group;
- R7, R8, R9 and R10 are identical or different and are hydrogen, methyl, methoxy, sulfo, cyano, or chloro;
- n is in each case independently 0 or 1;
- m is 1 and
- L4 and L5 are identical or different and have one of the meanings of L3.
25 more elements
A disazo dye of the formula (I)
Dependencies are inferred from the claim text.