Method of printing cellulosic fiber materials without an additional fixing process step
View Patent ↗Reactive dyes of formula wherein A is the radical of a monoazo, polyazo, metal complex azo, anthraquinone, phthalocyanine, formazan or dioxazine chromophore, R 1 , R 2 and R 3 are each hydrogen or unsubstituted or substituted C 1 -C 4 alkyl, X 1 and X 2 are halogen, B is an organic bridging member, T is a reactive radical as defined herein and V 1 and V 2 are each independently of the other N, C—H, C—Cl or C—F, give prints that are distinguished by brilliant color shades and good all-round properties.
1. A reactive dye of formula
wherein
A is the radical of a monoazo, polyazo, metal complex azo, anthraquinone, phthalocyanine or dioxazine chromophore,
R 1 is hydrogen or unsubstituted or substituted C 1 -C 4 alkyl,
R 2 and R 3 are hydrogen,
X 1 and X 2 are halogen,
B is a radical of formula —CH 2 —CH(R 7 )— or —(R 7 )CH—CH 2 —, wherein R 7 is C 1 -C 4 alkyl,
T is a reactive radical of formula
R 4 is hydrogen, C 1 -C 4 alkyl unsubstituted or substituted by hydroxy, sulfo, sulfato, carboxy or by cyano, or a radical
wherein R 5 is as defined hereinbelow,
R 5 is hydrogen, hydroxy, sulfo, sulfato, carboxy, cyano, halogen, C 1 -C 4 alkoxycarbonyl, C 1 -C 4 alkanoyloxy, carbamoyl or a group —SO 2 —Y,
R 6 is hydrogen or C 1 -C 4 alkyl,
alk and alk 1 are each independently of the other linear or branched C 1 -C 6 alkylene,
arylene is an unsubstituted or sulfo-, carboxy-, hydroxy-, C 1 -C 4 alkyl-, C 1 -C 4 alkoxy- or halo-substituted phenylene or naphthylene radical,
Y is vinyl or a radical —CH 2 —CH 2 —U and U is a leaving group,
Y 1 is a group —CH(Hal)—CH 2 (Hal) or —C(Hal)═CH 2 , wherein Hal is chlorine or bromine,
W is a group —SO 2 —NR 6 —, —CONR 6 — or —NR 6 CO—, wherein R 6 is as defined hereinabove,
Q is a radical —O— or —NR 6 —, wherein R 6 is as defined hereinabove,
n is the number 0 or 1, and
V 1 and V 2 are each independently of the other N, C—H, C—Cl or C—F.
2. A print paste, comprising a reactive dye of formula (1) according to claim 1 .
3. A reactive dye according to claim 1 , wherein R 1 is hydrogen or C 1 -C 4 alkyl.
4. A reactive dye according to claim 1 , wherein X 1 and X 2 are each independently of the other chlorine or fluorine.
5. A reactive dye according to claim 1 , wherein one of the radicals X 1 and X 2 is fluorine and the other is chlorine, or X 1 and X 2 are both fluorine.
6. A reactive dye according to claim 1 , wherein T is a group of formula
wherein y is vinyl, β-chloroethy or β-sulfatoethyl.
7. A reactive dye according to claim 1 , wherein V 1 and V 2 are N.
8. A reactive dye according to claim 1 , wherein A is a radical of formula
in which formulae (R 8 ) 0-3 denotes from 0 to 3 identical or different substituents selected from the group consisting of C 1 -C 4 alkyl, C 1 -C 4 alkoxy, halogen, carboxy and sulfo,
wherein (R 9 ) 0-4 denotes from 0 to 4 identical or different substituents selected from the group consisting of halogen, nitro, cyano, trifluoromethyl, sulfamoyl, carbamoyl, C 1 -C 4 alkyl, C 1 -C 4 alkoxy, amino, acetylamino, ureido, hydroxy, carboxy, sulfomethyl and sulfo,
in which formulae R 10 is hydrogen, C 1 -C 4 alkanoyl, benzoyl or a halotriazinyl radical of the formula
in which T 1 is a reactive radical of formula
R 4 is hydrogen, C 1 -C 4 alkyl unsubstituted or substituted by hydroxy, sulfo, sulfato, carboxy or by cyano, or a radical
wherein R 5 is as defined hereinbelow,
R 5 is hydrogen, hydroxy, sulfo, sulfato, carboxy, cyano, halogen, C 1 -C 4 alkoxycarbonyl, C 1 -C 4 alkanoyloxy, carbamoyl or a group —SO 2 —Y,
R 6 is hydrogen or C 1 -C 4 alkyl,
alk and alk 1 are each independently of the other linear or branched C 1 -C 6 alkylene,
arylene is an unsubstituted or sulfo-, carboxy-, hydroxy-, C 1 -C 4 alkyl-, C 1 -C 4 alkoxy- or halo-substituted phenylene or naphthylene radical,
Y is vinyl or a radical —CH 2 —CH 2 —U and U is a leaving group,
Y 1 is a group —CH(Hal)—CH 2 (Hal) or —C(Hal)═CH 2 , wherein Hal is chlorine or bromine,
W is a group —SO 2 —NR 6 —, —CONR 6 — or —NR 6 CO—, wherein R 6 is as defined hereinabove,
Q is a radical —O— or —NR 6 —, wherein R 6 is as defined hereinabove,
n is the number 0 or 1,
X 2 ′ is halogen, and
R 3 ′ is hydrogen or unsubstituted or substituted C 1 -C 4 alkyl,
in which formulae (R 11 ) 0-3 denotes from 0 to 3 identical or different substituents selected from the group consisting of C 1 -C 4 alkyl, C 1 -C 4 alkoxy, halogen, carboxy and sulfo,
wherein R 12 and R 14 are each independently of the other hydrogen, C 1 -C 4 alkyl or phenyl and R 13 is hydrogen, cyano, carbamoyl or sulfomethyl,
wherein (R 15 ) 0-2 denotes from 0 to 2 identical or different substituents selected from the group consisting of C 1 -C 4 alkyl, C 1 -C 4 alkoxy, halogen, carboxy and sulfo; and y is as defined hereinabove,
wherein (R 16 ) 0-2 denotes from 0 to 2 identical or different substituents selected from the group consisting of C 1 -C 4 alkyl, C 1 -C 4 alkoxy, halogen, carboxy and sulfo, and y has the definitions given hereinabove,
in which formulae (R 8 ) 0-3 denotes from 0 to 3 identical or different substituents selected from the group consisting of C 1 -C 4 alkyl, C 1 -C 4 alkoxy, halogen, carboxy and sulfo, (R 8 ′) 0-3 denotes from 0 to 3 identical or different substituents selected from the group consisting of C 1 -C 4 alkyl, C 1 -C 4 alkoxy, acetylamino, halogen, carboxy, sulfo, C 1 -C 4 hydroxyalkoxy and C 1 -C 4 sulfatoalkoxy, (R 9 ) 0-4 denotes from 0 to 3 identical or different substituents selected from the group consisting of halogen, nitro, cyano, trifluoromethyl, sulfamoyl, carbamoyl, C 1 -C 4 alkyl, C 1 -C 4 alkoxy, amino, acetylamino, ureido, hydroxy, carboxy, sulfomethyl and sulfo, (R 10 ′) 0-3 denotes from 0 to 3 identical or different substituents selected from the group consisting of C 1 -C 4 alkyl, C 1 -C 4 alkoxy, halogen, carboxy and sulfo, and Y is as defined hereinabove,
wherein Pc is the radical of a metal phthalocyanine; R is —OH and/or —NR 18 R 19 ; R 18 and R 19 are each independently of the other hydrogen or unsubstituted or hydroxy- or sulfo-substituted C 1 -C 4 alkyl; R 17 is hydrogen or C 1 -C 4 alkyl; E is a phenylene radical unsubstituted or substituted by C 1 -C 4 alkyl, halogen, carboxy or by sulfo or is a C 2 -C 6 alkylene radical; and k is from 1 to 3,
wherein E′ is a phenylene radical unsubstituted or substituted by C 1 -C 4 alkyl, halogen, carboxy or by sulfo or is a C 2 -C 6 alkylene radical, r, s, v and v′ are each independently of the others the number 0 or 1 and Y is as defined hereinabove, or
wherein G is a phenylene radical unsubstituted or substituted by C 1 -C 4 alkyl, C 1 -C 4 alkoxy, halogen, carboxy or by sulfo, or is a cyclohexylene, phenylenemethylene or C 1 -C 6 alkylene radical, each of which contains at least 2 sulfo groups.