Fibre-reactive azo dyes, their preparation and their use
Reactive dyes of formula (1) wherein R 1 , R 2 , R 3 and R 4 are each independently of the others hydrogen or unsubstituted or substituted C 1 -C 4 alkyl, (R 5 ) s denotes s identical or different substituents selected from the group halogen, sulfo, carboxy, C 1 -C 4 alkyl and C 1 -C 4 alkoxy, B is an aliphatic bridging member, X 1 and X 2 are halogen, r is an integer from 0 to 2, s is an integer from 0 to 3, and n and m are each independently of the other a number 1 or 2, and Z is a fibre-reactive group of formula —SO 2 —Y (2a), —NH—CO—(CH 2 ) K —SO 2 —Y (2b), —CONH—(CH 2 )I—SO 2 —Y (2c), —NH—CO—CH(Hal)-CH 2 -Hal (2d) or —NH—CO—C(Hal)=CH 2 (2e) wherein Hal is chlorine or bromine, k and I are each independently of the other a number 2, 3 or 4, and Y is vinyl or a radical —CH 2 —CH 2 —U and U is a group removable under alkaline conditions are suitable for dyeing cellulosic or amide-group-containing fibre materials.
1 . A reactive dye of formula
wherein
R 1 , R 2 , R 3 and R 4 are each independently of the others hydrogen or unsubstituted or substituted C 1 -C 4 alkyl,
(R 5 ) s denotes s identical or different substituents selected from the group halogen, sulfo, carboxy, C 1 -C 4 alkyl and C 1 -C 4 alkoxy,
B is an aliphatic bridging member,
X 1 and X 2 are halogen,
r is an integer from 0 to 2,
s is an integer from 0 to 3, and
n and m are each independently of the other a number 1 or 2, and
Z is a fibre-reactive group of formula
—SO 2 —Y (2a),
—NH—CO—(CH 2 ) k —SO 2 —Y (2b),
—CONH—(CH 2 ) I —SO 2 —Y (2c),
—NH—CO—CH(Hal)-CH 2 -Hal (2d) or
—NH—CO—C(Hal)=CH 2 (2e)
wherein
Hal is chlorine or bromine,
k and I are each independently of the other a number 2, 3 or 4, and
Y is vinyl or a radical —CH 2 —CH 2 —U and U is a group removable under alkaline conditions.
2 . A reactive dye according to claim 1 , wherein
R 1 , R 2 , R 3 and R 4 are each independently of the others hydrogen or C 1 -C 4 alkyl.
3 . A reactive dye according to claim 1 , wherein
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.
4 . A reactive dye according to claim 1 , wherein X 1 and X 2 are chlorine.
5 . A reactive dye according to claim 1 , wherein n and m are in each case the number 2.
6 . A reactive dye according to claim 1 , wherein Z is a radical of formula
—SO 2 —Y (2a)
wherein
Y is vinyl or β-sulfatoethyl.
7 . A reactive dye according to claim 1 , corresponding to formula
wherein
R 2 and R 3 are hydrogen,
(R 5 ) s denotes s identical or different substituents selected from the group sulfo, methyl and methoxy,
B corresponds to a radical of formula —CH 2 —CH(R 7 )— or —(R 7 )CH—CH 2 — wherein R 7 is methyl,
X 1 and X 2 are chlorine,
s is an integer from 0 to 2, and
Z is a fibre-reactive group of formula
—SO 2 —Y (2a)
wherein Y is vinyl or β-sulfatoethyl.
8 . A process for the preparation of a reactive dye of formula (1) according to claim 1 , wherein approximately 1 molar equivalent of each of the compounds of formulae
are reacted with one another in a suitable order, R 1 , R 2 , R 3 , R 4 , R 5 , B, X 1 , X 2 , Y, Z, n, m, r and s in each case being as defined in claim 1 .
9 . A method of dyeing or printing of hydroxyl-group-containing or nitrogen-containing fibre materials, which comprises contacting said materials with a tinctorially effective amount of a reactive dye of formula (1) according to claim 1 .
10 . A method according to claim 9 , wherein cellulosic fibre materials are dyed or printed.
11 . An aqueous ink comprising a reactive dye of formula (1) according to claim 1 .
12 . A method of printing textile fibre materials, paper or plastics films by the inkjet printing method, which comprises contacting said materials with an aqueous ink according to claim 11 .
13 . A method according to claim 9 , wherein cotton-containing fibre materials are dyed or printed.