Fibre reactive formazan dyes, their preparation and their use
A reactive dye of formula wherein Z 1 and Z 2 are each independently of the other vinyl or a radical —CH 2 —CH 2 —Y and Y is a group removable under alkaline conditions, n is the number 1, 2, 3 or 4, m is the number 2, 3 or 4, q is the number 0 or 1, and the substituents —(SO 3 H) n , —SO 2 —Z 1 and —NH—CO—(CH 2 ) m —SO 2 —Z 2 are bound to the benzene rings A, B and/or C, said benzene rings A, B and/or C are optionally further substituted by at least one substituent selected from the group C 1 -C 4 alkyl, C 1 -C 4 alkoxy and halogen, is suitable for dyeing and printing cellulosic or amide-group-containing fibre materials.
1. A reactive dye of formula
wherein
Z 1 and Z 2 are each independently of the other vinyl or a radical —CH 2 —CH 2 —Y and Y is a group removable under alkaline conditions,
n is the number 1, 2, 3 or 4,
m is the number 2, 3 or 4,
q is the number 0 or 1, and
the substituents —(SO 3 H) n , —SO 2 —Z 1 and —NH—CO—(CH 2 ) m —SO 2 —Z 2 are bound to the benzene rings A, B and/or C, and said benzene rings A, B and/or C are optionally further substituted by at least one substituent selected from the group C 1 -C 4 alkyl, C 1 -C 4 alkoxy and halogen.
2. A reactive dye according to claim 1 , wherein
Y is —Cl, —Br, —F, —OSO 3 H, —SSO 3 H, —OCO—CH 3 , —OPO 3 H 2 , —OCO—C 6 H 5 , —OSO 2 —(C 1 -C 4 alkyl) or —OSO 2 —N(C 1 -C 4 alkyl) 2 .
3. A reactive dye according to claim 1 , wherein Y is —Cl or —OSO 3 H.
4. A reactive dye according to claim 1 , wherein n is the number 2.
5. A reactive dye according to claim 1 , wherein m is the number 3.
6. A reactive dye according to claim 1 , wherein q is the number 1.
7. A reactive dye according to claim 1 , wherein the benzene rings A, B and/or C are devoid of further substituents from the group C 1 -C 4 alkyl, C 1 -C 4 alkoxy and halogen.
8. A reactive dye according to claim 1 , wherein
Z 1 and Z 2 are each independently of the other vinyl or a radical —CH 2 —CH 2 —Y and Y is —Cl or —OSO 3 H,
n is the number 2,
m is the number 3,
q is the number 1, and
the benzene rings A, B and/or C are devoid of further substituents from the group C 1 -C 4 alkyl, C 1 -C 4 alkoxy and halogen.
9. A reactive dye according to claim 1 , wherein the reactive dye of formula (1) is a dye of formula
wherein
Z 1 is vinyl or a radical —CH 2 —CH 2 —Y and Y is —OSO 3 H, and
Z 2 is vinyl or a radical —CH 2 —CH 2 —Y and Y is —Cl.
10. A process for the preparation of the reactive dye of formula (1), which comprises reacting with one another a compound of formula
and a compound of formula
X—CO—(CH 2 ) m —SO 2 —Z 2 (3)
wherein X is a replaceable group,
Z 1 and Z 2 are each independently of the other vinyl or a radical —CH 2 —CH 2 —Y and Y is a group removable under alkaline conditions,
n is the number 1, 2, 3 or 4,
m is the number 2, 3 or 4,
q is the number 0 or 1, and
the substituents —(SO 3 H) n , —SO 2 —Z 1 and —NH 2 are bound to the benzene rings A, B and/or C, and said benzene rings A, B and/or C are optionally further substituted by at least one substituent selected from the group C 1 -C 4 alkyl, C 1 -C 4 alkoxy and halogen.
11. A process for the dyeing or printing of hydroxyl-group-containing or nitrogen-containing fibre materials, wherein a reactive dye according to claim 1 is used.
12. An aqueous ink comprising the reactive dye of claim 1 .
13. A process for ink-jet printing, wherein an aqueous ink according to claim 12 is used.
14. A cellulosic fibre material dyed using a reactive dye according to claim 1 .
15. A process for the dyeing or printing of hydroxyl-group-containing or nitrogen-containing fibre materials with a reactive dye according to claim 10 .