Fibre reactive formazan dyes, their preparation and their use

Patent metadata

Field	Value
Publication number	US-10550268-B2
Application number	US-201616047969-A
Country	US
Kind code	B2
Filing date	Dec 6, 2016
Priority date	Jan 29, 2016
Publication date	Feb 4, 2020
Grant date	Feb 4, 2020

Abstract

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.

First claim

What is claimed is:

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 .

Assignees

• Huntsman Int Llc

Inventors

• Christnacher Hubert Jean-Luc
• Ehret Fanny
• Tzikas Athanassios
• Hildebrand Rainer
• Nicollet Michael

Classifications

• D06P1/384

  reactive group not directly attached to heterocyclic group · CPC title

• D06P5/30

  Ink jet printing · CPC title

• C09B62/5036 Primary

  Formazane dyes · CPC title

• D06P1/38

  using reactive dyes · CPC title

• C09D11/328

  characterised by dyes · CPC title