IP Library Granted Patent US 12,448,519
Granted Patent B2
US 12,448,519 · App. 17/921,169 · Granted Oct 21, 2025

Mixture of reactive dyes and their use for the dyeing or printing of textile fibre materials

Inventors: Hubert Jean-Luc Christnacher (Dietwiller, FR); Fanny Ehret (Reiningue, FR); Michael Nicollet (Village-Neuf, FR); Jean-Christophe Graciet (Village-Neuf, FR); Georg Roentgen (Freiburg, DE)
Assignee: Archroma (Switzerland) GmbH
C09B67/0045C09B29/30C09D11/033C09D11/037C09D11/328D06P1/06D06P3/666D06P5/30
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Quick Facts
Patent No.
US 12,448,519
App. No.
17/921,169
Granted
Oct 21, 2025
Kind
B2
Abstract

A dye mixture comprising at least one dye of formula (formula) and at least one dye of formula (formula), wherein R 1 is hydrogen or C 1 -C 4 alkyl, R 2 is hydrogen or C 1 -C 4 alkyl, C 1 -C 4 alkoxy or sulfo, Q 1 is a fibre-reactive radical of formula —(CH 2 ) 2- 3 —SO 2 —Y 2 (3a) or —(CH 2 ) 2-3 —O—(CH 2 ) 2-3 —SO 2 —Y 3 (3b), Q 2 has the meaning of Q 1 , or is hydrogen or C 1 -C 4 alkyl, X 1 and X 2 are each independently of the other halogen, 3-carboxypyridin-1-yl or 3-carbamoylpyridin-1-yl, Y 1 , Y 2 and Y 3 are each independently of the others vinyl or a radical —CH 2 —CH 2 —U and U is a group removable under alkaline conditions, Z 1 and Z 2 are each independently of the other —S0 2 -Y, wherein Y is vinyl or a radical —CH 2 —CH 2 —U and U is a group removable under alkaline conditions, M is hydrogen, an alkali metal or one equivalent of an alkaline earth metal, k and n are each independently of the other the number 0, 1 or 2, I and q are each independently of the other the number 0 or 1, m is the number 0 or 1, and wherein the diazo component of the dye of formula (1) and the diazo component of the dye of formula (2) each independently of the other are a benzene radical or a naphthyl radical, are suitable especially for the dyeing or printing of cellulosic fibre materials, exhibit a good build-up, a good fixation rate and good washing off properties of the unfixed dyes, and good all-round fastness properties.

Claims (49)

1. A dye mixture comprising at least one dye of formula

and at least one dye of formula

wherein

R 1 is hydrogen or C 1 -C 4 alkyl,

R 2 is hydrogen, C 1 -C 4 alkyl, C 1 -C 4 alkoxy or sulfo,

Q 1 is a fibre-reactive radical of formula

—(CH 2 ) 2-3 —SO 2 —Y 2   (3a) or

—(CH 2 ) 2-3 —O—(CH 2 ) 2-3 —SO 2 —Y 3   (3b),

Q 2 has the meaning of Q 1 , or is hydrogen or C 1 -C 4 alkyl,

X 1 and X 2 are each independently of the other halogen, 3-carboxypyridin-1-yl or 3-carbamoylpyridin-1-yl,

Y 1 , Y 2 and Y 3 are each independently of the others vinyl or a radical —CH 2 —CH 2 —U and U is a group removable under alkaline conditions,

Z 1 and Z 2 are each independently of the other —SO 2 —Y, wherein Y is vinyl or a radical —CH 2 —CH 2 —U and U is a group removable under alkaline conditions,

M is hydrogen, an alkali metal or one equivalent of an alkaline earth metal,

k and n are each independently of the other the number 0, 1 or 2,

I and q are each independently of the other the number 0 or 1,

m is the number 0 or 1, and

wherein the diazo component of the dye of formula (1) and the diazo component of the dye of formula (2) each independently of the other are a benzene radical or a naphthyl radical.

2. A dye mixture according to claim 1 , wherein the diazo component of the dye of formula (1) and the diazo component of the dye of formula (2) each are a naphthyl radical.

3. A dye mixture according to claim 1 , wherein I and q each are the number 0.

4. A dye mixture according to claim 1 , wherein m is the number 0.

5. A dye mixture according to claim 1 , wherein the dye of formula (1) is a dye of formula

wherein

R 1 , R 2 , X 1 , Y 1 , M and k each have the meanings given in claim 1 .

6. A dye mixture according to claim 1 , wherein the dye of formula (2) is a dye of formula

wherein

Q 1 , Q 2 , X 2 , M and n each have the meanings given in claim 1 .

7. A dye mixture according to claim 1 , wherein k and n each independently of the other are the number 1 or 2.

8. A dye mixture according to claim 1 , wherein R 2 is hydrogen or sulfo.

9. A dye mixture according to claim 1 , wherein X 1 and X 2 each are halogen.

10. A dye mixture according to claim 1 , wherein Y 1 , Y 2 and Y 3 are each independently of the others vinyl or a radical —CH 2 —CH 2 —U and U means Cl or —OSO 3 M, wherein M has the meanings given in claim 1 .

11. A dye mixture according to claim 1 , wherein Q 1 and Q 2 are each a fibre-reactive radical of formula (3a).

12. A method for the dyeing or printing of hydroxy-group-containing or nitrogen-containing fibre materials, which method comprises contacting the fibre material with a dye mixture according to claim 1 .

13. A method according to claim 12 , wherein the fibre material comprises cellulosic fibre material.

14. A reactive dye of formula

wherein

R 1 is hydrogen or C 1 -C 4 alkyl,

R 2 is hydrogen, C 1 -C 4 alkyl, C 1 -C 4 alkoxy or sulfo,

X 1 is halogen, 3-carboxypyridin-1-yl or 3-carbamoylpyridin-1-yl,

Y 1 is vinyl or a radical —CH 2 —CH 2 —U and U is a group removable under alkaline conditions,

Z 1 is —SO 2 —Y, wherein Y is vinyl or a radical —CH 2 —CH 2 —U and U is a group removable under alkaline conditions,

M is hydrogen, an alkali metal or one equivalent of an alkaline earth metal,

k is the number 0, 1 or 2,

l is the number 0 or 1, and

wherein the diazo component of the dye of formula (1b) is a benzene radical or a naphthyl radical.

15. The reactive dye of claim 14 , wherein R 2 is sulfo.

16. A method for the dyeing or printing of hydroxy-group-containing or nitrogen-containing fibre materials, which method comprises contacting the fibre material with the reactive dye according to claim 15 .

17. The method according to claim 16 , wherein the fibre material comprises cellulosic fibre material.

18. An aqueous ink comprising the dye mixture according to claim 1 .

19. An aqueous ink comprising the reactive dye according to claim 15 .

Assignments (3)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Oct 31, 2024
From: HUNTSMAN ADVANCED MATERIALS (SWITZERLAND) GMBH
To: HUNTSMAN TEXTILE EFFECTS (SWITZERLAND) GMBH
Reel/Frame 069095/0414 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Sep 3, 2024
From: CHRISTNACHER, HUBERT JEAN-LUC; EHRET, FANNY; NICOLLET, MICHAEL; GRACIET, JEAN CHRISTOPHE; ROENTGEN, GEORG
To: ARCHROMA (SWITZERLAND) GMBH
Reel/Frame 068830/0749 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Nov 6, 2023
From: HUNTSMAN ADVANCED MATERIALS (SWITZERLAND) GMBH
To: HUNTSMAN TEXTILE EFFECTS (SWITZERLAND) GMBH
Reel/Frame 065467/0755 →
Priority Claims (1)
EP 20171675 · Apr 27, 2020 · regional
Continuity (1)
Related Publication 20230167304A1 · Jun 1, 2023
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