Reactive dyes, process for their preparation and their use

• US 6,451,072 B1
• Filed: 03/24/2000
• Issued: 09/17/2002
• Est. Priority Date: 03/30/1999
• Status: Expired due to Fees

• Current Assignee: Huntsman International LLC (Huntsman Corporation)
• Original Assignee: CIBA Specialty Chemicals
• Inventors: Tzikas, Athanassios, Deitz, Rolf
• Primary Examiner(s): EINSMANN, MARGARET V
• Application Number:
  US09/535,916
• Time in Patent Office: 907 Days
• Field of Search: 854/9, 891/8, 868/7, 868/8, 863/7, 534/617, 534/635, 534/582, 534/598, 534/642, 534/637
• US Class Current: 8/549
• CPC Class Codes: C09B 62/03 Disazo or polyazo dyes
• CPC Class Codes: C09B 62/09 Disazo or polyazo dyes
• CPC Class Codes: C09B 62/4415 Disazo or polyazo dyes
• CPC Class Codes: Y10S 8/918 Cellulose textile

Abstract

Reactive dyes of formula (1)

wherein

A is phenyl or naphthyl, each of which is unsubstituted or substituted by halogen, C₁-C₄alkyl, C₁-C₄alkoxy, carboxy, sulfo or a fiber-reactive group of formula (2a), (2b), (2c), (2d) or (2e)

—SO₂—Y  (2a),

—NH—CO—(CH₂)_l—SO₂—Y  (2b),

—CONH—(CH₂)_m—SO₂—Y  (2c),

—NH—CO—CH(Hal)—CH₂Hal  (2d)

or

—NH—CO—C(Hal)═CH₂  (2e),

B is an aliphatic linking group,

D is the radical of a diazo component of the benzene or naphthalene series,

R₁ is hydrogen or unsubstituted or substituted C₁-C₄alkyl,

R₂ is hydrogen, cyano, carbamoyl or sulfomethyl,

R₃ is hydrogen or C₁-C₄alkyl,

R is hydrogen or unsubstituted or substituted C₁-C₄alkyl or corresponds to a radical of formula (3)

 wherein B, D, R₂ and R₃ have the meanings cited above,

X₁ is halogen, hydroxy, C₁-C₄alkoxy, unsubstituted or substituted C₁-C₄alkylthio or amino, or a N-heterocycle which may contain additional heteroatoms,

Hal is chloro or bromo,

Y is vinyl or a —CH₂—CH₂—U radical, U is a group a which is removable with alkali, and l and m are each independently of the other the number 2, 3 or 4,

with the proviso that A and D are not simultaneously a phenyl radical which is substituted by the radical of formula (2a) if R is β-hydroxyethyl or β-sulfatoethyl and R₁ is C₁-C₄alkyl, are particularly suitable for dyeing cotton and give dyeings having very good allround fastness properties.

Claims

1. A reactive dye of formula (1)

wherein

A is phenyl or naphthyl, each of which is unsubstituted or substituted by halogen, C₁-C₄alkyl, C₁-C₄alkoxy, carboxy, sulfo or a fibre-reactive group of formula (2a), (2b), (2c), (2d) or (2e)

2. A reactive dye according to claim 1, wherein

A is phenyl which is substituted by 1 to 2 identical or different substituents selected from the group consisting of methyl, methoxy, sulfo and a fibre-reactive group of formula (2a),

wherein Y is vinyl or β

-sulfatoethyl.

3. A reactive dye according to claim 1, wherein

B is straight-chain or branched C₂-C₆alkylene.

4. A reactive dye according to claim 1, wherein

R₁ is hydrogen or C₁-C₄alkyl.

5. A reactive dye according to claim 1, wherein

R₁ is hydrogen.

6. A reactive dye according to claim 1, wherein

R₂ is carbamoyl or sulfomethyl, and

R₃ is C₁-C₄alkyl.

7. A process for the preparation of a reactive dye according to claim 1, which comprises reacting about 1 molar equivalent each of an amine of formula (8)

of a compound of formula (9)

of a compound of formula (10)

in any sequence with each other, wherein A, B, D, R₁, R₂, R₃ and R have the meanings given in claim 1 and X is halogen.

8. A reactive dye according to claim 1, wherein

X₁ is chloro or fluoro.

9. A reactive dye according to claim 1, wherein

at least one of A and D contains a fibre-reactive group.

10. A reactive dye according to claim 1, wherein

D is a radical of formula (7) or (6j′

)

 

wherein

(R₈)_0-3 is 0 to 3 identical or different substituents selected from the group consisting of halogen, C₁-C₄alkyl, C₁-C₄alkoxy, carboxy and sulfo,

Z₂ may be a radical of formula (2a), (2b), (2c), (2d), (2e), (2f) or (2g)

11. A reactive dye according to claim 1, wherein D corresponds to a radical of formula (7a), (7b), (7c), (7d) or (7e)

wherein

(R₈)_0-2 is 0 to 2 identical or different substituents selected from the group consisting of halogen, C₁-C₄alkyl, C₁-C₄alkoxy and sulfo,

Y₁ is a —

CH(Br)—

CH₂—

Br or —

C(Br)═

CH₂ radical,

Y is vinyl, β

-chloroethyl or β

-sulfatoethyl, and

m is the number 2 or 3.

12. A reactive dye according to claim 11, which corresponds to formula (1a)

wherein

A is phenyl which is substituted by 1 to 2 identical or different substituents selected from the group consisting of methyl, methoxy, sulfo and the fibre-reactive group of formula —

SO₂—

Y (2a), wherein Y is vinyl or β

-sulfatoethyl,

B is straight-chain or branched C₂-C₆alkylene,

D corresponds to a radical of formula (7a), (7b), (7c), (7d) or (7e), wherein (R₈)_0-2, Y, Y₁ and m have the meanings given in claim 11,

R₂ is carbamoyl or sulfomethyl,

R corresponds to a radical of formula (3a)

 

wherein B, D and R₂ have the meanings cited above, and

X₁ is chloro or fluoro.

13. A process for dyeing or printing a fibre material containing hydroxyl groups or nitrogen, which comprises applying to said fibre material a reactive dye of formula (1) according to claim 1.

14. A process according to claim 13, wherein said fibre material is cellulosic fibre material.

15. A process according to claim 13, wherein said fibre material is cotton.