Fiber-reactive azo dyes, their preparation and their use

1. A reactive dye of formula

wherein

A is the radical of a monoazo, polyazo, metal complex azo, anthraquinone, phthalocyanine, formazan or dioxazine chromophore,

Q 1 and Q 2 are each independently of the other hydrogen or unsubstituted or substituted C 1 –C 4 alkyl, (Q 3 ) n denotes n substituents selected from the group consisting of C 1 –C 4 alkyl, C 1 –C 4 alkoxy, halogen and sulfo,

X is halogen, 3-carboxypyridin-1-yl, 3-carbamoylpyridin-1-yl, hydroxy, C 1 –C 4 alkoxy unsubstituted or substituted in the alkyl moiety, phenoxy unsubstituted or substituted in the phenyl moiety,

C 1 –C 4 alkylthio unsubstituted or substituted in the alkyl moiety, unsubstituted or substituted amino, or an N-heterocycle which may or may not contain further hetero atoms,

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

k is a number 2, 3, 4, 5 or 6,

m is a number 0 or 1, and

n is a number 0, 1 or 2, with the proviso that

when A denotes a monoazo chromophore it is not directly linked to the triazinyl radical through a hydroxynaphthalenesulfonic acid coupling component and does not denote a radical of formula

2. A reactive dye according to claim 1 , wherein

Q 1 and Q 2 are hydrogen.

3. A reactive dye according to claim 1 , wherein

X denotes fluorine or chlorine.

4. 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 .

5. A reactive dye according to claim 1 , wherein

Q 3 is sulfo.

6. A reactive dye according to claim 1 , wherein

k is the number 3.

7. A reactive dye according to claim 1 , wherein

m is the number 1.

8. A reactive dye according to claim 1 , wherein

n is the number 1.

9. A reactive dye according to claim 1 , wherein

A is a mono- or dis-azo dye radical of formula

wherein (R 4 ) 0-3 denotes from 0 to 3 identical or different substituents selected from the group consisting of C 1 –C 4 alkyl, C 1 –C 4 alkoxy, halogen, carboxy and sulfo,

(R 5 ) 0-3 denotes from 0 to 3 identical or different substituents selected from the group consisting of halogen, nitro, cyano, trifluoromethyl, sulfamoyl, carbamoyl, C 1 –C 4 alkyl; C 1 –C 4 alkoxy unsubstituted or substituted by hydroxy, sulfato or C 1 –C 4 alkoxy; amino, C 2 –C 4 alkanoylamino, ureido, hydroxy, carboxy, sulfomethyl, C 1 –C 4 alkylsulfonylamino and sulfo, and

Z 1 denotes a radical of formula

—SO 2 —Y  (2a),

—CONR 2 —(CH 2 ) 1 —SO 2 —Y  (2c),

—NH—CO—CH(Hal)-CH 2 -Hal  (2d),

—NH—CO—C(Hal)═CH 2   (2e) or

wherein

Hal is chlorine or bromine,

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

T 1 has independently the same definitions as X 1 , or is a non-fibre-reactive substituent or a fibre-reactive radical of formula

wherein

R 1 and R 1a are each independently of the other hydrogen or C 1 –C 4 alkyl,

R 2 is hydrogen, C 1 –C 4 alkyl unsubstituted or substituted by hydroxy, sulfo, sulfato, carboxy or cyano, or a radical

R 3 is hydrogen, hydroxy, sulfo, sulfato, carboxy, cyano, halogen, C 1 –C 4 alkoxycarbonyl, C 1 –C 4 alkanoyloxy, carbamoyl or a group —SO 2 —Y,

alk and alk 1 are each independently of the other linear or branched C 1 –C 6 alkylene,

arylene is a phenylene or naphthylene radical unsubstituted or substituted by sulfo, carboxy, C 1 –C 4 alkyl, C 1 –C 4 alkoxy or halogen,

Q is a radical —O— or —NR 1 — wherein R 1 is as defined above,

W is a group —SO 2 —NR 2 —, —CONR 2 — or —NR 2 CO— wherein R 2 is as defined above,

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

Y 1 is a group —CH(Hal)-CH 2 -Hal or —C(Hal)═CH 2 , Hal being as defined above, and

I is an integer from 1 to 6 and t is a number 0 or 1,

wherein R 6 is hydrogen, C 1 –C 4 alkyl, sulfophenyl, C 2 –C 4 alkanoyl, benzoyl or a radical of formula (2f) given above,

wherein (R 7 ) 0-3 denotes from 0 to 3 identical or different substituents selected from the group consisting of C 1 –C 4 alkyl, C 1 –C 4 alkoxy, halogen, carboxy and sulfo,

wherein R 8 and R 10 are each independently of the other hydrogen, C 1 –C 4 alkyl or phenyl, and R 9 is hydrogen, cyano, carbamoyl or sulfomethyl,

wherein (R 4 ) 0-3 and Z 1 each have the definitions given above,

wherein (R 4 ) 0-3 and (R 5 ) 0-3 each have the definitions given above, and (R11) 0-3 denotes from 0 to 3 identical or different substituents selected from the group consisting of C 1 –C 4 alkyl, C 1 –C 4 alkoxy, halogen, carboxy and sulfo, and Z 1 has the definitions given above.

10. A reactive dye, according to claim 9 , of formula

wherein

Q 1 and Q 2 are hydrogen,

A is a mono- or dis-azo dye radical of formula (11d), (11e), (11f), (11g), (11i), (11j), (11k), (11l), (11m), (11p) or (11q) according to claim 9 ,

X is fluorine or chlorine,

Y is vinyl, β-chloroethyl or β-sulfatoethyl, preferably vinyl or β-chloroethyl, and

k is a number 2 or 3.

11. A process for the preparation of a reactive dye according to claim 1 , wherein approximately one molar equivalent of a compound of formula

approximately one molar equivalent of a compound of formula

A-NHQ 2   (13),

or suitable precursors of the compounds of formula (12) or (13), and approximately one molar equivalent of a compound of formula

are reacted with one another step-wise, in any order, or, if using precursors of compounds of formula (12) or (13), the intermediates obtained are converted into the desired dyes and, where appropriate, a further transformation reaction is subsequently carried out, A, Q 1 , Q 2 , Q 3 , Y, k, m and n in each case having the definitions given in claim 1 and X being halogen.

12. 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 according to claim 1 .

13. A method according to claim 12 , wherein cellulosic fibre materials are dyed or printed.

14. An aqueous ink comprising a reactive dye of formula (1) according to claim 1 .

15. A method of printing textile fibre materials, paper or plastics films by the inkjet printing method, which comprises printing said materials with an aqueous ink according to claim 14 .