Fibre reactive dyes, their preparation and their use
A reactive dye of formula wherein M is hydrogen, an alkali metal or one equivalent of an alkaline earth metal, Z 1 is vinyl, β-sulfatoethyl or the radical —NHCO—(CH 2 ) 3 —SO 2 —CH 2 CH 2 Cl; R 1 denotes H or sulfo; and R 2 is H, methyl, methoxy or sulfo, n is the number 3; Y is vinyl or a radical —CH 2 —CH 2 -U and U is —Cl or —OSO 3 H, is suitable for dyeing and printing cellulosic or amide-group-containing fibre materials.
1. A reactive dye of formula
wherein
M is hydrogen, an alkali metal or one equivalent of an alkaline earth metal,
Z1 is vinyl, β-sulfatoethyl, β-sulfatoethylsulfonyl or the radical —NHCO—(CH 2 ) 3 —SO 2 —CH 2 CH 2 Cl,
R1 denotes H or sulfo, and
R2 is H, methyl, methoxy or sulfo,
n is the number 3,
Y is vinyl or a radical —CH 2 —CH 2 -U and U is —Cl or —OSO 3 H.
2. The reactive dye of formula (1) according to claim 1 , wherein Z1 is β-sulfatoethyl or —NHCO—(CH 2 ) 3 —SO 2 —CH 2 CH 2 Cl.
3. The reactive dye of formula (1) according to claim 1 , wherein R 1 denotes H.
4. The reactive dye of formula (1) according to claim 1 , wherein Y is a radical CH 2 —CH 2 -U and U is —Cl or —OSO 3 H.
5. The reactive dye according to claim 1 , wherein the reactive dye of formula (1) is a dye of formula
wherein
M is as defined in claim 1 ,
Z1 is β-sulfatoethyl, β-sulfatoethylsulfonyl or —NHCO—(CH 2 ) 3 —SO 2 —CH 2 CH 2 Cl,
R 1 denotes H or sulfo, and
R 2 is H, methyl, methoxy or sulfo.
6. A dye mixture comprising:
(A) 20-60% by weight of one or more reactive dyes of formula (1) according to claim 1 , and
(B) 40-80% by weight of at least one blue, yellow, orange or brown dyeing reactive dye different from the dye of formula (1),
each percentage being based on the sum total of all dyes.
7. The dye mixture according to claim 6 comprising one or more dyes selected from C.I. R BL 220, C.I. R BL 235, C.I. R BL 19 and C.I. R BL 279 as component (B).
8. A process for the preparation of the reactive dye of formula (1), which comprises:
(a) diazotising a compound of the formula
wherein R 1 , R 2 and Z 1 have the meanings as defined in claim 1 and R 6 denotes H or C 1 -C6 alkyl;
and reacting the diazonium salt so obtained with a coupling component of formula
wherein M is as defined in claim 1 ;
whereby an azo compound of formula
is obtained, wherein R 1 , R 2 , Z 1 , R 6 and M are as defined in claim 1 ;
(b) reacting a compound of formula
wherein M is as defined in claim 1 ,
with a compound of formula
Cl—CO—(CH 2 ) n —SO 2 Y (7),
wherein Y and n are as defined in claim 1 ,
thereby providing a compound of formula
wherein M, Y and n are as defined in claim 1 ;
(c) diazotising the compound of the formula (5) prepared in step (a) and reacting the diazonium salt so obtained with the coupling component of formula (8) prepared in step (b); and
(d) reacting the bisazo dye prepared in step (c) with a Cu(II) salt in aqueous solution at pH <7 thus providing the copper complex dye of formula (1) according to claim 1 .
9. A process for the dyeing or printing of hydroxyl-group-containing or nitrogen-containing fibre materials, wherein a reactive dye according to claim 1 or a mixture of reactive dyes according to claim 6 or 7 is used.
10. An aqueous ink comprising at least one dye of formula (1).
11. A reactive dye of formula
12. A process for the dyeing or printing of hydroxyl-group-containing or nitrogen-containing fibre materials, wherein the reactive dye according to claim 11 is used.
13. An aqueous ink comprising at least one dye according to claim 11 .
14. A reactive dye of formula
15. A process for the dyeing or printing of hydroxyl-group-containing or nitrogen-containing fibre materials, wherein the reactive dye according to claim 14 is used.
16. An aqueous ink comprising at least one dye according to claim 14 .