Reactive dye mixtures

Details Reactive dye mixtures Reactive dye mixtures

2001-12-17

2004-10-05

Einsmann, Margaret (Department: 1751)

Bleaching and dyeing; fluid treatment and chemical modification

Reactive dye composition, process, or product

Alkylene sulfato, halotriazine, halodiazine,...

C008S641000

Reexamination Certificate

active

06800099

ABSTRACT:

This invention relates to mixtures of reactive dyes, in particular to mixtures of reactive dyes containing, as one component, a disazo dye derived from H-acid.
As is well known, reactive dyes contain at least one substituent capable of taking part in a reaction with a group present on a fabric to be dyed during the dyeing operation.
EP-A-0149170 discloses a range of dyes of the formula
in which one X is hydrogen and the other sulpho, each of Y
1
and Y
2
independently is a group —CH═CH
2
, —CH
2
CH
2
OSO
3
H, —CH
2
CH
2
SSO
3
H, —CH
2
CH
2
Cl or —CH
2
CH
2
OR, and R is a low molecular weight alkanoyl, benzoyl or benzenesulphonyl group, optionally substituted by a C
1-4
alkyl, C
1-4
alkoxy, halogen, carboxy or sulpho group.
A typical dye has the formula
EP-A-0149170 refers only to individual dyes, not mixtures thereof.
On the other hand, each of EP-A-0224224, EP-A-0679697, EP-A-0531968, EP-A-0668328 and EP-A-0600322 discloses respective mixtures of dyes, one of which components is a disazo dye derived from H-acid. One particular example of such a dye has the formula
This dye is available commercially as C.I. Reactive Black 5 and is added to other dyes as a dulling agent where appropriate.
We find surprisingly that the fastness of a dye mixture can be improved if the dye mixture contains, as a component thereof, a dye of the formula (A)
wherein each of Y
1
and Y
2
, independently, is a vinyl group or a group of the formula —CH
2
CH
2
Q in which Q is a leaving group removable under alkaline conditions to provide a vinyl group.
The dye mixture may contain, in addition to component (A), any of a wide range of dyes.
More particularly, the present invention provides a dye mixture comprising a reactive dye of the formula (A), given and defined above; and
at least one reactive dye (B) selected from
(I) a monoazopyrazole dye of the formula
wherein R
1
is an aryl group selected from phenyl and naphthyl groups optionally having at least one substituent thereon, the substituents, or each substituent independently, being selected from a sulphonic acid group and a salt thereof, a C
1-4
alkyl group, a C
1-4
alkoxy group, a hydroxy group, a carboxyl group, a chlorine atom, a vinyl sulphonyl group and a group SO
2
CH
2
CH
2
Q
1
in which Q
1
is a leaving group removable under alkaline conditions to provide a vinyl sulphonyl group;
R
2
is a phenyl or naphthyl group, optionally having a least one substituent thereon, the substituent, or each substituent, independently, being selected from a sulphonic acid group and a salt thereof, a C
1-4
alkyl group, a C
1-4
alkoxy group, a hydroxy group, a chlorine atom, a vinyl sulphonyl group, a group SO
2
CH
2
CH
2
Q
2
in which Q
2
is a leaving group removable under alkaline conditions to provide a vinyl sulphonyl group, a group Het and a group L
5
-Het, where Het is an optionally substituted aromatic heterocyclic reactive or non-reactive group or a reactive or non-reactive group having an aliphatic chain and L
5
is as defined below; and
R
6
is a methyl group, an amide group or a carboxyl group or a salt thereof;
each of R
40
and R
41
, independently, is an aryl group selected from phenyl and naphthyl groups, each of which, independently, is optionally substituted by a vinylsulphonyl group, a group SO
2
CH
2
CH
2
Q
1
in which Q
1
is a leaving group removable under alkaline conditions to provide a vinylsulphonyl group; or the group Het, where Het is as defined above;
at least one of R
1
, R
2
, R
40
and R
41
being, or having thereon at least one substituent which is, reactive;
each of L
1
, L
2
and L
5
independently is a linking group selected from N(R
20
), in which R
20
is hydrogen or C
1-4
alkyl; C(═O); C(═O)—O; S(═O)
2
; S(═O)—NH; C(═O)—NH; and NHC(═O)NH; and
each of x, y and z, independently, is zero or 1; and, when the group R
1
is substituted by a hydroxy group ortho to the azo group, a metallized derivative thereof;
(II) a monoazo or disazo dye of the formula
wherein:
Het is an optionally substituted aromatic heterocyclic reactive or non-reactive group or a reactive or non-reactive group having an aliphatic chain;
R
3
or each R
3
, independently, is a chlorine atom, a methyl group, a methoxy group, a sulphonic acid group or a salt thereof, or is an amino, group of the formula
 in which each of R
18
and R
19
, independently, is hydrogen, chloro, methyl, (C
1-4
alkyl) carbonyl, aminocarbonyl, vinylsulphonyl or a group SO
2
CH
2
CH
2
Q
1
, in which Q
1
is as defined above;
R
4
, or each R
4
independently, is hydrogen, a sulphonic acid group or a salt thereof, a C
1-8
alkyl (preferably a C
1-4
alkyl) group, a C
1-4
alkoxy group, a vinyl sulphonyl group or a group SO
2
CH
2
CH
2
Q
2
in which Q
2
is a leaving group removable under alkaline conditions to provide a vinyl sulphonyl group, which C
1-4
alkyl group or C
1-4
alkyl moiety of the C
1-4
alkoxy group is optionally interrupted by an oxygen atom to provide an ether group and is optionally substituted by a vinyl sulphonyl group or a group SO
2
CH
2
CH
2
Q
2
, in which Q
2
is as defined above; or R
4
(or when q is 2, each R
4
independently) is a phenyl group optitonally substituted by at least one sulphonic acid group or a salt thereof or at least one group Het, where Het is as defined above; or R
4
is a group Het, where Het is as defined above
R
5
is an aryl group selected from phenyl and naphthyl groups each optionally substituted by at least one sulphonic acid group or, a salt thereof or at least one group Het, as defined above;
R
20
is a hydrogen atom or a C
1-4
alkyl group;
R
21
is a hydrogen atom, a C
1-4
alkyl group, a sulphonic acid-C
1-4
alkyl group, a chloroalkylsulphonyl-C
1-4
alkyl group or a group Het, where Het is as defined above;
m is 1 or 2;
p is zero, 1 or 2;
q is zero, 1 or 2;
each of w
1
and w
2
is zero or 1; and
w
3
is 1, 2 or 3; and
when p is zero, q is zero;
at least one of R
4
, R
5
, R
18
, R
19
, R
21
and Het being, or having thereon at least one substituent which is, reactive;
(III) a monoazopyridone dye of the formula
wherein:
each of R
40
, R
41
, L
1
and L
2
is as defined above;
R
7
is optionally present and is a cyano group or the group —CH
2
SO
3
H or the group —C(═O)NH
2
;
each of R
24
and R
25
, independently, is a hydrogen atom, a C
1-4
alkyl group, a sulpho-C
1-4
alkyl group, or a carboxyl group;
n is 1 or 2;
r is zero or 1; and
each of s
1
and s
2
is zero or 1; and when R
40
is a phenyl or naphthyl group s
2
is 1;
at least one of R
40
and R
41
being, or having thereon at least one substituent which is, reactive;
(IV) a monoazonaphthyl dye of the formula
wherein:
each of R
1
, R
40
, R
41
, L
1
, L
2
, x, y and z is as defined above;
R
9
is CH
3
(C═O)—, Het (as defined above) or an aryl group selected from phenyl and naphthyl, which Het or aryl group is optionally substituted by at least one substituent, the or each substituent, independently, being selected from a sulphonic acid group and a salt thereof, a C
1-4
alkyl group, a C
1-4
alkoxy group, a hydroxy group, an amino group optionally substituted by at least one methyl or sulphato group, a vinyl sulphonyl group and a group SO
2
CH
2
CH
2
Q
1
in which Q
1
is as defined above;
R
35
is a C
1-4
alkyl or C
2-4
alkenyl group, which C
1-4
alkyl or C
2-4
alkenyl group is optionally substituted by at least one halogen atom, a sulphonic acid group or salt thereof, a chloroalkylsulphonyl group, a vinylsulphonyl group or —SO
2
CH
2
CH
2
Q
1
, where Q
1
is as defined above and which C
1-4
alkyl or C
2-4
alkenyl group optionally additionally contains at least one oxygen or sulphur atom in the chain thereof; the group Het (as defined above); or an aryl group selected from phenyl and naphthyl, which Het or aryl group is optionally substituted by at least one substituent, the substituent or each substituent independently, being selected from a sulphonic acid group and a salt thereof, a C
1-4
alkyl group, a C
1-4
alkoxy group, a halogen atom, a hydroxy group, an amino group optionally substitute

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