Mixtures of reactive dyes and their use

Details Mixtures of reactive dyes and their use Mixtures of reactive dyes and their use

2001-05-03

2003-10-07

Gupta, Yogendra N. (Department: 1751)

Bleaching and dyeing; fluid treatment and chemical modification

Reactive dye composition, process, or product

Alkylene sulfato, halotriazine, halodiazine,...

C008S543000, C008S641000, C008S918000

Reexamination Certificate

active

06630005

ABSTRACT:

The present invention relates to novel improved reactive dye mixtures which are particularly suitable for dyeing or printing nitrogen-containing or hydroxyl group-containing fibre materials by processes which are customarily used for reactive dyes and which yield dyeings which are fast to wet treatment and light; and to a process for the preparation of these dye mixtures, as well as to their use for dyeing or printing textile materials.
Accordingly, this invention relates to dye mixtures, which comprise at least one dye of formula (1)
together with at least one dye of formula (2)
wherein
R
1
, R
2
, R
4
and R
5
are each independently of one another hydrogen or unsubstituted or substituted C
1
-C
4
alkyl,
(R
3
)
0-2
is 0 to 2 identical or different substituents selected from the group consisting of halogen, C
2
-C
4
alkanoylamino, C
1
-C
4
alkyl and C
1
-C
4
alkoxy,
A
1
and A
2
are each independently of the other an unsubstituted or substituted phenylene radical or a C
1
-C
8
alkylene radical which may be interrupted by oxygen,
D is a radical of formula (3) or (4)
wherein
(R
6
)
0-2
is 0 to 2 identical or different substituents selected from the group consisting of halogen, C
2
-C
4
alkanoylamino, C
1
-C
4
alkyl and C
1
-C
4
alkoxy,
X
1
and X
2
are halogen, and
Y
1
and Y
2
are each independently of the other a fibre-reactive radical of formula (5a), (5b), (5c) or (5d)
—SO
2
—Z  (5a),
—CONH—(CH
2
)
m
—SO
2
—Z  (5b),
—NH—CO—CH(Hal)—CH
2
Hal  (5c) or
—NH—CO—C(Hal)═CH
2
  (5d),
wherein
m is the number 2, 3 or 4,
Hal is halogen, and
Z is vinyl or a radical —CH
2
—CH
2
—U, and U is a group which may be split off with alkali.
R
1
, R
2
, R
4
and R
5
defined as C
1
-C
4
alkyl may suitably be each independently of one another typically methyl, ethyl, propyl, isopropyl, butyl, sec-butyl, tert-butyl or isobutyl, preferably methyl or ethyl and, particularly preferably, methyl. The cited alkyl radicals may be unsubstituted or substituted by e.g. hydroxy, sulfo, sulfato, cyano or carboxyl. The corresponding unsubstituted alkyl radicals are preferred.
R
3
and R
6
defined as C
1
-C
4
alkyl may suitably be each independently of the other e.g. methyl, ethyl, propyl, isopropyl, butyl, sec-butyl, tert-butyl or isobutyl, preferably methyl or ethyl and, particularly preferably, methyl.
R
3
and R
6
defined as C
1
-C
4
alkoxy may suitably be each independently of the other e.g. methoxy, ethoxy, propoxy, isopropoxy, butoxy or isobutoxy, preferably methoxy or ethoxy and, particularly preferably, methoxy.
R
3
and R
6
defined as C
2
-C
4
alkanoylamino may suitably be each independently of the other e.g. acetylamino or propionylamino and, preferably, acetylamino.
R
3
and R
6
defined as halogen may suitably be each independently of the other e.g. fluoro, chloro or bromo, preferably chloro or bromo and, particularly preferably, chloro.
Hal is, for example, fluoro, chloro or bromo, preferably chloro or bromo, particularly preferably bromo.
m in the fibre-reactive group of formula (5b) is preferably the number 2.
X
1
and X
2
defined as halogen may suitably be each independently of the other e.g. fluoro, chloro or bromo.
Preferred dye mixtures are those, wherein
R
1
, R
2
, R
4
and R
5
are each independently of one another hydrogen or C
1
-C
4
alkyl, preferably hydrogen.
In the novel dye mixtures, D defined as a radical of formula (3) is, for example, a radical of formula
preferably a radical of formula (3.3).
In the novel dye mixtures, D defined as a radical of formula (4) is, for example, a radical of formula
preferably a radical of formula (4.1) or (4.6) and, particularly preferably, a radical of formula (4.1).
In a preferred embodiment of the dye mixtures of this invention, D defined as a radical of formula (3) is a radical of formula (3a)
and, defined as a radical of formula (4), a radical of formula (4a)
wherein
R
6
is hydrogen, C
1
-C
4
alkyl or C
1
-C
4
alkoxy, preferably hydrogen, methyl, ethyl, methoxy or ethoxy, more preferably methyl or methoxy and, very particularly preferably, methoxy.
Preferred dye mixtures are those, wherein X
1
and X
2
are each independently of the other fluoro or chloro, preferably chloro.
The meanings of X
1
and X
2
in the novel dye mixtures are preferably identical.
Suitable leaving groups U are, for example, —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
. U is preferably a group of formula —Cl, —OSO
3
H, —SSO
3
H, —OCO—CH
3
, —OCO—C
6
H
5
or —OPO
3
H
2
, more preferably —Cl or —OSO
3
H and, particularly preferably, —OSO
3
H.
If A
1
or A
2
in the novel dye mixtures are defined as an unsubstituted or substituted phenylene radical, suitable substituents are each independently of the other e.g. identical or different radicals selected from the group consisting of halogen, C
1
-C
4
alkyl, C
1
-C
4
alkoxy and sulfo, preferably of C
1
-C
4
alkyl, C
1
-C
4
alkoxy and sulfo and, particularly preferably, of methyl, methoxy and sulfo. The fibre-reactive Y
1
or Y
2
are in this case each independently of the other radicals of formula (5a), (5b), (5c) or (5d), preferably of formula (5a) or (5b), which radicals have the above-cited meanings and preferred meanings.
A
1
or A
2
defined as a C
1
-C
8
alkylene radical which may be interrupted by oxygen may suitably be each independently of the other e.g. ethylene, propylene, isopropylene, butylene, isobutylene, —(CH
2
)
2
—O—(CH
2
)
2
—, —(CH
2
)
3
—O—(CH
2
)
2
— or —(CH
2
)
3
—O—(CH
2
)
3
—. The fiber-reactive Y
1
or Y
2
are in this case preferably a radical of formula (5a), which has the above-cited meanings and preferred meanings. A
1
and A
2
are preferably a C
1
-C
6
alkylene radical which is correspondingly interrupted and, particularly preferably, a C
1
-C
4
alkylene radical such as ethylene or —(CH
2
)
2
—O—(CH
2
)
2
—.
In a preferred embodiment of the novel dye mixtures, the radicals of formulae —A
1
—Y
1
and A
2
—Y
2
in the dyes of formulae (1) and (2) are each independently of the other a radical of formula (6a), (6b) or (6c)
wherein
(R
7
)
0-2
is 0 to 2 identical or different substituents selected from the group consisting of sulfo, methyl or methoxy,
Y is &agr;,&bgr;-dibromopropionylamino or &agr;-bromoacryloylamino, and
Z
1
and Z
2
are each independently of the other vinyl, &bgr;-chloroethyl or &bgr;-sulfatoethyl, preferably vinyl or &bgr;-sulfatoethyl.
In the radicals of formula (6a), the fibre-reactive group —SO
2
—Z
1
is preferably in 4-position.
R
7
is preferably hydrogen.
In the radicals of formula (6b), the fibre-reactive group —CO—NH—(CH
2
)
2
—SO
2
—Z
2
is preferably in 3-position. The radical of formula (6b) preferably does not contain any sulfo group at the benzene ring.
In a particularly preferred embodiment of the novel dye mixtures, the radicals of formulae —A
1
—Y
1
and A
2
—Y
2
in the dyes of formulae (1) and (2) are each independently of the other a radical of formula (6a) or (6b), preferably, of formula (6a), which radicals have the above-cited meanings and preferred meanings.
—A
1
—Y
1
and A
2
—Y
2
in the novel dye mixtures are preferably identical.
Preferred dye mixtures are those, which comprise at least one dye of formula (1a)
together with at least one dye of formula (2a)
wherein
R
3
is hydrogen, C
1
-C
4
alkyl or C
1
-C
4
alkoxy, preferably hydrogen, methyl or methoxy, D is a radical of formula (3a) or (4a),
X
1
and X
2
are each independently of the other fluoro or chloro, and
—A
1
—Y
1
and A
2
—Y
2
are each independently of the other a radical of formula (6a) or (6b), which radicals have the above-cited meanings and preferred meanings.
In the dyes of formulae (1a) and (2a) of the novel dye mixtures, the aminotriazinyl radical of formulae
is preferably bound in 3-position to the coupling component of the azo chromophore.
In a particularly preferred embodiment of this invention, the novel dye mixtures comprise at least one dye of formula (1b)
together with at least one dye of formula (2b)
wherein
R
3
is hydrogen o

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