Dye mixture comprising water-soluble fiber-reactive dyes,...

Details Dye mixture comprising water-soluble fiber-reactive dyes,... Dye mixture comprising water-soluble fiber-reactive dyes,...

2000-02-23

2002-05-21

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

06391066

ABSTRACT:

This invention relates to the technical field of fiber-reactive azo dyes.
Dyes conforming to the hereinbelow indicated general formulae 1 and 2 are known from EP-A 94055, EP-A 144766 and EP-A 775732. However, these dyes have certain application defects, for example an excessive dependence of the color yield on changing dyeing parameters in the dyeing process, or an insufficient or unlevel color build-up on cotton (good color build-up follows from the ability of a dye to produce a correspondingly stronger dyeing from an increased dye concentration in the dyebath). Possible consequences of these shortcomings are poor reproducibilities for the dyeings which are obtainable.
However, it is particularly important to obtain dyeings having a good color yield, i.e., dyeings whose depth of shade is very high in relation to the amount of dye used, for example in comparison with other dyes, because of the coloring property of the dye itself (high absorbance) and because of the dyeing characteristics of this dye, such as good affinity and high yield of fixation. If mixtures of dyes having a certain color yield are used, the color yield of this mixture of dyes will generally be the average of the color yields of the individual dyes, which is why the color yield of a mixture of, for example, two dyes will be less than the color yield obtained when the dye having the larger color yield property is used as the only dye but in the total amount of the two individual dyes.
It has now been found that the color strength of the hereinbelow described dye mixtures according to the invention is surprisingly higher than the sum total of the color strengths afforded by the individual dyes in the mixture. This synergistic effect also shows itself in improved build-up characteristics on the part of the mixture of the invention compared with the individual dyes in the mixture.
It is true that synergistic mixtures of certain reactor dyes are already known from EP-A 681002, but the mixtures described therein have certain application defects, for example an unlevel build-up in the cold pad-batch process, and also the staining of adjacent fabric, especially polyester, in continuous dyeing by the pad-steam process. This staining is undesirable because it means that, in commercial practice, the dyed material has to be subjected to several energy- and media-intensive (water) cleaning operations to remove the stains. The present invention also provides a way of reducing this staining while improving the build-up characteristics of the mixture according to the invention compared with the individual dyes in the mixture.
The present invention accordingly provides dye mixtures comprising one or more azo dyes of the general formula (1) and one or more azo dyes of the general formula (2)
where
M is an alkali metal, an ammonium or the equivalent of an alkaline earth metal;
X, X
1
and X
2
are independently fluoro, chloro, alkoxy, hydroxyl, cyanamido, amino, anilino, sulfoanilino or alkylamino;
Y, Y
1
and Y
2
are independently ethenyl or a grouping of the formula —CH
2
CH
2
Z, where
Z is an alkali-eliminable grouping;
R
1
, R
2
, R
3
, R
4
, R
5
and R
6
are independently hydrogen, alkyl, alkoxy, sulfo, hydroxyl, cyano, chloro or bromo;
B is an alkylenediamino bridge of the general formula D or E or F
where n, m and o are independently from 1 to 4;
A and G combine with the joining nitrogen atom to form a morpholine or piperazine radical; or
A is hydrogen, (C
1
-C
4
)-alkyl, which may be substituted, phenyl or phenyl substituted by alkyl, alkoxy, sulfo, hydroxyl, cyano, chloro or bromo; and
G has one of the meanings of A or is a fiber-reactive radical of the general formula H, I or J
t where p, q and r are independently from 1 to 4;
Y
3
, Y
4
and Y
5
independently have one of the meanings of Y
1
; and
R
7
and R8 are independently hydrogen, alkyl, alkoxy, sulfo, hydroxyl, cyano, chloro or bromo.
Alkyl R and any alkyl substituent on phenyl A may be straight-chain or branched and be for example methyl, ethyl, n-propyl , i-propyl, n-butyl, i-butyl, sec-butyl, tert-butyl, pentyl or hexyl. Preference is given to (C
1
-C
4
)-alkyl groups, and methyl and ethyl are particularly preferred. Similarly, (C
1
-C
4
)-alkyl A is preferably methyl or ethyl.
The same logic rules for alkoxy groups, which are thus preferably (C
1
-C
4
)-alkoxy groups and particularly preferably methoxy and ethoxy, and also for alkylamine X. The latter is preferably (C
1
-C
4
)-alkylamine and particularly preferably methylamine or ethylamine.
Alkyl metal M is preferably sodium, potassium or lithium, particularly preferably sodium. The equivalent of an alkaline earth metal M is preferably the equivalent of calcium.
An alkali-eliminable grouping Z is, for example, chloro, acetyl, phosphato or preferably sulfato.
M is preferably sodium, i.e., the dyes in dye mixtures according to the invention are preferably in the form of their sodium salts. The X radicals are each preferably independently chloro or fluoro, and the Y radicals are each preferably ethenyl or &bgr;-sulfatoethyl. The groups —SO
2
Y, —SO
2
Y
1
and —SO
2
Y
2
are preferably disposed para relative to the diazo group. The —SO
2
Y
5
group is preferably disposed para or meta relative to the amino group. R
1
to R
8
are each preferably independently hydroxyl, methyl, methoxy, sulfo and particularly preferably hydrogen. Most preferably R
1
to R
8
are all hydrogen. n, m, p, q and r are each preferably 2 or 3. B is for example 1,3- to 1,6-(C
3
-C
6
)-alkylenediamino, 1,5-diamino-3-oxapentane, and is particularly preferably N-(2-hydroxyethyl)-ethylenediamino. A is preferably hydrogen, methyl or phenyl, while G is preferably 3-sulfophenyl, 3-(&bgr;-sulfatoethylsulfonyl)-phenyl or 3-(&bgr;-sulfatoethylsulfonyl)-propyl. Particularly preferably G is 2-(&bgr;-sulfatoethylsulfonyl)-ethyl or 4-(&bgr;-sulfatoethylsulfonyl)-phenyl.
In particularly preferred dye mixtures according to the invention, R
1
to R
8
are each hydrogen, the groups —SO
2
Y, —SO
2
Y
1
and —SO
2
Y
2
are disposed para relative to the diazo group and Y, Y
1
and Y
2
are each ethenyl or &bgr;-sulfatoethyl, A is hydrogen, methyl or phenyl, X, X
1
and X
2
are each fluoro or chloro, and G is 2-(&bgr;-sulfatoethyl-sulfonyl)-ethyl, 4-(&bgr;-sulfatoethylsulfonyl)-phenyl or is a radical of the general formula I with q=r=2.
In general, the azo dye of the general formula (1) and the azo dye of the general formula (2) are present in the dye mixture of the invention in a blend ratio of 90:10% by weight to 10:90% by weight, preferably in a ratio of 70:30% by weight to 30:70% by weight. Particularly preferably they are present in the mixture in a ratio of 65:35 to 35:65% by weight.
The dye mixtures of the invention can be present as a preparation in solid or in liquid (dissolved) form. In solid form, they generally include the electrolyte salts customary for water-soluble and especially for fiber-reactive dyes, such as sodium chloride, potassium chloride and sodium sulfate, and may further include the auxiliaries customary in commercial dyes, such as buffer substances capable of setting a pH in aqueous solution between 3 and 7, such as sodium acetate, sodium borate, sodium bicarbonate, sodium dihydrogenphosphate, sodium tricitrate and disodium hydrogen phosphate, or small amounts of siccatives; if they are present in a liquid, aqueous solution (including the presence of thickeners of the type customary in print pastes), they may also include substances which ensure a long life for these preparations, for example mold preventatives.
In general, the dye mixtures of the invention are present as dye powders containing 10 to 80% by weight, based on the dye powder or the preparation, of an electrolyte salt which is also referred to as a standardizing agent. These dye powders may additionally include the aforementioned buffer substances in a total amount of up to 10% by weight, based on the dye powder. If the dye mixtures of the invention are present in aqueous solution, the total dye content of these aqueous solutions will be up to ab

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