Deep black dye mixtures of fiber-reactive azo dyes

Details Deep black dye mixtures of fiber-reactive azo dyes Deep black dye mixtures of fiber-reactive azo dyes

2000-03-13

2002-10-15

Einsmann, Margaret (Department: 1751)

Bleaching and dyeing; fluid treatment and chemical modification

Reactive dye composition, process, or product

Alkylene sulfato, halotriazine, halodiazine,...

C008S641000, C008S924000, C008S918000

Reexamination Certificate

active

06464734

ABSTRACT:

The present invention relates to the field of fiber-reactive dyes. Black-dyeing mixtures of fiber-reactive dyes are known from U.S. Pat. No. 5,445,654 and U.S. Pat. No. 5,611,821 as well as from KR 94-2560-B1. Deep black dye mixtures are known, for example, from JP-A Sho-58-160 362 which are based on a navy-blue disazo dye and an orange monoazo dye. However, these dye mixtures have some deficiencies, in particular the washfastness to repeated washings is unfavorable.
Dyes according to the general formula (1) below are already known from, for example, U.S. Pat. No. 2,657,205, JP-A Sho-58-160 362 and U.S. Pat. No. 4,257,770 and the references cited therein.
Monoazo dyes of the general formula (2) below are already known as well, for example from DE-A 3537260, JP-A 7406798, JP-A 4950291, DE-A 2351970, DE-A 2362 683, BE-A 861220 and U.S. Pat. No. 4,283,196. However, these orange dyes generally have poor wash and chlorine fastnesses and do not build up well.
The inventors of the present invention have surprisingly found now that the washfastness and build up properties of deep black dye mixtures according to the documents mentioned above can be improved by replacing their orange components by the monoazo dyes of the general formula (2). As the washfastness properties of said deep black dye mixtures are generally limited by the washfastness of the orange. component, a skilled person would not have expected that dyes of the general formula (2) would be suitable for improving such properties in view of their disadvantages when used individually.
The present invention claims dye mixtures comprising one or more dyestuffs of the general formula (1)
and one or more dyestuffs of the general formula (2)
where
M is an alkali metal, an ammonium or the equivalent of an alkaline earth metal;
Y
1
, Y
2
and Y
3
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, (C
1
-C
4
)-alkyl, (C
1
-C
4
)-alkoxy, sulfo or chloro;
W is hydrogen, chloro, bromo, nitro, amino, acetamido, benzamido, (C
1
-C
4
)-alkyl, (C
1
-C
4
)-alkoxy, hydroxy, ureido or (C
2
-C
4
)-alkanoyl;
V is hydrogen, chloro, bromo, nitro, amino, acetamido, benzamido, (C
1
-C
4
)-alkyl, (C
1
-C
4
)-alkoxy, hydroxy, ureido or (C
2
-C
4
)-alkanoyl;
L is hydrogen, methyl, ethyl or is ethyl which is substituted in the &bgr;-position by G;
G is cyano, hydroxy, sulfo, sulfato, phosphato, acetyloxy or a residue of a lower polyethylenepolyether.
Preference is given to dye mixtures including from 60 to 95% by weight of one or more dyestuffs of the general formula (1) and from 5 to 40%by weight of one or more of a dyestuff of the general formula (2), based on the weight of the dye mixture. Special preference is given to dye mixtures including from 65 to 90% by weight of one or more dyestuffs of the general formula (1) and from 10 to 35% by weight of one or more dyestuffs of the general formula (2), based on the weight of the dye mixture.
A (C
1
-C
4
)-alkyl grouping standing for R
1
to R
6
, W or V may be straight-chain or branched and be for example methyl, ethyl, n-propyl , i-propyl, n-butyl, i-butyl, sec-butyl or tert-butyl. Preference is given to methyl and ethyl. The same logic rules for (C
1
-C
4
)-alkoxy groups, which are thus preferably methoxy and ethoxy. A (C
2
-C
5
)-alkanoyl grouping standing for W or V is preferably acetyl or propionyl. A residue of a lower polyethylenepolyether is preferably a residue of the formula CH
3
CH
2
—(OCH
2
CH
2
)
n
—O— with n=2-10.
Alkali 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, thiosulfato, phosphato, (C
2
-C
5
)-alkanoyloxy, such as acetyloxy, sulfobenzoyloxy or p-toluylsulfonyloxy and is preferably sulfato.
The groups “sulfo”, “thiosulfato”, “phosphato” and “sulfato” include both the acid form and the salt form of these groups. Accordingly, sulfo groups are groups of the formula —SO
3
M , thiosulfato groups are groups of the formula —S—SO
3
M , phosphato groups are groups of the formula —OPO
3
M
2
and sulfato groups are groups of the formula —OSO
3
M, in which M is defined as above. The groups —SO
2
Y
1
, —SO
2
Y
2
and —SO
2
Y
3
are preferably disposed para or meta relative to the diazo group, particularly preferably para. Y
1
, Y
2
and Y
3
are preferably ethenyl or &bgr;-sulfatoethyl.
R
1
is preferably hydrogen, methoxy or sulfo, R
2
is preferably hydrogen, methyl or methoxy and R
3
and R
4
are preferably hydrogen. R
5
and R
6
are preferably hydrogen, methyl, methoxy or sulfo.
W is preferably hydrogen, chloro, nitro, amino, acetamido, methyl or ureido, V is preferably hydrogen or methoxy.
L is preferably hydrogen, ethyl, &bgr;-sulfatoethyl, &bgr;-hydroxyethyl or &bgr;-cyanoethyl, G is preferably sulfato, hydroxy or cyano.
In preferred dye mixtures according to the present invention, R
1
is hydrogen, methoxy or sulfo, R
2
to R
6
are hydrogen, —SO
2
Y
1
, —SO
2
Y
2
and —SO
2
Y
3
are disposed para relative to the diazo group, Y
1
, Y
2
and Y
3
are &bgr;-sulfatoethyl and W, V, L and G have one of the preferred meanings given above.
The dye mixtures of the present invention may optionally contain one or more dyestuffs of the general formulae (3a) or (3b) or both
in which R
1
, R
2
, R
3
, R
4
, M, Y
1
and Y
2
are defined as above. These two dyestuffs may already be formed during the synthesis of the dyestuff of the general formula (1) if coupling reactions of the starting compounds are incomplete.
If the dye mixture of the present invention contains, as a further component, a dyestuff of formula (3a) or of formula (3b) or both, the dyestuff or dyestuffs of formula (3a) or of formula (3b) or of both are present in the dye mixture of the dyestuffs of the general formulae (1) and (2) in the range of 0.01 to 8% by weight, calculated on the 100% dye mixture of the dyestuffs of the general formulae (1) and (2).
The dye mixtures of the present invention may in addition contain further dyestuffs which act as so-called shading components. Such shading components are in particular red or yellow to golden orange dyestuffs. They may be contained in a ratio of up to 25% by weight of the total mixtures. Preferably, they are contained in amounts of 0.5 to 20% by weight, particularly preferably in amounts of 1 to 10% by weight, based on the weight of the dye mixture. These shading components are generally used to give the dyeings a more or less reddish or greenish shade and are also added to enhance the shade reproducibility of production batches. Preference is given to dyestuffs of the general formulae (4) to (10)
where
M is defined as given above;
Y
4
t Y
12
independently have one of the meanings of Y
1
;
R
7
to R
18
and R
22
and R
23
independently have one of the meanings of R
1
; R
19
to R
21
are independently (C
1
-C
4
)-alkyl, —COOH or —COOR
24,
 where
R
24
is (C
1
-C
4
)-alkyl; and
P to P
2
are independently hydroxy, (C
1
-C
4
)-alkoxy, amino, (C
1
-C
4
)-alkylamino or di-(C
1
-C
4
)-alkylamino .
Especially preferred shading components are the dyestuffs of the formulae (4a), (5a), (6a), (7a), (7b) and (8a)
wherein M is defined as given above.
The dyestuffs of the general formulae (4) to (10) are known. The dyestuffs of the general formula (4) are described in DEA 4329421, the dyestuffs of the general formula (5) in JP-A 69-14107, the dyestuffs of the general formula (6) in DE-A 3134357, the dyestuffs of the general formula (7b) in DE-A 1911427, the dyestuffs of the general formula (8) in EP-A 489360, the dyestuffs of the general formula (9) in DE-A 1911427 and the dyestuffs of the general formula (10) in DEA 1215282.
The dyestuffs of the general formulae (1) to (10), in particular if those corresponding to the same general formula have the same chromophore, can have, within the meaning of their Y-moiety, structurally different fiber-reactive groups correspo

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