Bleaching and dyeing; fluid treatment and chemical modification – Reactive dye composition – process – or product – Alkylene sulfato – halotriazine – halodiazine,...
Reexamination Certificate
1999-07-19
2001-02-06
Einsmann, Margaret (Department: 1751)
Bleaching and dyeing; fluid treatment and chemical modification
Reactive dye composition, process, or product
Alkylene sulfato, halotriazine, halodiazine,...
C008S641000, C008S918000, C008S924000
Reexamination Certificate
active
06183522
ABSTRACT:
Dye mixtures comprising water-soluble fiber-reactive azo dyes, preparation thereof and use thereof
This invention relates to the technical field of fiber-reactive azo dyes.
U.S. Pat. Nos. 4988803, 5097021, 5342927, 5541300 and 5548072 disclose monoazo dyes containing a fiber-reactive radical of the amino-substituted halotriazinylamino series with or without a further fiber-reactive radical of the vinyl sulfone or fluoropyrimidinyl series. However, the dyes described therein have certain application defects, for example an excessive dependence of the color yield on changing dyeing parameters in the dyeing process, an insufficient solubility in the aqueous dyebath at higher dyeconcentrations in the presence of electrolyte salts or an insufficient color build-up on cotton and especially viscose (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 a 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. The color yield of a mixture of, for example, two dyes will therefore be lower than the color yield of that dye having the larger color yield property.
The present invention, then, provides dye mixtures which provide dyeings having a color yield which is surprisingly distinctly higher than the average of the color yields of the dyeings of the individual dyes in the dye 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.
The invention accordingly provides dye mixtures comprising at least 2, such as 3 or 4, preferably 3 and particularly preferably 2, dyes selected from the group of the dyes of the general formulae (1), (2) and (3), where at least one of the dyes conforms to the general formula (1):
where:
M is hydrogen or an alkali metal, such as sodium, potassium or lithium;
D
1
is a benzene or naphthalene radical;
D
2
is a benzene or naphthalene radical;
Y is vinyl or is ethyl which is substituted in the &bgr;-position by an alkali-eliminable substituent, for example by chlorine, sulfato, thiosulfato, phosphate, alkanoyloxy of 2 to 5 carbon atoms, such as acetyloxy, and sulfobenzoyloxy, and is preferably vinyl or &bgr;-sulfatoethyl;
R
1
is hydrogen, alkyl of 1 to 4 carbon atoms, such as ethyl and especially methyl, or alkoxy of 1 to 4 carbon atoms, such as ethoxy and especially methoxy, when D
1
is a benzene radical, preferably hydrogen, methyl and methoxy, especially hydrogen, or is hydrogen or sulfo, preferably hydrogen, when D
1
is a naphthalene radical;
R
2
is hydrogen, alkyl of 1 to 4 carbon atoms, such as ethyl and especially methyl, or alkoxy of 1 to 4 carbon atoms, such as ethoxy and especially methoxy, when D
1
is a benzene radical, preferably hydrogen, methyl and methoxy, especially hydrogen, or is hydrogen or sulfo, preferably sulfo, when D
1
is a naphthalene radical;
R
3
is hydrogen, alkyl of 1 to 4 carbon atoms, such as ethyl and especially methyl, alkoxy of 1 to 4 carbon atoms, such as ethoxy and especially methoxy, carboxyl or sulfo, when D
2
is a benzene radical, preferably hydrogen, methyl and methoxy, or is hydrogen or sulfo, preferably hydrogen, when D
2
is a naphthalene radical;
R
4
is hydrogen, alkyl of 1 to 4 carbon atoms, such as ethyl and especially methyl, alkoxy of 1 to 4 carbon atoms, such as ethoxy and especially methoxy, or sulfo, when D
2
is a benzene radical, preferably hydrogen, methyl, methoxy or sulfo, especially hydrogen or sulfo, or is hydrogen or sulfo, preferably sulfo, when D
2
is a naphthalene radical;
R
5
is hydrogen, chlorine, bromine or sulfo when D
2
is a benzene radical, preferably hydrogen, or is hydrogen or sulfo when D
2
is a naphthalene radical;
X
1
is fluorine, bromine or chlorine, preferably chlorine and especially fluorine;
X
2
is fluorine, bromine or chlorine, preferably chlorine and especially fluorine;
Z
1
is a group of the general formula (4a) or (4b) and preferably a group of the general formula (4a)
where
R
A
is hydrogen or alkyl of 1 to 4 carbon atoms, such as methyl and especially ethyl, which may be substituted, for example by sulfo, carboxyl, methoxy, ethoxy, sulfato, phosphate, acetoxy or propionyloxy, preferably by hydroxyl, and is preferably hydrogen or &bgr;-hydroxyethyl,
R
B
is hydrogen or alkyl of 1 to 4 carbon atoms, such as methyl and especially ethyl, which may be substituted, for example by sulfo, carboxyl, methoxy, ethoxy, sulfato, phosphate, acetoxy or propionyloxy, preferably by hydroxyl, and is preferably hydrogen or &bgr;-hydroxyethyl, or
the group —NR
A
R
B
forms the radical of a 5- to 7-membered saturated heterocycle wherein the alkylene radical of this heterocycle may be additionally interrupted by 1 or 2, preferably 1, hetero groups, such as —O— and —NH—, and is preferably piperidino, piperazino and especially morpholino,
R
C
is hydrogen or alkyl of 1 to 4 carbon atoms, such as methyl or ethyl, or alkyl of 1 to 4 carbon atoms, such as methyl and especially ethyl, which may be substituted, for example by sulfo, carboxyl, sulfato or especially hydroxyl, and is preferably hydrogen or &bgr;-hydroxyethyl, and
R
D
is hydrogen or phenyl, which may be substituted by 1 or 2 substituents selected from the group consisting of alkyl of 1 to 4 carbon atoms, such as ethyl and especially methyl, alkoxy of 1 to 4 carbon atoms, such as ethoxy and especially methoxy, carboxyl, sulfo and chlorine, and is preferably phenyl which is substituted by a substituent selected from the group consisting of sulfo and chlorine;
Z
2
has one of the meanings mentioned for Z
1
and is preferably a group of the general formula (4b);
X
3
is fluorine, bromine or chlorine, preferably chlorine or especially fluorine;
Z
3
has one of the meanings mentioned for Z
1
and is preferably a group of the general formula (4a);
Z
0
is a group of the general formula (5a), (5b), (5c) or (5d)
where
R
10
is hydrogen or chlorine;
R
11
is hydrogen, chlorine or fluorine;
R
0
is hydrogen, alkyl of 1 to 4 carbon atoms, such as ethyl and especially methyl, phenyl or chlorine-, sulfo-, methyl-, ethyl-, methoxy-, ethoxy- or carboxyl-substituted phenyl;
X
4
has one of the meanings of X
1
;
Y
1
has one of the meanings of Y;
B is alkylene of 2 to 6 carbon atoms, such as n-ethylene and n-propylene, or is alkylenephenylene or phenylenealkylene each containing an alkylene of 2 to 4 carbon atoms, such as n-ethylene or n-propylene, wherein the phenyl radicals may be additionally substituted by 1 or 2 substituents selected from the group consisting of methyl, methoxy, ethyl and ethoxy, or is alkylene of 3 to 8 carbon atoms which is interrupted by 1 or 2 hetero groups, such as —O— and —NH—, for example a —(CH
2
)
2
—O—(CH
2
)-group;
the one —SO
3
M group in the sulfoaminonaphthol radicals of the formulae (1), (2), (3) is attached to the naphthalene radical in a position which is meta or para, preferably meta, relative to the NH group;
the azo group in the formula (3) is attached to the benzene nucleus in a position which is meta or para, preferably meta, relative to the Z
0
—NH-group, wherein the —SO
3
M group there is preferably attached to the benzene nucleus in a position which is ortho relative to the azo group.
In the above general formulae and also in the subsequent general formulae, the individual constituents of the formulae, whether they bear identical or different designations, can have
Grobel Bengt-Thomas
Russ Werner
Schumacher Christian
Connolly Bove & Lodge & Hutz LLP
Dystar Textilfarben GmbH & Co.
Einsmann Margaret
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