Bleaching and dyeing; fluid treatment and chemical modification – Reactive dye composition – process – or product – Alkylene sulfato – halotriazine – halodiazine,...
Reexamination Certificate
2000-04-06
2002-03-19
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
06358287
ABSTRACT:
The present invention relates to the technical field of fiber-reactive dyes. To obtain green reactive dyeings, it is necessary to use either green reactive phthalocyanine dyes or mixtures of blue with yellow reactive dyes. Mixtures of yellow reactive dyes with navy azo dyes are relatively dull and have poor lightfastnesses. Mixtures of yellow reactive dyes with reactive phthalocyanines are brilliant, but have poor washfastnesses. In addition, mixtures with yellow reactive dyes are frequently photochromic.
Unfortunately, it is especially the strong, brilliant reactive triphendioxazine dyes which are difficult to combine with other dyes because of pronounced blocking effects. This problem is described in U.S. Pat. No. 5,484,459.
It is an object of the present invention to provide mixtures of yellow reactive dyes with triphendioxazines in the green hue region without the abovementioned disadvantages.
It has now been found that, surprisingly, mixtures comprising the dyes of the general formulae (1) and (2) lead to excellent results.
The present invention accordingly provides dye mixtures comprising one or more dyes of the general formula (1)
and one or more dyes of the general formula (2)
where:
R
1
is hydrogen or chlorine, preferably chlorine;
R
2
is hydrogen or chlorine, preferably chlorine;
Z
1
is OM or vinyl or is ethyl that is substituted in the Deposition by an alkali-eliminable substituent, as for example by chlorine, sulfato, thiosulfato, phosphate, alkanoyloxy of 2 to 5 carbon atoms, such as acetyloxy, or sulfobenzoyloxy, and is preferably vinyl, &bgr;-chloroethyl or &bgr;-sulfatoethyl, particularly preferably vinyl or &bgr;-sulfatoethyl;
Z
2
is OM, hydroxyethyl, vinyl or is ethyl that is substituted in the &bgr;-position by an alkali-eliminable substituent, as for example by chlorine, sulfato, thiosulfato, phosphate, alkanoyloxy of 2 to 5 carbon atoms, such as acetyloxy, or sulfobenzoyloxy, and is preferably vinyl, &bgr;-chloroethyl or &bgr;-sulfatoethyl, particularly preferably vinyl or &bgr;-sulfatoethyl;
Z
3
is vinyl or is ethyl that is substituted in the &bgr;-position by an alkali-eliminable substituent, as for example by chlorine, sulfato, thiosulfato, phosphate, alkanoyloxy of 2 to 5 carbon atoms, such as acetyloxy, or sulfobenzoyloxy, and is preferably vinyl, &bgr;-chloroethyl or &bgr;-sulfatoethyl, particularly preferably vinyl or &bgr;-sulfatoethyl;
Z
4
is hydroxyethyl, vinyl or is ethyl that is substituted in the &bgr;-position by an alkali-eliminable substituent, as for example by chlorine, sulfato, thiosulfato, phosphate, alkanoyloxy of 2 to 5 carbon atoms, such as acetyloxy, or sulfobenzoyloxy, and is preferably vinyl, &bgr;-chloroethyl or &bgr;-sulfatoethyl, particularly preferably vinyl or &bgr;-sulfatoethyl;
Y is a straight-chain or branched alkylene radical of 2 to 6 carbon atoms which may be interrupted by 1 or 2 hetero groups from the group consisting of —NH—, —O— and —SO
2
—;
X is W or —NR*CO—V—COOM and if Z
1
and Z
2
=OM is a radical of the formula (1a)
where
Hal is chlorine or fluorine;
r is 1 or 2;
R
A
is hydrogen, alkyl of 1 to 4 carbon atoms, such as ethyl or especially methyl, hydroxyethyl or sulfoethyl;
R
B
is hydrogen, methoxy, ethoxy, methyl or ethyl;
W is sulfato, sulfo or carboxyl;
R* is hydrogen or an alkyl group of 1 to 4 carbon atoms;
V is —(CH2)n where n=1 to 4;
R
3
is hydrogen, alkyl of 1 to 4 carbon atoms, such as ethyl or especially methyl, alkoxy of 1 to 4 carbon atoms, such as ethoxy or especially methoxy, sulfo or carboxyl, preferably hydrogen, methyl or methoxy, particularly preferably hydrogen;
R
4
is hydrogen, alkyl of 1 to 4 carbon atoms, such as ethyl or especially methyl, alkoxy of 1 to 4 carbon atoms, such as ethoxy or especially methoxy, sulfo or carboxyl, preferably hydrogen, methyl or methoxy, particularly preferably hydrogen;
B is a direct bond or alkylene of 1-3 carbon atoms;
M is hydrogen, an alkali metal, such as sodium, potassium or lithium, or the equivalent of an alkaline earth metal, as of calcium, preferably hydrogen or especially sodium, potassium or lithium.
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 meanings under their definition which are mutually identical or different.
The terms “sulfo”, “thiosulfato”, “carboxyl”, “phosphate” and “sulfato” cover not only the acid form but also the salt form of the respective groups. Accordingly, sulfo groups are groups conforming to the general formula —SO
3
M, thiosulfato groups are groups conforming to the general formula —S—SO
3
M, carboxyl groups are groups conforming to the general formula —COOM, phosphato groups are groups conforming to the general formula —OPO
3
M
2
and sulfato groups are groups conforming to the general formula —OSO
3
M, where each M is as defined above. Groups of the general formulae (3a) and (3b)
present in the dyes (2) are for example 3-(&bgr;-sulfatoethylsulfonyl)-phenyl, 4-(&bgr;-sulfatoethylsulfonyl)-phenyl, 2-methyl-5-(&bgr;-sulfatoethylsulfonyl)-phenyl, 2-methoxy-5-(&bgr;-sulfatoethyl-sulfonyl)-phenyl, 4-methyl-3-(&bgr;-sulfatoethylsulfonyl)-phenyl, 2,5-dimethyl-4-(&bgr;-sulfatoethylsulfonyl)-phenyl, 2,6-dimethyl-4-(&bgr;-sulfatoethylsulfonyl)-phenyl, 2-methoxy-4-(&bgr;-sulfatoethylsulfonyl)-phenyl, 4-methoxy-5-(&bgr;-sulfatoethylsulfonyl)-phenyl, 2-methoxy-5-methyl4-(&bgr;-sulfatoethylsulfonyl)-phenyl, 2,4-dimethoxy-5-(&bgr;-sulfatoethylsulfonyl)-phenyl, 2,5-dimethoxy4-(&bgr;-sulfatoethylsulfonyl)-phenyl, 2-carboxy-5-(&bgr;-sulfatoethylsulfonyl)-phenyl, 2-sulfo-5-(&bgr;-sulfatoethylsulfonyl)-phenyl and 2-sulfo4-(&bgr;-sulfatoethyl-sulfonyl)-phenyl, of which in particular 3- or 4-(&bgr;-sulfatoethylsulfonyl)-phenyl, and also their derivatives in which the &bgr;-sulfatoethylsulfonyl group is replaced by a vinylsulfonyl or &bgr;-thiosulfatoethylsulfonyl or &bgr;-chloroethylsulfonyl group. The groups Z
3
—SO
2
— and Z
4
—SO
2
are preferably disposed meta or para relative to the pyrazole radical
Of the dye mixtures of the invention, preference is given to those with dyes (1) where R
1
and R
2
are each chlorine, Y is ethyl, W is sulfato, NHCOCH
2
CH
2
COOH, and Z
1
and Z
2
are each &bgr;-sulfatoethyl.
Of the dye mixtures of the invention, preference is likewise given to those with dyes (2) where B is a direct bond, SO
2
—Z
3
or SO
2
—Z
4
is 4-(&bgr;-sulfatoethylsulfonyl) and the sulfo group is disposed ortho or meta relative to the diazo group. The dyes of the general formula (1) may, especially if the chromophore is the same, possess different fiber-reactive groups —SO
2
—Z
1
and —SO
2
—Z
4
(the same applies to the dyes of the general formula (2) with regard to —SO
2
—Z
3
and —SO
2
—Z
4
). More particularly, the dye mixtures may include dyes of the same choromphore conforming to the discussed general formulae where the fiber-reactive groups —SO
2
—Z
1
, —SO
2
—Z
2
, —SO
2
—Z
3
and —SO
2
—Z
4
are, on the one hand, vinylsulfonyl groups and, on the other, &bgr;-chloroethylsulfonyl or &bgr;-thiosulfatoethylsulfonyl or preferably &bgr;-sulfatoethylsulfonyl groups.
In dye mixtures according to the invention, the ratios of the dye or dyes (1) and the dye or dyes (2) are preferably 98:2 to 10:90% by weight, particularly preferably 70:30% by weight to 30:70% by weight, most preferably 60:40 to 40:60% by weight. Dye mixtures according to the invention can be prepared by mixing the individual dyes.
Hereinbelow the dyes of the general formula (1) may be referred to globally as “dyes (1)” and the dyes (2) as “dyes (2)”. They are known from DE-A 1215282, EP-A 0153599 and EP-B 258493 and can be prepared similarly to the directions provided therein.
Blocking effects are determined by using a mixture according to the invention to dye the material to be dyed. In further identical dyeing processes, one or more dyes of the general formula (1) according to the invention are applied first and this dyed material is then overdyed with one or more dyes of the general formula (2) a
Ehrenberg Stefan
Schumacher Christian
Connolly Bove Lodge & Hultz LLP
DyStar Textilfarben GmbH & Co.
Einsmann Margaret
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