Bleaching and dyeing; fluid treatment and chemical modification – Reactive dye composition – process – or product – Alkylene sulfato – halotriazine – halodiazine,...
Utility Patent
1999-11-05
2001-01-02
Einsmann, Margaret (Department: 1751)
Bleaching and dyeing; fluid treatment and chemical modification
Reactive dye composition, process, or product
Alkylene sulfato, halotriazine, halodiazine,...
C008S641000, C008S918000
Utility Patent
active
06168636
ABSTRACT:
This invention relates to the technical field of fiber-reactive azo dyes.
Japanese Patent Application Publication Hei-1-170 661 discloses mixtures of yellow-dyeing monoazo dyes having a fiber-reactive group of the vinyl sulfone series, but they have certain application defects.
As with individual dyes, it is important for dye mixtures to provide dyeings having a good color yield, i.e., dyeings whose depth of shade is very high in relation to the amount of dye used, because of the coloring property of the dye mixture and because of its dyeing characteristics, such as good affinity and a high yield of fixation. In general, the color yield obtained with a mixture of two dyes will be the average of the color yields of the individual dyes. The color yield of a mixture of two dyes will therefore be lower than the color yield of the individual 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 one or more, such as two or three, preferably one or two, dyes of the hereinbelow indicated and defined general formula (1) and one or more, such as two or three, preferably one or two, dyes of the hereinbelow indicated and defined general formula (2a) or (2b) or (2a) and (2b) in a molar ratio of the dyes (1) to the dyes (2a) or (2b) or a combination of the dyes (2a) and (2b) of 70:30 to 30:70, preferably 60:40 to 40:60:
where:
M is hydrogen or an alkali metal, such as sodium, potassium or lithium;
Y
1
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, &bgr;-chloroethyl and &bgr;-sulfatoethyl, more preferably vinyl and &bgr;-sulfatoethyl;
D is a radical of benzene or of naphthalene;
R
1
is hydrogen, chlorine, 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, preferably hydrogen, methyl and methoxy and especially hydrogen;
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, preferably hydrogen, methyl and methoxy and especially hydrogen;
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, or sulfo, preferably hydrogen, methyl, methoxy and sulfo and particularly preferably sulfo, R
3
preferably being disposed para to the —NH—CO—R group;
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, preferably hydrogen, methyl, methoxy and sulfo and particularly preferably hydrogen, R
4
preferably being disposed para to the —NH—CO—R
A
group;
R
5
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, preferably hydrogen, methyl, methoxy and sulfo and particularly preferably hydrogen, R
5
preferably being disposed para to the —NH—CO—R
B
group;
R is amino or alkyl of 1 to 6 carbon atoms, preferably 1 to 3 carbon atoms, such as ethyl and especially methyl, where the alkyl may be substituted, for example by hydroxy, sulfo, carboxy, sulfato, phosphate or a —SO
2
—Y
2
group with Y
2
having one of the meanings of Y
1
, and is preferably methyl;
R
A
is amino or alkyl of 1 to 4 carbon atoms, such as methyl, or alkyl of 1 to 4 carbon atoms which is substituted by carboxy, sulfo or a —SO
2
—Y
3
group, Y
3
having one of the meanings of Y
1
, and is preferably amino;
R
B
is amino or alkyl of 1 to 4 carbon atoms, such as methyl, or alkyl of 1 to 4 carbon atoms which is substituted by carboxy, sulfo or a —SO
2
—Y
3
group, Y
3
having one of the meanings of Y
1
, and is preferably amino;
R
6
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 alkoxy, hydroxy, halogen, such as chlorine, carboxy or cyano, preferably hydrogen;
R
7
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 alkoxy, preferably hydrogen;
m is the integer 1, 2 or 3, preferably 2 or 3;
Z is a fiber-reactive radical selected from the group of the halopyrimidines, such as the difluoro- or trifluoro- or chlorofluoro- or chlorodifluoro-pyrimidines, of the dichloroquinoxalines or of the halotriazines, such as chloro- or fluoro-triazines, which are optionally substituted by an ether or amino grouping, where the radical of the halotriazine can also be bonded to a fiber-reactive group of the general formula —SO
2
—Y, Y having one of the meanings of Y
1
, which group is attached via a bridge member, for example phenylene, methyl-, ethyl-, methoxy-, ethoxy- and/or chlorine-substituted phenylene, alkylene of 1 to 6 carbon atoms or alkylene of 3 to 6 carbon atoms which is interrupted by 1 or 2 hetero groups, such as —O— and/or —NH—, or a combination of these groups to an amino group attached to the triazine radical;
Z
o
is a bivalent radical of the general formula (3)
where
Hal is chlorine or fluorine, and
W is phenylene, alkylene, phenylene-alkylene-phenylene, phenylene-alkenylene-phenylene or phenylene-phenylene or a radical of the general formula phen-G-phen, where the phenylene radicals may be substituted by 1 or 2 substituents selected from the group consisting of methoxy, ethoxy, methyl, ethyl, sulfo and carboxy, the alkylene radicals contain 1 to 6 carbon atoms, preferably 2 to 4 carbon atoms, and may be substituted by sulfo or carboxy and/or interrupted by 1 or 2 hetero groups, such at —O— and —NH—, and the alkenylene radicals are those of 2 to 4 carbon atoms, preferably vinylidene, and where phen is equal to phenylene of the above definition and G is —O—, —NH—, —CO— or —NH—CO—NH—, preferably alkylene of 1 to 6 carbon atoms, such as 1,2-ethylene and 1,3-propylene, and preferably optionally substituted phenylene, such as 1,4-phenylene, 2-sulfo-1,4-phenylene, 1,3-phenylene and 4-sulfo-1,3-phenylene.
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”, “carboxy”, “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, carboxy 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.
Hereinbelow the dyes of the general formula (1) may be referred to globally as “dyes (1)” and the dyes (2a) and (2b) as “dyes (2)”. They are generally known and extensively described in German, British and European patent application publications and also in British and U.S. patents, or can be prepared similarly to the directions provided therein.
In the dyes of the general formula (2a), Z is preferably a radical of the formula (4a), (4b), (4c) or (4d)
where
Hal is as defined above;
R
8
is hydrogen, chlorine or fluorine, preferably chlorine or fluorine;
R
18
is hydrogen or fluorine, preferably fluorine;
R
Eden Birgit
Grobel Bengt-Thomas
Krieger Karl
Rohrig Dierk
Schaffeld Mieke
Connolly Bove & Lodge & Hutz LLP
DyStar Textilfarben GmbH & Co. Deutschland KG
Einsmann Margaret
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