Bleaching and dyeing; fluid treatment and chemical modification – Reactive dye composition – process – or product – Alkylene sulfato – halotriazine – halodiazine,...
Reexamination Certificate
1999-09-29
2001-05-08
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
06228131
ABSTRACT:
DESCRIPTION
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.
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 1 or 2, dyes selected from the group of the dyes of the hereinbelow indicated and defined general formula (1) and one or more, such as two or three, preferably 1 or 2, dyes selected from the group of the dyes of the hereinbelow indicated and defined general formula (2) in a molar ratio of the dye or dyes (
1
) to the dye or dyes (
2
) of 75:25 to 25:75, preferably 65:35 to 35:65, more preferably 60:40 to 40:60.
In these formulae:
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 or &bgr;-sulfatoethyl, more preferably vinyl or &bgr;-sulfatoethyl;
Y
2
has one of the meanings of Y
1
;
R
1
is hydrogen, chlorine, 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, carboxyl or sulfo, preferably hydrogen, methyl or methoxy, especially hydrogen;
R
2
is hydrogen, alkyl of 1 to 4 carbon atoms, such as ethyl or especially methyl, or alkoxy of 1 to 4 carbon atoms, such as ethoxy or especially methoxy, preferably hydrogen, methyl or methoxy, especially hydrogen;
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, or sulfo, preferably hydrogen, methyl or methoxy or especially sulfo, and R
3
is preferably disposed para to the —NH—CO—R group;
R is amino or alkyl of 1 to 6 carbon atoms, preferably of 1 to 3 carbon atoms, such as ethyl or especially methyl, where alkyl may be substituted, for example by hydroxyl, sulfo, carboxyl, sulfato, phosphato or a —SO
2
—Y
3
group, where Y
3
has one of the meanings of Y
1
;
R
4
is hydrogen, chlorine, 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, or sulfo, preferably hydrogen, methyl or methoxy, especially hydrogen;
R
5
is hydrogen, alkyl of 1 to 4 carbon atoms, such as ethyl or especially methyl, or alkoxy of 1 to 4 carbon atoms, such as ethoxy or especially methoxy, preferably hydrogen, methyl or methoxy, especially hydrogen;
R
6
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, or sulfo and preferably is hydrogen, methyl, methoxy or sulfo, particularly preferably hydrogen;
n is zero or 1;
R
7
is methyl or carboxyl;
R
8
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, or chlorine, preferably methyl or chlorine, particularly preferably hydrogen;
R
9
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, or chlorine and preferably is hydrogen;
m is zero, 1 or 2, preferably 1 or 2, particularly preferably 1 (when m is zero, this group is hydrogen);
the Y
1
—SO
2
— and Y
2
—SO
2
— groups are attached to the benzene nucleus in a position which is preferably meta and particularly preferably para to the azo group and to the —NH—CO— group, respectively;
the —NH—CO— group is attached to the benzene nucleus in the formula (2) in a position which is meta and preferably para 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 meanings under their definition which are mutually identical or different.
The terms “sulfo”, “thiosulfato”, “carboxyl”, “phosphato” 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.
The dyes of the general formulae (1) and (2) are generally known and described for example in European Patent Application Publication No. 0 073 481, British Patent No. 1 124 388 and German Patents Nos. 1 282 213 and 1 206 107.
Of the dyes of the general formula (1) present in the dye mixture of the invention, those must be emphasized in particular where the Y
1
—SO
2
— group is meta and particularly preferably para to the azo group, Y
1
is vinyl or preferably &bgr;-sulfatoethyl, R
1
and R
2
are independently hydrogen, methyl or methoxy, preferably hydrogen, R
3
is sulfo and attached to the benzene nucleus para to the —NH—CO—R group, and R is methyl.
Of the dyes of the general formula (2) present in the dye mixture of the invention, preference is given to those where n is zero, the Y
2
—SO
2
— group is meta or para to the azo group, R
4
is hydrogen, methyl or methoxy, R
5
is hydrogen or methyl, R
8
and R
9
are both hydrogen and m is 1, this sulfo group preferably being attached to the benzene nucleus in a position which is para to the nitrogen atom of the pyrazolone ring; of these preference is in turn given to those monoazo dyes of the general formula (2) where R
4
and R
5
are both hydrogen and the Y
2
—SO
2
— group is para to the azo group.
Furthermore, of the monoazo dyes of the general formula (2) in the mixture of the invention, particular interest pertains to those where n is 1, R
4
and R
5
are both hydrogen, the Y
2
—SO
2
— group is meta or preferably para to the —NH—CO— group and Y
2
is vinyl or &bgr;-sulfatoethyl, preferably &bgr;-sulfatoethyl, the —NH—CO— group is meta or preferably para to the azo group, R
6
is hydrogen, R
8
and R
9
are both hydrogen and m is 1 and this sulfo group is preferably attached to the benzene nucleus in a position which is para to the nitrogen atom of the pyrazolone ring. p The dyes of the general formula (1) may possess different fiber-reactive —SO
2
—Y
1
groups within the meaning of Y
1
, especially if they have the same chromophore (the same applies to the dyes of the general formula (2) with regard to Y
2
and Y
3
). More particularly, the dye mixtures may contain dyes of the same chromophore which conform to the general formula (1) and/or dyes of the same chromophore which co
Grobel Bengt-Thomas
Krieger Karl
Lippert Gerhard
Rohrig Dierk
Schaffeld Mieke
Connolly Bove & Lodge & Hutz LLP
DyStar Textilfarben GmbH & Co. Deutschland KG
Einsmann Margaret
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