Bleaching and dyeing; fluid treatment and chemical modification – Reactive dye composition – process – or product – Alkylene sulfato – halotriazine – halodiazine,...
Reexamination Certificate
2000-01-27
2001-11-20
Einsmann, Margaret (Department: 1751)
Bleaching and dyeing; fluid treatment and chemical modification
Reactive dye composition, process, or product
Alkylene sulfato, halotriazine, halodiazine,...
C008S641000, C008S918000
Reexamination Certificate
active
06319291
ABSTRACT:
The present invention relates to the field of fiber-reactive dyes. It describes navy-blue dye mixtures of fiber-reactive azo dyes and use thereof for dyeing hydroxy- and/or carboxamido-containing fiber material.
The present invention provides a dye mixture comprising one or more disazo dyes conforming to the formula (1) and one or more monoazo dyes conforming to the formula (2)
wherein
R
1
, R
2
, R
3
and R
4
, identical to or different from each other, are each hydrogen, methyl, ethyl, methoxy, ethoxy, sulfo or carboxy,
R
5
, R
6
, R
7
and R
8
, identical to or different from each other, are each hydrogen, methyl, ethyl, methoxy or ethoxy,
Y is in each instance independently of the others vinyl, &bgr;-chloroethyl, &bgr;-thiosulfatoethyl or &bgr;-sulfatoethyl,
a is the number 0 or 1,
b is the number 0 or 1,
M is hydrogen or an alkali metal,
Z
1
and Z
2
are independently selected from the fiber-reactive groups of the formulae (3a), (3b), (3c), (3d) and (3e).
where Q is chloro, cyanamido, hydroxy, alkoxy of 1 to 4 carbon atoms, phenoxy, sulfophenoxy, pyridino, carboxypyridino, carbamoylpyridino or a group of the general formulae (4a) or (4b),
wherein
R
9
is hydrogen, alkyl of 1 to 4 carbon atoms, cyclohexyl, alkoxy of 1 to 4 carbon atoms, hydroxyalkyl of 2 to 4 carbon atoms, sulfoalkyl of 1 to 4 carbon atoms, phenyl unsubstituted or substituted by 1 to 2 substituents selected from the group of substituents consisting of chlorine, bromine, methyl, ethyl, methoxy, sulfo and carboxy, or is monosulfonaphthyl, disulfonaphthyl, alkyl of 2 to 6 carbon atoms substituted by phenyl, the alkyl moiety may be interrupted by a hetero group selected from O, S, NH, SO
2
, CO, CO—NH or NH—CO, and the phenyl substituent thereof may be substituted by 1 to 2 substituents selected from the group consisting of chlorine, bromine, methyl, ethyl, methoxy, sulfo, and carboxy,
R
10
has one of the meanings given for R
9
,
W is arylene, alkylene or alkylene-arylene, each unsubstituted or substituted, wherein the alkylene moieties being preferably those of 1 to 6 carbon atoms, preferably of 1 to 4 carbon atoms, in particular of 1 to 3 carbon atoms, such as methylene, ethylene and n-propylene, or being preferably of 2 to 6 carbon atoms, if interrupted by a hetero group, such as O, S, NH, SO
2
, CO, CO—NH, NH—CO, arylene being preferably phenylene or naphthylene, the substituents of phenylene being preferably 1 or 2 substituents selected from the group consisting of alkyl of 1 to 4 carbon atoms, such as methyl and ethyl, alkoxy of 1 to 4 carbon atoms, such as methoxy and ethoxy, carboxy, sulfo and chlorine, in particular thereof methyl, ethyl, methoxy and ethoxy, and the substituents of naphthylene being preferably 1 or 2 sulfo groups,
Y is defined above and,
n is the number 1 or 2.
Preference is given to dye mixtures comprising an amount of from 50% to 95% by weight in respect of the disazo dyes(s) of the formula (1) and of from 5% to 50% by weight in respect of the dye(s) of the formula (2).
Special preference is given to dye mixtures comprising an amount of from 60% to 80% by weight in respect of the disazo dyes(s) of the formula (1) and of from 20% to 40% by weight in respect of the dye(s) of the formula (2).
A sulfo group is a group of the formula —SO
3
M, a sulfato group is a group of the formula —OSO
3
M, and a thiosulfato group is a group of formula —S—SO
3
M.
R
1
and R
3
are each independently of one another preferably hydrogen or methoxy and in particular hydrogen. R
2
and R
4
are preferably hydrogen. It is especially preferred if R
1
, R
2
, R
3
and R
4
are each hydrogen.
M is preferably hydrogen, lithium, sodium or potassium.
The dyes of the formula (1), and also the dyes of formula (2), in particular if they have the same chromophore, can have, within the meaning of Y, structurally different fiber-reactive groups —SO
2
—Y. In particular, the dye mixture can contain dyes of the same chromophore conforming to the formula (1) and/or dyes of the same chromophore conforming to formula (2) in which the fiber-reactive groups —SO
2
—Y are partly vinylsulfonyl groups and partly &bgr;-chloroethylsulfonyl or &bgr;-thiosulfatoethylsulfonyl or preferably &bgr;-sulfatoethylsulfonyl groups. If the dye mixtures contain the respective dye components in the form of a vinylsulfonyl dye, the proportion of the respective vinylsulfonyl dye to the respective &bgr;-chloro- or &bgr;-thiosulfato- or &bgr;-sulfatoethyl-sulfonyl dye will be up to about 30 mol-%, based on the respective dye chromophore. Y is preferably vinyl or &bgr;-sulfatoethyl. Preference is here given to the dye mixtures in which the proportion of vinylsulfonyl dye to the &bgr;-sulfatoethylsulfonyl dye is in terms of the molar ratio between 5:95 and 30:70.
Preference is given to inventive dye mixtures containing disazo dyes(s) of the formula (1) wherein a is the number 1 and b is the number 0. Preferred dye mixtures of this type comprise one or more disazo dyes conforming to the formula (5) and one or more disazo dyes conforming to the formula (6)
where M is as defined above and D
1
, D
2
, D
3
, D
4
are each independently of the others 3-vinylsulfonylphenyl, 4-vinylsulfonylphenyl, 3-(&bgr;-sulfatoethyl-sulfonyl)phenyl or 4-(&bgr;-sulfatoethylsulfonyl)phenyl. If vinylsulfonyl as well as &bgr;-sulfatoethylsulfonyl groups are present in such dye mixtures the molar ratio between the vinylsulfonyl portions and the &bgr;-sulfatoethylsulfonyl portions is in a molar ratio between 5:95 and 30:70.
Preferred dye mixtures of this type comprise furthermore one or more disazo dyes conforming to the formula (5) above and one or more diazo dyes conforming to the formula (6) above where M is as defined above, D
1
, D
2
and D
4
are each independently of the others 3-vinylsulfonylphenyl, 4-vinylsulfonylphenyl, 3-(&bgr;-sulfatoethyl-sulfonyl)phenyl or 4-(&bgr;-sulfatoethylsulfonyl)phenyl and D
3
is 2-methoxy-5-(&bgr;-sulfatoethylsulfonyl)phenyl or where M is as defined above, D
1
and D
2
are each independently of the others 3-vinylsulfonylphenyl, 4-vinylsulfonylphenyl, 3-(&bgr;-sulfatoethyl-sulfonyl)phenyl or 4-(&bgr;-sulfatoethylsulfonyl)phenyl and D
3
and D
4
are 2-methoxy-5-(&bgr;-sulfatoethylsulfonyl)phenyl.
Especially preferred dye mixtures comprise 80 to 90% of a disazo dye of the formula (9) and 10 to 20% of a disazo dye of the formula (10), wherein M is as defined above.
If inventive dye mixtures contain disazo dyes(s) of the formula (1) wherein a is the number 0 and b is the number 1 Z
2
is preferably hydrogen and Z
1
is preferably a fiber-reactive group of the formulae 3d or 3e.
In the fiber-reactive groups of the formulae 3a and 3b Q is preferably alkoxy of 1 to 4 carbon atoms, most preferably methoxy, or is a compound of formula 4b, most preferably 4-(&bgr;-sulfatoethylsulfonyl)aniline.
The dyes of the formulae (1) and (2) are well known from the literature, for example the disazo dyes of the formula (1) from U.S. Pat. No. 2,657,205 and from Japanese Patent Application Publication Sho-58-160 362 and also U.S. Pat. No. 4,257,770 and the references cited therein. Disazo dyes of the formula (2) are described in the Korean Pat. No. 90-4223.
The dye mixtures of the invention can be prepared in solid or liquid (dissolved) form. In solid form they generally contain the electrolyte salts customary in the case of water-soluble and in particular fiber-reactive dyes, such as sodium chloride, potassium chloride and sodium sulfate, and also the assistants customary in commercial dyes, such as buffer substances capable of establishing a pH in aqueous solution between 3 and 7, such as sodium acetate, sodium borate, sodium bicarbonate, sodium dihydrogenphosphate and disodium hydrogenphosphate, small amounts of niccatives or, they are present in liquid, aqueous solution (including the presence of thickeners of the type customary in print pastes), substances which ensure the permanence of these preparations, for example mold preventatives.
In general, the dye mixtures will take the form of dye powders containing 10 to 80% by weight, based on the dye po
Connolly Bove & Lodge & Hutz LLP
Dystar Textilfarben GmbH & Co.
Einsmann Margaret
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