Bleaching and dyeing; fluid treatment and chemical modification – Reactive dye composition – process – or product – Alkylene sulfato – halotriazine – halodiazine,...
Reexamination Certificate
1999-12-07
2001-02-20
Einsmann, Margaret (Department: 1751)
Bleaching and dyeing; fluid treatment and chemical modification
Reactive dye composition, process, or product
Alkylene sulfato, halotriazine, halodiazine,...
C008S641000, C008S692000
Reexamination Certificate
active
06190423
ABSTRACT:
DESCRIPTION
The present invention relates to the field of fiber-reactive dyes. It describes yellow to orange mixtures of fiber-reactive monoazo dyestuffs and use thereof for dyeing hydroxy- and/or carboxamido-containing fiber material.
The dyes according to the general formulae (1) are known from the German Patent DE-C 1215282. Dyes according to the general formulae (2) are known from the German Patents DE-C 1911427, DE-C 1644240 and the U.S. patents U.S. Pat. No. 4,725,675, U.S. Pat. No. 4,703,112.
The mixtures composed from dyes of formula (1) and formula (2) are new and provide advantages, such as color build-up and solubility in an aqueous dyebath in the presence of alkali and electrolyte salts over the individual dyes represented by formula (1) or formula (2).
The present invention concerns dye mixtures of fiber-reactive azo dyes, suitable for dyeing hydroxy- and/or carboxamido-containing material in yellow to orange shades, which comprise one or more disazo dyestuffs corresponding to the general formula (1) and one or more monoazo dyestuff corresponding to the formula (2)
in which
R
1
is hydrogen, sulfo, C
1
-C
4
alkyl or alkoxy or halogen and preferably hydrogen
R
2
has one of the meanings of R
1
;
R
3
is C
1
-C
4
-alkyl, phenyl, carboxy or C
1
-C
4
-carboxyalkyl, preferably carboxy, carboxymethyl and in particular preferably methyl
R
4
has one of the meanings of R
3
;
Y
1
is vinyl or is ethyl which is substituted in the &bgr;-position by a substituent which is eliminated by the action of an alkali, forming the vinyl group,
Y
2
has one of the meanings of Y
1
;
B is a radical of the formulae (3) or (4) or (5); if B is (5) then K is preferably (10) or is preferably (11) provided that D is a structure of the formula (3);
M is hydrogen or an alkali metal, such as lithium, sodium and potassium;
in which,
R
5
has one of the meanings of R
1
;
R
6
has one of the meanings of R
1
;
Y
3
has one of the meanings of Y
1
;
Y
4
has one of the meanings of Y
1
;
m is a number 0, 1, or 2;
i is a number 0 or 1;
n is a number 0 or 1; whereby, n is 0 only when coupled to the coupling formulae (10) or (11) with the proviso that if n is 0 then D in formula (11) is a structure of the formula 3;
M is hydrogen or an alkali metal, such as lithium, sodium and potassium;
K is a coupling component represented by formulae (6), (7), (8), (9), (10) or (11);
in which
R
7
has one of the meanings of R
1
;
R
8
has one of the meanings of R
1
;
R
9
has one of the meanings of R
1
;
R
10
is amino, substituted or unsubstituted C
1-C
4
alkyl, in which the preferred substituent is carboxy, or substituted or unsubstituted phenyl, in which the preferred substituent is carboxy or sulfo;
R
11
is substituted or unsubstituted C
1
-C
6
alkyl, in which the preferred substituent is carboxy, or is substituted or unsubstituted phenyl, in which the preferred substituent is carboxy or sulfo;
D is the radical (3), (4), or (5);
G is amino or hydroxy;
X is hydroxy, chloro, fluoro, morpholino, nicotinamido, 3-carboxypyridino, or a radical of the formulae L;
r,s,t,w is the number 0 or 1;
p is the number 1 or 2; and
L has one of the meanings of formulae (12), (13), or (14);
M is hydrogen or an alkali metal, such as lithium, sodium and potassium;
in which
R
12
is hydrogen, C
1-C
4
alkyl or alkoxy, halogen or sulfo;
R
13
is hydrogen or C
1-C
4
alkyl or alkoxy; halogen or sulfo;
R
14
is hydrogen, C
1
-C
6
alkyl, or substituted or unsubstituted phenyl, in which the preferred substituents are C
1-C
4
alkyl or alkoxy, or sulfo;
R
15
is hydrogen or sulfo;
R
16
is hydrogen, C
1
-C
6
alkyl, or substituted or unsubstituted phenyl, in which the preferred substituents are C
1-C
4
alkyl or alkoxy, or sulfo;
R
17
is hydrogen, C
1-C
6
alkyl, or substituted or unsubstituted phenyl, in which the preferred substituents are C
1-C
4
alkyl or alkoxy, or sulfo;
Y
5
has one of the meanings of Y
1
Y
6
has one of the meanings of Y
1
;
n′ is the number 0 or 1.
q represents C
1
-C
5
-alkylene groups, which may be interrupted by a nitrogen, oxygen, or sulfur atom; and
Z is a radical of the formulae (12) or (14).
Radicals of the formulae (3)
of the azo dyestuffs of the formulae (2) are, for example, 3-(&bgr;-sulfatoethylsulfonyl)-, 4-(&bgr;-sulfatoethylsulfonyl)-, 2-methyl-5-(&bgr;-sulfatoethylsulfonyl)-, 2-methoxy-5-(&bgr;-sulfatoethylsulfonyl)-, 4-methyl-3-(&bgr;-sulfatoethylsulfonyl)-, 2,5-dimethyl-(&bgr;-sulfatoethyl-sulfonyl)-, 2,6-dimethyl-4-(&bgr;-sulfatoethylsulfonyl)-, 2-methoxy-4-(&bgr;-sulfatoethylsulfonyl)-, 4-methoxy-5-(&bgr;-sulfatoethylsulfonyl)-, 2,4-dimethoxy-5-(&bgr;-sulfatoethylsulfonyl)-, or 2,5-dimethoxy-4-(&bgr;-sulfatoethylsulfonyl)-, 2-sulfo-4(&bgr;-sulfatoethylsulfonyl-).
Radicals of the formulae (4)
of the azo dyestuffs of the formulae (2) are, for example, 2-Amino6-(&bgr;-sulfatoethylsulfonyl)-1-sulfo-naphthyl-2- and 2-Amino-8-(&bgr;-sulfatoethylsulfonyl)-6-sulfonaphthyl-.
Radicals of the formulae (5)
of the azo dyestuffs of the formulae (2) are, for example, 2-amino-5-[(4′-sulfophenyl)azo]benzenesulfonic acid, 4-amino-4-[(4′-sulfophenyl)azo]benzene, and 2-amino-5-[(4′-Sulfo-phenyl)azo]benzene.
Coupling components of the formulae (6)
for the preparation of the azo dyestuffs of the formula (2) are, for example, 2′-Methoxy-5′-methyl-4′-sulfoacetoacetanilide, 2′,5′-Dimethoxy-4′-sulfoacetoacetanilide, 2′,5′-Dimethyl-4′-sulfoaceto-acetanilide, or 2′-Methoxy-4′-sulfoacetoacetanilide.
Coupling components of the formulae (7)
for the preparation of the azo dyestuffs of the formula (2) are, for example, 2,4-Diaminobenzeneulfonic acid, 2,5 Diaminobenzenesulfonic acid, 3′-Amino-4′sulfoacetanilide, 3′-Aminophenylurea, or 3′-Amino-4′-sulfophenylurea.
Coupling components of the formulae (8)
for the preparation of the azo dyestuffs of the formula (2) are, for example, 1 -Aminonaphthalene-4-sulfonic acid, 1-Aminonaphthalene-3-sulfonic acid, 1-Aminonaphthalene-5-sulfonic acid, 1-Aminonaphthalene-6-sulfonic acid, 1-Aminonaphthalene-7-sulfonic acid, 1-Aminonaphthalene-8-sulfonic acid, 2-Aminonaphthalene-4-sulfonic acid, 2-Aminonaphthalene-5-sulfonic acid, 2-Aminonaphthalene-6-sulfonic acid, 1-Hydroxynaphthalene-4-sulfonic acid, 1-Hydroxynaphthalene-3-sulfonic acid, 1-Hydroxynaphthalene-5-sulfonic acid, 1-Hydroxynaphthalene-6-sulfonic acid, 1-Hydroxynaphthalene-7-sulfonic acid, 1-Hydroxynaphthalene-8-sulfonic acid, 2-Hydroxynaphthalene-4-sulfonic acid, 2-Hydroxynaphthalene-5-sulfonic acid, 2-Hydroxynaphthalene-6-sulfonic acid, 2-Hydroxynaphthalene-7-sulfonic acid, or 2-Hydroxynaphthalene-8-sulfonic acid.
Coupling components of the formulae (9)
for the preparation of the azo dyestuffs of the formula (2) are, for example, Acetyl-J-acid, Acetyl-gamma-acid, Acetyl H-acid, or Acetyl K-acid, Benzoyl H-acid, or Benzoyl K-acid.
Representative amino compounds of the formula (13), of the azo dyes of formulae
are for example, 4-Amino-N-(4-((&bgr;-sulfatoethyl)sulfonyl)phenyl)benzamid, 4-Amino-N-(3-((&bgr;-sulfatoethyl)sulfonyl)phenyl)benzamid, 4-Amino-3-Sulfo-N-(4-((&bgr;-sulfatoethyl)sulfonyl)phenyl)benzamid, 4-Amino-3-Sulfo-N-(3-((&bgr;-sulfatoethyl)sulfonyl)phenyl)benzamid, or 3-Amino-4-Sulfo-N-(3-((&bgr;-sulfatoethyl)sulfonyl)phenyl)benzamid.
Representative amino compounds of the formulae (14), of the coupling components (10)
are for example, N-phenyl-N-[2-(&bgr;-sulfatoethylsulfonyl)-ethylamine, 3-(&bgr;-Sulfatoethylsulfonyl)-propylamine, N-methyl-3-(&bgr;-sulfatoethylsulfonyl)propylamine, N-methyl-2-(&bgr;-sulfatoethylsulfonyl)-ethylamine, 2-(&bgr;-Sulfatoethylsulfonyl)-ethylamine, 3-(&bgr;-Chloroethylsulfonyl)-propylamine, 2-[2′-(&bgr;-Sulfatoethylsulfonyl)-ethoxy]-ethylamine, und 2-[2′-(&bgr;-Chloroethylsulfonyl)ethoxy]-ethylamine.
Representative bisamino components of the formulae (15)
of the azo dyestuffs of the formula (1) are, for example, 4,4′Diaminodiphenyl-2,2′disulfonic acid and 4,4′-Diaminodiphenyl-
Pedemonte Ronald
Reiher Uwe
Russ Werner
Schumacher Christian
Steckelberg Joachim
Connolly Bove & Lodge & Hutz LLP
DyStar Textilfarben GmbH & Co
Einsmann Margaret
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