Bleaching and dyeing; fluid treatment and chemical modification – Reactive dye composition – process – or product – Alkylene sulfato – halotriazine – halodiazine,...
Reexamination Certificate
1999-11-04
2001-05-29
Einsmann, Margaret (Department: 1751)
Bleaching and dyeing; fluid treatment and chemical modification
Reactive dye composition, process, or product
Alkylene sulfato, halotriazine, halodiazine,...
C008S641000
Reexamination Certificate
active
06238442
ABSTRACT:
DESCRIPTION
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.
Yellow-dyeing fiber-reactive dyes frequently have the technical disadvantage of being more or less photochromic, i.e., that the dyeings obtainable therewith have different hues in muted light and daylight. This effect is particularly noticeable in the case of combination shade dyeings with red- and blue-dyeing dyes in certain shades, such as beige, brown and green. This disadvantage leads to problems with shade-passing the dyed production lots in textile dyehouses.
There are some monoazo dyes of the benzene-azo-benzene and naphthalene-azo-benzene series which are appreciated on account of their interesting hue and their good dyeing properties, but which appear to be in need of improvement on account of their disadvantageous photochromism. On the other hand, azo dyes having a pyrazolone coupling component are less photochromic, but frequently have deficiencies in their dyeing properties.
The present invention, then, provides dye mixtures comprising yellow-dyeing dyes, which surprisingly afford less photochromic dyeings than would be expected from the fractions of the individual dyes.
The invention thus relates to dye mixtures comprising one or more, such as two or three, preferably 1 or 2, dyes of the hereinbelow indicated and defined general formula (1a) or of the hereinbelow indicated and defined general formula (1b) or of the general formulae (1a) and (1b) and one or more, such as two or three, preferably 1 or 2, dyes of the hereinbelow indicated and defined general formula (2a) or (2b) or (2c) or of a combination of the dyes of the formulae (2a) to (2c) in a molar ratio of the dyes (1a) or (1b) or (1a) and (1b) to the dyes (2a) or (2b) or (2c) or a combination selected from the dyes (2a) to (2c) of 70:30 to 30:70, preferably 60:40 to 40:60,
wherein:
M is hydrogen or an alkali metal, such as sodium, potassium or lithium;
D is the radical of benzene or of naphthalene;
Y
1
is vinyl or is ethyl which is substituted in the Deposition 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;
R is amino or alkyl of 1 to 4 carbon atoms, such as methyl, or alkyl of I to 4 carbon atoms, such as methyl and especially ethyl, which is substituted b carboxyl, sulfo, sulfato, phosphate, hydroxyl or a —SO
2
—Y
2
group, where Y
2
has one of the meanings of Y
1
;
R
1
is hydrogen, alkyl of 1 to 4 carbon atoms, such as ethyl and especially 1 methyl, alkoxy of 1 to 4 carbon atoms, such as ethoxy and especially methoxy, or sulfo, preferably hydrogen or sulfo, R
1
being preferably disposed para to the —NH—CO—R group;
m is 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 chloro-difluoro-pyrimidines, of the dichloroquinoxalines or of the halotriazines, such as chloro- or fluorotriazines, 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 vinyl sulfone series conforming to the general formula —SO
2
—Y, where Y
3
has one of the meanings of Y
1
, and this group is attached via a bridge member, such as phenylene, methoxy-, ethoxy-, methyl-, ethyl-, sulfo- and/or chlorine-substituted phenylene, alkylene of 1 to 6 carbon atoms, which may be 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
0
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 carboxyl, the alkylene radicals contain 1 to 6 carbon atoms, preferably 2 to 4 carbon atoms, and may be substituted by sulfo or carboxyl and/or interrupted by 1 or 2 hetero groups, such as —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—;
R is methyl or carboxyl;
R
3
is hydrogen, halogen, such as chlorine, alkyl of 1 to 4 carbon atoms such as methyl or ethyl, or alkoxy of 1 to 4 carbon atoms, such as methoxy or ethoxy, preferably hydrogen, methyl or chlorine;
p is zero, 1 or 2, and
q is zero, 1 or 2,
where the sum of (p+q) is 1, 2 or 3 and the —SO
3
M group is hydrogen when p is zero or q is zero;
in the formula (2a) the —NH—Z group is attached to the benzene nucleus A or to the benzene nucleus B;
in the formula (2b) one amino group of the bridge member —NH—Z
0
13
NH— is attached to the benzene nucleus A of one monoazo radical and the other amino group is attached to the benzene nucleus B of the other monoazo radical or both the NH groups are attached to both As or to both Bs;
R is hydrogen, sulfo, alkyl of 1 to 4 carbon atoms, such as methyl or ethyl, or alkoxy of 1 to 4 carbon atoms, such as methoxy or ethoxy, preferably hydrogen or methoxy;
R
5
is methyl or carboxyl;
R is hydrogen, sulfo, carboxyl, alkyl of 1 to 4 carbon atoms, such as ethyl or methyl, or alkoxy of 1 to 4 carbon atoms, such as ethoxy or methoxy, hydrogen, sulfo or methyl;
is hydrogen, sulfo, alkyl of 1 to 4 carbon atoms, such as ethyl or methyl, or alkoxy of 1 to 4 carbon atoms, such as ethoxy or methoxy, preferably hydrogen;
n is 1 or 2;
B
0
is hydrogen when n is 1, or is a direct covalent bond, alkylene, alkenylene or alkylene-phenylene-alkylene when n is 2, in which the phenylene radicals may be substituted by 1 or 2 substituents selected from the group consisting of methoxy, ethoxy, methyl, ethyl, sulfo and carboxyl, the alkylene radicals contain 1 to 6 carbon atoms, preferably 2 to 4 carbon atoms, and may be substituted by sulfo or carboxyl and/or interrupted by 1 or 2 hetero groups, such as —O— and —NH—, and the alkenylene radicals are those of 2 to 4 carbon atoms, preferably vinylidene, or B
0
is a group of the hereinabove defined formula element Z
0
.
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, phosphate 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 formulae (1a) and (1b) may be referred to globally as “dyes (1)” and the dyes (2a), (2b) and (2c) as “dyes (2)”.
The dyes (1) and (2) 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 (1a) and (2a), Z is preferably a radical of the formula (4a), (4b), (4c) or (4d)
wherein:
Hal is as defined above;
R
8
is hydrogen, chlorine or fluorine, preferably hydrogen or chlorine;
R
18
is hydrogen or f
Eden Birgit
Schumacher Christian
Connolly Bove & Lodge & Hutz LLP
DyStar Textilfarben GmbH & Co. Deutschland KG
Einsmann Margaret
LandOfFree
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