Dyes and methods of preparing them

Details Dyes and methods of preparing them Dyes and methods of preparing them

2003-05-29

2004-05-11

Powers, Fiona T. (Department: 1626)

Organic compounds -- part of the class 532-570 series

Organic compounds

Azo

C534S612000, C534S636000, C534S637000, C534S642000, C562S058000, C008S549000

Reexamination Certificate

active

06734290

ABSTRACT:

TECHNICAL FIELD
The present writing relates to fiber-reactive dyes, which have two heterogeneous monoazo dye radical moieties in the chemical structure thereof, and methods of preparing them.
BACKGROUND
Fiber-reactive dyes with two monoazo dye radical moieties in the molecular structure have been disclosed in U.S. Pat. No. 5,484,899 and U.S. Pat. No. 5,548,071.
The dyes according to the present writing are distinguished by an excellent fixing capacity and good wet- and light-fastness properties. Accordingly, the dyes according to this writing can solve problems occurring upon dying fibre materials at a high concentration with C.I. Reactive Red 120 compound and C.I. Reactive Yellow 84 compound, being monochlorotriazine-based reactive dyes, and with C.I. Reactive Red 195 compound and C.I. Reactive Yellow 145 compound, being difunctional reactive dyes, of which the structures are illustrated below, respectively.
In recent, more advanced methods are required to dye fibre materials with reactive dyes in view of the quality of dyed goods and of the efficiency of dying process, which needs novel reactive dyes that have a sufficient direct-dyeing property in the dyeing process and, if not fixed on fiber, can be easily washed. Accordingly, the novel reactive dyes are strongly required that also have an excellent fastness to light, laundering, etc. while satisfying the above requirements.
Therefore, an object of the present invention is to provide reactive dyes which have a high fixing capacity and a high fiber-dye bond stability and an excellent fastness property to light and water and in which a part of dyes, having been not fixed on a fiber, can be easily washed. Furthermore, the reactive dyes in accordance with the present invention exhibit a significantly higher solubility than do the well-known dyes in which two heterogeneously or homogeneously monoazo moieties are connected to each other in a backbone, thereby show a much higher reproducing property in the exhausting dyeing and continuous dyeing.
The inventors of the present writing, after having conducted extensive research and many experiments, found that novel dyes as described in the formula 1 have a good build-up capacity as well as an excellent fastness property to light and water laundering, and do not almost leave non-fixed residual components due to an excellent adsorbing/fixing properties to have an advantage in wastewater treatment, as compared with existing monochlorotriazine-based dyes and heterogeneous difunctional dyes. The dye described herein can be used in dyeing and printing fibre materials, especially cellulosic fibre material by a general fixing method. The dye has a good absorbing/fixing rate and has excellent fastness to light and wet treatments (i.e. the dye exhibits excellent color fastness when exposed to light and/or wet treatments (e.g., with water)).
SUMMARY
The fiber-reactive dye of the present invention is as defined in the formula
wherein,
R
11
is a lower alkyl group of C
1
-C
4
;
D is a monoazo chromophore moiety selected from the formulas 2a, 2b, 2c, 3a and 3b defined as the below;
in the formulas 2a to 2c,
a is 0 or 1;
b is 0 or 1;
c is 0 or 1;
d is 0 or 1;
e is 0 or 1;
f is 0 or 1;
1 is the number 0 or 1;
R
1
and R
3
independently of one another are each hydrogen atom or C
1
-C
4
alkyl group;
R
2
is sulfo, C
1
-C
4
alkyl, C
1
-C
4
alkylalkoxy or carboxyl group;
R
4
is sulfo, C
1
-C
4
alkyl, C
1
-C
4
alkylalkoxy, —NHCONH
2
or —NHCOT group, wherein T is methyl, ethyl, —CH
2
CH
2
COOH or —CH═CHCOOH group; and
J is vinyl or CH
2
—CH
2
—Q group, wherein Q is a leaving group which can be eliminable by a base:
in the formulas 3a and 3b,
g is 0 or 1;
his 0 or 1;
R
5
is C
1
-C
4
alkyl, C
1
-C
4
alkoxy, hydroxyl, carbonyl, sulfo or —SO
2
J group, wherein J is the same group as defined above;
R
6
is C
1
-C
4
alkyl or carboxyl group;
R
7
and R
8
independently of one another are each C
1
-C
4
alkyl group; and
R
9
is hydrogen atom, carboamido, sulfomethyl, methylsulfone group;
R
0
is hydrogen atom or C
1
-C
4
alkyl group, wherein the alkyl group is substituted with halogen atom, hydroxyl, cyano, C
1
-C
4
alkoxy, C
1
-C
4
alkoxy carbonyl, carbonyl or sulfo group, or unsubstituted;
X is a halogen atom, hydroxyl, cyanoamine, 3-carboxypyridine-1-yl, 4-carboxypyridine-1-yl, 3-carbamoylpyridine-1-yl or an amine group optionally substituted with C
1
-C
4
alkoxy or C
1
-C
4
alkyl group or unsubstituted, or X is an N-heterocyclic group in which hetero atom(s) may be additionally contained; and
Z is the group of the formula 4 defined as the below.
in the formula 4:
l is 0 or 1;
j is 0 or 1;
k is 0 or 1;
R
10
is sulfo, C
1
-C
4
alkyl, C
1
-C
4
alkoxy or carboxyl group; and
J
1
is vinyl or CH
2
—CH
2
—Q group, wherein Q is a leaving group which is eliminable by a base.
The fiber-reactive dye of the formula 1 according to the present invention has a higher reactivity, and a better fixing capacity and more excellent build-up capacity than do the existing monochlorotriazine-based compounds and vinylsulfone-based compounds.
Preferably, R is hydrogen atom, B is an ethyl group, and X is fluoride or chloride atom.
Of compounds according to the formula 1, more preferable fiber-reactive dyes are the compounds defined as in the formulas 5 to 8 below.
wherein
A is ammonia or C
1
-C
3
alkyl group;
X
1
is fluoride or chloride atom; and
m is 0 or 1;
n is 0 or 1; and
o is 0 or 1;
wherein
1 is the number 0 or 1;
p is 0 or 1;
q is 0 or 1;
r is 0 or 1;
s is 0 or 1;
R
2
is sulfo, C
1
-C
4
alkyl, C
1
-C
4
alkoxy or carboxyl group;
X
1
is fluoride or chloride atom; and
J is vinyl or CH
2
—CH
2
—Q group, wherein Q is a leaving group which is eliminable by a base;
wherein
1 is the number 0 or 1;
p is 0 or 1;
q is 0 or 1;
r is 0 or 1;
s is 0 or 1;
R
2
is sulfo, C
1
-C
4
alkyl, C
1
-C
4
alkoxy or carboxyl group;
X
1
is fluoride or chloride atom; and
J is vinyl or CH
2
—CH
2
—Q group, wherein Q is a leaving group which is eliminable by a base;
wherein
t is 0 or 1;
u is 0 or 1;
R
8
is hydrogen atom or C
1
-C
4
alkyl group, wherein the alkyl group is substituted with halogen atom, hydroxyl, cyano, C
1
-C
4
alkoxy, C
1
-C
4
alkoxycarbonyl, carbonyl, sulfo group, or unsubstituted;
R
9
is hydrogen atom, carboamide, sulfomethyl, methylsulfone group; and
X
1
is fluoride or chloride atom.
Methods of preparing the compounds of the formula 1 are described below. Hereinafter, R
11
, D, R
0
, X and Z in the formulas 9 to 13 are the same as in the formula 1, unless stated otherwise. For convenience of explanation, the formulas 9 to 13 are first illustrated.
in the formulas 12 and 13, D
1
RN corresponds to D in the formula 1, wherein D
1
is a monoazo chromophore moiety; R is a substituted or unsubstituted C
1
-C
4
alkyl group.
The compound of the formula 13, which is substantially the same as the dye defined in the formula 1, can be synthesized by one of three methods as below. It is noted that D in the formula 1 is expressed as D
1
RN in formula 13 for convenience of explanation.
A first method of preparing the compound of the formula 13 comprises,
A-1) the compound of the formula 11 is condensed with the compound of HNR-D
1
, followed by being condensed with the compound of the formula 9, to yield to the compound of the formula 12; and
A-2) the compound of the formula 12 is coupled with a diazonium salt derived from the compound of H
2
N-Z to yield the compound of the formula 13.
A second method of synthesizing the compound of the formula 13 comprises,
B-1) the compound of the formula 9 is coupled with a diazonium salt derived from the compound of H
2
N-Z to yield the compound of the formula 10; and
B-2) the compound of the formula 11 is condensed with the compound of the formula 10, followed by being condensed with HNR-D
1
, to yield the compound of the formula 13.
A third method of synthesizing the compound of the formula 13 comprises,
C-1) the compound of the formula 11 is condensed with the compound of the formula 9, followed by being condensed with the compound of H
2
N-Z to yield the comp

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