Disperse dye mixtures

Details Disperse dye mixtures Disperse dye mixtures

2000-11-30

2003-07-08

Einsmann, Margaret (Department: 1751)

Bleaching and dyeing; fluid treatment and chemical modification

Multiple chemically diverse fibers or fibers with different...

Polyester fiber and cellulose fiber

C008S533000, C008S638000, C008S639000, C008S922000

Reexamination Certificate

active

06589296

ABSTRACT:

This invention relates to mixtures of disperse dyes, compositions comprising dispersions of such mixtures and processes for the colouration of synthetic materials with such mixtures. More particularly, the invention relates to mixtures of reddish blue monoazo dyes with those of the so called pyrroline type, which tend to be greenish blue.
Monoazo dyes of the above type are disclosed in EP-A-0300626 and EP-A-0347685.
As a component of a mixture of dyes, EP-A-0300626 discloses a dye of the formula
where X is Br, Cl or I; Q is C
1-4
alkyl; and each of R
1
and R
2
independently is C
1-4
alkyl or C
2-4
alkenyl.
Similarly, as a component of a mixture of dyes, EP-A-0347685 discloses a dye of the formula
wherein Y is NO
3
or CN, R
1
is alkyl aralkyl alkoxyalkyl or alkenyl and R
2
is alkyl, aralkyl, alkoxyalkyl, alkenyl, chloroalkyl, aryloxyalkyl or alkoxycarbonyalkyl. Such dyes are in admixture with, for example, monoazo-dyes containing a thiophene nucleus.
WO-A-97004030 discloses mixtures of the following dye with a thiophene dye in various proportions.
Dyes of the abovementioned pyrroline type are disclosed, for example, in U.S. Pat. No. 3,013,013, U.S. Pat. No. 3,013,018, GB-A-2191498, EP-A-0327077, EP-A-0511625 and WO-A-94010248.
In particular, WO-A-94010248 discloses dyes of the pyrroline type having the formula (1).
wherein:
D is a group of the Formula (2)
 or a group of Formula (3):
 or a group of the Formula (4)
R
1
is alkyl, cycloalkyl, aryl, a kenyl or aralkyl each of which may be optionally substituted;
R
2
is optionally substituted C
7-20
-alkyl; or
R
1
and R
2
together with the nitrogen atom to which they are attached form a pyrrolidino or piperidino ring;
R
3
is alkyl, alkenyl or aralkyl each of which may be optionally substituted, —SO
2
alkyl, —SO
2
aryl, or —COR in which R is —H or alkyl, phenyl, cycloalkyl or aralkyl each of which may be optionally substituted or —H; and
R
4
is an electron withdrawing group;
R
6
is optionally substituted C
1-14
-alkyl; or
R
1
and R
6
together with the nitrogen atom to which they are attached form a pyrrolidino or piperidino ring;
R
7
, R
8
, R
9
and R
11
each independently is alkyl, cycloaklyl, aryl, alkenyl or aralkyl, each of which may be optionally substituted, or —H;
W is oxygen or sulphur;
Z is a direct link or N—R
11
in which R
11
is —H or optionally substituted alkyl or aryl;
Ring A is unsubstituted apart from the —NR
1
R
2
group or is substituted by from 1 to 4 further groups; and
Ring B is unsubstituted or substituted by from 1 to 3 groups; except for 3-(4-(N,N-di-n-octylamino)phenyl)-4-cyano-5-dicyano methylidene-2-oxo-2,5-dihydropyrrole
provided that:
(a) when D is a group of Formula (3), R
1
and R
6
are different and R
1
is not —C
2
H
5
, —C
3
H
7
or —C
1
H
9
when R
6
is —C
2
H
4
phenyl, —C
3
H
6
phenyl and ethyl substituted by —OH, —CN, —OCH
3
, —OC
2
H
4
OC
2
H
5
, —NHCOCH
2
—Ophenyl and —NHSO
2
CH
3
; or
(b) at least one of R
1
and R
6
is branched chain alkyl. Commercially available dyes of the pyrroline type are, for example, dyes of the formula:
 where R
A
is H (Kayalon Polyester Brilliant Blue F2B-S); or CH
2
CH═CH
2
(Kayalon Polyester Blue-Green FG-S); and dyes of the formula
 where X
A
is C
4
H
9
and Y
A
is CH(CH
3
)C
5
H
11
.
It is found that certain mixtures, although giving bright shades on polyester when viewed in normal daylight, tend to exhibit a “red” flare in tungsten light which is a serious commercial disadvantage.
Although the problem of “flare” may be solved by at least one of the mixtures disclosed in EP-A-0347685, such a mixture is especially sensitive to reduction and has a relatively low heat fastness. Likewise flare can be avoided by using a dye mixture in which the nitrothiophene carries an acetyl group. However, such dyes tend to be expensive.
We have found surprisingly that a mixture of dyes, as defined below, surprisingly not only allows reduction or even elimination of the “red” flare, but provides a much brighter shade and is less sensitive to reduction with consequent loss of shade.
Thus, the invention provides a mixture of dyestuffs containing at least
(A) at least one monoazo dye of the formula (I)
 wherein X
A
is Cl, Br, I, CN or NO
2
;
R
A
is C
1-4
alkyl (or NHCOQ, where Q is C
1-4
alkyl); and
each of R
A
1
and R
A
2
independently is C
1-4
alkyl, C
2-4
alkenyl, C
1-4
-alkoxy C
1-4
alkyl, aryl-C
1-4
alkyl or aryloxy-C
1-4
alkyl; and
(B) at least one dye of the formula (II)
 wherein R
B
1
is H, C
1-20
alkyl or C
2-20
alkenyl; and
D is aryl.
In a preferred dye mixture, in a dye of the formula (I) of the mixture, an especially preferred value of X
A
is Br or CN, especially preferred values of R
A
are NHCOCH
3
, NHCOC
2
H
5
, CH
3
and C
2
H
5
and especially preferred values R
A
1
and R
A
2
are methyl, ethyl and allyl.
Typical especially preferred components (A) in mixtures embodying the invention are selected from
(A1)a monoazo dye of the formula (I), wherein X
A
is Br, R
A
is NHCOR
X
where R
X
is methyl or ethyl and each of R
A
1
and R
A
2
is ethyl;
(A2)a monoazo dye of the formula (I wherein X
A
is CN, R
A
is CH
2
and each of R
A
1
and R
A
2
is ethyl; and
(A3) a monoazo dye of the formula (I), wherein X
A
is CN, R
A
is CH
2
, R
A
1
is methyl and R
A
2
is 3-phenylpropyl.
The dyes of the formula (I) may be Prepared in a conventional manner by diazotisation and coupling.
More particularly, for dyes wherein, in formula (I), X
A
is Cl, Br or I, an amine of formula (III)
 wherein X is
Cl, Br, or I, is dlazotised and coupled with a coupling component of the formula (V)
 wherein R
A
, R
A
1
and R
A
2
are as defined above
Dyes of the formula (I), wherein X
A
is CN may be prepared by diazotizing 2,6-dibromo-4-nitroaniline and coupling to a coupling component of the formula (V) to form a precursor dye and thereafter subjecting the precursor dye to a copper catalysed cyano exchange reaction using, for example, copper cyanide or a mixture of copper and sodium cyanides, optionally in a solvent such as dimethyl formamide.
Similarly, dyes of the formula (I), whereon X
A
is NO
2
may be prepared by diazotizing 2-dibromo-4,6-dinitroaniline, coupling to a coupling component of the formula (V) and then subjecting the resulting precursor dye to the above copper catalysed cyano exchange reaction.
In the above diazotisation and coupling reactions, the diazotization is carried out using a diazotising agent, which is preferably nitrosyl sulphuric acid, optionally diluted with glacial acetic acid or a phosphoric/acetic acid mixture and preferably at a temperature of 0-10° C., more preferably 0-5° C. and preferably at a pH<1 (say 0.5) up to 7, more preferably 0.5-1, followed by a subsequent increase in pH to 3-4 to isolate the dye.
Reference is now made to component (B), which comprises a pyrroline type dye of the formula (II).
In the compound of the formula (II), D is preferably a group of the formula (a).
wherein each of R
B
2
and R
B
3
independently is alkyl, cycloalkyl, aryl, alkenyl or aralkyl.
In the above formula (II), the alkyl group represented by any of R
B
1
-R
B
3
is preferably a C
1-20
-alkyl, more preferably a C
1-12
-alkyl and especially a C
1-8
-alkyl, group. The cycloalkyl group represented by R
B
2
or R
B
3
is preferably a C
4-8
-cycloalkyl and more preferably a cyclohexyl group. The aryl group represented by R
B
2
or R
B
3
is preferably phenyl. The alkenyl group represented by any of R
B
1
-R
B
3
is preferably a C
2-10
-alkenyl, more preferably C
2-6
-alkenyl and especially a C
2-3
-alkenyl group, such as allyl. The aralkyl group represented by any one of R
B
1
-R
B
3
is preferably a phenyl-C
1-6
-alkyl, more preferably a phenyl-C
1-3
-alkyl, especially phenylethyl or 3-phenylpropyl.
The alkyl group represented by R
B
3
is more preferably a C
7-15
-alkyl, still more preferably a C
7-12
-alkyl and especially a C
7-9
-alkyl group.
The alkyl group represented by R
B
1
is more preferably a C
1-6
-alkyl and still more preferably C
1-4
-alkyl group.
R
B
1
is especiall

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