Disperse dye mixtures

Details Disperse dye mixtures Disperse dye mixtures

2001-04-13

2003-11-04

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, C008S643000, C008S922000, C008S638000

Reexamination Certificate

active

06641620

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 the dyes of the so-called pyrroline type with those of the so-called anthraquinone type.
Dyes of the 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 Formula (2):
or a group of Formula (3):
or a group of Formula (4):
R
1
is alkyl, cycloalkyl, aryl, alkenyl 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
1-6
-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
10
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
4
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
3
-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
.
Dyes of the anthraquinone type are also well known. For example, dyes and mixtures of dyes each within the formula given below are commercially available as C.I. Disperse Blue 60 type dyes:
where R
B
is (CH
2
), —O—R
B
1
, in which n is 1-6 and R
B
1
, is straight or branched alkyl or alkoxy (and examples of R
B
are C
2
H
4
OCH
3
, C
3
H
6
OCH
3
, C
3
H
6
OC
2
H
5
and C
3
H
6
OC
2
H
4
OCH
3
) and Z
B
is O or NH.
However, if dyes of the pyrroline type alone (or mixtures of such pyrroline-type dyes) are dyed on polyester, build up to heavy depths of shade is difficult to achieve, light fastness is average at best, the dyes tend to be rather sensitive to changes in the pH of dyeing and undesirable redder shades are sometimes seen.
If dyes of the anthraquinone type alone (or mixtures of such anthraquinone-type dyes) are dyed on polyester, they often exhibit very good light fastness, but with poor build up. Moreover, they are tinctorially very weak and therefore expensive for colouring polyester. Moreover, high strength liquid or grain formulations cannot be achieved. In addition, although good build up can be achieved, the shade becomes duller as the dye builds up.
We have now found surprisingly that if certain dyes of the pyrroline type are mixed with certain dyes of the anthraquinone type, brighter shades are maintained as the dyes build up. Moreover, the dyeings have good light fastness. In particular, as compared with anthraquinone dyes alone, when using mixtures with pyrroline dyes, products of high colour strength can be readily formulated, with greater cost-effectiveness.
Thus the invention provides a dye mixture comprising
(A) at least one pyrroline type dye of the formula (I);
wherein R
1
is H, C
1-20
alkyl or C
2-20
alkenyl; and D is aryl; and
(B) at least one anthraquinone type dye of the formula (II)
wherein R
B
is (CH
2
)
n
OR
B
1
;
R
B
1
is a straight or branched chain C
1-6
alkyl or C
1-6
alkoxy-C
1-6
alkyl;
n is 1-6; and
Z
B
is O or NH.
Component (A) preferably comprises a dye of the formula (I) wherein D is a group of the formula (a)
wherein each of R
2
and R
3
independently is an alkyl, cycloalkyl, aryl, alkenyl or aralkyl group.
In the above formula (I), the alkyl group represented by any of R
1
-R
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
2
or R
3
is preferably a C
4-8
-cycloalkyl and more preferably a cyclohexyl group. The aryl group represented by R
2
or R
3
is preferably phenyl. The alkenyl group represented by any of R
1
-R
3
is preferably a C
2-10
-alkenyl, more preferably a C
2-6
-alkenyl and especially a C
2-3
-alkenyl group, such as allyl. The aralkyl group represented by any of R
1
-R
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
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
1
is more preferably a C
1-6
-alkyl and still more preferably C
1-8
-alkyl group.
R
1
is especially preferably —H, C
1-4
-alkyl or C
2-3
alkenyl, more preferably —H or C
1-4
-alkyl and especially —H.
D is preferably a group of Formula (a).
The alkyl groups represented by any of R
1
-R
3
may be straight or branched chain alkyl groups. R
2
is preferably C
1-12
-alkyl more preferably C
1-8
-alkyl especially unsubstituted C
1-8
alkyl. R
3
may be C
7-12
-alkyl and preferably C
7-9
-alkyl, especially unsubstituted C
7-9
-alkyl or may be unsubstituted C
1-6
-alkyl. Where D is a group of Formula (a) it is preferred that one or both of R
2
and R
3
is branched, more preferably branched at an &agr;- or &bgr;-, i.e. 1- or 2-, position. It is preferred that R
2
and R
3
are different. It is also preferred that ring A is unsubstituted apart from the NR
2
R
3
group.
A preferred sub-group of dyes of Formula (I) is that in which D is a group of Formula (a):
R
1
is alkyl or —H;
R
2
is alkyl;
R
3
is C
7-20
-alkyl; and
Ring A is unsubstituted apart from the —NR
2
R
3
group.
Another preferred sub-group of dyes of Formula (I) is that in which D is a group of the Formula (a);
R
1
is —H or alkyl;
R
2
is unsubstituted C
1-8
-alkyl;
R
3
is unsubstituted C
1-6
-alkyl; and
Ring A is unsubstituted apart from the —NR
2
R
3
group; and
R
2
and R
3
are different or at least one of R
2
and R
3
is a branched chain alkyl.
An especially preferred sub-group of dyes of Formula (I) is that in which D is a group of Formula (a):
R
1
is —H;
R
2
is unsubstituted C
1-8
alkyl;
R
3
is unsubstituted C
7-9
alkyl; and
Ring A is unsubstituted apart from the —NR
2
R
3
group.
A further especially preferred sub-group of dyes of Formula (I) is that in which D is a group of Formula (a);
R
1
is —H;
R
2
is n-propyl or n-butyl;
R
3
is 1-methylhexyl or 2-ethylhexyl; and
Ring A is unsubstituted apart from the —NR
2
R
3
group.
Typical especially preferred components (A) in mixtures embodying the invention are:
(1) a pyrroline type dye of the formula (I), wherein R
1
is H, R
2
is C
4
H
9
and R
3
is 1-methyl-n-hexyl (A
1
) or a mixture thereof with up to 10% by weight of component (A), of a pyrroline type dye (A
2
) of the formula (I), wherein R
1
is H and each of R
2
and R
3
is C
4
H
9
;
(2) a pyrroline type dye of the formula (I), wherein R
1
is H, R
2
is ethyl and R
3
is n-octyl (A
3
) or 2-ethyl-n-hexyl (A
4
) or a mixture of dyes (A
3
) and (A
4
); and
(3) a pyrroline type dye of the formula (I), wherein

Affiliated with

Also associated with

Rating

Disperse dye mixtures does not yet have a rating. At this time, there are no reviews or comments for this patent.

If you have personal experience with Disperse dye mixtures, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Disperse dye mixtures will most certainly appreciate the feedback.

Rate now

Comments { 0 }

Profile ID: LFUS-PAI-O-3148739