Dyes

Details Dyes Dyes

1995-05-03

1997-08-26

Einsmann, Margaret

Bleaching and dyeing; fluid treatment and chemical modification

Multiple chemically diverse fibers or fibers with different...

Polyester fiber and cellulose fiber

8533, 8921, 8922, 8924, 8926, 544353, 548466, 548550, C09B 2300, C09B 6722, D06P 116, D06P 3852

Patent

active

056605986

DESCRIPTION:

BRIEF SUMMARY
This invention relates to dyes particularly 4-cyano-5-dicyanomethylidene derivatives, mixtures thereof, mixtures with other dyes types, their use to colour textile materials and to a process for the manufacture of such dyes.
Various types of disperse dyes, such as anthraquinone and azo dyes, have been used to dye synthetic textile materials blue to green shades but few of these have fully satisfactory properties and either do not build up well on the material, have poor temperature range properties or have inadequate light or wet fastness or are dyebath unstable or dull in shade.
The market leading dye in this shade area is an anthraquinone dye, C.I. Disperse Blue 60, its build up, heat fastness properties, on synthetic textile material, and its dyebath stability are relatively poor and it is tinctorially weak and thus relatively expensive to use.
GB 2191498 discloses certain symmetrical N,N-di-C.sub.1-6 -alkyl or substituted N-alkyl pyrroline dyes which are generally poor dyes which do not build up well on synthetic textile materials.
According to the present invention there is provided a dye of Formula (1): ##STR5## wherein:
D is a group of Formula (2): ##STR6##
or a group of Formula (3): ##STR7##
or a group of Formula (4): ##STR8##
R.sup.1 is alkyl, cycloalkyl, aryl, alkenyl or aralkyl each of which may be optionally substituted;
R.sup.2 is optionally substituted C.sub.7-20 -alkyl; or
R.sup.1 and R.sup.2 together with the nitrogen atom to which they are attached form a pyrrolidino or piperidino ring;
R.sup.3 is --H or alkyl, alkenyl or aralkyl each of which may be optionally substituted, --SO.sub.2 alkyl, --SO.sub.2 aryl or --COR in which R is --H or alkyl, phenyl, cycloalkyl or aralkyl each of which may be optionally substituted; and
R.sup.4 is an electron withdrawing group;
R.sup.6 is optionally substituted C.sub.1-6 -alkyl; or
R.sup.1 and R.sup.6 together with the nitrogen atom to which they are attached form a pyrrolidino or piperidino ring;
R.sup.7, R.sup.8, R.sup.9 and R.sup.10 each independently is --H or alkyl, cycloalkyl, aryl, alkenyl or aralkyl each of which my be optionally substituted;
W is oxygen or sulphur;
Z is a direct link or N--R.sup.11 in which R.sup.11 is --H or optionally substituted alkyl, or aryl;
Ring A is unsubstituted apart from the --NR.sup.1 R.sup.2 group or is substituted by from 1 to 4 further groups;
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 (2) and R.sup.1 and R.sup.2 are both allyl that R.sup.4 is not --CN; and
(b) when D is a group of Formula (3) that R.sup.1 and R.sup.6 are different and R.sup.1 is not --C.sub.2 H.sub.5, --C.sub.3 H.sub.7 or --C.sub.4 H.sub.9 when R.sup.6 is --C.sub.2 H.sub.4 phenyl, --C.sub.3 H.sub.6 phenyl and ethyl substituted by --OH, --CN, --OCH.sub.3, --OC.sub.2 H.sub.4 OC.sub.2 H.sub.5, --NHCOCH.sub.3, --Ophenyl and --NHSO.sub.2 CH.sub.3 ; or
(c) that at least one of R.sup.1 and R.sup.6 is branched chain alkyl.
The dyes of the present invention and mixtures described herein generally do not suffer from the problems of known dyes and build up well on synthetic textile materials.
The optionally substituted alkyl group represented by R.sup.1 is preferably a C.sub.1-20 -alkyl, more preferably a C.sub.1-12 -alkyl and especially a C.sub.1-8 -alkyl group. The optionally substituted cycloalkyl group represented by R, R.sup.1, R.sup.7, R.sup.8, R.sup.9, R.sup.10 and R.sup.11 is preferably a C.sub.4-8 -cycloalkyl and more preferably a cyclohexyl group. The optionally substituted aryl group represented by R.sup.1, R.sup.7, R.sup.8, R.sup.9 R.sup.10 and R.sup.11 is preferably phenyl. The optionally substituted alkenyl group represented by R.sup.1, R.sup.3, R.sup.7, R.sup.8, R.sup.9 and R.sup. 10 is preferably a C.sub.2-10 -alkenyl, more preferably a C.sub.2-6 -alkenyl and especially a C.sub.2-3 -alkenyl group, such as allyl. The optionally substituted aralkyl group represented by R, R.sup.1,

REFERENCES:
patent: 3013013 (1961-12-01), Carboni
patent: 4845235 (1989-07-01), Matumoto
Database WPI, week 8744, Derwent Publications Ltd., AN 87-31129 & JP,A,62 220 557, Mar. 24, 1986 see abstract.

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