Organic compounds -- part of the class 532-570 series – Organic compounds – Chalcogen in the nitrogen containing substituent
Patent
1995-07-11
1996-07-23
Datlow, Philip I.
Organic compounds -- part of the class 532-570 series
Organic compounds
Chalcogen in the nitrogen containing substituent
C07D49804
Patent
active
055391095
DESCRIPTION:
BRIEF SUMMARY
BACKGROUND OF THE INVENTION
1. Technical Field
This invention is directed to new fiber reactive triphenodioxazine dye.
2. Background
Anthraquinone based fiber reactive dyes have been the predominate dye used in the coloring of cotton fabdcs in bright blue colors. This dominance of the anthraquinone dyes has been threatened over the past decade or so by the increasing use of dyes based upon the triphenodioxazine chromophore.
Examples of the recent patent activity in this triphenodioxazine based dyes are: U.S. Pat. No. 4,604,459; U.S. Pat. No. 3,996,221; U.S. Pat. No. 4,092,478; U.S. Pat. No. 4,400,504; U.S. Pat. No. 4,472,575; U.S. Pat. No. 4,774,333; U.S. Pat. No. 4,629,788; and EPO 385,120 (Sep. 9, 1990).
The present invention provides new dioxazine based fiber reactive dyes with good fastness properties (light, chlorine and wash fastness), high substantivity for cellulosic fibers, high tinctorial strength and a bright reddish blue color. In addition, the dyes of the invention are easily synthesized from readily available intermediates at low costs.
SUMMARY OF THE INVENTION
The invention is that of a new triphenodioxazine dye of the formula: ##STR3## wherein: ##STR4## W=a substituted or unsubstituted arylene, alkylene or arylene-alkylene group where the alkylene moiety may be interrupted by a hetero atom selected from O, S and N; .beta.-Halogenethyl, .beta.-Phosphatoethyl, and substituted or unsubstituted alkyl of 1 to 6 carbons; preferably hydrogen and a substituted or unsubstituted C.sub.1 to C.sub.4 alkyl. alkyl, C.sub.1 to C.sub.6 alkoxy, phenyl or phenoxy; and
The dyes of the above formula provide dyeing on cotton substrates having a bright reddish blue color having good fastness or properties of high tinctodal strength. The dyes of the invention may also be used in the dyeing of other textiles containing amido and/or hydroxyl groups; exemplary materials include regenerated cellulose, synthetic polyamides, wool, silk and polyurethane fibers. The dyes of the invention may be applied by the standard methods for printing and dyeing textiles with fiber reactive dyes.
DESCRIPTION OF THE PREFERRED EMBODIMENTS
The invention relates to new triphendioxazine reactive dyestuffs of the formula: ##STR5## wherein:
R and R.sub.1 are independently selected from H or a substituted or unsubstituted alkyl, preferably hydrogen or a substituted or unsubstituted C.sub.1 -C.sub.6 - alkyl, and most preferably hydrogen or a substituted or unsubstituted C.sub.1 -C.sub.4 alkyl;
T is independently selected from H, Cl, Br, a substituted or unsubstituted C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy, phenyl, or phenoxy; ##STR6## R.sub.2 iS selected from hydrogen or a substituted or unsubstituted C.sub.1 to C.sub.6 alkyl or the group W--SO.sub.2 --Y.sup.1 ; preferably hydrogen or a substituted or unsubstituted C.sub.1 to C.sub.4 alkyl.
W is a substituted or unsubstituted arylene, or alkylene, or arylene-alkylene group wherein the alkylene group may be interrupted by a hetero atom selected from O, S and N, preferably a substituted or unsubstituted phenylene or naphthalene group or a substituted or unsubstituted C.sub.1 to C.sub.6 alkylene group, wherein said alkylene moiety may be interrupted by a hetero atom selected from O, N and S; Y.sup.1 =Vinyl, .beta.-Sulfatoethyl, .beta.-Thiosulfatoethyl, .beta.-Halogenethyl, .beta.-Phosphato, and X=H. K is independently selected from SO.sub.3 H and COOH. n=0, 1 or 2.
The term "arylene-alkylene" group as used in this specification and the claims is intended to mean a phenylene or naphthalene group bonded to one or more alkylene groups, e.g. the following illustrations or their isomers: ##STR7##
Examples of R, R.sub.1 and R.sub.2 are: hydrogen or CH.sub.3, C.sub.2 H.sub.5, n-C.sub.3 -H.sub.7, n-C.sub.4 H.sub.9, n-C.sub.6 H.sub.13, which may be optionally substituted by OH, OCH.sub.3, OC.sub.2 H.sub.5, COOH, SO.sub.3 H, OSO.sub.3 H, CN, Cl, or F.
Examples of the substituents in substituted C.sub.1 -C.sub.4 -alkyl and C.sub.1 -C.sub.4 -alkoxy, groups are OH, OCH.sub.3, OC.sub.2 H.sub
REFERENCES:
patent: 4780107 (1988-10-01), Sawamoto et al.
patent: 5227475 (1993-07-01), Buch et al.
Helmling Walter
Reiher Uwe
Crall Hugh C.
Datlow Philip I.
Hoechst Celanese Corporation
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