Organic compounds -- part of the class 532-570 series – Organic compounds – Azo
Patent
1997-01-22
1998-08-04
Powers, Fiona T.
Organic compounds -- part of the class 532-570 series
Organic compounds
Azo
534765, 534769, 534795, 502227, 428195, 428913, 428914, C09B 29033, C09B 2936, B41M 538
Patent
active
057895600
DESCRIPTION:
BRIEF SUMMARY
This application is a 371 of PCT/EP95/02866 filed Jul. 20, 1995.
The present invention relates to novel azo dyes of the formula I ##STR2## where
R.sup.1 and R.sup.2 are independently of each other C.sub.1 -C.sub.10 -alkyl with or without substitution by cyano, hydroxyl, halogen, C.sub.1 -C.sub.4 -alkanoyloxy, C.sub.1 -C.sub.4 -alkoxycarbonyl, C.sub.1 -C.sub.4 -alkoxycarbonyloxy or phenyl and with or without interruption by from 1 to 4 oxygen atoms in ether function, C.sub.5 -C.sub.7 -cycloalkyl, C.sub.3 -C.sub.4 -alkenyl, unsubstituted or C.sub.1 -C.sub.4 -alkyl-, C.sub.1 -C.sub.4 -alkoxy- or halogen-substituted phenyl, or R.sup.1 and R.sup.2 are together with the nitrogen atom joining them together a 5- or 6-membered saturated heterocyclic radical with or without further hetero atoms,
R.sup.3 is tert-butyl or tert-pentyl, and
D is a radical of a diazo component of the aniline series or the series of the aromatic heterocyclic amines, dyeing or printing synthetic materials.
EP-A-441 208 discloses azo dyes with a 2-aminothiazole as coupling component.
It is an object of the present invention to provide novel azo dyes which have advantageous application properties in the dyeing or printing of textile materials or in thermal dye transfer.
We have found that this object is achieved by the azo dyes of the formula I defined at the beginning.
Emphasis is given to azo dyes of the formula I where D is derived from a diazo component of the aniline series or from an amine of the pyrrole, thiophene, pyrazole, thiazole, isothiazole, triazole, thiadiazole, benzothiophene, benzothiazole, benzisothiazole, pyridothiophene, pyrimidothiophene or thienothiophene series.
Suitable radicals D conform for example to the formula ##STR3## where
L.sup.1 is nitro, cyano, C.sub.1 -C.sub.6 -alkanoyl, benzoyl, C.sub.1 -C.sub.6 -alkoxycarbonyl, C.sub.1 -C.sub.8 -alkylsulfonyl, substituted or unsubstituted phenylsulfonyl or a radical of the formula --CH.dbd.T, where T is hydroxyimino, C.sub.1 -C.sub.4 -alkoxyimino or a radical of an acidic-CH compound H.sub.2 T,
L.sup.2 is hydrogen, C.sub.1 -C.sub.6 -alkyl, halogen, hydroxyl, mercapto, unsubstituted or phenyl- or C.sub.1 -C.sub.4 -alkoxy-substituted C.sub.1 -C.sub.6 -alkoxy, substituted or unsubstituted phenoxy, unsubstituted or phenyl-substituted C.sub.1 -C.sub.8 -alkylthio, substituted or unsubstituted phenylthio, C.sub.1 -C.sub.9 -alkylsulfonyl or substituted or unsubstituted phenylsulfonyl,
L.sup.3 is cyano, C.sub.1 -C.sub.6 -alkoxycarbonyl or nitro,
L.sup.4 is hydrogen, C.sub.1 -C.sub.6 -alkyl or phenyl,
L.sup.5 is C.sub.1 -C.sub.6 -alkyl or phenyl,
L.sup.6 is hydrogen, cyano, nitro, C.sub.1 -C.sub.6 -alkoxycarbonyl, C.sub.1 -C.sub.6 -alkanoyl, thiocyanato or halogen,
L.sup.7 is nitro, cyano, C.sub.1 -C.sub.6 -alkanoyl, benzoyl, C.sub.1 -C.sub.6 -alkoxycarbonyl, C.sub.1 -C.sub.8 -alkylsulfonyl, substituted or unsubstituted phenylsulfonyl or a radical of the formula --CH.dbd.T, where T is as defined above,
L.sup.8 is hydrogen, C.sub.1 -C.sub.6 -alkyl, substituted or unsubstituted phenyl, cyano, halogen, unsubstituted or phenyl- or C.sub.1 -C.sub.4 -alkoxy-substituted C.sub.1 -C.sub.8 -alkoxy, unsubstituted or phenyl-substituted C.sub.1 -C.sub.8 -alkylthio, substituted or unsubstituted phenylthio, C.sub.1 -C.sub.8 -alkylsulfonyl, substituted or unsubstituted phenylsulfonyl or C.sub.1 -C.sub.6 -alkoxycarbonyl,
L.sup.9 is cyano, unsubstituted or phenyl- or C.sub.1 -C.sub.4 -alkoxy- substituted C.sub.1 -C.sub.6 -alkyl, unsubstituted or phenyl-substituted C.sub.1 -C.sub.8 -alkoxy, unsubstituted or phenyl-substituted C.sub.1 -C.sub.8 -alkylthio, substituted or unsubstituted phenyl, thienyl, C.sub.1 -C.sub.4 -alkylthienyl, pyridyl or C.sub.1 -C.sub.4 -alkylpyridyl or, together with L.sup.6, a fused benzo radical,
L.sup.10 is phenyl or pyridyl,
L.sup.11 is trifluoromethyl, nitro, C.sub.1 -C.sub.6 -alkyl, phenyl, unsubstituted or phenyl-substituted C.sub.1 -C.sub.8 -alkylthio or C.sub.1 -C.sub.6 -dialkylamino,
L.sup.12 is unsubstituted or acetyloxy-substituted C.sub.1 -C.sub.6 -alkyl, phenyl, u
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Etzbach Karl-Heinz
Sens Rudiger
BASF - Aktiengesellschaft
Powers Fiona T.
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