Organic compounds -- part of the class 532-570 series – Organic compounds – Azo
Patent
1994-09-30
1995-11-14
Richter, Johann
Organic compounds -- part of the class 532-570 series
Organic compounds
Azo
534575, 534630, 534765, 534766, 534768, 534769, 534774, 534791, 534795, 534599, C09B 29033, C09B 29042, C09B 6748, D06P 118
Patent
active
054667909
DESCRIPTION:
BRIEF SUMMARY
This is a 371 of application no. PCT /EP93/01043, filed Apr. 30, 1993 now patent no. WO93/23479.
The present invention relates to novel azo dyes of formula I ##STR3## where L.sup.1 is hydrogen, C.sub.1 -C.sub.8 -alkyl or phenyl, the other C.sub.1 -C.sub.8 -alkyl, which may be substituted and may be interrupted by 1 or 2 oxygen atoms in ether function, or together are a radical of the formula ##STR4## where n is 0, 1 or 2, Y.sup.1 and Y.sup.4 are identical or different and each is independently of the other hydrogen, hydroxymethyl, 1,2-dihydroxyethyl or a radical of the formula COO.sup..crclbar. M.sup..sym. or SO.sub.3 .crclbar.M.sym., Y.sup.2 and Y.sup.3 are identical or different and are each independently of the other halogen or hydroxymethyl, and M.sym. is the equivalent of a cation, or 2 oxygen atoms in ether function and may be substituted, substituted or unsubstituted phenyl, halogen, C.sub.1 -C.sub.8 -alkoxy, substituted or unsubstituted phenoxy, C.sub.1 -C.sub.8 -alkylthio, C.sub.1 -C.sub.8 -alkylsulfonyl, substituted or unsubstituted phenylthio, substituted or unsubstituted phenylsulfonyl, C.sub.1 -C.sub.8 -alkoxycarbonyl, C.sub.3 -C.sub.6 -alkenyloxycarbonyl or phenoxycarbonyl, -C.sub.8 -alkoxycarbonyl, C.sub.3 -C.sub.6 -alkenyloxycarbonyl, phenoxycarbonyl, C.sub.1 -C.sub.8 -alkanoyl, benzoyl, carbamoyl, mono- or di(C.sub.1 -C.sub.4 -alkyl)carbamoyl, phenylcarbamoyl, C.sub.1 -C.sub.8 alkylsulfonyl or substituted or unsubstituted phenylsulfonyl, and dyes for dyeing or printing textile materials.
DE-A-3 529 831, GB-A-2 071 684, DE-A-2 818 101, EP-A-362 637, DE-A-3 906 066, EP-A-201 896 and EP-A-390 666 disclose azo dyes which are similar to those of the formula I. They have a carbonyl group in ring position 5 of the thiophene or thiazole ring. It has been found that the solubility of these dyes leaves something to be desired. Nor is their application property profile satisfactory in every respect.
It is an object of the present invention to provide novel azo dyes which are free of the abovementioned defects.
We have found that this object is achieved by the azo dyes of the formula I defined at the beginning.
In the azo dyes of the formula I, K can be for example the radical of a coupling component of the aniline, aminothiazole, pyrazole, diaminopyridine, hydroxypyridone or quinoline series.
Emphasis is given to azo dyes of the formula I where K is a radical of the formula ##STR5## where R.sup.1 and R.sup.2 are identical or different and each is independently of the other hydrogen, substituted or unsubstituted C.sub.1 -C.sub.8 -alkyl, which may be interrupted by 1 or 2 oxygen atoms in ether function, C.sub.5 -C.sub.7 -cycloalkyl or C.sub.3 -C.sub.6 -alkenyl, which may be substituted by halogen, in particular by chlorine or bromine, C.sub.1 -C.sub.8 -alkylsulfonylamino, substituted or unsubstituted C.sub.1 -C.sub.8 -alkanoylamino or benzoylamino, phenyl or thienyl, oxygen atoms in ether function, benzyl, C.sub.5 -C.sub.7 -cycloalkyl, C.sub.3 -C.sub.6 -alkenyl or substituted or unsubstituted phenyl independently of the others substituted or unsubstituted C.sub.1 -C.sub.8 -alkyl which may be interrupted by 1 or 2 oxygen atoms in ether function, C.sub.5 -C.sub.7 -cycloalkyl, substituted or unsubstituted phenyl, C.sub.3 -C.sub.6 -alkenyl, substituted or unsubstituted benzoyl, C.sub.1 -C.sub.8 -alkanoyl, C.sub.1 -C.sub.8 -alkylsufonyl or substituted or unsubstituted phenylsulfonyl, or R.sup.11 and R.sup.12 are together with the nitrogen atom joining them together a 5- or 6-membered saturated heterocyclic radical, which may contain further hereto atoms, and
Any alkyl or alkenyl appearing in the abovementioned formulae may be straight-chain or branched.
Any substituted phenyl appearing in the above-mentioned formulae may have as substituents for example C.sub.1 -C.sub.4 -alkyl, chlorine, bromine, nitro, C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -alkoxycarbonyl, carboxyl or hydroxysulfonyl. The number of substituents in substituted phenyl is in general from 1 to 3.
Any substituted alkyl appearing in the abo
REFERENCES:
patent: 4395544 (1983-07-01), Egli
patent: 5079365 (1992-01-01), Sens et al.
patent: 5132411 (1992-07-01), Egli et al.
Degen Helmut
Gruettner-Merten Sabine
Lange Arno
Reichelt Helmut
BASF - Aktiengesellschaft
Powers Fiona
Richter Johann
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