Azo dyestuffs containing a diazo component from the aniline seri

Details Azo dyestuffs containing a diazo component from the aniline seri Azo dyestuffs containing a diazo component from the aniline seri

1996-02-14

1997-03-04

Powers, Fiona T.

Organic compounds -- part of the class 532-570 series

Organic compounds

Azo

8922, 8924, 8532, C09B 2936, D06P 352

Patent

active

056080417

DESCRIPTION:

BRIEF SUMMARY
This application is a 371 of PCT/EP94/02756 filed Aug. 19, 1994.


DESCRIPTION

The present invention relates to novel triazolopyridine azo dye-stuffs of the formula I ##STR2## where
A is nitrogen,
E is a radical of the formula C---R.sup.1, where R.sup.1 is C.sub.1 -C.sub.20 -alkyl, which is unsubstituted or substituted and can be interrupted by 1 to 4 ether oxygen atoms, or is unsubstituted or substituted phenyl, mercapto or unsubstituted or substituted C.sub.1 -C.sub.20 -alkylthio,
one of the two radicals R.sup.2 and R.sup.4 is cyano, carbamoyl, carboxyl or C.sub.1 -C.sub.4 -alkoxycarbonyl and the other is a radical of the formula D--N.dbd.N--, where D is a radical of a diazo component from the aniline series,
R.sup.3 is C.sub.1 -C.sub.4 -alkyl which may also be interrupted by an ether oxygen atom, or phenyl and
R.sup.5 is hydroxyl, mercapto, the radical --NY.sup.1 Y.sup.2, where Y.sup.1 and Y.sup.2 are identical or different and independently of one another in each case are hydrogen or C.sub.1 -C.sub.4 -alkyl or, together with the nitrogen atom bonding them, are a 5- or 6-membered saturated heterocyclic radical, or the radical of a CH-acidic compound, D--N.dbd.N--, the two radicals A and E can also be exchanged for one another,
Phenylazo dyestuffs which contain a coupling component from the 1,2,4-triazolo[1,5-a]pyridine series have already been disclosed in DE-A-4 020 768. The phenylazo group is located in ring position 4 of the heterocyclic system. However, it has been shown that these dyestuffs still have deficiencies in their applicational properties.
It is an object of the present invention to provide novel azo dyestuffs containing a coupling component from the triazolopyridine series and a diazo component from the aniline series and which have a high fastness to dry heat setting and pleating, high brilliance and high dyeing power.
We have found that this object is achieved by the triazolopyridine azo dyestuffs of the formula I described in greater detail at the beginning.
The dyestuffs of the formula I can occur in two or more tautomeric forms, which are all covered by the patent claim. For example, the dyestuffs where R.sup.2 .dbd.D--N.dbd.N-- can occur, inter alia, in the following tautomeric forms: ##STR3##
If in formula I substituted C.sub.1 -C.sub.2 O-alkyl radicals occur, suitable substituents can be e.g. unsubstituted or substituted phenyl, unsubstituted or substituted phenoxy, carboxyl or C.sub.1 -C.sub.20 -alkoxycarbonyl whose alkyl chain may be interrupted by 1 to 4 ether oxygen atoms and can be substituted by phenyl or phenoxy. The alkyl radicals here as a rule have 1 or 2 substituents.
If in formula I alkyl radicals occur which are interrupted by ether oxygen atoms, those alkyl radicals are preferred which are interrupted by 1 or 2 ether oxygen atoms.
If in formula I substituted phenyl radicals occur, suitable substituents can be e.g. C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy, halogen, in this case in particular chlorine or bromine, nitro, cyano or carboxyl. The phenyl radicals here as a rule have 1 to 3 substituents.
If R.sup.5 in formula I is a radical of a CH-acidic compound, this radical can be derived e.g. from nitromethane, nitroethane or from compounds of the formulae IV to IX ##STR4## where
X.sup.1 is cyano, nitro, C.sub.1 -C.sub.4 -alkanoyl, benzoyl which is unsubstituted or substituted by C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy or halogen, C.sub.1 -C.sub.4 -alkylsulfonyl, phenylsulfonyl which is unsubstituted or substituted by C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy or halogen, carboxyl, C.sub.1 -C.sub.4 -alkoxycarbonyl, phenoxycarbonyl, carbamoyl, C.sub.1 -C.sub.4 -mono- or -dialkylcarbamoyl, phenylcarbamoyl which is unsubstituted or substituted by C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy or halogen, phenyl which is unsubstituted or substituted by C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy, halogen or nitro, benzothiazol-2-yl, benzimidazol-2-yl, 5-phenyl-1,3,4-thiadiazol-2-yl or 2-hydroxy-quinoxalin-3-yl,
X.sup.2 is C.sub.1 -C.sub.4

REFERENCES:
patent: 5147845 (1992-09-01), Sens et al.

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