Triazolopyridine dyes

Details Triazolopyridine dyes Triazolopyridine dyes

1996-08-19

1997-04-01

Powers, Fiona T.

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

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

544127, 8471, 503227, C09B 2304, C09B 5500, B41M 538

Patent

active

056167105

DESCRIPTION:

BRIEF SUMMARY
The present invention relates to novel triazolopyridine dyes of the formula I ##STR3## where A is nitrogen, -alkyl which is unsubstituted or substituted and can be interrupted by 1 to 4 oxygen atoms in ether functionality, unsubstituted or substituted phenyl, mercapto or unsubstituted or substituted C.sub.1 -C.sub.20 -alkylthiol, ##STR4## where R.sup.2 is a 5- or 6-membered carbocyclic or heterocyclic radical which can be benzo-fused, atom in ether functionality, C.sub.1 -C.sub.4 -haloalkyl, C.sub.1 -C.sub.4 -alkoxycarbonyl or unsubstituted or substituted phenyl, benzothiazolyl or R.sup.3 and R.sup.4 together are the remainder of a fused-on benzene ring and ##STR5## where L is in each case C.sub.1 -C.sub.8 -alkyl which may be interrupted by 1 or 2 oxygen atoms in ether functionality, ##STR6## the two radicals A and E may also be mutually interchanged, and to a process for the thermal transfer of these dyes.
U.S. Pat. No. 5,079,365 discloses triazolopyridine dyes which are based on a different ring system.
It is an object of the present invention to provide novel triazolopyridine dyes with a different chemical structure. They should be easy to prepare.
We have found that this object is achieved by the triazolopyridine dyes of the formula I defined at the outset.
The dyes of the formula I may occur in a plurality of tautomeric forms, all of which are embraced by the claims. For example, the compounds with R.sup.3 =methyl and R.sup.5 =oxygen may occur in the following tautomeric forms, inter alia: ##STR7## R.sup.2 is a 5- or 6-membered carbocyclic or heterocyclic radical which is unsubstituted or substituted and can be benzo-fused.
R.sup.2 radicals may be derived, for example, from components from the benzene, indole, quinoline, aminonaphthalene, pyrrole, aminothiazole, benzimidazole, benzothiazole, aminothiophene or diaminopyridine series.
Examples of important R.sup.2 radicals are those of the formulae IIa to IIj ##STR8## where n is 0 or 1, or 2 oxygen atoms in ether functionality, hydroxyl, C.sub.1 -C.sub.4 -alkoxy, especially methoxy or ethoxy, formylamino, C.sub.1 -C.sub.4 -alkylsulfonylamino, C.sub.1 -C.sub.4 -mono- or dialkylaminosulfonylamino or the radical --NHCOZ.sup.7 or --NHCO.sub.2 Z.sup.7 where Z.sup.7 is phenyl, benzyl, tolyl or C.sub.1 -C.sub.8 -alkyl which may be interrupted by 1 or 2 oxygen atoms in ether functionality, -C.sub.4 -alkoxy, especially methoxy or ethoxy, of one another, hydrogen, C.sub.1 -C.sub.8 -alkyl which is unsubstituted or substituted and may be interrupted by one or two oxygen atoms in ether functionality, C.sub.3 -C.sub.4 -alkenyl, C.sub.5 -C.sub.7 -cycloalkyl, unsubstituted or substituted phenyl or, together with the nitrogen atom connecting them, a five- or six-membered saturated heterocyclic radical which may contain further hetero atoms, substituted phenyl, unsubstituted or substituted benzyl, cyclohexyl, thienyl, hydroxyl, C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -alkylthio or C.sub.1 -C.sub.8 -monoalkylamino.
All the alkyl and alkenyl groups occurring in the above mentioned formulae can be either straight-chain or branched.
Examples of suitable substituents in substituted alkyl radicals in the abovementioned formulae are unsubstituted or substituted phenyl, unsubstituted or substituted phenoxy, carboxyl, C.sub.1 -C.sub.20 -alkoxycarbonyl whose alkyl chain may be interrupted by 1 to 4 oxygen atoms in ether functionality and substituted by phenyl or phenoxy, or cyano, C.sub.1 -C.sub.6 -alkanoyloxy, C.sub.1 -C.sub.4 alkylaminocarbonyloxy or C.sub.1 -C.sub.4 -alkoxycarbonyloxy, where in the latter case the alkoxy group may be substituted by phenyl or C.sub.1 -C.sub.4 -alkoxy. Moreover, as a rule, the alkyl radicals have 1 or 2 substituents.
Where the abovementioned formulae contain alkyl radicals which are interrupted by oxygen atoms in ether functionality, the preferred alkyl radicals are interrupted by 1 or 2 oxygen atoms in ether functionality.
Examples of suitable substituents for substituted phenyl radicals in the abovementioned formulae are C.sub.1 -C.sub.4 -al

REFERENCES:
patent: 5079365 (1992-01-01), Sens et al.
patent: 5147845 (1992-09-01), Sens et al.
patent: 5376150 (1994-12-01), Lange et al.
patent: 5389596 (1995-02-01), Etzbach et al.
patent: 5489312 (1996-02-01), Etzbach et al.

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