Organic compounds -- part of the class 532-570 series – Organic compounds – Heterocyclic carbon compounds containing a hetero ring...
Patent
1997-05-09
1999-10-05
Rotman, Alan L.
Organic compounds -- part of the class 532-570 series
Organic compounds
Heterocyclic carbon compounds containing a hetero ring...
546256, 5462761, 5462771, 503223, 8603, 428913, 428914, C07D40104, C07D41704, B41M 524, B41M 526
Patent
active
059626917
DESCRIPTION:
BRIEF SUMMARY
The present invention relates to novel pyridone dyes of the formula I ##STR2## where X is nitrogen or CH, -C.sub.4 -alkanoyl and and may be interrupted by from 1 to 3 ether oxygen atoms, or is unsubstituted or substituted phenyl or a radical of the formula NE.sup.1 E.sup.2, where E.sup.1 and E.sup.2 are identical or different and, independently of one another, are each hydrogen, C.sub.1 -C.sub.13 -alkyl which is unsubstituted or substituted and may be interrupted by from 1 to 3 ether oxygen atoms, or are each C.sub.5 -C.sub.7 -cycloalkyl, unsubstituted or substituted phenyl, unsubstituted or substituted pyridyl, unsubstituted or substituted C.sub.1 -C.sub.13 -alkanoyl, C.sub.1 -C.sub.13 -alkoxycarbonyl, unsubstituted or substituted C.sub.1 -C.sub.13 -alkylsulfonyl, C.sub.5 -C.sub.7 -cycloalkylsulfonyl, unsubstituted or substituted phenylsulfonyl, unsubstituted or substituted pyridylsulfonyl, unsubstituted or substituted benzoyl, pyridylcarbonyl or thienylcarbonyl or E.sup.1 and E.sup.2, together with the nitrogen atom linking them, are unsubstituted or C.sub.1 -C.sub.4 -alkyl-substituted succinimido, unsubstituted or C.sub.1 -C.sub.4 -alkyl-substituted phthalimido or a 5-membered or 6-membered saturated heterocyclic radical which may contain further heteroatoms, synthetic materials by means of the novel dyes.
JP-A-339 237/1993 describes the preparation of 1-alkyl-3-cyano-4-trifluoromethyl-6-hydroxypyrid-2-ones. Furthermore, JP-A-331 382/1993 and Bull. Chem. Soc. Japan 66 (1993), 1790-1794, disclose azodyes which have the abovementioned compound as a coupling component.
It is an object of the present invention to provide novel methine and azamethine dyes which have advantageous performance characteristics.
We have found that this object is achieved by the pyridone dyes of formula I which are defined at the outset.
R.sup.1 is a 5-membered or 6-membered carbocyclic or heterocyclic, preferably aromatic, radical which is unsubstituted or substituted and may be benzofused.
R.sup.1 may be derived, for example, from components from the benzene, indole, quinoline, naphthalene, pyrrole, thiazole, benzimidazole, benzothiazole, thiophene or pyridine series.
Important radicals R.sup.1 are, for example, those of the formulae IIa to IIj ##STR3## where n is 0 or 1, from 1 to 3 ether oxygen atoms, or is hydroxyl, C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -alkylsulfonylamino, C.sub.1 -C.sub.4 -mono- or dialkylaminosulfonyl-amino or a 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.13 -alkyl which may be interrupted by from 1 to 3 ether oxygen atoms, another, are each hydrogen or C.sub.1 -C.sub.13 -alkyl which is unsubstituted or substituted and may be interrupted by from 1 to 3 ether oxygen atoms, or are each C.sub.3 -C.sub.4 -alkenyl, C.sub.5 -C.sub.7 -cycloalkyl, phenyl or tolyl or, together with the nitrogen atom linking them, are a 5-membered or 6-membered saturated heterocyclic radical which may contain further heteroatoms, substituted phenyl, unsubstituted or substituted benzyl, C.sub.5 -C.sub.7 -cycloalkyl, thienyl, hydroxyl, C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -alkylthio or C.sub.1 -C.sub.13 -monoalkylamino.
All alkyl or alkenyl groups occurring in the abovementioned formulae may be either straight-chain or branched.
Where substituted alkyl radicals occur in the abovementioned formulae, unless stated otherwise, suitable substituents may be, for example, cyclohexyl, unsubstituted or substituted phenyl, C.sub.1 -C.sub.8 -alkanoyloxy, C.sub.1 -C.sub.8 -alkylaminocarbonyloxy, C.sub.1 -C.sub.8 -alkoxy-carbonyl, C.sub.1 -C.sub.8 -alkoxycarbonyloxy, where the alkyl chain of the three last mentioned radicals may be interrupted by from 1 to 3 ether oxygen atoms, and may be substituted by phenyl or phenoxy, and cyclohexyloxy, phenoxy, halogen, hydroxyl or cyano. The alkyl radicals have as a rule 1 or 2 substituents.
Where alkyl radicals which are interrupted by ether oxygen atoms occur in the abovementioned formulae, preferred alkyl radicals are those which are i
REFERENCES:
patent: 5079365 (1992-01-01), Sens et al.
patent: 5132438 (1992-07-01), Bach, et al
patent: 5147845 (1992-09-01), Sens et al.
patent: 5376150 (1994-12-01), Lange et al.
Matsui et al., Bulletin of the Chemical Society of Japan, vol. 66, (6) pp. 1790-1794, Jun. 1993.
Bulletin of the chemical society of Japan, Vol. 66, 1993.
Etzbach Karl-Heinz
Schmidt Andreas Johann
Sens Rudiger
BASF - Aktiengesellschaft
Rotman Alan L.
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