Journal
DYES AND PIGMENTS
Volume 76, Issue 1, Pages 147-157Publisher
ELSEVIER SCI LTD
DOI: 10.1016/j.dyepig.2006.07.029
Keywords
heterocyclic; disazo dyes; pyrazole; pyrazolone; pyridone; thiazole; benzothiazole; solvent effect
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Heterocyclic amines were diazotized and coupled with 3-aminocrotononitrile to give the 2-hetarylhydrazone-3-ketiminobutyronitrile (la-le) which can react with hydrazine hydrate and phenylhydrazine to afford the corresponding 5-amino-3-methyl-4-hetarylazo-1H-pyrazoles and 5-amino-3-methyl-4-hetarylazo-1-phenylpyrazoles (2a-2j), respectively. Then, some novel disazo dyes 3a-3j and 4a-4j were synthesized by diazotisation of 5-amino-3-methyl-4-hetarylazo-1H-pyrazoles and 5-amino-3-methyl-4-hetarylazo-1-phenylpyrazoles using nitrosyl sulphuric acid, coupling with 3-cyano-6-hydroxy-4-methyl-2-pyridone and 3-methyl- 1H-pyrazole-5-one. The dyes were characterized by elemental analysis and spectral methods and the solvatochromic behaviour of the dyes in various solvents was evaluated. Substituent, acid and base effects on the visible absorption maxima of the dyes were also reported. (C) 2006 Elsevier Ltd. All rights reserved.
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