PREPARATION OF SUBSTITUTED 1,2-NAPHTOQUINONE-(2)- DIAZIDE-4-SILFONATE ESTER AND USE THEREOF IN RADIATION-SENSITIVE MIXTURE

The invention relates to a process for preparing 1,2-naphthoquinone-(2)-diazide-4-sulfonic acid esters of the general formula I (I) which are substituted in at least one of the positions 5, 6, 7 or 8 by R=halogen, alkoxy groups or alkoxycarbonyl groups and in which X denotes an aryl group. The proce...

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Hauptverfasser: HERUBERUTO JIIGERU, JIIKUFURIITO SHIERAA
Format: Patent
Sprache:eng
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Zusammenfassung:The invention relates to a process for preparing 1,2-naphthoquinone-(2)-diazide-4-sulfonic acid esters of the general formula I (I) which are substituted in at least one of the positions 5, 6, 7 or 8 by R=halogen, alkoxy groups or alkoxycarbonyl groups and in which X denotes an aryl group. The process comprises steps in which a) suitably substituted beta -naphthol is nitrosated, b) sulfonation with alkali hydrogensulfite and acid in position 4 and reduction are carried out, c) the naphthalenesulfonic acid derivative is oxidized, d) the 1,2-naphthoquinone-4-sulfonic acid formed is reacted with toluenesulfonohydrazide in an organic solvent at temperatures from 20 DEG to 100 DEG C., e) the naphthoquinonediazide compound is converted with chlorosulfonic acid or chlorosulfonic acid/thionyl chloride into the sulfonyl chloride, and f) the sulfonyl chloride is condensed with a phenolic component, a purification of the respective intermediate product by reprecipitation or recrystallization being unnecessary. The process makes a simple technical procedure possible with good yield. The compounds prepared, in particular the 1,2-naphthoquinone-(2)-diazide-4-sulfonic acid esters substituted by 6-alkoxycarbonyl groups or by 7-alkoxy groups, are used as radiation-sensitive components in radiation-sensitive mixtures.