Process for preparing substituted 1,2-naphthoquinone-(2)-diazide-4-sulfonic acid esters and their use in a radiation-sensitive mixture

US5082932A · kind A · utility

Assignee

• Hoechst GmbH · DE

Inventors

• Herbert Siegel · Hofheim, DE
• Siegfried Scheler · Wiesbaden, DE

Key dates

• Filing date: Nov 3, 1989
• Grant date: Jan 21, 1992
• Expiry date: Nov 3, 2009

Classification

• Technology area (CPC G): Physics
• CPC primary: G03F7/022
• WIPO field: Organic fine chemistry
• WIPO sector: Chemistry

Abstract

The invention relates to a process for preparing 1,2-naphthoquinone-(2)-diazide-4-sulfonic acid esters of the general formula I ##STR1## 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 PA0 a) suitably substituted .beta.-naphthol is nitrosated, PA0 b) sulfonation with alkali hydrogensulfite and acid in position 4 and reduction are carried out, PA0 c) the naphthalenesulfonic acid derivative is oxidized, PA0 d) the 1,2-naphthoquinone-4-sulfonic acid formed is reacted with toluenesulfonohydrazide in an organic solvent at temperatures from 20.degree. to 100.degree. C., PA0 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-sul…