Process for preparing perylene-3,4-dicarboxylic acid derivatives, the derivatives thus prepared and their use

US5650513A · kind A · utility

Assignee

• Ciba-Geigy · US

Inventors

• Heinz Langhals · Ottobrunn, DE
• Leonhard Feiler · Givisiez, CH

Key dates

• Filing date: Nov 10, 1994
• Grant date: Jul 22, 1997
• Expiry date: Nov 10, 2014

Classification

• Technology area (CPC C): Chemistry; Metallurgy
• CPC primary: C07C2603/54
• WIPO field: Organic fine chemistry
• WIPO sector: Chemistry

Abstract

Reacting the industrially readily available perylene-3,4,9,10-tetracarboxylic dianhydride (3) with specific primary amines in the presence of water gives perylene-3,4-dicarboxylic bisimides (2). Their hydrolysis affords the perylene-3,4-dicarboxylic anhydride on a preparative scale, and this anhydride is reacted with any primary amines to give likewise the corresponding imides 2. Condensation of the anhydride with diamines results in novel types of dyes, namely perylene-3,4-dicarboxamidines which have very good fastness properties. Also claimed are specific perylene-3,4-dicarboxylic diesters, perylene-3,4-dicarboxylic ester amides, perylene-3,4-dicarboxamidines and perylene-3,4-dicarbonyl derivatives, processes for preparing these compounds and their use. The compounds according to the invention are suitable, for example, as colorants for the mass coloration of high-molecular-weight organic material, for use in security printing, as fluorescent dyes for machine-readable markings, as laser dyes, and for preparing non-impact printing toners, color filters, organic photoreceptors, electroluminescence and photoluminescence elements or sun collectors and in specific substituted compound…