JPH0368623A - Production of anthracene polyester - Google Patents

Abstract

PURPOSE:To obtain stably a highly viscous anthracene polyester by reacting an anthraquinone compound with a reducing agent at a specified temperature or below. CONSTITUTION:An anthracene polyester is obtained by reacting an anthraquinone compound with a reducing agent at a temperature <=50 deg.C. According to this production process a highly viscous anthracene polyester can be stably obtained. Therefore a nonsagging coating fluid can be stably obtained when it is applied to e.g. an electrophotographic photoreceptor.

Description

DETAILED DESCRIPTION OF THE INVENTION [Industrial Application Field] The present invention relates to a method for producing anthracene polyester using an anthraquinone compound as a raw material.

[Conventional technology]

When producing anthracene polyesters, anthraquinone compounds are treated with reducing agents such as sodium dithionite and dicarboxylic acid civalide.

For example, it is known that anthracene polyester can be obtained by reacting with azelaic acid dichloride (
(Refer to Japanese Patent Publication No. 60-3408) [Problems to be Solved by the Invention] However, although it is possible to obtain anthracene polyester with a certain viscosity with the conventional production method, it is difficult to stably obtain anthracene polyester with a high viscosity. The problem was that I couldn't do it. For example, if this anthracene-based polyester is applied to an electrophotographic photoreceptor, an intrinsic viscosity of about 1.0 or higher is required in order to create a coating solution that does not cause dripping, but conventional manufacturing methods However, it has not been possible to stably obtain such a high viscosity anthracene polyester.

This invention was made in view of the above points, and
An object of the present invention is to provide a novel method for producing anthracene polyester that can stably obtain anthracene polyester having a high viscosity of about 1.0 or more.

[Means to solve the problem]

According to the present invention, the above problems are solved by a production method in which an anthraquinone compound is reacted with a reducing agent at a temperature of 50° C. or lower.

[Effect]

In the conventionally known technology, regarding the control of the reaction temperature, there is only qualitative knowledge regarding the reactivity of dicarboxylic acid sybaride with water, and there is no need to particularly control the reaction temperature in other respects. It has been said that there is no such thing.

However, the inventors of the present invention focused on the reduction temperature of the anthraquinone compound and found that there is a significant difference in the intrinsic viscosity of the anthracene polyester produced depending on the reduction temperature of the anthraquinone compound. By setting this reduction temperature to 50° C. or lower, it becomes possible to stably obtain a high viscosity anthracene polyester.

〔Example〕

Examples of the present invention are shown below, but the present invention is not limited to these examples.

Example 1 104 g of anthraquinone, 348 g of sodium dithionite, 400 g of sodium hydroxide, and 20 g of trioctylmethylammonium chloride
was added to water in Step 51, and stirred while maintaining the liquid temperature at 50°C until dissolved. Thereafter, the reaction solution was cooled to 15° C., and a tetrachloroethane solution of 21 containing 124 g of azelaic acid dichloride was added to the reaction solution, followed by vigorous stirring. After stirring for 15 minutes, the reaction solution was allowed to stand still.2
Separated into layers. Separate the layers, take out the lower organic layer, and
When the mixture was poured into acetone (No. 1), white fine particles precipitated and precipitated. This precipitate was collected by filtration, washed repeatedly with water and acetone, and then vacuum dried to obtain a white powder. The intrinsic viscosity of this polymer was measured and was 1.03 (30
It was found to be a polymer with an extremely high intrinsic viscosity (°C in tetrachloroethane).

Comparative Example 1 A polymer was produced in the same manner as in Example 1, except that the melting temperature of anthraquinone and the like was set to 52°C. The intrinsic viscosity of this polymer was measured to be 0.85 (30℃
(in tetrachloroethane) and exhibited insufficient intrinsic viscosity.

Example 2 A polymer was produced in the same manner as in Example 1, except that 134 g of 2,6-dimethoxydianthraquinone was used instead of anthraquinone. The intrinsic viscosity of this polymer was measured to be 1.15 (in tetrachloroethane at 30°C).
The polymer was found to have extremely high intrinsic viscosity.

Example 3 A polymer was produced in the same manner as in Example 1, except that 148 g of 2,6-jethoxyanthraquinone was used instead of anthraquinone. When the intrinsic viscosity of this polymer was measured, it was found that the polymer had an extremely high intrinsic viscosity of 1.21 (in tetrachloroethane at 30° C.).

Example 4 A polymer was produced in the same manner as in Example 1, except that 176 g of dodecanoic acid dichloride was used instead of azelaic acid dichloride. When the intrinsic viscosity of this polymer was measured, it was found to be a polymer with an extremely high intrinsic viscosity of 1.32 (in tetrachloroethane at 30° C.).

Example 5 A polymer was produced in the same manner as in Example 1, except that 134 g of 2,6-dimethoxydianthraquinone was used instead of anthraquinone, and 176 g of dodecanoic acid dichloride was used instead of azelaic acid dichloride. The intrinsic viscosity of this polymer was measured to be 1.45 (30
It was found to be a polymer with an extremely high intrinsic viscosity (°C in tetrachloroethane).

〔Effect of the invention〕

Claims (1)

[Claims] 1) A method for producing anthracene polyester, which comprises reacting an anthraquinone compound with a reducing agent at a temperature of 50° C. or lower.