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Fluorescent brightening agent and synthesis method of its mixture

The technology of a fluorescent whitening agent and a synthesis method is applied in the field of synthesis of fluorescent whitening agents and their mixtures, which can solve problems such as harsh reaction conditions, high production costs, and low product purity, and achieve safe reaction processes, reduced raw material costs, Good whitening effect

Inactive Publication Date: 2004-08-04
SHENYANG RES INST OF CHEM IND +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

This preparation method has harsh reaction conditions, low product purity, and harmful gases are produced during the synthesis of 4,4'-stilbene dicarboxylic acid, which is easy to cause harm to the environment
Introduced in U.S. Patent USP 4508903 the method that benzoxazole benzyl chloride synthesizes bisbenzoxazole stilbene derivatives under the effect of alkali, although overcome the shortcoming that conditions are harsh in the above-mentioned technique, three wastes amount is big, but Synthesize only symmetrical compounds
Chinese patent application CN 1315474A discloses a method for synthesizing symmetrical and asymmetrical bisbenzoxazole stilbene mixtures with benzoxazole benzyl chloride under the action of a base, and the product is successfully used for the fluorescence of synthetic or natural polymeric materials Whitening treatment; however, flammable and explosive sodium hydride still needs to be used in the synthesis process, and the production cost is high

Method used

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  • Fluorescent brightening agent and synthesis method of its mixture
  • Fluorescent brightening agent and synthesis method of its mixture
  • Fluorescent brightening agent and synthesis method of its mixture

Examples

Experimental program
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Effect test

example 1

[0028] 4,4'dicyano-stilbene is prepared according to the synthetic method in US 4519953;

[0029] Disperse 7.1g (0.031 mol) of 4,4'-dicyano-stilbene in 200ml of methanol, pass through dry hydrogen chloride gas to saturation, stir and react at room temperature for 50 hours, filter, and dry in vacuo to obtain stilbene - 11.0 g of 4,4'-bisiminomethyl ester hydrochloride.

[0030] 11.0 g (0.03 mol) of stilbene-4,4'-bisiminomethyl ester hydrochloride and 6.7 g (0.061 mol) of 2-aminophenol were added to 60 ml of methanol, followed by 40 ml of glacial acetic acid. Slowly heat up to about 70°C with stirring, and keep for 6 hours until the end of the reaction. Cool down to 40°C, vacuum filter, wash the filter cake with water and then dry it. 11.4 g of 4,4'-bis(benzoxazol-2-yl)stilbene was obtained.

example 2

[0032] 11.0g (0.03mol) stilbene-4,4'-bisimine methyl ester hydrochloride, 3.4g (0.031mol) 2-aminophenol, 3.9g (0.031mol) 4-methyl-2-amino Phenol was added to 60ml of methanol, followed by 40ml of glacial acetic acid. Slowly heat up to about 70°C with stirring, and keep for 6 hours until the end of the reaction. Cool down to 40°C, vacuum filter, wash the filter cake with water and then dry it. 11.9 g of the mixture were obtained.

[0033] The percentage of the mixture determined by liquid chromatography is:

[0034] 4-(Benzoxazol-2-yl)-4'-(5-methylbenzoxazol-2-yl)stilbene 49.5%; 4,4'-bis(benzoxazol-2- base) stilbene 22.7%; 4,4'-bis(5-methylbenzoxazol-2-yl) stilbene 27.8%.

example 3

[0036] 11.0g (0.03mol) stilbene-4,4'-bisiminomethyl ester hydrochloride, 2.6g (0.024mol) 4-methyl-2-aminophenol and 6.9g (0.042mol) 4-tert Butyl-2-aminophenol was added to 60ml of methanol, followed by 40ml of glacial acetic acid. Slowly heat up to about 70°C with stirring, and keep for 6 hours until the end of the reaction. Cool down to 40°C for vacuum suction filtration, wash the filter cake with water and then dry it. 13.7 g of the mixture were obtained.

[0037] Determine the percentage composition of the mixture with liquid chromatography as:

[0038] 4-(5-methylbenzoxazol-2-yl)-4'-(5-tert-butylbenzoxazol-2-yl)stilbene 44.0%; 4,4'-bis(5- Tolylbenzoxazol-2-yl)-stilbene 8.2%; 4,4'-bis(5-tert-butylbenzoxazol-2-yl)-stilbene 47.8%.

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Abstract

A fluorescent brightening agent is prepared from distyrene-4,4'-biimine hydrochloride and o-aminophenol or its derivative through condensation and ring-closing reaction in the medium of organic acid and alcohol to obtain bibenzoxazyl distyrene compound.

Description

technical field [0001] The invention relates to a method for synthesizing a fluorescent whitening agent and a mixture thereof. Background technique [0002] Usually, the method for synthesizing bisbenzoxazole stilbene compound is to use 4,4'-stilbene dicarboxylic acid as raw material, convert it into acid chloride and then condense with o-aminophenol derivatives into symmetrical compounds at high temperature, or respectively O-aminophenols with different substituents can be synthesized into asymmetric compounds through secondary condensation. Its specific preparation examples are described in detail in US Patent No. 4,282,355. This preparation method has harsh reaction conditions, low product purity, and harmful gas generated during the synthesis of 4,4'-stilbene dicarboxylic acid, which is likely to cause harm to the environment. Introduced in U.S. Patent USP 4508903 the method that benzoxazole benzyl chloride synthesizes bisbenzoxazole stilbene derivatives under the effe...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D413/10C09B57/00
Inventor 王景国徐薛伟李文胜竹百均张召来刘月中
Owner SHENYANG RES INST OF CHEM IND
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