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Preparation method of 1-[4-(thiophenyl)phenyl]-1,2-octyldione-2-(O-benzoyloxime)

A technology of benzoyl oxime and octane dione, which is applied to the production of 1-[4-(phenylthio)phenyl]-1,2-octanedione-2-(O-benzoyl oxime) In the field of preparation, it can solve the problems of low sensitivity, heavy pollution, poor solubility, etc., and achieve the effect of avoiding the reaction between solvent and acid chloride, increasing the reaction yield, and promoting the complete reaction

Inactive Publication Date: 2014-08-13
TIANJIN JIURI NEW MATERIALS CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The traditional methods of making color photoresist mainly include dyeing method and electrodeposition method. These traditional methods all use metal chromium, which is highly toxic and pollutes heavily. Moreover, these methods cannot meet the production of large-screen LCDs. At present, more advanced pigments Dispersion method, simple operation process, excellent color characteristics, heat resistance, and light resistance, has gradually become the mainstream process for making color photoresist, and the production of pigment photoresist is the key technology of pigment dispersion method
[0003] Photoinitiators are one of the important raw materials for making photoresists. Traditional photoinitiators include: benzoin, biphenyl ketal, α, α-dialkoxyacetophenone, α-hydroxyalkylphenone Classes, α-aminoalkylphenones, acylphosphine oxides, benzophenone / amines, etc., generally have disadvantages such as low sensitivity, poor solubility, and poor storage stability, which will directly affect the color light. The properties such as transparency and heat resistance cannot satisfy the production of high-quality pigment photoresist
[0004] In 1904, Awernerl reported the photochemical properties of oxime esters for the first time. In 1970, oxime esters began to be used as photoinitiators. Among them, the oxyacyl oxime ester photoinitiator Quantacure PDO (Formula I) was widely used commercially. However, due to its poor thermal stability, it was gradually eliminated

Method used

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  • Preparation method of 1-[4-(thiophenyl)phenyl]-1,2-octyldione-2-(O-benzoyloxime)

Examples

Experimental program
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Effect test

Embodiment 1

[0023] Example 1: Preparation of 1-[4-(phenylthio)phenyl]-1,2-octanedione-2-(O-benzoyl oxime)

[0024] 1) Dissolve 37.2g of diphenyl sulfide in 140ml of dichloroethane, cool to about 0°C, add 29.2g of aluminum trichloride, keep the temperature, stir vigorously, slowly add 35.8g of n-octanoyl chloride dropwise, 3h After dropping, keep warm for reaction, monitor the reaction by TLC or liquid chromatography, after the reaction, pour the reaction solution into 200g 2% dilute hydrochloric acid ice water for hydrolysis, stir for 0.5h, let stand, separate layers, discard the water phase, organic The phase was adjusted to neutrality with 2% NaOH solution, separated, washed with water, and the organic phase was dried. The purity of 1-(4-phenylthio-phenyl)-oct-1-one in the organic phase was 98.1%, and the solvent was recovered first. Purified by low-pressure distillation, collected 217~220℃ / 3mmHg fraction 56.9g, product purity 99.2%, yield 91%;

[0025] 2) Dissolve hydrogen chloride in...

Embodiment 2

[0027]Example 2: Preparation of 1-[4-(phenylthio)phenyl]-1,2-octanedione-2-(O-benzoyl oxime)

[0028] 1) Dissolve 37.2g of diphenyl sulfide in 140ml of dichloroethane, cool to about 0°C, add 29.2g of aluminum trichloride, keep the temperature, stir vigorously, slowly add 35.8g of n-octanoyl chloride dropwise, 3h After dropping, keep warm for reaction, monitor the reaction by TLC or liquid chromatography, after the reaction, pour the reaction solution into 200g 2% dilute hydrochloric acid ice water for hydrolysis, stir for 0.5h, let stand, separate layers, discard the water phase, organic The phase was adjusted to neutrality with 2% NaOH solution, separated, washed with water, and the organic phase was dried. The purity of 1-(4-phenylthio-phenyl)-oct-1-one in the organic phase was 98.2%;

[0029] 2) Dissolve hydrogen chloride in an organic solvent to obtain a THF solution of hydrogen chloride, take 400g of THF solution of hydrogen chloride, wherein the content of hydrogen chlor...

Embodiment 3

[0031] Example 3: Preparation of 1-(4-phenylthio-phenyl)-octyl-1,2-dione-2-oxime

[0032] Take 20g of 1-(4-phenylthio-phenyl)-oct-1-one prepared according to step 1 of Example 1, 200g THF, 100g concentrated hydrochloric acid, stir for 0.5h, control the temperature below 10°C and add dropwise 12g of isoamyl nitrite, after 0.5h drop. Continue to react at 10°C for 3h. Concentrate THF under low pressure, control the temperature below 50°C, wash and beat to neutral after concentration, add 40g of petroleum ether solvent, cool to -15°C for suction filtration, recrystallize with 40g of petroleum ether, and dry to obtain 9.8g, yield 45%, purity 98.0%.

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Abstract

The invention relates to a preparation method of 1-[4-(thiophenyl)phenyl]-1,2-octyldione-2-(O-benzoyloxime), which is implemented by carrying out Friedel-Crafts acylation reaction, nitrosification reaction and benzoyl chloride reaction on phenyl sulfide, n-caprylyl chloride and benzoyl chloride used as raw materials. The preparation method has the advantages of high yield, low cost and environmental protection, and is easy to operate and suitable for industrialization.

Description

technical field [0001] The invention relates to a preparation method of 1-[4-(phenylthio)phenyl]-1,2-octanedione-2-(O-benzoyl oxime), in particular to 1-[4-( Phenylthio)phenyl]-1,2-octanedione-2-(O-benzoyl oxime) uses diphenyl sulfide, n-octanoyl chloride, and benzoyl chloride as raw materials, and undergoes acylation reaction, The three-step reaction of nitrosation reaction and reaction with benzoyl chloride, intermediates can be continuously reacted without purification and solvent replacement, and a preparation method with high yield, low cost, environmental protection, easy operation and suitable for industrialization is provided. Background technique [0002] Color photoresist is an important material for color filters. It is mainly composed of red, green and blue polymer materials. Benefiting from the increase in demand for LCD TVs and the continuous expansion of panel factories, the demand for color photoresist Continue to grow. The traditional methods of making col...

Claims

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Application Information

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IPC IPC(8): C07C323/47C07C319/20
Inventor 张齐武瑞王晓蒙李钰罗俊文程兵兵毛桂红徐新元赵国锋
Owner TIANJIN JIURI NEW MATERIALS CO LTD
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