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Method for preparing dicyano-1,4phenylethenes asymmetric fluorescent whitener

A technology of fluorescent whitening agent and stilbene, which is used as an auxiliary agent in the fiber industry and in the field of plastics

Active Publication Date: 2012-05-30
ZHEJIANG TRANSFAR WHYYON CHEM
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] At present, there are few foreign reports on the synthesis of fluorescent whitening agent ER. European patent application EP0680947A2 has reported the application of phase transfer catalysis (PTC) technology to synthesize fluorescent whitening agent ER, but the reaction takes a long time, and the yield and purity are relatively low (71% yield, 87% purity). Considering the catalyst cost, solvent consumption and reaction time, etc., it is not suitable for the requirements of industrialized large-scale production

Method used

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  • Method for preparing dicyano-1,4phenylethenes asymmetric fluorescent whitener
  • Method for preparing dicyano-1,4phenylethenes asymmetric fluorescent whitener
  • Method for preparing dicyano-1,4phenylethenes asymmetric fluorescent whitener

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Experimental program
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Effect test

Embodiment 1

[0035] Embodiment 1: the preparation of cyanobenzyl phosphate

[0036] Under normal pressure, add 54.8g of triethyl phosphite into a 250mL four-neck bottle with a condensing device, stir mechanically, raise the temperature to about 120°C, dissolve 50g of m-cyanobenzyl chloride in 100mL of benzene and place it under constant pressure The liquid funnel was added dropwise to the reactor within 1 hour, and the benzene was continuously distilled out at the same time. After the feeding was completed, the temperature was raised to 150°C and kept for 3 hours. The reaction liquid was detected by gas chromatography, and the reaction was basically complete. The ester is 73.1g, the yield is 95.1%, and the effective content is above 98%.

[0037] When the raw material is o-cyanobenzyl chloride, the above method is used to prepare o-cyanobenzyl phosphate; when the raw material is p-cyanobenzyl chloride, the above method is used to obtain p-cyanobenzyl phosphate.

Embodiment 2

[0038] Embodiment 2: the preparation of fluorescent whitening agent ER (m / p)

[0039] Add 13.4g of terephthalaldehyde and 80mL of DMF into a 250mL three-neck flask, and add dropwise the methanol solution of 25.3g of p-cyanobenzyl phosphate and 19.3g of sodium methoxide in a constant pressure dropping funnel within 1 hour (mass percentage content 28%-30%), the temperature is controlled between 10~15 ℃, after dripping, keep warm at 20 ℃~30 ℃ for 2 hours; then add 25.3g m-cyanobenzyl phosphate and 3.3g hard Calcium fatty acid, add 19.3g of sodium methoxide solution dropwise within 1 hour (the content is the same as above), the temperature is controlled between 20°C and 30°C, and the temperature is kept at 45°C to 50°C for 2 hours after dropping. The reaction solution was beaten with 20mL of methanol, filtered under reduced pressure, washed with 20mL of methanol and 20mL of water in turn, and then dried to obtain 30.3g of yellow solid, with a yield of 91.2%, an effective content o...

Embodiment 3

[0040] Embodiment 3: the preparation of fluorescent whitening agent ER (o / p)

[0041] Add 13.4g of terephthalaldehyde and 80mL of DMF into a 250mL three-neck flask, add dropwise the methanol solution of 25.3g of o-cyanobenzyl phosphate and 19.3g of sodium methoxide in a constant pressure dropping funnel within 1 hour (content 28%-30%), the temperature is controlled between 10-15°C, and after the dripping is completed, it is kept at 20°C-30°C for 2 hours; then add 25.3g of p-cyanobenzyl phosphate and 3.3g of calcium stearate 19.3g of sodium methoxide solution (content, the same as above) was added dropwise within 1 hour, the temperature was controlled between 20°C and 30°C, and the temperature was kept at 45°C to 50°C for 2 hours after dropping. The reaction solution was beaten with 20mL of methanol, filtered under reduced pressure, washed with 20mL of methanol and 20mL of water in turn, and then dried to obtain 29.7g of a light yellow solid with a melting point of 182-184°C, a...

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Abstract

The invention provides a preparation method for a cyanogen-1, 4-styrenes asymmetric optical bleaching agent. The present method is characterized by a plurality of by products and lower yield ratio and is not suitable for large industrialization production. The method includes the following steps: cyanogen benzyl chloride is instilled into triethyl phosphite after being dissolved by a solvent for esterifying reaction, thus obtaining a product cyanobenzyl phosphate; aromatic dialdehyde and the solvent are mixed in a reactor and then the methanol solution of both p-cyanobenzyl phosphate and sodium methoxide are instilled simultaneously into the reactor with a double-instillation method for the first condensation reaction; m-cyanobenzyl phosphate and an organic dispersing agent are added intoa reaction system and the methanol solution of the sodium methoxide is instilled for the second reaction; the reaction solution is post treated, thus obtaining a yellow solid product which is a target product. The method improves the reaction security, reduces the side reaction and increases the reaction yield ratio and the content of asymmetric products.

Description

technical field [0001] The invention relates to an auxiliary agent used in plastics and fiber industries, in particular to a preparation method of a dicyano-1,4-styrene asymmetric fluorescent whitening agent. Background technique [0002] Dicyano-1,4-styrene asymmetric fluorescent whitening agent (referred to as fluorescent whitening agent ER) is one of the important fluorescent whitening agents in the structure of distyryl derivatives. It has a good whitening effect, and the whitened products can be kept for a long time without yellowing, and it has the advantages of high temperature resistance, alkali resistance, chlorine bleaching resistance, and light resistance. Fluorescent whitening agent ER (m / p), (o / p), (o / m) is the homologous compound of fluorescent whitening agent ER, which can be used for whitening polyester, acetate fiber, nylon and other fabrics; it can also be used for paint , ink, plastic, anti-counterfeiting, electrophotography and other fields. Due to the ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C255/51C07C253/30C08K5/315D06L3/12D06L4/60D06L4/664
Inventor 徐会志金可刚竹百均吴美华单雅丽吴海峰来雷
Owner ZHEJIANG TRANSFAR WHYYON CHEM
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