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Method for preparing polymeric benzophenone derivative photoinitiator

A technology of benzophenone and photoinitiator is applied in the field of preparation of polymerizable benzophenone derivative photoinitiator, which can solve the problems of easy volatility, small molecular weight, toxicity and the like, and achieves improved compatibility and reduced volatility. and migratory effects

Inactive Publication Date: 2013-01-09
HANGZHOU INST OF ADVANCED MATERIAL BEIJING UNIV OF CHEM TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In free radical polymerization, benzophenone is a common hydrogen abstraction photoinitiator. It has a simple structure, is easy to synthesize, and has high initiating activity. However, it has a low melting point, small molecular weight, and is volatile, and it is easy to migrate and precipitate on the surface in the cured film. , resulting in toxicity, which restricts its application in food and drug packaging

Method used

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  • Method for preparing polymeric benzophenone derivative photoinitiator
  • Method for preparing polymeric benzophenone derivative photoinitiator
  • Method for preparing polymeric benzophenone derivative photoinitiator

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0023] Dissolve 0.05g of p-hydroxyanisole and 0.05g of tetrabutylammonium bromide in 3.3g of acrylic acid, slowly add dropwise to 10.5g of 4-(2,3-epoxypropoxy)diphenyl In ketone (EBP), heat and stir, the temperature is controlled at 85°С, the dropwise addition is completed in 2 hours, the temperature rises to 100°С, the reaction is completed in 2 hours, cooled to room temperature, dissolved in dichloromethane, and mixed with 10mL 2% NaOH solution, deionized water were washed 2 times, anhydrous sodium sulfate dried overnight, filtered, rotary evaporation to remove dichloromethane, vacuum-dried to obtain a polymerizable benzophenone derivative photoinitiator 4—(acrylic acid-2- hydroxypropyl-3-oxy)benzophenone. The structure is shown in structural formula 1: 1 H NMR (250MHz) in CDCl 3 : δ2ppm (1H, OH), 3.95ppm (1H, CH), 3.09, 4.09ppm (4H, CH 2 ), 6.12-6.37ppm (3H, CH=CH 2 ), 6.87-7.70ppm (9H, benzene ring)

[0024]

Embodiment 2

[0026] Dissolve 0.04g of p-hydroxyanisole and 0.05g of tetrabutylammonium bromide in 3.3g of methacrylic acid, slowly add dropwise to 10.5g of 4-(2,3-epoxypropoxy) In benzophenone (EBP), heat and stir, the temperature is controlled at 85 ° С, 2h dropwise is completed, the temperature rises to 100 ° С, 2h reaction is completed, cooled to room temperature, it is dissolved in dichloromethane, with 10mL2 % NaOH solution and deionized water were washed 2 times respectively, dried over night with anhydrous sodium sulfate, filtered, rotary evaporated to remove dichloromethane, and dried in vacuum to obtain a polymerizable benzophenone derivative photoinitiator 4—(methacrylic acid -2-hydroxypropyl-3-oxy)benzophenone. The structure is shown in structural formula 2: 1 H NMR (250MHz) in CDCl 3 : δ1.93ppm (3H, CH 3 ), 2ppm (1H, OH), 3.95ppm (1H, CH), 3.09, 4.09ppm (4H, CH 2 ), 5.90, 6.09ppm (2H, C=CH 2 ), 6.87-7.70ppm (9H, benzene ring)

[0027]

Embodiment 3

[0029] Dissolve 0.04g of p-hydroxyanisole and 0.06g of tetrabutylammonium bromide in 3.3g of hydroxyethyl acrylate, and slowly add it dropwise to 11.5g of 4-(2,3-epoxypropoxy ) in benzophenone (EBP), heated and stirred, the temperature was controlled at 90 ° С, the dropwise addition was completed in 2 hours, the temperature rose to 100 ° С, the reaction was completed in 2 hours, cooled to room temperature, dissolved in dichloromethane, and used 10mL of 2% NaOH solution and deionized water were washed twice respectively, dried overnight over anhydrous sodium sulfate, filtered, rotary evaporated to remove methylene chloride, and dried in vacuo to obtain a polymerizable benzophenone derivative photoinitiator 4—(propylene Acyloxy-4-hydroxy-3,5-dioxy)benzophenone. The structure is shown in structural formula 3: 1 H NMR (250MHz) in CDCl 3 : δ2ppm (1H, OH), 3.65, 4.26, 4.32ppm (6H, CH 2 ), 5.08ppm (1H, CH), 5.80, 6.05, 6.43ppm (3H, CH=CH 2 ), 6.87-7.70ppm (9H, benzene ring)

[0...

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Abstract

The invention discloses a method for preparing a polymeric benzophenone derivative photoinitiator of which a formula is shown in the specification. According to the preparation method, epoxy group-contained benzophenone serving as a raw material and unsaturated carboxylic acid or unsaturated carboxylic ester are subjected to ring opening reaction in the presence of a polymerization inhibitor and tetrabutylammonium bromide to form the polymeric photoinitiator. Due to the existence of polymeric groups, the compatibility of the photoinitiator and a light polymerization system is improved, the surface mobility of the normal small molecular photoinitiator is greatly lowered in the photo-curing process, and the polymeric group can also be used as a monomer for synthesizing the macromolecular photoinitiator. Therefore, the preparation method has a wide application prospect.

Description

technical field [0001] The invention relates to a preparation method of a polymerizable benzophenone derivative photoinitiator Background technique [0002] Photocuring technology is a new type of environmentally friendly green technology that came out in the 1960s. It has the characteristics of fast curing speed, less pollution, energy saving, and excellent performance of cured products. Therefore, it is used in photoresists, photocurable coatings, and electronic packaging materials. , light-curing inks, adhesives, printing materials, etc. have a wide range of applications. Generally, the photocuring system includes three main components, namely oligomer, monomer, and photoinitiator, wherein the photoinitiator is the key component of the photocuring system. According to the mechanism of action, photoinitiators can be divided into free radical initiators and cationic initiators, and free radical initiators can be divided into two types: cleavage type and hydrogen abstractio...

Claims

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Application Information

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IPC IPC(8): C07C49/84C07C45/45C08F2/48
Inventor 聂俊朱晓丹马贵平包容
Owner HANGZHOU INST OF ADVANCED MATERIAL BEIJING UNIV OF CHEM TECH
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