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A kind of thioxanthone visible light initiator and its preparation method and application

A thioxanthone, visible light technology, used in organic chemistry and other directions

Active Publication Date: 2022-06-28
GUIZHOU EDUCATION UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The existing thioxanthone initiators that can be used in free radical-cationic curing systems cannot take into account the characteristics of visible light initiation, high initiation activity and simple synthesis method (suitable for industrial production) at the same time.

Method used

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  • A kind of thioxanthone visible light initiator and its preparation method and application
  • A kind of thioxanthone visible light initiator and its preparation method and application
  • A kind of thioxanthone visible light initiator and its preparation method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0027] Preparation of N,N-bis(benzyl)thioxanthone photoinitiator (TXNB for short) 2 )

[0028] 2-Aminothioxanthone (3.41g, 15.0mmol), benzyl chloride (3.89g, 30.75mmol), anhydrous potassium carbonate ( 4.67 g, 33.825 mmol), 35 mL of N,N-dimethylformamide, heated to 145° C. with stirring, and TLC detected the reaction completion after 0.5 h. Filtration, concentration, washing with water, drying, dissolving in dichloromethane, and reprecipitation in petroleum ether to obtain 5.07 g of pure product with a yield of 83%.

[0029] 1 H NMR (CDCl 3 , 400MHz) δppm (such as figure 1shown): 4.76(s, 4H), 6.75-6.80(d, J=8.80Hz, 2H), 7.22-7.27(m, 4H), 7.30-7.34(m, 2H), 7.34-7.40(m, 4H) ), 7.42-7.48(m, 2H), 7.50-7.56(t, J=7.2Hz, 1H), 7.71-7.79(m, 4H).

Embodiment 2

[0031] Preparation of N,N-bis(benzyl)thioxanthone photoinitiators

[0032] 2-Aminothioxanthone (3.41g, 15.0mmol), benzyl chloride (4.08g, 32.25mmol), pyridine (3.19g, 40.31 mmol), 68 mL of toluene, heated to 100° C. with stirring, and the completion of the reaction was detected by TLC after 12 h. Filtration, concentration, washing with water, drying, dissolving in dichloromethane, and reprecipitation in petroleum ether to obtain 5.61 g of pure product with a yield of 92%. The obtained pure product was confirmed to be N,N-bis(benzyl)thioxanthone from the data of H NMR spectrum.

Embodiment 3

[0034] Preparation of N,N-bis(benzyl)thioxanthone photoinitiators

[0035] 2-Aminothioxanthone (3.41g, 15.0mmol), benzyl chloride (4.18g, 33.0mmol), sodium carbonate (4.37g) were added to a 250ml three-necked flask equipped with a reflux condenser, a thermometer and a stirring bar. , 41.25 mmol), 40 mL of xylene, heated to 120° C. with stirring, and TLC detected the completion of the reaction after 10 h. Filtration, concentration, washing with water, drying, dissolving in dichloromethane, and reprecipitation in petroleum ether to obtain 5.68 g of pure product with a yield of 93%. The obtained pure product was confirmed to be N,N-bis(benzyl)thioxanthone from the data of H NMR spectrum.

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Abstract

The invention provides a thioxanthone visible light initiator, a preparation method and an application. The structure of this thioxanthone visible photoinitiator is shown in formula (I), wherein R is benzyl, 4-dimethylaminobenzyl, 4-methylbenzyl, 3-methylbenzyl, 2-methyl Benzyl, 4-benzyloxybenzyl, 4-methoxybenzyl, 3-(trifluoromethyl)benzyl, 4-bromobenzyl, 3-cyanobenzyl, 3-nitrobenzyl, 2-(trifluoromethyl)benzyl, 3,5-bis(trifluoromethyl)benzyl or 4-cyanobenzyl. The thioxanthone visible light initiator provided by the present invention has good compatibility with acrylates, can effectively initiate monomer polymerization without additives, and can initiate epoxy and ethylene polymerization when used in combination with iodonium salts. Cationic polymerization or radical-cationic polymerization of base ether monomers has high initiating activity and simple structure, which is beneficial to industrial production.

Description

technical field [0001] The invention relates to the field of photoinitiators, and more particularly, to a visible light initiator of thioxanthone, and a preparation method and application thereof. Background technique [0002] Photopolymerization technology is a technology that uses ultraviolet light or visible light to initiate the transformation of reactive liquid substances into solid substances. At present, there are many kinds of photoinitiators, and the initiation mechanism can be roughly divided into four types: decomposition reaction mechanism, hydrogen extraction reaction mechanism, energy transfer mechanism and ion reaction mechanism. According to the reaction mechanism, photoinitiators are mainly divided into free radical photoinitiators and cationic photoinitiators. Among them, thioxanthone photoinitiator is a common hydrogen-pumping photoinitiator, which is often used with hydrogen-donating amines to initiate free radical polymerization, and can be widely used ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C08F2/48C07D335/16C08G59/02
CPCC08F2/48C07D335/16C08G59/022
Inventor 武青青邓明森沈虎峻
Owner GUIZHOU EDUCATION UNIV