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Thioxanthone visible light initiator, and preparation method and application thereof

A technology of thioxanthone and visible light, applied in organic chemistry and other fields

Active Publication Date: 2021-08-13
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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  • Thioxanthone visible light initiator, and preparation method and application thereof
  • Thioxanthone visible light initiator, and preparation method and application thereof
  • Thioxanthone visible light initiator, and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0027] Preparation N, N-two (benzyl) thioxanthone photoinitiator (abbreviation TXNB 2 )

[0028] 2-aminothioxanthone (3.41g, 15.0mmol), benzyl chloride (3.89g, 30.75mmol), anhydrous potassium carbonate ( 4.67g, 33.825mmol), N,N-dimethylformamide 35mL, heated to 145°C under stirring, after 0.5h, TLC detected that the reaction was complete. Filter, concentrate, wash with water, dry, dissolve in dichloromethane, and reprecipitate 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-di(benzyl)thioxanthone photoinitiator

[0032] 2-aminothioxanthone (3.41g, 15.0mmol), benzyl chloride (4.08g, 32.25mmol), pyridine (3.19g, 40.31mmol), toluene 68mL, heated to 100°C under stirring, after 12h, TLC detected that the reaction was complete. Filter, concentrate, wash with water, dry, dissolve in dichloromethane, and reprecipitate 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-di(benzyl)thioxanthone by proton nuclear magnetic resonance spectrum data.

Embodiment 3

[0034] Preparation of N,N-di(benzyl)thioxanthone photoinitiator

[0035] 2-Aminothioxanthone (3.41g, 15.0mmol), benzyl chloride (4.18g, 33.0mmol), sodium carbonate (4.37g , 41.25mmol), xylene 40mL, heated to 120°C under stirring, after 10h, TLC detected that the reaction was complete. Filter, concentrate, wash with water, dry, dissolve in dichloromethane, and reprecipitate 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-di(benzyl)thioxanthone by proton nuclear magnetic resonance spectrum data.

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Abstract

The invention provides a thioxanthone visible light initiator, and a preparation method and application thereof. The structure of the thioxanthone visible light initiator is shown as a formula (I), and R in the formula (I) is benzyl, 4-dimethylamino benzyl, 4-methyl benzyl, 3-methyl benzyl, 2-methylbenzyl, 4-benzyloxybenzyl, 4-methoxybenzyl, 3-(trifluoromethyl)benzyl, 4-bromobenzyl, 3-cyanobenzyl, 3-nitrobenzyl, 2-(trifluoromethyl)benzyl, 3, 5-di(trifluoromethyl)benzyl or 4-cyanobenzyl. The thioxanthone visible light initiator provided by the invention has good compatibility with acrylate, can effectively initiate monomer polymerization without an auxiliary agent, can initiate cationic polymerization or free radical-cationic polymerization of epoxy and vinyl ether monomers when being compounded with iodonium salt, has high initiation activity, is simple in structure, and facilitates industrial production.

Description

technical field [0001] The invention relates to the field of photoinitiators, more specifically, to a visible photoinitiator of thioxanthone, its preparation method and application. Background technique [0002] Photopolymerization technology is a technology that uses ultraviolet light or visible light to trigger the conversion 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-absorbing photoinitiator, which is often used to initiate free radical polymerization by acting with hydrogen donor amines, etc., and can be widely used in ph...

Claims

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Application Information

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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
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