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Thioxanthone-chalcone photoinitiator as well as preparation method and application thereof

A technology of photoinitiator and thioxanthone, applied in the direction of organic chemistry, can solve the problems of small volume shrinkage, cationic polymerization inhibition, long dark reaction, etc., and achieve the effect of simple synthesis method, high initiation activity and simple structure

Active Publication Date: 2021-12-24
GUIZHOU EDUCATION UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Cationic curing is not sensitive to oxygen, and the volume shrinkage rate is small during curing, which is easy to adhere to the substrate, but the dark reaction is long, and water and alkaline substances can easily cause cationic polymerization inhibition

Method used

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  • Thioxanthone-chalcone photoinitiator as well as preparation method and application thereof
  • Thioxanthone-chalcone photoinitiator as well as preparation method and application thereof
  • Thioxanthone-chalcone photoinitiator as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0026] Preparation of 2-(3-(4-(dimethylamino)phenyl)-3-carbonyl-1-en-1-yl)-thioxanthone (TX-DMAP)

[0027] 2-formyl thioxanthone (2.40g, 10.0mmol), 4-dimethylaminoacetophenone (1.79g, 11mmol) were charged in a 250ml three-necked flask equipped with a reflux condenser, a thermometer, and a stirring bar, Sodium hydroxide (the amount of sodium hydroxide used is such that the concentration of alkali in the reaction system is 16% (m / m)), 50% v / v ethanol 36mL, stirred at room temperature, and TLC detected that the reaction was complete after 3.0h. Filter, wash the filter cake with water and ethanol, and dry to obtain 3.35 g of pure product with a yield of 87%.

[0028] The pure product verified by infrared data and proton nuclear magnetic resonance spectrum data is 2-(3-(4-(dimethylamino)phenyl)-3-carbonyl-1-en-1-yl)-thioxanthone. Among them, the proton nuclear magnetic resonance spectrum data is HNMR (CDCl 3 ,400MHz): 3.13(s,6H,NCH 3 ), 6.72-6.78(d, 2H, J=9.2Hz), 7.52-7.58(t, 1H...

Embodiment 2

[0030] Preparation of 2-(3-(4-(dimethylamino)phenyl)-3-carbonyl-1-en-1-yl)-thioxanthone (TX-DMAP)

[0031]2-formyl thioxanthone (2.40g, 10.0mmol), 4-dimethylaminoacetophenone (1.96g, 12mmol) were charged in a 250ml three-necked flask equipped with a reflux condenser, a thermometer, and a stirring bar, Potassium carbonate (the amount of potassium carbonate used is such that the concentration of alkali in the reaction system is 16% (m / m)), 30 mL of ethanol, stirred at room temperature, and the reaction was detected by TLC after 12 hours. Filter, wash the filter cake with water, wash with ethanol, and dry to obtain 3.27 g of pure product with a yield of 85%. The obtained pure product was confirmed to be TX-DMAP by IR and H-NMR data.

Embodiment 3

[0033] Preparation of 2-(3-(4-(dimethylamino)phenyl)-3-carbonyl-1-en-1-yl)-thioxanthone (TX-DMAP)

[0034] 2-formyl thioxanthone (2.40g, 10.0mmol), 4-dimethylaminoacetophenone (2.12g, 10.5mmol) were charged into a 250ml three-necked flask equipped with a reflux condenser, a thermometer, and a stirring bar. , potassium bicarbonate (the amount of potassium bicarbonate used is such that the concentration of alkali in the reaction system is 16% (m / m)), 45 mL of N,N-dimethylformamide, stirred at room temperature, and TLC detected that the reaction was complete after 10 h. Filter, wash the filter cake with water, wash with ethanol, and dry to obtain 3.0 g of pure product with a yield of 78%. The obtained pure product was confirmed to be TX-DMAP by IR and H-NMR data.

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Abstract

The invention provides a thioxanthone-chalcone photoinitiator as well as a preparation method and application thereof. The structure of the thioxanthone-chalcone photoinitiator is shown as a formula (I), and in the formula (I), R is NR1, wherein R1 is selected from hydrogen and alkyl. The thioxanthone-chalcone photoinitiator provided by the invention is suitable for initiating free radical polymerization of acrylate monomers and methacrylate monomers, a solvent does not need to be added to dissolve the photoinitiator, monomer polymerization can be effectively initiated without other auxiliaries, and the initiation activity is relatively high. The thioxanthone-chalcone photoinitiator disclosed by the invention is compounded with iodonium salt for use, and only a very small amount of photoinitiator is needed, so that cationic polymerization of epoxy monomers can be effectively initiated, and free radical-cationic polymerization of a mixture of acrylate monomers / epoxy monomers can also be initiated to form an interpenetrating polymer network structure.

Description

technical field [0001] The invention relates to the field of photoinitiators, more specifically, to a thioxanthone-chalcone photoinitiator and its preparation method and application. Background technique [0002] Photocuring technology refers to the technology that under the light, the photoinitiator absorbs light energy and generates active groups such as free radicals, cations, anions, etc., thereby triggering the cross-linking and polymerization of monomers or oligomers. This technology can be widely used in light curing. Curing coatings, inks, metal coatings, photoresists, 3D printing and other fields. At present, there are many kinds of photoinitiators. According to the action mechanism of photoinitiators, photoinitiators can be divided into free radical photoinitiators and cationic photoinitiators. [0003] Thioxanthone initiator is a widely studied photoinitiator, which can be used as a free radical photoinitiator or a cationic photoinitiator. Existing thioxanthone ...

Claims

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Application Information

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IPC IPC(8): C08F2/48C08G59/68C07D335/16
CPCC08F2/48C08G59/687C07D335/16
Inventor 武青青邓明森杨贵琴许善胜
Owner GUIZHOU EDUCATION UNIV
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