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Thioxanthone photoinitiator with high migration stability as well as preparation method and application of thioxanthone photoinitiator

A technology of thioxanthone light and xanthone light, which is applied in the field of thioxanthone photoinitiator and preparation with high migration stability, can solve the problems of complex synthesis methods, poor compatibility, and photoactive group hindrance , to achieve the effect of high migration stability, good compatibility and simple synthesis

Active Publication Date: 2021-08-24
GUIZHOU EDUCATION UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Thioxanthone photoinitiator is a kind of extensive photoinitiator of research, and the ultraviolet light photoinitiator thioxanthone (isopropylthioxanthone, US6025408) that commercially uses in large quantities is compatible with photocuring system Poor sex
Chinese patent CN 1546488A discloses a preparation method containing bicycloalkyl thioxanthone, which can be used as a monomer or as an ultraviolet photoinitiator; Chinese patent CN 1594399A discloses a thioxanthone containing a co-initiator amino group preparation method, but the photoactive group on the main chain is easily hindered by the macromolecular segment, which is not conducive to exerting the advantages of macromolecular photoinitiators
Our research team has previously developed a visible light initiator containing thioxanthone containing acrylate or methacrylate. Although it also has high migration stability, the synthesis method is relatively complicated, which is not conducive to industrial production.

Method used

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  • Thioxanthone photoinitiator with high migration stability as well as preparation method and application of thioxanthone photoinitiator
  • Thioxanthone photoinitiator with high migration stability as well as preparation method and application of thioxanthone photoinitiator
  • Thioxanthone photoinitiator with high migration stability as well as preparation method and application of thioxanthone photoinitiator

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Experimental program
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Effect test

Embodiment 1

[0027] This embodiment provides a thioxanthone photoinitiator, the preparation method is as follows:

[0028] a, preparation of 2-(N-benzyl)aminothioxanthone

[0029] 2-Aminothioxanthone (3.41g, 15.0mmol), benzyl chloride (1.99g, 15.75mmol), anhydrous potassium carbonate ( 2.39g, 17.325mmol), N,N-dimethylformamide 35mL, heated to 145°C under stirring, after 0.5h, TLC detected that the reaction was complete, and 2-(N-benzyl)aminothioxanthone was obtained. Filter, concentrate, wash with water, dry, dissolve in dichloromethane, and reprecipitate in petroleum ether to obtain 4.38 g of pure product with a yield of 92%.

[0030] 1 H NMR (CDCl 3 ,400MHz) δppm: 4.32(s,1H,-NH),4.47(s,2H,-CH 2 ),6.98-7.06(dd,J 1 =2.4Hz,J 2 =8.8Hz,1H,Ar-H),7.30-7.51(m,7H,Ar-H),7.55-7.64(m,2H,Ar-H),7.85-7.91(d,J=2.4Hz,1H, Ar-H), 8.59-8.65 (d, J=7.6Hz, 1H, Ar-H).

[0031]b, preparation of 2-(N-benzyl) acrylamidothioxanthone

[0032] Add 3.17g (10mmol) of 2-(N-benzyl)aminothioxanthone to a 250ml th...

Embodiment 2

[0035] This embodiment provides a thioxanthone photoinitiator, the preparation method is as follows:

[0036] a, preparation of 2-(N-allyl) aminothioxanthone

[0037] 2-aminothioxanthone (3.41g, 15.0mmol), allyl chloride (1.49g, 19.5mmol), pyridine (1.85g , 23.4mmol), 65mL of toluene, heated to 100°C under stirring, after 12h, TLC detected that the reaction was complete. Wash with water, dry the organic layer, dissolve in dichloromethane, and reprecipitate in petroleum ether to obtain 3.51 g of pure 2-(N-allyl)aminothioxanthone with a yield of 88%.

[0038] 1 H NMR (CDCl 3 ,400MHz)δppm:3.88-3.94(d,2H,NCH 2 ,d=4.8Hz), 4.34(s,1H,-NH),5.16-5.36(m,2H,-CH=CH 2 ),5.94-6.20(m,1H,-CH=CH 2 ),6.98-7.04(dd,1H,Ar-H,J 1 =3.0Hz,J 2 =8.4Hz),7.41-7.46(m,2H,Ar-H),7.54-7.60(m,1H,Ar-H)7.76-7.79(m,1H,Ar-H),7.84(d,1H,Ar -H,J=3.0Hz),8.61(d,1H,Ar-H,J=8.4Hz)

[0039] b, preparation of 2-(N-allyl) acrylamidothioxanthone

[0040] Add 2.67g (10mmol) of 2-(N-allyl)aminothioxanthone to a 250ml ...

Embodiment 3

[0043] This embodiment provides a thioxanthone photoinitiator, the preparation method is as follows:

[0044] a, preparation of 2-(N-benzyl)aminothioxanthone

[0045] 2-aminothioxanthone (3.41g, 15.0mmol), benzyl chloride (2.47g, 19.5mmol), pyridine (1.85g, 23.4mmol), toluene 68mL, and heated to 100°C under stirring. After 12h, TLC detected that the reaction was complete, and 2-(N-benzyl)aminothioxanthone was obtained. Filter, concentrate, wash with water, dry, dissolve in dichloromethane, and reprecipitate in petroleum ether to obtain 3.13 g of pure product with a yield of 65.8%. The obtained pure product was confirmed to be 2-(N-benzyl)aminothioxanthone by proton nuclear magnetic resonance spectrum data.

[0046] b, preparation of 2-(N-benzyl) acrylamidothioxanthone

[0047] Add 3.17g (10mmol) of 2-(N-benzyl)aminothioxanthone into a 250ml three-necked flask equipped with a stirring bar, add 35ml of dry toluene, and 1.11g (11mmol) of triethylamine, stir well, and use Slow...

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Abstract

The invention provides a thioxanthone photoinitiator with high migration stability as well as a preparation method and application of the thioxanthone photoinitiator. The structure of the thioxanthone photoinitiator with high migration stability is shown as a formula (I), and R is allyl, benzyl, 4-dimethylaminobenzyl, 4-methylbenzyl, 3-methylbenzyl, 2-methylbenzyl, 4-benzyloxybenzyl, 4-tert-butylbenzyl, 4-methoxybenzyl, 3-(trifluoromethyl)benzyl, 4-bromobenzyl, 3-cyanobenzyl, 3-nitrobenzyl, 2-(trifluoromethyl) benzyl, 3,5-bis(trifluoromethyl)benzyl, 4-iodobenzyl, 4-bromobenzyl or 4-cyanobenzyl. The thioxanthone photoinitiator provided by the invention has good compatibility with acrylate and high migration stability, a solvent does not need to be added to dissolve the photoinitiator, and monomer polymerization can be effectively initiated without an auxiliary agent. The thioxanthone photoinitiator provided by the invention is simple in structure, simple and convenient to synthesize and suitable for large-scale production.

Description

technical field [0001] The invention relates to the field of photoinitiators, more specifically, to a thioxanthone photoinitiator with high migration stability, its preparation method and application. Background technique [0002] Photopolymerization is a very important technology that is widely used in many fields, such as photocurable coatings, inks, microelectronics, adhesives, photoresists, dental curing, 3D printing and other fields. In these applications, the process of controlling photopolymerization lies in the photoinitiator, which accounts for a small proportion in the photocuring system, but plays a decisive role in the speed of photocuring. At present, the research on UV curing technology is relatively mature, and there are many commercial UV photoinitiators. Thioxanthone photoinitiator is a kind of extensive photoinitiator of research, and the ultraviolet light photoinitiator thioxanthone (isopropylthioxanthone, US6025408) that commercially uses in large quanti...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D311/86C08F2/48
CPCC07D311/86C08F2/48
Inventor 武青青邓明森李付绍
Owner GUIZHOU EDUCATION UNIV