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Triaryl sulfonium salt containing benzoxazole skeleton and preparation method thereof

A technology of benzoxazolylsulfenyl and benzoxazole, which is applied in the field of triarylsulfonium salts, can solve the problems of low solubility, achieve high conjugation degree, high conjugation degree, and reduce the release amount

Inactive Publication Date: 2015-10-28
SHANXI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

As a common cationic initiator, calcite salts have the disadvantages of low solubility and the formation of small odorous molecules (such as benzene and diphenyl sulfide) when the C-S bond is broken during curing radiation.

Method used

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  • Triaryl sulfonium salt containing benzoxazole skeleton and preparation method thereof
  • Triaryl sulfonium salt containing benzoxazole skeleton and preparation method thereof
  • Triaryl sulfonium salt containing benzoxazole skeleton and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0025] In a 100mL long-necked round bottom flask, add 2-mercaptobenzoxazole (2mmol), 1,4-diiodobenzene (1mmol) successively, dissolve with DMF (4mL), and then add cuprous iodide (0.1mmol) , and finally potassium hydroxide (4 mmol) was added. Put the flask into a microwave reactor, set the power to 30W, and react for 20min. The reaction solution was transferred to a separatory funnel, extracted with ethyl acetate and washed with brine, then the organic phase was dried over anhydrous sodium sulfate, filtered, and the solvent was removed by rotary evaporation, followed by column chromatography to obtain the product 1,4-bis(benzene and oxazol-2-thio)benzene, compound (I).

[0026] Compound (I): white crystals, m.p.125-128°C, yield 75.8%. 1 H NMR (CDCl 3 , 300MHz) δ:7.25-7.46(m,ArH,9H),7.72-7.84(m,ArH,3H).

Embodiment 2

[0028] In a 50mL single-neck round bottom flask equipped with a stirring bar, the compound 1,4-bis(benzoxazol-2-thio)benzene (1mmol), diphenyliodotrifluoromethanesulfonate (2.4 mmol), dissolved in 1,1,2,2-tetrachloroethane (2 mL), and finally added cuprous iodide (0.1 mmol), stirred evenly, and reacted in an oil bath at 110° C. for 2 h. The reaction solution was transferred to a separatory funnel, extracted with ethyl acetate and washed with brine, then the organic phase was dried over anhydrous sodium sulfate, filtered, and the solvent was removed by rotary evaporation, followed by column chromatography, and the mixture was sequentially washed with dichloromethane, ethyl acetate The ester was used as the eluent for column chromatography to obtain compound (II-a) as white crystals.

[0029]

[0030] Compound (II-a): white crystals, m.p 202-205°C, yield 66.7%. 1 HNMR (CDCl 3 , 300MHz) δ:7.28-7.30(m,ArH,3H),7.44-7.46(m,ArH,2H),7.63-7.64(m,ArH,2H),7.77(m,ArH,4H).

Embodiment 3

[0032] In a 50mL single-necked round bottom flask equipped with a stirring bar, the compound 1,4-bis(benzoxazol-2-thio)benzene (1mmol), bis-(4-methylphenyl)iodotrifluoromethane were sequentially added The sulfonate (2.4 mmol) was dissolved in 1,1,2,2-tetrachloroethane (2 mL) and finally copper iodide (0.1 mmol) was added. After stirring evenly, react in an oil bath at 110°C for 2h. The reaction solution was transferred to a separatory funnel, extracted with ethyl acetate and washed with brine, then the organic phase was dried over anhydrous sodium sulfate, filtered, and the solvent was removed by rotary evaporation, followed by column chromatography, and the mixture was sequentially washed with dichloromethane, ethyl acetate The ester was used as the eluent for column chromatography to obtain compound (II-b) as white crystals.

[0033]

[0034] Compound (II-b): white crystals, m.p 167-169°C, yield 76.1%. 1 H NMR (CDCl 3 ,300MHz)δ:2.43(s,CH 3 ,3H),7.04-7.05(m,ArH,2H),7.1...

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Abstract

The invention relates to an aromatic sulfonium salt compound, in particular to triaryl sulfonium salt containing a benzoxazole skeleton and a preparation method and application thereof. The method includes the steps that 2-sulfydryl benzoxazole and 1,4-diiodobenzene are used for conducting a C-S key coupling reaction under microwave radiation to synthesize a phenyl disulfide compound, and then the 2-sulfydryl benzoxazole and the 1,4-diiodobenzene are reacted with high iodised salt, so that the triaryl sulfonium salt containing the benzoxazole skeleton is obtained. The ultraviolet absorption wavelength range of the compound can be widened by more than 290 nm in a red shift mode, the triaryl sulfonium salt containing the benzoxazole skeleton can be used as a kation photoinitiator for an ultraviolet light polymerization composition in an ultraviolet curing coating, and the surface curing ability and the solubility are good.

Description

technical field [0001] The present invention relates to a triaryl sulfonium salt, specifically a triaryl sulfonium salt containing a benzoxazole skeleton and a disulfide atom and a preparation method thereof, and the salt is used as a photoinitiator in an ultraviolet light curing composition, especially an ultraviolet light curing composition. application in cured coatings. Background technique [0002] As a green technology, UV curing technology is widely used in coatings, inks, electronics, biology and other fields. The UV curing system is mainly composed of resin, monomer, photoinitiator and auxiliary agent. Among them, the photoinitiator is the key component, which generates active free radicals or cations after absorbing ultraviolet light, and initiates rapid polymerization and curing of the resin to form a film. Compared with the free radical type, the cationic photoinitiator has a smaller shrinkage rate of the coating after curing, and better adhesion and other prop...

Claims

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Application Information

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IPC IPC(8): C07D263/58C08F2/48C09D163/10C09D7/12
CPCC07D263/58C08F2/48C08K5/103C08K5/17C09D7/63C09D163/10
Inventor 张变香史瑞雪
Owner SHANXI UNIV
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