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Triarylsulfonium salt as well as preparation method and application thereof

A technology of triaryl and sulfonium salts, applied in the application field of triaryl sulfonium salts and their preparation, and UV-curable coatings, can solve the problems of small molecular weight, migration, and volatilization of benzophenone, and achieve good Reactivity, improvement of curing efficiency, high reactivity effect

Inactive Publication Date: 2013-09-04
山西亮龙涂料有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, due to the small molecular weight of benzophenone itself, it is easy to volatilize and migrate, resulting in odor and poisonous gas in the product, and benzene will be released during the use of benzophenone, which limits its use.

Method used

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  • Triarylsulfonium salt as well as preparation method and application thereof
  • Triarylsulfonium salt as well as preparation method and application thereof
  • Triarylsulfonium salt as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0021] Put a magnetic stirring bar, 4-benzoyl-4'-methyl-diphenyl sulfide (BMS) (1.0 mmol), and diphenyl iodine trifluoromethanesulfonate in a two-necked flask equipped with a condenser (1.2mmol) and copper acetate (0.1mmol) were added into the reactor, mixed evenly, and reacted for 30min in an oil bath at 130°C under solvent-free conditions. After cooling to room temperature, the mixture was sequentially separated by column chromatography using dichloromethane, ethyl acetate and ethanol as eluents to obtain a light yellow viscous product (I).

[0022]

[0023] Product (I): light yellow viscous substance, yield 83.9%. UV spectrum see figure 1 ; H NMR spectrum ( figure 2 ): 1 HNMR (CDCl 3 , 300MHz) δ: 2.53-2.58 (d, CH 3 NMR carbon Spectrum ( image 3 ): 13 C NMR (CDCl 3 , 75MHz) δ: 20.92, 119.98, 124.17, 128.21, 128.46, 129.44, 130.53, 130.72, 131.04, 131.27, 131.76, 133.05, 134.18, 135.28, 141.63, 145.77, 193.57.

Embodiment 2

[0025] Put a magnetic stirring bar, 4-benzoyl-4′-methyl-diphenyl sulfide (BMS) (1.0 mmol), two-(4-tolyl) iodine tri Add fluoromethanesulfonate (1.2mmol) and copper acetate (0.1mmol) into the reactor, mix well, and react in an oil bath at 130°C for 30min under solvent-free conditions. After cooling to room temperature, the mixture was sequentially separated by column chromatography using dichloromethane, ethyl acetate and ethanol as eluents to obtain the product (II) as a milky white solid.

[0026]

[0027] Product (II): milky white solid, yield 91.7%. UV spectrum see Figure 4 ; H NMR spectrum ( Figure 5 ): 1 HNMR (CDCl 3 , 300MHz) δ: 2.44-2.50(s, CH 3 ,6H),7.56-7.63(m,ArH,6H),7.70-7.72(m,ArH,1H),7.78-7.80(m,ArH,6H),7.88-7.91(m,ArH,2H),8.00- 8.03(m,ArH,2H).Carbon NMR ( Figure 6 ): 13 C NMR (CDCl 3 , 75MHz) δ: 20.05, 120.46, 127.84, 128.69, 128.95, 129.88, 130.49, 131.00, 132.68, 134.77, 140.57, 144.65, 193.51.

Embodiment 3

[0029] Put a magnetic stirring bar in a two-necked flask equipped with a condenser, 4-benzoyl-4'-methyl-diphenyl sulfide (BMS) 1.0mmol), di-(4-methylphenyl) iodine trifluoro Methanesulfonate (1.2mmol) and copper acetate (0.1mmol) were added into the reactor, mixed evenly, and reacted in an oil bath at 110°C for 30min under solvent-free conditions. After cooling to room temperature, the mixture was sequentially separated by column chromatography using dichloromethane, ethyl acetate, and ethanol as eluents to obtain the product (II) as a milky white solid with a yield of 54.3%.

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Abstract

The invention discloses a triarylsulfonium salt with a benzophenone framework as well as a preparation method and application of the triarylsulfonium salt. According to the method, 4-benzoyl-4'-methyl-diphenyl sulfide (BMS) is used as a raw material to react with a diaryliodonium salt under the copper-catalyzed condition to prepare the triarylsulfonium salt; and the maximum ultraviolet absorption wavelength range of the compound can be shifted to 250nm, and meanwhile, the ultraviolet absorption wavelength range is widened due to the existence of free radicals and cation ion initiating groups. The prepared triarylsulfonium salt can be used as a photoinitiator for an ultraviolet photo-cured compound and particularly for an ultraviolet photo-cured coating, and has favorable reaction activity, surface curing capability and solubility; and the mixed groups exist in a molecule to ensure that the molecule is relatively stable, so that the light inhibiting performance is effectively improved.

Description

technical field [0001] The invention relates to a triarylsulfonium salt, specifically a triarylsulfonium salt containing a benzophenone skeleton and a preparation method thereof, and the use of the salt as a photoinitiator in a UV-curable composition, especially a UV-curable coating application. Background technique [0002] Photocuring technology is a rapidly developing green new technology. In recent years, people have combined UV curing technology with coatings to develop UV curing coatings. This is a new type of green, environmentally friendly and energy-saving coating that can be cross-linked and cured to form a film in a short period of time under ultraviolet light irradiation. The photocuring system is generally composed of unsaturated resin, reactive diluent, photoinitiator and auxiliary agent. Photoinitiator is an important component of UV-curable coatings. It absorbs ultraviolet light and undergoes a chemical reaction to generate active free radicals and active c...

Claims

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Application Information

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IPC IPC(8): C07C381/12C09D7/12C09D163/10
Inventor 张变香常姣魏保利闫光红
Owner 山西亮龙涂料有限公司
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