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Triaryl sulfonium salt containing 1-methyl-2-phenyl indole skeleton and preparation method thereof

A phenylindole, triaryl technology, applied in triaryl sulfonium salt and its preparation, the application field of ultraviolet curing coatings, can solve the problems of cracking, low solubility, etc., to reduce the release amount and the degree of molecular conjugation The effect of high, good reactivity

Inactive Publication Date: 2014-08-13
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

It is well known that calcite salts can be used as initiators for cationic polymerization in curing systems, but in practical applications there are disadvantages of low solubility and the formation of small molecules (such as benzene and diphenyl sulfide) due to C-S bond breakage during curing radiation

Method used

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  • Triaryl sulfonium salt containing 1-methyl-2-phenyl indole skeleton and preparation method thereof
  • Triaryl sulfonium salt containing 1-methyl-2-phenyl indole skeleton and preparation method thereof
  • Triaryl sulfonium salt containing 1-methyl-2-phenyl indole skeleton and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0020] Put a magnetic stirring bar in a two-necked flask equipped with a condenser, add diphenyl disulfide (1.1mmol) and 1-methyl-2-phenylindole (2mmol) respectively, drop DMSO until just dissolved, Cuprous iodide (0.1 mmol) was added, and the temperature was raised to 110° C., followed by reaction for 6 hours. After the reaction, the solvent was removed by rotary evaporation, and column chromatography was carried out to obtain 1-methyl-2-phenyl-3-phenylindole sulfide as white crystals. The yield was 78%, and the melting point was 102- 104°C. 1H NMR (300MHz, CDCl3): 3.75(s, CH3, 3H), 7.01-7.19(m, ArH, 7H), 7.22-7.26(m, ArH, 1H), 7.32-7.37(m, ArH, 5H), 7.41 (m, ArH, 1H).

Embodiment 2

[0022] A magnetic stirring bar was placed in a two-necked flask equipped with a condenser, and diphenyl iodide trifluoromethanesulfonate (1.1 mmol) and 1-methyl-2-phenyl-3-phenylsulfide ind Indole (1mmol), add 1,1,2,2-tetrachloroethane dropwise until just dissolved, then add cuprous iodide (0.1mmol), copper powder (0.05mmol), rise to 110°C, react for 2.5 hours . After the reaction liquid was cooled to room temperature, the solvent was spun off, and the mixture was subjected to column chromatography using dichloromethane and ethyl acetate as eluents successively to obtain compound (I) as white crystals.

[0023]

[0024] Compound (I): white crystals, yield 61.3%, melting point 204-205°C. UV spectrum see figure 1 ; H NMR spectrum see figure 2 ; 1 HNMR (300MHz, CDCl 3 ):3.83(s,N-CH 3 ,3H), 7.17~7.19(m,ArH,4H), 7.22~7.44(m,ArH,5H), 7.45~7.64(m,ArH,5H), 7.67~7.73(m,ArH,5H).

Embodiment 3

[0026] A magnetic stirrer was placed in a two-necked flask equipped with a condenser, and bis-(4-methylphenyl)iodotrifluoromethanesulfonate (1.1 mmol) and 1-methyl-2-phenyl-3- Phenylsulfide indole (1mmol), add 1,1,2,2-tetrachloroethane dropwise until just dissolved, then add cuprous iodide (0.1mmol), copper powder (0.05mmol), raise to 110°C Afterwards, react for 2.5 hours. After the reaction, the solvent was spun off, and the mixture was sequentially separated by column chromatography using dichloromethane and ethyl acetate as eluents to obtain compound (II) as pale yellow crystals.

[0027]

[0028] Compound (II): Pale yellow crystal, yield 62.0%, melting point 174-176°C. UV spectrum see image 3 ; H NMR spectrum Figure 4 : 1 HNMR (600MHz, CDCl 3 ):2.47(s,-CH 3 ,3H),3.84(s,N-CH 3 ,3H), 7.00~7.22(m,ArH,4H), 7.23~7.45(m,ArH,4H), 7.46~7.51(m,ArH,5H), 7.55~7.65(m,ArH,5H).

[0029] The following examples are the curing performance of compound (I) or compound (II) of th...

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Abstract

The invention relates to an aromatic sulfonium salt compound and in particular relates to triaryl sulfonium salt containing 1-methyl-2-phenyl indole skeleton as well as a preparation method and application thereof. The preparation method of the triaryl sulfonium salt containing 1-methyl-2-phenyl indole skeleton comprises that 1-methyl-2-phenyl indole is taken as a raw material, diphenyl disulfide is taken as a sulfur source, a C-S bond coupling reaction is carried out for synthesizing aromatic sulfide, then a reaction is carried out on the aromatic sulfide and diaryl iodonium salt under the copper-catalyzed condition, so that the triaryl sulfonium salt containing 1-methyl-2-phenyl indole skeleton is obtained. Ultraviolet absorption wavelength of the triaryl sulfonium salt containing 1-methyl-2-phenyl indole skeleton can be more than 290nm in a red shift manner, the triaryl sulfonium salt containing 1-methyl-2-phenyl indole skeleton can be applied to an ultraviolet curing composition, especially ultraviolet curing coating, as a positive ion photoinitiator and has good reaction activity, surface curability and solubility, and the special group, namely 1-methyl-2-phenyl indole, is introduced, so that photo-initiation performance of the triaryl sulfonium salt containing 1-methyl-2-phenyl indole skeleton is effectively improved.

Description

technical field [0001] The present invention relates to a triaryl sulfonium salt, specifically a triaryl sulfonium salt containing a 1-methyl-2-phenylindole skeleton and a preparation method thereof, and the salt is used as a photoinitiator in an ultraviolet light curing composition, especially Is the application of UV curing coatings. Background technique [0002] Photocuring technology is a rapidly developing green new technology. The photocuring system is generally composed of unsaturated resin, reactive diluent, photoinitiator and auxiliary agent. Among them, the photoinitiator is the key component, which generates active free radicals or cations after absorbing ultraviolet light, triggers the double bond opening polymerization of the unsaturated group in the resin, and the ring-opening polymerization of the epoxy resin to quickly cure and form a film. Compared with free radical photoinitiators, although the curing speed of cationic photoinitiators is slow, the shrinka...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D209/30C08F2/48C09D163/10C09D7/12
CPCC07D209/30C08F2/48C08K5/36C09D7/63C09D163/10
Inventor 张变香田怀东陈凯
Owner 山西亮龙涂料有限公司
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