Acrylic acid type thiosulfonate-based monomer with high refractive index and synthesis method of acrylic acid type thiosulfonate-based monomer

A technology containing thiosulfonate and high refractive index, applied in organic chemistry and other fields, can solve problems such as high molar refractive index dispersion, and achieve high transmittance, simple synthesis process, and low viscosity

Inactive Publication Date: 2015-07-29
HEFEI UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Halogen and heavy metal ions are rarely used due to their high toxicity, while benzene rings, fused rings, and heterocycles have high molar refractive indices but cause high dispersion

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0019] The 250mL four-neck flask was fixed in an ice-water bath and nitrogen gas was passed. Add 50 mL of dichloromethane and 0.1 mol of 2-mercaptothiophene to the flask, and stir to dissolve. Then 0.12 mol of triethylamine and 0.5 g of benzyltriethylammonium chloride were added. Mix 0.15mol p-styrenesulfonyl chloride and 30mL dichloromethane and drop them into the reaction system under vigorous stirring through a separatory funnel for 30 minutes. After the dropwise addition, continue stirring for 2h to stop the reaction. Pour out the reactant, first pass through NaHCO 3 Wash once with aqueous solution, and then wash with distilled water until triethylamine hydrochloride is removed. After removing water with anhydrous calcium chloride, the solvent, residual triethylamine and p-styrenesulfonyl chloride are distilled off under reduced pressure to obtain an acrylic acid-type high-refractive-index monomer containing thiosulfonate groups.

Embodiment 2

[0021] The 250mL four-neck flask was fixed in an ice-water bath and nitrogen gas was passed. Add 50mL N,N-dimethylformamide and 0.1mol 2-mercaptothiophene to the flask, stir to dissolve. Then 0.15 mol of pyridine and 0.8 g of tetrabutylammonium bromide were added. Mix 0.2mol p-styrenesulfonyl chloride and 30mL N,N-dimethylformamide and drop them into the reaction system under vigorous stirring through a separatory funnel for 30 minutes. After the dropwise addition, continue stirring for 2h to stop the reaction. Pour out the reactant, first pass through NaHCO 3 Wash once with aqueous solution, and then wash with distilled water until pyridine hydrochloride is removed. After removing water with anhydrous calcium chloride, the solvent and residual pyridine and p-styrenesulfonyl chloride are distilled off under reduced pressure to obtain an acrylic acid-type high-refractive-index monomer containing thiosulfonate groups.

Embodiment 3

[0023] The 500mL four-neck flask was fixed in an ice-water bath and nitrogen gas was passed. Add 50 mL of dichloromethane and 0.1 mol of 2-mercaptothiophene to the flask, and stir to dissolve. An aqueous solution containing 0.12 mol KOH and 0.5 g benzyltriethylammonium chloride were then added. Mix 0.15mol p-styrenesulfonyl chloride and 30mL dichloromethane and drop them into the reaction system under vigorous stirring through a separatory funnel for 30 minutes. After the dropwise addition, continue stirring for 2h to stop the reaction. Pour out the reactant, separate the organic layer with a separatory funnel, and pass through NaHCO 3 Wash once with aqueous solution, and then wash with distilled water until neutral. After removing water with anhydrous calcium chloride, the solvent and residual p-styrenesulfonyl chloride are distilled off under reduced pressure to obtain an acrylic acid-type high-refractive-index monomer containing thiosulfonate groups.

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Abstract

The invention relates to an acrylic acid type optical monomer, in particular to an acrylic acid type thiosulfonate-based monomer with a high refractive index and a preparation method of the acrylic acid type thiosulfonate-based monomer. Under the conditions of protecting atmosphere and the temperature of 0-5 DEG C, a solvent and 2-sulfhydryl thiophene are added to a reaction container and stirred, a phase transfer catalyst, an acid-binding agent and p-styrenesulfonyl chloride are added for a reaction, an organic layer is separated and washed, reduced pressure distillation is performed after water removal, and the acrylic acid type thiosulfonate-based monomer is obtained. The monomer contains a double-bond structure and has higher refractive index and transmissivity; the monomer contains a thioether group, a sulfuryl group, a benzene ring, a heterocyclic ring and other structures, so that the refractive index of the monomer is about 1.68 and far higher than that of conventional optical resin; the monomer has higher refractive index and lower viscosity, is easy to cure, can be used as a priming coat and a hardening layer in a transparent conductive film and other optical products requiring higher refractive index and has higher utilization value.

Description

technical field [0001] The invention relates to an acrylic type optical monomer, in particular to an acrylic type high refractive index monomer containing a thiosulfonate group and a preparation method thereof. Background technique [0002] Refractive index is one of the most basic and important indicators of optical materials. Increasing the refractive index can effectively reduce the thickness and radius of curvature of the lens. LED lamp sealants, light-curing erasing adhesives and hardened coatings that eliminate touch screen ITO circuits all require resins with a higher refractive index (usually above 1.65). Traditional optical resins, such as polymethyl methacrylate, polyethylene terephthalate, etc., have good optical and mechanical properties, but their refractive index is usually below 1.6. [0003] The method of increasing the refractive index of resin is usually to introduce groups with higher molar refractive index and lower molecular volume into polymer molecule...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D333/34
CPCC07D333/34
Inventor 徐卫兵毛亚俊黄暄暄周正发马海红任凤梅
Owner HEFEI UNIV OF TECH
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