Low-viscosity agent of high-refractive-index polymerizable compound and polymerizable composition containing the same

A technology of polymeric compounds and polymeric compositions, applied in instruments, optical components, optics, etc., can solve problems such as increased viscosity of materials, high electron density, and deterioration of operability, and achieve low Abbe number, high refractive index, The effect of excellent optical characteristics

Active Publication Date: 2022-07-05
NISSAN CHEM IND LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] Materials characterized by a low Abbe number require high transparency in addition to a high refractive index, but if these optical properties are improved, the viscosity of the material tends to increase, resulting in a significant deterioration in handling properties.
Generally, this is due to the high electron density of the components contributing to the high refractive index, so it is easy to increase the viscosity, and the deterioration of workability can be said to be an essential problem in the development of low Abbe materials.

Method used

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  • Low-viscosity agent of high-refractive-index polymerizable compound and polymerizable composition containing the same
  • Low-viscosity agent of high-refractive-index polymerizable compound and polymerizable composition containing the same
  • Low-viscosity agent of high-refractive-index polymerizable compound and polymerizable composition containing the same

Examples

Experimental program
Comparison scheme
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Embodiment

[0218] Hereinafter, although an Example is given and this invention is demonstrated more concretely, this invention is not limited to the following Example.

[0219] In addition, in the Example, the apparatus and conditions used for the preparation of a sample and the analysis of a physical property are as follows.

[0220] (1) Spin coater

[0221] Device: Cee (registered trademark) 200X manufactured by Brewer Science

[0222] (2) UV exposure

[0223] Apparatus: Intermittent UV irradiation apparatus (high-pressure mercury lamp 2kW x 1 lamp) manufactured by Aigurafex Co., Ltd.

[0224] (3) 1 H NMR spectroscopy

[0225] Installation: AVANCE III HD by Bruker

[0226] Measurement frequency: 500MHz

[0227] Solvent: CDCl 3

[0228] Internal reference: tetramethylsilane (δ=0.00ppm)

[0229] (4) Gel permeation chromatography (GPC)

[0230] Device: Prominence (registered trademark) GPC system manufactured by Shimadzu Corporation

[0231] Column: Showa Denko Co., Ltd. Shodex...

manufacture example 1

[0267] [Production Example 1] Production of dimethoxy(phenanthren-9-yl)(4-vinylphenyl)silane (SPeDMS)

[0268] To a 1 L reaction flask equipped with a condenser, 15.7 g (0.65 mol) of magnesium chips [manufactured by Kanto Chemical Co., Ltd.] was put, and the air in the flask was replaced with nitrogen gas using a nitrogen balloon. A mixture of 151.2 g (0.58 mol) of 9-bromophenanthrene [manufactured by Tokyo Chemical Industry Co., Ltd.] and 518 g of THF was added dropwise thereto over 1 hour at room temperature (about 23° C.), and the mixture was further stirred for 1 hour to prepare a Grignard reagents.

[0269] In a 2L reaction flask, 131.9 g (0.58 mol) of STMS and 259 g of THF were added, and the air in the flask was replaced with nitrogen using a nitrogen balloon. The above-mentioned Grignard reagent was added dropwise thereto under reflux (about 66° C.) over 30 minutes, and the mixture was further refluxed for 24 hours. THF was distilled off from the reaction mixture und...

manufacture example 2

[0271] [Production example 2] Production of naphth-2-ylmethyl acrylate (NMA)

[0272] In a 200 mL reaction flask, 25.0 g (0.158 mol) of 2-naphthylmethanol [manufactured by Tokyo Chemical Industry Co., Ltd.] and 158 g of THF were added, and the air in the flask was replaced with nitrogen using a nitrogen balloon, followed by cooling to 0°C. To this, 17.58 g (0.174 mol) of triethylamine [manufactured by Tokyo Chemical Industry Co., Ltd.] and 15.73 g (0.174 mol) of acryloyl chloride [manufactured by Tokyo Chemical Industry Co., Ltd.] were added, and the mixture was stirred at room temperature (about 23°C). 1 hour. To this reaction mixture was added 158 g of water, and the resultant was extracted with 158 g of ethyl acetate. The solvent was distilled off under reduced pressure from the organic layer using an evaporator to obtain a crude product. The crude product was purified by silica gel chromatography (hexane / ethyl acetate=9 / 1 (mass ratio)) to obtain 21.5 g (yield 64%) of napht...

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Abstract

An object of the present invention is to provide a high-refractive-index low-viscosity agent and a polymerizable composition containing the low-viscosity agent with little loss of refractive index during blending, breaking the compromise between lowering Abbe and lowering viscosity. The solution is a method of using the following compound as a low-viscosity reducing agent for a high-refractive-index polymerizable compound. The material state of the compound at 1013.25hPa and 23°C is solid, the melting point is less than 100°C, and the viscosity at 100°C is 10 mPa·s or less, and the Abbe number of the cured product at D line (589.3 nm) is 23 or less, the above-mentioned high refractive index polymerizable compound has at least one polymerizable double bond, and its cured product is at D line (589.3 nm) The refractive index in nm) is 1.60 or more.

Description

technical field [0001] The present invention relates to a low-viscosity reducing agent, and more specifically, to a low-viscosity reducing agent useful as a high-refractive-index diluent capable of reducing the viscosity of a polymerizable optical material having a high refractive index. Background technique [0002] Resin lenses are used in electronic devices such as mobile phones, digital cameras, and in-vehicle cameras, and are required to have excellent optical properties according to the purpose of the electronic devices. In addition, depending on the usage form, high durability such as heat resistance and weather resistance, and high productivity that can be molded with good yield are required. As a resin lens material satisfying such requirements, thermoplastic transparent resins such as polycarbonate resins, cycloolefin polymers, and methacrylic resins are used, for example. [0003] In addition, in recent years, in order to improve the yield, production efficiency,...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): G02B1/04C08F20/10C08F230/08
CPCC08F20/10G02B1/04C08F2/44C08F2/48C08F220/26C08K5/01C08K5/5415G02B1/041C08F230/085
Inventor 加藤拓首藤圭介长泽伟大
Owner NISSAN CHEM IND LTD
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