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Low-viscosity agent for polymerizable compound having high refractive index and polymerizable composition containing same

A technology of polymeric compounds and polymeric compositions, which can be used in instruments, optics, optical components, etc., and can solve problems such as deterioration of operability, increased viscosity of materials, and high viscosity

Active Publication Date: 2019-01-04
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 for polymerizable compound having high refractive index and polymerizable composition containing same
  • Low-viscosity agent for polymerizable compound having high refractive index and polymerizable composition containing same
  • Low-viscosity agent for polymerizable compound having high refractive index and polymerizable composition containing same

Examples

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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 a following Example.

[0219] In addition, in Examples, the apparatus and conditions used for preparation of a sample and 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] Device: Intermittent UV irradiation device manufactured by Aigraphy Co., Ltd. (high pressure mercury lamp 2kW x 1 lamp)

[0224] (3) 1 H NMR spectrum

[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: Shodex (registered trademark) GPC KF-804L and GPC ...

manufacture example 1

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

[0268] Into 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 placed, 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 at room temperature (about 23° C.) over 1 hour, and stirred for further 1 hour to prepare Grignard reagent.

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

manufacture example 2

[0271] [Production Example 2] Production of Naphthalene-2-ylmethyl Acrylate (NMA)

[0272] Into 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. 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 thereto, and stirred at room temperature (about 23° C.) 1 hour. 158 g of water was added to the reaction mixture, and the product was extracted with 158 g of ethyl acetate. The solvent was distilled off from the organic layer under reduced pressure 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 of naphthalene-2-ylmethyl acryla...

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Abstract

To provide a low-viscosity agent having a high refractive index and a polymerizable composition containing the same such that the tradeoff between a lower Abbe number and a lower viscosity is eliminated and the loss of a refractive index is decreased when the agent and composition are combined. Provided is a method for using a compound as a low-viscosity agent for a polymerizable compound having ahigh refractive index. The compound, which is in the solid state at 23 DEG C under 1013.25 hPa and has a melting point less than 100 DEG C, has a viscosity at 100 DEG C of less than or equal to 10 mPa.s and an Abbe number in the D-line (589.3 nm) of the cured product thereof of less than or equal to 23. The polymerizable compound having a high refractive index has at least one polymerizable double bond and a refractive index in the D-line (589.3 nm) of the cured product thereof is greater than or equal to 1.60.

Description

technical field [0001] The present invention relates to a viscosity-lowering agent. Specifically, it relates to a viscosity-lowering 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 car cameras, and are required to have excellent optical characteristics corresponding to the purpose of the electronic devices. In addition, depending on the form of use, high durability such as heat resistance and weather resistance, and high productivity that can be molded with good yield are required. As materials for resin lenses satisfying such requirements, for example, thermoplastic transparent resins such as polycarbonate resins, cycloolefin polymers, and methacrylic resins are used. [0003] In addition, in recent years, in the manufacture of resin lenses, in order to imp...

Claims

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Application Information

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Patent Type & Authority Applications(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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