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Active energy ray-curable composition for optical material, cured product, and production methods for active energy ray-curable composition and cured product

A technology of active energy rays and curable compositions, applied in optics, optical components, instruments, etc., can solve the problems that cannot be used in optical materials that require high transparency, and achieve low viscosity and excellent active energy ray curability Effect

Inactive Publication Date: 2013-08-07
KANEKA CORP
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] The inventors of the present invention have disclosed a polymer whose main chain is a vinyl polymer obtained by living radical polymerization and which has a (meth)acryloyl group at the end (Patent Documents 1 to 3), although these The cured product of the polymer has excellent rubber properties and heat resistance, etc., but because it is colored yellow and is colored under heating conditions, it cannot be used in optical materials requiring high transparency in many cases

Method used

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  • Active energy ray-curable composition for optical material, cured product, and production methods for active energy ray-curable composition and cured product
  • Active energy ray-curable composition for optical material, cured product, and production methods for active energy ray-curable composition and cured product
  • Active energy ray-curable composition for optical material, cured product, and production methods for active energy ray-curable composition and cured product

Examples

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Embodiment

[0282] The present invention will be described in more detail by enumerating specific examples below, but the present invention is not limited to the following examples.

[0283] In the following examples, "number average molecular weight" and "molecular weight distribution (ratio of weight average molecular weight to number average molecular weight)" were calculated by the standard polystyrene conversion method using gel permeation chromatography (GPC). Here, a column packed with polystyrene cross-linked gel (Shodex GPC K-804 and K-802.5, manufactured by Showa Denko Co., Ltd.) was used as a GPC column, and chloroform was used as a GPC solvent.

[0284] In the following examples, "the number of (meth)acryloyl groups introduced per 1 polymer molecule" is given by 1 H-NMR analysis and calculation of number average molecular weight obtained by GPC. (in, 1 H-NMR was measured at 23° C. using ASX-400 manufactured by Bruker Co., Ltd., using deuterated chloroform as a solvent. )

...

Synthetic example 1）

[0309]

[0310] With cuprous bromide as the catalyst, pentamethyldiethylenetriamine as the ligand, 2,5-dibromodiethyl adipate as the initiator, and n-butyl acrylate as the monomer, in (n-butyl acrylate ester) / (diethyl-2,5-dibromoadipate) ratio of 80 to obtain bromine-terminated poly(n-butyl acrylate).

[0311] This polymer was dissolved in N,N-dimethylacetamide, potassium acrylate was added, and heated and stirred at 70°C in a nitrogen atmosphere. After distilling off N,N-dimethylacetamide in the mixture under reduced pressure, butyl acetate was added to the residue, and insoluble components were removed by filtration. Butyl acetate in the filtrate was distilled off under reduced pressure to obtain poly(n-butyl acrylate) having acryloyl groups at both terminals (polymer [P1]).

[0312] The number average molecular weight of the polymer [P1] was 12,000, the molecular weight distribution was 1.2, and the average number of terminal acryloyl groups was 1.8.

[0313] 4 g of a 5...

Synthetic example 2）

[0316]

[0317] With cuprous bromide as the catalyst, pentamethyldiethylenetriamine as the ligand, ethyl α-bromobutyrate as the initiator, and n-butyl acrylate as the monomer, in (n-butyl acrylate) / ( α-Bromobutyric acid ethyl ester) is polymerized under the condition of a ratio of 40 to obtain bromine-terminated poly(n-butyl acrylate).

[0318] This polymer was dissolved in N,N-dimethylacetamide, potassium acrylate was added, and heated and stirred at 70°C in a nitrogen atmosphere. After distilling off N,N-dimethylacetamide in the mixture under reduced pressure, butyl acetate was added to the residue, and insoluble components were removed by filtration. Butyl acetate in the filtrate was distilled off under reduced pressure to obtain poly(n-butyl acrylate) having an acryloyl group at one end.

[0319] To 800 g of the obtained polymer was added 4 g of a 50% aqueous hydrogen peroxide solution and stirred in air for about 10 minutes. After further stirring in air at 100°C for ...

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Abstract

Provided are an active energy ray-curable composition for an optical material that has excellent low viscosity, shelf life, low foamability, low-temperature curability, low-warping performance, deep curability, heat-resistant and light-resistant transparency, rubber properties, cracking resistance, moisture permeation resistance and designability; a cured product; and production methods for obtaining the active energy ray-curable composition and the cured product. The active energy ray-curable composition for the optical material comprises (A) a vinyl polymer which has, per molecule, at least one methacryloyl group represented by the general formula (1) -OC(O)C(Ra)=CH2(1) (where Ra is a hydrogen atom or C1-C20 organic group) is produced by living radical polymerization, and has a color difference delta E* of 10 or less; (B) a light-induced radical polymerization initiator; and (C) at least one antioxidant selected from the group consisting of hindered phenol antioxidants, hindered amine antioxidants, and phosphorus antioxidants.

Description

technical field [0001] The present invention relates to an active energy ray curable composition for optical materials, a cured product, and a method for producing the same. Background technique [0002] In optical materials used for LEDs, solar cells, and flat panel display devices, etc., materials with high transparency, heat-resistant transparency, and light-resistant transparency are used. In order to protect components and fine circuits, the material is also required to have impact resistance, moisture permeability resistance, and the like that can withstand the use environment. In addition, in terms of manufacturing process, low viscosity, excellent productivity, less curing shrinkage, and no warping of the substrate are required. [0003] As optical materials for LEDs, hard transparent epoxy resins produced with acid anhydride curing agents, soft silicone resins mainly composed of methyl polysiloxane, and soft silicone resins mainly composed of phenyl polysiloxane ar...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08F20/10C08F299/00C08F8/00C08F290/04
CPCC08F8/00C08F220/18C09D4/06G02B1/04C08F293/005C08F2810/40C08F2/48C08F2438/00C08F2438/01C08K5/005C08F220/1809C08F220/1812C08F220/1818C08F120/18
Inventor 一柳典克小谷准
Owner KANEKA CORP
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