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Soluble polyfunctional (meth) acrylic ester copolymer, and method for production thereof, curable resin composition and cured product

A technology of curable resin and acrylate, applied in instruments, optics, optical components, etc., can solve the problems of insufficient heat resistance, reduced strength and heat resistance of the resin composition, etc., and achieve improved adhesion and heat resistance retention. The effect of improved performance and excellent optical properties

Active Publication Date: 2012-02-15
NIPPON STEEL CHEMICALL &MATERIAL CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, in the technology disclosed in this patent document, there is a disadvantage that only one or less polyfunctional vinyl compounds derived from molecular weight can be introduced into the polymer chain because no difunctional or higher vinyl compound having a plurality of vinyl groups is added during polymerization. The terminal group of the regulator cannot sufficiently impart the function from the terminal group
Furthermore, in this patent publication, there is also the following disadvantage: the self-curing copolymer obtained by the disclosed technology forms a thermosetting resin composition in a resin composition with an epoxy resin, but in a resin composition with an acrylate resin During the period, no curing reaction is caused, so the strength and heat resistance of the compounded resin composition are reduced
In addition, when subjected to severe heat history during high-temperature reflow, the heat resistance for shape maintenance is insufficient, and it is necessary to improve the optical characteristics after heat history

Method used

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  • Soluble polyfunctional (meth) acrylic ester copolymer, and method for production thereof, curable resin composition and cured product
  • Soluble polyfunctional (meth) acrylic ester copolymer, and method for production thereof, curable resin composition and cured product
  • Soluble polyfunctional (meth) acrylic ester copolymer, and method for production thereof, curable resin composition and cured product

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0168] 3.2mol (926.5ml) of dimethyloltricyclodecane diacrylate, 8.0mol (1814.1ml) of isobornyl methacrylate, and 4.8 mol (1814.1ml) of methacrylate-2-hydroxypropyl mol (645.5ml), 2,4-diphenyl-4-methyl-1-pentene 14.8mol (1145.9ml), toluene 2400ml, add 240mmol of benzoyl peroxide at 90°C to react 6 Hour. After the polymerization reaction was stopped by cooling, the reaction mixture was poured into a large amount of hexane at room temperature to precipitate a polymer. The obtained polymer was washed with hexane, filtered, dried, and weighed to obtain 1392.6 g of a copolymer A (yield: 40.5 wt%).

[0169] Mw of the obtained copolymer A was 8950, Mn was 3470, and Mw / Mn was 2.58. by carrying out 13 C-NMR, 1 H-NMR analysis and elemental analysis, copolymer A contains a total of 18.2 mol% of structural units derived from dimethyloltricyclodecane diacrylate, a total of 51.1 mol% of structural units derived from isobornyl methacrylate, and 30.7 mol% Structural unit derived from 2-hy...

Embodiment 2～13 and comparative example 1～6

[0177] Polymerization was performed in the same manner as in Example 1 with the raw material composition shown in Table 1 using various bifunctional acrylates and monofunctional (meth)acrylates.

[0178] Tables 1 and 2 show the amounts of raw materials used in the reaction, and Tables 3 and 4 show the test results of the copolymers and their cured products. Unless otherwise specified, other reaction conditions and measurement conditions are the same as in Example 1. In Table 1, the amount of raw materials used is expressed in mol and weight (g), and the recorded form is mol / g.

[0179] The apostrophes used in the tables are shown below.

[0180] DMTCD: Dimethyloltricyclodecane diacrylate (c)

[0181] BDDA: 1,4-Butanediol diacrylate (c)

[0182] HOP: 2-hydroxypropyl methacrylate (b)

[0183] HO: 2-hydroxyethyl methacrylate (b)

[0184] CD570: Partially ethoxylated 2-hydroxyethyl methacrylate (b)

[0185] IBOMA: Isobornyl Methacrylate (a)

[0186] DCPM: tricyclo[5.2.1.02,...

Synthetic example 1

[0215] Copolymer A was obtained in the same manner as in Example 1.

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Abstract

The invention provides a copolymer which is excellent in optical characteristics, such as low in color dispersion and high in light transmission rate, has excellent balanced characteristics required by optical lenses and prism material, and can cause no refractive index change under real usage condition such as a damp and hot situation, and curable resin composition comprising the same, particularly to a soluble polyfunctional (meth) acrylic ester copolymer and a curable resin composition comprising the same. The soluble polyfunctional (meth) acrylic ester copolymer is obtained by conducting copolymerization on a single functional (meth) acrylic ester (a) containing a fat ring type structure, a single functional (meth) acrylic ester (b) containing a hydroxyl group, a bifunctional (meth) acrylic ester (c) and a 2, 4-diphenyl-methyl-1-pentene (d). A side chain of the soluble polyfunctional (meth) acrylic ester copolymer comprises a reactive (meth) acrylic ester from (c), and the end of the soluble polyfunctional (meth) acrylic ester copolymer comprises a structural unit from (d).

Description

technical field [0001] The present invention relates to optical properties such as low color dispersion and high light transmittance, heat resistance, and processability, and optical properties under severe actual use conditions such as humid and hot conditions, low water absorption, and adhesion to inorganic materials. A soluble polyfunctional (meth)acrylate copolymer having an alicyclic structure and an alcoholic hydroxyl group having improved compatibility, a method for producing the same, a curable resin composition using the same, and a cured product. Background technique [0002] Many monomers with reactive unsaturated bonds can form multimers by selecting unsaturated bond breaking, catalysts that cause chain reactions, and appropriate reaction conditions. In general, there are many types of monomers having unsaturated bonds, and thus the variety of resins to be obtained is also remarkable. However, there are relatively few types of monomers capable of obtaining a hig...

Claims

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Application Information

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IPC IPC(8): C08F220/18C08F220/28C08F222/20C08F222/14C08F212/06C08F2/38C08F2/48C08F265/04C08F292/00C08L51/00C08L51/10
CPCC08F2/50C08F220/10C08F220/18C08F222/20C08K3/36C08L33/08C08L33/10C08L2201/02C08L2201/10G02B1/041G02B5/04
Inventor 川边正直宫田刚
Owner NIPPON STEEL CHEMICALL &MATERIAL CO LTD
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