Soluble polyfunctional (meth)acrylate copolymer having alicyclic structure, curable resin composition, and cured product

An acrylate, multifunctional technology, applied in the field of soluble multifunctional (meth)acrylate copolymer with alicyclic structure, curable resin composition and cured product, can solve the strength, heat resistance of resin composition Reduction and other problems, to achieve the effects of improved adhesion, low dispersion, and high light transmittance

Active Publication Date: 2016-03-16
NIPPON STEEL CHEM &MATERIAL CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the technique disclosed in this patent document has the disadvantage that only one or less vinyl compounds derived from vinyl groups 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 molecular weight modifier cannot sufficiently impart functions from the terminal group
Furthermore, there is also the following disadvantage: the self-curing copolymer obtained by the technology disclosed therein forms a thermosetting resin composition in a resin composition with an epoxy resin, but does not form a thermosetting resin composition with an acrylate resin. Curing reaction, thus causing a decrease in the strength and heat resistance of the compounded resin composition

Method used

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  • Soluble polyfunctional (meth)acrylate copolymer having alicyclic structure, curable resin composition, and cured product
  • Soluble polyfunctional (meth)acrylate copolymer having alicyclic structure, curable resin composition, and cured product
  • Soluble polyfunctional (meth)acrylate copolymer having alicyclic structure, curable resin composition, and cured product

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0149] Dimethylol tricyclodecane diacrylate (DMTCD) 1.6 moles (463.2ml), tricyclo[5.2.1.02,6]dec-8-yl methacrylate 1.2 moles (254.2ml), 1,4 -Butanediol diacrylate (BDDA) 1.2 moles (226.3ml), 2,4-diphenyl-4-methyl-1-pentene (αMSD) 0.4 moles (95.5ml), tert-dodecyl Put 2.4 moles (564.8ml) of mercaptan (TDM) and 600ml of toluene into a 3.0L reactor, and add 40mmol (11.5g) of tert-butyl peroxy-2-ethylhexanoate at 90°C to react 2 Hours and 45 minutes. 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 copolymer. The obtained copolymer was washed with hexane, separated by filtration, dried, and weighed to obtain 536.4 g of copolymer A (yield: 73.2 wt %).

[0150] Mw of the obtained copolymer A was 34200, Mn was 5620, and Mw / Mn was 6.1. by carrying out 13 C-NMR, 1 H-NMR analysis and elemental analysis, copolymer A contains a total of 39.6 mol% of structural units (1) derived ...

Embodiment 2

[0160] 2.64 moles (764.3ml) of dimethyloltricyclodecane diacrylate, 0.24 moles (47.2ml) of tricyclo[5.2.1.02,6]dec-8-yl acrylate (DCPA), 1,4-butyl Diol diacrylate 0.96 moles (181.0ml), 2-hydroxypropyl acrylate (HOP-A) 0.96 moles (118.5ml), 2,4-diphenyl-4-methyl-1-pentene 0.48 moles ( 114.6ml), 3.12 moles of tert-dodecylmercaptan (734.3ml), and 720ml of toluene are dropped into a 3.0L reactor, and 62mmol (13.9g) of peroxy-2-ethylhexanoic acid tertiary butyl ester and allowed to react for 2 hours and 30 minutes. 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, separated by filtration, dried, and weighed to obtain 517.2 g of a copolymer B (yield: 71.5 wt %).

[0161] Mw of the obtained copolymer B was 39500, Mn was 7240, and Mw / Mn was 5.5. by carrying out 13 C-NMR, 1 H-NMR analysis and elemental analysis, copolymer ...

Embodiment 3～8 and comparative example 1～4

[0170] Using various monofunctional (meth)acrylates and bifunctional acrylates, polymerization was carried out in the same manner as in Example 1 with the raw material composition shown in Table 1.

[0171] Table 1 shows the amount of raw materials used in the reaction, and Table 2 shows the test results of the copolymer and its cured product. 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 represented by mole and weight (g), and the form of record is mole / g. In addition, the mole fraction (MR) calculated the sum total of (a) component and (b) component as 100.

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Abstract

The present invention provides a novel polyfunctional (meth)acrylate copolymer and a curable resin composition using the copolymer, which have excellent optical properties such as low dispersion and high light transmittance, and are required for optical lens and prism materials. It has excellent balance of various properties, and maintains high optical properties without branching of the refractive index even under severe actual use conditions such as hot and humid conditions. A copolymer comprising a monofunctional (meth)acrylate (a) having an alicyclic structure, a bifunctional (meth)acrylate (b), 2,4-diphenyl-4-methyl- A copolymer obtained by copolymerizing the components of 1-pentene (c) and thiol compound (d), which has a reactive (meth)acrylate group derived from bifunctional (meth)acrylate (b) in the side chain , a copolymer having a terminal structural unit derived from 2,4-diphenyl-4-methyl-1-pentene (c) and a thiol compound (d); and a curable resin composition comprising the copolymer.

Description

technical field [0001] The present invention relates to a product having excellent optical properties such as low dispersion and high light transmittance, heat resistance, and processability, and also optical properties under severe actual use conditions such as humid and hot conditions, low water absorption, and good release during molding. Soluble polyfunctional (meth)acrylate copolymer having an alicyclic structure with improved moldability and precise mold transferability, and curable resin composition containing the soluble polyfunctional (meth)acrylate copolymer, Cures and optics. 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. Generally, since there are many types of monomers having unsaturated bonds, the variety of types of resins to be obtained is also remarkable. However, there are relatively few types o...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C08F222/14C08F220/18C08F220/28C08F2/48C08F2/38G02B1/04
CPCC08F2/44C08F212/34C08F220/18C08F220/20C08F228/02C08F220/1806C08F220/1811C08F220/281C08F222/1025G02B1/041
Inventor 川边正直林健太郎和佐野次俊
Owner NIPPON STEEL CHEM &MATERIAL CO LTD
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