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Soluble polyfunctional (methyl) acrylate copolymer with alicyclic ring structure, curable resin composition and cured product

A curable resin, acrylate technology, applied in instruments, optics, optical components, etc., can solve the problems of reducing the strength and heat resistance of the resin composition, and achieve improved adhesion, low dispersion, and high light transmittance. Effect

Active Publication Date: 2012-09-19
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 (methyl) acrylate copolymer with alicyclic ring structure, curable resin composition and cured product
  • Soluble polyfunctional (methyl) acrylate copolymer with alicyclic ring structure, curable resin composition and cured product
  • Soluble polyfunctional (methyl) acrylate copolymer with alicyclic ring 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 invention provides a novel soluble polyfunctional (methyl) acrylate copolymer, and a curable resin composition using the copolymer with excellent optical characteristics such as low dispersion, high light transmittance, and various balance characteristics required by an optical lens / prism material; no generation of branch of refractive index, and maintenance of high optical properties even though in a rigorous practical using condition such as damp heat condition. The copolymer is obtained by copolymerizing single functional (methyl) acrylate (a), dual functional (methyl) acrylate (b), 2, 4-diphenyl-4-methyl-1-pentene (c) and a thiol compound (d), wherein the side chain of the copolymer comprises a reactive (methyl) acrylate group from the dual functional (methyl) acrylate (b), the end comprises structural units from the 2, 4-diphenyl-4-methyl-1-pentene (c) and the thiol compound (d). The curable resin composition contains 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 Applications(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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