Soluble polyfunctional (meth)acrylate copolymer, method for producing same, curable resin composition, and cured product

An acrylate and acrylate-based technology, applied in the direction of instruments, optics, optical components, etc., can solve the problems of resin composition strength, heat resistance reduction, and insufficient heat resistance, and achieve improved adhesion and heat resistance retention Performance improvement and excellent optical properties

Active Publication Date: 2016-03-02
NIPPON STEEL CHEM &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)acrylate copolymer, method for producing same, curable resin composition, and cured product
  • Soluble polyfunctional (meth)acrylate copolymer, method for producing same, curable resin composition, and cured product
  • Soluble polyfunctional (meth)acrylate copolymer, method for producing same, curable resin composition, and cured product

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0168] Put 3.2 mol (926.5 ml) of dimethylol tricyclodecane diacrylate, 8.0 mol (1814.1 ml) of isobornyl methacrylate, and 4.8 hydroxypropyl methacrylate into a 10.0L reactor. mol (645.5ml), 1,4.8mol (1145.9ml) of 2,4-diphenyl-4-methyl-1-pentene, 2400ml of toluene, 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 the polymer. The obtained polymer was washed with hexane, filtered, dried, and weighed to obtain 1392.6 g of copolymer A (yield: 40.5 wt%).

[0169] The Mw of the obtained copolymer A was 8950, Mn was 3470, and Mw / Mn was 2.58. Go through 13 C-NMR, 1 According to H-NMR analysis and elemental analysis, copolymer A contains a total of 18.2 mol% of structural units derived from dimethylol tricyclodecane diacrylate, a total of 51.1 mol% of structural units derived from isobornyl methacrylate, and 30.7 mol% A struc...

Embodiment 2～13 and comparative example 1～6

[0177] Using various bifunctional acrylates and monofunctional (meth)acrylates, polymerization was carried out in the same manner as in Example 1 with the raw material composition shown in Table 1.

[0178] Tables 1 and 2 show the amount of raw materials used in the reaction, and Tables 3 and 4 show 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 expressed in mol and weight (g), and the stated format is mol / g.

[0179] The ellipsis used in the table is shown below.

[0180] DMTCD: Dimethylol tricyclodecane 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[5.2.1.02,6]dec-8-yl methacrylate (...

Synthetic example 1

[0215] In the same manner as in Example 1, copolymer A was obtained.

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Abstract

The present invention provides excellent optical properties such as low color dispersion and high light transmittance, excellent balance of various properties required in optical lens and prism materials, and no refractive index changes even under severe actual use conditions such as humid and hot conditions. A variable copolymer and a curable resin composition containing the same. It is a soluble multifunctional (meth)acrylate copolymer and a curable resin composition containing it. The soluble multifunctional (meth)acrylate copolymer will contain monofunctional (meth) Acrylate (a), monofunctional (meth)acrylate (b) having an alcoholic hydroxyl group, bifunctional (meth)acrylate (c), and 2,4-diphenyl-4-methyl-1- The copolymer obtained by copolymerizing the pentene (d) component has a reactive (meth)acrylate group derived from (c) in the side chain and has a structural unit derived from (d) in the terminal.

Description

Technical field [0001] The present invention relates to excellent 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 heat conditions, low water absorption, and closeness with inorganic materials. A soluble polyfunctional (meth)acrylate copolymer having an alicyclic structure and an alcoholic hydroxyl group with improved synthesizing properties, a method for producing the same, and a curable resin composition and cured product using the same. Background technique [0002] Many monomers with reactive unsaturated bonds can form multimers by selecting a catalyst that breaks the unsaturated bonds, causing a chain reaction, and appropriate reaction conditions. Generally speaking, there are many types of monomers having unsaturated bonds, and therefore the richness of the types of resins obtained is also remarkable. However, there are relatively few typ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
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 CHEM &MATERIAL CO LTD
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