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Polyfunctional (meth)acrylic acid ester copolymer, and curable resin composition and cured product thereof

An acrylate, multifunctional technology, applied in the field of curable resin compositions and their cured products, can solve the problems of reduced adhesion of inorganic materials, reduced strength and heat resistance of resin compositions, etc., and achieves improved adhesion, Excellent balance of properties, high light transmittance effect

Active Publication Date: 2015-11-25
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 these disclosed technologies, there is a disadvantage that since no difunctional or higher-functional vinyl compound having a plurality of vinyl groups is added during polymerization, only one or less molecular weight-derived compounds can be introduced into the polymer chain. The end group of the agent cannot fully perform the function imparted by the end group
Furthermore, there is also the disadvantage that the self-curing copolymer obtained by this technique forms a thermosetting resin composition in a resin composition with an epoxy resin, but does not cause a curing reaction with an acrylate resin, thus causing complexation. Decrease in the strength and heat resistance of the resin composition
However, in the technique disclosed here, there is a disadvantage that the adhesion to inorganic materials is lowered in long-term reliability tests under high temperature and high humidity conditions.

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0110] NDDA252.35g, DCPA309.42g, EHDGA544.76g, HOP65.07g, αMSD222.32g, and toluene 700ml were put into a 3.0L reactor, and 65.60mmol of benzoyl peroxide was added at 85°C and allowed to react for 2 hours. After the polymerization reaction was stopped by cooling, the reaction mixture was poured into a large amount of methanol at room temperature to precipitate a polymer. The obtained polymer was washed with methanol, filtered, dried, and weighed to obtain 31.1 g of copolymer A (yield: 31 wt %).

[0111] Mw of the obtained copolymer A was 117,234, Mn was 20,874, and Mw / Mn was 5.6. by carrying out 13 C-NMR, 1 H-NMR analysis and elemental analysis, copolymer A contains a total of 11.8 mol% of structural units derived from NDDA, a total of 30.1 mol% of structural units derived from DCPA, 49.7 mol% of structural units derived from EHDGA, and a structural unit derived from HOP 9.4 mol%. In addition, the terminal group derived from the structure of αMSD was present at 2.7 mol%. I...

Embodiment 2、3 and comparative example 1、2

[0114] 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.

[0115] 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 description is set as mol / g.

[0116] [Table 1]

[0117] Consumption mol / g

Example 1

Example 2

Example 3

Comparative example 1

Comparative example 2

DMTCD

0.75 / 228.3

1.6 / 487.0

1.8 / 547.9

NDDA

1.0 / 252.4

0.75 / 189.3

0.3 / 75.7

BDDA

0.3 / 59.5

1.2 / 237.9

0.3 / 59.5

HOP

0.5 / 65.1

0.3 / 3...

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PUM

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Abstract

Provided are: a polyfunctional (meth)acrylic acid ester copolymer which has excellent optical properties, does not undergo the deterioration in adhesion to inorganic materials even when the copolymer is exposed to moisturized and heated conditions for a long time of period, and can keep the optical properties thereof at high levels; and a curable resin composition containing the polyfunctional (meth)acrylic acid ester copolymer. A polyfunctional (meth)acrylic acid ester copolymer which is a copolymer produced by copolymerizing monomers comprising (a) a monofunctional (meth)acrylic acid ester generated from (meth)acrylic acid and an alcohol having 9 to 30 carbon atoms, (b) a bifunctional (meth)acrylic acid ester represented by the formula: CH2=CR-CO-O-R2-O-OC-CR=CH2 and (c) 2,4-diphenyl-4-methyl-1-pentene, said copolymer having a reactive (meth)acrylate group derived from the component (b) in a side chain thereof, also having a structural unit derived from the component (c) at the terminal thereof, and being soluble in a solvent such as toluene.

Description

technical field [0001] The present invention relates to optical properties such as optical isotropy and high light transmittance, heat resistance, and processability, and heat resistance and adhesion to inorganic materials under severe actual use conditions such as hot and humid conditions. Curable resin composition with improved compatibility and cured product thereof. Background technique [0002] Many monomers with reactive unsaturated bonds can form multimers by selecting catalysts that cause chain reactions due to unsaturated bond breakage and appropriate reaction conditions. Generally, the types of monomers having unsaturated bonds are extremely diverse, and therefore, the variety of resins obtained is also remarkable. However, there are few types of monomers that can give a high-molecular-weight body having a molecular weight of 10,000 or more, which is generally called a high-molecular compound. Examples include ethylene, substituted ethylene, propylene, substitute...

Claims

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Application Information

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IPC IPC(8): C08F220/10G02B1/04
CPCC08F220/28C08F220/282C08F220/281C08F220/1811C08F222/102C08F212/32C08F220/20
Inventor 林健太郎河谷俊宏川边正直
Owner NIPPON STEEL CHEMICALL &MATERIAL CO LTD
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