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Alicyclic acrylate compound, alicyclic epoxy acrylate compound, curable composition, and cured product

A technology of epoxy acrylate and curable composition, applied in the direction of organic chemistry etc.

Pending Publication Date: 2022-07-12
JXTJ NIPPON OIL & ENERGY CORP
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0007] However, conventional epoxy group-containing (meth)acrylic compounds such as those proposed in Patent Documents 1 and 2 have room for further improvement from the viewpoint of heat resistance of cured products and the like.

Method used

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  • Alicyclic acrylate compound, alicyclic epoxy acrylate compound, curable composition, and cured product
  • Alicyclic acrylate compound, alicyclic epoxy acrylate compound, curable composition, and cured product
  • Alicyclic acrylate compound, alicyclic epoxy acrylate compound, curable composition, and cured product

Examples

Experimental program
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Embodiment

[0361] Hereinafter, the present invention will be specifically described with reference to Examples and Comparative Examples, but the present invention is not limited to these Examples and Comparative Examples.

[0362]

[0363] As the component (A), the following alicyclic epoxy acrylate type polymerizable monomer (A1) was synthesized and used. (Hereinafter, the alicyclic epoxy acrylate type polymerizable monomer (A1) is also abbreviated as epoxy acrylate compound (A1))

preparation example 1

[0364] Preparation Example 1: Alicyclic epoxy acrylate type polymerizable monomer (A1) (tricyclopentadiene-epoxy methacrylic acid) Synthesis of Ester: TCPD-EM)

preparation example 1－1

[0365] Preparation Example 1-1: Alicyclic acrylate type polymerizable monomer (tricyclopentadiene-methacrylate: TCPD- Synthesis of M)

[0366] 120 g of the diene compound represented by the formula (1-a-1), 1.2 L of isopropyl ether, 1.96 g of iron(III) chloride, and 56.2 ml of methacrylic acid were put into a reaction vessel equipped with a thermometer, a stirring bar, and a reflux tube. . Then, 3.2 ml of trifluoromethanesulfonic acid was slowly added at room temperature, and the mixture in the reaction vessel was continuously stirred under reflux conditions for 25 hours. Then, it stood to cool to room temperature, and after washing|cleaning with 1 L of saturated sodium bicarbonate aqueous solution, the obtained aqueous layer was extracted twice with 1 L of isopropyl ether. The obtained organic layers were mixed, purified by a silica gel column (silica gel 60 (spherical) (manufactured by Kanto Chemical Co., Ltd.)), and then concentrated by an evaporator to obtain 170 g of...

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Abstract

The invention provides an alicyclic epoxy acrylate compound, a curable composition and a cured product. When the alicyclic epoxy acrylate compound is contained in the curable composition, the cured product can have high heat resistance. An alicyclic epoxy acrylate compound represented by formula (1) in which A is oxygen, and a curable composition containing the alicyclic epoxy acrylate compound are used [in the formula, either one of R1 and R2 is a (meth) acryloyloxy group, the other of R1 and R2 is a hydrogen atom, R3 to R20 are each independently selected from the group consisting of a hydrogen atom, an alkyl group, and an alkoxy group, A is an oxygen atom, R2 is a hydrogen atom, and R3 to R20 are each independently selected from the group consisting of a hydrogen atom, an alkyl group, and an alkoxy group. Or there is no A and the carbon atom to which R8 is bonded forms a double bond together with the carbon atom to which R9 is bonded].

Description

[0001] CROSS-REFERENCE TO RELATED APPLICATIONS [0002] This patent application claims priority based on Japanese Patent Application No. 2019-218298 for which it applied on December 2, 2019, and the entire disclosure of the prior patent application is made a part of this specification by reference. technical field [0003] The present invention relates to an alicyclic acrylate compound, an alicyclic epoxy acrylate compound, a curable composition and a cured product. Background technique [0004] Epoxy group-containing (meth)acrylic compounds and acrylates having an alicyclic skeleton are generally useful compounds in the fields of resists, sealing materials, coatings, inks, adhesives, and sealants. Here, it is known that the acrylate containing an alicyclic skeleton and an epoxy group has characteristics suitable for outdoor use. These generally exhibit predetermined performance by a ring-opening reaction of an ethylene oxide ring existing in a structure, a reaction of an e...

Claims

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Application Information

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IPC IPC(8): C07C69/54C08F20/00C08G59/20C08G65/14C07D303/44
CPCC07C69/54C08F2/50C07D303/17C07C2603/91C08G59/42C08F220/32C08F265/06C08G59/3209C08F220/14C07D303/44C08F220/18C08F222/1067C08F220/06C08K5/09
Inventor 上健太小池刚龟山敦史
Owner JXTJ NIPPON OIL & ENERGY CORP
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