IP Library Granted Patent US 11,466,119
Granted Patent B2
US 11,466,119 · App. 16/493,514 · Granted Oct 11, 2022

Epoxy resin, epoxy resin composition, epoxy resin cured product, and composite material

Inventors: Kazumasa Fukuda (Tokyo, JP); Yoshitaka Takezawa (Tokyo, JP); Naoki Maruyama (Tokyo, JP); Yuka Yoshida (Tokyo, JP); Tomoko Higashiuchi (Tokyo, JP)
Assignee: Showa Denko Materials Co., Ltd.
C08G59/504C08G59/226C08G59/24C08G59/245C08G59/5033
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Quick Facts
Patent No.
US 11,466,119
App. No.
16/493,514
Granted
Oct 11, 2022
Kind
B2
Abstract

An epoxy resin, comprising an epoxy compound having a mesogenic structure, the epoxy compound comprising a first epoxy compound having one biphenyl structure in a molecule and a second epoxy compound that is different from the first epoxy compound, at a mass ratio of the first epoxy compound to the second epoxy compound (first epoxy compound:second epoxy compound) of from 10:100 to 50:100.

Claims (20)

1. An epoxy resin, comprising an epoxy compound having a mesogenic structure,

the epoxy compound comprising a first epoxy compound having one biphenyl structure in a molecule and a second epoxy compound that is different from the first epoxy compound, at a mass ratio of the first epoxy compound to the second epoxy compound (first epoxy compound: second epoxy compound) of from 10:100 to 50:100,

wherein the second epoxy compound comprises an epoxy compound having one mesogenic structure and an epoxy compound having two or more mesogenic structures each represented by the following Formula (B):

wherein, in Formula (B), X represents a linking group comprising at least one divalent group having the following structure:

each Y independently represents an aliphatic hydrocarbon group having 1 to 8 carbon atoms, an aliphatic alkoxy group having 1 to 8 carbon atoms, a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, a cyano group, a nitro group or an acetyl group; and each n independently represents an integer from 0 to 4.

2. The epoxy resin according to claim 1 , wherein the first epoxy compound comprises an epoxy compound represented by the following Formula (A):

wherein, in Formula (A), each Z independently represents an aliphatic hydrocarbon group having 1 to 8 carbon atoms, an aliphatic alkoxy group having 1 to 8 carbon atoms, a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, a cyano group, a nitro group or an acetyl group; and each n independently represents an integer from 0 to 4.

3. The epoxy resin according to claim 1 , wherein the mass ratio of the first epoxy compound to the second epoxy compound (first epoxy compound: second epoxy compound) is from 10:100 to 25:100.

4. The epoxy resin according to claim 1 , having a viscosity at 60 ° C. of less than 200 Pa·s.

5. An epoxy resin composition, comprising the epoxy resin according to claim 1 and a curing agent.

6. The epoxy resin composition according to claim 5 , wherein the curing agent comprises an amine compound having a benzene ring or a naphthalene ring.

7. The epoxy resin composition according to claim 6 , wherein the amine compound has an amino group that is directly bonded to the benzene ring or the naphthalene ring.

8. The epoxy resin composition according to claim 5 , having a crosslink density of 7 mmol/cm 3 or less when the epoxy resin composition is cured.

9. The epoxy resin composition according to claim 5 , having a fracture toughness of 1.2 MPa·m 1/2 or more when the epoxy resin composition is cured.

10. A cured epoxy resin obtained by curing the epoxy resin composition according to claim 5 .

11. A composite material, comprising the cured epoxy resin according to claim 10 and a reinforcing material.

12. The composite material according to claim 11 , having a structure configured by layering at least a cured product-containing layer, comprising the cured epoxy resin, and at least one reinforcing material-containing layer, comprising the reinforcing material.

13. The epoxy resin according to claim 1 , wherein X of the epoxy compound represented by Formula (B) further comprises a divalent group having the following structure:

14. The epoxy resin according to claim 1 , wherein the epoxy compound represented by Formula (B) comprises one or more structures represented by the following formula (I):

wherein, in Formula (I), each of R 1 to R 4 independently represents a hydrogen atom or an alkyl group having from 1 to 3 carbon atoms.

Assignments (5)
CHANGE OF ADDRESS Recorded Feb 14, 2024
From: RESONAC CORPORATION
To: RESONAC CORPORATION
Reel/Frame 066599/0037 →
CORRECTIVE ASSIGNMENT TO CORRECT THE THE ADDRESS OF THE ASSIGNEE PREVIOUSLY RECORDED AT REEL: 06236 FRAME: 0323. ASSIGNOR(S) HEREBY CONFIRMS THE ASSIGNMENT. Recorded Mar 16, 2023
From: SHOWA DENKO MATERIALS CO., LTD.
To: RESONAC CORPORATION
Reel/Frame 063193/0416 →
CHANGE OF NAME Recorded Feb 9, 2023
From: SHOWA DENKO MATERIALS CO., LTD.
To: RESONAC CORPORATION
Reel/Frame 062636/0323 →
CHANGE OF NAME Recorded Aug 23, 2022
From: HITACHI CHEMICAL COMPANY, LTD.
To: SHOWA DENKO MATERIALS CO., LTD.
Reel/Frame 061302/0160 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Oct 23, 2019
From: FUKUDA, KAZUMASA; TAKEZAWA, YOSHITAKA; MARUYAMA, NAOKI; YOSHIDA, YUKA; HIGASHIUCHI, TOMOKO
To: HITACHI CHEMICAL COMPANY, LTD.
Reel/Frame 050799/0731 →