IP Library Granted Patent US 11,919,995
Granted Patent B2
US 11,919,995 · App. 16/970,955 · Granted Mar 5, 2024

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

Inventors: Naoki Maruyama (Tokyo, JP); Tomoko Higashiuchi (Tokyo, JP); Kazumasa Fukuda (Tokyo, JP); Hideyuki Katagi (Tokyo, JP); Yuki Nakamura (Tokyo, JP); Yoshitaka Takezawa (Tokyo, JP)
Assignee: RESONAC CORPORATION
C08G59/245C08G59/5033C08K3/04
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Quick Facts
Patent No.
US 11,919,995
App. No.
16/970,955
Granted
Mar 5, 2024
Kind
B2
Abstract

An epoxy resin, comprising an epoxy compound having two or more mesogenic structures, and having a loss tangent of 1 or more at 35° C. before curing.

Claims (21)

1. An epoxy resin, comprising an epoxy compound having two or more mesogenic structures, and having a loss tangent of 1 or more at 35° C. before curing,

wherein the epoxy compound has a structure represented by the following Formula (1-B):

wherein, in Formula (1-B), each of R 1 and R 2 independently represents an alkyl group having 1 to 8 carbon atoms; X represents a single bond or a linking group that includes at least one divalent group selected from the following Group (A); each Y independently represents an aliphatic hydrocarbon group having 1 to 8 carbon atoms, an 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; each Z independently represents —O— or —NH—; each m independently represents an integer from 0 to 4; and each n independently represents an integer from 0 to 4:

wherein, in Group (A), each Y independently represents an aliphatic hydrocarbon group having 1 to 8 carbon atoms, an 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; k represents an integer from 0 to 7; l represents an integer from 0 to 12; m represents an integer from 0 to 8; and each n independently represents an integer from 0 to 4.

2. The epoxy resin according to claim 1 , wherein the epoxy compound has a structure represented by the following Formula (2-B);

3. The epoxy resin according to claim 1 , wherein at least one of the two or more mesogenic structures has a structure represented by at least one of Formula (3) or Formula (4):

wherein, in Formula (3) and Formula (4), each of R 3 to R 6 independently represents a hydrogen atom or an alkyl group having 1 to 3 carbon atoms.

4. The epoxy resin according to claim 1 , wherein the epoxy compound has two mesogenic structures and a divalent biphenyl group that is disposed between the two mesogenic structures.

5. The epoxy resin according to claim 1 , further comprising a mesogenic epoxy monomer represented by the following Formula (1-m):

wherein, in Formula (1-m), X represents a single bond or a linking group that includes at least one divalent group selected from the following Group (A); each Y independently represents an aliphatic hydrocarbon group having 1 to 8 carbon atoms, an 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:

wherein, in Group (A), each Y independently represents an aliphatic hydrocarbon group having 1 to 8 carbon atoms, an 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; k represents an integer from 0 to 7; l represents an integer from 0 to 12; m represents an integer from 0 to 8; and each n independently represents an integer from 0 to 4.

6. The epoxy resin according to claim 5 , wherein the mesogenic epoxy monomer comprises an epoxy compound represented by the following Formula (2-m):

7. The epoxy resin according to claim 5 , wherein the mesogenic epoxy monomer comprises an epoxy compound represented by the following Formula (3-m) or Formula (4-m):

wherein, in Formula (3-m) and Formula (4-m), each of R 3 to R 6 independently represents a hydrogen atom or an alkyl group having 1 to 3 carbon atoms.

8. The epoxy resin according to claim 5 , wherein a mass concentration, obtained by liquid chromatography, of the mesogenic epoxy monomer is not greater than 50% of the total mass concentration of the epoxy resin.

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

10. The epoxy resin composition according to claim 9 , wherein the curing agent comprises a compound having two or more amino groups that are directly bonded to an aromatic ring.

11. The epoxy resin composition according to claim 9 , wherein the curing agent comprises 3,3′-diaminodiphenylsulfone.

12. An epoxy resin cured product, which is obtained by curing the epoxy resin composition according to claim 9 .

13. A composite material, comprising the epoxy resin cured product according to claim 12 and a reinforcing material.

14. The composite material according to claim 13 , wherein the reinforcing material comprises a carbon material.

Assignments (5)
CHANGE OF ADDRESS Recorded Feb 9, 2024
From: RESONAC CORPORATION
To: RESONAC CORPORATION
Reel/Frame 066547/0677 →
CORRECTIVE ASSIGNMENT TO CORRECT THE ASSIGNEE'S ADDRESS PREVIOUSLY RECORDED AT REEL: 063042 FRAME: 0725. ASSIGNOR(S) HEREBY CONFIRMS THE CHANGE OF NAME. Recorded Apr 17, 2023
From: SHOWA DENKO MATERIALS CO., LTD.
To: RESONAC CORPORATION
Reel/Frame 063349/0537 →
CHANGE OF NAME Recorded Mar 21, 2023
From: SHOWA DENKO MATERIALS CO., LTD.
To: RESONAC CORPORATION
Reel/Frame 063042/0725 →
CHANGE OF NAME Recorded Mar 17, 2023
From: HITACHI CHEMICAL COMPANY, LTD.
To: SHOWA DENKO MATERIALS CO., LTD.
Reel/Frame 063015/0964 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Oct 6, 2020
From: MARUYAMA, NAOKI; HIGASHIUCHI, TOMOKO; FUKUDA, KAZUMASA; KATAGI, HIDEYUKI; NAKAMURA, YUKI; TAKEZAWA, YOSHITAKA
To: HITACHI CHEMICAL COMPANY, LTD.
Reel/Frame 053980/0020 →