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

Patent metadata

Field	Value
Publication number	US-12116451-B2
Application number	US-201917598305-A
Country	US
Kind code	B2
Filing date	Mar 27, 2019
Priority date	Mar 27, 2019
Publication date	Oct 15, 2024
Grant date	Oct 15, 2024

Abstract

An epoxy resin includes a reaction product between: an epoxy compound having a mesogenic structure; and at least one selected from the group consisting of an aromatic hydroxycarboxylic acid having a carboxy group and a hydroxy group bonded to an aromatic ring and an aromatic dicarboxylic acid having two carboxy groups bonded to an aromatic group.

First claim

The invention claimed is:

1. An epoxy resin, comprising at least one compound selected from the group consisting of the following General Formulae (E1) and (E2):

wherein, in General Formulae (E1) and (E2), Ar represents a substituted or unsubstituted aromatic ring; each of R1 and R2 independently represents a monovalent organic group having a glycidyl group, wherein at least one selected from the group consisting of R 1 and R2 includes a mesogenic structure; and each R3 independently represents a hydrogen atom or a monovalent organic group, at least one R3 being a monovalent organic group of the following Formula (c):

wherein, in Formula (c), R 4 represents a monovalent organic group; and * represents a bonding site to an oxygen atom.

2. The epoxy resin according to claim 1 , wherein, in General Formulae (E1) and (E2), Ar represents a substituted or unsubstituted benzene ring or naphthalene ring.

3. The epoxy resin according to claim 1 , wherein the mesogenic structure comprises a structure represented by the following General Formula (M):

wherein, in General Formula (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; each n independently represents an integer from 0 to 4; and * represents a bonding site to an adjacent atom:

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; each n independently represents an integer from 0 to 4;
k represents an integer from 0 to 7; m represents an integer from 0 to 8; and 1 represents an integer from 0 to 12.

4. The epoxy resin according to claim 1 , wherein the mesogenic structure comprises a structure represented by the following General Formula (M-2):

wherein, in General Formula (M-2), 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 n independently represents an integer from 0 to 4; and * represents a bonding site to an adjacent atom.

5. The epoxy resin according to claim 1 , having an epoxy equivalent weight of from 300 to 380 g/eq.

6. The epoxy resin according to claim 1 , having a melt viscosity at 100° C. of 2.0 to 50.0 Pa·s.

7. The epoxy resin according to claim 1 , wherein a cured product of the epoxy resin cured by 3,3′-diaminodiphenyl sulfone, which is a curing agent, has a fracture toughness of 2.4 MPa·m 1/2 or more measured by three-point bend testing in accordance with ASTM D5045-14.

8. The epoxy resin according to claim 1 , wherein a cured product of the epoxy resin cured by 3,3′-diaminodiphenyl sulfone, which is a curing agent, shows an interference pattern due to depolarization, when the cured product is observed with a polarized light microscope under crossed Nicols.

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

10. An epoxy resin cured product, which is a cured product of the epoxy resin composition according to claim 9 .

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

Assignees

• Showa Denko Materials Co Ltd
• Resonac Corp

Inventors

• Katagi Hideyuki
• Nakamura Yuki
• Fukuda Kazumasa
• Ikeda Tomohiro
• Tian Lin
• Tougasaki Kei
• Maruyama Naoki
• Takezawa Yoshitaka

Classifications

• C08G59/688

  containing phosphorus · CPC title

• C08G59/5033

  aromatic · CPC title

• C08G59/4064

  sulfur containing compounds (C08G59/4021, C08G59/4028 take precedence) · CPC title

• C08G59/245

  aromatic · CPC title

• C08G59/623

  Aminophenols · CPC title