Epoxy resin composition, curable resin composition, and fiber-reinforced composite material

Patent metadata

Field	Value
Publication number	US-11286385-B2
Application number	US-201816765000-A
Country	US
Kind code	B2
Filing date	Nov 8, 2018
Priority date	Nov 22, 2017
Publication date	Mar 29, 2022
Grant date	Mar 29, 2022

Abstract

The present invention provides an epoxy resin composition that contains an epoxy resin (A) that is a product of reaction between an epihalohydrin and either catechol, optionally with its aromatic ring methyl-substituted, or pyrogallol, optionally with its aromatic ring methyl-substituted, and an aromatic glycidylamine epoxy resin (B). This epoxy resin composition is suitable for use in fiber-reinforced composite materials, fiber-reinforced plastic articles, etc., by virtue of being liquid at room temperature, being superior in quick curing, and high mechanical properties in its cured form.

First claim

The invention claimed is:

1. An epoxy resin composition comprising an epoxy resin (A) that is a product of reaction between an epihalohydrin and either catechol, optionally with an aromatic ring thereof methyl-substituted, or pyrogallol, optionally with an aromatic ring thereof methyl-substituted, and an aromatic glycidylamine epoxy resin (B);
wherein the epoxy resin (A) contains a cyclic compound (a1) that has a cyclic structure whose constituent atoms include two oxygen atoms derived from oxygen atoms of either the catechol optionally with an aromatic ring thereof methyl-substituted or pyrogallol optionally with an aromatic ring thereof methyl-substituted; and
wherein a cyclic compound (a1) content is between 0.040 and 0.115 mol per 100 g of the epoxy resin (A) of the catechol optionally with an aromatic ring thereof methyl-substituted or the pyrogallol optionally with an aromatic ring thereof methyl-substituted.

2. The epoxy resin composition according to claim 1 , wherein an amount of a derived glycidyl ether (a2), represented by structural formula (1) or (2) below

wherein, in formulae (1) and (2), G is a glycidyl group, each R 1 is independently a hydrogen atom or methyl group, m is an integer of 1 to 4, and n is an integer of 1 to 3,
in the epoxy resin (A) is 55% or more when expressed as a percentage area in GPC.

3. The epoxy resin composition according to claim 1 , wherein the epoxy resin (A) further contains oligomers (a3), and an oligomer (a3) content is 12% or less when expressed as a percentage area in GPC.

4. The epoxy resin composition according to claim 1 , wherein the epoxy resin (A) is a product of reaction between an epihalohydrin and pyrogallol, and an epoxy equivalent weight thereof is between 108 and 170 g/eq.

5. The epoxy resin composition according to claim 1 , wherein the aromatic glycidylamine epoxy resin (B) is 4,4′-methylenebis(N,N-diglycidylaniline).

6. The epoxy resin composition according to claim 1 , wherein a blend ratio between the epoxy resin (A) that is a product of reaction between an epihalohydrin and either catechol, optionally with an aromatic ring thereof methyl-substituted, or pyrogallol, optionally with an aromatic ring thereof methyl-substituted, and the aromatic glycidylamine epoxy resin (B) is between 10/90 and 90/10 when expressed as a ratio by mass represented by (A)/(B).

7. A curable resin composition comprising an epoxy resin composition according to claim 1 and a curing agent (C).

8. The curable resin composition according to claim 7 , wherein the curing agent (C) is diaminodiphenylsulfone.

9. A cured form of a curable resin composition according to claim 7 .

10. A fiber-reinforced plastic article comprising a cured form according to claim 9 and reinforcing fiber as essential components.

11. The fiber-reinforced plastic article according to claim 10 , wherein a percentage by volume of the reinforcing fiber is between 40% and 85%.

12. A fiber-reinforced composite material comprising a curable resin composition according to claim 7 and reinforcing fiber as essential components.

13. The fiber-reinforced composite material according to claim 12 , wherein a percentage by volume of the reinforcing fiber is between 40% and 85%.

14. A method for producing a fiber-reinforced plastic article comprising thermally curing a fiber-reinforced composite material according to claim 12 .

Assignees

• Dainippon Ink & Chemicals

Inventors

• Hayashi Koji
• Sugimoto Nana
• Morinaga Kunihiro

Classifications

• C08J2363/00

  Characterised by the use of epoxy resins; Derivatives of epoxy resins · CPC title

• C08J5/04 Primary

  Reinforcing macromolecular compounds with loose or coherent fibrous material · CPC title

• C08G59/06

  of polyhydric phenols · CPC title

• C08G59/10

  of polyamines with epihalohydrins or precursors thereof · CPC title

• C08L63/00 Primary

  Compositions of epoxy resins; Compositions of derivatives of epoxy resins · CPC title