Epoxy resin curing agent, epoxy resin composition and cured product thereof, fiber-reinforced composite material, and high-pressure gas container

Patent metadata

Field	Value
Publication number	US-2025263519-A1
Application number	US-202318857545-A
Country	US
Kind code	A1
Filing date	Mar 2, 2023
Priority date	Apr 20, 2022
Publication date	Aug 21, 2025
Grant date	—

Abstract

Provided are an epoxy resin curing agent, an epoxy resin composition, a cured product thereof, a fiber-reinforced composite material, and a high-pressure gas container including the fiber-reinforced composite material, the epoxy resin curing agent including the following components (A-1) and (A-2):(A-1) a reaction composition containing polycondensation reaction product of aniline derivative and formaldehyde(A-2) a reaction composition containing a reaction product of styrene and a compound represented by the following General Formula (1):H2N—CH2-A-CH2—NH2  (1)(in Formula (1), A is a 1,2-phenylene group, a 1,3-phenylene group, or a 1,4-phenylene group).In the epoxy resin curing agent, a content of the component (A-1) is from 50 to 95 mass %, and a content of the component (A-2) is from 5 to 50 mass %.

First claim

1 . An epoxy resin curing agent, comprising
A following component (A-1) and a component (A-2): (A-1) a reaction composition comprising a polycondensation reaction product of an aniline derivative and formaldehyde; and (A-2) a reaction composition comprising a reaction product of styrene and a compound represented by the following General Formula (1):
H 2 N—CH 2 -A-CH 2 —NH 2   (1)

(in Formula (1), A is a 1,2-phenylene group, a 1,3-phenylene group, or a 1,4-phenylene group) wherein in the epoxy resin curing agent, a content of the component (A-1) is from 50 to 95 mass %, and a content of the component (A-2) is from 5 to 50 mass %.

2 . The epoxy resin curing agent according to claim 1 , wherein the aniline derivative is a compound represented by the following General Formula (2):

(in Formula (2), R 1 is an alkyl group having from 1 to 6 carbons or an aryl group, and p is a number from 1 to 3).

3 . The epoxy resin curing agent according to claim 1 , wherein in General Formula (1), A is a 1,3-phenylene group or a 1,4-phenylene group.

4 . The epoxy resin curing agent according to claim 1 , wherein the epoxy resin curing agent further comprises, as a component (A-3), a compound represented by the following General Formula (3):

(in Formula (3), R 2 is an alkyl group having from 1 to 6 carbons, an alkoxy group, or an alkylthio group, and q is a number from 0 to 3).

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

6 . The epoxy resin composition according to claim 5 , wherein the epoxy resin comprises: from 10 to 80 mass % of an epoxy resin (B1) including a glycidyl group derived from resorcinol; and from 20 to 90 mass % of an epoxy resin (B2), which is an epoxy resin other than (B1) with an aromatic ring,
wherein the epoxy resin (B2) comprises at least one selected from the group consisting of: an epoxy resin (b2-1) including a glycidyl group derived from bisphenol F; and an epoxy resin (b2-2) including a glycidyl group derived from phenol novolak.

7 . The epoxy resin composition according to claim 6 , wherein a total content of the epoxy resin (b2-1) and the epoxy resin (b2-2) in the epoxy resin (B2) is 50 mass % or more.

8 . The epoxy resin composition according to claim 5 , wherein a cured product of the epoxy resin composition has a hydrogen gas permeation coefficient of 1.0×10 −10 [cc·cm/(cm 2 ·sec·cmHg)] or less.

9 . A cured product of the epoxy resin composition according to claim 5 .

10 . A fiber-reinforced composite material, comprising: a cured product of the epoxy resin composition according to claim 5 ; and reinforcing fibers.

11 . The fiber-reinforced composite material according to claim 10 , wherein the reinforcing fibers are at least one selected from the group consisting of carbon fibers, glass fibers, and basalt fibers.

12 . The fiber-reinforced composite material according to claim 10 , wherein the fiber-reinforced composite material is obtained by filament winding molding.

13 . A high-pressure gas container, comprising the fiber-reinforced composite material according to claim 10 .

Assignees

• Mitsubishi Gas Chemical Co

Inventors

• Ikeuchi Kousuke
• Wakahara Daiki
• Ohnishi Nobuyoshi
• Okada Kana
• Matsumoto Nobuhiko

Classifications

• C08L2205/03

  containing three or more polymers in a blend · CPC title

• C08L2205/025

  containing two or more polymers of the same hierarchy C08L, and differing only in parameters such as density, comonomer content, molecular weight, structure · CPC title

• C08L63/04

  Epoxynovolacs · CPC title

• C08J2363/04

  Epoxynovolacs · CPC title

• C08J2363/02

  Polyglycidyl ethers of bis-phenols · CPC title