Heat-curable resin composition, prepreg, and fiber-reinforced composite material

Patent metadata

Field	Value
Publication number	US-11319435-B2
Application number	US-201916969650-A
Country	US
Kind code	B2
Filing date	Feb 6, 2019
Priority date	Feb 27, 2018
Publication date	May 3, 2022
Grant date	May 3, 2022

Abstract

A thermosetting resin composition at least including: [A] an epoxy resin containing two or more glycidyl groups; [B] a cyanate ester resin containing two or more cyanate groups; and [C] an amine compound; and satisfying the following conditions (1) and (2): (1) 0.25≤the number of moles of glycidyl groups in the thermosetting resin composition/the number of moles of cyanate groups in the thermosetting resin composition≤1.5; and (2) 0.05≤the number of moles of active hydrogen contained in the amino groups in the thermosetting resin composition/the number of moles of cyanate groups in the thermosetting resin composition<0.5; and a prepreg and a fiber reinforced composite material using the thermosetting resin composition. Provided are a thermosetting resin composition having excellent mechanical properties and heat resistance in a high-temperature environment after moisture absorption, and having excellent reactivity that allows curing in a short time; a prepreg prepared by impregnating a reinforced fiber with a thermosetting resin composition, which prepreg has excellent handling ability (tackiness properties) at room temperature; and a fiber reinforced composite material including a thermosetting resin composition and a reinforced fiber.

First claim

The invention claimed is:

1. A thermosetting resin composition comprising at least the following constituents [A] to [C]:
[A] an epoxy resin containing two or more glycidyl groups;
[B] a cyanate ester resin containing two or more cyanate groups; and
[C] an amine compound;

the thermosetting resin composition satisfying the following conditions (1) and (2):
(1) 0.25≤the number of moles of glycidyl groups in the thermosetting resin composition/the number of moles of cyanate groups in the thermosetting resin composition≤1.5; and
(2) 0.05≤the number of moles of active hydrogen contained in the amino groups in the thermosetting resin composition/the number of moles of cyanate groups in the thermosetting resin composition≤0.5;
wherein the thermosetting resin composition further comprises a thermoplastic resin; and
wherein the thermoplastic resin is dissolved in the constituent [A] and the constituent [B].

2. The thermosetting resin composition according to claim 1 , wherein the amine compound of the constituent [C] is an aromatic amine compound containing two or more amino groups.

3. The thermosetting resin composition according to claim 2 , wherein the amine compound of the constituent [C] contains diaminodiphenyl sulfone or diaminodiphenyl ketone.

4. The thermosetting resin composition according to claim 1 , wherein the amine compound of the constituent [C] is solid at 25° C.

5. The thermosetting resin composition according to claim 1 , wherein the epoxy resin containing two or more glycidyl groups of the constituent [A] contains 40 to 100 parts by mass of a glycidyl amine epoxy resin having at least a tri-functionality with respect to 100 parts by mass of total epoxy resin.

6. The thermosetting resin composition according to claim 1 , wherein the cyanate ester resin containing two or more cyanate groups of the constituent [B] contains 20 to 100 parts by mass of a cyanate ester resin represented by Formula (1):

(wherein in Formula (1), R 1 to R 4 are each selected from at least one selected from the group consisting of a hydrogen atom, an aliphatic hydrocarbon group having 1 to 4 carbon atoms, an alicyclic hydrocarbon group having 4 or less carbon atoms, and a halogen atom; and n represents 2 to 20)
with respect to 100 parts by mass of total cyanate ester resin.

7. The thermosetting resin composition according to claim 1 , wherein the amount of the thermoplastic resin contained in the thermosetting resin composition is 1 to 30% by mass.

8. The thermosetting resin composition according to claim 1 , wherein the thermoplastic resin is polyethersulfone.

9. The thermosetting resin composition according to claim 1 , having an exothermic reaction peak of not less than 100 mW/g at 160° C. to 200° C. in an exothermic curve according to differential scanning calorimetry at a temperature ramp rate of 5° C./minute.

10. The thermosetting resin composition according to claim 1 , having a storage elastic modulus of 0.1 to 100,000 Pa at 30° C. according to a dynamic viscoelasticity test at a frequency of 0.5 Hz.

11. A prepreg prepared by impregnating a reinforced fiber with the thermosetting resin composition according to claim 1 .

12. A fiber reinforced composite material prepared by curing of the prepreg according to claim 11 .

13. A fiber reinforced composite material comprising: a reinforced fiber; and a cured resin prepared by curing the thermosetting resin composition according to claim 1 .

Assignees

• Toray Industries

Inventors

• Misumi Jun
• Machida Ginpei
• Sakata Hiroaki

Classifications

• C08J5/243

  using carbon fibres · CPC title

• C08G59/56 Primary

  together with other curing agents · CPC title

• C08L79/00

  Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing nitrogen with or without oxygen or carbon only, not provided for in groups C08L61/00 - C08L77/00 · CPC title

• C08G59/4014

  Nitrogen containing compounds · CPC title

• C08L63/04

  Epoxynovolacs · CPC title