Thermosetting resin composition, prepreg, and fiber-reinforced composite material and production method therefor

Patent metadata

Field	Value
Publication number	US-11618803-B2
Application number	US-202117202419-A
Country	US
Kind code	B2
Filing date	Mar 16, 2021
Priority date	Nov 16, 2017
Publication date	Apr 4, 2023
Grant date	Apr 4, 2023

Abstract

Provided is a thermosetting resin composition which achieves both high heat resistance and high bending strength as a fiber-reinforced composite material, and also has rapid curability that enables high cycle press forming, thermal stability, and storage stability. The thermosetting resin composition of the present invention is a thermosetting resin composition comprising an epoxy resin, an epoxy resin curing agent, an imidazole compound, and an epoxy resin curing accelerator, in which the epoxy resin curing agent is dicyandiamide or a derivative thereof, and the epoxy resin curing accelerator comprises a urea derivative having two or more dimethylureido groups in a molecule.

First claim

The invention claimed is:

1. A thermosetting resin composition comprising:
an epoxy resin;
an epoxy resin curing agent;
an imidazole compound; and
an epoxy resin curing accelerator,
wherein the epoxy resin curing agent comprises dicyandiamide or a derivative thereof,
the epoxy resin curing accelerator comprises a urea derivative having two or more dimethylureido groups in a molecule,
the thermosetting resin composition comprises 1 to 9 parts by mass of the dicyandiamide or a derivative thereof, 1 to 8 parts by mass of the imidazole compound, and 1 to 8 parts by mass of the urea derivative having two or more dimethylureido groups in a molecule, each with respect to 100 parts by mass of the epoxy resin, and
the epoxy resin comprises 30 to 70 parts by mass of a first epoxy resin having a structure represented by Formula (1) in a molecule, and 20 to 40 parts by mass of a second epoxy resin, each relative to 100 parts by mass of the epoxy resin,

wherein the second epoxy resin is a polyfunctional epoxy resin having three or more epoxy groups in a molecule, and the polyfunctional epoxy resin does not contain the structure represented by Formula (1).

2. The thermosetting resin composition according to claim 1 , wherein a curing completion time is 6 minutes or shorter at 140° C.

3. The thermosetting resin composition according to claim 1 , wherein, when a viscosity after holding at 60° C. for 5 minutes is V0 and a viscosity after holding at 60° C. for 5 hours is V1, V1/V0 is 1.0 to 4.5.

4. The thermosetting resin composition according to claim 1 , wherein the imidazole compound comprises an imidazole compound having a curing start temperature of 100° C. or higher.

5. The thermosetting resin composition according to claim 1 , wherein the imidazole compound comprises at least one selected from the group consisting of an imidazole derivative, an imidazole adduct, an inclusion compound of imidazole, a microencapsulated imidazole, and an addition product comprising imidazole.

6. The thermosetting resin composition according to claim 1 , wherein the urea derivative having two or more dimethylureido groups in a molecule comprises one or both of 2,4-bis(3,3-dimethylureido)toluene and 4,4′-methylene bis(phenyldimethylurea).

7. The thermosetting resin composition according to claim 1 , wherein the polyfunctional epoxy resin having three or more epoxy groups in a molecule comprises at least one selected from the group consisting of a phenol novolac type epoxy resin, a trisphenolmethane type epoxy resin, and a tetraglycidyl diaminodiphenylmethane.

8. A prepreg comprising:
the thermosetting resin composition according to claim 1 ; and
a reinforcing fiber base material.

9. The prepreg according to claim 8 , wherein a cured product obtained by holding the prepreg at 140° C. for 5 minutes while applying a pressure thereto has a glass transition temperature of 150° C. or higher.

10. A fiber-reinforced composite which is a cured product of the prepreg according to claim 8 .

11. The fiber-reinforced composite according to claim 10 , which has a glass transition temperature of 150° C. or higher.

12. A method of producing a fiber-reinforced composite, the method comprising:
curing a prepreg according to claim 8 to produce the fiber-reinforced composite.

13. The method according to claim 12 , wherein the fiber-reinforced composite has a glass transition temperature of 150° C. or higher.

14. A method of producing a fiber-reinforced composite, the method comprising:
subjecting the prepreg according to claim 8 to heating and pressurization forming.

15. The method according to claim 14 , the method further comprising:
shaping the prepreg according to claim 8 , prior to the heating and pressurizing forming, to produce a preform having a near net shape of the fiber reinforced composite which is to be produced by the heating and pressurizing forming.

16. The method according to claim 14 , wherein the fiber-reinforced composite has a glass transition temperature of 150° C. or higher.

Assignees

• Mitsubishi Chem Corp

Inventors

• Teranishi Takuya
• Ichino Masahiro
• Oota Akira

Classifications

• C08G59/3263

  containing sulfur · CPC title

• C08L63/00

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

• C08K5/21

  Urea; Derivatives thereof, e.g. biuret · CPC title

• C08K5/3445

  Five-membered rings · CPC title

• C08G59/4021 Primary

  Ureas; Thioureas; Guanidines; Dicyandiamides · CPC title