Resin composition, cured product thereof, fibre-reinforced plastic, and fibre-reinforced plastic flameproofing method

Patent metadata

Field	Value
Publication number	US-11905404-B2
Application number	US-201917254587-A
Country	US
Kind code	B2
Filing date	Jun 27, 2019
Priority date	Jul 4, 2018
Publication date	Feb 20, 2024
Grant date	Feb 20, 2024

Abstract

Provided is a resin composition that is capable of producing a cured product having excellent environmental suitability, high strength, and excellent flame retardancy, and that is suitably usable as a matrix resin for fiber-reinforced plastics. A resin composition contains (A) an epoxy resin, (B) a cyanate resin, (C) an aromatic amine curing agent that is liquid at 25° C., and (D) a phosphorus-containing compound represented by formula (1). Preferably, in formula (1), R 1 and R 2 each independently represent an alkyl group or an aryl group, and X and Y are an oxygen atom.

First claim

The invention claimed is:

1. A resin composition comprising:
(A) an epoxy resin;
(B) a cyanate resin;
(C) an aromatic amine curing agent that is liquid at 25° C.; and
(D) a phosphorus-containing compound represented by formula (1) below:

wherein, in formula (1),
m represents an integer from 1 to 10;
R 1 and R 2 each independently represent an alkyl group, an aryl group, or —NR 4 R 5 ;
R 4 and R 5 each independently represent a hydrogen atom, an alkyl group, or an aryl group;
in cases where R 1 and R 2 are both —NR 4 R 5 , each R 4 may be the same or different from one another, and R 5 s may be the same or different from one another;
R 3 represents a hydrocarbon group, wherein the hydrocarbon group may contain an atom selected from the group consisting of oxygen, sulfur, phosphorus, and nitrogen;
X represents an oxygen atom or a sulfur atom;
Y represents an oxygen atom, a sulfur atom, or —NR 6 —; and
R 6 represents a hydrogen atom, an alkyl group, or an aryl group, and
wherein a blending ratio of the phosphorus-containing compound represented by formula (1) with respect to 100 parts by mass of the epoxy resin is from 20 to 100 parts by mass.

2. The resin composition according to claim 1 , wherein R 1 and R 2 each independently represent an alkyl group or an aryl group, and X and Y are each an oxygen atom.

3. The resin composition according to claim 2 , wherein the hydrocarbon group represented by R 3 contains at least one aromatic ring.

4. The resin composition according to claim 2 , wherein m is 2, and R 3 is a group selected from the group consisting of formulas (2-1), (2-2), and (2-4) to (2-6) below:

wherein, in formula (2-1),
R 7 represents a hydrogen atom or an alkyl group having from 1 to 4 carbon atoms; and
* represents a bonding site;

wherein, in formula (2-2),
n represents an integer from 0 to 3;
o represents an integer from 0 to 50;
R 8 represents a hydrogen atom or an alkyl group having from 1 to 4 carbon atoms;
R 9 represents a hydrocarbon group, wherein the hydrocarbon group may contain an oxygen atom or a sulfur atom;
Z represents a hydroxyl group or a group represented by formula (2-3) below; and
* represents a bonding site;

wherein, in formula (2-3),
R 1′ and R 2′ each independently represent an alkyl group, an aryl group, or —NR 4′ R 5′ ;
R 4′ and R 5′ each independently represent a hydrogen atom, an alkyl group, or an aryl group;
in cases where R 1′ and R 2′ are both —NR 4′ R 5′ , each R 4′ may be the same or different from one another, and R 5′ may be the same or different from one another;
X′ represents an oxygen atom or a sulfur atom;
Y′ represents an oxygen atom, a sulfur atom, or —NR 6′ —;
R 6′ represents a hydrogen atom, an alkyl group, or an aryl group; and
* represents a bonding site;

wherein, in formula (2-4), * represents a bonding site;

wherein, in formula (2-5), * represents a bonding site;

wherein, in formula (2-6), * represents a bonding site.

5. The resin composition according to claim 2 , wherein the epoxy resin (A) contains from 20 to 80 mass % of a diglycidyl ether of bisphenol A-propylene oxide adduct.

6. The resin composition according to claim 2 , wherein the phosphorus-containing compound (D) represented by formula (1) is contained in an amount that makes the content of phosphorus originating from the phosphorus-containing compound from 0.1 to 5 mass % with respect to a total solid content of the epoxy resin (A), the cyanate resin (B), the aromatic amine curing agent (C) that is liquid at 25° C., and the phosphorus-containing compound (D) represented by formula (1).

7. The resin composition according to claim 1 , wherein the hydrocarbon group represented by R 3 contains at least one aromatic ring.

8. The resin composition according to claim 7 , wherein m is 2, and R 3 is a group selected from the group consisting of formulas (2-1), (2-2), and (2-4) to (2-6) below:

wherein, in formula (2-1),
R 7 represents a hydrogen atom or an alkyl group having from 1 to 4 carbon atoms; and
* represents a bonding site;

wherein, in formula (2-2),
n represents an integer from 0 to 3;
o represents an integer from 0 to 50;
R 8 represents a hydrogen atom or an alkyl group having from 1 to 4 carbon atoms;
R 9 represents a hydrocarbon group, wherein the hydrocarbon group may contain an oxygen atom or a sulfur atom;
Z represents a hydroxyl group or a group represented by formula (2-3) below; and
* represents a bonding site;

wherein, in formula (2-3),
R 1′ and R 2′ each independently represent an alkyl group, an aryl group, or —NR 4′ R 5′ ;
R 4′ and R 5′ each independently represent a hydrogen atom, an alkyl group, or an aryl group;
in cases where R 1′ and R 2′ are both —NR 4′ R 5′ , each R 4′ may be the same or different from one another, and R 5′ may be the same or different from one another;
X′ represents an oxygen atom or a sulfur atom;
Y′ represents an oxygen atom, a sulfur atom, or —NR 6′ —;
R 6′ represents a hydrogen atom, an alkyl group, or an aryl group; and
* represents a bonding site;

wherein, in formula (2-4), * represents a bonding site;

wherein, in formula (2-5), * represents a bonding site;

wherein, in formula (2-6), * represents a bonding site.

9. The resin composition according to claim 7 , wherein the epoxy resin (A) contains from 20 to 80 mass % of a diglycidyl ether of bisphenol A-propylene oxide adduct.

10. The resin composition according to claim 7 , wherein the phosphorus-containing compound (D) represented by formula (1) is contained in an amount that makes the content of phosphorus originating from the phosphorus-containing compound from 0.1 to 5 mass % with respect to a total solid content of the epoxy resin (A), the cyanate resin (B), the aromatic amine curing agent (C) that is liquid at 25° C., and the phosphorus-containing compound (D) represented by formula (1).

11. The resin composition according to c

Assignees

• Adeka Corp

Inventors

• INADOME Masato
• Fujita Naohiro
• Morino Kazuhide
• Asakura Chihiro

Classifications

• C08J2363/00

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

• C08L2201/02

  Flame or fire retardant/resistant · CPC title

• C08J5/10

  characterised by the additives used in the polymer mixture · CPC title

• C08G59/4028 Primary

  Isocyanates; Thioisocyanates · CPC title

• C08J5/249

  characterised by the additives used in the prepolymer mixture · CPC title