# US 10,767,001 B2 · Epoxy resin curing agent, epoxy resin composition, and carbon fiber-reinforced composite material

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- Number: US 10,767,001 B2
- Document ID: US10767001B2
- Status: Granted
- Kind: B2
- Application number: 16/090,884
- Filed: 2017-03-15
- Published: 2019-04-25
- Granted: 2020-09-08
- Earliest claimed: 2016-04-12
- Assignees: Mitsubishi Gas Chemical Company, Inc.
- Applicants: Mitsubishi Gas Chemical Company, Inc.
- Inventors: Yuiga Asai; Tomotaka Wada
- Web page: https://patentgrep.com/patent/US10767001B2

## CPC

- C08G 59/56: together with other curing agents
- B29C 39/18: incorporating preformed parts or layers, e.g. casting around inserts or for coating articles {(B29C39/206 takes precedence)}
- B29C 70/28: Shaping operations therefor
- C08G 59/245: {aromatic}
- C08G 59/5026: {cycloaliphatic}
- C08G 59/5033: {aromatic}
- C08G 59/5073: {having two nitrogen atoms in the ring}
- C08G 59/621: {Phenols}
- C08J 5/005: {Reinforced macromolecular compounds with nanosized materials, e.g. nanoparticles, nanofibres, nanotubes, nanowires, nanorods or nanolayered materials}
- C08J 5/042: {with carbon fibres}
- C08J 5/243: {using carbon fibres}
- C08J 5/249: {characterised by the additives used in the prepolymer mixture}
- C08K 7/06: Elements
- B29K 2063/00: Use of {EP, i.e.} epoxy resins {or derivatives thereof}, as moulding material
- B29K 2105/0005: {containing compounding ingredients (releasing, lubricating or separating agents B29C33/56, fibers B29K2105/08, B29K2105/12; fillers B29K2105/16, recycled material B29K2105/26)}
- B29K 2307/04: Carbon
- B29L 2031/30: Vehicles, e.g. ships or aircraft, or body parts thereof {(vanes or blades B29L2031/08, air bags B29L2022/027)}
- C08J 2363/02: Polyglycidyl ethers of bis-phenols
- C08G: MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- B29C: SHAPING OR JOINING OF PLASTICS; SHAPING OF MATERIAL IN A PLASTIC STATE, NOT OTHERWISE PROVIDED FOR; AFTER-TREATMENT OF THE SHAPED PRODUCTS, e.g. REPAIRING (making preforms B29B11/00; making laminated products by combining previously unconnected layers which become one product whose layers will remain together B32B37/00 - B32B41/00)
- C08J: WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H (working, e.g. shaping, of plastics B29)
- C08K: Use of inorganic or non-macromolecular organic substances as compounding ingredients (paints, inks, varnishes, dyes, polishes, adhesives C09)
- B29K: INDEXING SCHEME ASSOCIATED WITH SUBCLASSES B29B, B29C OR B29D, RELATING TO MOULDING MATERIALS OR TO MATERIALS FOR {MOULDS, } REINFORCEMENTS, FILLERS OR PREFORMED PARTS, e.g. INSERTS
- B29L: INDEXING SCHEME ASSOCIATED WITH SUBCLASS B29C, RELATING TO PARTICULAR ARTICLES

## Abstract

Provided are: an epoxy resin curing agent containing an amine compound (A) represented by the following general formula (1) and a phenol compound (B), wherein the content of the component (B) is 8 to 35 parts by mass relative to 100 parts by mass of the component (A), an epoxy resin composition containing it, and a carbon fiber-reinforced composite material containing a cured product of the epoxy resin composition and carbon fibers. R1HN—H2C-A-CH2—NHR2 (1) wherein R1 and R2 each independently represent a hydrogen atom, or an aminoalkyl group having 1 to 6 carbon atoms, and A represents a cyclohexylene group or a phenylene group.

## Claims

### Claim 1

An epoxy resin curing agent comprising an amine compound (A) represented by the following formula (1) and a phenol compound (B), wherein the content of the component (B) is from 8 to 35 parts by mass relative to 100 parts by mass of the component (A):
R1HN—H2C-A-CH2—NHR2 (1)
wherein R1 and R2 each independently represents a hydrogen atom or an aminoalkyl group having 1 to 6 carbon atoms, and A represents a cyclohexylene group or a phenylene group,
wherein the total content of the amine compound (A) and the phenol compound (B) is from 80% by mass to 100% by mass, relative to the total amount of the epoxy resin curing agent.

### Claim 2 (depends on 1)

The epoxy resin curing agent according to claim 1, wherein R1 and R2 in the formula (1) are both hydrogen atoms.

### Claim 3 (depends on 1)

The epoxy resin curing agent according to claim 1, wherein A in the formula (1) is a cyclohexylene group.

### Claim 4 (depends on 1)

The epoxy resin curing agent according to claim 1, wherein the phenol compound (B) is a compound represented by the following formula (2):
wherein R5 and R6 each independently represents an OH group or an alkyl group having 1 to 4 carbon atoms; j and k each independently represents an integer of 0 to 5, provided that j+k is 1 or more; plural R5's, if any, may be all the same as or different from each other, plural R6's, if any, may be all the same as or different from each other, provided that at least one OH group is present as R5 or R6; and Z represents a single bond, an alkylene group having 1 to 6 carbon atoms, an alkylidene group having 2 to 6 carbon atoms, a cycloalkylene group having 5 to 10 carbon atoms, a cycloalkylidene group having 5 to 10 carbon atoms, an arylalkylene group having 7 to 15 carbon atoms, an arylalkylidene group having 7 to 15 carbon atoms, —S—, —SO—, —SO2—, —O—, —CO—, —C(CF3)2—, —CH(CF3)—, —CF2—, —CONH—, or —COO—.

### Claim 5 (depends on 4)

The epoxy resin curing agent according to claim 4, wherein the phenol compound (B) is at least one selected from the group consisting of 4,4′-(propane-2,2-diyl)diphenol, bis(4-hydroxyphenyl)methane, 1,1-bis(4-hydroxyphenyl)ethane, and styrenated phenol.

### Claim 6 (depends on 1)

An epoxy resin composition comprising the epoxy resin curing agent of claim 1, and an epoxy resin.

### Claim 7 (depends on 6)

The epoxy resin composition according to claim 6, wherein the epoxy resin is an epoxy resin containing an aromatic ring or an alicyclic structure in the molecule.

### Claim 8 (depends on 7)

The epoxy resin composition according to claim 7, wherein the epoxy resin is an epoxy resin represented by the following formula (3):
wherein R21 to R24 each independently represents an alkyl group having 1 to 6 carbon atoms; p, q, r and s each independently represents an integer of 0 to 4, with respect to each of R21, R22, R23, and R24, plural groups, if any, may be all the same as or different from each other; Y1 and Y2 each independently represents a single bond, —CH2—, —CH(CH3)—, or —C(CH3)2—; R25 represents —CH2CH(OH)—, or —CH(OH)CH2—; and m represents a mean repeating unit number and is a number of 0 to 0.2.

### Claim 9 (depends on 6)

The epoxy resin composition according to claim 6, which has a viscosity at a temperature 40° C. of 400 mPa·s or less.

### Claim 10 (depends on 6)

The epoxy resin composition according to claim 6, which is for a carbon fiber-reinforced composite material.

### Claim 11 (depends on 6)

A carbon fiber-reinforced composite material comprising a cured product of the epoxy resin composition of claim 6, and carbon fibers.

### Claim 12 (depends on 11)

The carbon fiber-reinforced composite material according to claim 11, which is a structure material for an automobile.

### Claim 13 (depends on 11)

A method for producing the carbon fiber-reinforced composite material of claim 11, comprising performing molding according to a low-pressure RTM method, a middle-pressure RTM method, a high-pressure RTM method, a compression RTM method, a liquid compression molding method, a liquid lay-down molding method, a spray lay-down molding method, a surface RTM method, a prepreg compression molding method, or a liquid cast molding method.

### Claim 14

An epoxy resin curing agent comprising an amine compound (A) represented by the following formula (1) and a phenol compound (B), wherein the content of the component (B) is from 8 to 35 parts by mass relative to 100 parts by mass of the component (A):
R1HN—H2C-A-CH2—NHR2 (1)
wherein R1 and R2 each independently represent a hydrogen atom, or an aminoalkyl group having 1 to 6 carbon atoms, and A represents a cyclohexylene group.

### Claim 15 (depends on 14)

An epoxy resin composition comprising the epoxy resin curing agent of claim 14, and an epoxy resin.

### Claim 16 (depends on 15)

A carbon fiber-reinforced composite material comprising a cured product of the epoxy resin composition of claim 15, and carbon fibers.