# US 2019/0169387 A1 · Prepreg sheet and manufacturing method of fiber-reinforced composite material

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- Number: US 2019/0169387 A1
- Document ID: US20190169387A1
- Status: Published application
- Kind: A1
- Application number: 16/304,610
- Filed: 2017-03-30
- Published: 2019-06-06
- Earliest claimed: 2016-05-30
- Assignees: Japan U-Pica Company, Ltd.
- Applicants: Japan U-Pica Company, Ltd.
- Inventors: Tetsuji MOROIWA; Nozomi ISHINE
- Web page: https://patentgrep.com/patent/US20190169387A1

## CPC

- C08F 290/067: {Polyurethanes; Polyureas}
- C08F 290/06: Polymers provided for in subclass C08G
- C08F 299/06: from polyurethanes
- C08J 5/243: {using carbon fibres}
- C08G 18/8175: {with esters of acrylic or alkylacrylic acid having only one group containing active hydrogen}
- C08J 2375/16: having terminal carbon-to-carbon unsaturated bonds
- C08F: MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- 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)
- C08G: MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS

## Abstract

The purpose of the present invention is to provide a prepreg sheet including a radical-polymerizable resin composition contributing to excellent mechanical properties of a fiber reinforced plastic, excellent curability with storability. The prepreg sheet of the present invention is obtained by infiltrating a radical-polymerizable resin composition into fibers, and is characterized in that the radical-polymerizable resin composition contains at least a urethane (meth) acrylate compound (a) represented by the following chemical formula [Chemical 1]: XM[n ]Chemical 1] (in the formula, wherein n is within a range from 2 to 100, X is a compound residue having two or more isocyanate groups, and M contains at least formula [Chemical 2]: —N═C═O [Chemical 2] in the formula [Chemical 3], Q represents a mono alcohol compound residue containing ethylenically unsaturated groups.).

## Claims

### Claim 1

A prepreg sheet obtained by impregnating a fiber with a radical polymerizable resin composition, wherein the radical polymerizable resin composition contains at least a urethane (meth) acrylate compound (a) represented by the following chemical formula [Chemical 1]:
XM]n [Chemical 1]
(in the formula [Chemical 1], wherein n is within a range from 2 to 100, X is a compound residue having two or more isocyanate groups, and M contains at least a formula [Chemical 2]:
—N═C═O [Chemical 2]
and M other than the above formula [Chemical 2] is a formula [Chemical 3]:
in the formula [Chemical 3], Q represents a residue of a mono alcohol compound residue containing an ethylenically unsaturated group).

### Claim 2 (depends on 1)

A prepreg sheet according to claim 1 wherein the chemical formula [Chemical 1] is represented by the following chemical formula [Chemical 4]:
(in the formula, wherein n is within a range from 1 to 5000, X is a compound residue having two or more isocyanate groups, Y is an alcohol compound residue having two or more hydroxyl groups and M contains at least formula [Chemical 5]:
—N═C═O [Chemical 5]
and the M other than the above formula [Chemical 5] is formula [Chemical 6]:
Moreover, in the formula [Chemical 6], Q represents a mono alcohol compound residue containing ethylenically unsaturated groups).

### Claim 3 (depends on 1)

A prepreg sheet according to claim 1 wherein the urethane (meth) acrylate compound (a) contains 0.1 to 12 percent by weight of an isocyanate group.

### Claim 4 (depends on 1)

A prepreg sheet according to claim 1, wherein an amount of the polymerizable vinyl monomer in the radical polymerizable resin composition is between 0 and 50 percent by weight.

### Claim 5 (depends on 1)

A prepreg sheet according to claim 1, wherein the polymerizable vinyl monomer in the radical polymerizable resin composition includes one or more kinds selected from phenoxyethyl methacrylate, benzyl methacrylate, isobornyl methacrylate, tricyclodecanedimethanol dimethacrylate.

### Claim 6 (depends on 1)

A method for manufacturing a fiber-reinforced composite material, comprising a step of curing the prepreg sheet according to claim 1.