# US 10,479,879 B2 · Curable composition, cured product of the curable composition, and method of producing a cured product using the curable composition

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- Number: US 10,479,879 B2
- Document ID: US10479879B2
- Status: Granted
- Kind: B2
- Application number: 15/904,857
- Filed: 2018-02-26
- Published: 2018-09-06
- Granted: 2019-11-19
- Earliest claimed: 2017-03-02
- Assignees: Tokyo Ohka Kogyo Co., Ltd.
- Applicants: Tokyo Ohka Kogyo Co., Ltd.
- Inventors: Kazuya Someya; Hiroki Chisaka; Naozumi Matsumoto; Dai Shiota
- Web page: https://patentgrep.com/patent/US10479879B2

## CPC

- C08K 5/372: Sulfides {, e.g. R-(S)x-R'}
- C08J 3/24: Crosslinking, e.g. vulcanising, of macromolecules (mechanical aspects B29C35/00; crosslinking agents C08K)
- C08J 3/243: {Two or more independent types of crosslinking for one or more polymers}
- C08J 3/28: Treatment by wave energy or particle radiation
- C08K 5/55: Boron-containing compounds {(C08K5/0091 takes precedence)}
- C08L 29/10: Homopolymers or copolymers of unsaturated ethers (C08L35/08 takes precedence)
- C09D 4/00: Coating compositions, e.g. paints, varnishes or lacquers, based on organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond {; Coating compositions, based on monomers of macromolecular compounds of groups C09D183/00 - C09D183/16}
- C08K: Use of inorganic or non-macromolecular organic substances as compounding ingredients (paints, inks, varnishes, dyes, polishes, adhesives C09)
- 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)
- C08L: COMPOSITIONS OF MACROMOLECULAR COMPOUNDS (compositions based on polymerisable monomers C08F, C08G; artificial filaments or fibres D01F; textile treating compositions D06)
- C09D: COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR (cosmetics A61K; processes for applying liquids or other fluent materials to surfaces, in general, B05D; staining wood B27K5/02; glazes or vitreous enamels C03C; natural resins, French polish, drying-oils, driers, turpentine, per se, C09F; polishing compositions other than French polish, ski waxes C09G; adhesives or use of materials as adhesives C09J; materials for sealing or packing joints or covers C09K3/10; materials for stopping leaks C09K3/12; processes for the electrolytic or electrophoretic production of coatings C25D)

## Abstract

A cationically polymerizable curable composition comprising a compound having a vinyloxy group bonded to an aromatic group which is easily cured upon light exposure and/or heating, a cured product of the curable composition, and a method of producing a cured product using the curable composition. In a cationically polymerizable curable composition that includes a compound having a vinyloxy group bonded to an aromatic group, a sulfonium salt having a specific structure is used as a curing agent. A cured product is produced by shaping the curable composition into a predetermined shape, and subjecting the shaped curable composition to light exposure and/or heating.

## Claims

### Claim 1

A curable composition comprising a cationic polymerization initiator (A) and an aromatic vinyl ether compound (B),
the aromatic vinyl ether compound (B) comprising an aromatic group substituted with a vinyloxy group,
the cationic polymerization initiator (A) comprising a sulfonium salt represented by the following formula (a1):
wherein R1 and R2 independently represent a group represented by the following formula (a2); R1 and R2 may be bonded to each other to form a ring together with the sulfur atom in the formula; R3 represents a group represented by the following formula (a3) or a group represented by the following formula (a4); A1 represents S, O, or Se; X− represents a monovalent anion; and wherein both of R1 and R2 do not represent an alkyl group optionally substituted with a halogen atom,
wherein a ring Z1 represents an aromatic hydrocarbon ring; R4 represents an alkyl group optionally substituted with a halogen atom, a hydroxy group, an alkoxy group, an alkylcarbonyl group, an alkoxycarbonyl group, an acyloxy group, an alkylthio group, a thienyl group, a thienylcarbonyl group, a furanyl group, a furanylcarbonyl group, a selenophenyl group, a selenophenylcarbonyl group, a heterocyclic aliphatic hydrocarbon group, an alkylsulfinyl group, an alkylsulfonyl group, a hydroxy(poly)alkyleneoxy group, an optionally substituted amino group, a cyano group, a nitro group, or a halogen atom; and m1 represents an integer of 0 or more,
wherein R5 represents an alkylene group optionally substituted with a hydroxy group, an alkoxy group, an alkylcarbonyl group, an arylcarbonyl group, an alkoxycarbonyl group, an aryloxycarbonyl group, an arylthiocarbonyl group, an acyloxy group, an arylthio group, an alkylthio group, an aryl group, a heterocyclic hydrocarbon group, an aryloxy group, an alkylsulfinyl group, an arylsulfinyl group, an alkylsulfonyl group, an arylsulfonyl group, a hydroxy(poly)alkyleneoxy group, an optionally substituted amino group, a cyano group, a nitro group, or a halogen atom or a group represented by the following formula (a5); R6 represents an alkyl group optionally substituted with a hydroxy group, an alkoxy group, an alkylcarbonyl group, an arylcarbonyl group, an alkoxycarbonyl group, an aryloxycarbonyl group, an arylthiocarbonyl group, an acyloxy group, an arylthio group, an alkylthio group, an aryl group, a heterocyclic hydrocarbon group, an aryloxy group, an alkylsulfinyl group, an arylsulfinyl group, an alkylsulfonyl group, an arylsulfonyl group, a hydroxy(poly)alkyleneoxy group, an optionally substituted amino group, a cyano group, a nitro group, or a halogen atom or a group represented by the following formula (a6); A2 represents a single bond, S, O, a sulfinyl group, or a carbonyl group; and n1 represents 0 or 1,
wherein R7 and R8 independently represent an alkylene group optionally substituted with a hydroxy group, an alkoxy group, an alkylcarbonyl group, an arylcarbonyl group, an alkoxycarbonyl group, an aryloxycarbonyl group, an arylthiocarbonyl group, an acyloxy group, an arylthio group, an alkylthio group, an aryl group, a heterocyclic hydrocarbon group, an aryloxy group, an alkylsulfinyl group, an arylsulfinyl group, an alkylsulfonyl group, an arylsulfonyl group, a hydroxy(poly)alkyleneoxy group, an optionally substituted amino group, a cyano group, a nitro group, or a halogen atom or a group represented by the following formula (a5); R9 and R10 independently represent an alkyl group optionally substituted with a halogen atom or a group represented by the formula (a2); R9 and R10 may be bonded to each other to form a ring together with the sulfur atom in the formula; A3 represents a single bond, S, O, a sulfinyl group, or a carbonyl group; X− is the same as defined above; n2 represents 0 or 1; and not both of R9 and R10 are an alkyl group optionally substituted with a halogen atom)
wherein a ring Z2 represents an aromatic hydrocarbon ring; R11 represents an alkyl group optionally substituted with a halogen atom, a hydroxy group, an alkoxy group, an alkylcarbonyl group, an arylcarbonyl group, an alkoxycarbonyl group, an aryloxycarbonyl group, an arylthiocarbonyl group, an acyloxy group, an arylthio group, an alkylthio group, an aryl group, a heterocyclic hydrocarbon group, an aryloxy group, an alkylsulfinyl group, an arylsulfinyl group, an alkylsulfonyl group, an arylsulfonyl group, a hydroxy(poly)alkyleneoxy group, an optionally substituted amino group, a cyano group, a nitro group, or a halogen atom; and m2 represents an integer of 0 or more,
wherein a ring Z3 represents an aromatic hydrocarbon ring; R12 represents an alkyl group optionally substituted with a halogen atom, a hydroxy group, an alkoxy group, an alkylcarbonyl group, an arylcarbonyl group, an alkoxycarbonyl group, an aryloxycarbonyl group, an arylthiocarbonyl group, an acyloxy group, an arylthio group, an alkylthio group, a thienylcarbonyl group, a furanylcarbonyl group, a selenophenylcarbonyl group, an aryl group, a heterocyclic hydrocarbon group, an aryloxy group, an alkylsulfinyl group, an arylsulfinyl group, an alkylsulfonyl group, an arylsulfonyl group, a hydroxy(poly)alkyleneoxy group, an optionally substituted amino group, a cyano group, a nitro group, or a halogen atom; and m3 represents an integer of 0 or more).

### Claim 2 (depends on 1)

The curable composition according to claim 1, wherein the aromatic vinyl ether compound (B) is a compound represented by the following formula (1):
wherein W1 and W2 independently represent a group represented by the following formula (2), a group represented by the following formula (3), or a hydroxy group; at least one of W1 and W2 is a group represented by the following formula (2); a ring Y1 and a ring Y2 represent the same aromatic hydrocarbon ring or different aromatic hydrocarbon rings; R represents a single bond, a methylene group optionally having a substituent, an ethylene group optionally having a substituent and optionally having a heteroatom between the two carbon atoms, a group represented by —O—, a group represented by —NH—, or a group represented by —S—; R3a and R3b independently represent a cyano group, a halogen atom, or a monovalent hydrocarbon group; and n1 and n2 independently represent an integer of 0 or more and 4 or less,
wherein a ring Z represents an aromatic hydrocarbon ring; X represents a single bond or a group represented by —S—; R2b represents a monovalent hydrocarbon group, a hydroxy group, a group represented by —OR3a, a group represented by —SR3b, an acyl group, an alkoxycarbonyl group, a halogen atom, a nitro group, a cyano group, a mercapto group, a carboxyl group, an amino group, a carbamoyl group, a group represented by —NHR3c, a group represented by —N(R3d)2, a (meth)acryloyloxy group, a sulfo group, or a group formed by substituting at least a part of hydrogen atoms bonded to carbon atoms comprised in a monovalent hydrocarbon group, a group represented by —OR3a, a group represented by —SR3b, an acyl group, an alkoxycarbonyl group, a group represented by —NHR3c, or a group represented by —N(R3d)2 with a monovalent hydrocarbon group, a hydroxy group, a group represented by —OR3a, a group represented by —SR3b, an acyl group, an alkoxycarbonyl group, a halogen atom, a nitro group, a cyano group, a mercapto group, a carboxyl group, an amino group, a carbamoyl group, a group represented by —NHR3c, a group represented by —N(R3d)2, a (meth)acryloyloxy group, a mesyloxy group, or a sulfo group; R3a to R3d independently represent a monovalent hydrocarbon group; and m represents an integer of 0 or more,
wherein R1b represents a single bond or an alkylene group having 1 or more and 4 or less carbon atoms; and each of ring Z, X, R2b, and m is the same as defined above in formula (2).

### Claim 3 (depends on 2)

The curable composition according to claim 2, wherein each of W1 and W2 is a group represented by the formula (2) and the ring Z is a naphthalene ring.

### Claim 4 (depends on 1)

The curable composition according to claim 1, wherein the aromatic vinyl ether compound (B) is a compound comprising a fluorene ring.

### Claim 5 (depends on 1)

The curable composition according to claim 1, wherein each of R1 and R2 in the formula (a1) represents the group represented by the formula (a2) and
wherein the group is a phenyl group.

### Claim 6 (depends on 1)

The curable composition according to claim 1, wherein A1 in the formula (a1) is S.

### Claim 7 (depends on 1)

The curable composition according to claim 1, wherein X− in the formula (a1) is an anion selected from the group consisting of SbF6−, PF6−, (CF3CF2)3PF3−, (C6F5)4B−, ((CF3)2C6H3)4B−, (C6F5)4Ga−, ((CF3)2C6H3)4Ga−, and (CF3SO2)3C−.

### Claim 8 (depends on 1)

The curable composition according to claim 1, wherein the cationic polymerization initiator (A) is comprised in a content of 0.01 parts by mass or more and 30 parts by mass or less in relation to 100 parts by mass of the aromatic vinyl ether compound (B).

### Claim 9 (depends on 1)

A cured product formed by curing the curable composition according to claim 1.

### Claim 10 (depends on 1)

A method of producing a cured product, the method comprising:
shaping the curable composition according to claim 1 into a predetermined shape; and
subjecting the shaped curable composition to at least one of light exposure and heating.

### Claim 11 (depends on 10)

The method of producing a cured product according to claim 10, wherein the shaping of the curable composition is formation of a coating film, and the coating film is subjected to at least one of light exposure and heating.

### Claim 12 (depends on 10)

The method of producing a cured product according to claim 10, wherein the shaped curable composition is subjected to light exposure and heating.