Curable composition, cured product of the curable composition, and method of producing a cured product using the curable composition

Patent metadata

Field	Value
Publication number	US-10479879-B2
Application number	US-201815904857-A
Country	US
Kind code	B2
Filing date	Feb 26, 2018
Priority date	Mar 2, 2017
Publication date	Nov 19, 2019
Grant date	Nov 19, 2019

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.

First claim

What is claimed is:

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 R 1 and R 2 independently represent a group represented by the following formula (a2); R 1 and R 2 may be bonded to each other to form a ring together with the sulfur atom in the formula; R 3 represents a group represented by the following formula (a3) or a group represented by the following formula (a4); A 1 represents S, O, or Se; X − represents a monovalent anion; and wherein both of R 1 and R 2 do not represent an alkyl group optionally substituted with a halogen atom,

wherein a ring Z 1 represents an aromatic hydrocarbon ring; R 4 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 R 5 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); R 6 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); A 2 represents a single bond, S, O, a sulfinyl group, or a carbonyl group; and n1 represents 0 or 1,

wherein R 7 and R 8 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); R 9 and R 10 independently represent an alkyl group optionally substituted with a halogen atom or a group represented by the formula (a2); R 9 and R 10 may be bonded to each other to form a ring together with the sulfur atom in the formula; A 3 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 R 9 and R 10 are an alkyl group optionally substituted with a halogen atom)

wherein a ring Z 2 represents an aromatic hydrocarbon ring; R 11 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 Z 3 represents an aromatic hydrocarbon ring; R 12 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).

2. The curable composition according to claim 1 , wherein the aromatic vinyl ether compound (B) is a compound represented by the following formula (1):

wherein W 1 and W 2 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 W 1 and W 2 is a group represented by the following formula (2); a ring Y 1 and a ring Y 2 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—; R 3a and R 3b 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—; R 2b represents a monovalent hydrocarbon group, a hydroxy group, a group represented by —OR 3a , a group represented by —SR 3b , 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 —NHR 3c , a group represented by —N(R 3d ) 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 —OR 3a , a gro

Assignees

• Tokyo Ohka Kogyo Co Ltd

Inventors

• Someya Kazuya
• Chisaka Hiroki
• Matsumoto naozumi
• Shiota Dai

Classifications

• C09D4/00 Primary

  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} · CPC title

• C08L29/10 Primary

  Homopolymers or copolymers of unsaturated ethers (C08L35/08 takes precedence) · CPC title

• C08K5/55

  Boron-containing compounds {(C08K5/0091 takes precedence)} · CPC title

• G03F7/027

  Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds (G03F7/075 takes precedence) · CPC title

• C08J3/243

  Two or more independent types of crosslinking for one or more polymers · CPC title