Curable resin composition, molded article and method for producing same

Patent metadata

Field	Value
Publication number	US-12545756-B2
Application number	US-202117925352-A
Country	US
Kind code	B2
Filing date	May 20, 2021
Priority date	May 27, 2020
Publication date	Feb 10, 2026
Grant date	Feb 10, 2026

Abstract

A curable resin composition contains a polycarbonate resin and a styrenic monomer, the polycarbonate resin comprising a terminal structure that has an unsaturated group represented by the following Formula (1):and a constitutional unit represented by the following Formula (2):

First claim

The invention claimed is:

1 . A curable resin composition comprising a polycarbonate resin and a styrenic monomer, the polycarbonate resin comprising:
a terminal structure that is derived from a (meth)acrylic monohydric phenol compound and is represented by Formula (1):

wherein A is a vinyl group or an isopropenyl group,
R 1 is a single bond and R 2 is selected from the group consisting of a single bond and a substituted or unsubstituted alkylene group having 1 to 20 carbon atoms,
R 3 is each independently selected from the group consisting of a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 12 carbon atoms, and a substituted or unsubstituted heteroaryl group having 5 to 12 elements,
Z is —OC(═O)—,
a is an integer of 1 to 3,
b is an integer of 2 to 4, and
Y is an ether group or an ester group; and
a constitutional unit represented by Formula (2):

wherein R 4 is each independently selected from the group consisting of a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 12 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 5 carbon atoms, and a substituted or unsubstituted aralkyl group having 7 to 17 carbon atoms,
c is each independently an integer of 0 to 4,
X is selected from the group consisting of —C(R 5 )(R 6 )—, —S—, —(CH 2 ) d —, —O—, —SO—, —CO—, —SO 2 —, and groups represented by Formulae (3) to (6):

wherein R 5 and R 6 are each independently a hydrogen atom, a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 5 carbon atoms, a substituted or unsubstituted aryl group having 6 to 12 carbon atoms, or a carbocyclic group having 5 to 20 carbon atoms or a heterocyclic group having 5 to 12 elements formed by binding of R 5 and R 6 ,
R 7 is each independently a hydrogen atom, a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, a substituted or unsubstituted alkyl group having 1 to 9 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 5 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 12 carbon atoms,
R 8 is each independently a substituted or unsubstituted alkylene group having 1 to 9 carbon atoms,
d is an integer of 0 to 20, and
e is an integer of 1 to 500, and
provided that X is not —C(CH 3 ) 2 -when both c are 0.

2 . The curable resin composition according to claim 1 , wherein the constitutional unit represented by Formula (2) contains at least one selected from the group consisting of Formulae (7) to (13):

3 . The curable resin composition according to claim 1 , wherein the constitutional unit represented by Formula (2) is derived from a bisphenol compound.

4 . The curable resin composition according to claim 3 , wherein the bisphenol compound comprises at least one selected from the group consisting of 2,2-bis(4-hydroxy-3-methylphenyl) propane, 2,2-bis(4-hydroxyphenyl) butane, 2,2-bis(4-hydroxyphenyl)-4-methylpentane, 1,1-bis(4-hydroxyphenyl) ethane, 1,1-bis(4-hydroxyphenyl)cyclohexane, 1,1-bis(4-hydroxyphenyl)-1-phenylmethane, and 1,1-bis(4-hydroxyphenyl)-3,3,5-trimethylcyclohexane.

5 . The curable composition according to claim 1 , wherein the polycarbonate resin further comprises a constitutional unit derived from bisphenol A represented by the following formula:

6 . The curable resin composition according to claim 1 , wherein, in Formula (1),
A is an isopropenyl, R 2 is a single bond or an ethylene group, and R 3 is each independently a hydrogen atom or a benzotriazolyl group.

7 . The curable resin composition according to claim 6 , wherein the terminal structure having the unsaturated group represented by Formula (1) is derived from 2-[2-hydroxy-5-[2-(methacryloyloxy)ethyl]phenyl]-2H-benzotriazole.

8 . The curable resin composition according to claim 1 , wherein the styrenic monomer comprises styrene.

9 . The curable resin composition according to claim 1 , further comprising a radical polymerization initiator.

10 . The curable resin composition according to claim 1 , wherein the polycarbonate resin has a limiting viscosity of 0.3 to 2.0 dL/g.

11 . The curable resin composition according to claim 1 , wherein the terminal structure having the unsaturated group represented by Formula (1) is contained in an amount of 0.2 mol % or more with respect to the constitutional unit represented by Formula (2).

12 . A molded article formed by curing the curable resin composition according to claim 1 .

13 . The molded article according to claim 12 , being a cast-molded article.

14 . A method for producing a molded article, comprising curing the curable resin composition according to claim 1 .

15 . The curable composition according to claim 2 , wherein the polycarbonate resin further comprises a constitutional unit derived from bisphenol A represented by the following formula:

16 . The curable resin composition according to claim 2 , wherein, in Formula (1),
A is an isopropenyl group, R 2 is a single bond or an ethylene group, and R 3 is each independently a hydrogen atom or a benzotriazolyl group.

17 . The curable resin composition according to claim 15 , wherein, in Formula (1),
A is an isopropenyl group, R 2 is a single bond or an ethylene group, and R 3 is each independently a hydrogen atom or a benzotriazolyl group.

Assignees

• Mitsubishi Gas Chemical Co

Inventors

• Ogawa Noriyoshi
• ISHIKAWA Shun

Classifications

• C08G64/04

  Aromatic polycarbonates · CPC title

• C08F290/06

  Polymers provided for in subclass C08G · CPC title

• C08G64/24 Primary

  and phenols · CPC title

• C08G64/14

  containing a chain-terminating or -crosslinking agent · CPC title

• C08L2203/30

  used for thermoforming · CPC title