Ene-thiol-type curable composition and cured product thereof

Patent metadata

Field	Value
Publication number	US-2016145392-A1
Application number	US-201414896692-A
Country	US
Kind code	A1
Filing date	Jun 11, 2014
Priority date	Jun 17, 2013
Publication date	May 26, 2016
Grant date	—

Abstract

An ene-thiol based curable composition according to the present invention includes:
(A) a thiol compound having two or more groups represented by a following general formula (1) in the molecule; and (B) an ene oligomer having an alicyclic or aromatic ring structure and two or more ethylenically unsaturated groups in the molecule, with a number average molecular weight of 500 to 20,000 in terms of polystyrene.

In the following general formula (1), each of R 1 and R 2 independently represents a hydrogen atom, an alkyl group having 1 to 10 carbon atoms, or an aromatic group having 6 to 10 carbon atoms; a is an integer of 0 to 2; and b is 0 or 1.

First claim

1 . An ene-thiol based curable composition comprising:
(A) a thiol compound having two or more groups represented by a following general formula (1) in the molecule; and (B) an ene oligomer having an alicyclic or aromatic ring structure and two or more ethylenically unsaturated groups in the molecule, with a number average molecular weight of 500 to 20,000 in terms of polystyrene:

wherein in the general formula (1), each of R 1 and R 2 independently represents a hydrogen atom, an alkyl group having 1 to 10 carbon atoms, or an aromatic group having 6 to 10 carbon atoms; a is an integer of 0 to 2; and b is 0 or 1.

2 . The ene-thiol based curable composition according to claim 1 ,
wherein said ene oligomer (B) is a reaction product of a compound (B-1) having an alicyclic or aromatic ring and two or more ethylenically unsaturated groups in the molecule and a polyhydric alcohol (B-2).

3 . The ene-thiol based curable composition according to claim 1 ,
wherein said ene oligomer (B) is any one or more of oligomers represented by the following general formulae (2) to (4):

wherein in the general formula (2), c is an integer of 0 to 5; R 3 is an alkylene group having 1 to 10 carbon atoms in the main chain which may have an alkyl group of 1 to 5 carbon atoms as a substituent, and which may have an ether linkage inserted therewithin; X is a phenylene group or a cyclohexylene group which may have an alkyl group of 1 to 4 carbon atoms as a substituent; and n is an integer of 3 to 20,

wherein in the general formula (3), d is the same as c described above; R 4 is an alkyl group of 1 to 4 carbon atoms or a group represented by the following formula (3′); Y is the same as X described above; and m is an integer of 3 to 70,

wherein in the general formula (3′), d and Y are the same as described above in the general formula (3),

wherein in the general formula (4), e is the same as c described above; each of R 5 and R 6 independently represents an alkylene group having 1 to 10 carbon atoms in the main chain which may have an alkyl group of 1 to 5 carbon atoms as a substituent; Z is the same as X described above; p is an integer of 1 to 10; and q is an integer of 5 to 50.

4 . The ene-thiol based curable composition according to claim 1 , wherein b is 0 in said thiol compound (A).

5 . The ene-thiol based curable composition according to claim 1 ,
wherein said thiol compound (A) is a thiol compound (A1) having two or more groups represented by the general formula (1) in the molecule and having no hydroxyl group in the molecule.

6 . The ene-thiol based curable composition according to claim 1 ,
wherein said thiol compound (A) comprises both of a thiol compound (A1) having two or more groups represented by said general formula (1) in the molecule and having no hydroxyl group in the molecule, and a thiol compound (A2) having two or more groups represented by said general formula (1) in the molecule and having a hydroxyl group in the molecule.

7 . The ene-thiol based curable composition according to claim 6 , wherein said thiol compound (A2) accounts for from 0.1 to 30% by mass of said thiol compound (A).

8 . The ene-thiol based curable composition according to claim 5 , wherein said thiol compound (A1) is pentaerythritol tetrakis(3-mercaptobutyrate).

9 . The ene-thiol based curable composition according to claim 6 , wherein said thiol compound (A2) is pentaerythritol tris(3-mercaptobutyrate).

10 . The ene-thiol based curable composition according to claim 1 ,
wherein said thiol compound (A) and said ene oligomer (B) are included in such a manner that the ethylenically unsaturated group in said ene oligomer (B) is contained at a ratio of 0.5 to 10 mol relative to 1 mol of a mercapto group in said thiol compound (A).

11 . The ene-thiol based curable composition according to claim 1 , further comprising a photopolymerization initiator and/or a thermal polymerization initiator.

12 . A cured product which is formed by curing the ene-thiol based curable composition according to claim 1 .

Assignees

• Showa Denko Kk

Inventors

• TODA Asuka
• Shibuya Akira

Classifications

• C08G75/045 Primary

  from mercapto compounds and unsaturated compounds · CPC title

• C08G75/12

  Polythioether-ethers (C08G75/0245 takes precedence) · CPC title