Unsaturated group-containing ester compound, polymer, thermosetting resin composition, and cured film
It is an object of the present invention to provide an unsaturated group-containing ester compound which can be used as a raw material of a curable composition using transesterification reaction and which is inexpensive and has a good curability, and a polymer, a thermosetting resin composition, and a curable composition which containing the unsaturated group-containing ester compound, respectively. An unsaturated group-containing ester compound having a chemical structure represented by the following general formula (1): n 1 : 1 to 10 (in the formula, R 1 , R 2 , and R 3 are the same or different and each is a hydrogen, an alkyl group, a carboxyl group, an alkyl ester group or a structure represented by R 4 -[COOR 5 ]n 1 ; R 4 is an aliphatic, an alicyclic or an aromatic alkylene group with a number of atoms of 50 or less in the main chain, which may have one or more functional groups selected from the group consisting of an ester group, an ether group, an amide group, and a urethane and may have a side chain; R 5 is an alkyl group having 50 or less carbon atoms; and in the compound represented by the general formula (1), the R 4 -[COOR 5 ] group may be a lactone structure represented by the following general formula (1-1). (R x is a hydrocarbon group having 2 to 10 carbon atoms which may have a branched chain.
1. A thermosetting resin composition comprising a polymer (A) containing a structural unit derived from an unsaturated group-containing ester compound having a chemical structure represented by the following formula (3):
where:
R 9 is an alkyl group having 1 to 50 carbon atoms;
R 10 is an alkylene group with a number of atoms of 44 or less in the main chain, which may have an ester group, an ether group and/or an amide group in the main chain, and may have a side chain;
R 11 is H or a methyl group;
R 12 is an alkyl group having 50 or less carbon atoms;
R 13 is H or a methyl group;
n 3 is 0 or 1; and
n 4 is 1 or 2;
a hydroxyl group-containing compound (B) with at least two hydroxyl groups; and
a transesterification catalyst (F).
2. The thermosetting resin composition according to claim 1 , wherein R 12 is a tertiary alkyl group.
3. The thermosetting resin composition according to claim 1 , wherein the hydroxyl group-containing compound (B) is a polymer containing a structural unit derived from the monomer represented by the following formula (4) in at least a portion thereof:
where:
m 1 is from 1 to 10;
R 21 , R 22 , and R 23 are the same or different and each is a hydrogen, an alkyl group, a carboxyl group, an alkyl ester group or a structure represented by the following R 24 -[OH]m 1 ; and
R 24 is an aliphatic, an alicyclic or an aromatic alkylene group with a number of atoms of 3 to 50 in the main chain, which may have one or more functional groups selected from the group consisting of an ester group, an ether group, an amide group, and a urethane and may have a side chain.
4. A thermosetting resin composition comprising:
a polymer (C) containing a structural unit derived from the unsaturated group-containing ester compound represented by the formula (3):
where:
R 9 is an alkyl group having 1 to 50 carbon atoms;
R 10 is an alkylene group with a number of atoms of 44 or less in the main chain, which may have an ester group, an ether group and/or an amide group in the main chain, and may have a side chain;
R 11 is H or a methyl group;
R 12 is an alkyl group having 50 or less carbon atoms;
R 13 is H or a methyl group;
n 3 is 0 or 1; and
n 4 is 1 or 2;
a structural unit derived from a hydroxyl group-containing unsaturated monomer as an essential constituting unit; and
a transesterification catalyst (F).
5. The thermosetting resin composition according to claim 4 , wherein R 12 is a tertiary alkyl group.
6. The thermosetting resin composition according to claim 4 , wherein the structural unit derived from the hydroxyl group-containing unsaturated monomer contains a structural unit derived from the monomer represented by the following formula (4) in at least a portion thereof:
where:
m 1 is from 1 to 10;
R 21 , R 22 , and R 23 are the same or different and each is a hydrogen, an alkyl group, a carboxyl group, an alkyl ester group or a structure represented by the following R 24 -[OH]m 1 ; and
R 24 is an aliphatic, an alicyclic or an aromatic alkylene group with a number of atoms of 3 to 50 in the main chain, which may have one or more functional groups selected from the group consisting of an ester group, an ether group, an amide group, and a urethane and may have a side chain.
7. A cured film formed by three-dimensionally crosslinking the thermosetting resin composition according to claims 1 or 4 .
8. An unsaturated group-containing ester compound having a chemical structure represented by the following formula (3):
where:
R 9 is an alkyl group having 1 to 50 carbon atoms;
R 10 is an alkylene group with a number of atoms of 44 or less in the main chain, which may have an ester group, an ether group and/or an amide group in the main chain, and may have a side chain;
R 11 is H or a methyl group;
R 12 is an alkyl group having 50 or less carbon atoms;
R 13 is H or a methyl group;
n 3 is 0 or 1; and
n 4 is 1 or 2.
9. The unsaturated group-containing ester compound according to claim 8 , wherein R 12 is a tertiary alkyl group.
10. A polymer (A) containing a structural unit derived from the unsaturated group-containing ester compound according to claim 8 or 9 in at least a portion thereof.
11. A polymer (C) containing a structural unit derived from the unsaturated group-containing ester compound according to claim 8 or 9 and a structural unit derived from a hydroxyl group-containing unsaturated monomer as an essential constituting unit.
12. The polymer (C) according to claim 9 , wherein the structural unit derived from the hydroxyl group-containing unsaturated monomer contains a structural unit derived from the monomer represented by the following formula (4) in at least a portion thereof:
where:
m 1 is from 1 to 10;
R 21 , R 22 , and R 23 are the same or different and each is a hydrogen, an alkyl group, a carboxyl group, an alkyl ester group or a structure represented by the following R 24 -[OH]m 1 ; and
R 24 is an aliphatic, an alicyclic or an aromatic alkylene group with a number of atoms of 3 to 50 in the main chain, which may have one or more functional groups selected from the group consisting of an ester group, an ether group, an amide group, and a urethane and may have a side chain.