Radical polymerization initiator, composition containing same, cured product of composition, production method for cured product, and compound

1. A radical polymerization initiator, comprising a compound represented by the following, Formula (A):

wherein,

Z 1 represents a direct bond, —NR 101 —, —S—, —SO—, or —CO—;

Z 2 represents —C(R 102 ) 2 —, NR 101 —, —O—, —S—, —SO—, or —CO—;

R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 and R 8 each independently represent a hydrogen atom, CN, NO 2 , a hydroxy group, an alkyl group having 1 to 20 carbon, atoms, an aryl group having 6 to 30 carbon atoms which is optionally substituted with an alkyl group, an arylalkyl group having 7 to carbon atoms which is optionally substituted with an alkyl group, a heterocycle-containing group having 2 to 20 carbon atoms, or a group containing a salt-forming group, which is represented by the following Formula (B1):

*-L 1 B) b   (B1))

wherein,

L 1 represents a direct bond or a (b+1)-valent linking group,

B represents an acidic group salt or a basic group salt,

b represents an integer of 1 to 10, and

the asterisk (*) represents a site of binding with a benzene ring;

at least one of R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 and R 8 is the group containing the salt-forming group of Formula (B1);

R 101 and R 102 each independently represent a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 30 carbon atoms which is optionally substituted with an alkyl group, an arylalkyl group having 7 to 30 carbon atoms which is optionally substituted with an alkyl group, or a heterocycle-containing group having 2 to 20 carbon atoms;

one or more hydrogen atoms in the alkyl group, the aryl group optionally substituted with an alkyl group, the arylalkyl group optionally substituted with an alkyl group, and the heterocycle-containing group, which groups are used as R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 and R 8 and R 101 and R 102 , are optionally substituted with an ethylenically unsaturated group, a halogen atom, an acyl group, an acyloxy group, a substituted amino group, a sulfonamide group, a sulfonyl group, a carboxyl group, a cyano group, a sulfo group, a hydroxy group, a nitro group, a mercapto group, an imide group, a carbamoyl group, a phosphonate group, or a phosphate group;

one or more methylene groups in the alkyl group, the aryl group optionally substituted with an alkyl group, the arylalkyl group optionally substituted with an alkyl group, and the heterocycle-containing group, which groups are used as R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 and R 8 and R 101 and R 102 , are optionally substituted with a carbon-carbon double bond, —O—, —S—, —CO—, —O—CO—, —CO—O—, —OCO—O—, —O—CO—O—, —S—CO—, —CO—S—, —S—CO—O—, —O—CO—S—, —CO—NH—, —NH—CO—, —NH—CO—O—, —NR′—, —S—S—, —SO 2 —, or a combination of groups selected from the above such that oxygen atoms are not arranged adjacent to one another;

adjacent groups of R 1 and R 2 , R 2 and R 3 , R 3 and R 4 , R 5 and R 6 , R 6 and R 7 , and R 7 and R 8 are optionally bound together to form a ring, and optionally form a fused ring with a benzene ring constituting a three-membered ring in Formula (A); and

R′ represents a hydrogen atom or an alkyl group having 1 to 8 carbon atoms,

wherein the radical polymerization initiator satisfies at least one of the following conditions (i) to (iv):

(i) B is the acidic group salt, and a cationic component constituting the acidic group salt is a potassium ion;

(ii) B is the acidic group salt, and a cationic component constituting the acidic group salt is an amine cation;

(iii) L 1 is the direct bond, and when B is the acidic group salt, an anionic group constituting the acidic group salt is an anionic group other than a sulfonic acid ion group

(iv) R 4 in Formula (A) is the group containing the salt-forming group of Formula (B1).

2. The radical polymerization initiator according to claim 1 , wherein the compound has a maximum absorption wavelength of 380 nm or longer in a range of 300 nm to 600 nm.

3. The radical polymerization initiator according to claim 1 , wherein a combination of Z 1 and Z 2 is a combination of —S— and —CO—.

4. The radical polymerization initiator according to claim 1 , wherein

the radical polymerization initiator satisfies condition (iii), and

B is the acidic group salt.

5. The radical polymerization initiator according to claim 1 , wherein

B is the acidic group salt, and

an anionic group constituting the acidic group salt is a carboxylic acid ion group.

6. The radical polymerization initiator according to claim 1 , wherein the compound has a solubility of not less than 0.5 parts by mass in 100 parts by mass of water.

7. The radical polymerization initiator according to claim 1 , further comprising a compound represented by the following Formula (1):

wherein,

represents an aryl group having 6 to 15 carbon atoms which optionally has a substituent;

X 2 represents a linear alkyl group having 1 to 8 carbon atoms, a branched alkyl group having 3 to 8 carbon atoms, a linear alkoxy group having 1 to 8 carbon atoms, a branched alkoxy group having 3 to 8 carbon atoms, or an aryl group having 6 to 15 carbon atoms which optionally has a substituent;

A m+ represents, an m-valent cationic component;

m represents a number of 1 to 3;

one or more hydrogen atoms in the aryl group used as X 1 and X 2 and the alkyl group or alkoxy group used as X 2 are optionally substituted with an ethylenically unsaturated group, a halogen atom, an acyl group, an acyloxy group, a substituted amino group, a sulfonamide group, a sulfonyl group, a carboxyl group, a cyano group, a sulfo group, a hydroxy group, a nitro group, a mercapto group, an imide group, a carbamoyl group, a phosphonate group, or a phosphate group;

one or more methylene groups in the aryl group used as X 1 and X 2 and the alkyl group or alkoxy group used as X 2 are optionally substituted with a carbon-carbon double bond, —O—, —S—, —CO—, —O—CO—, —CO—O—, —OCO—O—, —O—CO—O—, —S—CO—, —CO—S—, —S—CO—O—, —O—CO—S—, —CO—NH—, —NH—CO—, —NH—CO—O—, —NR′—, —S—S—, —SO 2 —, or a combination of groups selected from the above such that oxygen atoms are not arranged adjacent to one another; and

R′ represents a hydrogen atom or an alkyl group having 1 to 8 carbon atoms.

8. A composition comprising:

a compound represented by the following Formula (A):

wherein,

Z 1 represents a direct bond, —NR 101 —, —O—, —S—, —SO—, or —CO—;

Z 2 represents —C(R 102 ) 2 —, N—R 101 —, —O—, —S—, —SO—, or —CO—;

R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 and R 8 each independently represent a hydrogen atom, CN, NO 2 , a hydroxy group, an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 30 carbon atoms which is optionally substituted with an alkyl group, an arylalkyl group having 7 to 30 carbon atoms which is optionally substituted with an alkyl group, a heterocycle-containing group having 2 to 20 carbon atoms, or a group containing a salt-forming group, which is represented by the following Formula (B1):

*-L 1 B) b   (B1)

wherein,

L 1 represents a direct bond or a (b+1)-valent linking group,

B represents an, acidic group salt or a basic group salt,

b represents an integer of 1 to 10, and

the asterisk (*) represents a site of binding with, a benzene ring);

at least one of R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 and R 8 is the group containing the salt-forming group of Formula (B1);

R 101 and R 102 each independently represent a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 30 carbon atoms which is optionally substituted with an alkyl group, an arylalkyl group having 7 to 30 carbon atoms which is optionally substituted with an alkyl group, or a heterocycle-containing group having 2 to 20 carbon atoms;

one or more hydrogen atoms in the alkyl group, the aryl group optionally substituted with, an alkyl group, the arylalkyl group optionally substituted with an alkyl group, and the heterocycle-containing group, which groups are used as R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 and R 8 and R 101 and R 102 , are optionally substituted with an ethylenically unsaturated group, a halogen atom, an acyl group, an acyloxy group, a substituted amino group, a sulfonamide group, a sulfonyl group, a carboxyl group, a cyano group, a sulfa group, a hydroxy group, a nitro group, a mercapto group, an imide group, a carbamoyl group, a phosphonate group, or a phosphate group;

one or more methylene groups in the alkyl group, the aryl group optionally substituted with an alkyl group, the arylalkyl group optionally substituted with an alkyl group, and the heterocycle-containing, group, which groups are used as R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 and R 8 and R 101 and R 102 , are optionally substituted with a carbon-carbon double bond, —O—, —S—, —CO—, —O—CO—, —OO—O—, —OCO—O—, —O—CO—O—, —S—CO—, —CO—S—, —S—CO—O—, —O—CO—S—, —CO—NH—, —NH—CO—, —NH—CO—O—, —NR′—, —S—S—, —SO 2 —, or a combination of groups selected from the above such that oxygen atoms are not arranged adjacent to one another;

adjacent groups of R 1 and R 2 , R 2 and R 3 , R 3 and R 4 , R 5 and R 6 , R 6 and R 7 , and R 7 and R 8 are optionally bound together to form a ring, and optionally form a fused ring with a benzene ring constituting a three-membered ring in Formula (A); and

R′ represents a hydrogen atom or an alkyl group having 1 to 8 carbon atoms,

a radical polymerizable compound,

wherein the composition satisfies at least one of the following conditions (i) to (iv):

(i) B is the acidic group salt, and a cationic component constituting the acidic group salt is a potassium ion;

(ii) B is the acidic group salt, and a cationic component constituting the acidic group salt is an amine cation;

(iii) L 1 is the direct bond, and when B is the acidic group salt, an anionic group constituting the acidic group salt is an anionic group other than a sulfonic acid ion group

(iv) R 4 in Formula (A) is the group containing the salt-forming group of Formula (B1).

9. The composition according to claim 8 , further comprising a solvent that contains water.

10. The composition according, to claim 8 , further comprising a compound represented by the following Formula (I):

wherein,

X 1 represents an aryl group having 6 to 15 carbon atoms which optionally has a substituent;

X 2 represents a linear alkyl group having 1 to 8 carbon atoms, a branched alkyl group having 3 to 8 carbon atoms, a linear alkoxy group having 1 to 8 carbon atoms, a branched alkoxy group having 3 to 8 carbon atoms, or an aryl group having 6 to 15 carbon atoms which optionally has a substituent;

A m+ represents an m-valent cationic component;

m represents a number of 1 to 3;

one or more hydrogen atoms in the aryl group used as X 1 and X 2 and the alkyl group or alkoxy group used as X 2 are optionally substituted with an ethylenically unsaturated group, a halogen atom, an acyl group, an acyloxy group, a substituted amino group, a sulfonamide group, a sulfonyl group, a carboxyl group, a cyano group, a sulfo group, a hydroxy group, a nitro group, a mercapto group, an imide group, a carbamoyl group, a phosphonate group, or a phosphate group;

one or more methylene groups in the aryl group used as X 1 and X 2 and the alkyl group or alkoxy group used as X 2 are optionally substituted with a carbon-carbon double bond, —O—, —S−, —CO—, —O—CO—, —OO—O—, —OCO—O—, —O—CO—O—, —S—CO—, —CO—S—, —S—CO—O—, —O—CO—S—, —CO—NH—, —NH—CO—, —NH—CO—O—, —S—S—, —SO 2 —, or a combination of groups selected from the above such that oxygen atoms are not arranged adjacent to one another; and

R′ represents a hydrogen atom or an alkyl group having 1 to 8 carbon atoms.

11. A cured product, comprising the composition according to claim 8 .

12. A method of producing a cured product, the method comprising the step of irradiating the composition according to claim 8 with light.

13. A compound represented by the following Formula (A):

wherein,

Z 1 represents a direct bond, —NR 101 , —O—, —S—, —SO—, or —CO—;

Z 2 represents —C(R 102 ) 2 —, —NR 101 —, —O—, —S—, —SO—, or —CO—;

R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 and R 8 each independently represent a hydrogen atom, CN, NO 2 , a hydroxy group, an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 30 carbon atoms which is optionally substituted with an alkyl group, an arylalkyl group having 7 to 30 carbon atoms which is optionally substituted with an alkyl group, a heterocycle-containing group having 2 to 20 carbon atoms, or a group containing a salt-forming group, which is represented by the following Formula (B1):

*-L 1 B) b   (B1)

wherein,

L 1 represents a direct bond or a (b+1)-valent linking group,

B represents an acidic group salt or a basic group salt,

b represents an integer of 1 to 10, and

the asterisk (*) represents a site of binding with a benzene ring;

at least one of R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 and R 8 is the group containing salt-forming group of Formula (B1);

R 101 and R 102 each independently represent a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 30 carbon atoms which is optionally substituted with an alkyl group, an arylalkyl group having 7 to 30 carbon atoms which is optionally substituted with an alkyl group, or a heterocycle-containing group having 2 to 20 carbon atoms;

one or more hydrogen atoms in the alkyl group, the aryl group optionally substituted with an alkyl group, the arylalkyl group optionally substituted with an alkyl group, and the heterocycle-containing group, which groups are used as R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 and R 8 and R 101 and R 102 , are optionally substituted with an ethylenically unsaturated group, a halogen atom, an acyl group, an acyloxy group, a substituted amino group, a sulfonamide group, a sulfonyl group, a carboxyl group, a cyano group, a sulfo group, a hydroxy group, a nitro group, a mercapto group, an imide group, a carbamoyl group, a phosphonate group, or a phosphate group;

one or more methylene groups in the alkyl group, the aryl group optionally substituted with an alkyl group, the arylalkyl group optionally substituted with an alkyl group, and the heterocycle-containing group, which groups are used as R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 and R 8 and R 101 and R 102 , are optionally substituted with a carbon-carbon double bond, —O—, —S—, —CO—, —O—CO—, —CO—O—, —OCO—O—, —O—CO—O—, —S—CO—, —CO—S—, —S—CO—O—, —O—CO—S—, —CO—NH—, —NH—CO—, —NH—CO—O—, —NR′—, —S—S—, —SO 2 —, or a combination of groups selected from the above such that oxygen atoms are not arranged adjacent to one another;

adjacent groups of R 1 and R 2 , R 2 and R 3 , R 3 and R 4 , R 5 and R 6 , R 6 and R 7 , and R 7 and R 8 are optionally bound together to form a ring, and optionally form a fused ring with a benzene ring constituting a three-membered ring in Formula (A); and

R′ represents a hydrogen atom or an alkyl group having 1 to 8 carbon atoms,

wherein the compound satisfies at least one of the following conditions (i) to (iv);

(i) B is the acidic group salt, and a cationic component constituting the acidic group salt is a potassium ion;

(ii) B is the acidic group salt, and a cationic component constituting the acidic group salt is an amine cation;

(iii) L 1 is the direct bond, and when B is the acidic group salt, an anionic group constituting the acidic group salt is an anionic group other than a sulfonic acid ion group;

(iv) R 4 in Formula (A) is the group containing the salt-forming group of Formula (B1).

14. The compound according to claim 13 , wherein

the compound satisfies condition (iii),

a combination of Z 1 and Z 2 is a combination of —S— and —CO—,

B is the acidic group salt, and

an anionic group constituting the acidic group salt is a carboxylic acid ion group.

15. The compound according to claim 13 , wherein

the compound satisfies condition (ii), and

the amine cation is represented by the following Formula (C2), Formula (C3) or Formula (C4):

N + H 2 Y 1 Y 2   (C2)

N + HY 1 Y 2 Y 3   (C3)

N + Y 1 Y 2 Y 3 Y 4   (C4)

wherein

Y 1 , Y 2 , Y 3 and Y 4 each independently represents a hydroxy group, an alkyl group having 1 to 6 carbon atoms, an alkenyl group having 2 to 6 carbon atoms, an aryl group having 6 to 15 carbon atoms, or an arylalkyl group having 7 to 13 carbon atoms;

the hydrogen atoms in the groups represented by Y 1 , Y 2 , Y 3 and Y 4 may each be substituted with a hydroxy group; the methylene groups in the groups represented by Y 1 , Y 2 , Y 3 and Y 4 may each be substituted with an oxygen atom or —N + H—; and two or more of Y 1 , Y 2 , Y 3 and Y 4 may be bound together to form a ring; and

one or more hydrogen atoms in the groups represented by Y 1 , Y 2 , Y 3 and Y 4 are substituted with hydroxy groups, in two or more of Y 1 , Y 2 , Y 3 and Y 4 .

16. A method of generating a radical, wherein the method comprises irradiating a radical polymerization initiator according to claim 1 with light.