Curable composition and cured polymer product

Patent metadata

Field	Value
Publication number	US-9795955-B2
Application number	US-201615238924-A
Country	US
Kind code	B2
Filing date	Aug 17, 2016
Priority date	Feb 21, 2014
Publication date	Oct 24, 2017
Grant date	Oct 24, 2017

Abstract

Provided are a curable composition including a compound expressed by General Formula (1) below; a polymerization initiator; and a chain transfer agent, and a cured polymer product.

In General Formula (1), m represents an integer of 1 to 4, and n represents an integer of 1 to 4. Here, a sum of m and n is not greater than 5. M A represents a hydrogen ion, an inorganic ion, or an organic ion. Here, an inorganic ion and an organic ion may be bivalent or higher ions. Each of R 1 and R 2 independently represents a hydrogen atom or an alkyl group.

First claim

What is claimed is:

1. A curable composition comprising:
a compound expressed by General Formula (1) below;
a polymerization initiator; and
a chain transfer agent,

wherein, in General Formula (1), m represents an integer of 1 to 4, n represents an integer of 1 to 4, a sum of m and n is not greater than 5, M A represents a hydrogen ion, an inorganic ion, or an organic ion, an inorganic ion and an organic ion are bivalent or higher ions, and each of R 1 and R 2 independently represents a hydrogen atom or an alkyl group.

2. The curable composition according to claim 1 ,
wherein the compound expressed by General Formula (1) is expressed by General Formula (2) below,

wherein, in General Formula (2), m represents an integer of 1 to 4, M A represents a hydrogen ion, an inorganic ion, or an organic ion, the inorganic ion and the organic ion may be bivalent or higher ions, and each of R 1 and R 2 independently represents a hydrogen atom or an alkyl group.

3. The curable composition according to claim 1 ,
wherein the polymerization initiator is selected from the group consisting of an alkylphenone compound, an acylphosphine oxide compound, and an oxime ester compound, and a chain transfer agent has a mercapto group.

4. The curable composition according to claim 1 ,
wherein the polymerization initiator is expressed by any one of General Formulae (PI-1) to (PI-3) below,

wherein in General Formulae (PI-1) to (PI-3), X P1 represents a hydroxy group or —N(R Pa )(R Pb ), each of R Pa and R Pb independently represents an alkyl group, R Pa and R Pb may be bonded to each other to form a ring, each of R P1 to R P3 independently represents a hydrogen atom, an alkyl group, an alkenyl group, an alkoxy group, an aryloxy group, or —N(R Pc )(R Pd ), each of R Pc and R Pd independently represents an alkyl group and are bonded to each other to form a ring, and R P2 and R P3 are bonded to each other to form a ring,
wherein R P4 represents an alkyl group, an aryl group, an alkylthio group, or an arylthio group, R P5 represents an alkyl group, an aryl group, an alkylthio group, an arylthio group, or an acyl group, and R P6 represents an alkyl group or an aryl group, and
wherein R P7 represents an alkyl group, an alkenyl group, or an aryl group, R P8 represents an alkyl group, an aryl group, or an acyl group, and R P9 represents an alkyl group or an aryl group.

5. The curable composition according to claim 1 ,
wherein the chain transfer agent is expressed by General Formula (CT) below,
H—Y-LL 1 -LL-LL 2 -S—H   General Formula (CT)

wherein in General Formula (CT), LL represents a single bond and a linking group selected from an alkylene group that may have a substituent, —O—, —S—, —N(R Ca )—, or a combination thereof, R Ca represents a hydrogen atom or a substituent, each of LL 1 and LL 2 independently represents —C(R C1 )(R C2 )—C(═O)O— in which an atom bonded to —[C(R C1 )(R C2 )]a- or LL is an oxygen atom, each of R C1 and R C2 independently represents a hydrogen atom or an alkyl group, a represents 1 or 2, and Y represents a sulfur atom or an oxygen atom.

6. The curable composition according to claim 1 ,
wherein 0.1 parts by mass to 10 parts by mass of the chain transfer agent is contained with respect to 1 part by mass of the polymerization initiator.

7. The curable composition according to claim 1 , further comprising:
a polymer binder.

8. The curable composition according to claim 7 ,
wherein the polymer binder is a monomer unit derived from an aliphatic hydrocarbon-based monomer, and
wherein, in a state in which a copolymer is formed, a copolymer of a monomer unit not having an unsaturated bond in the monomer unit and a monomer unit based on a styrene-based monomer is contained.

9. The curable composition according to claim 7 ,
wherein the polymer binder contains a copolymer of a monomer unit based acrylonitrile and a monomer unit not having an unsaturated bond derived from an aliphatic hydrocarbon-based monomer.

10. A cured polymer product obtained by polymerizing and curing the curable composition according to claim 1 .

11. The cured polymer product according to claim 10 , that is graft polymerized.

12. The cured polymer product according to claim 11 , obtained by polymerizing and curing by active radiation graft polymerization.

13. The cured polymer product according to claim 10 , at least comprising:
a polymer having a structural unit expressed by General Formula (I-1) below,

wherein, in General Formula (I-1), m represents an integer of 1 to 4, M A represents a hydrogen ion, an inorganic ion or an organic ion, an inorganic ion and an organic ion are bivalent or higher ions, and each of R 1 and R 2 independently represents a hydrogen atom or an alkyl group.

14. The cured polymer product according to claim 13 ,
wherein a content of a constitutional unit expressed by General Formula (I-1) above is 10 mass % or greater with respect to a total mass of the cured polymer product.

15. The cured polymer product according to claim 10 ,
wherein a content of the constitutional unit expressed by General Formula (A) below is 5 mass % or less with respect to a total mass of the cured polymer product,

wherein, in General Formula (A), each of R 5 and R 6 independently represents a hydrogen atom or an alkyl group.

16. The cured polymer product according to claim 10 ,
wherein an ion exchange capacity of the cured polymer product is 3.5 meq/g or greater.

17. The cured polymer product according to claim 10 ,
wherein the cured polymer product is selected from the group consisting of an ion exchange membrane, a proton conduction film, a reverse osmosis membrane, a forward osmosis membrane, a polymer electrolyte, and a water absorbing resin.

Assignees

• Fujifilm Corp

Inventors

• Inomata Sotaro
• Kodama Keisuke
• Inoue Kazuomi

Classifications

• B01D71/82

  characterised by the presence of specified groups, e.g. introduced by chemical after-treatment · CPC title

• B01J39/05

  in the strongly acidic form · CPC title

• B01D61/44

  Ion-selective electrodialysis · CPC title

• C08F12/30

  Sulfur · CPC title

• C08J5/2243

  obtained by introduction of active groups capable of ion-exchange into compounds of the type C08J5/2231 · CPC title