Curable composition, polymer functional cured product, water-soluble acrylamide compound, and method for manufacturing same

Patent metadata

Field	Value
Publication number	US-10087263-B2
Application number	US-201615252859-A
Country	US
Kind code	B2
Filing date	Aug 31, 2016
Priority date	Mar 12, 2014
Publication date	Oct 2, 2018
Grant date	Oct 2, 2018

Abstract

There is provided a curable composition including a water-soluble acrylamide monomer represented by the following General Formula (1-1) or (1-2), a polymer functional cured product, a water-soluble acrylamide compound, and a method for manufacturing the same.

In General Formulas (1-1) and (1-2), m represents an integer of 2 or greater, and L represents an m-valent group or a single bond. Here, in a case where L is a single bond, m is 2. L 1 and L 2 each represent a single bond or a divalent linking group. R 1 to R 5 each represent a hydrogen atom or a substituent, and may be bonded to each other to form a ring, and may be bonded to L, L 1 , or L 2 to form a ring. Either one of R A and R B represents a group represented by General Formula (a), and the other represents a group represented by General Formula (b).

First claim

What is claimed is:

1. A curable composition, comprising:
a water-soluble multi-acrylamide-containing monomer represented by the following General Formula (1-1) or (1-2),

in General Formulas (1-1) and (1-2), m represents an integer of 2 or greater, and L represents an m-valent group or a single bond; here, in a case where L is a single bond, m is 2; L 1 and L 2 each independently represent a single bond or a divalent linking group; R 1 to R 5 each independently represent a hydrogen atom or a substituent, and may be bonded to each other to form a ring, and may be bonded to L, L 1 , or L 2 to form a ring; at least one but not all of R A and R B represents a group represented by the following General Formula (a), and the other represents a group represented by the following General Formula (b); and here, m —[C(R 3 )(R B )—C(R 1 )(R 2 )(R A )]'s may be the same as or different from each other, m -[L 2 -C(R 3 )(R B )—C(R 2 )(R A )-L 1 ]-'s may be the same as or different from each other, and in m—[C(R 3 )(R B )—C(R 1 )(R 2 )(R A )]'s or m—[L 2 -C(R 3 )(R B )—C(R 2 )(R A )-L 1 ]-'s, R A or R B may be substituted with the group represented by the following General Formula (a); and

in General Formula (a), M A represents a hydrogen ion, an inorganic ion, or an organic ion; here, each of the inorganic ion and the organic ion may be a di- or higher valent ion; and in General Formula (b), R b represents a hydrogen atom or an alkyl group.

2. The curable composition according to claim 1 ,
wherein m is 2, and L is a single bond, an alkylene group, or an arylene group.

3. The curable composition according to claim 2 ,
wherein the water-soluble multi-acrylamide-containing monomer represented by General Formula (1-1) is represented by the following General Formula (2), and

in General Formula (2), M C and M D each independently represent a hydrogen ion, an inorganic ion, or an organic ion; and here, each of the inorganic ion and the organic ion may be a di- or higher valent ion.

4. A polymer functional cured product which is formed by polymerizing and curing the curable composition according to claim 1 .

5. The polymer functional cured product according to claim 4 ,
wherein the polymer functional cured product is an ion-exchange membrane, a proton conductive membrane, a reverse osmosis membrane, a forward osmosis membrane, a polymer electrolyte, or a water-absorbing resin.

6. A polymer functional cured product, comprising:
a polymer having a structural unit represented by the following General Formula (I-1) or (I-2),

in General Formulas (I-1) and (I-2), m represents an integer of 2 or greater, and L represents an m-valent group or a single bond; here, in a case where L is a single bond, m is 2;L 1 and L 2 each independently represent a single bond or a divalent linking group; R 1 to R 5 each independently represent a hydrogen atom or a substituent, and may be bonded to each other to form a ring, and may be bonded to L, L 1 , or L 2 to form a ring; at least one but not all of R C and R D represents a group represented by the following General Formula (a), and the other represents a group represented by the following General Formula (c); and here, m —[C(R 3 )(R D )—C(R 1 )(R 2 )(R C )]'s may be the same as or different from each other, m -[L 2 -C(R 3 )(R D )—C(R 2 )(R C )-L 1 ]-'s may be the same as or different from each other, and in m —[C(R 3 )(R D )—C(R 1 )(R 2 )(R C )]'s or m -[L 2 -C(R 3 )(R D )—C(R 2 )(R C )-L 1 ]-'s, R C or R D may be substituted with the group represented by the following General Formula (a); and

in General Formula (a), M A represents a hydrogen ion, an inorganic ion, or an organic ion; here, each of the inorganic ion and the organic ion may be a di- or higher valent ion; and in General Formula (c), R b represents a hydrogen atom or an alkyl group.

7. The polymer functional cured product according to claim 6 ,
wherein m is 2, and L is a single bond, an alkylene group, or an arylene group.

8. The polymer functional cured product according to claim 7 ,
wherein the structural unit represented by General Formula (I-1) is a structural unit represented by the following General Formula (II), and

in General Formula (II), M C and M D each independently represent a hydrogen ion, an inorganic ion, or an organic ion; and here, each of the inorganic ion and the organic ion may be a di- or higher valent ion.

9. A water-soluble multi-acrylamide-containing compound represented by the following General Formula (1-1) or (1-2),

in General Formulas (1-1) and (1-2), m represents an integer of 2 or greater, and L represents an m-valent group or a single bond; here, in a case where L is a single bond, m is 2;L 1 and L 2 each independently represent a single bond or a divalent linking group; R 1 to R 5 each independently represent a hydrogen atom or a substituent, and may be bonded to each other to form a ring, and may be bonded to L, L 1 , or L 2 to form a ring; at least one but not all of R A and R B represents a group represented by the following General Formula (a), and the other represents a group represented by the following General Formula (b); and here, m —[C(R 3 )(R B )—C(R 1 )(R 2 )(R A )]'s may be the same as or different from each other, m -[L 2 -C(R 3 )(R B )—C(R 2 )(R A )-L 1 ]-'s may be the same as or different from each other, and in m —[C(R 3 )(R B )—C(R 1 )(R 2 )(R A )]'s or m -[L 2 -C(R 3 )(R B )—C(R 2 )(R A )-L 1 ]-'s, R A or R B may be substituted with the group represented by the following General Formula (a); and

in General Formula (a), M A represents a hydrogen ion, an inorganic ion, or an organic ion; here, each of the inorganic ion and the organic ion may be a di- or higher valent ion; and in General Formula (b), R b represents a hydrogen atom or an alkyl group.

10. The water-soluble multi-acrylamide-containing compound according to claim 9 ,
wherein m is 2, and L is a single bond, an alkylene group, or an arylene group.

11. The water-soluble acrylamide compound according to claim 10 ,
wherein the water-soluble multi-acrylamide-containing compound represented by General Formula (1-1) is represented by the following General Formula (2), and

in General Formula (2), M C and M D each independently represent a hydrogen ion, an inorganic ion, or an organic ion; and here, each of the inorganic ion and the organic ion may be a di- or higher valent ion.

12. A method for manufacturing the water-soluble multi-acrylamide-containing compound according to claim 9 ,
wherein an olefin compound represented by the following General Formula (3-1) or (3-2), acrylonitrile, and fuming sulfuric acid are reacted, and

Assignees

• Fujifilm Corp

Inventors

• Kodama Keisuke
• Kaminaga Kuniyuki

Classifications

• C08J2333/24

  Homopolymers or copolymers of amides or imides · CPC title

• C08F20/58 Primary

  containing oxygen in addition to the carbonamido oxygen {, e.g. N-methylolacrylamide, N-acryloylmorpholine} · CPC title

• B01D61/42

  Electrodialysis; Electro-osmosis {; Electro-ultrafiltration; Membrane capacitive deionization} · CPC title

• B01D2325/14

  Membrane materials having negatively charged functional groups · CPC title

• Y02P70/56

  Cross-Sectional Technologies · mapped topic