Fumaric acid diester-cinnamic acid ester-based copolymer, production method thereof and film using the same

Patent metadata

Field	Value
Publication number	US-9512284-B2
Application number	US-201314647715-A
Country	US
Kind code	B2
Filing date	Nov 25, 2013
Priority date	Nov 28, 2012
Publication date	Dec 6, 2016
Grant date	Dec 6, 2016

Abstract

To provide a novel fumaric acid diester-cinnamic acid ester-based copolymer having a high molecular weight, which is expected to maintain excellent strength or ensures excellent toughness even when formed into a film, a method for efficiently producing the copolymer, and a film using the same. The fumaric acid diester-cinnamic acid ester-based copolymer contains a fumaric acid diester residue unit, a cinnamic acid ester residue unit having an alkyl group with a carbon number of 1 to 6, and a residue unit of a polyfunctional monomer having two or more radical polymerizable functional groups.

First claim

The invention claimed is:

1. A fumaric acid diester-cinnamic acid ester-based copolymer, comprising:
a fumaric acid diester residue unit;
a cinnamic acid ester residue unit having an alkyl group with a carbon number of 1 to 6; and
a residue unit of a polyfunctional monomer having two or more radical polymerizable functional groups.

2. The fumaric acid diester-cinnamic acid ester-based copolymer according to claim 1 , wherein the fumaric acid diester residue unit is a diethyl fumarate residue unit or a diisopropyl fumarate residue unit.

3. The fiimaric acid diester-cinnamic acid ester-based copolymer according to claim 1 , comprising:
from 50 to 98 mol % of the fumaric acid diester residue unit;
from 1 to 49 mol % of the cinnamic acid ester residue unit having an alkyl group with a carbon number of 1 to 6; and
from 0.01 to 1 mol % of the residue unit of the polyfunctional monomer having two or more radical polymerizable functional groups.

4. The fumaric acid diester-cinnamic acid ester-based copolymer according to claim 1 , comprising:
from 50 to 98.5 mol % of the diisopropyl fumarate residue unit;
from 1 to 49.5 mol % of the cinnamic acid ester residue unit having an alkyl group with a carbon number of 1 to 6; and
from 0.01 to 0.5 mol % of the residue unit of the polyfunctional monomer having two or more radical polymerizable functional groups.

5. The fumaric acid diester-cinnamic acid ester-based copolymer according to claim 1 , wherein the cinnamic acid ester residue unit is selected from the group consisting of a methyl cinnamate residue unit, an ethyl cinnamate residue unit and an isopropyl cinnamate residue unit.

6. The fumaric acid diester-cinnamic acid ester-based copolymer according to claim 1 , wherein the residue unit of the polyfunctional monomer having two or more radical polymerizable functional groups is an aromatic polyvinyl compound or a polyfunctional vinyl ether having two or more radical polymerizable functional groups.

7. The fumaric acid diester-cinnamic acid ester-based copolymer according to claim 1 ,
wherein
the fumaric acid diester residue unit is a diisopropyl fumarate residue unit, and
the residue unit of the polyfunctional monomer having two or more radical polymerizable functional groups is a residue unit of a polyfunctional acrylate having a urethane bond.

8. The fumaric acid diester-cinnamic acid ester-based copolymer according to claim 1 ,
wherein
the fumaric acid diester residue unit is a diisopropyl fumarate residue unit, and
the residue unit of the polyfunctional monomer having two or more radical polymerizable functional groups is a residue unit of a polyfunctional acrylate having an ester bond.

9. The fumaric acid diester-cinnamic acid ester-based copolymer according to claim 6 , wherein a number average molecular weight in terms of standard polystyrene is from 70,000 to 500,000.

10. The fumaric acid diester-cinnamic acid ester-based copolymer according to claim 8 , wherein a number average molecular weight in terms of standard polystyrene is from 60,000 to 500,000.

11. A method for producing a fumaric acid diester-cinnamic acid ester-based copolymer, comprising:
performing a radical polymerization reaction with a total of 100 mol % of monomers comprising from 50 to 98 mol % of a fumaric acid diester, from 1 to 49 mol % of a cinnamic acid ester having an alkyl group with a carbon number of 1 to 6, and from 0.01 to 1 mol % of a polyfunctional monomer having two or more radical polymerizable functional groups, in the presence of from 0.001 to 2 mol % of a radical polymerization initiator.

12. A method for producing a fumaric acid diester-cinnamic acid ester-based copolymer, comprising:
performing a radical polymerization reaction with a total of 100 mol % of monomers comprising from 50 to 98.5 mol % of diisopropyl fumarate, from 1 to 49.5 mol % of a cinnamic acid ester having an alkyl group with a carbon number of 1 to 6, and from 0.01 to 0.5 mol % of a polyfunctional acrylate having at least either one of a urethane bond and an ester bond, in the presence of from 0.001 to 2 mol % of a radical polymerization initiator.

13. A film, comprising the fumaric acid diester-cinnamic acid ester-based copolymer according to claim 6 .

Assignees

• Tosoh Corp

Inventors

• Kitagawa Takahiro
• Doi Tohru
• Fujii Yasuyoshi
• Sakaguchi Kota
• Inui Akira
• Ito Masayasu

Classifications

• C08J2333/06

  of esters containing only carbon, hydrogen, and oxygen, the oxygen atom being present only as part of the carboxyl radical · CPC title

• C08F265/04

  on to polymers of esters · CPC title

• C08J2333/08

  Homopolymers or copolymers of acrylic acid esters · CPC title

• C09D133/14

  of esters containing halogen, nitrogen, sulfur or oxygen atoms in addition to the carboxy oxygen · CPC title

• C08J5/18 Primary

  Manufacture of films or sheets · CPC title