Monomer composition and method for producing fluorinated polymer

Patent metadata

Field	Value
Publication number	US-11274168-B2
Application number	US-201916282377-A
Country	US
Kind code	B2
Filing date	Feb 22, 2019
Priority date	Sep 28, 2016
Publication date	Mar 15, 2022
Grant date	Mar 15, 2022

Abstract

To provide a monomer composition in which the solubility of the polymerization inhibitor in the cyclic monomer is good, the stability of the cyclic monomer during storage is good, and the cyclic monomer and the polymerization inhibitor are easily separated by distillation; and a method for producing a high molecular weight fluorinated polymer from the monomer composition.A monomer composition which comprises a specific cyclic monomer and a polymerization inhibitor, wherein the polymerization inhibitor is a polymerization inhibitor which satisfies (a) it is a 6-membered unsaturated cyclic hydrocarbon having from 1 to 4 substituents, (b) it has, as the substituent, at least one type selected from the group consisting of a t-butyl group, a methyl group, an isopropenyl group, an oxo group and a hydroxy group, (c) in a case where it has an oxo group as one type of the substituent, it has, as the substituent other than the oxo group, either one or both of a t-butyl group and a methyl group, and (d) in a case where it has a hydroxy group as the substituent, the number of the hydroxy group is only one.

First claim

What is claimed is:

1. A monomer composition comprising a cyclic monomer and a polymerization inhibitor,
the cyclic monomer being at least one monomer selected from the group consisting of a compound represented by the following formula (m11), a compound represented by the following formula (m12), a compound represented by the following (m13-1), and a compound represented by the following formula (m13-2), and
the polymerization inhibitor being a polymerization inhibitor which satisfies the following requirements (a) to (d):
(a) it is a 6-membered unsaturated cyclic hydrocarbon having from 1 to 4 substituents,
(b) it has, as the substituent, at least one type selected from the group consisting of a t-butyl group, a methyl group, an isopropenyl group, an oxo group and a hydroxy group,
(c) in a case where it has an oxo group as one type of the substituent, it has, as the substituent other than the oxo group, either one or both of a t-butyl group and a methyl group, and
(d) in a case where it has a hydroxy group as the substituent, the number of the hydroxy group is only one;

wherein R 11 , R 12 , and R 14 are each independently a fluorine atom, a C 1-10 perfluoroalkyl group or a group having an etheric oxygen atom in a carbon-carbon bond of a C 2-10 perfluoroalkyl group, and R 13 is a single bond, a C 1-10 perfluoroalkylene group or a group having an etheric oxygen atom in a carbon-carbon bond of a C 2-10 perfluoroalkylene group.

2. The monomer composition according to claim 1 , wherein the proportion of the cyclic monomer is from 90 to 99.99 mass % based on the total amount of the monomer composition.

3. The monomer composition according to claim 1 , wherein the proportion of the polymerization inhibitor is from 0.01 to 10 mass % based on the total amount of the monomer composition.

4. The monomer composition according to claim 1 , wherein the cyclic monomer is the compound represented by the formula (m11) or the compound represented by the formula (m12).

5. The monomer composition according to claim 1 , wherein the cyclic monomer is at least the compound represented by the formula (m11) and the compound represented by the formula (m11) is a compound represented by the following formula (m11-1), a compound represented by the following formula (m11-2) or a compound represented by the following formula (m11-3):

6. The monomer composition according to claim 1 , wherein the cyclic monomer is at least the compound represented by the formula (m12) and the compound represented by the formula (m12) is a compound represented by the following formula (m12-1) or a compound represented by the following formula (m12-2):

7. The monomer composition according to claim 1 , wherein the cyclic monomer is at least the compound represented by the formula (m13-1).

8. The monomer composition according to claim 1 , wherein the polymerization inhibitor is at least one polymerization inhibitor selected from the group consisting of a compound represented by the following formula (i-1), a compound represented by the following formula (i-2), a compound represented by the following formula (i-3) and a compound represented by the following formula (i-4):

9. The monomer composition according to claim 8 , wherein the polymerization inhibitor is at least one polymerization inhibitor selected from the group consisting of the compound represented by the formula (i-1), the compound represented by the formula (i-2) and the compound represented by the formula (i-3).

10. A method for producing a fluorinated polymer, which comprises distilling the monomer composition as defined in claim 1 to separate the cyclic monomer, and polymerizing a monomer component containing the cyclic monomer.

11. The method for producing a fluorinated polymer according to claim 10 , wherein the monomer composition is distilled by simple distillation, simple distillation with packed column, or purification distillation.

12. The method for producing a fluorinated polymer according to claim 10 , wherein the fluorinated polymer is an electrolyte material to be contained in a polymer electrolyte membrane or a catalyst layer of a membrane/electrode assembly for a polymer electrolyte fuel cell.

13. The monomer composition according to claim 1 , wherein the cyclic monomer is at least the compound represented by the formula (m13-2).

Assignees

• Agc Inc

Inventors

• Saito Susumu
• Hashimoto Wakako

Classifications

• C08F216/1475

  Monomers containing sulfur and oxygen · CPC title

• H01M8/1027

  having carbon, oxygen and other atoms, e.g. sulfonated polyethersulfones [S-PES] · CPC title

• C08F34/02 Primary

  in a ring containing oxygen (coumarone-indene polymers C08F244/00) · CPC title

• Y02E60/50

  Fuel cells · CPC title

• H01M8/1069

  characterised by the manufacturing processes · CPC title