Fluorine-containing diene compound, fluorine-containing polymer, and methods for producing same

Patent metadata

Field	Value
Publication number	US-11518832-B2
Application number	US-202016908872-A
Country	US
Kind code	B2
Filing date	Jun 23, 2020
Priority date	Dec 26, 2017
Publication date	Dec 6, 2022
Grant date	Dec 6, 2022

Abstract

The present invention relates to a fluorine-containing diene compound represented by the following formula I, and to a polymer thereof. In the formula, each of R1 to R7 is independently a hydrogen atom, a chlorine atom, a fluorine atom, or an alkyl group having a carbon number of 1 to 5 which may be substituted by a fluorine atom, k is 0 or 1, and at least one of R1 to R7 is a hydrogen atom.

First claim

The invention claimed is:

1. A fluorine-containing diene compound represented by the following formula I:

wherein in the formula, each of R 1 to R 3 , R 6 , and R 7 is independently a hydrogen atom, a chlorine atom, a fluorine atom, or an alkyl group having a carbon number of 1 to 5 which may be substituted by a fluorine atom, each of R 4 and R 5 is independently a hydrogen atom, a chloride atom, or an alkyl group having a carbon number of 1 to 5 which may be substituted by a fluorine atom, k is 0 or 1, and at least one of R 1 to R 7 is a hydrogen atom.

2. The fluorine-containing diene compound according to claim 1 , wherein in the formula I, each of R 1 and R 2 is independently a hydrogen atom or a fluorine atom, R 3 is a hydrogen atom, a chlorine atom, a fluorine atom, a methyl group, or a trifluoromethyl group, and each of R 4 and R 5 is independently a hydrogen atom, a methyl group, or a trifluoromethyl group.

3. A method for producing a fluorine-containing diene compound represented by the following formula I, the method comprising reacting a compound represented by the following formula a with a compound represented by the following formula b in the presence of a base:

wherein in the formulae, each of R 1 to R 7 is independently a hydrogen atom, a chlorine atom, a fluorine atom, or an alkyl group having a carbon number of 1 to 5 which may be substituted by a fluorine atom, k is 0 or 1, and at least one of R 1 to R 7 is a hydrogen atom.

4. The method for producing a fluorine-containing diene compound according to claim 3 , wherein the reaction is performed in the presence of a solvent.

5. The method for producing a fluorine-containing diene compound according to claim 3 , wherein the base is an aliphatic tertiary amine.

6. The method for producing a fluorine-containing diene compound according to claim 4 , wherein the solvent contains at least one of glyme and nitrile.

7. A fluorine-containing polymer obtained by polymerizing a fluorine-containing compound represented by the following formula I′ as a raw material monomer:

wherein in the formula, each of R 11 to R 13 , R 16 , and R 17 is independently a hydrogen atom, a chlorine atom, a fluorine atom, or a monovalent organic group which may have a heteroatom, each of R 14 and E 15 is independently a hydrogen atom, a chlorine atom, or a monovalent organic group which may have a heteroatom, k is 0 or 1, at least one of R 11 to R 17 is a hydrogen atom, R 11 or R 12 may combine with any one of R 13 to R 17 to form a ring, and R 13 may combine with any one of R 11 , R 12 and R 14 to R 17 to form a ring.

8. The fluorine-containing polymer according to claim 7 , wherein the fluorine-containing compound represented by the formula I′ is a fluorine-containing diene compound represented by the following formula I:

wherein in the formula, each of R 1 to R 3 , R 6 , and R 7 is independently a hydrogen atom, a chlorine atom, a fluorine atom, or an alkyl group having a carbon number of 1 to 5 which may be substituted by a fluorine atom, each of R 4 and R 5 is independently a hydrogen atom, a chlorine atom, or an alkyl group having a carbon number of 1 to 5 which may be substituted by a fluorine atom, k is 0 or 1, and at least one of R 1 to R 7 is a hydrogen atom.

9. The fluorine-containing polymer according to claim 8 , wherein in formula I, each of R 1 and R 2 is independently a hydrogen atom or a fluorine atom, R 3 is a hydrogen atom, a chlorine atom, a fluorine atom, a methyl group, or a trifluoromethyl group, and each of R 4 and R 5 is independently a hydrogen atom, a methyl group, or a trifluoromethyl group.

10. A method for producing a fluorine-containing polymer, the method comprising polymerizing a raw material monomer containing a fluorine-containing compound represented by the following formula I′:

wherein in the formula, each of R 11 to R 13 , R 16 , and R 17 is independently a hydrogen atom, a chlorine atom, a fluorine atom, or a monovalent organic group which may have a heteroatom, each of R 14 and R 12 is independently a hydrogen atom, a chloride atom, or a monovalent organic group which may have a heteroatom, k is 0 or 1, at least one of R 11 to R 17 is a hydrogen atom, R 11 or R 12 may combine with any one of R 13 to R 17 to form a ring, and R 13 may combine with any one of R 11 , R 12 and R 14 to R 17 to form a ring.

11. The method for producing a fluorine-containing polymer according to claim 10 , wherein the fluorine-containing compound represented by formula I′ is a fluorine-containing diene compound represented by the following formula I:

wherein in the formula, each of R 1 to R 3 , R 6 , and R 7 is independently a hydrogen atom, a chlorine atom, a fluorine atom, or an alkyl group having a carbon number of 1 to 5 which may be substituted by a fluorine atom, each of R 4 and R 5 is independently a hydrogen atom, a chlorine atom, or an alkyl group having a carbon number of 1 to 5 which may be substituted by a fluorine atom, k is 0 or 1, and at least one of R 1 to R 7 is a hydrogen atom.

12. The method for producing a fluorine-containing polymer according to claim 11 , wherein in formula I, each of R 1 and R 2 is independently a hydrogen atom or a fluorine atom, R 3 is a hydrogen atom, a chlorine atom, a fluorine atom, a methyl group, or a trifluoromethyl group, and each of R 4 and R 5 is independently a hydrogen atom, a methyl group, or a trifluoromethyl group.

Assignees

• Agc Inc

Inventors

• Watakabe Atsushi

Classifications

• C08F214/20 Primary

  Vinyl fluoride · CPC title

• C08F2/06

  Organic solvent · CPC title

• C08F236/20

  unconjugated · CPC title

• C07C43/17

  containing halogen · CPC title

• C07C41/16 Primary

  by reaction of esters of mineral or organic acids with hydroxy or O-metal groups · CPC title