Method of stabilizing perfluorodioxolane compound, perfluorodioxolane compound-containing composition and method of producing perfluorodioxolane compound polymer

Patent metadata

Field	Value
Publication number	US-11767308-B2
Application number	US-202017788901-A
Country	US
Kind code	B2
Filing date	Dec 25, 2020
Priority date	Dec 26, 2019
Publication date	Sep 26, 2023
Grant date	Sep 26, 2023

Abstract

Provided is a method of stabilizing a perfluorodioxolane compound, which includes having a quinone compound present in a composition containing a perfluorodioxolane compound, wherein the perfluorodioxolane compound is one or more perfluorodioxolane compounds selected from the group consisting of a perfluorodioxolane compound denoted by general formula (1) and a perfluorodioxolane compound denoted by general formula (2).

First claim

The invention claimed is:

1. A method of stabilizing a perfluorodioxolane, comprising:
having a quinone present in a composition including the perfluorodioxolane,
wherein the perfluorodioxolane comprises at least one selected from the group consisting of:
a compound of formula (1),

wherein Rf 1 and Rf 2 each independently denote a fluorine atom or a perfluoroalkyl group having 1 to 6 carbon atoms, an ether bond is optionally present in a carbon-carbon bond in the perfluoroalkyl group, and the Rf 1 and Rf 2 may optionally bond to each other to form a ring; and
a compound of formula (2),

wherein Rf 3 and Rf 4 each independently denote a fluorine atom or a perfluoroalkyl group having 1 to 6 carbon atoms, and an ether bond is optionally present in a carbon-carbon bond in the perfluoroalkyl group; and
the quinone comprises at least one selected from the group consisting of:
a compound of formula (3),

wherein R 1 to R 4 each independently denote a hydrogen atom, a fluorine atom or a chlorine atom; and
a compound of formula (4),

wherein R 5 to R 10 each independently denote a hydrogen atom, a fluorine atom or a chlorine atom.

2. The method according to claim 1 ,
wherein at least one of the R 1 to R 4 in the general formula (3) is a fluorine atom.

3. The method according to claim 1 ,
wherein the quinone comprises the compound of formula (3).

4. The method according to claim 1 ,
wherein the quinone comprises perfluoro-p-benzoquinone.

5. The method according to claim 1 ,
wherein at least one of the R 5 to R 10 in the formula (4) is a fluorine atom.

6. The method according to claim 1 ,
wherein the quinone is present at a weight ratio of 0.1 to 500 ppm relative to the perfluorodioxolane.

7. The method according to claim 6 , further comprising:
holding the composition, in which the quinone is present, in a container including a gas phase part including an inert gas.

8. The method according to claim 1 , further comprising:
holding the composition, in which the quinone is present, at a temperature of 0° C. or lower.

9. A composition, comprising:
a perfluorodioxolane; and
a quinone,
wherein the perfluorodioxolane comprises at least one selected from the group consisting of:
a compound of formula (1),

wherein Rf 1 and Rf 2 each independently denote a fluorine atom or a perfluoroalkyl group having 1 to 6 carbon atoms, an ether bond is optionally present in a carbon-carbon bond in the perfluoroalkyl group, and the Rf 1 and Rf 2 may optionally bond to each other in a ring; and
a compound of formula (2),

wherein Rf 3 and Rf 4 each independently denote a fluorine atom or a perfluoroalkyl group having 1 to 6 carbon atoms, and an ether bond is optionally present in a carbon-carbon bond in the perfluoroalkyl group; and
wherein the quinone comprises at least one selected from the group consisting of:
a compound of formula (3),

wherein R 1 to R 4 each independently denote a hydrogen atom, a fluorine atom or a chlorine atom; and
a compound of formula (4),

wherein R 5 to R 10 each independently denote a hydrogen atom, a fluorine atom or a chlorine atom.

10. The composition according to claim 9 ,
wherein the quinone is present at a weight ratio of 0.1 to 500 ppm relative to the perfluorodioxolane.

11. The composition according to claim 9 ,
wherein at least one of the R 1 to R 4 in the formula (3) is a fluorine atom.

12. The composition according to claim 9 ,
wherein the quinone comprises the compound of formula (3).

13. The composition according to claim 9 ,
wherein the quinone comprises perfluoro-p-benzoquinone.

14. The composition according to claim 9 ,
wherein at least one of the R 5 to R 10 in the formula (4) is a fluorine atom.

15. A method producing a perfluorodioxolane polymer, comprising:
adding a polymerization initiator to the composition of claim 9 , such that the perfluorodioxolane is polymerized.

16. The composition according to claim 9 , further comprising:
a perfluorodioxolane polymer at a content of 1.0 weight % or less after the composition is stored under filling of nitrogen for at least one week.

17. A method producing a perfluorodioxolane polymer, comprising:
adding a polymerization initiator to the composition of claim 16 , such that the perfluorodioxolane is polymerized.

18. The method according to claim 2 , wherein the quinone comprises perfluoro-p-benzoquinone.

19. The method according to claim 3 , wherein the quinone comprises perfluoro-p-benzoquinone.

20. The method according to claim 2 , wherein at least one of the R 5 to R 10 in the formula (4) is a fluorine atom.

Assignees

• Tosoh Corp
• Tosoh Finechem Corp

Inventors

• Inoue Daisuke
• Sesoko Yusuke
• Matsuo Hiroshi
• Takamiya Hiroki
• Mimura Hideyuki
• Shimono Tomoya
• NAGAI Tomonari

Classifications

• C07D317/42 Primary

  Halogen atoms or nitro radicals · CPC title

• C07C50/04

  Benzoquinones, i.e. C6H4O2 · CPC title

• C07C50/12

  Naphthoquinones, i.e. C10H6O2 · CPC title

• C07D317/44

  ortho- or peri-condensed with carbocyclic rings or ring systems · CPC title

• C08F234/02

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