Method for producing fluorine-containing polymer and composition thereof

Patent metadata

Field	Value
Publication number	US-12286513-B2
Application number	US-202217733247-A
Country	US
Kind code	B2
Filing date	Apr 29, 2022
Priority date	Nov 1, 2019
Publication date	Apr 29, 2025
Grant date	Apr 29, 2025

Abstract

An object of the present disclosure is to provide a method for producing a fluorine-containing polymer and a composition containing the fluorine-containing polymer. The present disclosure provides a composition comprising (A) a fluorine-containing polymer comprising as a main component a structural unit containing a fluorine-containing aliphatic ring, and (B) an aprotic solvent, wherein the fluorine-containing aliphatic ring of the fluorine-containing polymer (A) contains one, two, or three etheric oxygen atoms as a ring-constituting atom; when the fluorine-containing aliphatic ring contains a plurality of etheric oxygen atoms, the etheric oxygen atoms are not adjacent to each other; and the fluorine-containing polymer (A) is present in an amount of 20 mass % or more based on the mass of the composition.

First claim

The invention claimed is:

1. A composition comprising:
(A) a fluorine-containing polymer comprising as a main component a structural unit represented by the following formula (A3):

wherein R 6 to R 9 each independently represent fluorine, C 1 -C 5 perfluoroalkyl, or C 1 -C 5 perfluoroalkoxy; and
(B) an aprotic solvent,
wherein the fluorine-containing polymer (A) is dissolved in the aprotic solvent (B) and the fluorine-containing polymer (A) dissolved in the aprotic solvent (B) is present in an amount of 20 mass % or more based on the mass of the composition.

2. The composition according to claim 1 , wherein the fluorine-containing polymer (A) dissolved in the aprotic solvent (B) is present in an amount of 20 mass % to 65 mass % based on the mass of the composition.

3. The composition according to claim 1 , wherein the fluorine-containing polymer (A) dissolved in the aprotic solvent (B) is present in an amount of greater than 20 mass % to 65 mass % based on the mass of the composition.

4. The composition according to claim 1 , wherein the aprotic solvent (B) is at least one solvent selected from the group consisting of a perfluoroaromatic compound, a perfluorotrialkylamine, a perfluoroalkane, a hydrofluorocarbon, a perfluorocyclic ether, a hydrofluoroether, and an olefin compound containing at least one chlorine atom.

5. The composition according to claim 1 , wherein the aprotic solvent (B) is a hydrofluoroether.

6. The composition according to claim 1 , wherein the aprotic solvent (B) has a global warming potential (GWP) of 400 or less.

7. The composition according to claim 1 , wherein the aprotic solvent (B) is at least one hydrofluoroether selected from the group consisting of
a compound represented by formula (B-1):
F(CF 2 ) p O(CH 2 ) q H (B-1),
wherein p is an integer of 1 to 6, and q is an integer of 1 to 4;
a compound represented by formula (B-2):
H(CF 2 ) p O(CF 2 ) q F (B-2),
wherein p and q are as defined above;
a compound represented by formula (B-3):
H(CF 2 ) p O(CH 2 ) q H (B-3),
wherein p and q are as defined above;
a compound represented by formula (B-4):
X(CF 2 )pCH 2 O(CF 2 ) q H (B-4),
wherein X represents fluorine or hydrogen, and p and q are as defined above;
(CF 3 ) 2 CHOCH 3 ;
(CF 3 ) 2 CFOCH 3 ;
CF 3 CHFCF 2 OCH 3 ; and
CF 3 CHFCF 2 OCF 3 .

8. The composition according to claim 1 , wherein the aprotic solvent (B) is a compound represented by formula (B-5):
R 21 —O—R 22 (B-5),
wherein R 21 is linear or branched propyl or butyl in which at least one hydrogen atom is replaced by fluorine, and R 22 is methyl or ethyl.

9. The composition according to claim 1 , wherein the structural unit represented by the formula (A3) is
a structural unit represented by the following formula (A3-1):

10. The composition according to claim 1 , wherein a proportion of the structural unit represented by the formula (A3) in the fluorine-containing polymer (A) is 80 mol % or more.

11. A method for producing a fluorine-containing polymer (A) comprising as a main component a structural unit represented by the following formula (A3):

wherein R 6 to R 9 each independently represent fluorine, C 1 -C 5 perfluoroalkyl, or C 1 -C 5 perfluoroalkoxy,
wherein the monomer comprises a monomer (M) corresponding to the structural unit contained as the main component in the fluorine-containing polymer (A);
the polymerization reaction is performed in an aprotic solvent (B);
the aprotic solvent (B) is a hydrofluoroether;
the polymerization initiator is at least one member selected from the group consisting of

a compound represented by formula (C1):

wherein R 31 and R 32 are the same or different, and each is perfluoropropyl, perfluoroisopropyl, perfluoro-2-phenyl-2-propyl, perfluorobutyl, perfluoro-sec-butyl, perfluoro-tert-butyl, perfluoropentyl, perfluoroisopentyl, perfluoroneopentyl, perfluoro-2-methyl-2-pentyl, perfluoro-2,4,4-trimethyl-2-pentyl, perfluorohexyl, perfluoro-2-methylhexyl, perfluoro-2-ethylhexyl, perfluorocyclohexyl, perfluoro-4-methylcyclohexyl, perfluoro-4-ethylcyclohexyl, perfluoroheptyl, perfluoro-2-heptyl, perfluoro-3-heptyl, perfluorooctyl, perfluoro-2-methyl-2-octyl, perfluorononyl, perfluorodecyl, perfluorophenyl, perfluoro-2-methylphenyl, perfluoro-3-methylphenyl, or perfluoro-4-methylphenyl, in which at least one fluorine atom is replaced by hydrogen;
a compound represented by formula (C2):

wherein R 33 and R 34 are the same or different, and each is a group in which at least one fluorine atom of C 3 -C 10 perfluoroalkyl optionally substituted with perfluorophenyl is replaced by hydrogen, or a group in which at least one fluorine atom of perfluorophenyl optionally substituted with linear or branched C 1 -C 4 perfluoroalkyl is replaced by hydrogen;
a compound represented by formula (C3):

wherein R 35 and R 36 are the same or different, and each is a group in which at least one fluorine atom of C 1 -C 10 perfluoroalkyl optionally substituted with perfluorophenyl is replaced by hydrogen, or a group in which at least one fluorine atom of perfluorophenyl optionally substituted with linear or branched C 1 -C 4 perfluoroalkyl is replaced by hydrogen; and
an inorganic peroxide; and
the polymer (A) is dissolved in the aprotic solvent (B), and the amount of the polymer (A) dissolved in the aprotic solvent (B) is 20 mass % or more based on the total mass of the polymer (A) and the aprotic solvent (B).

12. The production method according to claim 11 , wherein the polymerization initiator has a 10-hour half-life temperature of 0° C. to 160° C.; and the polymerization reaction is performed in the aprotic solvent (B) at a temperature that is not greater than 20° C. higher than a boiling point of the monomer (M) or a boiling point of the aprotic solvent, whichever is lower, and that is not greater than 20° C. higher than the 10-hour half-life temperature of the polymerization initiator.

13. The production method according to claim 11 , wherein the aprotic solvent (B) has a global warming potential (GWP) of 400 or less.

14. The production method according to claim 11 , wherein the aprotic solvent (B) is at least one hydrofluoroether selected from the group consisting of
a compound represented by formula (B-1):
F(CF 2 ) p O(CH 2 ) q H (B-1),
wherein p is an integer of 1 to 6, and q is an integer of 1 to 4;
a compound represented by formula (B-2):
H(CF 2 ) p O(CF 2 ) q F (B-2),
wherein p and q are as defined above;
a compound represented by formula (B-3):
H(CF 2 ) p O(CH 2 ) q H (B-3),
wherein p and q are as defined above;
a compound represented by formula (B-4):
X(CF 2 ) p CH 2 O(CF 2 ) q H (B-4),
wherein X represents fluorine or hydrogen, and p and q are as defined above;
(CF 3 ) 2 CHOCH 3 ;
(CF 3 ) 2 CFOCH 3 ;
CF 3 CHFCF 2 OCH 3 ; and
CF 3 CHFCF 2 OCF 3 .

15. The production method according to claim 11 , wherein the aprotic solvent (B) is a compound represented by formula

Assignees

• Daikin Ind Ltd

Inventors

• Suzuki Yuuki
• Matsuura Makoto
• Ogata Akitoshi
• Shirai Atsushi
• Okada Michiaki
• Ashida Shiomi
• Tanaka Yoshito
• Kishikawa Yosuke

Classifications

• C08F34/02

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

• C08J3/095

  Oxygen containing compounds · CPC title

• C08J3/093

  Halogenated hydrocarbons · CPC title

• C08F32/04

  having one carbon-to-carbon double bond · CPC title

• C09D145/00

  Coating compositions based on homopolymers or copolymers of compounds having no unsaturated aliphatic radicals in a side chain, and having one or more carbon-to-carbon double bonds in a carbocyclic or in a heterocyclic system; Coating compositions based on derivatives of such polymers (based on polymers of cyclic esters of polyfunctional acids C09D131/00; based on polymers of cyclic anhydrides or imides C09D135/00) · CPC title