# US 11,306,167 B2 · Fluorinated elastic copolymer, and method for producing fluorinated elastic copolymer

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- Number: US 11,306,167 B2
- Document ID: US11306167B2
- Status: Granted
- Kind: B2
- Application number: 16/861,276
- Filed: 2020-04-29
- Published: 2020-08-13
- Granted: 2022-04-19
- Earliest claimed: 2017-12-06
- Assignees: AGC Inc.
- Applicants: AGC Inc.
- Inventors: Satoko Yasuda; Keisuke Yagi; Takehiro Kose; Yukiko Hattori; Toshikazu Yoneda
- Web page: https://patentgrep.com/patent/US11306167B2

## CPC

- C08F 214/265: {with non-fluorinated comonomers}
- C08F 214/28: Hexyfluoropropene
- C08F 14/26: Tetrafluoroethene
- C08F 214/22: Vinylidene fluoride
- C08F 214/26: Tetrafluoroethene
- C08F 220/06: Acrylic acid; Methacrylic acid; Metal salts or ammonium salts thereof
- C08F 283/00: Macromolecular compounds obtained by polymerising monomers on to polymers provided for in subclass C08G
- C08F 214/222: {with fluorinated vinyl ethers}
- C08F 214/262: {with fluorinated vinyl ethers}
- C08F 214/282: {with fluorinated vinyl ethers}
- C08F: MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS

## Abstract

To provide a fluorinated elastic copolymer excellent in adhesion, processability, mechanical properties, heat resistance and chemical resistance. A fluorinated elastic copolymer having units based on a monomer (a), units based on a monomer (b) and optionally units based on a monomer (c), which has an iodine atom bonded to a terminal of a molecular chain and the unit based on the monomer (b) adjacent to the iodine atom, and which has a proportion of the units based on the monomer (b) of from 0.09 to 2.0 mol % to all units. Monomer (a): monomer selected from the group consisting of tetrafluoroethylene, hexafluoropropylene, vinylidene fluoride, chlorotrifluoroethylene, a perfluoro(alkyl vinyl ether) and 2,3,3,3-tetrafluoropropene; monomer (b): a monomer having at least one type of functional group selected from the group consisting of an epoxy group, a hydroxy group, a carbonyl group-containing group and an isocyanate group; monomer (c): a monomer selected from the group consisting of ethylene and propylene.

## Claims

### Claim 1

A fluorinated elastic copolymer having units based on the following monomer (a), units based on the following monomer (b) and optionally units based on the following monomer (c),
which has an iodine atom bonded to a terminal of a molecular chain of the fluorinated elastic copolymer, and the unit based on the monomer (b) adjacent to the iodine atom, and
which has a proportion of the units based on the monomer (b) of from 0.09 to 2.0 mol % to all units of the fluorinated elastic copolymer:
monomer (a): a monomer selected from the group consisting of tetrafluoroethylene, hexafluoropropylene, vinylidene fluoride, chlorotrifluoroethylene, a perfluoro(alkyl vinyl ether) and 2,3,3,3-tetrafluoropropene;
monomer (b): a monomer having at least one adhesive functional group selected from the group consisting of an epoxy group and a hydroxy group, and having one polymerizable carbon-carbon double bond;
monomer (c): a monomer selected from the group consisting of ethylene and propylene.

### Claim 2 (depends on 1)

The fluorinated elastic copolymer according to claim 1, which is a copolymer selected from the group consisting of a copolymer having units based on tetrafluoroethylene, units based on propylene and units based on the monomer (b), a copolymer having units based on tetrafluoroethylene, units based on a perfluoro(alkyl vinyl ether) and units based on the monomer (b), a copolymer having units based on vinylidene fluoride, units based on hexafluoropropylene and units based on the monomer (b), a copolymer having units based on tetrafluoroethylene, units based on vinylidene fluoride, units based on hexafluoropropylene and units based on the monomer (b), and a copolymer having units based on vinylidene fluoride, units based on tetrafluoroethylene, units based on a perfluoro(alkyl vinyl ether) and units based on the monomer (b).

### Claim 3 (depends on 1)

The fluorinated elastic copolymer according to claim 1, wherein the monomer (b) is a monomer selected from the group consisting of allyl glycidyl ether, vinyl glycidyl ether, 4-glycidyl oxybutyl vinyl ether and 4-hydroxybutyl vinyl ether.

### Claim 4 (depends on 1)

The fluorinated elastic copolymer according to claim 1, wherein a proportion of the units based on the monomer (a) is from 30 to 98 mol % to the total amount of all units of the fluorinated elastic copolymer.

### Claim 5 (depends on 1)

The fluorinated elastic copolymer according to claim 1, which has the units based on the monomer (c).

### Claim 6 (depends on 5)

The fluorinated elastic copolymer according to claim 5, wherein the total proportion of the units based on the monomer (a) and the units based on the monomer (c) is from 50 to 99.91 mol % to the total amount of all units of the fluorinated elastic copolymer.

### Claim 7 (depends on 5)

The fluorinated elastic copolymer according to claim 5, wherein the proportion of the units based on the monomer (c) is from 1 to 70 mol % to the total amount of the units based on the monomer (a) and the units based on the monomer (c).

### Claim 8 (depends on 1)

The fluorinated elastic copolymer according to claim 1, which has a mass average molecular weight of from 10,000 to 2,000,000.

### Claim 9

A method for producing a fluorinated elastic copolymer having units based on the following monomer (a), units based on the following monomer (b) and optionally units based on the following monomer (c), which comprises
polymerizing a monomer component comprising the monomer (a) and optionally the monomer (c) and not including the monomer (b), in the presence of an iodine compound having two iodine atoms until units in an amount of at least 80 mol % to all units of the fluorinated elastic copolymer are formed, and
copolymerizing monomer components comprising the monomer (a), the monomer (b) and optionally the monomer (c) until the units based on the monomer (b) in an amount of from 0.09 to 2.0 mol % to all units of the fluorinated elastic copolymer are formed:
monomer (a): a monomer selected from the group consisting of tetrafluoroethylene, hexafluoropropylene, vinylidene fluoride, chlorotrifluoroethylene, a perfluoro(alkyl vinyl ether) and 2,3,3,3-tetrafluoropropene;
monomer (b): a monomer having at least one adhesive functional group selected from the group consisting of an epoxy group and a hydroxy group, and having one polymerizable carbon-carbon double bond;
monomer (c): a monomer selected from the group consisting of ethylene and propylene.

### Claim 10 (depends on 9)

The production method according to claim 9, wherein the iodine compound is a compound represented by the following formula (1):
I—Rf1—I (1)
wherein Rf1 is a C4-12 perfluoroalkylene group.

### Claim 11 (depends on 9)

The production method according to claim 9, wherein the monomer (a) and optionally the monomer (c) are polymerized in the presence of an emulsifier.
