# US 10,766,990 B2 · Tetrafluoroethylene/hexafluoropropylene copolymers including perfluoroalkoxyalkyl pendant groups and methods of making and using the same

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- Number: US 10,766,990 B2
- Document ID: US10766990B2
- Status: Granted
- Kind: B2
- Application number: 15/550,321
- Filed: 2016-02-12
- Published: 2018-03-08
- Granted: 2020-09-08
- Earliest claimed: 2015-02-12
- Assignees: 3M Innovative Properties Company
- Applicants: 3M Innovative Properties Company
- Inventors: Denis Duchesne; Klaus Hintzer; Harald Kaspar; Kai H. Lochhaas; Per M. Nelson; Jens C. Schrooten; Karl D. Weilandt; Tilman C. Zipplies
- Web page: https://patentgrep.com/patent/US10766990B2

## CPC

- C08F 214/26: Tetrafluoroethene
- C08F 2/28: cationic
- C08F 214/262: {with fluorinated vinyl ethers}
- C08F 214/28: Hexyfluoropropene
- C08J 5/121: {by heating}
- C08K 3/08: Metals
- H01B 3/445: {from vinylfluorides or other fluoroethylenic compounds}
- C08F 2500/12: Melt flow index or melt flow ratio
- C08F 2800/10: as molar percentages
- C08K 2003/0818: {Alkali metal}
- C08F: MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08J: WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H (working, e.g. shaping, of plastics B29)
- C08K: Use of inorganic or non-macromolecular organic substances as compounding ingredients (paints, inks, varnishes, dyes, polishes, adhesives C09)
- H01B: CABLES; CONDUCTORS; INSULATORS; SELECTION OF MATERIALS FOR THEIR CONDUCTIVE, INSULATING OR DIELECTRIC PROPERTIES (selection for magnetic properties H01F1/00; waveguides H01P {; printed circuits H05K})

## Abstract

A copolymer having tetrafluoroethylene units, hexafluoropropylene units, and units independently represented by formula in a range from 0.02 to 2 mole percent, based on the total amount of the copolymer. Rf is a linear or branched perfluoroalkyl group having from 1 to 8 carbon atoms and optionally interrupted by one or more —O— groups, n is from 1 to 6, and m is 0 or 1. The copolymer has a melt flow index in a range from 25 grams per 10 minutes to 35 grams per 10 minutes and has up to 50 unstable end groups per 106 carbon atoms. The copolymer can be extruded to make articles, such as insulated cables. A method of making the copolymer is also disclosed.

## Claims

### Claim 1

A copolymer comprising tetrafluoroethylene units, hexafluoropropylene units, and units represented by formula
in a range from 0.02 to 2 mole percent, based on the total amount of the copolymer, wherein n is from 1 to 6, m is 0 or 1, and Rf is a linear or branched perfluoroalkyl group having from 1 to 8 carbon atoms and optionally interrupted by one or more —O— groups, wherein the copolymer has a melt flow index in a range from 25 grams per 10 minutes to 35 grams per 10 minutes measured at a temperature of 372° C. and at a support weight of 5.0 kg, and wherein the copolymer comprises at least 25 parts per million alkali-metal cations.

### Claim 2 (depends on 1)

The copolymer of claim 1, wherein the copolymer has not more than 50 unstable end groups per 106 carbon atoms.

### Claim 3 (depends on 1)

The copolymer of claim 1, wherein m is 0, wherein Rf is —CF3, and wherein n is 1 or 3.

### Claim 4 (depends on 2)

A copolymer of claim 2 wherein the unstable end groups are selected from the group consisting of —COOM, —CH2OH, —COF, and —CONH2, and wherein M is independently an alkyl group, a hydrogen atom, a metallic cation, or a quaternary ammonium cation.

### Claim 5 (depends on 4)

The copolymer of claim 4, wherein m is 0.

### Claim 6 (depends on 4)

The copolymer of claim 4, wherein Rf is —CF3, and wherein n is 1 or 3.

### Claim 7 (depends on 4)

The copolymer of claim 4, wherein the copolymer comprises at least 50 parts per million alkali-metal cations.

### Claim 8 (depends on 1)

The copolymer of claim 1, wherein the copolymer comprises at least 50 parts per million alkali-metal cations.

### Claim 9 (depends on 1)

The copolymer of claim 1, wherein the copolymer has a polydispersity of less than or equal to 2.

### Claim 10 (depends on 1)

The copolymer of claim 1, wherein the hexafluoropropylene units are present in the copolymer at 10 percent to 17 percent by weight, based on the total weight of the copolymer.

### Claim 11 (depends on 1)

The copolymer of claim 1 having a melting point in a range from 235° C. to 275° C.

### Claim 12 (depends on 1)

The copolymer of claim 1, further comprising units represented by formula
wherein Rf1 is a perfluoroalkyl group having from 1 to 8 carbon atoms.

### Claim 13 (depends on 1)

A method of making an extruded article, the method comprising extruding a melted composition comprising the copolymer of claim 1.

### Claim 14 (depends on 1)

An extruded article comprising the copolymer of claim 1.

### Claim 15 (depends on 14)

The extruded article of claim 14, wherein the extruded article comprises at least one of a film, tube, pipe, or hose.

### Claim 16 (depends on 14)

The extruded article of claim 14, wherein the extruded article is a conductor having the copolymer extruded thereon.

### Claim 17 (depends on 1)

A method of making the copolymer of claim 1, the method comprising copolymerizing components comprising tetrafluoroethylene, hexafluoropropylene, and at least one compound independently represented by formula CF2═CF(CF2)mO(CF2)nORf, wherein n is from 1 to 6, m is 0 or 1, and Rf is a perfluoroalkyl group having from 1 to 8 carbon atoms and optionally interrupted by one or more —O— groups.

### Claim 18 (depends on 17)

The method of claim 17, wherein copolymerizing is carried out by aqueous emulsion polymerization in the presence of a buffer including alkali-metal cations.

### Claim 19 (depends on 14)

The extruded article of claim 14, wherein the extruded article is not foamed.

### Claim 20 (depends on 14)

The extruded article of claim 14, wherein the extruded article is foamed.