# US 11,028,198 B2 · Tetrafluoroethylene and perfluorinated allyl ether copolymers

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- Number: US 11,028,198 B2
- Document ID: US11028198B2
- Status: Granted
- Kind: B2
- Application number: 16/325,831
- Filed: 2017-08-01
- Published: 2019-07-04
- Granted: 2021-06-08
- Earliest claimed: 2016-08-17
- Assignees: 3M Innovative Properties Company
- Applicants: 3M Innovative Properties Company
- Inventors: Harald Kaspar; Klaus Hintzer; Markus E. Hirschberg; Herbert Koenigsmann; Karl D. Weilandt; Tilman C. Zipplies
- Web page: https://patentgrep.com/patent/US11028198B2

## CPC

- C08F 214/26: Tetrafluoroethene
- C08F 214/28: Hexyfluoropropene
- C08L 27/18: Homopolymers or copolymers or tetrafluoroethene
- C08L 27/20: Homopolymers or copolymers of hexafluoropropene
- H01B 3/445: {from vinylfluorides or other fluoroethylenic compounds}
- C08F 214/182: {Monomers containing fluorine not covered by the groups C08F214/20 - C08F214/28}
- C08L 2203/16: used for films
- C08L 2203/18: used for pipes
- C08F: MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08L: COMPOSITIONS OF MACROMOLECULAR COMPOUNDS (compositions based on polymerisable monomers C08F, C08G; artificial filaments or fibres D01F; textile treating compositions D06)
- 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 and second polymerized monomer units in a range from 0.2 to 1 percent by weight, based on the total weight 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 independently from 1 to 6, and z is 0, 1, or 2. The copolymer has a melt flow index in a range from 0.02 grams per 10 minutes to 19.4 grams per 10 minutes. 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
at least 66% by weight based on the total weight of the copolymer of tetrafluoroethylene units;
units independently represented by formula
in a range from 0.2 to 12% by weight, based on the total weight of the copolymer, wherein n is independently from 1 to 6, z is 0, 1, or 2, 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;
from 5 to 22% by weight based on the total weight of the copolymer of units derived from hexafluoropropylene; and
units represented by formula
wherein a is 0 or 1, each b is independently from 1 to 4, c is 0 to 4, d is 0 or 1, e is 1 to 6, and X is independently —F, —NH2, —OH, or —OZ, and wherein Z is independently a metallic cation or a quaternary ammonium cation,
wherein the copolymer has a melt flow index in a range from 1 to 19 grams per 10 minutes; and
wherein the copolymer has up to 200 —SO2X groups per 106 carbon atoms and up to 100 unstable end groups per 106 carbon atoms, wherein X is independently —F, —NH2, —OH, or —OZ, wherein Z is independently a metallic cation or a quaternary ammonium cation, wherein the unstable end groups are selected from —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 2 (depends on 1)

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

### Claim 3 (depends on 1)

The copolymer of claim 1, wherein z is 1 or 2.

### Claim 4 (depends on 1)

The copolymer of claim 1, wherein z is 0.

### Claim 5 (depends on 1)

The copolymer of claim 1, comprising the units independently represented by formula
in a range from 0.02 to 1.9 mole percent based on the total amount of the copolymer.

### Claim 6 (depends on 1)

The copolymer of claim 1, further comprising units derived from at least one perfluorinated terminal olefin independently having from 4 to 8 carbon atoms.

### Claim 7 (depends on 1)

The copolymer of claim 1, wherein the —SO2X groups comprise —SO2X end groups.

### Claim 8 (depends on 1)

The copolymer of claim 1, wherein
(i) the copolymer comprises 10 percent to 17 percent by weight, based on the total weight of the copolymer of the units derived from hexafluoropropylene and
(ii) the copolymer has a melting point in a range from 220° C. to 285° C.

### Claim 9 (depends on 1)

The copolymer of claim 1, being provided as an aqueous dispersion comprising the copolymer.

### Claim 10 (depends on 1)

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

### Claim 11 (depends on 10)

The method of claim 10, wherein the extruded article comprises at least one of a film, tube, pipe, or hose.

### Claim 12 (depends on 10)

The method of claim 10, wherein the extruded article is a conductor having the copolymer extruded thereon.

### Claim 13 (depends on 1)

An extruded article comprising the copolymer of claim 1.

### Claim 14 (depends on 13)

The extruded article of claim 13, wherein the extruded article comprises at least one of a film, tube, pipe, or hose.

### Claim 15 (depends on 13)

The extruded article of claim 13, wherein the extruded article is a conductor having the copolymer extruded thereon.

### Claim 16 (depends on 1)

A method of making the copolymer of claim 1, the method comprising copolymerizing components comprising tetrafluoroethylene; at least one compound independently represented by formula CF2═CFCF2(OCnF2n)ZORf, wherein n is independently from 1 to 6, z is 0, 1, or 2, 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; hexafluoropropylene; and a monomer resulting in units of