Highly fluorinated elastomers

Patent metadata

Field	Value
Publication number	US-9982091-B2
Application number	US-201515122538-A
Country	US
Kind code	B2
Filing date	Mar 3, 2015
Priority date	Mar 6, 2014
Publication date	May 29, 2018
Grant date	May 29, 2018

Abstract

Described herein is a peroxide curable, highly fluorinated elastomer derived from (a) a fluorinated di-iodo ether compound of the following formula I: Rf—CF(I)—(CX2)n—(CX2CXR)m—O—R″f-Ok—(CXR′CX2)p—(CX2)q—CF(I)—R′f wherein X is independently selected from F, H, and Cl; Rf and R′f are independently selected from F and a monovalent perfluoroalkane having 1-3 carbons; R is F, or a partially fluorinated or perfluorinated alkane comprising 1-3 carbons; R″f is a divalent fluoroalkylene having 1-5 carbons or a divalent fluorinated alkylene ether having 1-8 carbons and at least one ether linkage; k is 0 or 1; and n, m, and p are independently selected from an integer from 0-5, with the proviso that when k is 0, n+m is at least 1 and p+q is at least 1; and (b) a fluorinated monomer.

First claim

What is claimed is:

1. A composition comprising a highly fluorinated elastomer gum wherein the highly fluorinated elastomer gum is derived from
(a) a fluorinated di-iodo ether compound of the following formula I:
R f —CF(I)—(CX 2 ) n —(CX 2 CXR) m —O—R″ f —O k —(CXR′CX 2 ) p —(CX 2 ) q —CF(I)—R′ f

wherein
X is independently selected from F, H, and Cl;
R f and R′ f are independently selected from F and a monovalent perfluoroalkane having 1-3 carbons;
R is F, or a partially fluorinated or perfluorinated alkane comprising 1-3 carbons;
R″ f is a divalent fluoroalkylene having 1-5 carbons or a divalent fluorinated alkylene ether having 1-8 carbons and at least one ether linkage;
k is 0 or 1; and n, m, and p are independently selected from an integer from 0-5, with the proviso that when k is 0, n+m is at least 1 and p+q is at least 1; and

(b) a fluorinated monomer wherein the fluorinated monomer is selected from at least one of vinylidene fluoride, tetrafluoroethylene, hexafluoropropylene, a fluorinated allyl ether, a fluorinated vinyl ether, and combinations thereof.

2. The composition of claim 1 , wherein the fluorinated di-iodo ether compound of formula I comprises less than 1% by weight hydrogen.

3. The composition of claim 1 , wherein the fluorinated di-iodo ether compound is perfluorinated.

4. The composition of claim 1 , wherein the highly fluorinated elastomer gum is derived from 0.1-1 wt % of the fluorinated di-iodo ether compound of formula I.

5. The composition of claim 1 , wherein the fluorinated vinyl ether is selected from at least one of a perfluoro (methyl vinyl) ether (PMVE), perfluoro (ethyl vinyl) ether (PEVE), perfluoro (n-propyl vinyl) ether (PPVE-1), perfluoro-2-propoxypropylvinyl ether (PPVE-2), perfluoro-3-methoxy-n-propylvinyl ether, perfluoro-2-methoxy-ethylvinyl ether, and CF 3 —(CF 2 ) 2 —O—CF(CF 3 )—CF 2 —O—CF(CF 3 )—CF 2 —O—CF═CF 2 , and combinations thereof.

6. The composition of claim 1 , wherein the fluorinated allyl ether is selected from at least one of a perfluoro (methyl allyl) ether, perfluoro (ethyl allyl) ether, perfluoro (n-propyl allyl) ether, perfluoro-2-propoxypropylallyl ether, perfluoro-3-methoxy-n-propylallyl ether, perfluoro-2-methoxy-ethylallyl ether, and CF 3 —(CF 2 ) 2 —O—CF(CF 3 )—CF 2 —O—CF(CF 3 )—CF 2 —O—CF 2 CF═CF 2 and combinations thereof.

7. The composition of claim 1 , further comprising a non-fluorinated monomer.

8. The composition of claim 7 , wherein the non-fluorinated monomer is ethylene, propylene, or combinations thereof.

9. The composition of claim 1 , further comprising a cure site monomer, wherein the cure site monomer comprises at least one of (a) a Br, (b) a I, (c) a nitrile endgroup, and (d) two carbon-carbon double bonds.

10. A cured fluoroelastomer composition comprising the reaction product of a curing reaction of the composition according to claim 1 and a peroxide cure system.

11. A shaped article comprising the cured highly fluorinated elastomer according claim 10 .

12. The shaped article of claim 11 , selected from at least one of a hose, a tube, and an O-ring.

13. The composition of claim 1 , wherein the highly fluorinated elastomer gum is derived from at most 5% by weight of the fluorinated di-iodo ether compound relative to the total weight of monomers.

14. The composition of claim 1 , wherein the highly fluorinated elastomer gum is derived from at most 3% by weight of the fluorinated di-iodo ether compound relative to the total weight of monomers.

15. The composition of claim 1 , wherein the highly fluorinated elastomer gum is derived from at most 1% by weight of the fluorinated di-iodo ether compound relative to the total weight of monomers.

16. The composition of claim 1 , wherein the highly fluorinated elastomer gum is derived from a free radical polymerization.

Assignees

• 3M Innovative Properties Co

Inventors

• Hintzer Klaus
• Jochum Florian D
• Kaspar Harald
• Lochhaas Kai H
• Zipplies Tilman C
• Fukushi Tatsuo

Classifications

• C08L23/28

  by reaction with halogens or halogen-containing compounds (C08L23/32 takes precedence) · CPC title

• C08K5/06

  Ethers; Acetals; Ketals; Ortho-esters · CPC title

• C08G65/007 Primary

  containing fluorine · CPC title

• C08F214/262 Primary

  with fluorinated vinyl ethers · CPC title

• C08F214/18

  Monomers containing fluorine · CPC title