Partially fluorinated compounds

Patent metadata

Field	Value
Publication number	US-9452960-B2
Application number	US-201314649666-A
Country	US
Kind code	B2
Filing date	Nov 27, 2013
Priority date	Dec 14, 2012
Publication date	Sep 27, 2016
Grant date	Sep 27, 2016

Abstract

Described herein is a composition comprising a partially fluorinated compound selected from the group consisting of: (a) I(CF 2 ) x CH 2 CF 2 I; (b) ICF 2 CH 2 (CF 2 ) x CH 2 CF 2 I; (c) I(CF 2 ) y CH═CF 2 ; (d) CF 2 ═CH(CF 2 ) y CH 2 CF 2 I; and (e) CF 2 ═CH(CF 2 ) y CH═CF 2 wherein x is an odd integer selected from 3 to 11, and y is an integer greater than 2, along with methods of making and polymerizing such compounds.

First claim

What is claimed is:

1. A composition comprising a partially fluorinated compound selected from the group consisting of:
(a) I(CF 2 ) x CH 2 CF 2 I;
(b) ICF 2 CH 2 (CF 2 ) x CH 2 CF 2 I;
(c) I(CF 2 ) y CH═CF 2 ;
(d) CF 2═ CH(CF 2 ) y CH 2 CF 2 I; and
(e) CF 2═ CH(CF 2 ) y CH═CF 2
wherein x is an odd integer selected from 3 to 11, and y is an odd integer selected from 3 to 11.

2. A polymer composition comprising the polymerized reaction product of the following reactants:
(a) a first compound selected from the partially fluorinated compound of claim 1 ; and
(b) a second compound comprising a fluorinated olefinic monomer.

3. The polymer composition of claim 2 , wherein the a second compound is selected from: hexafluoropropylene, trifluoroethylene, fluoroethylene, vinylidene fluoride, tetrafluoroethylene, perfluoro(methyl vinyl ether), perfluoro(propyl vinyl ether), perfluoro(methoxypropyl vinyl ether), perfluoro(ethoxymethyl vinyl ether), chlorotrifluoroethylene, and combinations thereof.

4. The polymer composition of claim 2 , wherein the reactants further include (c) a chain transfer agent, wherein the chain transfer agent is selected from the group consisting of: a C1 to C10 α,ω-diiodoperfluoroalkane; I(CF 2 )zCH 2 CH 2 I, wherein z is an integer greater than 2; CH 2 I 2; I(CF 2 ) z CH 2 CF 2 I wherein z is an integer greater than 2; and combinations thereof.

5. The polymer composition of claim 2 wherein at least one of x or y is 3.

6. An article comprising the cured polymer composition according to claim 2 .

7. A method of making a polymer comprising:
(a) providing a first fluorinated olefinic monomer comprising the partially fluorinated compound selected from at least one of I(CF 2 ) y CH═CF 2 and CF 2═ CH(CF 2 ) y CH═CF 2 wherein y is an integer greater than 2 of claim 1 ; a second fluorinated olefinic monomer; and an initiator; and
(b) polymerizing the first and second fluorinated olefinic monomers in the presence of the initiator to form a polymer.

8. The polymer composition of claim 4 , wherein the chain transfer agent is 1,3-diiodoperfluoropropane or 1,4-diiodoperfluorobutane.

9. The polymer composition of claim 2 , wherein the reactants further include (d) a non-fluorinated olefinic monomer.

10. The polymer composition of claim 2 , wherein the polymer composition comprises 0.05 to 1% by weight of iodine.

11. The method of claim 7 , further comprising polymerizing in the presence of a chain transfer agent.

12. The method of claim 11 , wherein the chain transfer agent is 1,3-diiodoperfluoropropane or 1,4-diiodoperfluorobutane.

13. The method of claim 7 , wherein the second fluorinated olefinic monomer is selected from: hexafluoropropylene, trifluoroethylene, fluoroethylene, vinylidene fluoride, tetrafluoroethylene, perfluoro(methyl vinyl ether), perfluoro(propyl vinyl ether), perfluoro(methoxypropyl vinyl ether), perfluoro(ethoxymethyl vinyl ether), chlorotrifluoroethylene, and combinations thereof.

14. The method of claim 7 , wherein the first and second fluorinated olefinic monomers are polymerized in an emulsion polymerization.

15. The method of claim 7 , wherein the polymerizing step is substantially free of an emulsifier wherein the emulsifier is selected from fluorinated alkanoic acids and salts thereof; fluorinated alkanoic sulphonic acids and salts thereof; fluoroethoxy alkanoic acids and salts thereof; and combinations thereof.

Assignees

• 3M Innovative Properties Co

Inventors

• Guerra Miguel A
• Fukushi Tatsuo
• Wilson Kenneth D

Classifications

• C08F236/18

  containing chlorine · CPC title

• C07C17/278

  of only halogenated hydrocarbons · CPC title

• C08F236/16

  containing halogen · CPC title

• C07C21/18

  containing fluorine · CPC title

• C08F214/18

  Monomers containing fluorine · CPC title