IP Library Granted Patent US 9,126,907
Granted Patent B2
US 9,126,907 · App. 13/812,892 · Granted Sep 8, 2015

Sulphur-containing and sulphonated aromatic perfluoroalkane monomer

Inventor: Milan Fedurco (Clermont-Ferrand, FR)
Assignees: COMPAGNIE GENERALE DES ETABLISSEMENTS MICHELIN; MICHELIN RECHERCHE ET TECHNIQUE S.A.
C07C317/14B01J49/0047C07C323/66C08G75/20H01M8/1025H01M8/1027H01M8/1032H01M8/1039H01M8/1088Y02E60/521
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Quick Facts
Patent No.
US 9,126,907
App. No.
13/812,892
Granted
Sep 8, 2015
Kind
B2
Abstract

A sulphur-containing and sulphonated aromatic perfluoroalkane monomer is provided that can be used for the manufacture of a polymer membrane for a PEM-type fuel cell. The perfluoroalkane monomer is a functionalized polymer that has a structure corresponding to a formula (I): E 1 -Ar 1 —X 1 —(CF 2 ) n —X 2 —Ar 2 -E 2   (I) in which: n is in a range from 1 to 20; X 1 and X 2 , which are identical or different, represent S, SO, or SO 2 ; Ar 1 , Ar 2 , which are identical or different, represent a phenylene group, at least one of Ar 1 and Ar 2 bearing a sulphonic (—SO 3 H) group or a sulphonate (—SO 3 M) group, in which M represents an alkali metal cation; and E 1 and E 2 , which are identical or different, represent an electrophilic group such as a halogen, specifically fluorine or chlorine.

Claims (22)

1. A sulphur-containing and sulphonated aromatic perfluoroalkane monomer corresponding to a formula (I):

E 1 -Ar 1 —X 1 —(CF 2 ) n —X 2 —Ar 2 -E 2   (I)

in which:

n is in a range from 1 to 20;

X 1 and X 2 , which are identical or different, represent S, SO, or SO 2 ;

Ar 1 , Ar 2 , which are identical or different, represent a phenylene group, at least one of Ar 1 and Ar 2 bearing a sulphonic (—SO 3 H) group or a sulphonate (—SO 3 M) group, in which M represents an alkali metal cation; and

E 1 and E 2 , which are identical or different, represent an electrophilic functional group.

2. The monomer according to claim 1 , wherein n is in a range from 2 to 20.

3. The monomer according to claim 1 , wherein n is in a range from 2 to 8.

4. The monomer according to claim 1 , wherein E 1 and E 2 , which are identical or different, are chosen from the group consisting of halogen, carboxyl, acyl chloride, sulphonyl chloride, sulphonyl fluoride, isocyanate, and combinations thereof.

5. The monomer according to claim 4 , wherein E 1 and E 2 , which are identical or different, represent halogens.

6. The monomer according to claim 5 , wherein the monomer corresponds to a formula (II):

F—Ar 1 —X 1 —(CF 2 ) n —X 2 —Ar 2 —F  (II).

7. The monomer according to claim 5 , wherein the monomer corresponds to a formula (III):

Cl—Ar 1 —X 1 —(CF 2 ) n —X 2 —Ar 2 —Cl  (III).

8. The monomer according to claim 1 , wherein n is equal to 4.

9. The monomer according to claim 2 , wherein n is equal to 4.

10. The monomer according to claim 3 , wherein n is equal to 4.

11. The monomer according to claim 4 , wherein n is equal to 4.

12. The monomer according to claim 5 , wherein n is equal to 4.

13. The monomer according to claim 6 , wherein n is equal to 4.

14. The monomer according to claim 7 , wherein n is equal to 4.

Assignments (4)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Nov 7, 2017
From: MICHELIN RECHERCHE ET TECHNIQUE S.A.
To: COMPAGNIE GENERALE DES ETABLISSEMENTS MICHELIN
Reel/Frame 044049/0310 →
RELEASE OF SECURITY INTEREST Recorded Sep 27, 2013
From: VITAG INVESTMENT HOLDINGS LLC
To: VITAG CORPORATION
Reel/Frame 031295/0179 →
PATENT SECURITY AGREEMENT Recorded Aug 21, 2013
From: VITAG CORPORATION
To: VITAG INVESTMENT HOLDINGS LLC
Reel/Frame 031059/0574 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Mar 25, 2013
From: FEDURCO, MILAN
To: COMPAGNIE GENERALE DES ETABLISSEMENTS MICHELIN; MICHELIN RECHERCHE ET TECHNIQUE S.A.
Reel/Frame 030080/0990 →
Priority Claims (1)
FR 10 56439 · Aug 4, 2010 · national
Continuity (1)
Related Publication 20130197110A1 · Aug 1, 2013