IP Library Granted Patent US 9,035,013
Granted Patent B2
US 9,035,013 · App. 13/812,887 · Granted May 19, 2015

Sulphur-containing triazine monomer that can be used for the synthesis of a polymer membrane for a fuel cell

Inventor: Milan Fedurco (Clermont-Ferrand, FR)
Assignees: COMPAGNIE GENERALE DES ETABLISSEMENTS MICHELIN; MICHELIN RECHERCHE ET TECHNIQUE S.A.
C07D251/24B01D67/0009B01D71/32B01D71/62B01D71/66B01D71/68B01D71/82C08G73/0638C08G73/0644C08J5/2262C08J2381/06H01M8/1027H01M8/103H01M8/1032H01M8/1039H01M2008/1095H01M2300/0082Y02E60/521B01D2325/14B01D2325/26B01D2325/30
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Quick Facts
Patent No.
US 9,035,013
App. No.
13/812,887
Granted
May 19, 2015
Kind
B2
Abstract

A sulphur-containing triazine monomer is provided that can be used in the synthesis of a polymer membrane for a PEM-type fuel cell. The sulphur-containing triazine monomer has a structure corresponding to a formula (I): in which: Tz represents a 1,3,5-triazine nucleus; X 1 and X 2 , which are identical or different, represent S, SO, or SO 2 ; Ar 1 , Ar 2 , Ar 4 and Ar 5 , which are identical or different, represent a substituted or unsubstituted phenylene group; Ar 3 represents a substituted or unsubstituted phenyl group; and Z 1 and Z 2 , which are identical or different, are selected from a group that includes halogens, hydroxyl, alkoxyl, thiol, carboxyl, carboxylates, amine, sulphonamide, acyl chlorides, sulphonyl chlorides, sulphonyl fluorides, isocyanates, and combinations thereof.

Claims (30)

1. A sulphur-containing triazine monomer corresponding to a formula (I):

in which:

Tz represents a 1,3,5-triazine nucleus;

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

Ar 1 , Ar 2 , Ar 4 and Ar 5 , which are identical or different, represent a substituted or unsubstituted phenylene group;

Ar 3 represents a substituted or unsubstituted phenyl group;

Z 1 and Z 2 , which are identical or different, are selected from a group that includes halogens, hydroxyl, alkoxyls, thiol, carboxyls, carboxylates, amino, sulphonamido, acyl chloride, sulphonyl chloride, sulphonyl fluoride, isocyanate, and combinations thereof.

2. The triazine monomer according to claim 1 , wherein Z 1 and Z 2 , which are identical or different, are selected from a group that includes halogens, hydroxyl, thiol, and combinations thereof.

3. The triazine monomer according to claim 2 , wherein the triazine monomer corresponds to a formula (II):

4. The triazine monomer according to claim 2 , wherein Z 1 and Z 2 , which are identical or different, are halogens.

5. The triazine monomer according to claim 4 , wherein the triazine monomer corresponds to a formula (III):

6. The triazine monomer according to claim 4 , wherein the triazine monomer corresponds to a formula (IV):

7. The triazine monomer according to claim 1 , wherein the triazine monomer is a suphonated monomer that includes a sulphonic (—SO 3 H) group or a sulphonate (—SO 3 M) group, in which M represents an alkali metal cation.

8. The triazine monomer according to claim 7 , wherein the sulphonic (—SO 3 H) group or the sulphonate (—SO 3 M) group is carried by a phenyl group or a phenylene group or by at a substituent thereof.

9. A process for synthesizing a triazine polymer, comprising:

performing polycondensation of a triazine monomer corresponding to a formula (I):

in which:

Tz represents a 1,3,5-triazine nucleus;

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

Ar 1 , Ar 2 , Ar 4 and Ar 5 , which are identical or different, represent a substituted or unsubstituted phenylene group;

Ar a represents a substituted or unsubstituted phenyl group;

Z 1 and Z 2 , which are identical or different, are selected from a group that includes halogens, hydroxyl, alkoxyls, thiol, carboxyls, carboxylates, amino, sulphonamido, acyl chloride, sulphonyl chloride, sulphonyl fluoride, isocyanate, and combinations thereof.

10. A method of manufacturing a PEM-type fuel cell, comprising:

using a triazine monomer or produce a polymer membrane used in the PEM-type fuel cell, wherein the triazine monomer corresponds to a formula (I):

in which:

Tz represents a 1,3,5-triazine nucleus;

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

Ar 1 , Ar 2 , Ar 4 and Ar 5 , which are identical or different, represent a substituted or unsubstituted phenylene group;

Ar a represents a substituted or unsubstituted phenyl group;

Z 1 and Z 2 , which are identical or different, are selected from a group that includes halogens, hydroxyl, alkoxyls, thiol, carboxyls, carboxylates, amino, sulphonamido, acyl chloride, sulphonyl chloride, sulphonyl fluoride, isocyanate, and combinations thereof.

Assignments (2)
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 →
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 030081/0010 →
Priority Claims (1)
FR 10 56438 · Aug 4, 2010 · national
Continuity (1)
Related Publication 20130184428A1 · Jul 18, 2013