Polymer, electrolyte membrane and electrode for a fuel cell, each including the polymer, fuel cell including at least one of the electrolyte membrane, and the electrode

Patent metadata

Field	Value
Publication number	US-9722270-B2
Application number	US-201414338432-A
Country	US
Kind code	B2
Filing date	Jul 23, 2014
Priority date	Jul 30, 2013
Publication date	Aug 1, 2017
Grant date	Aug 1, 2017

Abstract

A polymer including a reaction product of a sulfonated polyarylene ether sulfone and at least one compound selected from a sulfonated compound having a thiol group at a terminal thereof and a sulfonated compound having a hydroxy group at a terminal thereof.

First claim

What is claimed is:

1. A polymer comprising:
a reaction product of a sulfonated polyarylene ether sulfone and
a sulfonated compound comprising a thiol group at a terminal thereof,
wherein the sulfonated compound comprising a thiol group at a terminal thereof is a compound represented by Formula 1:

wherein, in Formula 1,
R 1 to R 16 are each independently selected from a hydrogen atom, a substituted or unsubstituted C1-C40 alkyl group, a substituted or unsubstituted C1-C40 alkoxy group, a substituted or unsubstituted C2-C40 alkenyl group, a substituted or unsubstituted C2-C40 alkynyl group, a substituted or unsubstituted C6-C40 aryl group, a substituted or unsubstituted C7-C40 arylalkyl group, a substituted or unsubstituted C6-C40 aryloxy group, a substituted or unsubstituted C2-C40 heteroaryl group, a substituted or unsubstituted C3-C40 heteroarylalkyl group, a substituted or unsubstituted C2-C40 heteroaryloxy group, a substituted or unsubstituted C4-C40 carbocyclic group, a substituted or unsubstituted C5-C40 carbocyclic alkyl group, a substituted or unsubstituted C4-C40 carbocyclic oxy group, a substituted or unsubstituted C5-C40 carbocyclic alkyloxy group, a substituted or unsubstituted C2-C40 heterocyclic group, a halogen atom, a hydroxy group, and a cyano group,
wherein at least one of R 9 to R 12 is —SO 3 M group, and at least one of R 13 to R 16 is —SO 3 M group where M is hydrogen, sodium, or potassium;
z is 0 or 1;
L is —S(═O) 2 — or —P(═O)Y—, where Y is a C6-C40 aryl group substituted with an —SO 3 M group where M is hydrogen, sodium, or potassium,
n1 is a number from 1 to 5,000; and
A is a group represented by Formula 2:

wherein, in Formula 2,
R 17 to R 24 are each independently selected from a hydrogen atom, a substituted or unsubstituted C1-C40 alkyl group, a substituted or unsubstituted C1-C40 alkoxy group, a substituted or unsubstituted C2-C40 alkenyl group, a substituted or unsubstituted C2-C40 alkynyl group, a substituted or unsubstituted C6-C40 aryl group, a substituted or unsubstituted C7-C40 arylalkyl group, a substituted or unsubstituted C6-C40 aryloxy group, a substituted or unsubstituted C2-C40 heteroaryl group, a substituted or unsubstituted C3-C40 heteroarylalkyl group, a substituted or unsubstituted C2-C40 heteroaryloxy group, a substituted or unsubstituted C4-C40 carbocyclic group, a substituted or unsubstituted C5-C40 carbocyclic alkyl group, a substituted or unsubstituted C4-C40 carbocyclic oxy group, a substituted or unsubstituted C5-C40 carbocyclic alkyloxy group, a substituted or unsubstituted C2-C40 heterocyclic group, a halogen atom, a hydroxy group, and a cyano group.

2. The polymer of claim 1 , wherein the sulfonated compound comprising a thiol group at a terminal thereof is at least one of a compound represented by Formula 3 and a compound represented by Formula 4:

wherein, in Formula 3,
M is hydrogen, sodium, or potassium;
n1 is a number from 1 to 5,000; and
A is a group represented by Formula 2A:

wherein, in Formula 4,
M is hydrogen, sodium, or potassium;
n1 is a number from 1 to 5,000; and
A is a group represented by Formula 2A.

3. The polymer of claim 1 , wherein the sulfonated polyarylene ether sulfone comprises
a first repeating unit represented by Formula 5 and
a second repeating unit represented by Formula 6:

wherein, in Formula 5,
R′ is a single bond, —O—, —S(═O) 2 —, —C(═O)—, or —C(CH 3 ) 2 —;
M is hydrogen, sodium, or potassium; and
k is 0 or 1,

wherein, in Formula 6,
R′ is a single bond, —O—, —S(═O) 2 —, —C(═O)—, or —C(CH 3 ) 2 —; and
k is 0 or 1.

4. The polymer of claim 3 , wherein the first repeating unit represented by Formula 5 is a repeating unit represented by Formula 7:

wherein, in Formula 7,
R′ is a single bond, —O—, —S(═O) 2 —, —C(═O)—, or —C(CH 3 ) 2 —; and
M is hydrogen, sodium, or potassium.

5. The polymer of claim 1 , wherein the sulfonated polyarylene ether sulfone comprises a repeating unit represented by Formula 8 and a repeating unit represented by Formula 9, wherein an amount of the repeating unit represented by Formula 8 is from about 0.01 mole % to about 99.99 mole %, and an amount of the repeating unit represented by Formula 9 is from about 0.01 mole % to about 0.99 mole %:

wherein, in Formula 8, M is hydrogen, sodium, or potassium;

6. The polymer of claim 1 , wherein the sulfonated compound comprising a thiol group at a terminal thereof is selected from a compound represented by Formula 10 and a compound represented by Formula 11:

wherein, in Formula 10,
M is hydrogen, sodium, or potassium;
n1 is a number from 1 to 5,000; and
A is a group represented by Formula 2A,

wherein, in Formula 11,
M is hydrogen, sodium, or potassium;
n1 is a number from 1 to 5,000; and
A is a group represented by Formula 2A.

7. The polymer of claim 1 , wherein an amount of the sulfonated compound comprising a thiol group at a terminal thereof is from about 1 part to about 99 parts by weight based on 100 parts by weight of the sulfonated polyarylene ether sulfone.

8. The polymer of claim 1 , wherein the sulfonated polyarylene ether sulfone has a degree of sulfonation of about 30% to about 95%.

9. The polymer of claim 1 , wherein the polymer is a reaction product of a polyarylene ether sulfone represented by Formula 12 or a polyarylene ether sulfone represented by Formula 13, and a compound represented by Formula 14:

wherein, in Formula 12,
a indicates a mole fraction from about 0.01 to about 0.99, and b indicates a mole fraction from about 0.01 to about 0.99, where a+b=1,

wherein, in Formula 13,
a indicates a mole fraction from about 0.01 to about 0.99, and b indicates a mole fraction from about 0.01 to about 0.99, where a+b=1,

wherein, in Formula 14, n is a number from 1 to 5,000.

10. The polymer of claim 1 , wherein the polymer is a reaction product of a polyarylene ether sulfone represented by Formula 12 or a polyarylene ether sulfone represented by Form

Assignees

• Samsung Electronics Co Ltd
• Univ Seoul Nat R & Db Found
• Univ Seoul Nat R & Db Found

Inventors

• Choi Seong-Woo
• Pak Chan-Ho
• Kim Ki-Hyun
• Lee Jong-Chan

Classifications

• H01M2300/0082

  Organic polymers · CPC title

• H01M8/1032 Primary

  having sulfur, e.g. sulfonated-polyethersulfones [S-PES] · CPC title

• C08G75/23

  Polyethersulfones · CPC title

• H01M2008/1095

  Fuel cells with polymeric electrolytes · CPC title

• H01M8/1034

  having phosphorus, e.g. sulfonated polyphosphazenes [S-PPh] · CPC title