Composition, method of preparing the composition, electrode including the composition, and fuel cell including the electrode

Patent metadata

Field	Value
Publication number	US-10355284-B2
Application number	US-201615160530-A
Country	US
Kind code	B2
Filing date	May 20, 2016
Priority date	Mar 3, 2010
Publication date	Jul 16, 2019
Grant date	Jul 16, 2019

Abstract

A composition containing a uniformly dispersed polyoxazine-based compound, a method of preparing the composition, an electrode including the composition, and a fuel cell including the electrode.

First claim

What is claimed is:

1. A method of preparing the composition comprising a dispersion medium, and polyoxazine-based compound particles dispersed in the dispersion medium, the method comprising:
mixing an oxazine-based monomer and an acid to prepare an acid solution of the oxazine-based monomer; wherein the acid comprises a phosphoric acid-based material;
thermally treating the acid solution of the oxazine-based monomer to obtain a polymerization product;
separating the polyoxazine-based compound from the polymerization product; and
dispersing the polyoxazine-based compound in a dispersion medium; wherein the oxazine-based monomer comprises at least one compound selected from the compounds represented by Formulae 1 through 6 below:

wherein, in Formula 1, R 1 through R 4 are each, independently, a hydrogen atom, a substituted or unsubstituted C 1 -C 20 alkyl group, a substituted or unsubstituted C 1 -C 20 alkoxy group, a substituted or unsubstituted C 2 -C 20 alkenyl group, a substituted or unsubstituted C 2 -C 20 alkynyl group, a substituted or unsubstituted C 6 -C 20 aryl group, a substituted or unsubstituted C 6 -C 20 aryloxy group, a substituted or unsubstituted C 2 -C 20 heteroaryl group, a substituted or unsubstituted C 2 -C 20 heteroaryloxy group, a substituted or unsubstituted C 4 -C 20 carbon ring group, a substituted or unsubstituted C 4 -C 20 carbocyclic oxy group, a substituted or unsubstituted C 2 -C 20 heterocyclic group, a halogen atom, a hydroxy group, or a cyano group; and
R 5 is a substituted or unsubstituted C 1 -C 20 alkyl group, a substituted or unsubstituted C 1 -C 20 alkoxy group, a substituted or unsubstituted C 2 -C 20 alkenyl group, a substituted or unsubstituted C 2 -C 20 alkynyl group, a substituted or unsubstituted C 6 -C 20 aryl group, a substituted or unsubstituted C 6 -C 20 aryloxy group, a substituted or unsubstituted C 7 -C 20 arylalkyl group, a substituted or unsubstituted C 2 -C 20 heteroaryl group, a substituted or unsubstituted C 2 -C 20 heteroaryloxy group, a substituted or unsubstituted C 2 -C 20 heteroarylalkyl group, a substituted or unsubstituted C 4 -C 20 carbocyclic group, a substituted or unsubstituted C 4 -C 20 carbocyclic alkyl group, a substituted or unsubstituted C 2 -C 20 heterocyclic group, or a substituted or unsubstituted C 2 -C 20 heterocyclic alkyl group,

wherein, in Formula 2, R 5 ′ is substituted or unsubstituted C 1 -C 20 alkyl group, a substituted or unsubstituted C 1 -C 20 alkoxy group, a substituted or unsubstituted C 2 -C 20 alkenyl group, a substituted or unsubstituted C 2 -C 20 alkenyl alkynyl group, a substituted or unsubstituted C 6 -C 20 aryl group, a substituted or unsubstituted C 6 -C 20 aryloxy group, a substituted or unsubstituted C 7 -C 20 arylalkyl group, a substituted or unsubstituted C 2 -C 20 heteroaryl group, a substituted or unsubstituted C 2 -C 20 heteroaryloxy group, a substituted or unsubstituted C 2 -C 20 heteroarylalkyl group, a substituted or unsubstituted C 4 -C 20 carbocyclic group, a substituted or unsubstituted C 4 -C 20 carbocyclic alkyl group, a substituted or unsubstituted C 2 -C 20 heterocyclic group, or a substituted or unsubstituted C 2 -C 20 heterocyclic alkyl group, and
R 6 is selected from the group consisting of a substituted or unsubstituted C 1 -C 20 alkylene group, a substituted or unsubstituted C 2 -C 20 alkenylene group, a substituted or unsubstituted C 2 -C 20 alkynylene group, a substituted or unsubstituted C 6 -C 20 arylene group, a substituted or unsubstituted C 2 -C 20 heteroarylene group, —C(═O)—, and —SO 2 —,

wherein, in Formula 3, A, B, C, D and E are all carbon, or one or two of A, B, C, D and E is nitrogen and the others are carbon, and
R 7 and R 8 are linked to form a ring, wherein the ring is a C 6 -C 10 cycloalkyl group, a C 3 -C 10 heteroaryl group, a fused C 3 -C 10 heteroaryl group, a C 3 -C 10 heterocyclic group, or a fused C 3 -C 10 heterocyclic group,

wherein, in Formula 4, A′ is a substituted or unsubstituted C 1 -C 20 heterocyclic group, a substituted or unsubstituted C 4 -C 20 cycloalkyl group, a substituted or unsubstituted C 1 -C 20 alkyl group, and
R 9 to R 16 are each, independently, a hydrogen atom, a C 1 -C 20 alkyl group, a C 1 -C 20 alkoxy group, A C 6 -C 20 aryl group, a C 6 -C 20 aryloxy group, a C 1 -C 20 heteroaryl group, a C 1 -C 20 heteroaryloxy group, a C 4 -C 20 cycloalkyl group, a C 1 -C 20 heterocyclic group, a halogen atom, a cyano group, or a hydroxy group,

wherein, in Formula 5, R 17 and R 18 are each, independently, a C 1 -C 20 alkyl group, a C 1 -C 20 alkoxy group, A C 6 -C 20 aryl group, a C 6 -C 20 aryloxy group or a group represented by Formula 5A below,

wherein, in Formula 5 and 5A, R 19 and R 19 ′ are each, independently, selected from among a hydrogen atom, a C 1 -C 20 alkoxy group, a C 6 -C 20 aryl group, a C 6 -C 20 aryloxy group, a halogenated C 6 -C 20 aryl group, a halogenated C 6 -C 20 aryloxy group, a C 1 -C 20 heteroaryl group, a C 1 -C 20 heteroaryloxy group, a halogenated C 1 -C 20 heteroaryl group, a halogenated C 1 -C 20 heteroaryloxy group, a C 4 -C 20 cycloalkyl group, a halogenated C 4 -C 20 cycloalkyl group, a C 1 -C 20 heterocyclic group or a halogenated C 1 -C 20 heterocyclic group,

wherein, in Formula 6, at least two adjacent groups selected from among R 20 , R 21 and R 22 are linked to form a group represented by Formula 6A below, and the non-selected, remaining group is selected from among a hydrogen atom, a C 1 -C 20 alkyl group, a C 1 -C 20 alkoxy group, C 6 -C 20 aryl group, a C 6 -C 20 aryloxy group, a halogenated C 6 -C 20 aryl group, a halogenated C 6 -C 20 aryloxy group, a C 1 -C 20 heteroaryl group, a C 1 -C 20 heteroaryloxy group, a halogenated C 1 -C 20 heteroaryl group, a halogenated C 1 -C 20 heteroaryloxy group, a C 4 -C 20 carbocyclic group, a halogenated C 4 -C 20 carbocyclic group, a C 1 -C 20 heterocyclic group, and a halogenated C 1 -C 20 heterocyclic group, and
at least two adjacent groups selected from among R 23 , R 24 and R 25 are linked to form the group represented by Formula 6A below, and the non-selected, remaining group is selected from among a C 1 -C 20 alkyl group, a C 1 -C 20 alkoxy group, a C 6 -C 20 aryl group, a C 6 -C 20 aryloxy group, halogenated C 6 -C 20 aryl group, a halogenated C 6 -C 20 aryloxy group, a C 1 -C 20 heteroaryl group, a C 1 -C 20 heteroaryloxy group, a halogenated C 1 -C 20 heteroaryl group, a halogenated C 1 -C 20 heteroaryloxy group, a C 4 -C 20 carbocyclic group, a halogenated C 4 -C 20 carbocyclic group, a C 1 -C 20 heterocyclic group, and a halogenated C 1 -C 20 heterocyclic group,

wherein, in Formula 6A, R 1 ′ is a substituted or unsubstituted C 1 -C 20 alkyl group, a substituted or unsubstituted C 1 -C 20 alkoxy group, a substituted or unsubstituted C 2 -C 20 alkenyl group, a substituted or unsubstituted C 2 -C 20 alkynyl group, a substitut

Assignees

• Samsung Electronics Co Ltd

Inventors

• Park Jung-Ock
• Choi Seong-Woo
• Jeon Woo-Sung
• Yi Jung-Seok
• Uensal Oemer

Classifications

• H01M4/8825

  Methods for deposition of the catalytic active composition · CPC title

• H01M8/1004

  characterised by membrane-electrode assemblies [MEA] (H01M8/12 takes precedence) · CPC title

• C08G73/06

  Polycondensates having nitrogen-containing heterocyclic rings in the main chain of the macromolecule · CPC title

• H01M4/8892

  Impregnation or coating of the catalyst layer, e.g. by an ionomer · CPC title

• H01M4/92

  Metals of platinum group (H01M4/94 {, H01M4/9058} take precedence) · CPC title