Polyphenylene compound

Patent metadata

Field	Value
Publication number	US-11312818-B2
Application number	US-201816958509-A
Country	US
Kind code	B2
Filing date	Dec 27, 2018
Priority date	Dec 28, 2017
Publication date	Apr 26, 2022
Grant date	Apr 26, 2022

Abstract

This is to provide a non-halogen containing compound excellent in proton conductivity and capable of suitably being used for a polymer electrolytic fuel cellThe compound of the present invention has a structure represented by the following general formula (I).(In the above-mentioned general formula (I), “l” and “n” are molar fractions when l+n=1.0, and 0≤l<1.0 and 0<n≤1.0, A represents a structure represented by the following general formula (II) or (III), B represents a structure represented by the following general formula (VII), the respective structural units are random copolymerized, and at least one benzene ring in the formula (I) has at least one sulfo group.)(In the above-mentioned general formula (II) or (III), R1 to R4 are each independently selected from hydrogen and an alkyl group having 1 to 3 carbon atoms, le and R2 form together with the carbon atom, they are attached to, an aromatic ring or a fused aromatic ring and R3 and R4 form together with the carbon atom, they are attached to, an aromatic ring or a fused aromatic ring, or R1, R3 and R4 are hydrogens and R2 is a single bond and bonded to the carbon of “c”,X is a single bond, or a structure represented by the following formula (IV), the following formula (V) or the following formula (VI),when X is a single bond, bonds “a”s are both bonded at ortho positions or both bonded at meta positions relative to the carbons bonded to X, when X is a structure represented by the following formula (IV), bonds “a”s are both bonded at para positions relative to the carbons bonded to X, and when it is a structure represented by the following formula (V), bonds “a”s are both bonded at para positions or both bonded at meta positions relative to the carbons bonded to x,when X is a structure represented by the following formula (VI), the bonds “a”s in the above-mentioned general formula (II) or (III) exist only one of these, and A binds to other structure or a structural unit by one of the bonds “a”s and the bond “b”.)

First claim

The invention claimed is:

1. A compound having a structure represented by the following general formula (I):

in the above-mentioned general formula (I), “1” and “n” are molar fractions when l+n=1.0, and 0≤l<1.0 and 0<n≤1.0,
A represents a structure represented by the following general formula (II) or (III),
B represents a structure represented by the following general formula (VII),
the respective structural units are random copolymerized, and
at least one benzene ring in the formula (I) has at least one sulfo group,

in the above-mentioned general formula (II) or (III), le to R 4 are each independently selected from hydrogen and an alkyl group having 1 to 3 carbon atoms, R 1 and R 2 form together with the carbon atom, they are attached to, an aromatic ring or a fused aromatic ring and R 3 and R 4 form together with the carbon atom, they are attached to, an aromatic ring or a fused aromatic ring, or R 1 , R 3 and R 4 are hydrogens and R 2 is a single bond and bonded to the carbon of “c”,
X is a single bond, or a structure represented by the following formula (IV), the following formula (V) or the following formula (VI),
when X is a single bond, bonds “a”s are both bonded at ortho positions or both bonded at meta positions relative to the carbons bonded to X, when X is a structure represented by the following formula (IV), the bonds “a”s are both bonded at para positions relative to the carbons bonded to X, and when it is a structure represented by the following formula (V), the bonds “a”s are both bonded at para positions or both bonded at meta positions relative to the carbons bonded to X, when X is a structure represented by the following formula (VI), the bonds “a”s in the above-mentioned general formula (II) or (III) exist only one of these, and A binds to other structure or a structural unit by one of the bonds “a”s and the bond “b”.

2. The compound according to claim 1 , wherein, in the above-mentioned general formula (I), the structure represented by A is at least one kind selected from the group consisting of:

3. The compound according to claim 1 , which is for a fuel cell.

4. The compound according to claim 3 , which is used for an electrolyte of an anode catalyst layer and/or a cathode catalyst layer of a fuel cell.

5. A catalyst layer of a fuel cell which contains the compound according to claim 1 .

6. A method for producing the compound according to claim 1 , which comprises Step 1 of reacting a compound represented by the following formula (VIII), a compound represented by the following formula (IX) and optionally a compound represented by the following formula (X) to obtain a compound represented by the following formula (XI),

in the above-mentioned general formula (IX) and (XI), “1”, “n”, A and B have the same meanings as defined in the formula (I), provided that each benzene ring does not have a sulfo group, and
Step 2 of sulfonating the compound represented by the above-mentioned formula (XI) to obtain the compound represented by the above-mentioned formula (I).

7. A method for producing the compound according to claim 1 , which comprises a step of reacting: an amine salt of a compound of formula (VIII) having at least one sulfo group which became an amine salt in a compound of the following formula (VIII), a compound represented by the following formula (IX) and optionally a compound represented by the following formula (X) to obtain the compound represented by the above-mentioned formula (I):

in the above-mentioned general formula (IX), A has the same meaning as defined in the formula (I), and wherein the compound of formula (VIII) is substituted with at least one sulfo group, which formulates the amine salt.

Assignees

• Nissan Chemical Corp

Inventors

• Nakazawa Taichi
• Kondo Shoichi

Classifications

• H01M8/1023

  having only carbon, e.g. polyarylenes, polystyrenes or polybutadiene-styrenes · CPC title

• H01M2300/0082

  Organic polymers · CPC title

• H01M2008/1095

  Fuel cells with polymeric electrolytes · CPC title

• H01M8/1072

  by chemical reactions, e.g. in situ polymerisation or in situ crosslinking · CPC title

• C08G2261/1452

  containing sulfonyl or sulfonate-groups · CPC title