JP2006507372A - プロトン伝導性膜およびその使用 - Google Patents
プロトン伝導性膜およびその使用 Download PDFInfo
- Publication number
- JP2006507372A JP2006507372A JP2004516602A JP2004516602A JP2006507372A JP 2006507372 A JP2006507372 A JP 2006507372A JP 2004516602 A JP2004516602 A JP 2004516602A JP 2004516602 A JP2004516602 A JP 2004516602A JP 2006507372 A JP2006507372 A JP 2006507372A
- Authority
- JP
- Japan
- Prior art keywords
- acid
- aromatic
- membrane
- groups
- group
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 239000012528 membrane Substances 0.000 title claims abstract description 96
- 125000003118 aryl group Chemical group 0.000 claims abstract description 49
- 239000000446 fuel Substances 0.000 claims abstract description 39
- 229920000642 polymer Polymers 0.000 claims abstract description 39
- 125000000542 sulfonic acid group Chemical group 0.000 claims abstract description 8
- 229920001940 conductive polymer Polymers 0.000 claims abstract description 7
- 239000002322 conducting polymer Substances 0.000 claims abstract description 5
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 49
- -1 heterocyclic aromatic diaminocarboxylic acids Chemical class 0.000 claims description 35
- 239000002253 acid Substances 0.000 claims description 33
- 125000006615 aromatic heterocyclic group Chemical group 0.000 claims description 28
- 125000002950 monocyclic group Chemical group 0.000 claims description 24
- 125000003367 polycyclic group Chemical group 0.000 claims description 24
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims description 23
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 19
- 238000000034 method Methods 0.000 claims description 17
- 239000000203 mixture Substances 0.000 claims description 16
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 claims description 15
- 229920000137 polyphosphoric acid Polymers 0.000 claims description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 12
- 125000000217 alkyl group Chemical group 0.000 claims description 10
- 239000003795 chemical substances by application Substances 0.000 claims description 10
- 229910052760 oxygen Inorganic materials 0.000 claims description 10
- 239000001301 oxygen Substances 0.000 claims description 9
- 150000000000 tetracarboxylic acids Chemical class 0.000 claims description 9
- 125000003837 (C1-C20) alkyl group Chemical group 0.000 claims description 8
- OYFRNYNHAZOYNF-UHFFFAOYSA-N 2,5-dihydroxyterephthalic acid Chemical compound OC(=O)C1=CC(O)=C(C(O)=O)C=C1O OYFRNYNHAZOYNF-UHFFFAOYSA-N 0.000 claims description 8
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 8
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 claims description 8
- WJJMNDUMQPNECX-UHFFFAOYSA-N dipicolinic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=N1 WJJMNDUMQPNECX-UHFFFAOYSA-N 0.000 claims description 8
- 229910052757 nitrogen Inorganic materials 0.000 claims description 8
- ARCGXLSVLAOJQL-UHFFFAOYSA-N trimellitic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C(C(O)=O)=C1 ARCGXLSVLAOJQL-UHFFFAOYSA-N 0.000 claims description 8
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 7
- 229910052739 hydrogen Inorganic materials 0.000 claims description 7
- 239000000178 monomer Substances 0.000 claims description 7
- 150000003628 tricarboxylic acids Chemical class 0.000 claims description 7
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 6
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 6
- 150000001805 chlorine compounds Chemical class 0.000 claims description 6
- 150000002148 esters Chemical class 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 6
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 claims description 6
- 229910052717 sulfur Inorganic materials 0.000 claims description 6
- 239000011593 sulfur Substances 0.000 claims description 6
- KLSJWNVTNUYHDU-UHFFFAOYSA-N Amitrole Chemical group NC1=NC=NN1 KLSJWNVTNUYHDU-UHFFFAOYSA-N 0.000 claims description 5
- 150000008065 acid anhydrides Chemical class 0.000 claims description 5
- 150000008064 anhydrides Chemical class 0.000 claims description 5
- 150000001875 compounds Chemical class 0.000 claims description 5
- 238000010438 heat treatment Methods 0.000 claims description 5
- KEQGZUUPPQEDPF-UHFFFAOYSA-N 1,3-dichloro-5,5-dimethylimidazolidine-2,4-dione Chemical compound CC1(C)N(Cl)C(=O)N(Cl)C1=O KEQGZUUPPQEDPF-UHFFFAOYSA-N 0.000 claims description 4
- CDOWNLMZVKJRSC-UHFFFAOYSA-N 2-hydroxyterephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C(O)=C1 CDOWNLMZVKJRSC-UHFFFAOYSA-N 0.000 claims description 4
- WAJQSFFBBJKSBB-UHFFFAOYSA-N 4,5-dihydroxynaphthalene-2,7-dicarboxylic acid Chemical compound OC1=CC(C(O)=O)=CC2=CC(C(=O)O)=CC(O)=C21 WAJQSFFBBJKSBB-UHFFFAOYSA-N 0.000 claims description 4
- LFEWXDOYPCWFHR-UHFFFAOYSA-N 4-(4-carboxybenzoyl)benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1C(=O)C1=CC=C(C(O)=O)C=C1 LFEWXDOYPCWFHR-UHFFFAOYSA-N 0.000 claims description 4
- WVDRSXGPQWNUBN-UHFFFAOYSA-N 4-(4-carboxyphenoxy)benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1OC1=CC=C(C(O)=O)C=C1 WVDRSXGPQWNUBN-UHFFFAOYSA-N 0.000 claims description 4
- NEQFBGHQPUXOFH-UHFFFAOYSA-N 4-(4-carboxyphenyl)benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1C1=CC=C(C(O)=O)C=C1 NEQFBGHQPUXOFH-UHFFFAOYSA-N 0.000 claims description 4
- VNLYHYHJIXGBFX-UHFFFAOYSA-N 4-(trifluoromethyl)phthalic acid Chemical compound OC(=O)C1=CC=C(C(F)(F)F)C=C1C(O)=O VNLYHYHJIXGBFX-UHFFFAOYSA-N 0.000 claims description 4
- BCEQKAQCUWUNML-UHFFFAOYSA-N 4-hydroxybenzene-1,3-dicarboxylic acid Chemical compound OC(=O)C1=CC=C(O)C(C(O)=O)=C1 BCEQKAQCUWUNML-UHFFFAOYSA-N 0.000 claims description 4
- XFFZVIRSYFJKEX-UHFFFAOYSA-N 4-phenylpyridine-2,5-dicarboxylic acid Chemical compound C1=NC(C(=O)O)=CC(C=2C=CC=CC=2)=C1C(O)=O XFFZVIRSYFJKEX-UHFFFAOYSA-N 0.000 claims description 4
- QNVNLUSHGRBCLO-UHFFFAOYSA-N 5-hydroxybenzene-1,3-dicarboxylic acid Chemical compound OC(=O)C1=CC(O)=CC(C(O)=O)=C1 QNVNLUSHGRBCLO-UHFFFAOYSA-N 0.000 claims description 4
- XTHPWXDJESJLNJ-UHFFFAOYSA-N chlorosulfonic acid Substances OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 claims description 4
- MPFLRYZEEAQMLQ-UHFFFAOYSA-N dinicotinic acid Chemical compound OC(=O)C1=CN=CC(C(O)=O)=C1 MPFLRYZEEAQMLQ-UHFFFAOYSA-N 0.000 claims description 4
- GWZCCUDJHOGOSO-UHFFFAOYSA-N diphenic acid Chemical compound OC(=O)C1=CC=CC=C1C1=CC=CC=C1C(O)=O GWZCCUDJHOGOSO-UHFFFAOYSA-N 0.000 claims description 4
- 239000006185 dispersion Substances 0.000 claims description 4
- MJIVRKPEXXHNJT-UHFFFAOYSA-N lutidinic acid Chemical compound OC(=O)C1=CC=NC(C(O)=O)=C1 MJIVRKPEXXHNJT-UHFFFAOYSA-N 0.000 claims description 4
- GMIOYJQLNFNGPR-UHFFFAOYSA-N pyrazine-2,5-dicarboxylic acid Chemical compound OC(=O)C1=CN=C(C(O)=O)C=N1 GMIOYJQLNFNGPR-UHFFFAOYSA-N 0.000 claims description 4
- HLRLQGYRJSKVNX-UHFFFAOYSA-N pyrimidine-2,4-dicarboxylic acid Chemical compound OC(=O)C1=CC=NC(C(O)=O)=N1 HLRLQGYRJSKVNX-UHFFFAOYSA-N 0.000 claims description 4
- FOMVFKTYQSZBMJ-UHFFFAOYSA-N 1,5-dihydroxycyclohexa-3,5-diene-1,2-dicarboxylic acid Chemical compound OC(=O)C1C=CC(O)=CC1(O)C(O)=O FOMVFKTYQSZBMJ-UHFFFAOYSA-N 0.000 claims description 3
- UKGMFBZPIQCNPM-UHFFFAOYSA-N 1,6-dihydroxycyclohexa-3,5-diene-1,2-dicarboxylic acid Chemical compound OC(=O)C1C=CC=C(O)C1(O)C(O)=O UKGMFBZPIQCNPM-UHFFFAOYSA-N 0.000 claims description 3
- YDMVPJZBYSWOOP-UHFFFAOYSA-N 1h-pyrazole-3,5-dicarboxylic acid Chemical compound OC(=O)C=1C=C(C(O)=O)NN=1 YDMVPJZBYSWOOP-UHFFFAOYSA-N 0.000 claims description 3
- HSTOKWSFWGCZMH-UHFFFAOYSA-N 3,3'-diaminobenzidine Chemical group C1=C(N)C(N)=CC=C1C1=CC=C(N)C(N)=C1 HSTOKWSFWGCZMH-UHFFFAOYSA-N 0.000 claims description 3
- QXGJCWSBOZXWOV-UHFFFAOYSA-N 3,4-dihydroxyphthalic acid Chemical compound OC(=O)C1=CC=C(O)C(O)=C1C(O)=O QXGJCWSBOZXWOV-UHFFFAOYSA-N 0.000 claims description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 3
- SCKXCAADGDQQCS-UHFFFAOYSA-N Performic acid Chemical compound OOC=O SCKXCAADGDQQCS-UHFFFAOYSA-N 0.000 claims description 3
- 125000003277 amino group Chemical group 0.000 claims description 3
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- 239000011261 inert gas Substances 0.000 claims description 3
- OLAPPGSPBNVTRF-UHFFFAOYSA-N naphthalene-1,4,5,8-tetracarboxylic acid Chemical compound C1=CC(C(O)=O)=C2C(C(=O)O)=CC=C(C(O)=O)C2=C1C(O)=O OLAPPGSPBNVTRF-UHFFFAOYSA-N 0.000 claims description 3
- ABMFBCRYHDZLRD-UHFFFAOYSA-N naphthalene-1,4-dicarboxylic acid Chemical compound C1=CC=C2C(C(=O)O)=CC=C(C(O)=O)C2=C1 ABMFBCRYHDZLRD-UHFFFAOYSA-N 0.000 claims description 3
- WPUMVKJOWWJPRK-UHFFFAOYSA-N naphthalene-2,7-dicarboxylic acid Chemical compound C1=CC(C(O)=O)=CC2=CC(C(=O)O)=CC=C21 WPUMVKJOWWJPRK-UHFFFAOYSA-N 0.000 claims description 3
- CHGYKYXGIWNSCD-UHFFFAOYSA-N pyridine-2,4,6-tricarboxylic acid Chemical compound OC(=O)C1=CC(C(O)=O)=NC(C(O)=O)=C1 CHGYKYXGIWNSCD-UHFFFAOYSA-N 0.000 claims description 3
- 150000003457 sulfones Chemical class 0.000 claims description 3
- 150000003460 sulfonic acids Chemical class 0.000 claims description 3
- 150000003467 sulfuric acid derivatives Chemical class 0.000 claims description 3
- PIPQOFRJDBZPFR-UHFFFAOYSA-N 1h-benzimidazole-5,6-dicarboxylic acid Chemical compound C1=C(C(O)=O)C(C(=O)O)=CC2=C1NC=N2 PIPQOFRJDBZPFR-UHFFFAOYSA-N 0.000 claims description 2
- WFNRNCNCXRGUKN-UHFFFAOYSA-N 2,3,5,6-tetrafluoroterephthalic acid Chemical compound OC(=O)C1=C(F)C(F)=C(C(O)=O)C(F)=C1F WFNRNCNCXRGUKN-UHFFFAOYSA-N 0.000 claims description 2
- KKTUQAYCCLMNOA-UHFFFAOYSA-N 2,3-diaminobenzoic acid Chemical compound NC1=CC=CC(C(O)=O)=C1N KKTUQAYCCLMNOA-UHFFFAOYSA-N 0.000 claims description 2
- PGRIMKUYGUHAKH-UHFFFAOYSA-N 2,4,5,6-tetrafluorobenzene-1,3-dicarboxylic acid Chemical compound OC(=O)C1=C(F)C(F)=C(F)C(C(O)=O)=C1F PGRIMKUYGUHAKH-UHFFFAOYSA-N 0.000 claims description 2
- YUWKPDBHJFNMAD-UHFFFAOYSA-N 2-fluoroterephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C(F)=C1 YUWKPDBHJFNMAD-UHFFFAOYSA-N 0.000 claims description 2
- YJLVXRPNNDKMMO-UHFFFAOYSA-N 3,4,5,6-tetrafluorophthalic acid Chemical compound OC(=O)C1=C(F)C(F)=C(F)C(F)=C1C(O)=O YJLVXRPNNDKMMO-UHFFFAOYSA-N 0.000 claims description 2
- BBCQSMSCEJBIRD-UHFFFAOYSA-N 3-fluorophthalic acid Chemical compound OC(=O)C1=CC=CC(F)=C1C(O)=O BBCQSMSCEJBIRD-UHFFFAOYSA-N 0.000 claims description 2
- RQBIGPMJQUKYAH-UHFFFAOYSA-N 4-(3,4-diaminophenoxy)benzene-1,2-diamine Chemical compound C1=C(N)C(N)=CC=C1OC1=CC=C(N)C(N)=C1 RQBIGPMJQUKYAH-UHFFFAOYSA-N 0.000 claims description 2
- JKETWUADWJKEKN-UHFFFAOYSA-N 4-(3,4-diaminophenyl)sulfonylbenzene-1,2-diamine Chemical compound C1=C(N)C(N)=CC=C1S(=O)(=O)C1=CC=C(N)C(N)=C1 JKETWUADWJKEKN-UHFFFAOYSA-N 0.000 claims description 2
- UITKHKNFVCYWNG-UHFFFAOYSA-N 4-(3,4-dicarboxybenzoyl)phthalic acid Chemical compound C1=C(C(O)=O)C(C(=O)O)=CC=C1C(=O)C1=CC=C(C(O)=O)C(C(O)=O)=C1 UITKHKNFVCYWNG-UHFFFAOYSA-N 0.000 claims description 2
- LFBALUPVVFCEPA-UHFFFAOYSA-N 4-(3,4-dicarboxyphenyl)phthalic acid Chemical compound C1=C(C(O)=O)C(C(=O)O)=CC=C1C1=CC=C(C(O)=O)C(C(O)=O)=C1 LFBALUPVVFCEPA-UHFFFAOYSA-N 0.000 claims description 2
- PHQYMDAUTAXXFZ-UHFFFAOYSA-N 4-[2-(4-carboxyphenyl)-1,1,1,3,3,3-hexafluoropropan-2-yl]benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1C(C(F)(F)F)(C(F)(F)F)C1=CC=C(C(O)=O)C=C1 PHQYMDAUTAXXFZ-UHFFFAOYSA-N 0.000 claims description 2
- HAEJSGLKJYIYTB-ZZXKWVIFSA-N 4-carboxycinnamic acid Chemical compound OC(=O)\C=C\C1=CC=C(C(O)=O)C=C1 HAEJSGLKJYIYTB-ZZXKWVIFSA-N 0.000 claims description 2
- QURGMSIQFRADOZ-UHFFFAOYSA-N 5-(3,5-dicarboxyphenyl)benzene-1,3-dicarboxylic acid Chemical compound OC(=O)C1=CC(C(O)=O)=CC(C=2C=C(C=C(C=2)C(O)=O)C(O)=O)=C1 QURGMSIQFRADOZ-UHFFFAOYSA-N 0.000 claims description 2
- MMHLSHSAOIJBHI-UHFFFAOYSA-N 5-(3-carboxyphenyl)benzene-1,3-dicarboxylic acid Chemical compound OC(=O)C1=CC=CC(C=2C=C(C=C(C=2)C(O)=O)C(O)=O)=C1 MMHLSHSAOIJBHI-UHFFFAOYSA-N 0.000 claims description 2
- KBZFDRWPMZESDI-UHFFFAOYSA-N 5-aminobenzene-1,3-dicarboxylic acid Chemical compound NC1=CC(C(O)=O)=CC(C(O)=O)=C1 KBZFDRWPMZESDI-UHFFFAOYSA-N 0.000 claims description 2
- AUIOTTUHAZONIC-UHFFFAOYSA-N 5-fluorobenzene-1,3-dicarboxylic acid Chemical compound OC(=O)C1=CC(F)=CC(C(O)=O)=C1 AUIOTTUHAZONIC-UHFFFAOYSA-N 0.000 claims description 2
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims description 2
- 239000002879 Lewis base Substances 0.000 claims description 2
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 2
- 125000002252 acyl group Chemical group 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- ANUAIBBBDSEVKN-UHFFFAOYSA-N benzene-1,2,4,5-tetramine Chemical compound NC1=CC(N)=C(N)C=C1N ANUAIBBBDSEVKN-UHFFFAOYSA-N 0.000 claims description 2
- ZOQOMVWXXWHKGT-UHFFFAOYSA-N benzene-1,3,5-tricarboxylic acid Chemical compound OC(=O)C1=CC(C(O)=O)=CC(C(O)=O)=C1.OC(=O)C1=CC(C(O)=O)=CC(C(O)=O)=C1 ZOQOMVWXXWHKGT-UHFFFAOYSA-N 0.000 claims description 2
- NLNRQJQXCQVDQJ-UHFFFAOYSA-N bis(3,4-diaminophenyl)methanone Chemical compound C1=C(N)C(N)=CC=C1C(=O)C1=CC=C(N)C(N)=C1 NLNRQJQXCQVDQJ-UHFFFAOYSA-N 0.000 claims description 2
- 239000011248 coating agent Substances 0.000 claims description 2
- 238000000576 coating method Methods 0.000 claims description 2
- 125000001142 dicarboxylic acid group Chemical group 0.000 claims description 2
- NEQVFHFOWYYPBS-UHFFFAOYSA-M dimethyl(3-triphenylphosphaniumylpropyl)azanium;dibromide Chemical compound Br.[Br-].C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(CCCN(C)C)C1=CC=CC=C1 NEQVFHFOWYYPBS-UHFFFAOYSA-M 0.000 claims description 2
- 238000000921 elemental analysis Methods 0.000 claims description 2
- 150000007527 lewis bases Chemical class 0.000 claims description 2
- 125000004437 phosphorous atom Chemical group 0.000 claims description 2
- 229910052698 phosphorus Inorganic materials 0.000 claims description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 2
- IAYUQKZZQKUOFL-UHFFFAOYSA-N pyridine-2,3,5,6-tetramine Chemical compound NC1=CC(N)=C(N)N=C1N IAYUQKZZQKUOFL-UHFFFAOYSA-N 0.000 claims description 2
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 claims 2
- RJWSLEMWVKCUCE-UHFFFAOYSA-N 1,2-dihydroxycyclohexa-3,5-diene-1,3-dicarboxylic acid Chemical compound OC1C(C(O)=O)=CC=CC1(O)C(O)=O RJWSLEMWVKCUCE-UHFFFAOYSA-N 0.000 claims 1
- GOEWOMATKBPGDT-UHFFFAOYSA-N 2,5-dihydroxybenzene-1,3-dicarboxylic acid Chemical compound OC(=O)C1=CC(O)=CC(C(O)=O)=C1O GOEWOMATKBPGDT-UHFFFAOYSA-N 0.000 claims 1
- GWHLJVMSZRKEAQ-UHFFFAOYSA-N 3-(2,3-dicarboxyphenyl)phthalic acid Chemical compound OC(=O)C1=CC=CC(C=2C(=C(C(O)=O)C=CC=2)C(O)=O)=C1C(O)=O GWHLJVMSZRKEAQ-UHFFFAOYSA-N 0.000 claims 1
- ILPWTQGYOZFLBN-UHFFFAOYSA-N 4-[(3,4-diaminophenyl)methyl]benzene-1,2-diamine Chemical compound C1=C(N)C(N)=CC=C1CC1=CC=C(N)C(N)=C1 ILPWTQGYOZFLBN-UHFFFAOYSA-N 0.000 claims 1
- 238000003556 assay Methods 0.000 claims 1
- 125000002843 carboxylic acid group Chemical group 0.000 claims 1
- OBKARQMATMRWQZ-UHFFFAOYSA-N naphthalene-1,2,5,6-tetracarboxylic acid Chemical compound OC(=O)C1=C(C(O)=O)C=CC2=C(C(O)=O)C(C(=O)O)=CC=C21 OBKARQMATMRWQZ-UHFFFAOYSA-N 0.000 claims 1
- SQBICXVJCSMSPH-UHFFFAOYSA-N naphthalene-1,5-dicarboxylic acid;naphthalene-2,6-dicarboxylic acid Chemical compound C1=C(C(O)=O)C=CC2=CC(C(=O)O)=CC=C21.C1=CC=C2C(C(=O)O)=CC=CC2=C1C(O)=O SQBICXVJCSMSPH-UHFFFAOYSA-N 0.000 claims 1
- 239000005518 polymer electrolyte Substances 0.000 abstract description 17
- 239000000463 material Substances 0.000 abstract description 6
- 238000004519 manufacturing process Methods 0.000 abstract description 4
- 239000000126 substance Substances 0.000 abstract description 4
- 238000002047 photoemission electron microscopy Methods 0.000 abstract description 2
- 229920001483 poly(ethyl methacrylate) polymer Polymers 0.000 abstract description 2
- 229920002480 polybenzimidazole Polymers 0.000 description 33
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 24
- 235000011007 phosphoric acid Nutrition 0.000 description 23
- 239000000243 solution Substances 0.000 description 23
- 239000007789 gas Substances 0.000 description 10
- 229920005597 polymer membrane Polymers 0.000 description 10
- 238000012545 processing Methods 0.000 description 9
- 239000000654 additive Substances 0.000 description 8
- 229920006254 polymer film Polymers 0.000 description 8
- 238000006277 sulfonation reaction Methods 0.000 description 8
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 7
- 239000004693 Polybenzimidazole Substances 0.000 description 7
- 239000003054 catalyst Substances 0.000 description 7
- 239000011521 glass Substances 0.000 description 7
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 230000007062 hydrolysis Effects 0.000 description 6
- 238000006460 hydrolysis reaction Methods 0.000 description 6
- 239000011550 stock solution Substances 0.000 description 6
- 239000003792 electrolyte Substances 0.000 description 5
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 4
- 230000009471 action Effects 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 238000005342 ion exchange Methods 0.000 description 4
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 4
- 238000006116 polymerization reaction Methods 0.000 description 4
- 230000008569 process Effects 0.000 description 4
- XSCHRSMBECNVNS-UHFFFAOYSA-N quinoxaline Chemical compound N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 description 4
- 238000002407 reforming Methods 0.000 description 4
- YWJNJZBDYHRABW-UHFFFAOYSA-N 2,4-dihydroxybenzene-1,3-dicarboxylic acid Chemical compound OC(=O)C1=CC=C(O)C(C(O)=O)=C1O YWJNJZBDYHRABW-UHFFFAOYSA-N 0.000 description 3
- MZGVIIXFGJCRDR-UHFFFAOYSA-N 4,6-dihydroxybenzene-1,3-dicarboxylic acid Chemical compound OC(=O)C1=CC(C(O)=O)=C(O)C=C1O MZGVIIXFGJCRDR-UHFFFAOYSA-N 0.000 description 3
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 3
- 229920000557 Nafion® Polymers 0.000 description 3
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 description 3
- 230000000996 additive effect Effects 0.000 description 3
- 239000003570 air Substances 0.000 description 3
- 230000008901 benefit Effects 0.000 description 3
- 238000005266 casting Methods 0.000 description 3
- 229920001577 copolymer Polymers 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 239000000945 filler Substances 0.000 description 3
- 229910052697 platinum Inorganic materials 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 238000009736 wetting Methods 0.000 description 3
- 229910003209 (NH4)3H(SeO4)2 Inorganic materials 0.000 description 2
- QPFMBZIOSGYJDE-UHFFFAOYSA-N 1,1,2,2-tetrachloroethane Chemical compound ClC(Cl)C(Cl)Cl QPFMBZIOSGYJDE-UHFFFAOYSA-N 0.000 description 2
- SQJQLYOMPSJVQS-UHFFFAOYSA-N 4-(4-carboxyphenyl)sulfonylbenzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1S(=O)(=O)C1=CC=C(C(O)=O)C=C1 SQJQLYOMPSJVQS-UHFFFAOYSA-N 0.000 description 2
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 2
- XUMBMVFBXHLACL-UHFFFAOYSA-N Melanin Chemical compound O=C1C(=O)C(C2=CNC3=C(C(C(=O)C4=C32)=O)C)=C2C4=CNC2=C1C XUMBMVFBXHLACL-UHFFFAOYSA-N 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- BPQQTUXANYXVAA-UHFFFAOYSA-N Orthosilicate Chemical compound [O-][Si]([O-])([O-])[O-] BPQQTUXANYXVAA-UHFFFAOYSA-N 0.000 description 2
- 229910019142 PO4 Inorganic materials 0.000 description 2
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 description 2
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 2
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 2
- 229910021536 Zeolite Inorganic materials 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- DZBUGLKDJFMEHC-UHFFFAOYSA-N acridine Chemical compound C1=CC=CC2=CC3=CC=CC=C3N=C21 DZBUGLKDJFMEHC-UHFFFAOYSA-N 0.000 description 2
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 2
- 239000003963 antioxidant agent Substances 0.000 description 2
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 description 2
- WZJYKHNJTSNBHV-UHFFFAOYSA-N benzo[h]quinoline Chemical compound C1=CN=C2C3=CC=CC=C3C=CC2=C1 WZJYKHNJTSNBHV-UHFFFAOYSA-N 0.000 description 2
- 239000003990 capacitor Substances 0.000 description 2
- 238000005341 cation exchange Methods 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 238000004132 cross linking Methods 0.000 description 2
- 150000001991 dicarboxylic acids Chemical class 0.000 description 2
- 238000009792 diffusion process Methods 0.000 description 2
- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 2
- KZTYYGOKRVBIMI-UHFFFAOYSA-N diphenyl sulfone Chemical compound C=1C=CC=CC=1S(=O)(=O)C1=CC=CC=C1 KZTYYGOKRVBIMI-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 239000000835 fiber Substances 0.000 description 2
- UQSQSQZYBQSBJZ-UHFFFAOYSA-N fluorosulfonic acid Chemical compound OS(F)(=O)=O UQSQSQZYBQSBJZ-UHFFFAOYSA-N 0.000 description 2
- 125000001072 heteroaryl group Chemical group 0.000 description 2
- 150000002430 hydrocarbons Chemical class 0.000 description 2
- 150000002431 hydrogen Chemical class 0.000 description 2
- AMWRITDGCCNYAT-UHFFFAOYSA-L hydroxy(oxo)manganese;manganese Chemical compound [Mn].O[Mn]=O.O[Mn]=O AMWRITDGCCNYAT-UHFFFAOYSA-L 0.000 description 2
- 239000012535 impurity Substances 0.000 description 2
- LVPMIMZXDYBCDF-UHFFFAOYSA-N isocinchomeronic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)N=C1 LVPMIMZXDYBCDF-UHFFFAOYSA-N 0.000 description 2
- 230000007774 longterm Effects 0.000 description 2
- 238000000691 measurement method Methods 0.000 description 2
- 230000007246 mechanism Effects 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- DFFZOPXDTCDZDP-UHFFFAOYSA-N naphthalene-1,5-dicarboxylic acid Chemical compound C1=CC=C2C(C(=O)O)=CC=CC2=C1C(O)=O DFFZOPXDTCDZDP-UHFFFAOYSA-N 0.000 description 2
- RXOHFPCZGPKIRD-UHFFFAOYSA-N naphthalene-2,6-dicarboxylic acid Chemical compound C1=C(C(O)=O)C=CC2=CC(C(=O)O)=CC=C21 RXOHFPCZGPKIRD-UHFFFAOYSA-N 0.000 description 2
- 239000003345 natural gas Substances 0.000 description 2
- 230000007935 neutral effect Effects 0.000 description 2
- 229910000510 noble metal Inorganic materials 0.000 description 2
- YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical compound C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 description 2
- 235000021317 phosphate Nutrition 0.000 description 2
- 229920002959 polymer blend Polymers 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- CYIDZMCFTVVTJO-UHFFFAOYSA-N pyromellitic acid Chemical compound OC(=O)C1=CC(C(O)=O)=C(C(O)=O)C=C1C(O)=O CYIDZMCFTVVTJO-UHFFFAOYSA-N 0.000 description 2
- 150000003254 radicals Chemical class 0.000 description 2
- 150000003839 salts Chemical group 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- HIFJUMGIHIZEPX-UHFFFAOYSA-N sulfuric acid;sulfur trioxide Chemical compound O=S(=O)=O.OS(O)(=O)=O HIFJUMGIHIZEPX-UHFFFAOYSA-N 0.000 description 2
- 239000010457 zeolite Substances 0.000 description 2
- QZHDEAJFRJCDMF-UHFFFAOYSA-M 1,1,2,2,3,3,4,4,5,5,6,6,6-tridecafluorohexane-1-sulfonate Chemical compound [O-]S(=O)(=O)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F QZHDEAJFRJCDMF-UHFFFAOYSA-M 0.000 description 1
- UZCCMCYUIFRHDR-UHFFFAOYSA-N 1,1,2,2,3,3,4,4,5,5,6,6,6-tridecafluorohexane-1-sulfonate triethylazanium Chemical compound CC[NH+](CC)CC.[O-]S(=O)(=O)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F UZCCMCYUIFRHDR-UHFFFAOYSA-N 0.000 description 1
- OWQPOVKKUWUEKE-UHFFFAOYSA-N 1,2,3-benzotriazine Chemical compound N1=NN=CC2=CC=CC=C21 OWQPOVKKUWUEKE-UHFFFAOYSA-N 0.000 description 1
- SLLFVLKNXABYGI-UHFFFAOYSA-N 1,2,3-benzoxadiazole Chemical compound C1=CC=C2ON=NC2=C1 SLLFVLKNXABYGI-UHFFFAOYSA-N 0.000 description 1
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 1
- VMLKTERJLVWEJJ-UHFFFAOYSA-N 1,5-naphthyridine Chemical compound C1=CC=NC2=CC=CN=C21 VMLKTERJLVWEJJ-UHFFFAOYSA-N 0.000 description 1
- VEPOHXYIFQMVHW-XOZOLZJESA-N 2,3-dihydroxybutanedioic acid (2S,3S)-3,4-dimethyl-2-phenylmorpholine Chemical compound OC(C(O)C(O)=O)C(O)=O.C[C@H]1[C@@H](OCCN1C)c1ccccc1 VEPOHXYIFQMVHW-XOZOLZJESA-N 0.000 description 1
- GRFXXWWBAWFSRF-UHFFFAOYSA-N 2-nitrosobutane Chemical compound CCC(C)N=O GRFXXWWBAWFSRF-UHFFFAOYSA-N 0.000 description 1
- MILSYCKGLDDVLM-UHFFFAOYSA-N 2-phenylpropan-2-ylbenzene Chemical compound C=1C=CC=CC=1C(C)(C)C1=CC=CC=C1 MILSYCKGLDDVLM-UHFFFAOYSA-N 0.000 description 1
- KTWGCHVHXBORDH-UHFFFAOYSA-N 4,6-diphenylbenzene-1,3-dicarboxylic acid Chemical compound OC(=O)C1=CC(C(O)=O)=C(C=2C=CC=CC=2)C=C1C1=CC=CC=C1 KTWGCHVHXBORDH-UHFFFAOYSA-N 0.000 description 1
- SBBQDUFLZGOASY-OWOJBTEDSA-N 4-[(e)-2-(4-carboxyphenyl)ethenyl]benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1\C=C\C1=CC=C(C(O)=O)C=C1 SBBQDUFLZGOASY-OWOJBTEDSA-N 0.000 description 1
- LQEZHWGJSWHXPJ-UHFFFAOYSA-N 5-(4-carboxyphenyl)benzene-1,3-dicarboxylic acid Chemical compound C1=CC(C(=O)O)=CC=C1C1=CC(C(O)=O)=CC(C(O)=O)=C1 LQEZHWGJSWHXPJ-UHFFFAOYSA-N 0.000 description 1
- KDCGOANMDULRCW-UHFFFAOYSA-N 7H-purine Chemical compound N1=CNC2=NC=NC2=C1 KDCGOANMDULRCW-UHFFFAOYSA-N 0.000 description 1
- 229910018072 Al 2 O 3 Inorganic materials 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- ROFVEXUMMXZLPA-UHFFFAOYSA-N Bipyridyl Chemical compound N1=CC=CC=C1C1=CC=CC=N1 ROFVEXUMMXZLPA-UHFFFAOYSA-N 0.000 description 1
- MZULZTHLIMEHIY-UHFFFAOYSA-N C1(=C(C(=CC=C1)C(=O)O)C(=O)O)C1=C(C(=CC=C1)C(=O)O)C(=O)O.C=1(C(=CC=C2C(=C(C=CC12)C(=O)O)C(=O)O)C(=O)O)C(=O)O Chemical compound C1(=C(C(=CC=C1)C(=O)O)C(=O)O)C1=C(C(=CC=C1)C(=O)O)C(=O)O.C=1(C(=CC=C2C(=C(C=CC12)C(=O)O)C(=O)O)C(=O)O)C(=O)O MZULZTHLIMEHIY-UHFFFAOYSA-N 0.000 description 1
- GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- 239000002000 Electrolyte additive Substances 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 1
- 229920008285 Poly(ether ketone) PEK Polymers 0.000 description 1
- 229920000388 Polyphosphate Polymers 0.000 description 1
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 1
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 description 1
- 229910018287 SbF 5 Inorganic materials 0.000 description 1
- 241001233279 Scalopus Species 0.000 description 1
- 229910006404 SnO 2 Inorganic materials 0.000 description 1
- DPOPAJRDYZGTIR-UHFFFAOYSA-N Tetrazine Chemical compound C1=CN=NN=N1 DPOPAJRDYZGTIR-UHFFFAOYSA-N 0.000 description 1
- DGEZNRSVGBDHLK-UHFFFAOYSA-N [1,10]phenanthroline Chemical compound C1=CN=C2C3=NC=CC=C3C=CC2=C1 DGEZNRSVGBDHLK-UHFFFAOYSA-N 0.000 description 1
- 150000003973 alkyl amines Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 239000000908 ammonium hydroxide Substances 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 150000004982 aromatic amines Chemical class 0.000 description 1
- SQTGBVURPMTXBT-UHFFFAOYSA-N azanium;1,1,2,2,3,3,4,4,4-nonafluorobutane-1-sulfonate Chemical compound [NH4+].[O-]S(=O)(=O)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F SQTGBVURPMTXBT-UHFFFAOYSA-N 0.000 description 1
- UGEFCGLPIFEPMQ-UHFFFAOYSA-N azanium;1,1,2,2,3,3,4,4,5,5,6,6,6-tridecafluorohexane-1-sulfonate Chemical compound N.OS(=O)(=O)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F UGEFCGLPIFEPMQ-UHFFFAOYSA-N 0.000 description 1
- BMWDUGHMODRTLU-UHFFFAOYSA-N azanium;trifluoromethanesulfonate Chemical compound [NH4+].[O-]S(=O)(=O)C(F)(F)F BMWDUGHMODRTLU-UHFFFAOYSA-N 0.000 description 1
- 239000003637 basic solution Substances 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- SCJFJWNHJWAJSX-UHFFFAOYSA-N benzaldehyde N-(2,2-dimethylpropylidene)hydroxylamine Chemical compound CC(C)(C)C=NO.O=CC1=CC=CC=C1 SCJFJWNHJWAJSX-UHFFFAOYSA-N 0.000 description 1
- BTZVACANDIHKJX-UHFFFAOYSA-N benzo[g]pteridine Chemical compound N1=CN=CC2=NC3=CC=CC=C3N=C21 BTZVACANDIHKJX-UHFFFAOYSA-N 0.000 description 1
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 1
- 239000012965 benzophenone Substances 0.000 description 1
- QRUDEWIWKLJBPS-UHFFFAOYSA-N benzotriazole Chemical compound C1=CC=C2N[N][N]C2=C1 QRUDEWIWKLJBPS-UHFFFAOYSA-N 0.000 description 1
- 239000012964 benzotriazole Substances 0.000 description 1
- 230000005250 beta ray Effects 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 125000002529 biphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C12)* 0.000 description 1
- 229920001400 block copolymer Polymers 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 125000000837 carbohydrate group Chemical group 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002091 carbon monoxide Inorganic materials 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 230000006727 cell loss Effects 0.000 description 1
- 239000000919 ceramic Substances 0.000 description 1
- VGNIIAPVRLMILS-UHFFFAOYSA-M cesium;1,1,2,2,3,3,4,4,4-nonafluorobutane-1-sulfonate Chemical compound [Cs+].[O-]S(=O)(=O)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F VGNIIAPVRLMILS-UHFFFAOYSA-M 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 229910000428 cobalt oxide Inorganic materials 0.000 description 1
- IVMYJDGYRUAWML-UHFFFAOYSA-N cobalt(ii) oxide Chemical compound [Co]=O IVMYJDGYRUAWML-UHFFFAOYSA-N 0.000 description 1
- 239000011231 conductive filler Substances 0.000 description 1
- 239000004020 conductor Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- UFULAYFCSOUIOV-UHFFFAOYSA-N cysteamine Chemical compound NCCS UFULAYFCSOUIOV-UHFFFAOYSA-N 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- CZZYITDELCSZES-UHFFFAOYSA-N diphenylmethane Chemical compound C=1C=CC=CC=1CC1=CC=CC=C1 CZZYITDELCSZES-UHFFFAOYSA-N 0.000 description 1
- 238000003487 electrochemical reaction Methods 0.000 description 1
- 230000005518 electrochemistry Effects 0.000 description 1
- 238000005868 electrolysis reaction Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000001125 extrusion Methods 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 239000002737 fuel gas Substances 0.000 description 1
- 239000003365 glass fiber Substances 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 230000020169 heat generation Effects 0.000 description 1
- 230000036571 hydration Effects 0.000 description 1
- 238000006703 hydration reaction Methods 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- QWPPOHNGKGFGJK-UHFFFAOYSA-N hypochlorous acid Chemical compound ClO QWPPOHNGKGFGJK-UHFFFAOYSA-N 0.000 description 1
- 238000001566 impedance spectroscopy Methods 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- HOBCFUWDNJPFHB-UHFFFAOYSA-N indolizine Chemical compound C1=CC=CN2C=CC=C21 HOBCFUWDNJPFHB-UHFFFAOYSA-N 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 229910000464 lead oxide Inorganic materials 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- FEDFHMISXKDOJI-UHFFFAOYSA-M lithium;1,1,2,2,3,3,4,4,4-nonafluorobutane-1-sulfonate Chemical compound [Li+].[O-]S(=O)(=O)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F FEDFHMISXKDOJI-UHFFFAOYSA-M 0.000 description 1
- VAXNCPZUCRECEW-UHFFFAOYSA-M lithium;1,1,2,2,3,3,4,4,5,5,6,6,6-tridecafluorohexane-1-sulfonate Chemical compound [Li+].[O-]S(=O)(=O)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F VAXNCPZUCRECEW-UHFFFAOYSA-M 0.000 description 1
- MCVFFRWZNYZUIJ-UHFFFAOYSA-M lithium;trifluoromethanesulfonate Chemical compound [Li+].[O-]S(=O)(=O)C(F)(F)F MCVFFRWZNYZUIJ-UHFFFAOYSA-M 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 229960003151 mercaptamine Drugs 0.000 description 1
- 150000001247 metal acetylides Chemical class 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 229910052901 montmorillonite Inorganic materials 0.000 description 1
- 229910052680 mordenite Inorganic materials 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 229910052674 natrolite Inorganic materials 0.000 description 1
- 229910000480 nickel oxide Inorganic materials 0.000 description 1
- NLRKCXQQSUWLCH-UHFFFAOYSA-N nitrosobenzene Chemical compound O=NC1=CC=CC=C1 NLRKCXQQSUWLCH-UHFFFAOYSA-N 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- YEXPOXQUZXUXJW-UHFFFAOYSA-N oxolead Chemical compound [Pb]=O YEXPOXQUZXUXJW-UHFFFAOYSA-N 0.000 description 1
- GNRSAWUEBMWBQH-UHFFFAOYSA-N oxonickel Chemical compound [Ni]=O GNRSAWUEBMWBQH-UHFFFAOYSA-N 0.000 description 1
- 125000005010 perfluoroalkyl group Chemical group 0.000 description 1
- 230000000737 periodic effect Effects 0.000 description 1
- 230000035699 permeability Effects 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- AQSJGOWTSHOLKH-UHFFFAOYSA-N phosphite(3-) Chemical class [O-]P([O-])[O-] AQSJGOWTSHOLKH-UHFFFAOYSA-N 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000003880 polar aprotic solvent Substances 0.000 description 1
- 229920001643 poly(ether ketone) Polymers 0.000 description 1
- 229920002577 polybenzoxazole Polymers 0.000 description 1
- 238000012667 polymer degradation Methods 0.000 description 1
- 229920005594 polymer fiber Polymers 0.000 description 1
- 239000001205 polyphosphate Substances 0.000 description 1
- 235000011176 polyphosphates Nutrition 0.000 description 1
- LVTHXRLARFLXNR-UHFFFAOYSA-M potassium;1,1,2,2,3,3,4,4,4-nonafluorobutane-1-sulfonate Chemical compound [K+].[O-]S(=O)(=O)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F LVTHXRLARFLXNR-UHFFFAOYSA-M 0.000 description 1
- RSCGQEBKFSGWJT-UHFFFAOYSA-M potassium;1,1,2,2,3,3,4,4,5,5,6,6,6-tridecafluorohexane-1-sulfonate Chemical compound [K+].[O-]S(=O)(=O)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F RSCGQEBKFSGWJT-UHFFFAOYSA-M 0.000 description 1
- GLGXXYFYZWQGEL-UHFFFAOYSA-M potassium;trifluoromethanesulfonate Chemical compound [K+].[O-]S(=O)(=O)C(F)(F)F GLGXXYFYZWQGEL-UHFFFAOYSA-M 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- CPNGPNLZQNNVQM-UHFFFAOYSA-N pteridine Chemical compound N1=CN=CC2=NC=CN=C21 CPNGPNLZQNNVQM-UHFFFAOYSA-N 0.000 description 1
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 description 1
- 238000011002 quantification Methods 0.000 description 1
- JWVCLYRUEFBMGU-UHFFFAOYSA-N quinazoline Chemical compound N1=CN=CC2=CC=CC=C21 JWVCLYRUEFBMGU-UHFFFAOYSA-N 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 229920005604 random copolymer Polymers 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 229940082569 selenite Drugs 0.000 description 1
- MCAHWIHFGHIESP-UHFFFAOYSA-L selenite(2-) Chemical compound [O-][Se]([O-])=O MCAHWIHFGHIESP-UHFFFAOYSA-L 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 150000004760 silicates Chemical class 0.000 description 1
- 229910052665 sodalite Inorganic materials 0.000 description 1
- QBJDFZSOZNDVDE-UHFFFAOYSA-M sodium;1,1,2,2,3,3,4,4,4-nonafluorobutane-1-sulfonate Chemical compound [Na+].[O-]S(=O)(=O)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F QBJDFZSOZNDVDE-UHFFFAOYSA-M 0.000 description 1
- WXNIEINRHBIHRE-UHFFFAOYSA-M sodium;1,1,2,2,3,3,4,4,5,5,6,6,6-tridecafluorohexane-1-sulfonate Chemical compound [Na+].[O-]S(=O)(=O)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F WXNIEINRHBIHRE-UHFFFAOYSA-M 0.000 description 1
- XGPOMXSYOKFBHS-UHFFFAOYSA-M sodium;trifluoromethanesulfonate Chemical compound [Na+].[O-]S(=O)(=O)C(F)(F)F XGPOMXSYOKFBHS-UHFFFAOYSA-M 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 238000003892 spreading Methods 0.000 description 1
- 230000007480 spreading Effects 0.000 description 1
- 230000006641 stabilisation Effects 0.000 description 1
- 238000011105 stabilization Methods 0.000 description 1
- 238000005728 strengthening Methods 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 150000008053 sultones Chemical class 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- BFKJFAAPBSQJPD-UHFFFAOYSA-N tetrafluoroethene Chemical group FC(F)=C(F)F BFKJFAAPBSQJPD-UHFFFAOYSA-N 0.000 description 1
- 238000004448 titration Methods 0.000 description 1
- 230000007723 transport mechanism Effects 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 description 1
- 238000011144 upstream manufacturing Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J5/00—Manufacture of articles or shaped materials containing macromolecular substances
- C08J5/20—Manufacture of shaped structures of ion-exchange resins
- C08J5/22—Films, membranes or diaphragms
- C08J5/2206—Films, membranes or diaphragms based on organic and/or inorganic macromolecular compounds
- C08J5/2218—Synthetic macromolecular compounds
- C08J5/2256—Synthetic macromolecular compounds based on macromolecular compounds obtained by reactions other than those involving carbon-to-carbon bonds, e.g. obtained by polycondensation
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J5/00—Manufacture of articles or shaped materials containing macromolecular substances
- C08J5/20—Manufacture of shaped structures of ion-exchange resins
- C08J5/22—Films, membranes or diaphragms
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D71/00—Semi-permeable membranes for separation processes or apparatus characterised by the material; Manufacturing processes specially adapted therefor
- B01D71/06—Organic material
- B01D71/58—Other polymers having nitrogen in the main chain, with or without oxygen or carbon only
- B01D71/62—Polycondensates having nitrogen-containing heterocyclic rings in the main chain
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D71/00—Semi-permeable membranes for separation processes or apparatus characterised by the material; Manufacturing processes specially adapted therefor
- B01D71/06—Organic material
- B01D71/76—Macromolecular material not specifically provided for in a single one of groups B01D71/08 - B01D71/74
- B01D71/82—Macromolecular material not specifically provided for in a single one of groups B01D71/08 - B01D71/74 characterised by the presence of specified groups, e.g. introduced by chemical after-treatment
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
- C08G73/06—Polycondensates having nitrogen-containing heterocyclic rings in the main chain of the macromolecule
- C08G73/0605—Polycondensates containing five-membered rings, not condensed with other rings, with nitrogen atoms as the only ring hetero atoms
- C08G73/0616—Polycondensates containing five-membered rings, not condensed with other rings, with nitrogen atoms as the only ring hetero atoms with only two nitrogen atoms in the ring
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
- C08G73/06—Polycondensates having nitrogen-containing heterocyclic rings in the main chain of the macromolecule
- C08G73/0622—Polycondensates containing six-membered rings, not condensed with other rings, with nitrogen atoms as the only ring hetero atoms
- C08G73/0627—Polycondensates containing six-membered rings, not condensed with other rings, with nitrogen atoms as the only ring hetero atoms with only one nitrogen atom in the ring
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
- C08G73/06—Polycondensates having nitrogen-containing heterocyclic rings in the main chain of the macromolecule
- C08G73/0622—Polycondensates containing six-membered rings, not condensed with other rings, with nitrogen atoms as the only ring hetero atoms
- C08G73/0633—Polycondensates containing six-membered rings, not condensed with other rings, with nitrogen atoms as the only ring hetero atoms with only two nitrogen atoms in the ring
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
- C08G73/06—Polycondensates having nitrogen-containing heterocyclic rings in the main chain of the macromolecule
- C08G73/08—Polyhydrazides; Polytriazoles; Polyaminotriazoles; Polyoxadiazoles
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
- C08G73/06—Polycondensates having nitrogen-containing heterocyclic rings in the main chain of the macromolecule
- C08G73/18—Polybenzimidazoles
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
- C08G73/06—Polycondensates having nitrogen-containing heterocyclic rings in the main chain of the macromolecule
- C08G73/22—Polybenzoxazoles
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J3/00—Processes of treating or compounding macromolecular substances
- C08J3/02—Making solutions, dispersions, lattices or gels by other methods than by solution, emulsion or suspension polymerisation techniques
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01M—PROCESSES OR MEANS, e.g. BATTERIES, FOR THE DIRECT CONVERSION OF CHEMICAL ENERGY INTO ELECTRICAL ENERGY
- H01M8/00—Fuel cells; Manufacture thereof
- H01M8/10—Fuel cells with solid electrolytes
- H01M8/1004—Fuel cells with solid electrolytes characterised by membrane-electrode assemblies [MEA]
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01M—PROCESSES OR MEANS, e.g. BATTERIES, FOR THE DIRECT CONVERSION OF CHEMICAL ENERGY INTO ELECTRICAL ENERGY
- H01M8/00—Fuel cells; Manufacture thereof
- H01M8/10—Fuel cells with solid electrolytes
- H01M8/1016—Fuel cells with solid electrolytes characterised by the electrolyte material
- H01M8/1018—Polymeric electrolyte materials
- H01M8/102—Polymeric electrolyte materials characterised by the chemical structure of the main chain of the ion-conducting polymer
- H01M8/1027—Polymeric electrolyte materials characterised by the chemical structure of the main chain of the ion-conducting polymer having carbon, oxygen and other atoms, e.g. sulfonated polyethersulfones [S-PES]
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01M—PROCESSES OR MEANS, e.g. BATTERIES, FOR THE DIRECT CONVERSION OF CHEMICAL ENERGY INTO ELECTRICAL ENERGY
- H01M8/00—Fuel cells; Manufacture thereof
- H01M8/10—Fuel cells with solid electrolytes
- H01M8/1016—Fuel cells with solid electrolytes characterised by the electrolyte material
- H01M8/1018—Polymeric electrolyte materials
- H01M8/102—Polymeric electrolyte materials characterised by the chemical structure of the main chain of the ion-conducting polymer
- H01M8/103—Polymeric electrolyte materials characterised by the chemical structure of the main chain of the ion-conducting polymer having nitrogen, e.g. sulfonated polybenzimidazoles [S-PBI], polybenzimidazoles with phosphoric acid, sulfonated polyamides [S-PA] or sulfonated polyphosphazenes [S-PPh]
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01M—PROCESSES OR MEANS, e.g. BATTERIES, FOR THE DIRECT CONVERSION OF CHEMICAL ENERGY INTO ELECTRICAL ENERGY
- H01M8/00—Fuel cells; Manufacture thereof
- H01M8/10—Fuel cells with solid electrolytes
- H01M8/1016—Fuel cells with solid electrolytes characterised by the electrolyte material
- H01M8/1018—Polymeric electrolyte materials
- H01M8/1041—Polymer electrolyte composites, mixtures or blends
- H01M8/1046—Mixtures of at least one polymer and at least one additive
- H01M8/1048—Ion-conducting additives, e.g. ion-conducting particles, heteropolyacids, metal phosphate or polybenzimidazole with phosphoric acid
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01M—PROCESSES OR MEANS, e.g. BATTERIES, FOR THE DIRECT CONVERSION OF CHEMICAL ENERGY INTO ELECTRICAL ENERGY
- H01M8/00—Fuel cells; Manufacture thereof
- H01M8/10—Fuel cells with solid electrolytes
- H01M8/1016—Fuel cells with solid electrolytes characterised by the electrolyte material
- H01M8/1018—Polymeric electrolyte materials
- H01M8/1067—Polymeric electrolyte materials characterised by their physical properties, e.g. porosity, ionic conductivity or thickness
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01M—PROCESSES OR MEANS, e.g. BATTERIES, FOR THE DIRECT CONVERSION OF CHEMICAL ENERGY INTO ELECTRICAL ENERGY
- H01M8/00—Fuel cells; Manufacture thereof
- H01M8/10—Fuel cells with solid electrolytes
- H01M8/1016—Fuel cells with solid electrolytes characterised by the electrolyte material
- H01M8/1018—Polymeric electrolyte materials
- H01M8/1069—Polymeric electrolyte materials characterised by the manufacturing processes
- H01M8/1072—Polymeric electrolyte materials characterised by the manufacturing processes by chemical reactions, e.g. insitu polymerisation or insitu crosslinking
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J2379/00—Characterised by the use of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing nitrogen with or without oxygen, or carbon only, not provided for in groups C08J2361/00 - C08J2377/00
- C08J2379/04—Polycondensates having nitrogen-containing heterocyclic rings in the main chain; Polyhydrazides; Polyamide acids or similar polyimide precursors
- C08J2379/06—Polyhydrazides; Polytriazoles; Polyamino-triazoles; Polyoxadiazoles
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
- Y02E60/00—Enabling technologies; Technologies with a potential or indirect contribution to GHG emissions mitigation
- Y02E60/30—Hydrogen technology
- Y02E60/50—Fuel cells
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P70/00—Climate change mitigation technologies in the production process for final industrial or consumer products
- Y02P70/50—Manufacturing or production processes characterised by the final manufactured product
Landscapes
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Manufacturing & Machinery (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Sustainable Development (AREA)
- Sustainable Energy (AREA)
- Electrochemistry (AREA)
- Crystallography & Structural Chemistry (AREA)
- Materials Engineering (AREA)
- Composite Materials (AREA)
- Inorganic Chemistry (AREA)
- Dispersion Chemistry (AREA)
- Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
- Manufacture Of Macromolecular Shaped Articles (AREA)
- Conductive Materials (AREA)
- Fuel Cell (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Silicon Polymers (AREA)
Abstract
Description
A)ポリリン酸/スルホン化剤混合物において、一以上の芳香族テトラアミノ化合物を、1つのカルボン酸モノマー当たり少なくとも2個の酸基を有する一以上の芳香族カルボン酸またはそのエステルと混合して、または一以上の芳香族および/または複素環式芳香族ジアミノカルボン酸を混合して、溶液および/または分散液を形成し、
B)段階A)の混合物を用いた層を支持体または電極に塗布し、
C)350℃以下、好ましくは280℃以下の温度で不活性ガス下で段階B)で得られるシート状構造物/層を加熱して、ポリアゾールポリマーを形成し、
D)好ましくは自立するまで、段階C)で形成した膜を処理する段階
を有する方法によって得られるプロトン伝導性ポリマー膜を提供するものである。
基Ar1は、同一または異なるものであり、それぞれ、単環若しくは多環であってもよい2価の芳香族または複素環式芳香族基であり、
基Ar2は、同一または異なるものであり、それぞれ、単環若しくは多環であってもよい2価若しくは3価の芳香族または複素環式芳香族基であり、
基Ar3は、同一または異なるものであり、それぞれ、単環若しくは多環であってもよい3価の芳香族または複素環式芳香族基であり、
基Ar4は、同一または異なるものであり、それぞれ、単環若しくは多環であってもよい3価の芳香族または複素環式芳香族基であり、
基Ar5は、同一または異なるものであり、それぞれ、単環若しくは多環であってもよい4価の芳香族または複素環式芳香族基であり、
基Ar6は、同一または異なるものであり、それぞれ、単環若しくは多環であってもよい2価の芳香族または複素環式芳香族基であり、
基Ar7は、同一または異なるものであり、それぞれ、単環若しくは多環であってもよい2価の芳香族または複素環式芳香族基であり、
基Ar8は、同一または異なるものであり、それぞれ、単環若しくは多環であってもよい3価の芳香族または複素環式芳香族基であり、
基Ar9は、同一または異なるものであり、それぞれ、単環若しくは多環であってもよい2価若しくは3価若しくは4価の芳香族または複素環式芳香族基であり、
基Ar10は、同一または異なるものであり、それぞれ、単環若しくは多環であってもよい2価若しくは3価の芳香族または複素環式芳香族基であり、
基Ar11は、同一または異なるものであり、それぞれ、単環若しくは多環であってもよい2価の芳香族または複素環式芳香族基であり、
基Xは、同一または異なるものであり、それぞれ、水素原子、1〜20炭素原子を有する基、好ましくは分岐鎖または枝なし鎖のアルキル若しくはアルコキシ基、またはアリール基を追加の基として有する酸素、硫黄またはアミノ基であり、
基Rは、同一または異なるものであり、それぞれ、水素、アルキル基または芳香族基であり、ならびに
n、mは、それぞれ、10以上、好ましくは100以上の整数である、
の繰り返しアゾール単位を有し、硫黄含量(元素分析によって測定)が2〜20重量%、特に4〜10重量%である。
Zr3(PO4)4、Zr(HPO4)2、HZr2(PO4)3、UO2PO4・3H2O、H8UO2PO4、Ce(HPO4)2、Ti(HPO4)2、KH2PO4、NaH2PO4、LiH2PO4、NH4H2PO4、CsH2PO4、CaHPO4、MgHPO4、HSbP2O8、HSb3P2O14、H5Sb5P2O20等のリン酸塩、
H3PW12O40・nH2O(n=21〜29)、H3SiW12O40・nH2O(n=21〜29)、HxWO3、HSbWO6、H3PMo12O40、H2Sb4O11、HTaWO6、HNbO3、HTiNbO5、HTiTaO5、HSbTeO6、H5Ti4O9、HSbO3、H2MoO4等のポリ酸、
(NH4)3H(SeO4)2、UO2AsO4、(NH4)3H(SeO4)2、KH2AsO4、Cs3H(SeO4)2、Rb3H(SeO4)2等の亜セレン酸塩及びヒ化物、
Al2O3、Sb2O5、ThO2、SnO2、ZrO2、MoO3等の酸化物、
ゼオライト、ゼオライト(NH4+)、層状珪酸塩、立体網状珪酸塩、H−ソーダ沸石、H−モルデン沸石、NH4−アナルシン(analcine)、NH4−方ソーダ石、NH4−没食子酸塩、H−モンモリロナイト等のケイ酸塩、
HClO4、SbF5等の酸、
カーバイド、特にSiC、Si3N4、繊維、特にガラスファイバー、ガラス粉末および/またはポリマー繊維、好ましくはポリアゾールを用いた繊維等の充填剤。
IECの測定方法
膜の伝導性は、イオン交換能(IEC)として表わされる酸基の含量によってかなり異なる。イオン交換能を測定するために、3cm直径の試料を打ち抜いて、100mlの水の入ったガラス製のビーカーに入れる。遊離した酸を、0.1M NaOHで滴定する。次に、この試料を取り出して、過剰の水を軽くたたいて除き、試料を160℃で4時間乾燥する。さらに、乾燥重量、m0、を、0.1mgの精度で重量測定法で測定する。次に、イオン交換能を、下記式によって、最初の滴定の終点までの0.1M NaOHの消費量、V1(ml)、及び乾燥重量、m0(mg)から算出する。
比導電率は、白金電極(ワイヤ、0.25mm直径)を用いた低電圧方式で4ポール配置した(in a 4-pole arrangement)インピーダンス分光分析(impedance spectroscopy)によって測定する。集電電極間の距離は2cmである。得られるスペクトルを、オーム抵抗及びキャパシターを平行に配置してなる簡単なモデルを用いて評価する。リン酸でドープした膜の試料断面を、試料を載せる直前に測定する。温度依存性を測定するために、測定セルをオーブン中で所望の温度にし、さらに試料のすぐそばに位置したPt−100抵抗温度計によって温度を調節する。温度が到達したら、試料をこの温度に10分間維持した後、測定を開始する。
in situでスルホン化されたPBI膜の調製用のストック溶液
938.6gのポリリン酸(83.4±0.5%のP2O5)を、窒素導入口及び排出口ならびに機械的スターラーを備えた1.5Lのフラスコ内の26.948gのイソフタル酸及び34.74gの3,3’,4,4’−テトラアミノビフェニルの混合物に添加した。この混合物を、120℃で2時間、150℃で3時間及び180℃で2時間、加熱した。次に、この反応溶液を、220℃に加熱して、14時間攪拌した。得られたPPAにおける5%濃度のPBI溶液(5% strength PBI solution in PPA)を、室温まで冷却し、以下のスルホン化PBI膜を製造するのに使用した。
22.34gの85%濃度のリン酸及び1.66gの96%濃度の硫酸を、30分かけて220℃で、113.6%のPPAにおける上記5%濃度のPBIストック溶液100gに添加した。この溶液を220℃でさらに4時間攪拌した。得られたPPAにおけるスルホン化PBI溶液を、予め加熱しておいたドクターブレードによって220℃でガラス板に塗布した(381μm)。透明な膜が得られた。次に、この膜を室温で1日放置して、自立した膜を得た。
17.24gの85%濃度のリン酸及び3.314gの96%濃度の硫酸を、30分かけて220℃で、113.6%のPPAにおける上記5%濃度のPBIストック溶液100gに添加した。この溶液を220℃でさらに4時間攪拌した。得られたPPAにおけるスルホン化PBI溶液を、予め加熱しておいたドクターブレードによって220℃でガラス板に塗布した(381μm)。透明な膜が得られた。次に、この膜を室温で1日放置した。
24.76gの85%濃度のリン酸及び4.97gの96%濃度の硫酸を、30分かけて220℃で、113.6%のPPAにおける上記5%濃度のPBIストック溶液100gに添加した。この溶液を220℃でさらに4時間攪拌した。得られたPPAにおけるスルホン化PBI溶液を、予め加熱しておいたドクターブレードによって220℃でガラス板に塗布した(381μm)。透明な膜が得られた。次に、この膜を室温で1日放置した。
38.89gの85%濃度のリン酸及び6.6288gの96%濃度の硫酸を、30分かけて220℃で、113.6%のPPAにおける上記5%濃度のPBIストック溶液100gに添加した。この溶液を220℃でさらに4時間攪拌した。得られた105.1%濃度のPPAにおけるスルホン化PBI溶液を、予め加熱しておいたドクターブレードによって220℃でガラス板に塗布した(381μm)。透明な膜が得られた。次に、この膜を室温で1日放置した。
41.22gの85%濃度のリン酸、19.333gの115%濃度のポリリン酸及び9.943gの96%濃度の硫酸を、30分かけて220℃で、113.6%のPPAにおける上記5%濃度のPBIストック溶液100gに添加した。この溶液を220℃でさらに4時間攪拌した。得られたPPAにおけるスルホン化PBI溶液を、予め加熱しておいたドクターブレードによって220℃でガラス板に塗布した(381μm)。透明な膜が得られた。次に、この膜を室温で1日放置した。
Claims (19)
- スルホン化ポリアゾールを用いたものであり、かつ
A)ポリリン酸/スルホン化剤混合物において、一以上の芳香族テトラアミノ化合物を、1つのカルボン酸モノマー当たり少なくとも2個の酸基を有する一以上の芳香族カルボン酸またはそのエステルと混合して、または一以上の芳香族および/または複素環式芳香族ジアミノカルボン酸を混合して、溶液および/または分散液を形成し、
B)段階A)の混合物を用いた層を支持体または電極に塗布し、
C)350℃以下、好ましくは280℃以下の温度で不活性ガス下で段階B)で得られるシート状構造物/層を加熱して、ポリアゾールポリマーを形成し、
D)段階C)で形成した膜を処理する段階
を有する方法によって得られるプロトン伝導性ポリマー膜。 - 使用される芳香族テトラアミノ化合物は、3,3’,4,4’−テトラアミノビフェニル、2,3,5,6−テトラアミノピリジン、1,2,4,5−テトラアミノベンゼン、ビス(3,4−ジアミノフェニル)スルホン、ビス(3,4−ジアミノフェニル)エーテル、3,3’,4,4’−テトラアミノベンゾフェノン、3,3’,4,4’−テトラアミノジフェニルメタン及び3,3’,4,4’−テトラアミノジフェニルジメチルメタンである、請求項1に記載の膜。
- 使用される芳香族ジカルボン酸は、イソフタル酸、テレフタル酸、フタル酸、5−ヒドロキシイソフタル酸、4−ヒドロキシイソフタル酸、2−ヒドロキシテレフタル酸、5−アミノイソフタル酸、5−N,N−ジメチルアミノイソフタル酸、5−N,N−ジエチルアミノイソフタル酸、2,5−ジヒドロキシテレフタル酸、2,5−ジヒドロキシイソフタル酸、2,3−ジヒドロキシイソフタル酸、2,3−ジヒドロキシフタル酸、2,4−ジヒドロキシフタル酸、3,4−ジヒドロキシ-フタル酸、3−フルオロフタル酸、5−フルオロイソフタル酸、2−フルオロテレフタル酸、テトラフルオロフタル酸、テトラフルオロイソフタル酸、テトラフルオロテレフタル酸、1,4−ナフタレンジカルボン酸、1,5−ナフタレンジカルボン酸、2,6−ナフタレンジカルボン酸、2,7−ナフタレンジカルボン酸、ジフェン酸、1,8−ジヒドロキシナフタレン−3,6−ジカルボン酸、ビス(4−カルボキシフェニル)エーテル、ベンゾフェノン−4,4’−ジカルボン酸、ビス(4−ジカルボキシフェニル)スルホン、ビフェニル−4,4’−ジカルボン酸、4−トリフルオロメチルフタル酸、2,2−ビス(4−カルボキシフェニル)ヘキサフルオロプロパン、4,4’−スチルベンジカルボン酸、4−カルボキシ桂皮酸、またはこれらのC1−C20−アルキルエステル若しくはC5−C12−アリールエステル、またはこれらの酸無水物若しくは酸塩化物である、請求項1に記載の膜。
- 使用される芳香族カルボン酸は、トリカルボン酸、テトラカルボン酸またはこれらのC1−C20−アルキルエステル若しくはC5−C12−アリールエステルまたはこれらの酸無水物またはこれらの酸塩化物、好ましくは1,3,5−ベンゼントリカルボン酸(トリメシン酸);1,2,4−ベンゼントリカルボン酸(トリメリット酸);(2−カルボキシフェニル)イミノ2酢酸、3,5,3’−ビフェニルトリカルボン酸;3,5,4’−ビフェニルトリカルボン酸および/または2,4,6−ピリジントリカルボン酸である、請求項1に記載の膜。
- 使用される芳香族カルボン酸は、テトラカルボン酸、これらのC1−C20−アルキルエステル若しくはC5−C12−アリールエステルまたはこれらの酸無水物またはこれらの酸塩化物、好ましくはベンゼン−1,2,4,5−テトラカルボン酸;ナフタレン−1,4,5,8−テトラカルボン酸、3,5,3’,5’−ビフェニルテトラカルボン酸;ベンゾフェノンテトラカルボン酸、3,3’,4,4’−ビフェニルテトラカルボン酸、2,2’,3,3’−ビフェニルテトラカルボン酸、1,2,5,6−ナフタレンテトラカルボン酸、1,4,5,8−ナフタレンテトラカルボン酸である、請求項1に記載の膜。
- (使用されるジカルボン酸に対する)トリカルボン酸またはテトラカルボン酸の含量が、0〜30モル%、好ましくは0.1〜20モル%、特に0.5〜10モル%である、請求項4に記載の膜。
- 使用される複素環式芳香族カルボン酸は、少なくとも1個の窒素、酸素、硫黄またはリン原子が芳香族環中に存在する複素環式芳香族ジカルボン酸及びトリカルボン酸及びテトラカルボン酸、好ましくはピリジン−2,5−ジカルボン酸、ピリジン−3,5−ジカルボン酸、ピリジン−2,6−ジカルボン酸、ピリジン−2,4−ジカルボン酸、4−フェニル−2,5−ピリジンジカルボン酸、3,5−ピラゾールジカルボン酸、2,6−ピリミジンジカルボン酸、2,5−ピラジンジカルボン酸、2,4,6−ピリジントリカルボン酸、ベンズイミダゾール−5,6−ジカルボン酸、及びこれらのC1−C20−アルキルエステル若しくはC5−C12−アリールエステル、またはこれらの酸無水物またはこれらの酸塩化物である、請求項1に記載の膜。
- 段階A)で使用されるスルホン化剤は、i)濃硫酸(>95%)、ii)クロロスルホン酸、iii)SO3とルイス塩基または他の有機成分との複合体、iv)アシルまたはアルキル硫酸塩、v)有機スルホン酸及びvi)i)〜v)の混合物からなる群より選択される、請求項1に記載の膜。
- 使用される芳香族及び複素環式芳香族ジアミノカルボン酸は、ジアミノ安息香酸ならびにこれの一塩酸塩及び二塩酸塩誘導体である、請求項1に記載の膜。
- P2O5(酸定量)で算出されたアッセイが少なくとも83%であるポリリン酸が段階A)で使用される、請求項1に記載の膜。
- 一般式(I)および/または(II)および/または(III)および/または(IV)および/または(V)および/または(VI)および/または(VII)および/または(VIII)および/または(IX)および/または(X)および/または(XI)および/または(XII)および/または(XIII)および/または(XIV)および/または(XV)および/または(XVI)および/または(XVI)および/または(XVII)および/または(XVIII)および/または(XIX)および/または(XX)および/または(XXI)および/または(XXII):
基Ar1は、同一または異なるものであり、それぞれ、単環若しくは多環であってもよい2価の芳香族または複素環式芳香族基であり、
基Ar2は、同一または異なるものであり、それぞれ、単環若しくは多環であってもよい2価若しくは3価の芳香族または複素環式芳香族基であり、
基Ar3は、同一または異なるものであり、それぞれ、単環若しくは多環であってもよい3価の芳香族または複素環式芳香族基であり、
基Ar4は、同一または異なるものであり、それぞれ、単環若しくは多環であってもよい3価の芳香族または複素環式芳香族基であり、
基Ar5は、同一または異なるものであり、それぞれ、単環若しくは多環であってもよい4価の芳香族または複素環式芳香族基であり、
基Ar6は、同一または異なるものであり、それぞれ、単環若しくは多環であってもよい2価の芳香族または複素環式芳香族基であり、
基Ar7は、同一または異なるものであり、それぞれ、単環若しくは多環であってもよい2価の芳香族または複素環式芳香族基であり、
基Ar8は、同一または異なるものであり、それぞれ、単環若しくは多環であってもよい3価の芳香族または複素環式芳香族基であり、
基Ar9は、同一または異なるものであり、それぞれ、単環若しくは多環であってもよい2価若しくは3価若しくは4価の芳香族または複素環式芳香族基であり、
基Ar10は、同一または異なるものであり、それぞれ、単環若しくは多環であってもよい2価若しくは3価の芳香族または複素環式芳香族基であり、
基Ar11は、同一または異なるものであり、それぞれ、単環若しくは多環であってもよい2価の芳香族または複素環式芳香族基であり、
基Xは、同一または異なるものであり、それぞれ、水素原子、1〜20炭素原子を有する基、好ましくは分岐鎖または枝なし鎖のアルキル若しくはアルコキシ基、またはアリール基を追加の基として有する酸素、硫黄またはアミノ基であり、
基Rは、同一または異なるものであり、それぞれ、水素、アルキル基または芳香族基であり、ならびに
n、mは、それぞれ、10以上、好ましくは100以上の整数である、
の繰り返しアゾール単位を有し、硫黄含量(元素分析によって測定)が2〜20重量%であるポリマーが、段階C)で形成される、請求項1に記載の膜。 - 粘度が段階A)の後であってかつ段階B)の前にリン酸の添加によって調節される、請求項1に記載の膜。
- 段階C)に従って製造される膜が、該膜が自立して(self-support)おり、損傷を受けることなく支持体から脱離できるまでの温度及び時間、湿分の存在下で処理される、請求項1に記載の膜。
- 段階D)における膜の処理が、湿分または水および/または水蒸気の存在下で、0℃を超えて150℃以下の温度で、好ましくは10℃〜120℃の温度で、特に室温(20℃)〜90℃で、行なわれる、請求項1に記載の膜。
- 電極が段階B)での支持体として選択され、段階D)による処理が形成される膜がもはや自立できないような処理である、請求項1に記載の膜。
- スルホン化ポリアゾールを用いたものであり、かつ
A)ポリリン酸において、一以上の芳香族テトラアミノ化合物を、1つのカルボン酸モノマー当たり少なくとも2個のカルボン酸基及び1個スルホン酸基を有する一以上の芳香族スルホカルボン酸またはそのエステルと混合して、または一以上の芳香族および/または複素環式芳香族スルホン化ジアミノカルボン酸を混合して、溶液および/または分散液を形成し、
B)段階A)の混合物を用いた層を電極に塗布し、
C)350℃以下、好ましくは280℃以下の温度で不活性ガス下で段階B)に従って得られるシート状構造物/層を加熱して、ポリアゾールポリマーを形成し、
D)段階C)で形成した膜を処理する段階
を有する方法によって得られるプロトン伝導性ポリマー被膜を用いて提供される電極。 - 少なくとも1つの電極及び請求項1〜15のいずれかに記載の少なくとも1つの膜を有する膜−電極ユニット。
- 請求項17に記載の少なくとも1つの電極及び請求項1〜15のいずれかに記載の少なくとも1つの膜を有する膜−電極ユニット。
- 請求項17または18に記載の1以上の膜−電極ユニットを有する燃料電池。
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE10228657A DE10228657A1 (de) | 2002-06-27 | 2002-06-27 | Protonenleitende Membran und deren Verwendung |
PCT/EP2003/006308 WO2004003061A1 (de) | 2002-06-27 | 2003-06-14 | Protonenleitende membran und deren verwendung |
Publications (2)
Publication Number | Publication Date |
---|---|
JP2006507372A true JP2006507372A (ja) | 2006-03-02 |
JP4537199B2 JP4537199B2 (ja) | 2010-09-01 |
Family
ID=29723483
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2004516602A Expired - Fee Related JP4537199B2 (ja) | 2002-06-27 | 2003-06-14 | プロトン伝導性膜およびその使用 |
Country Status (9)
Country | Link |
---|---|
US (1) | US8076379B2 (ja) |
EP (1) | EP1519981B1 (ja) |
JP (1) | JP4537199B2 (ja) |
KR (1) | KR20050043802A (ja) |
CN (1) | CN1326917C (ja) |
AT (1) | ATE331753T1 (ja) |
CA (1) | CA2491239A1 (ja) |
DE (2) | DE10228657A1 (ja) |
WO (1) | WO2004003061A1 (ja) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPWO2015156228A1 (ja) * | 2014-04-07 | 2017-04-13 | 東レ株式会社 | 高分子電解質組成物ならびにそれを用いた高分子電解質膜、膜電極複合体および固体高分子形燃料電池 |
Families Citing this family (26)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE10117686A1 (de) * | 2001-04-09 | 2002-10-24 | Celanese Ventures Gmbh | Protonenleitende Membran und deren Verwendung |
DE10209419A1 (de) | 2002-03-05 | 2003-09-25 | Celanese Ventures Gmbh | Verfahren zur Herstellung einer Polymerelektrolytmembran und deren Anwendung in Brennstoffzellen |
EP1483316B1 (de) | 2002-03-06 | 2007-09-19 | Pemeas GmbH | PROTONENLEITENDE ELEKTROLYTMEMBRAN MIT GERINGER METHANOLDURCHLÄSSIGKEIT UND DEREN ANWENDUNG IN BRENNSTOFFZELLEN |
DE10235358A1 (de) * | 2002-08-02 | 2004-02-12 | Celanese Ventures Gmbh | Protonenleitende Polymermembran umfassend Phosphonsäuregruppen enthaltende Polymere und deren Anwendung in Brennstoffzellen |
DE10242708A1 (de) | 2002-09-13 | 2004-05-19 | Celanese Ventures Gmbh | Protonenleitende Membranen und deren Verwendung |
DE10246461A1 (de) * | 2002-10-04 | 2004-04-15 | Celanese Ventures Gmbh | Protonenleitende Polymermembran enthaltend Polyazolblends und deren Anwendung in Brennstoffzellen |
DE10246372A1 (de) * | 2002-10-04 | 2004-04-15 | Celanese Ventures Gmbh | Mit einer Katalysatorschicht beschichtete protonenleitende Polymermembran enthaltend Polyazole und deren Anwendung in Brennstoffzellen |
WO2005011039A2 (de) * | 2003-07-27 | 2005-02-03 | Pemeas Gmbh | Protonenleitende membran und deren verwendung |
DE102004044760A1 (de) * | 2004-09-16 | 2006-05-24 | Volkswagen Ag | Polymer-Membran, Membran-Elektroden-Einheit mit einer Polymer-Membran, Brennstoffzellenelektrode und Verfahren zur Herstellung |
JP4664641B2 (ja) * | 2004-09-29 | 2011-04-06 | 株式会社東芝 | プロトン伝導膜及び燃料電池 |
DE102005020604A1 (de) * | 2005-05-03 | 2006-11-16 | Pemeas Gmbh | Brennstoffzellen mit geringerem Gewicht und Volumen |
KR101129162B1 (ko) * | 2005-06-03 | 2012-03-28 | 토요 보세키 가부시기가이샤 | 양성자 전도성 고분자막 및 그의 제조 방법, 및 이를이용한 연료 전지 |
DE102005058578A1 (de) * | 2005-12-08 | 2007-06-28 | Sartorius Ag | Membranen aus Polyazolen, Verfahren zu ihrer Herstellung und Brennstoffzellen unter Verwendung derartiger Membranen |
CN100390222C (zh) * | 2006-03-13 | 2008-05-28 | 吉林大学 | 磺化聚合物/聚吡咯复合质子交换膜的制备方法 |
US7989116B2 (en) * | 2007-05-08 | 2011-08-02 | Toyota Motor Engineering & Manufacturing North America, Inc. | Electrolyte utilizing a lewis acid/bronstead acid complex |
CN101302339B (zh) * | 2007-05-09 | 2010-10-27 | 郑州泰达电子材料科技有限公司 | 导电性聚合物组合物和使用该组合物的固体电解电容器 |
US8299202B2 (en) * | 2008-01-30 | 2012-10-30 | Doetze Jakob Sikkema | Phenol compounds and (co)polymers thereof |
JP4444355B2 (ja) * | 2008-09-03 | 2010-03-31 | 株式会社東芝 | 燃料電池 |
DE102009001141A1 (de) * | 2008-10-29 | 2010-05-06 | Volkswagen Ag | Verfahren zur Herstellung einer Polymerelektrolytmembran |
JP5396902B2 (ja) * | 2009-02-20 | 2014-01-22 | Tdk株式会社 | リチウムイオン二次電池 |
RU2744370C2 (ru) | 2009-07-27 | 2021-03-05 | Баксалта Инкорпорейтед | Конъюгаты белков свертывания крови |
US9543607B2 (en) | 2013-02-22 | 2017-01-10 | National Research Council Of Canada | Process for producing ion exchange membranes by melt-processing of acidic PFSA ionomers |
RU2563255C1 (ru) * | 2014-09-22 | 2015-09-20 | Федеральное государственное бюджетное учреждение науки Институт неорганической химии им. А.В. Николаева Сибирского отделения Российской академии наук | Композиционный протонпроводящий материал |
CN108841020B (zh) * | 2018-05-16 | 2020-05-19 | 天津理工大学 | 一种具有离子导通性能的微孔聚合物膜及其制备方法及应用 |
CN112838252A (zh) * | 2019-11-25 | 2021-05-25 | 嘉应学院 | 一种燃料电池用高质子电导率的质子交换膜及其制备方法与应用 |
CN114288855B (zh) * | 2021-11-25 | 2023-03-10 | 国家电投集团氢能科技发展有限公司 | 一种水电解膜及其制备方法 |
Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2000248087A (ja) * | 1999-03-03 | 2000-09-12 | Stanley Electric Co Ltd | 重合膜の製造方法 |
JP2002146186A (ja) * | 2000-11-16 | 2002-05-22 | Toyobo Co Ltd | ポリアゾールポリマー系組成物及びそれを主成分とする膜、並びにポリアゾール系ポリマー組成物の成形方法 |
JP2002146022A (ja) * | 2000-11-15 | 2002-05-22 | Toyobo Co Ltd | スルホン酸またはホスホン酸含有イオン伝導性ポリイミダゾール |
JP2005536570A (ja) * | 2001-04-09 | 2005-12-02 | セラニーズ ベンチャーズ ゲー・エム・ベー・ハー | プロトン伝導性ポリマー膜 |
JP2005536571A (ja) * | 2001-09-12 | 2005-12-02 | セラニーズ ベンチャーズ ゲー・エム・ベー・ハー | プロトン伝導性膜およびその使用 |
Family Cites Families (21)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB1000525A (en) * | 1962-07-20 | 1965-08-04 | Teijin Ltd | Process for preparation of polybenzimidazoles |
US4191618A (en) * | 1977-12-23 | 1980-03-04 | General Electric Company | Production of halogens in an electrolysis cell with catalytic electrodes bonded to an ion transporting membrane and an oxygen depolarized cathode |
US4212714A (en) * | 1979-05-14 | 1980-07-15 | General Electric Company | Electrolysis of alkali metal halides in a three compartment cell with self-pressurized buffer compartment |
US4333805A (en) * | 1980-05-02 | 1982-06-08 | General Electric Company | Halogen evolution with improved anode catalyst |
US4634530A (en) * | 1980-09-29 | 1987-01-06 | Celanese Corporation | Chemical modification of preformed polybenzimidazole semipermeable membrane |
US5218076A (en) * | 1989-08-31 | 1993-06-08 | The Dow Chemical Company | Branch polybenzazole polymer and method of preparation |
US4997892A (en) * | 1989-11-13 | 1991-03-05 | Hoechst Celanese Corp. | Sulfalkylation of hydroxyethylated polybenzimidazole polymers |
US5525436A (en) | 1994-11-01 | 1996-06-11 | Case Western Reserve University | Proton conducting polymers used as membranes |
JPH11111310A (ja) | 1997-09-30 | 1999-04-23 | Aisin Seiki Co Ltd | 燃料電池用の固体高分子電解質膜およびその製造方法 |
JP3925764B2 (ja) | 1999-10-19 | 2007-06-06 | 株式会社豊田中央研究所 | 高耐久性固体高分子電解質 |
DE10109829A1 (de) | 2001-03-01 | 2002-09-05 | Celanese Ventures Gmbh | Polymermembran, Verfahren zu deren Herstellung sowie deren Verwendung |
DE10117687A1 (de) | 2001-04-09 | 2002-10-17 | Celanese Ventures Gmbh | Protonenleitende Membran und deren Verwendung |
US7647223B2 (en) * | 2001-08-16 | 2010-01-12 | Broadcom Corporation | Robust composite quantization with sub-quantizers and inverse sub-quantizers using illegal space |
DE10235358A1 (de) * | 2002-08-02 | 2004-02-12 | Celanese Ventures Gmbh | Protonenleitende Polymermembran umfassend Phosphonsäuregruppen enthaltende Polymere und deren Anwendung in Brennstoffzellen |
CN100544104C (zh) * | 2002-08-02 | 2009-09-23 | 巴斯夫燃料电池有限责任公司 | 包括含有磺酸基团的聚合物的质子导电聚合物膜及其在燃料电池中的应用 |
DE10242708A1 (de) * | 2002-09-13 | 2004-05-19 | Celanese Ventures Gmbh | Protonenleitende Membranen und deren Verwendung |
DE10246461A1 (de) * | 2002-10-04 | 2004-04-15 | Celanese Ventures Gmbh | Protonenleitende Polymermembran enthaltend Polyazolblends und deren Anwendung in Brennstoffzellen |
DE10246372A1 (de) * | 2002-10-04 | 2004-04-15 | Celanese Ventures Gmbh | Mit einer Katalysatorschicht beschichtete protonenleitende Polymermembran enthaltend Polyazole und deren Anwendung in Brennstoffzellen |
DE10246459A1 (de) * | 2002-10-04 | 2004-04-15 | Celanese Ventures Gmbh | Protonenleitende Polymermembran umfassend Phosphonsäuregruppen enthaltende Polyazole und deren Anwendung in Brennstoffzellen |
WO2005011039A2 (de) * | 2003-07-27 | 2005-02-03 | Pemeas Gmbh | Protonenleitende membran und deren verwendung |
DE102005020604A1 (de) | 2005-05-03 | 2006-11-16 | Pemeas Gmbh | Brennstoffzellen mit geringerem Gewicht und Volumen |
-
2002
- 2002-06-27 DE DE10228657A patent/DE10228657A1/de not_active Withdrawn
-
2003
- 2003-06-14 CN CNB038202387A patent/CN1326917C/zh not_active Expired - Fee Related
- 2003-06-14 WO PCT/EP2003/006308 patent/WO2004003061A1/de active IP Right Grant
- 2003-06-14 JP JP2004516602A patent/JP4537199B2/ja not_active Expired - Fee Related
- 2003-06-14 DE DE50304073T patent/DE50304073D1/de not_active Expired - Lifetime
- 2003-06-14 AT AT03740253T patent/ATE331753T1/de not_active IP Right Cessation
- 2003-06-14 CA CA002491239A patent/CA2491239A1/en not_active Abandoned
- 2003-06-14 US US10/519,281 patent/US8076379B2/en not_active Expired - Fee Related
- 2003-06-14 EP EP03740253A patent/EP1519981B1/de not_active Expired - Lifetime
- 2003-06-14 KR KR1020047021336A patent/KR20050043802A/ko not_active Application Discontinuation
Patent Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2000248087A (ja) * | 1999-03-03 | 2000-09-12 | Stanley Electric Co Ltd | 重合膜の製造方法 |
JP2002146022A (ja) * | 2000-11-15 | 2002-05-22 | Toyobo Co Ltd | スルホン酸またはホスホン酸含有イオン伝導性ポリイミダゾール |
JP2002146186A (ja) * | 2000-11-16 | 2002-05-22 | Toyobo Co Ltd | ポリアゾールポリマー系組成物及びそれを主成分とする膜、並びにポリアゾール系ポリマー組成物の成形方法 |
JP2005536570A (ja) * | 2001-04-09 | 2005-12-02 | セラニーズ ベンチャーズ ゲー・エム・ベー・ハー | プロトン伝導性ポリマー膜 |
JP2005536571A (ja) * | 2001-09-12 | 2005-12-02 | セラニーズ ベンチャーズ ゲー・エム・ベー・ハー | プロトン伝導性膜およびその使用 |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPWO2015156228A1 (ja) * | 2014-04-07 | 2017-04-13 | 東レ株式会社 | 高分子電解質組成物ならびにそれを用いた高分子電解質膜、膜電極複合体および固体高分子形燃料電池 |
Also Published As
Publication number | Publication date |
---|---|
DE10228657A1 (de) | 2004-01-15 |
KR20050043802A (ko) | 2005-05-11 |
CN1326917C (zh) | 2007-07-18 |
WO2004003061A1 (de) | 2004-01-08 |
EP1519981A1 (de) | 2005-04-06 |
CN1697852A (zh) | 2005-11-16 |
US8076379B2 (en) | 2011-12-13 |
EP1519981B1 (de) | 2006-06-28 |
ATE331753T1 (de) | 2006-07-15 |
JP4537199B2 (ja) | 2010-09-01 |
CA2491239A1 (en) | 2004-01-08 |
US20060057449A1 (en) | 2006-03-16 |
DE50304073D1 (de) | 2006-08-10 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
JP4537199B2 (ja) | プロトン伝導性膜およびその使用 | |
JP5468051B2 (ja) | プロトン伝導性膜およびその使用 | |
US7235320B2 (en) | Proton-conducting membrane and use thereof | |
US7384552B2 (en) | Proton-conducting membrane and the use thereof | |
JP4450734B2 (ja) | ホスホン酸基含有ポリアゾールを含むプロトン伝導性高分子膜及び燃料電池におけるその使用。 | |
US8142917B2 (en) | Proton-conducting polymer membrane comprising polyazole blends and its use in fuel cells | |
US7745030B2 (en) | Proton-conducting polymer membrane comprising sulfonic acid-containing polyazoles, and use thereof in fuel cells | |
EP2804889B1 (en) | Proton-conducting membrane, method for their production and their use in electrochemical cells | |
JP5279771B2 (ja) | プロトン伝導性ポリマー膜 |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
A621 | Written request for application examination |
Free format text: JAPANESE INTERMEDIATE CODE: A621 Effective date: 20060602 |
|
A977 | Report on retrieval |
Free format text: JAPANESE INTERMEDIATE CODE: A971007 Effective date: 20081016 |
|
A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20081028 |
|
A601 | Written request for extension of time |
Free format text: JAPANESE INTERMEDIATE CODE: A601 Effective date: 20090128 |
|
A602 | Written permission of extension of time |
Free format text: JAPANESE INTERMEDIATE CODE: A602 Effective date: 20090204 |
|
A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20090302 |
|
A02 | Decision of refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A02 Effective date: 20091215 |
|
A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20100414 |
|
A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A821 Effective date: 20100415 |
|
A911 | Transfer to examiner for re-examination before appeal (zenchi) |
Free format text: JAPANESE INTERMEDIATE CODE: A911 Effective date: 20100519 |
|
TRDD | Decision of grant or rejection written | ||
A01 | Written decision to grant a patent or to grant a registration (utility model) |
Free format text: JAPANESE INTERMEDIATE CODE: A01 Effective date: 20100608 |
|
A01 | Written decision to grant a patent or to grant a registration (utility model) |
Free format text: JAPANESE INTERMEDIATE CODE: A01 |
|
A61 | First payment of annual fees (during grant procedure) |
Free format text: JAPANESE INTERMEDIATE CODE: A61 Effective date: 20100617 |
|
FPAY | Renewal fee payment (event date is renewal date of database) |
Free format text: PAYMENT UNTIL: 20130625 Year of fee payment: 3 |
|
R150 | Certificate of patent or registration of utility model |
Free format text: JAPANESE INTERMEDIATE CODE: R150 |
|
LAPS | Cancellation because of no payment of annual fees |