CN100503689C - 质子导电膜及其应用 - Google Patents
质子导电膜及其应用 Download PDFInfo
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- CN100503689C CN100503689C CNB028079558A CN02807955A CN100503689C CN 100503689 C CN100503689 C CN 100503689C CN B028079558 A CNB028079558 A CN B028079558A CN 02807955 A CN02807955 A CN 02807955A CN 100503689 C CN100503689 C CN 100503689C
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- CN
- China
- Prior art keywords
- film
- acid
- diacid
- oneself
- fragrance
- 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.)
- Expired - Fee Related
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- 239000012528 membrane Substances 0.000 title abstract description 8
- 239000000446 fuel Substances 0.000 claims abstract description 14
- 239000000126 substance Substances 0.000 claims abstract description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 44
- 239000000203 mixture Substances 0.000 claims description 43
- 125000003118 aryl group Chemical group 0.000 claims description 40
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 37
- 239000002253 acid Substances 0.000 claims description 34
- 239000003205 fragrance Substances 0.000 claims description 32
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 claims description 27
- 229920000128 polypyrrole Polymers 0.000 claims description 26
- 229920000642 polymer Polymers 0.000 claims description 24
- -1 amino m-phthalic acid Chemical compound 0.000 claims description 21
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 claims description 20
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims description 17
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 17
- 238000000034 method Methods 0.000 claims description 15
- 239000004693 Polybenzimidazole Substances 0.000 claims description 13
- 229920002480 polybenzimidazole Polymers 0.000 claims description 13
- 239000007789 gas Substances 0.000 claims description 12
- 150000008065 acid anhydrides Chemical class 0.000 claims description 10
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 10
- 150000001263 acyl chlorides Chemical class 0.000 claims description 9
- 125000000217 alkyl group Chemical group 0.000 claims description 9
- 229910052799 carbon Inorganic materials 0.000 claims description 9
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 9
- 238000010438 heat treatment Methods 0.000 claims description 9
- 229910052760 oxygen Inorganic materials 0.000 claims description 9
- 238000002360 preparation method Methods 0.000 claims description 9
- VACCAVUAMIDAGB-UHFFFAOYSA-N sulfamethizole Chemical compound S1C(C)=NN=C1NS(=O)(=O)C1=CC=C(N)C=C1 VACCAVUAMIDAGB-UHFFFAOYSA-N 0.000 claims description 9
- 125000003837 (C1-C20) alkyl group Chemical group 0.000 claims description 8
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 8
- 239000001301 oxygen Substances 0.000 claims description 8
- 150000002148 esters Chemical class 0.000 claims description 7
- 229910052757 nitrogen Inorganic materials 0.000 claims description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 6
- YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 claims description 6
- 239000006185 dispersion Substances 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- 239000000178 monomer 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
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical group C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 claims description 5
- 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 5
- 229910052731 fluorine Inorganic materials 0.000 claims description 5
- 239000011737 fluorine Substances 0.000 claims description 5
- 125000001072 heteroaryl group Chemical group 0.000 claims description 5
- 239000007788 liquid Substances 0.000 claims description 5
- 239000011159 matrix material Substances 0.000 claims description 5
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 5
- 239000000725 suspension Substances 0.000 claims description 5
- 150000000000 tetracarboxylic acids Chemical class 0.000 claims description 5
- 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
- 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 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
- 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
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 4
- 239000005864 Sulphur Substances 0.000 claims description 4
- 230000002378 acidificating effect Effects 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
- 229910052698 phosphorus Inorganic materials 0.000 claims description 4
- 150000005846 sugar alcohols Polymers 0.000 claims description 4
- 238000004448 titration Methods 0.000 claims description 4
- AYNPIRVEWMUJDE-UHFFFAOYSA-N 2,5-dichlorohydroquinone Chemical compound OC1=CC(Cl)=C(O)C=C1Cl AYNPIRVEWMUJDE-UHFFFAOYSA-N 0.000 claims description 3
- 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 3
- 239000001257 hydrogen Substances 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- 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 3
- 238000007669 thermal treatment Methods 0.000 claims description 3
- 150000003628 tricarboxylic acids Chemical class 0.000 claims description 3
- WBYWAXJHAXSJNI-VOTSOKGWSA-M .beta-Phenylacrylic acid Natural products [O-]C(=O)\C=C\C1=CC=CC=C1 WBYWAXJHAXSJNI-VOTSOKGWSA-M 0.000 claims description 2
- NSGXIBWMJZWTPY-UHFFFAOYSA-N 1,1,1,3,3,3-hexafluoropropane Chemical compound FC(F)(F)CC(F)(F)F NSGXIBWMJZWTPY-UHFFFAOYSA-N 0.000 claims description 2
- SOZFIIXUNAKEJP-UHFFFAOYSA-N 1,2,3,4-tetrafluorobenzene Chemical compound FC1=CC=C(F)C(F)=C1F SOZFIIXUNAKEJP-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
- 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 2
- AQBVAFIJSHZDBS-UHFFFAOYSA-N 4-(3,4-diaminophenyl)benzene-1,2-diamine propane Chemical compound CCC.NC=1C=C(C=CC1N)C1=CC(=C(C=C1)N)N AQBVAFIJSHZDBS-UHFFFAOYSA-N 0.000 claims description 2
- ULRYKCILDSQBMT-UHFFFAOYSA-N 4-(3,4-diaminophenyl)benzene-1,2-diamine;methane Chemical compound C.C1=C(N)C(N)=CC=C1C1=CC=C(N)C(N)=C1 ULRYKCILDSQBMT-UHFFFAOYSA-N 0.000 claims description 2
- PIKFVGUMJSTJQO-UHFFFAOYSA-N C1=CC=C2C=CC3=CC=CC4=CC=C1C2=C34.[N] Chemical class C1=CC=C2C=CC3=CC=CC4=CC=C1C2=C34.[N] PIKFVGUMJSTJQO-UHFFFAOYSA-N 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 229920000292 Polyquinoline Polymers 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
- 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
- 229930016911 cinnamic acid Natural products 0.000 claims description 2
- 235000013985 cinnamic acid Nutrition 0.000 claims description 2
- 239000011248 coating agent Substances 0.000 claims description 2
- 238000000576 coating method Methods 0.000 claims description 2
- 229960004979 fampridine Drugs 0.000 claims description 2
- 150000001261 hydroxy acids Chemical class 0.000 claims description 2
- WBYWAXJHAXSJNI-UHFFFAOYSA-N methyl p-hydroxycinnamate Natural products OC(=O)C=CC1=CC=CC=C1 WBYWAXJHAXSJNI-UHFFFAOYSA-N 0.000 claims description 2
- PYLWMHQQBFSUBP-UHFFFAOYSA-N monofluorobenzene Chemical compound FC1=CC=CC=C1 PYLWMHQQBFSUBP-UHFFFAOYSA-N 0.000 claims description 2
- 125000004437 phosphorous atom Chemical group 0.000 claims description 2
- 229920002577 polybenzoxazole Polymers 0.000 claims description 2
- 150000003457 sulfones Chemical class 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims 2
- 239000002322 conducting polymer Substances 0.000 abstract 1
- 229920001940 conductive polymer Polymers 0.000 abstract 1
- 239000005518 polymer electrolyte Substances 0.000 abstract 1
- 239000000243 solution Substances 0.000 description 51
- 239000004305 biphenyl Substances 0.000 description 28
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 25
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 18
- 235000011007 phosphoric acid Nutrition 0.000 description 17
- 235000010290 biphenyl Nutrition 0.000 description 13
- 239000005357 flat glass Substances 0.000 description 13
- 238000006243 chemical reaction Methods 0.000 description 12
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 10
- 239000000908 ammonium hydroxide Substances 0.000 description 10
- 150000002460 imidazoles Chemical class 0.000 description 10
- 238000006386 neutralization reaction Methods 0.000 description 10
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- 239000000654 additive Substances 0.000 description 9
- 238000006116 polymerization reaction Methods 0.000 description 8
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 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
- 230000000996 additive effect Effects 0.000 description 6
- 230000007062 hydrolysis Effects 0.000 description 6
- 238000006460 hydrolysis reaction Methods 0.000 description 6
- 150000003254 radicals Chemical class 0.000 description 6
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 5
- 240000000233 Melia azedarach Species 0.000 description 4
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 4
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- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 4
- UJMDYLWCYJJYMO-UHFFFAOYSA-N benzene-1,2,3-tricarboxylic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1C(O)=O UJMDYLWCYJJYMO-UHFFFAOYSA-N 0.000 description 4
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- DBFNNZPHSUROFB-UHFFFAOYSA-N 4-amino-N-fluorobenzenesulfonamide Chemical compound S(=O)(C1=CC=C(C=C1)N)(=O)NF DBFNNZPHSUROFB-UHFFFAOYSA-N 0.000 description 2
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- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
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- GDRVFDDBLLKWRI-UHFFFAOYSA-N 4H-quinolizine Chemical compound C1=CC=CN2CC=CC=C21 GDRVFDDBLLKWRI-UHFFFAOYSA-N 0.000 description 1
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Classifications
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- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
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- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D179/00—Coating compositions based on 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 C09D161/00 - C09D177/00
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- Manufacture Of Macromolecular Shaped Articles (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Fuel Cell (AREA)
- Conductive Materials (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Silicon Polymers (AREA)
Abstract
Description
膜厚 | IEC | 导电率@120℃ | |
实施例 | [μm] | [meq/g] | [mS/cm] |
1 | 280 | 139 | 120 |
2 | 340 | 166 | 130 |
3 | 156 | 190 | 122 |
4 | 220 | 126 | 117 |
5 | 300 | 340 | 180 |
6 | 250 | 130 | 120 |
7 | 281 | 121 | 116 |
8 | 300 | 178 | 160 |
9 | 247 | 124 | 130 |
10 | 322 | 151 | 121 |
11 | 330 | 79 | 112 |
12 | 314 | 168 | 150 |
13 | 140 | 118 | 110 |
14 | 200 | 131 | 114 |
15 | 500 | 230 | 165 |
16 | 440 | 290 | 160 |
Claims (37)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
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DE10117686A DE10117686A1 (de) | 2001-04-09 | 2001-04-09 | Protonenleitende Membran und deren Verwendung |
DE10117686.4 | 2001-04-09 |
Publications (2)
Publication Number | Publication Date |
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CN1606585A CN1606585A (zh) | 2005-04-13 |
CN100503689C true CN100503689C (zh) | 2009-06-24 |
Family
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CNB028079558A Expired - Fee Related CN100503689C (zh) | 2001-04-09 | 2002-04-09 | 质子导电膜及其应用 |
Country Status (12)
Country | Link |
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US (3) | US7384552B2 (zh) |
EP (2) | EP1379573B1 (zh) |
JP (1) | JP4663215B2 (zh) |
KR (1) | KR100910117B1 (zh) |
CN (1) | CN100503689C (zh) |
AT (1) | ATE491739T1 (zh) |
BR (1) | BR0208795A (zh) |
CA (1) | CA2443541C (zh) |
DE (2) | DE10117686A1 (zh) |
DK (1) | DK1379573T3 (zh) |
MX (1) | MXPA03009184A (zh) |
WO (1) | WO2002088219A1 (zh) |
Families Citing this family (91)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE10117687A1 (de) | 2001-04-09 | 2002-10-17 | Celanese Ventures Gmbh | Protonenleitende Membran und deren Verwendung |
DE10117686A1 (de) | 2001-04-09 | 2002-10-24 | Celanese Ventures Gmbh | Protonenleitende Membran und deren Verwendung |
DE10129458A1 (de) * | 2001-06-19 | 2003-01-02 | Celanese Ventures Gmbh | Verbesserte Polymerfolien auf Basis von Polyazolen |
DE10209419A1 (de) | 2002-03-05 | 2003-09-25 | Celanese Ventures Gmbh | Verfahren zur Herstellung einer Polymerelektrolytmembran und deren Anwendung in Brennstoffzellen |
US7846982B2 (en) * | 2002-03-06 | 2010-12-07 | Pemeas Gmbh | Proton conducting electrolyte membrane having reduced methanol permeability and the use thereof in fuel cells |
US20050118478A1 (en) * | 2002-03-06 | 2005-06-02 | Joachim Kiefer | Mixture comprising sulphonic acid containing vinyl, polymer electrolyte membrane comprising polyvinylsulphonic acid and the use thereof in fuel cells |
DE10213540A1 (de) * | 2002-03-06 | 2004-02-19 | Celanese Ventures Gmbh | Lösung aus Vinylphosphonsäure, Verfahren zur Herstellung einer Polymerelektrolytmembran aus Polyvinylphosphaonsäure und deren Anwendung in Brennstoffzellen |
JP4638220B2 (ja) | 2002-04-25 | 2011-02-23 | ビーエーエスエフ フューエル セル ゲゼルシャフト ミット ベシュレンクテル ハフツング | 多層電解質膜 |
DE10224452C1 (de) | 2002-05-29 | 2003-11-20 | Fraunhofer Ges Forschung | Protonenleitende Polymermembran sowie Verfahren zu deren Herstellung |
DE10228657A1 (de) * | 2002-06-27 | 2004-01-15 | Celanese Ventures Gmbh | Protonenleitende Membran und deren Verwendung |
DE10230477A1 (de) | 2002-07-06 | 2004-01-15 | Celanese Ventures Gmbh | Funktionalisierte Polyazole, Verfahren zu ihrer Herstellung sowie ihre Verwendung |
DE10235358A1 (de) * | 2002-08-02 | 2004-02-12 | Celanese Ventures Gmbh | Protonenleitende Polymermembran umfassend Phosphonsäuregruppen enthaltende Polymere und deren Anwendung in Brennstoffzellen |
US7332530B2 (en) | 2002-08-02 | 2008-02-19 | Celanese Ventures Gmbh | Proton-conducting polymer membrane comprising a polymer with sulphonic acid groups and use thereof in fuel cells |
DE10235360A1 (de) | 2002-08-02 | 2004-02-19 | Celanese Ventures Gmbh | Membran-Elektrodeneinheiten mit langer Lebensdauer |
JP2005537384A (ja) | 2002-08-29 | 2005-12-08 | ペメアス ゲーエムベーハー | プロトン伝導性ポリマー膜の製造方法、改良されたポリマー膜、および燃料電池におけるその使用 |
DE10239701A1 (de) * | 2002-08-29 | 2004-03-11 | Celanese Ventures Gmbh | Polymerfolie auf Basis von Polyazolen und deren Verwendung |
DE10242708A1 (de) | 2002-09-13 | 2004-05-19 | Celanese Ventures Gmbh | Protonenleitende Membranen und deren Verwendung |
DE10246459A1 (de) | 2002-10-04 | 2004-04-15 | Celanese Ventures Gmbh | Protonenleitende Polymermembran umfassend Phosphonsäuregruppen enthaltende Polyazole und deren Anwendung in Brennstoffzellen |
DE10246373A1 (de) | 2002-10-04 | 2004-04-15 | Celanese Ventures Gmbh | Protonenleitende Polymermembran umfassend Sulfonsäuregruppen enthaltende Polyazole 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 |
DE10246461A1 (de) * | 2002-10-04 | 2004-04-15 | Celanese Ventures Gmbh | Protonenleitende Polymermembran enthaltend Polyazolblends und deren Anwendung in Brennstoffzellen |
DE10301810A1 (de) | 2003-01-20 | 2004-07-29 | Sartorius Ag | Membran-Elektroden-Einheit, Polymermembranen für eine Membran-Elektroden-Einheit und Polymerelektrolyt-Brennstoffzellen sowie Verfahren zur Herstellung derselben |
WO2005011039A2 (de) * | 2003-07-27 | 2005-02-03 | Pemeas Gmbh | Protonenleitende membran und deren verwendung |
KR100570745B1 (ko) | 2003-10-30 | 2006-04-12 | 삼성에스디아이 주식회사 | 폴리(2,5-벤즈이미다졸)의 제조방법 |
DE10361832A1 (de) * | 2003-12-30 | 2005-07-28 | Celanese Ventures Gmbh | Protonenleitende Membran und deren Verwendung |
DE10361833A1 (de) * | 2003-12-30 | 2005-08-04 | Celanese Ventures Gmbh | Protonenleitende Membran und deren Verwendung |
DE10361932A1 (de) | 2003-12-30 | 2005-07-28 | Celanese Ventures Gmbh | Protonenleitende Membran und deren Verwendung |
DE102004008628A1 (de) * | 2004-02-21 | 2005-09-08 | Celanese Ventures Gmbh | Membran-Elektroden-Einheit mit hoher Leistung und deren Anwendung in Brennstoffzellen |
DE102004034139A1 (de) | 2004-07-15 | 2006-02-02 | Pemeas Gmbh | Verfahren zur Herstellung von Membran-Elektroden-Einheiten |
JP4290616B2 (ja) * | 2004-07-21 | 2009-07-08 | 三洋電機株式会社 | 燃料電池用電解質、膜電極接合体、燃料電池スタック、燃料電池システムおよび燃料電池用電解質の製造方法 |
EP1624512A2 (en) * | 2004-08-05 | 2006-02-08 | Pemeas GmbH | Long-life membrane electrode assemblies |
US7736782B2 (en) * | 2004-10-20 | 2010-06-15 | Samsung Sdi Co., Ltd. | Proton conductive solid polymer electrolyte and fuel cell |
KR100599719B1 (ko) | 2004-11-24 | 2006-07-12 | 삼성에스디아이 주식회사 | 연료 전지용 고분자 전해질 막 및 이를 포함하는 연료전지 시스템 |
JP4996823B2 (ja) * | 2004-11-26 | 2012-08-08 | 三洋電機株式会社 | 燃料電池用電極、及びそれを用いた燃料電池 |
KR100644856B1 (ko) * | 2005-03-17 | 2006-11-24 | 한국과학기술연구원 | 연료전지 멤브레인 및 그 제조 방법 |
JP4886675B2 (ja) * | 2005-03-17 | 2012-02-29 | 帝人株式会社 | 電解質膜 |
US7851584B2 (en) * | 2005-03-28 | 2010-12-14 | E. I. Du Pont De Nemours And Company | Process for preparing monomer complexes |
DE102005020604A1 (de) * | 2005-05-03 | 2006-11-16 | Pemeas Gmbh | Brennstoffzellen mit geringerem Gewicht und Volumen |
US7838138B2 (en) * | 2005-09-19 | 2010-11-23 | 3M Innovative Properties Company | Fuel cell electrolyte membrane with basic polymer |
US7517604B2 (en) * | 2005-09-19 | 2009-04-14 | 3M Innovative Properties Company | Fuel cell electrolyte membrane with acidic polymer |
CN101346839B (zh) * | 2005-10-27 | 2012-06-13 | Utc电力公司 | 用以延长燃料电池膜和离聚物寿命的合金催化剂 |
KR100819676B1 (ko) * | 2005-11-14 | 2008-04-03 | 주식회사 엘지화학 | 브랜치된 멀티블록 폴리벤즈이미다졸-벤즈아마이드공중합체 및 제조방법, 이를 이용한 전해질막 및 전해질페이스트/겔 |
US7806275B2 (en) * | 2007-05-09 | 2010-10-05 | The United States Of America As Represented By The Secretary Of The Interior, The Bureau Of Reclamation | Chlorine resistant polyamides and membranes made from the same |
CN102015836A (zh) * | 2008-02-27 | 2011-04-13 | 索维公司 | 聚合物组合物,包含该聚合物组合物的聚合物膜,用于制备它的方法以及包含该膜的燃料电池 |
WO2009109512A1 (de) * | 2008-02-29 | 2009-09-11 | Basf Se | Ionische flüssigkeit enthaltende katalysatortinte und deren verwendung in elektroden-, ccm-, gde- und mea-herstellung |
EP2289122A1 (de) * | 2008-05-15 | 2011-03-02 | Basf Se | Protonenleitende membran und deren verwendung |
US8707875B2 (en) * | 2009-05-18 | 2014-04-29 | Covanta Energy Corporation | Gasification combustion system |
EP2373406A1 (de) | 2008-12-06 | 2011-10-12 | Basf Se | Verfahren zur herstellung einer protonenleitenden membran |
KR20110106426A (ko) * | 2009-01-14 | 2011-09-28 | 바스프 에스이 | 양성자-전도성 막 제조용 단량체 비드 |
KR101124506B1 (ko) * | 2009-04-24 | 2012-03-16 | 서울대학교산학협력단 | 폴리아졸의 가교체, 그 제조방법, 이를 포함하는 연료전지용 전극, 연료전지용 전해질막, 그 제조방법 및 이를 포함하는 연료전지 |
US20120195929A1 (en) * | 2009-06-04 | 2012-08-02 | George Eisenbarth | Compounds that modulate autoimmunity and methods of using the same |
EP2264040A1 (en) | 2009-06-05 | 2010-12-22 | Max-Planck-Gesellschaft zur Förderung der Wissenschaften e.V. | Proton-conducting organic materials |
US8722279B2 (en) | 2009-06-20 | 2014-05-13 | Basf Se | Polyazole-containing composition |
WO2010145828A2 (de) | 2009-06-20 | 2010-12-23 | Basf Se | Verfahren zur herstellung eines hochmolekularen polyazols |
WO2011003538A1 (de) | 2009-07-09 | 2011-01-13 | Basf Se | Methode zur mechanischen stabilisierung von stickstoffhaltigen polymeren |
WO2011003539A1 (de) | 2009-07-09 | 2011-01-13 | Basf Se | Verfahren zur stabilisierung von stickstoffhaltigen polymeren |
US20130175168A1 (en) * | 2009-08-04 | 2013-07-11 | Gentex Corporation | Microelectrode Assemblies and Associated Electrochemical Sensors for Use in Gas and or Fire Detection Devices |
DE102009028758A1 (de) * | 2009-08-20 | 2011-02-24 | Volkswagen Ag | Langzeitstabile Polymerelektrolytmembran für HT-Brennstoffzellen und Verfahren zu ihrer Herstellung |
KR101317510B1 (ko) * | 2009-09-15 | 2013-10-15 | 서울대학교산학협력단 | 하이드라지늄 설페이트가 분산된 폴리벤즈이미다졸계 복합막 및 이를 사용하는 연료전지용 전해질막 |
US20110189581A1 (en) * | 2010-02-04 | 2011-08-04 | Samsung Electronics Co., Ltd. | Compound, cross-linked material thereof, double cross-linked polymer thereof, and electrolyte membrane, electrode for fuel cell and fuel cell including same |
US9112232B2 (en) | 2010-02-05 | 2015-08-18 | Samsung Electronics Co., Ltd. | Composition, polymer thereof, electrode and electrolyte membrane for fuel cell, and fuel cell including the same |
US9368803B2 (en) | 2010-03-03 | 2016-06-14 | Samsung Electronics Co., Ltd. | Composition, method of preparing the composition, electrode including the composition, and fuel cell including the electrode |
WO2011154811A1 (en) | 2010-06-08 | 2011-12-15 | Rensselaer Polytechnic Institute | Method for the production of an electrochemical cell |
US8673183B2 (en) | 2010-07-06 | 2014-03-18 | National Research Council Of Canada | Tetrazine monomers and copolymers for use in organic electronic devices |
JP5279771B2 (ja) * | 2010-08-06 | 2013-09-04 | ベーアーエスエフ フューエル セル ゲーエムベーハー | プロトン伝導性ポリマー膜 |
US8461296B2 (en) | 2011-03-24 | 2013-06-11 | Basf Se | Method for mechanical stabilization of nitrogen-containing polymers |
US9325025B2 (en) | 2011-04-14 | 2016-04-26 | Basf Se | Membrane electrode assemblies and fuel cells with long lifetime |
DE102012007178A1 (de) | 2011-04-14 | 2012-10-18 | Basf Se | Verbesserte Membran-Elektrodeneinheiten und Brennstoffzellen mit langer Lebensdauer |
US9006339B2 (en) | 2011-05-10 | 2015-04-14 | Basf Se | Mechanically stabilized polyazoles comprising at least one polyvinyl alcohol |
US9629848B2 (en) | 2011-05-26 | 2017-04-25 | The Regents Of The University Of Colorado, A Body Corporate | Compounds that modulate autoimmunity and methods of using the same |
US9812725B2 (en) | 2012-01-17 | 2017-11-07 | Basf Se | Proton-conducting membrane and use thereof |
WO2013108112A1 (en) * | 2012-01-17 | 2013-07-25 | Basf Se | Proton-conducting membrane, method for their production and their use in electrochemical cells |
US20130183603A1 (en) | 2012-01-17 | 2013-07-18 | Basf Se | Proton-conducting membrane, method for their production and their use in electrochemical cells |
KR101350858B1 (ko) | 2012-02-20 | 2014-01-16 | 한국과학기술연구원 | 폴리벤지이미다졸코벤족사졸 및 그 제조 방법 |
US9130208B2 (en) | 2012-05-08 | 2015-09-08 | Basf Se | Membrane electrode assemblies and fuel cells with long lifetime |
US9283523B2 (en) * | 2012-05-25 | 2016-03-15 | Pbi Performance Products, Inc. | Acid resistant PBI membrane for pervaporation dehydration of acidic solvents |
US9056284B2 (en) | 2012-08-10 | 2015-06-16 | The United States Of America, As Represented By The Secretary Of The Interior | Chlorine resistant amides, polyamides, and membranes made from the same |
WO2014111792A1 (en) * | 2013-01-16 | 2014-07-24 | Basf Se | Proton-conducting membrane, method for their production and their use in electrochemical cells |
WO2014111793A1 (en) * | 2013-01-16 | 2014-07-24 | Basf Se | Proton-conducting membrane, method for their production and their use in electrochemical cells |
DK2987194T3 (da) | 2013-04-16 | 2019-09-09 | Basf Se | Fremgangsmåde til fremstilling af membranelektrodeenheder |
CA2922667C (en) * | 2013-08-30 | 2021-11-09 | Council Of Scientific And Industrial Research | Co-abpbi membranes and process for the preparation thereof |
DK2843743T3 (en) | 2013-09-02 | 2018-07-16 | Basf Se | Membrane electrode units for high temperature fuel cells with improved stability |
EP2869382B1 (en) | 2013-10-30 | 2018-12-12 | Basf Se | Improved membrane electrode assemblies |
US10363288B2 (en) | 2015-01-14 | 2019-07-30 | National Jewish Health | Insulin mimotopes and methods of using the same |
US9820957B2 (en) | 2016-03-24 | 2017-11-21 | The Regents Of The University Of Colorado, A Body Corporate | Methods of treating autoimmunity |
CN110880614A (zh) * | 2017-11-19 | 2020-03-13 | 湖南辰砾新材料有限公司 | 一种高温无水质子交换膜的燃料电池 |
US11052060B2 (en) | 2018-02-12 | 2021-07-06 | The Regents Of The University Of Colorado, A Body Corporate | Compounds and methods for treating autoimmunity |
US11013707B2 (en) | 2018-03-23 | 2021-05-25 | The Regents Of The University Of Colorado, A Body Corporate | Administration of oral methyldopa |
CN112820892A (zh) * | 2019-11-18 | 2021-05-18 | 坤艾新材料科技(上海)有限公司 | 一种气体扩散电极和包括该气体扩散电极的电池 |
CN110983364A (zh) * | 2019-12-20 | 2020-04-10 | 湖南七纬科技有限公司 | 一种高亲水性电解水用隔膜及其制备方法 |
CN114892341A (zh) * | 2022-05-10 | 2022-08-12 | 陕西科技大学 | 一种基于酸裂解的芳香族杂环纳米纤维薄膜及其制备方法 |
Family Cites Families (42)
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 |
US5525436A (en) * | 1994-11-01 | 1996-06-11 | Case Western Reserve University | Proton conducting polymers used as membranes |
US5716727A (en) * | 1996-04-01 | 1998-02-10 | Case Western Reserve University | Proton conducting polymers prepared by direct acid casting |
EP1034174B1 (en) * | 1997-11-05 | 2003-08-13 | Neurosearch A/S | Azaring-ether derivatives and their use as nicotinic ach receptor modulators |
JP2000273214A (ja) * | 1999-03-29 | 2000-10-03 | Toray Ind Inc | ポリベンザゾールフィルム及びそれを用いた磁気記録媒体 |
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 |
DE10052237A1 (de) * | 2000-10-21 | 2002-08-01 | Celanese Ventures Gmbh | Verfahren zur Herstellung einer Lösung von einem Polymer enthaltend wiederkehrende Azoleinheiten, nach dem Verfahren hergestellte Lösungen und deren Verwendung |
CN100358938C (zh) * | 2000-11-13 | 2008-01-02 | 东洋纺织株式会社 | 具有磺酸基和/或膦酸基的聚吲哚类化合物、固体电解质膜/电极催化剂层复合体及其制造方法 |
JP2002146013A (ja) * | 2000-11-15 | 2002-05-22 | Toyobo Co Ltd | イオン伝導性ホスホン酸含有ポリアゾール |
DE10109829A1 (de) | 2001-03-01 | 2002-09-05 | Celanese Ventures Gmbh | Polymermembran, Verfahren zu deren Herstellung sowie deren Verwendung |
DE10117686A1 (de) | 2001-04-09 | 2002-10-24 | Celanese Ventures Gmbh | Protonenleitende Membran und deren Verwendung |
DE10117687A1 (de) | 2001-04-09 | 2002-10-17 | Celanese Ventures Gmbh | Protonenleitende Membran und deren Verwendung |
DE10129458A1 (de) | 2001-06-19 | 2003-01-02 | Celanese Ventures Gmbh | Verbesserte Polymerfolien auf Basis von Polyazolen |
DE10133739A1 (de) * | 2001-07-11 | 2003-01-30 | Mewa Textil Service Ag & Co Man Ohg | Transportbehälter |
DE10140147A1 (de) * | 2001-08-16 | 2003-03-06 | Celanese Ventures Gmbh | Verfahren zur Herstellung einer Blend-Membran aus verbrücktem Polymer und Brennstoffzelle |
DE10209784A1 (de) * | 2001-09-01 | 2003-12-04 | Univ Stuttgart Inst Fuer Chemi | Sulfinatgruppen enthaltende Oligomere und Polymere und Verfahren zu ihrer Herstellung |
DE10144815A1 (de) * | 2001-09-12 | 2003-03-27 | Celanese Ventures Gmbh | Protonenleitende Membran und deren Verwendung |
US7196151B2 (en) * | 2001-11-22 | 2007-03-27 | Haering Thomas | Functionalized main chain polymers |
DE10209419A1 (de) | 2002-03-05 | 2003-09-25 | Celanese Ventures Gmbh | Verfahren zur Herstellung einer Polymerelektrolytmembran und deren Anwendung in Brennstoffzellen |
US7846982B2 (en) * | 2002-03-06 | 2010-12-07 | Pemeas Gmbh | Proton conducting electrolyte membrane having reduced methanol permeability and the use thereof in fuel cells |
DE10213540A1 (de) * | 2002-03-06 | 2004-02-19 | Celanese Ventures Gmbh | Lösung aus Vinylphosphonsäure, Verfahren zur Herstellung einer Polymerelektrolytmembran aus Polyvinylphosphaonsäure und deren Anwendung in Brennstoffzellen |
US20050118478A1 (en) | 2002-03-06 | 2005-06-02 | Joachim Kiefer | Mixture comprising sulphonic acid containing vinyl, polymer electrolyte membrane comprising polyvinylsulphonic acid and the use thereof in fuel cells |
JP4638220B2 (ja) * | 2002-04-25 | 2011-02-23 | ビーエーエスエフ フューエル セル ゲゼルシャフト ミット ベシュレンクテル ハフツング | 多層電解質膜 |
DE10220818A1 (de) * | 2002-05-10 | 2003-11-20 | Celanese Ventures Gmbh | Verfahren zur Herstellung einer gepfropften Polymerelektrolytmembran und deren Anwendung in Brennstoffzellen |
DE10220817A1 (de) | 2002-05-10 | 2003-11-27 | Celanese Ventures Gmbh | Verfahren zur Herstellung einer gepfropften Polymerelektrolytmembran und deren Anwendung in Brennstoffzellen |
DE10228657A1 (de) * | 2002-06-27 | 2004-01-15 | Celanese Ventures Gmbh | Protonenleitende Membran und deren Verwendung |
DE10230477A1 (de) * | 2002-07-06 | 2004-01-15 | Celanese Ventures Gmbh | Funktionalisierte Polyazole, Verfahren zu ihrer Herstellung sowie ihre Verwendung |
DE10235358A1 (de) * | 2002-08-02 | 2004-02-12 | Celanese Ventures Gmbh | Protonenleitende Polymermembran umfassend Phosphonsäuregruppen enthaltende Polymere und deren Anwendung in Brennstoffzellen |
US7332530B2 (en) | 2002-08-02 | 2008-02-19 | Celanese Ventures Gmbh | Proton-conducting polymer membrane comprising a polymer with sulphonic acid groups and use thereof in fuel cells |
DE10239701A1 (de) * | 2002-08-29 | 2004-03-11 | Celanese Ventures Gmbh | Polymerfolie auf Basis von Polyazolen und deren Verwendung |
DE10242708A1 (de) * | 2002-09-13 | 2004-05-19 | Celanese Ventures Gmbh | Protonenleitende Membranen und deren Verwendung |
DE10246373A1 (de) | 2002-10-04 | 2004-04-15 | Celanese Ventures Gmbh | Protonenleitende Polymermembran umfassend Sulfonsäuregruppen enthaltende Polyazole und deren Anwendung in Brennstoffzellen |
DE10246461A1 (de) | 2002-10-04 | 2004-04-15 | Celanese Ventures Gmbh | Protonenleitende Polymermembran enthaltend Polyazolblends 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 |
DE10246372A1 (de) * | 2002-10-04 | 2004-04-15 | Celanese Ventures Gmbh | Mit einer Katalysatorschicht beschichtete protonenleitende Polymermembran enthaltend Polyazole und deren Anwendung in Brennstoffzellen |
US7834131B2 (en) * | 2003-07-11 | 2010-11-16 | Basf Fuel Cell Gmbh | Asymmetric polymer film, method for the production and utilization thereof |
WO2005011039A2 (de) * | 2003-07-27 | 2005-02-03 | Pemeas Gmbh | Protonenleitende membran und deren verwendung |
US20080038624A1 (en) * | 2003-09-04 | 2008-02-14 | Jorg Belack | Proton-conducting polymer membrane coated with a catalyst layer, said polymer membrane comprising phosphonic acid polymers, membrane/electrode unit and use thereof in fuel cells |
DE102005020604A1 (de) | 2005-05-03 | 2006-11-16 | Pemeas Gmbh | Brennstoffzellen mit geringerem Gewicht und Volumen |
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2001
- 2001-04-09 DE DE10117686A patent/DE10117686A1/de not_active Withdrawn
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2002
- 2002-04-09 CA CA002443541A patent/CA2443541C/en not_active Expired - Fee Related
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- 2002-04-09 WO PCT/EP2002/003900 patent/WO2002088219A1/de active Application Filing
- 2002-04-09 DK DK02766620.5T patent/DK1379573T3/da active
- 2002-04-09 AT AT02766620T patent/ATE491739T1/de active
- 2002-04-09 KR KR1020037013172A patent/KR100910117B1/ko not_active IP Right Cessation
- 2002-04-09 DE DE50214815T patent/DE50214815D1/de not_active Expired - Lifetime
- 2002-04-09 EP EP02766620A patent/EP1379573B1/de not_active Expired - Lifetime
- 2002-04-09 BR BR0208795-2A patent/BR0208795A/pt not_active Application Discontinuation
- 2002-04-09 CN CNB028079558A patent/CN100503689C/zh not_active Expired - Fee Related
- 2002-04-09 US US10/472,814 patent/US7384552B2/en not_active Expired - Fee Related
- 2002-04-09 EP EP10007141A patent/EP2267059B1/de not_active Expired - Lifetime
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2007
- 2007-10-31 US US11/930,704 patent/US7540984B2/en not_active Expired - Fee Related
- 2007-10-31 US US11/930,764 patent/US7582210B2/en not_active Expired - Fee Related
Non-Patent Citations (2)
Title |
---|
SYNTHESIS AND PROCESSINGOF HETEROCYCLICPOLYMERS ASELECTRONIC,OPTOELECTRONIC ,AND NONLINEAROPTICAL MATERIALS.. OSAHENI J A ET AL.MACROMOLECULES,AMERICAN CHEMICAL SOCIETY,Vol.28 No.4. 1995 |
SYNTHESIS AND PROCESSINGOF HETEROCYCLICPOLYMERS ASELECTRONIC,OPTOELECTRONIC ,AND NONLINEAROPTICAL MATERIALS.. OSAHENI J A ET AL.MACROMOLECULES,AMERICAN CHEMICAL SOCIETY,Vol.28 No.4. 1995 * |
Also Published As
Publication number | Publication date |
---|---|
DK1379573T3 (da) | 2011-04-04 |
JP2005536570A (ja) | 2005-12-02 |
BR0208795A (pt) | 2004-03-09 |
ATE491739T1 (de) | 2011-01-15 |
US20080050514A1 (en) | 2008-02-28 |
US7582210B2 (en) | 2009-09-01 |
WO2002088219A1 (de) | 2002-11-07 |
US7540984B2 (en) | 2009-06-02 |
EP2267059A1 (de) | 2010-12-29 |
DE50214815D1 (de) | 2011-01-27 |
US20040096734A1 (en) | 2004-05-20 |
EP1379573A1 (de) | 2004-01-14 |
US7384552B2 (en) | 2008-06-10 |
MXPA03009184A (es) | 2004-02-17 |
CN1606585A (zh) | 2005-04-13 |
JP4663215B2 (ja) | 2011-04-06 |
KR20040087856A (ko) | 2004-10-15 |
EP2267059B1 (de) | 2012-08-22 |
US20080057358A1 (en) | 2008-03-06 |
CA2443541A1 (en) | 2002-11-07 |
DE10117686A1 (de) | 2002-10-24 |
CA2443541C (en) | 2008-07-15 |
EP1379573B1 (de) | 2010-12-15 |
KR100910117B1 (ko) | 2009-08-03 |
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