JP3527740B2 - ピリドビスイミダゾールに基く剛直なロッドポリマー - Google Patents
ピリドビスイミダゾールに基く剛直なロッドポリマーInfo
- Publication number
- JP3527740B2 JP3527740B2 JP52386794A JP52386794A JP3527740B2 JP 3527740 B2 JP3527740 B2 JP 3527740B2 JP 52386794 A JP52386794 A JP 52386794A JP 52386794 A JP52386794 A JP 52386794A JP 3527740 B2 JP3527740 B2 JP 3527740B2
- Authority
- JP
- Japan
- Prior art keywords
- polymer
- acid
- fiber
- rod polymer
- pyridobisimidazole
- 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 - Lifetime
Links
- 229920003252 rigid-rod polymer Polymers 0.000 title claims abstract description 12
- 229920000642 polymer Polymers 0.000 claims abstract description 76
- 239000000203 mixture Substances 0.000 claims abstract description 27
- 239000000835 fiber Substances 0.000 claims description 70
- 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 27
- HOWDQPJMFFMJSR-UHFFFAOYSA-N pyridine-2,3,4,5-tetramine Chemical compound NC1=CN=C(N)C(N)=C1N HOWDQPJMFFMJSR-UHFFFAOYSA-N 0.000 claims description 22
- 238000000034 method Methods 0.000 claims description 21
- -1 2,5-dihydroxy-p- Phenylene Chemical group 0.000 claims description 20
- 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
- 229920000137 polyphosphoric acid Polymers 0.000 claims description 15
- 229910019142 PO4 Inorganic materials 0.000 claims description 11
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims description 10
- 239000010452 phosphate Substances 0.000 claims description 10
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims description 7
- RRDBXTBGGXLZHD-UHFFFAOYSA-N benzene-1,4-dicarboperoxoic acid Chemical compound OOC(=O)C1=CC=C(C(=O)OO)C=C1 RRDBXTBGGXLZHD-UHFFFAOYSA-N 0.000 claims description 7
- 125000000732 arylene group Chemical group 0.000 claims description 6
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical group OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 claims description 4
- 229940098779 methanesulfonic acid Drugs 0.000 claims description 3
- 239000002904 solvent Substances 0.000 claims description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 2
- LVPMIMZXDYBCDF-UHFFFAOYSA-N isocinchomeronic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)N=C1 LVPMIMZXDYBCDF-UHFFFAOYSA-N 0.000 claims 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 claims description 2
- 230000000379 polymerizing effect Effects 0.000 claims description 2
- CYVYLVVUKPNYKL-UHFFFAOYSA-N quinoline-2,6-dicarboxylic acid Chemical compound N1=C(C(O)=O)C=CC2=CC(C(=O)O)=CC=C21 CYVYLVVUKPNYKL-UHFFFAOYSA-N 0.000 claims description 2
- 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 1
- 235000012438 extruded product Nutrition 0.000 claims 1
- 238000002360 preparation method Methods 0.000 abstract description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 22
- 238000003756 stirring Methods 0.000 description 18
- 238000009987 spinning Methods 0.000 description 17
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 16
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 16
- 239000000243 solution Substances 0.000 description 13
- 238000006116 polymerization reaction Methods 0.000 description 12
- 238000010438 heat treatment Methods 0.000 description 11
- 239000002002 slurry Substances 0.000 description 11
- 238000012360 testing method Methods 0.000 description 11
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 10
- 235000021317 phosphate Nutrition 0.000 description 10
- 239000000047 product Substances 0.000 description 10
- 229910021529 ammonia Inorganic materials 0.000 description 8
- 229910052757 nitrogen Inorganic materials 0.000 description 8
- 238000011282 treatment Methods 0.000 description 7
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 6
- 230000015271 coagulation Effects 0.000 description 6
- 238000005345 coagulation Methods 0.000 description 6
- 238000009826 distribution Methods 0.000 description 6
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 5
- 229920001519 homopolymer Polymers 0.000 description 5
- 239000000463 material Substances 0.000 description 5
- 229910052760 oxygen Inorganic materials 0.000 description 5
- 239000001301 oxygen Substances 0.000 description 5
- 150000003839 salts Chemical class 0.000 description 5
- 238000005406 washing Methods 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 238000005260 corrosion Methods 0.000 description 4
- 230000007797 corrosion Effects 0.000 description 4
- 239000012299 nitrogen atmosphere Substances 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 238000002441 X-ray diffraction Methods 0.000 description 3
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 229920001577 copolymer Polymers 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 238000005259 measurement Methods 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- 239000000178 monomer Substances 0.000 description 3
- 229920000927 poly(p-phenylene benzobisoxazole) Polymers 0.000 description 3
- 229920003366 poly(p-phenylene terephthalamide) Polymers 0.000 description 3
- 230000000630 rising effect Effects 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 description 2
- FNRGQEBYFUICMY-UHFFFAOYSA-N O.Cl.Cl.Cl.N1CCCC=C1 Chemical compound O.Cl.Cl.Cl.N1CCCC=C1 FNRGQEBYFUICMY-UHFFFAOYSA-N 0.000 description 2
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 238000013019 agitation Methods 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 238000005187 foaming Methods 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 229920000620 organic polymer Polymers 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 238000012545 processing Methods 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 238000010998 test method Methods 0.000 description 2
- 238000002166 wet spinning Methods 0.000 description 2
- 238000004804 winding Methods 0.000 description 2
- OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 description 1
- PDQRQJVPEFGVRK-UHFFFAOYSA-N 2,1,3-benzothiadiazole Chemical compound C1=CC=CC2=NSN=C21 PDQRQJVPEFGVRK-UHFFFAOYSA-N 0.000 description 1
- XRASRVJYOMVDNP-UHFFFAOYSA-N 4-(7-azabicyclo[4.1.0]hepta-1,3,5-triene-7-carbonyl)benzamide Chemical compound C1=CC(C(=O)N)=CC=C1C(=O)N1C2=CC=CC=C21 XRASRVJYOMVDNP-UHFFFAOYSA-N 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- 101100025412 Arabidopsis thaliana XI-A gene Proteins 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 1
- 238000000692 Student's t-test Methods 0.000 description 1
- 229920000561 Twaron Polymers 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 239000012670 alkaline solution Substances 0.000 description 1
- 239000000908 ammonium hydroxide Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- 238000004364 calculation method Methods 0.000 description 1
- 238000011088 calibration curve Methods 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 230000001143 conditioned effect Effects 0.000 description 1
- 238000010924 continuous production Methods 0.000 description 1
- 230000008602 contraction Effects 0.000 description 1
- 230000002596 correlated effect Effects 0.000 description 1
- 230000000875 corresponding effect Effects 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000007872 degassing Methods 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 229940117389 dichlorobenzene Drugs 0.000 description 1
- 238000002845 discoloration Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000001125 extrusion Methods 0.000 description 1
- 239000012065 filter cake Substances 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 229920006158 high molecular weight polymer Polymers 0.000 description 1
- JKXCZYCVHPKTPK-UHFFFAOYSA-N hydrate;trihydrochloride Chemical compound O.Cl.Cl.Cl JKXCZYCVHPKTPK-UHFFFAOYSA-N 0.000 description 1
- 238000007654 immersion Methods 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 230000001788 irregular Effects 0.000 description 1
- 238000012417 linear regression Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- AASHWPQBGZGELE-UHFFFAOYSA-N phosphoric acid pyridine-2,3,4,5-tetramine Chemical compound OP(O)(O)=O.NC1=CN=C(N)C(N)=C1N AASHWPQBGZGELE-UHFFFAOYSA-N 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 229920005594 polymer fiber Polymers 0.000 description 1
- IAYUQKZZQKUOFL-UHFFFAOYSA-N pyridine-2,3,5,6-tetramine Chemical compound NC1=CC(N)=C(N)N=C1N IAYUQKZZQKUOFL-UHFFFAOYSA-N 0.000 description 1
- LMMZYESITFIBIM-UHFFFAOYSA-N pyridine-2,3,5,6-tetramine;hydrate;trihydrochloride Chemical compound O.Cl.Cl.Cl.NC1=CC(N)=C(N)N=C1N LMMZYESITFIBIM-UHFFFAOYSA-N 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 238000005728 strengthening Methods 0.000 description 1
- 238000012353 t test Methods 0.000 description 1
- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 239000004762 twaron Substances 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
Classifications
-
- 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
- C08G75/00—Macromolecular compounds obtained by reactions forming a linkage containing sulfur with or without nitrogen, oxygen, or carbon in the main chain of the macromolecule
- C08G75/32—Polythiazoles; Polythiadiazoles
-
- 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
- C08J5/18—Manufacture of films or sheets
-
- D—TEXTILES; PAPER
- D01—NATURAL OR MAN-MADE THREADS OR FIBRES; SPINNING
- D01F—CHEMICAL FEATURES IN THE MANUFACTURE OF ARTIFICIAL FILAMENTS, THREADS, FIBRES, BRISTLES OR RIBBONS; APPARATUS SPECIALLY ADAPTED FOR THE MANUFACTURE OF CARBON FILAMENTS
- D01F6/00—Monocomponent artificial filaments or the like of synthetic polymers; Manufacture thereof
- D01F6/58—Monocomponent artificial filaments or the like of synthetic polymers; Manufacture thereof from homopolycondensation products
- D01F6/74—Monocomponent artificial filaments or the like of synthetic polymers; Manufacture thereof from homopolycondensation products from polycondensates of cyclic compounds, e.g. polyimides, polybenzimidazoles
Landscapes
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- General Chemical & Material Sciences (AREA)
- Textile Engineering (AREA)
- Manufacturing & Machinery (AREA)
- Materials Engineering (AREA)
- Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
- Artificial Filaments (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Manufacture Of Macromolecular Shaped Articles (AREA)
- Spinning Methods And Devices For Manufacturing Artificial Fibers (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Dental Preparations (AREA)
- Other Resins Obtained By Reactions Not Involving Carbon-To-Carbon Unsaturated Bonds (AREA)
- Polyoxymethylene Polymers And Polymers With Carbon-To-Carbon Bonds (AREA)
- Polymers With Sulfur, Phosphorus Or Metals In The Main Chain (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| NL9300722 | 1993-04-28 | ||
| NL9300722 | 1993-04-28 | ||
| PCT/EP1994/001302 WO1994025506A1 (en) | 1993-04-28 | 1994-04-22 | Rigid rod polymer based on pyridobisimidazole |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH08509516A JPH08509516A (ja) | 1996-10-08 |
| JP3527740B2 true JP3527740B2 (ja) | 2004-05-17 |
Family
ID=19862338
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP52386794A Expired - Lifetime JP3527740B2 (ja) | 1993-04-28 | 1994-04-22 | ピリドビスイミダゾールに基く剛直なロッドポリマー |
Country Status (14)
| Country | Link |
|---|---|
| US (1) | US5674969A (OSRAM) |
| EP (1) | EP0696297B1 (OSRAM) |
| JP (1) | JP3527740B2 (OSRAM) |
| KR (1) | KR100306676B1 (OSRAM) |
| CN (1) | CN1041208C (OSRAM) |
| AT (1) | ATE169317T1 (OSRAM) |
| CA (1) | CA2161663C (OSRAM) |
| DE (1) | DE69412250T2 (OSRAM) |
| DK (1) | DK0696297T3 (OSRAM) |
| ES (1) | ES2120042T3 (OSRAM) |
| MX (1) | MXPA94003094A (OSRAM) |
| TW (1) | TW283716B (OSRAM) |
| WO (1) | WO1994025506A1 (OSRAM) |
| ZA (1) | ZA942967B (OSRAM) |
Families Citing this family (148)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL1000360C2 (nl) * | 1995-05-15 | 1996-11-18 | Akzo Nobel Nv | Werkwijze ter bereiding van pyridine-2, 6-diamines |
| US5945537A (en) * | 1995-09-19 | 1999-08-31 | Akzo Nobel N.V. | Nitration of pyridine-2, 6-diamines |
| NL1001628C2 (nl) * | 1995-11-10 | 1997-05-13 | Akzo Nobel Nv | Werkwijze voor de tweevoudige carboxylering van dihydrische fenolen en meer in het bijzonder ter bereiding van 2,5-dihydroxytereftaalzuur. |
| WO1999027169A1 (en) * | 1997-11-21 | 1999-06-03 | Akzo Nobel N.V. | Flame-retardant materials |
| DE10209419A1 (de) * | 2002-03-05 | 2003-09-25 | Celanese Ventures Gmbh | Verfahren zur Herstellung einer Polymerelektrolytmembran 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 |
| 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 |
| DK1483316T3 (da) * | 2002-03-06 | 2007-12-27 | Pemeas Gmbh | Protonledende elektrolytmembran med reduceret methanolpermeabilitet og anvendelse deraf til brændselsceller |
| CA2483015A1 (en) * | 2002-04-25 | 2003-11-06 | Pemeas Gmbh | Multilayer electrolyte membrane |
| DE10220817A1 (de) * | 2002-05-10 | 2003-11-27 | Celanese Ventures Gmbh | Verfahren zur Herstellung einer gepfropften Polymerelektrolytmembran und deren Anwendung in Brennstoffzellen |
| AU2003279783B8 (en) * | 2002-06-27 | 2008-04-03 | Teijin Aramid B.V. | Process for obtaining a synthetic organic aromatic heterocyclic rod fiber or film with high tensile strength and/or modulus |
| DE10230477A1 (de) * | 2002-07-06 | 2004-01-15 | Celanese Ventures Gmbh | Funktionalisierte Polyazole, Verfahren zu ihrer Herstellung sowie ihre Verwendung |
| KR20050036964A (ko) | 2002-08-02 | 2005-04-20 | 페메아스 게엠베하 | 술폰산기를 함유하는 고분자로 이루어진 양성자 전도성고분자막 및 연료전지에서 이의 사용방법 |
| 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 |
| KR20050114630A (ko) | 2003-02-27 | 2005-12-06 | 스티븐 더블유. 포키스 | 방향족 아미드 중합체 시스템 및 그 제조방법 |
| JP4875489B2 (ja) | 2003-07-27 | 2012-02-15 | ベーアーエスエフ フューエル セル ゲーエムベーハー | プロトン伝導性膜およびその使用 |
| EP1739115A4 (en) * | 2004-04-14 | 2010-07-07 | Teijin Ltd | STEEL HETEROCYLIC POLYMER, METHOD OF MANUFACTURING THEREOF AND FIBER |
| EP1614778A1 (en) * | 2004-07-08 | 2006-01-11 | Magellan Systems International, LLC | Process for obtaining a synthetic organic aromatic heterocyclic rod fiber or film with high tensile strength and/or modulus |
| JP4583874B2 (ja) | 2004-10-20 | 2010-11-17 | 三星エスディアイ株式会社 | プロトン伝導性固体高分子電解質膜および燃料電池 |
| US7288493B2 (en) * | 2005-01-18 | 2007-10-30 | Honeywell International Inc. | Body armor with improved knife-stab resistance formed from flexible composites |
| US7833644B2 (en) * | 2005-03-17 | 2010-11-16 | Teijin Limited | Electrolytic membrane |
| CN101238248B (zh) * | 2005-03-28 | 2011-07-27 | 纳幕尔杜邦公司 | 制备聚芳并唑纱的方法 |
| US7683157B2 (en) * | 2005-03-28 | 2010-03-23 | E.I. Du Pont De Nemours And Company | Process for the production of polyarenazole polymer |
| WO2006105230A1 (en) * | 2005-03-28 | 2006-10-05 | E. I. Du Pont De Nemours And Company | Process for the production of polyareneazole polymer |
| CN101203637B (zh) * | 2005-03-28 | 2010-11-17 | 纳幕尔杜邦公司 | 水解纺成纱线中的多磷酸的方法 |
| WO2006105227A1 (en) * | 2005-03-28 | 2006-10-05 | E. I. Du Pont De Nemours And Company | Thermal processes for increasing polyareneazole inherent viscosities |
| US7906613B2 (en) * | 2005-03-28 | 2011-03-15 | Magellan Systems International, Llc | Process for removing cations from polyareneazole fiber |
| WO2006105228A1 (en) * | 2005-03-28 | 2006-10-05 | E. I. Du Pont De Nemours And Company | High inherent viscosity polymers and fibers therefrom |
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| CH463537A (de) * | 1964-09-02 | 1968-10-15 | Alpine Chemische Ag | Verfahren zur Herstellung von 2,5-Dihydroxy-terephthalsäure |
| US4079039A (en) * | 1974-03-04 | 1978-03-14 | Horizons Research Incorporated | Polyheterocyclic polymers derived from substituted tetraamino pyridines |
| US4002679A (en) * | 1974-08-07 | 1977-01-11 | The United States Of America As Represented By The Secretary Of The Air Force | Preparation of polybenzimidazoles |
| US4533692A (en) * | 1982-09-17 | 1985-08-06 | Sri International | Liquid crystalline polymer compositions, process, and products |
| US5041522A (en) * | 1990-03-23 | 1991-08-20 | The United States Of America As Represented By The Secretary Of The Air Force | Dihydroxy-pendant rigid-rod benzobisazole polymer |
| US5039778A (en) * | 1990-03-23 | 1991-08-13 | The United States Of America As Represented By The Secretary Of The Air Force | Dihydroxy-pendant rigid-rod benzobisazole copolymer |
| US5136012A (en) * | 1990-03-23 | 1992-08-04 | United States Of America As Represented By The Secretary Of The Air Force | Dihydroxy-pendant rigid-rod benzobisazole copolymer |
-
1994
- 1994-04-22 DE DE69412250T patent/DE69412250T2/de not_active Expired - Lifetime
- 1994-04-22 US US08/535,225 patent/US5674969A/en not_active Expired - Lifetime
- 1994-04-22 DK DK94915120T patent/DK0696297T3/da active
- 1994-04-22 AT AT94915120T patent/ATE169317T1/de not_active IP Right Cessation
- 1994-04-22 ES ES94915120T patent/ES2120042T3/es not_active Expired - Lifetime
- 1994-04-22 CA CA002161663A patent/CA2161663C/en not_active Expired - Fee Related
- 1994-04-22 WO PCT/EP1994/001302 patent/WO1994025506A1/en not_active Ceased
- 1994-04-22 EP EP94915120A patent/EP0696297B1/en not_active Expired - Lifetime
- 1994-04-22 JP JP52386794A patent/JP3527740B2/ja not_active Expired - Lifetime
- 1994-04-22 KR KR1019950704414A patent/KR100306676B1/ko not_active Expired - Lifetime
- 1994-04-22 CN CN94191918A patent/CN1041208C/zh not_active Expired - Lifetime
- 1994-04-26 TW TW083103743A patent/TW283716B/zh active
- 1994-04-28 MX MXPA94003094A patent/MXPA94003094A/es active IP Right Grant
- 1994-04-29 ZA ZA942967A patent/ZA942967B/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| EP0696297B1 (en) | 1998-08-05 |
| WO1994025506A1 (en) | 1994-11-10 |
| KR100306676B1 (ko) | 2001-11-30 |
| EP0696297A1 (en) | 1996-02-14 |
| ES2120042T3 (es) | 1998-10-16 |
| US5674969A (en) | 1997-10-07 |
| ATE169317T1 (de) | 1998-08-15 |
| CA2161663C (en) | 2005-02-15 |
| KR960701925A (ko) | 1996-03-28 |
| CN1121728A (zh) | 1996-05-01 |
| DK0696297T3 (da) | 1999-05-10 |
| CA2161663A1 (en) | 1994-11-10 |
| TW283716B (OSRAM) | 1996-08-21 |
| JPH08509516A (ja) | 1996-10-08 |
| DE69412250D1 (de) | 1998-09-10 |
| MXPA94003094A (es) | 2003-11-18 |
| CN1041208C (zh) | 1998-12-16 |
| ZA942967B (en) | 1995-01-19 |
| DE69412250T2 (de) | 1999-02-11 |
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