JP2008505209A - 固相重合工程が改良された２段階溶融重合法によるポリベンゾイミダゾールの製造方法。 - Google Patents
固相重合工程が改良された２段階溶融重合法によるポリベンゾイミダゾールの製造方法。 Download PDFInfo
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- JP2008505209A JP2008505209A JP2007519239A JP2007519239A JP2008505209A JP 2008505209 A JP2008505209 A JP 2008505209A JP 2007519239 A JP2007519239 A JP 2007519239A JP 2007519239 A JP2007519239 A JP 2007519239A JP 2008505209 A JP2008505209 A JP 2008505209A
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- molecular weight
- high molecular
- producing
- melt polymerization
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- 238000004519 manufacturing process Methods 0.000 title claims abstract description 25
- 229920002480 polybenzimidazole Polymers 0.000 title claims description 43
- 238000006116 polymerization reaction Methods 0.000 title claims description 40
- 239000004693 Polybenzimidazole Substances 0.000 title claims description 35
- 238000000034 method Methods 0.000 title description 26
- 239000007790 solid phase Substances 0.000 title description 3
- 238000006243 chemical reaction Methods 0.000 claims abstract description 72
- 238000003756 stirring Methods 0.000 claims abstract description 42
- KSSJBGNOJJETTC-UHFFFAOYSA-N COC1=C(C=CC=C1)N(C1=CC=2C3(C4=CC(=CC=C4C=2C=C1)N(C1=CC=C(C=C1)OC)C1=C(C=CC=C1)OC)C1=CC(=CC=C1C=1C=CC(=CC=13)N(C1=CC=C(C=C1)OC)C1=C(C=CC=C1)OC)N(C1=CC=C(C=C1)OC)C1=C(C=CC=C1)OC)C1=CC=C(C=C1)OC Chemical compound COC1=C(C=CC=C1)N(C1=CC=2C3(C4=CC(=CC=C4C=2C=C1)N(C1=CC=C(C=C1)OC)C1=C(C=CC=C1)OC)C1=CC(=CC=C1C=1C=CC(=CC=13)N(C1=CC=C(C=C1)OC)C1=C(C=CC=C1)OC)N(C1=CC=C(C=C1)OC)C1=C(C=CC=C1)OC)C1=CC=C(C=C1)OC KSSJBGNOJJETTC-UHFFFAOYSA-N 0.000 claims abstract description 19
- 239000006260 foam Substances 0.000 claims abstract description 14
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 6
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims abstract description 5
- 239000011541 reaction mixture Substances 0.000 claims abstract description 5
- 239000002245 particle Substances 0.000 claims description 40
- 125000003118 aryl group Chemical group 0.000 claims description 27
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 23
- 239000001257 hydrogen Substances 0.000 claims description 13
- 229910052739 hydrogen Inorganic materials 0.000 claims description 13
- 150000001875 compounds Chemical class 0.000 claims description 11
- 125000000217 alkyl group Chemical group 0.000 claims description 10
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 10
- 238000010438 heat treatment Methods 0.000 claims description 10
- 239000001301 oxygen Substances 0.000 claims description 10
- 229910052760 oxygen Inorganic materials 0.000 claims description 10
- FHESUNXRPBHDQM-UHFFFAOYSA-N diphenyl benzene-1,3-dicarboxylate Chemical group C=1C=CC(C(=O)OC=2C=CC=CC=2)=CC=1C(=O)OC1=CC=CC=C1 FHESUNXRPBHDQM-UHFFFAOYSA-N 0.000 claims description 9
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 8
- 125000002947 alkylene group Chemical group 0.000 claims description 6
- 150000001412 amines Chemical group 0.000 claims description 6
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 claims description 5
- 125000002029 aromatic hydrocarbon group Chemical group 0.000 claims description 5
- 150000003254 radicals Chemical class 0.000 claims description 5
- 239000000376 reactant Substances 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 3
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 claims 4
- 229910052753 mercury Inorganic materials 0.000 claims 4
- 229920006158 high molecular weight polymer Polymers 0.000 claims 1
- 238000011049 filling Methods 0.000 abstract description 2
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 abstract 3
- 229920000642 polymer Polymers 0.000 description 37
- 239000000047 product Substances 0.000 description 19
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 11
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 10
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 8
- 239000000203 mixture Substances 0.000 description 8
- -1 phenylphenyl radicals Chemical class 0.000 description 8
- 238000012360 testing method Methods 0.000 description 8
- 125000004432 carbon atom Chemical group C* 0.000 description 7
- 238000009826 distribution Methods 0.000 description 7
- 238000005227 gel permeation chromatography Methods 0.000 description 7
- 239000000178 monomer Substances 0.000 description 7
- 238000005481 NMR spectroscopy Methods 0.000 description 6
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 5
- KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 description 5
- 206010001497 Agitation Diseases 0.000 description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical group C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 4
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical group C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical group N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 4
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical group C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 4
- 150000002148 esters Chemical class 0.000 description 4
- 238000001125 extrusion Methods 0.000 description 4
- 239000011521 glass Substances 0.000 description 4
- 239000011261 inert gas Substances 0.000 description 4
- 238000002844 melting Methods 0.000 description 4
- 230000008018 melting Effects 0.000 description 4
- 230000035484 reaction time Effects 0.000 description 4
- KSFAWAYSJUPRED-UHFFFAOYSA-N 5-phenylbenzene-1,2,3,4-tetramine Chemical group NC1=C(N)C(N)=CC(C=2C=CC=CC=2)=C1N KSFAWAYSJUPRED-UHFFFAOYSA-N 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 238000013019 agitation Methods 0.000 description 3
- 150000001991 dicarboxylic acids Chemical class 0.000 description 3
- VNGOYPQMJFJDLV-UHFFFAOYSA-N dimethyl benzene-1,3-dicarboxylate Chemical compound COC(=O)C1=CC=CC(C(=O)OC)=C1 VNGOYPQMJFJDLV-UHFFFAOYSA-N 0.000 description 3
- 239000000835 fiber Substances 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 150000002431 hydrogen Chemical class 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 238000012546 transfer Methods 0.000 description 3
- MGADZUXDNSDTHW-UHFFFAOYSA-N 2H-pyran Chemical group C1OC=CC=C1 MGADZUXDNSDTHW-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-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
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Chemical group C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 description 2
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 125000005907 alkyl ester group Chemical group 0.000 description 2
- 235000010290 biphenyl Nutrition 0.000 description 2
- 239000004305 biphenyl Substances 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
- 229920001577 copolymer Polymers 0.000 description 2
- 150000005690 diesters Chemical class 0.000 description 2
- GWZCCUDJHOGOSO-UHFFFAOYSA-N diphenic acid Chemical compound OC(=O)C1=CC=CC=C1C1=CC=CC=C1C(O)=O GWZCCUDJHOGOSO-UHFFFAOYSA-N 0.000 description 2
- 239000000839 emulsion Substances 0.000 description 2
- 239000000446 fuel Substances 0.000 description 2
- 239000008240 homogeneous mixture Substances 0.000 description 2
- QQVIHTHCMHWDBS-UHFFFAOYSA-L isophthalate(2-) Chemical compound [O-]C(=O)C1=CC=CC(C([O-])=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-L 0.000 description 2
- 230000014759 maintenance of location Effects 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 2
- 239000004926 polymethyl methacrylate Substances 0.000 description 2
- 238000012545 processing Methods 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 239000002002 slurry Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000004611 spectroscopical analysis Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 229930192474 thiophene Chemical group 0.000 description 2
- RQOKAVXYXISUJQ-UHFFFAOYSA-N 1h-benzimidazole;methane Chemical compound C.C1=CC=C2NC=NC2=C1 RQOKAVXYXISUJQ-UHFFFAOYSA-N 0.000 description 1
- XFEGRFIENDJTCK-UHFFFAOYSA-N 2-phenyl-2,3-dihydroindene-1,1-dicarboxylic acid Chemical compound C1C2=CC=CC=C2C(C(=O)O)(C(O)=O)C1C1=CC=CC=C1 XFEGRFIENDJTCK-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
- 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 description 1
- 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 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- AFCARXCZXQIEQB-UHFFFAOYSA-N N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C(CCNC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)N1CC2=C(CC1)NN=N2 AFCARXCZXQIEQB-UHFFFAOYSA-N 0.000 description 1
- QAOWNCQODCNURD-ZSJDYOACSA-N Sulfuric acid-d2 Chemical compound [2H]OS(=O)(=O)O[2H] QAOWNCQODCNURD-ZSJDYOACSA-N 0.000 description 1
- PQFYBBYXXJFPKM-UHFFFAOYSA-N [S-][n+]1c[nH]c2ccccc12 Chemical compound [S-][n+]1c[nH]c2ccccc12 PQFYBBYXXJFPKM-UHFFFAOYSA-N 0.000 description 1
- 230000032683 aging Effects 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- 125000003710 aryl alkyl group Chemical group 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- ANUAIBBBDSEVKN-UHFFFAOYSA-N benzene-1,2,4,5-tetramine Chemical compound NC1=CC(N)=C(N)C=C1N ANUAIBBBDSEVKN-UHFFFAOYSA-N 0.000 description 1
- BUXXHSFXBVGJBL-UHFFFAOYSA-N benzene-1,3-dicarboxylic acid;1,1'-biphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1.OC(=O)C1=CC=CC(C(O)=O)=C1 BUXXHSFXBVGJBL-UHFFFAOYSA-N 0.000 description 1
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 description 1
- 125000006267 biphenyl group Chemical group 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 210000004027 cell Anatomy 0.000 description 1
- 210000000170 cell membrane Anatomy 0.000 description 1
- 238000012512 characterization method Methods 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 238000010954 commercial manufacturing process Methods 0.000 description 1
- 239000013065 commercial product Substances 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 229920006037 cross link polymer Polymers 0.000 description 1
- 238000004132 cross linking Methods 0.000 description 1
- 150000001923 cyclic compounds Chemical class 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 150000004985 diamines Chemical class 0.000 description 1
- 125000001142 dicarboxylic acid group Chemical group 0.000 description 1
- 229910001873 dinitrogen Inorganic materials 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 230000005484 gravity Effects 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 230000007257 malfunction Effects 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- 238000003801 milling Methods 0.000 description 1
- 238000012544 monitoring process Methods 0.000 description 1
- UIMPSNPKHVULAQ-UHFFFAOYSA-N naphthalene-1,2,5,6-tetramine Chemical compound NC1=C(N)C=CC2=C(N)C(N)=CC=C21 UIMPSNPKHVULAQ-UHFFFAOYSA-N 0.000 description 1
- VAWFFNJAPKXVPH-UHFFFAOYSA-N naphthalene-1,6-dicarboxylic acid Chemical compound OC(=O)C1=CC=CC2=CC(C(=O)O)=CC=C21 VAWFFNJAPKXVPH-UHFFFAOYSA-N 0.000 description 1
- DKYADULMEONPQX-UHFFFAOYSA-N naphthalene-2,3,6,7-tetramine Chemical compound NC1=C(N)C=C2C=C(N)C(N)=CC2=C1 DKYADULMEONPQX-UHFFFAOYSA-N 0.000 description 1
- 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 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 238000011056 performance test Methods 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 238000006068 polycondensation reaction Methods 0.000 description 1
- 229920000098 polyolefin Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000011973 solid acid Substances 0.000 description 1
- 230000003595 spectral effect Effects 0.000 description 1
- 238000009987 spinning Methods 0.000 description 1
- 230000003068 static effect Effects 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 150000003457 sulfones Chemical class 0.000 description 1
- 150000003568 thioethers Chemical class 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
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US10/884,103 US7060782B2 (en) | 2004-07-02 | 2004-07-02 | Process for a two stage melt polymerization for the production of polybenzimidazole having an improved solid state polymerization |
| PCT/US2005/020196 WO2006014211A1 (en) | 2004-07-02 | 2005-06-09 | A process for a two stage melt polymerization for the production of polybenzimidazole having an improved solid state polymerization |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2008505209A true JP2008505209A (ja) | 2008-02-21 |
| JP2008505209A5 JP2008505209A5 (enExample) | 2009-12-24 |
Family
ID=35514882
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2007519239A Pending JP2008505209A (ja) | 2004-07-02 | 2005-06-09 | 固相重合工程が改良された２段階溶融重合法によるポリベンゾイミダゾールの製造方法。 |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US7060782B2 (enExample) |
| EP (1) | EP1769016B1 (enExample) |
| JP (1) | JP2008505209A (enExample) |
| CN (1) | CN100580007C (enExample) |
| RU (1) | RU2343168C2 (enExample) |
| WO (1) | WO2006014211A1 (enExample) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2009500509A (ja) * | 2005-07-11 | 2009-01-08 | ピービーアイ・パフォーマンス・プロダクツ・インコーポレーテッド | ポリベンズイミダゾールの製造のための２段階溶融重合法 |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7060782B2 (en) * | 2004-07-02 | 2006-06-13 | Pbi Performance Products, Inc. | Process for a two stage melt polymerization for the production of polybenzimidazole having an improved solid state polymerization |
| US7038007B2 (en) * | 2004-07-02 | 2006-05-02 | Pbi Performance Products, Inc. | Process for a continuous polymerization for the production of high molecular weight polybenzimidazole |
| US7148314B2 (en) * | 2004-07-07 | 2006-12-12 | General Electric Company | Process for preparation of functionalized polyimides |
| DE102006010705A1 (de) * | 2006-03-08 | 2007-09-13 | Sartorius Ag | Hybridmembranen, Verfahren zur Herstellung der Hybridmembranen und Brennstoffzellen unter Verwendung derartiger Hybridmembranen |
| US7834130B2 (en) * | 2007-02-22 | 2010-11-16 | Pbi Performance Products, Inc. | Process for the production of polybenzimidazole from a tetraminobiphenyl and an isophthalic acid |
| US8642722B2 (en) * | 2009-05-15 | 2014-02-04 | Iucf-Hyu (Industry-University Cooperation Foundation Hanyang University) | Preparation method of polybenzimidazole |
| CN103709403A (zh) * | 2014-01-14 | 2014-04-09 | 北京中聚科技有限公司 | 聚苯并咪唑的程序升温式熔融聚合法 |
Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS59179525A (ja) * | 1983-03-21 | 1984-10-12 | ヘキスト・セラニーズ・コーポレーション | 高分子量ポリベンゾイミダゾ−ルの製法 |
| JPS6166719A (ja) * | 1984-08-31 | 1986-04-05 | ヘキスト セラニーズ コーポレーシヨン | ジカルボン酸成分からポリベンヅイミダゾールを製造する２工程法 |
| JPS6322833A (ja) * | 1986-06-05 | 1988-01-30 | ヘキスト セラニーズ コーポレーション | ２段階ポリベンズイミダゾ−ル法の改良 |
| JPH08188647A (ja) * | 1994-10-04 | 1996-07-23 | Hoechst Celanese Corp | 二段階溶融重合法によるポリベンズイミダゾールの製造法 |
| JPH09506117A (ja) * | 1993-09-14 | 1997-06-17 | ベインズ ハーディング リミテッド | プラスチックに適した難燃剤 |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4672104A (en) | 1984-08-31 | 1987-06-09 | Celanese Corporation | Two stage polybenzimidazole process and product |
| US4717764A (en) | 1985-02-22 | 1988-01-05 | Celanese Corporation | Two stage melt polymerization process for making polymers containing aromatic amide groups |
| US5171829A (en) * | 1986-04-25 | 1992-12-15 | Kanegafuchi Kagaku Kogyo Kabushiki Kaisha | Copolymeric and amphiphilic polyimide precursor, process for preparing the same and thin film |
| US7060782B2 (en) * | 2004-07-02 | 2006-06-13 | Pbi Performance Products, Inc. | Process for a two stage melt polymerization for the production of polybenzimidazole having an improved solid state polymerization |
| US7038007B2 (en) * | 2004-07-02 | 2006-05-02 | Pbi Performance Products, Inc. | Process for a continuous polymerization for the production of high molecular weight polybenzimidazole |
-
2004
- 2004-07-02 US US10/884,103 patent/US7060782B2/en not_active Expired - Lifetime
-
2005
- 2005-06-09 EP EP05759185A patent/EP1769016B1/en not_active Expired - Lifetime
- 2005-06-09 RU RU2007104017/04A patent/RU2343168C2/ru active
- 2005-06-09 JP JP2007519239A patent/JP2008505209A/ja active Pending
- 2005-06-09 WO PCT/US2005/020196 patent/WO2006014211A1/en not_active Ceased
- 2005-06-09 CN CN200580022313A patent/CN100580007C/zh not_active Expired - Lifetime
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS59179525A (ja) * | 1983-03-21 | 1984-10-12 | ヘキスト・セラニーズ・コーポレーション | 高分子量ポリベンゾイミダゾ−ルの製法 |
| JPS6166719A (ja) * | 1984-08-31 | 1986-04-05 | ヘキスト セラニーズ コーポレーシヨン | ジカルボン酸成分からポリベンヅイミダゾールを製造する２工程法 |
| JPS6322833A (ja) * | 1986-06-05 | 1988-01-30 | ヘキスト セラニーズ コーポレーション | ２段階ポリベンズイミダゾ−ル法の改良 |
| JPH09506117A (ja) * | 1993-09-14 | 1997-06-17 | ベインズ ハーディング リミテッド | プラスチックに適した難燃剤 |
| JPH08188647A (ja) * | 1994-10-04 | 1996-07-23 | Hoechst Celanese Corp | 二段階溶融重合法によるポリベンズイミダゾールの製造法 |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2009500509A (ja) * | 2005-07-11 | 2009-01-08 | ピービーアイ・パフォーマンス・プロダクツ・インコーポレーテッド | ポリベンズイミダゾールの製造のための２段階溶融重合法 |
Also Published As
| Publication number | Publication date |
|---|---|
| US7060782B2 (en) | 2006-06-13 |
| EP1769016B1 (en) | 2012-10-24 |
| WO2006014211A1 (en) | 2006-02-09 |
| EP1769016A4 (en) | 2010-02-17 |
| RU2343168C2 (ru) | 2009-01-10 |
| EP1769016A1 (en) | 2007-04-04 |
| CN1980982A (zh) | 2007-06-13 |
| CN100580007C (zh) | 2010-01-13 |
| RU2007104017A (ru) | 2008-08-10 |
| US20060004182A1 (en) | 2006-01-05 |
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