JP4520860B2 - 高分子量ポリアゾール - Google Patents
高分子量ポリアゾール Download PDFInfo
- Publication number
- JP4520860B2 JP4520860B2 JP2004559737A JP2004559737A JP4520860B2 JP 4520860 B2 JP4520860 B2 JP 4520860B2 JP 2004559737 A JP2004559737 A JP 2004559737A JP 2004559737 A JP2004559737 A JP 2004559737A JP 4520860 B2 JP4520860 B2 JP 4520860B2
- Authority
- JP
- Japan
- Prior art keywords
- acid
- aromatic
- producing
- polymer according
- polynuclear
- 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
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- 229920000642 polymer Polymers 0.000 claims description 44
- 125000003118 aryl group Chemical group 0.000 claims description 37
- 125000001072 heteroaryl group Chemical group 0.000 claims description 26
- 238000004519 manufacturing process Methods 0.000 claims description 24
- -1 aromatic carboxylic acids Chemical class 0.000 claims description 23
- 239000002253 acid Substances 0.000 claims description 22
- 239000002245 particle Substances 0.000 claims description 20
- 238000000034 method Methods 0.000 claims description 16
- 239000000203 mixture Substances 0.000 claims description 14
- 229920002480 polybenzimidazole Polymers 0.000 claims description 12
- 150000002148 esters Chemical class 0.000 claims description 10
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 claims description 10
- 239000004693 Polybenzimidazole Substances 0.000 claims description 8
- 150000008064 anhydrides Chemical class 0.000 claims description 8
- 150000001805 chlorine compounds Chemical class 0.000 claims description 8
- 238000010438 heat treatment Methods 0.000 claims description 8
- 150000000000 tetracarboxylic acids Chemical class 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
- 125000003837 (C1-C20) alkyl group Chemical group 0.000 claims description 7
- 239000011261 inert gas Substances 0.000 claims description 7
- 238000002156 mixing Methods 0.000 claims description 7
- 150000003628 tricarboxylic acids Chemical class 0.000 claims description 7
- 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 6
- KLSJWNVTNUYHDU-UHFFFAOYSA-N Amitrole Chemical group NC1=NC=NN1 KLSJWNVTNUYHDU-UHFFFAOYSA-N 0.000 claims description 6
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 claims description 6
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 6
- WJJMNDUMQPNECX-UHFFFAOYSA-N dipicolinic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=N1 WJJMNDUMQPNECX-UHFFFAOYSA-N 0.000 claims description 6
- 229910052757 nitrogen Inorganic materials 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
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 5
- 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
- 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
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 4
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 4
- 238000001816 cooling Methods 0.000 claims description 4
- 229910052760 oxygen Inorganic materials 0.000 claims description 4
- 239000001301 oxygen Substances 0.000 claims description 4
- 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 claims description 4
- 229910052717 sulfur Inorganic materials 0.000 claims description 4
- 239000011593 sulfur Substances 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
- 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 3
- 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 3
- 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 3
- 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 3
- 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 3
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims description 3
- 150000008065 acid anhydrides Chemical class 0.000 claims description 3
- 125000003277 amino group Chemical group 0.000 claims description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 3
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- 125000001142 dicarboxylic acid group Chemical group 0.000 claims description 3
- 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 3
- 238000000227 grinding Methods 0.000 claims description 3
- MJIVRKPEXXHNJT-UHFFFAOYSA-N lutidinic acid Chemical compound OC(=O)C1=CC=NC(C(O)=O)=C1 MJIVRKPEXXHNJT-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
- 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
- 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
- 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 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
- 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
- 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 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
- 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 description 2
- 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 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
- 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 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
- 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 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
- SCKXCAADGDQQCS-UHFFFAOYSA-N Performic acid Chemical compound OOC=O SCKXCAADGDQQCS-UHFFFAOYSA-N 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
- 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
- MPFLRYZEEAQMLQ-UHFFFAOYSA-N dinicotinic acid Chemical compound OC(=O)C1=CN=CC(C(O)=O)=C1 MPFLRYZEEAQMLQ-UHFFFAOYSA-N 0.000 claims description 2
- CZZYITDELCSZES-UHFFFAOYSA-N diphenylmethane Chemical compound C=1C=CC=CC=1CC1=CC=CC=C1 CZZYITDELCSZES-UHFFFAOYSA-N 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 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
- 239000000178 monomer Substances 0.000 claims description 2
- 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 description 2
- 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 2
- 125000004437 phosphorous atom Chemical group 0.000 claims description 2
- 229910052698 phosphorus Inorganic materials 0.000 claims description 2
- 229920002577 polybenzoxazole Polymers 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
- 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
- HAEJSGLKJYIYTB-UHFFFAOYSA-N 4-(2-carboxyethenyl)benzoic acid Chemical class OC(=O)C=CC1=CC=C(C(O)=O)C=C1 HAEJSGLKJYIYTB-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- DUTBTEWLGKSXNH-UHFFFAOYSA-N C(=O)(O)C1=CC2=CC(=CC=C2C=C1)C(=O)O.C(=O)(O)C1=CC=CC2=C(C=CC=C12)C(=O)O.C(=O)(O)C1=CC2=CC=C(C=C2C=C1)C(=O)O Chemical compound C(=O)(O)C1=CC2=CC(=CC=C2C=C1)C(=O)O.C(=O)(O)C1=CC=CC2=C(C=CC=C12)C(=O)O.C(=O)(O)C1=CC2=CC=C(C=C2C=C1)C(=O)O DUTBTEWLGKSXNH-UHFFFAOYSA-N 0.000 claims 1
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- MZYHMUONCNKCHE-UHFFFAOYSA-N naphthalene-1,2,3,4-tetracarboxylic acid Chemical compound C1=CC=CC2=C(C(O)=O)C(C(=O)O)=C(C(O)=O)C(C(O)=O)=C21 MZYHMUONCNKCHE-UHFFFAOYSA-N 0.000 claims 1
- 239000000835 fiber Substances 0.000 description 20
- 239000012528 membrane Substances 0.000 description 19
- 229920006254 polymer film Polymers 0.000 description 14
- 238000000926 separation method Methods 0.000 description 14
- 239000007789 gas Substances 0.000 description 7
- 239000000463 material Substances 0.000 description 7
- 229920005597 polymer membrane Polymers 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 6
- 239000002019 doping agent Substances 0.000 description 6
- 238000001035 drying Methods 0.000 description 6
- 239000007788 liquid Substances 0.000 description 6
- 238000001556 precipitation Methods 0.000 description 6
- 125000000217 alkyl group Chemical group 0.000 description 5
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 4
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 4
- 125000002723 alicyclic group Chemical group 0.000 description 4
- 125000001931 aliphatic group Chemical group 0.000 description 4
- FHESUNXRPBHDQM-UHFFFAOYSA-N diphenyl benzene-1,3-dicarboxylate Chemical compound C=1C=CC(C(=O)OC=2C=CC=CC=2)=CC=1C(=O)OC1=CC=CC=C1 FHESUNXRPBHDQM-UHFFFAOYSA-N 0.000 description 4
- 239000000945 filler Substances 0.000 description 4
- 238000001914 filtration Methods 0.000 description 4
- 239000006260 foam Substances 0.000 description 4
- 238000005194 fractionation Methods 0.000 description 4
- 239000012510 hollow fiber Substances 0.000 description 4
- 229910052751 metal Inorganic materials 0.000 description 4
- 239000002184 metal Substances 0.000 description 4
- 229920005594 polymer fiber Polymers 0.000 description 4
- XSCHRSMBECNVNS-UHFFFAOYSA-N quinoxaline Chemical compound N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 3
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 3
- 239000000010 aprotic solvent Substances 0.000 description 3
- 238000009826 distribution Methods 0.000 description 3
- 150000004760 silicates Chemical class 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
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Classifications
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- 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
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D61/00—Processes of separation using semi-permeable membranes, e.g. dialysis, osmosis or ultrafiltration; Apparatus, accessories or auxiliary operations specially adapted therefor
- B01D61/02—Reverse osmosis; Hyperfiltration ; Nanofiltration
- B01D61/025—Reverse osmosis; Hyperfiltration
-
- 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
-
- 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
- C08G73/0683—Polycondensates containing six-membered rings, condensed with other rings, with nitrogen atoms as the only ring hetero atoms
- C08G73/0688—Polycondensates containing six-membered rings, condensed with other rings, with nitrogen atoms as the only ring hetero atoms with only one nitrogen atom in the ring, e.g. polyquinolines
-
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- Y02E60/00—Enabling technologies; Technologies with a potential or indirect contribution to GHG emissions mitigation
- Y02E60/10—Energy storage using batteries
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- 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
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- Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
- Manufacture Of Macromolecular Shaped Articles (AREA)
- Fuel Cell (AREA)
- Polymers With Sulfur, Phosphorus Or Metals In The Main Chain (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
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| DE10258580A DE10258580A1 (de) | 2002-12-16 | 2002-12-16 | Hochmolekular Polyazole |
| PCT/EP2003/013529 WO2004055097A1 (de) | 2002-12-16 | 2003-12-02 | Hochmolekulare polyazole |
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| KR20060104163A (ko) * | 2005-03-29 | 2006-10-09 | 한국과학기술연구원 | 연료전지용 고분자 및 그 제조 방법 |
| US7504475B2 (en) * | 2005-07-11 | 2009-03-17 | Pbi Performance Products, Inc. | Process for a two stage melt polymerization for the production of polybenzimidazole |
| DE102005058579A1 (de) * | 2005-12-08 | 2007-06-14 | Sartorius Ag | Hochmolekulare Polyazole mit verbesserter Löslichkeit und Verfahren zu ihrer Herstellung |
| DE102005058578A1 (de) * | 2005-12-08 | 2007-06-28 | Sartorius Ag | Membranen aus Polyazolen, Verfahren zu ihrer Herstellung und Brennstoffzellen unter Verwendung derartiger Membranen |
| 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 |
| EP2192090A1 (en) * | 2008-12-01 | 2010-06-02 | Technische Universiteit Delft | Process for the production of ultra pure water using a membrane |
| US9011738B2 (en) * | 2009-01-14 | 2015-04-21 | Basf Se | Monomer beads for producing a proton-conducting membrane |
| KR101144398B1 (ko) * | 2009-01-15 | 2012-05-10 | 서울대학교산학협력단 | 염기성 치환기를 갖는 폴리벤즈이미다졸계 고분자 및 이를 포함하는 전해질막 |
| JP5305162B2 (ja) * | 2009-08-20 | 2013-10-02 | 東洋紡株式会社 | 多孔質材料を用いた燃料電池用触媒 |
| US8199595B2 (en) * | 2009-09-04 | 2012-06-12 | Micron Technology, Inc. | Techniques for sensing a semiconductor memory device |
| US8420732B2 (en) | 2009-12-21 | 2013-04-16 | Pbi Performance Products, Inc. | Polybenzimidazole solution in an ionic liquid |
| US20110189484A1 (en) | 2010-02-04 | 2011-08-04 | Hopkins Jr John B | Porous polybenzimidazole resin and method of making same |
| US9283523B2 (en) * | 2012-05-25 | 2016-03-15 | Pbi Performance Products, Inc. | Acid resistant PBI membrane for pervaporation dehydration of acidic solvents |
| US9598541B2 (en) | 2013-06-04 | 2017-03-21 | Pbi Performance Products, Inc. | Method of making polybenzimidazole |
| US10071345B2 (en) | 2015-06-23 | 2018-09-11 | Los Alamos National Security, Llc | Polybenzimidazole hollow fiber membranes and method for making an asymmetric hollow fiber membrane |
| US11959196B2 (en) | 2015-07-06 | 2024-04-16 | Pbi Performance Products, Inc. | Phosphonated PBI fiber |
| DE102017122416A1 (de) * | 2017-09-27 | 2019-03-28 | Airbus Operations Gmbh | Batterie mit integrierter Flammschutzvorrichtung |
| KR102877929B1 (ko) | 2018-09-14 | 2025-10-30 | 유니버시티 오브 싸우스 캐롤라이나 | 산화환원 유동 배터리용 폴리벤즈이미다졸 (pbi) 멤브레인 |
| KR102878113B1 (ko) | 2018-09-14 | 2025-10-30 | 유니버시티 오브 싸우스 캐롤라이나 | 산화환원 유동 배터리용 저투과도 폴리벤즈이미다졸 (pbi) 멤브레인 |
| EP3850035A1 (en) | 2018-09-14 | 2021-07-21 | University of South Carolina | New method for producing pbi films without organic solvents |
| US11777124B2 (en) | 2020-03-06 | 2023-10-03 | University Of South Carolina | Proton-conducting PBI membrane processing with enhanced performance and durability |
| WO2022123497A1 (en) * | 2020-12-09 | 2022-06-16 | King Abdullah University Of Science And Technology | Thermally crosslinked polytriazole separation membranes |
| CN116059801B (zh) * | 2023-01-10 | 2024-05-28 | 中南大学 | 一种气体膜分离装置、及气体选择性分离的方法 |
| US12636618B1 (en) | 2023-02-17 | 2026-05-26 | Triad National Security, Llc | Asymmetric carbon molecular sieve hollow fiber membranes |
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| US448687A (en) * | 1891-03-24 | stanley | ||
| US375262A (en) | 1887-12-20 | Coal-drilling machine | ||
| US3699038A (en) * | 1970-04-22 | 1972-10-17 | Celanese Corp | Production of improved semipermeable polybenzimidazole membranes |
| US3783137A (en) * | 1971-06-09 | 1974-01-01 | Horizons Inc | Process for the preparation of heterocyclic polymers fromaromatic tetra-mines and derivatives of polycarboxylic acids |
| US3841492A (en) | 1972-01-19 | 1974-10-15 | Celanese Corp | Production of semipermeable polybenzimidazole membranes |
| GB1422177A (en) * | 1973-05-08 | 1976-01-21 | Furukawa Electric Co Ltd | Method for producing a shaped article of a poly-1,3,4-oxadiazole resin having improved properties |
| JPS5633961B2 (enExample) * | 1974-12-19 | 1981-08-07 | ||
| US4154919A (en) * | 1976-08-31 | 1979-05-15 | Acurex Corporation | Linear and cross-linked 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 |
| WO1984001162A1 (en) | 1982-09-17 | 1984-03-29 | Stanford Res Inst Int | Liquid crystalline polymer compositions, process, and products |
| WO1984001160A1 (en) * | 1982-09-17 | 1984-03-29 | Stanford Res Inst Int | Liquid crystalline polymer compositions, process, and products |
| US4512894A (en) | 1982-12-17 | 1985-04-23 | Celanese Corporation | Process for the production of semipermeable polybenzimidazole membranes and the resultant product |
| US4448687A (en) | 1982-12-17 | 1984-05-15 | Celanese Corporation | Process for the production of semipermeable polybenzimidazole membranes with low temperature annealing |
| US4533725A (en) * | 1983-01-28 | 1985-08-06 | Delanese Corporation | Synthesis of high molecular weight polybenzimidazole with arylhalo phosphorus compound catalyst |
| US4535144A (en) * | 1983-01-28 | 1985-08-13 | Celanese Corporation | Synthesis of high molecular weight polybenzimidazole with arylhalo phosphorus compound catalyst |
| US4463167A (en) | 1983-03-21 | 1984-07-31 | Celanese Corporation | Two stage high molecular weight polybenzimidazole production with phosphorus containing catalyst |
| US4588808A (en) * | 1984-08-31 | 1986-05-13 | Celanese Corporation | Two-stage process and product for producing polybenzimidazoles from free dicarboxylic acids |
| US4672104A (en) | 1984-08-31 | 1987-06-09 | Celanese Corporation | Two stage polybenzimidazole process and product |
| US4693824A (en) * | 1985-09-23 | 1987-09-15 | Celanese Corporation | Process for the production of polybenzimidazole ultrafiltration membranes |
| 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 |
| US4693815A (en) * | 1986-08-01 | 1987-09-15 | Collins Jr Henry R | Self-cleaning filter system |
| US5017420A (en) * | 1986-10-23 | 1991-05-21 | Hoechst Celanese Corp. | Process for preparing electrically conductive shaped articles from polybenzimidazoles |
| US5091500A (en) * | 1990-09-21 | 1992-02-25 | The Dow Chemical Company | Polybenzazole polymer containing perfluorocyclobutane rings |
| US5599639A (en) * | 1995-08-31 | 1997-02-04 | Hoechst Celanese Corporation | Acid-modified polybenzimidazole fuel cell elements |
| JP3521579B2 (ja) * | 1995-10-18 | 2004-04-19 | Ｊｓｒ株式会社 | リン酸基含有重合体 |
| ATE215107T1 (de) | 1996-10-01 | 2002-04-15 | Celanese Ventures Gmbh | Verfahren zur herstellung von polymerfolien für verwendung in brennstoffzellen |
| 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 |
| EP1354907B1 (en) * | 2000-11-13 | 2006-03-01 | Toyo Boseki Kabushiki Kaisha | Polybenzazole compound having sulfo group and/or phosphono group, resin composition containing the same, molded resin, solid polymer electrolyte film, solid electrolyte film/electrode catalyst layer composite, and process for producing the composite |
| JP3690589B2 (ja) * | 2000-11-13 | 2005-08-31 | 東洋紡績株式会社 | スルホン酸含有ポリイミダゾール化合物およびその成型物 |
| 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 |
| DE10109829A1 (de) | 2001-03-01 | 2002-09-05 | Celanese Ventures Gmbh | Polymermembran, Verfahren zu deren Herstellung sowie deren Verwendung |
| US6681648B1 (en) * | 2001-04-04 | 2004-01-27 | The Regents Of The University Of California | Meniscus membranes for separations |
| JP2003105259A (ja) * | 2001-09-28 | 2003-04-09 | Clariant (Japan) Kk | ポリベンゾイミダゾール被膜およびフィルムの形成方法 |
| US7883818B2 (en) * | 2002-08-29 | 2011-02-08 | Basf Fuel Cell Gmbh | Process for producing proton-conducting polymer membranes, improved polymer membranes and the use thereof in fuel cells |
| ITPG20030005A1 (it) * | 2003-02-19 | 2004-08-20 | Giulio Alberti | Preparazione di nuovi fosfati acidi di metalli tetravalenti |
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| WO2004055097A1 (de) | 2004-07-01 |
| JP2007146165A (ja) | 2007-06-14 |
| US20080119634A1 (en) | 2008-05-22 |
| CN101914203B (zh) | 2012-04-25 |
| KR101205612B1 (ko) | 2012-11-27 |
| JP4663618B2 (ja) | 2011-04-06 |
| DE10258580A1 (de) | 2004-06-24 |
| KR101160032B1 (ko) | 2012-06-26 |
| CA2509228A1 (en) | 2004-07-01 |
| CN1978500B (zh) | 2013-10-02 |
| US7837763B2 (en) | 2010-11-23 |
| US20070151926A1 (en) | 2007-07-05 |
| EP2267060B1 (de) | 2014-09-17 |
| CN1732208A (zh) | 2006-02-08 |
| EP1583789A1 (de) | 2005-10-12 |
| KR20050092704A (ko) | 2005-09-22 |
| CN1978500A (zh) | 2007-06-13 |
| BR0317338B1 (pt) | 2013-07-23 |
| BR0317338A (pt) | 2005-11-08 |
| US7696302B2 (en) | 2010-04-13 |
| EP2267060A1 (de) | 2010-12-29 |
| EP1583789B1 (de) | 2014-07-02 |
| KR20070011625A (ko) | 2007-01-24 |
| CN101914203A (zh) | 2010-12-15 |
| MXPA05006414A (es) | 2006-03-08 |
| CA2509228C (en) | 2012-03-06 |
| JP2006509867A (ja) | 2006-03-23 |
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