NO972084L - Fremgangsmåte for emulsjons-polymerisasjon og fremstilte elektrisk ledende polyanilinsalter - Google Patents
Fremgangsmåte for emulsjons-polymerisasjon og fremstilte elektrisk ledende polyanilinsalterInfo
- Publication number
- NO972084L NO972084L NO972084A NO972084A NO972084L NO 972084 L NO972084 L NO 972084L NO 972084 A NO972084 A NO 972084A NO 972084 A NO972084 A NO 972084A NO 972084 L NO972084 L NO 972084L
- Authority
- NO
- Norway
- Prior art keywords
- acid
- organic
- water
- polyaniline
- polyaniline salt
- Prior art date
Links
- 229920000767 polyaniline Polymers 0.000 title claims abstract description 200
- 150000003839 salts Chemical class 0.000 title claims abstract description 142
- 238000000034 method Methods 0.000 title claims abstract description 55
- 230000008569 process Effects 0.000 title claims abstract description 23
- 238000007720 emulsion polymerization reaction Methods 0.000 title abstract description 37
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims abstract description 125
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 79
- 239000000203 mixture Substances 0.000 claims abstract description 58
- 239000003960 organic solvent Substances 0.000 claims abstract description 51
- 239000002253 acid Substances 0.000 claims abstract description 48
- 150000007524 organic acids Chemical class 0.000 claims abstract description 38
- 239000008096 xylene Substances 0.000 claims abstract description 38
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims abstract description 31
- 239000003999 initiator Substances 0.000 claims abstract description 13
- 239000000178 monomer Substances 0.000 claims abstract description 6
- 239000002904 solvent Substances 0.000 claims description 80
- CJMZLCRLBNZJQR-UHFFFAOYSA-N ethyl 2-amino-4-(4-fluorophenyl)thiophene-3-carboxylate Chemical compound CCOC(=O)C1=C(N)SC=C1C1=CC=C(F)C=C1 CJMZLCRLBNZJQR-UHFFFAOYSA-N 0.000 claims description 60
- ROOXNKNUYICQNP-UHFFFAOYSA-N ammonium persulfate Chemical group [NH4+].[NH4+].[O-]S(=O)(=O)OOS([O-])(=O)=O ROOXNKNUYICQNP-UHFFFAOYSA-N 0.000 claims description 39
- 239000000839 emulsion Substances 0.000 claims description 31
- 239000012074 organic phase Substances 0.000 claims description 23
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 21
- 229910001870 ammonium persulfate Inorganic materials 0.000 claims description 19
- 239000002245 particle Substances 0.000 claims description 17
- 238000002360 preparation method Methods 0.000 claims description 15
- 239000008346 aqueous phase Substances 0.000 claims description 14
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims description 12
- 239000001257 hydrogen Substances 0.000 claims description 9
- 229910052739 hydrogen Inorganic materials 0.000 claims description 9
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 claims description 6
- KTCQQCLZUOZFEI-UHFFFAOYSA-N 1,1,2,2-tetrafluoro-2-[1,1,1,2,3,3-hexafluoro-3-(1,2,2-trifluoroethenoxy)propan-2-yl]oxyethanesulfonyl fluoride Chemical compound FC(F)=C(F)OC(F)(F)C(F)(C(F)(F)F)OC(F)(F)C(F)(F)S(F)(=O)=O KTCQQCLZUOZFEI-UHFFFAOYSA-N 0.000 claims description 5
- RWNUSVWFHDHRCJ-UHFFFAOYSA-N 1-butoxypropan-2-ol Chemical compound CCCCOCC(C)O RWNUSVWFHDHRCJ-UHFFFAOYSA-N 0.000 claims description 5
- 229920001577 copolymer Polymers 0.000 claims description 5
- BFKJFAAPBSQJPD-UHFFFAOYSA-N tetrafluoroethene Chemical group FC(F)=C(F)F BFKJFAAPBSQJPD-UHFFFAOYSA-N 0.000 claims description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims description 3
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- 125000002877 alkyl aryl group Chemical group 0.000 claims description 3
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 3
- 229910052736 halogen Inorganic materials 0.000 claims description 3
- 150000002367 halogens Chemical class 0.000 claims description 3
- 150000002431 hydrogen Chemical class 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
- 229910052698 phosphorus Inorganic materials 0.000 claims description 3
- 239000011574 phosphorus Substances 0.000 claims description 3
- BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical compound OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 claims 6
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims 2
- POAOYUHQDCAZBD-IDEBNGHGSA-N 2-butoxyethanol Chemical group [13CH3][13CH2][13CH2][13CH2]O[13CH2][13CH2]O POAOYUHQDCAZBD-IDEBNGHGSA-N 0.000 claims 1
- 239000013256 coordination polymer Substances 0.000 claims 1
- 230000002209 hydrophobic effect Effects 0.000 abstract description 4
- POAOYUHQDCAZBD-UHFFFAOYSA-N 2-butoxyethanol Chemical compound CCCCOCCO POAOYUHQDCAZBD-UHFFFAOYSA-N 0.000 description 38
- 239000000243 solution Substances 0.000 description 34
- 238000006116 polymerization reaction Methods 0.000 description 33
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical class CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 33
- 239000000463 material Substances 0.000 description 27
- 239000012071 phase Substances 0.000 description 22
- 229920000642 polymer Polymers 0.000 description 20
- WBIQQQGBSDOWNP-UHFFFAOYSA-N 2-dodecylbenzenesulfonic acid Chemical class CCCCCCCCCCCCC1=CC=CC=C1S(O)(=O)=O WBIQQQGBSDOWNP-UHFFFAOYSA-N 0.000 description 19
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 18
- 238000006243 chemical reaction Methods 0.000 description 17
- 238000000576 coating method Methods 0.000 description 17
- 229940060296 dodecylbenzenesulfonic acid Drugs 0.000 description 16
- 239000002244 precipitate Substances 0.000 description 16
- 239000011248 coating agent Substances 0.000 description 14
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 13
- 239000011541 reaction mixture Substances 0.000 description 13
- 229910052757 nitrogen Inorganic materials 0.000 description 12
- 238000012360 testing method Methods 0.000 description 11
- QBDAFARLDLCWAT-UHFFFAOYSA-N 2,3-dihydropyran-6-one Chemical compound O=C1OCCC=C1 QBDAFARLDLCWAT-UHFFFAOYSA-N 0.000 description 10
- 150000003254 radicals Chemical class 0.000 description 10
- 239000000758 substrate Substances 0.000 description 9
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
- 230000015572 biosynthetic process Effects 0.000 description 8
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 8
- 239000011833 salt mixture Substances 0.000 description 7
- 150000003738 xylenes Chemical class 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- WDNQRCVBPNOTNV-UHFFFAOYSA-N dinonylnaphthylsulfonic acid Chemical class C1=CC=C2C(S(O)(=O)=O)=C(CCCCCCCCC)C(CCCCCCCCC)=CC2=C1 WDNQRCVBPNOTNV-UHFFFAOYSA-N 0.000 description 6
- 238000001035 drying Methods 0.000 description 6
- 235000005985 organic acids Nutrition 0.000 description 6
- 150000007513 acids Chemical class 0.000 description 5
- 239000002390 adhesive tape Substances 0.000 description 5
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- 239000008187 granular material Substances 0.000 description 5
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- 238000005406 washing Methods 0.000 description 5
- KBPLFHHGFOOTCA-UHFFFAOYSA-N 1-Octanol Chemical compound CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- 238000005481 NMR spectroscopy Methods 0.000 description 4
- 239000006185 dispersion Substances 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 229910052751 metal Inorganic materials 0.000 description 4
- 239000002184 metal Substances 0.000 description 4
- 230000003472 neutralizing effect Effects 0.000 description 4
- 229910052717 sulfur Inorganic materials 0.000 description 4
- 238000003786 synthesis reaction Methods 0.000 description 4
- PBKONEOXTCPAFI-UHFFFAOYSA-N 1,2,4-trichlorobenzene Chemical compound ClC1=CC=C(Cl)C(Cl)=C1 PBKONEOXTCPAFI-UHFFFAOYSA-N 0.000 description 3
- AHVYPIQETPWLSZ-UHFFFAOYSA-N 1-methyl-2,5-dihydropyrrole Chemical compound CN1CC=CC1 AHVYPIQETPWLSZ-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- VZTDIZULWFCMLS-UHFFFAOYSA-N ammonium formate Chemical compound [NH4+].[O-]C=O VZTDIZULWFCMLS-UHFFFAOYSA-N 0.000 description 3
- 239000000908 ammonium hydroxide Substances 0.000 description 3
- 230000008901 benefit Effects 0.000 description 3
- 238000004090 dissolution Methods 0.000 description 3
- 238000004817 gas chromatography Methods 0.000 description 3
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- 229920005992 thermoplastic resin Polymers 0.000 description 3
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 2
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 2
- 229920000557 Nafion® Polymers 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- 239000004793 Polystyrene Substances 0.000 description 2
- 229910000831 Steel Inorganic materials 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 2
- 235000019395 ammonium persulphate Nutrition 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 239000011651 chromium Substances 0.000 description 2
- 229910052804 chromium Inorganic materials 0.000 description 2
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- 230000007797 corrosion Effects 0.000 description 2
- 238000005260 corrosion Methods 0.000 description 2
- NNBZCPXTIHJBJL-UHFFFAOYSA-N decalin Chemical compound C1CCCC2CCCCC21 NNBZCPXTIHJBJL-UHFFFAOYSA-N 0.000 description 2
- MWKFXSUHUHTGQN-UHFFFAOYSA-N decan-1-ol Chemical compound CCCCCCCCCCO MWKFXSUHUHTGQN-UHFFFAOYSA-N 0.000 description 2
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- 238000000921 elemental analysis Methods 0.000 description 2
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- UQSQSQZYBQSBJZ-UHFFFAOYSA-N fluorosulfonic acid Chemical compound OS(F)(=O)=O UQSQSQZYBQSBJZ-UHFFFAOYSA-N 0.000 description 2
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- 239000011521 glass Substances 0.000 description 2
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- RLSSMJSEOOYNOY-UHFFFAOYSA-N m-cresol Chemical compound CC1=CC=CC(O)=C1 RLSSMJSEOOYNOY-UHFFFAOYSA-N 0.000 description 2
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- 150000002739 metals Chemical class 0.000 description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
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- 239000011356 non-aqueous organic solvent Substances 0.000 description 2
- ZWRUINPWMLAQRD-UHFFFAOYSA-N nonan-1-ol Chemical compound CCCCCCCCCO ZWRUINPWMLAQRD-UHFFFAOYSA-N 0.000 description 2
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- KMUONIBRACKNSN-UHFFFAOYSA-N potassium dichromate Chemical compound [K+].[K+].[O-][Cr](=O)(=O)O[Cr]([O-])(=O)=O KMUONIBRACKNSN-UHFFFAOYSA-N 0.000 description 2
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- DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 description 1
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- LBLYYCQCTBFVLH-UHFFFAOYSA-N 2-Methylbenzenesulfonic acid Chemical compound CC1=CC=CC=C1S(O)(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-N 0.000 description 1
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- 229910052758 niobium Inorganic materials 0.000 description 1
- 239000010955 niobium Substances 0.000 description 1
- GUCVJGMIXFAOAE-UHFFFAOYSA-N niobium atom Chemical compound [Nb] GUCVJGMIXFAOAE-UHFFFAOYSA-N 0.000 description 1
- 239000012454 non-polar solvent Substances 0.000 description 1
- 238000000879 optical micrograph Methods 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 238000010422 painting Methods 0.000 description 1
- 230000035699 permeability Effects 0.000 description 1
- 238000005191 phase separation Methods 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- -1 polyethylene Polymers 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 230000000379 polymerizing effect Effects 0.000 description 1
- 239000004810 polytetrafluoroethylene Substances 0.000 description 1
- 229920001343 polytetrafluoroethylene Polymers 0.000 description 1
- 239000011148 porous material Substances 0.000 description 1
- 235000019396 potassium bromate Nutrition 0.000 description 1
- 229940094037 potassium bromate Drugs 0.000 description 1
- VKJKEPKFPUWCAS-UHFFFAOYSA-M potassium chlorate Chemical compound [K+].[O-]Cl(=O)=O VKJKEPKFPUWCAS-UHFFFAOYSA-M 0.000 description 1
- JLKDVMWYMMLWTI-UHFFFAOYSA-M potassium iodate Chemical compound [K+].[O-]I(=O)=O JLKDVMWYMMLWTI-UHFFFAOYSA-M 0.000 description 1
- 239000001230 potassium iodate Substances 0.000 description 1
- 229940093930 potassium iodate Drugs 0.000 description 1
- 235000006666 potassium iodate Nutrition 0.000 description 1
- 239000012286 potassium permanganate Substances 0.000 description 1
- 239000012254 powdered material Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 238000007639 printing Methods 0.000 description 1
- 239000012266 salt solution Substances 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 238000002791 soaking Methods 0.000 description 1
- 239000012798 spherical particle Substances 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 239000010414 supernatant solution Substances 0.000 description 1
- 238000004381 surface treatment Methods 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 229910052715 tantalum Inorganic materials 0.000 description 1
- GUVRBAGPIYLISA-UHFFFAOYSA-N tantalum atom Chemical compound [Ta] GUVRBAGPIYLISA-UHFFFAOYSA-N 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 238000002076 thermal analysis method Methods 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 238000000108 ultra-filtration Methods 0.000 description 1
- 238000007738 vacuum evaporation Methods 0.000 description 1
- 239000012905 visible particle Substances 0.000 description 1
- 238000011179 visual inspection Methods 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229910052726 zirconium Inorganic materials 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
- C08G73/02—Polyamines
- C08G73/026—Wholly aromatic polyamines
- C08G73/0266—Polyanilines or derivatives thereof
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01B—CABLES; CONDUCTORS; INSULATORS; SELECTION OF MATERIALS FOR THEIR CONDUCTIVE, INSULATING OR DIELECTRIC PROPERTIES
- H01B1/00—Conductors or conductive bodies characterised by the conductive materials; Selection of materials as conductors
- H01B1/06—Conductors or conductive bodies characterised by the conductive materials; Selection of materials as conductors mainly consisting of other non-metallic substances
- H01B1/12—Conductors or conductive bodies characterised by the conductive materials; Selection of materials as conductors mainly consisting of other non-metallic substances organic substances
- H01B1/124—Intrinsically conductive polymers
- H01B1/128—Intrinsically conductive polymers comprising six-membered aromatic rings in the main chain, e.g. polyanilines, polyphenylenes
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Physics & Mathematics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Polymers With Sulfur, Phosphorus Or Metals In The Main Chain (AREA)
- Polymerisation Methods In General (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US08/335,143 US5567356A (en) | 1994-11-07 | 1994-11-07 | Emulsion-polymerization process and electrically-conductive polyaniline salts |
| PCT/US1995/014610 WO1996014343A1 (en) | 1994-11-07 | 1995-11-07 | Emulsion-polymerization process and electrically-conductive polyaniline salts |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| NO972084D0 NO972084D0 (no) | 1997-05-06 |
| NO972084L true NO972084L (no) | 1997-07-04 |
Family
ID=23310457
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO972084A NO972084L (no) | 1994-11-07 | 1997-05-06 | Fremgangsmåte for emulsjons-polymerisasjon og fremstilte elektrisk ledende polyanilinsalter |
Country Status (14)
| Country | Link |
|---|---|
| US (2) | US5567356A (ja) |
| EP (1) | EP0796283B1 (ja) |
| JP (1) | JP3634866B2 (ja) |
| KR (1) | KR100409109B1 (ja) |
| AT (1) | ATE193708T1 (ja) |
| AU (1) | AU4152996A (ja) |
| CA (1) | CA2204653C (ja) |
| DE (1) | DE69517444T2 (ja) |
| DK (1) | DK0796283T3 (ja) |
| ES (1) | ES2146787T3 (ja) |
| FI (1) | FI115059B (ja) |
| GR (1) | GR3034223T3 (ja) |
| NO (1) | NO972084L (ja) |
| WO (1) | WO1996014343A1 (ja) |
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| US5324453A (en) | 1992-08-07 | 1994-06-28 | Neste Oy | Electrically conducting polyaniline: method for emulsion polymerization |
| US5567356A (en) * | 1994-11-07 | 1996-10-22 | Monsanto Company | Emulsion-polymerization process and electrically-conductive polyaniline salts |
| US5804100A (en) * | 1995-01-09 | 1998-09-08 | International Business Machines Corporation | Deaggregated electrically conductive polymers and precursors thereof |
| US5932143A (en) * | 1995-11-29 | 1999-08-03 | International Business Machines Corporation | Polycrystalline conducting polymers and precursors thereof having adjustable morphology and physical properties |
| US5928566A (en) | 1995-11-29 | 1999-07-27 | International Business Machines Corporation | Plasticized, antiplasticized and crystalline conducting polymers |
| US7423167B2 (en) * | 1997-01-28 | 2008-09-09 | Stepan Company | Ethylenically unsaturated amine salts of sulfonic, phosphoric and carboxylic acids |
| BR9807030B1 (pt) | 1997-01-28 | 2009-01-13 | agente tensoativo polimerizÁvel, e, soluÇço aquosa de tensoativo. | |
| WO1998055532A1 (en) * | 1997-06-03 | 1998-12-10 | Zipperling Kessler & Co. | Electrochemical synthesis of electrically conductive polymers and products thereof |
| US5911930A (en) * | 1997-08-25 | 1999-06-15 | Monsanto Company | Solvent spinning of fibers containing an intrinsically conductive polymer |
| US6228492B1 (en) | 1997-09-23 | 2001-05-08 | Zipperling Kessler & Co. (Gmbh & Co.) | Preparation of fibers containing intrinsically conductive polymers |
| US5871671A (en) * | 1997-10-14 | 1999-02-16 | Monsanto Company | Intrinsically conductive polymer/plasticizer blends with enhanced conductivity |
| US5853794A (en) * | 1997-10-31 | 1998-12-29 | Kemet Electronics Corp. | Doped polyaniline solutions |
| US6072027A (en) * | 1997-11-18 | 2000-06-06 | The Dow Chemical Company | Process for preparing an electrically conductive polymer |
| US5888582A (en) * | 1997-12-09 | 1999-03-30 | Kemet Electronics Corp. | Polyaniline solutions with bicyclic terpene solvent |
| WO2000002979A1 (en) * | 1998-07-09 | 2000-01-20 | Zipperling Kessler & Co. (Gmbh & Co.) | Lubricating compositions containing soluble conducting polymers as anti-corrosion additives |
| US6030551A (en) * | 1999-04-07 | 2000-02-29 | Conpoly Technology Co., Ltd. | Polyaniline-containing solution and method for preparing the same |
| US6136176A (en) * | 1999-05-21 | 2000-10-24 | Kemet Electronics Corporation | Capacitor with conductive polymer |
| CN1094134C (zh) * | 1999-10-26 | 2002-11-13 | 北京燕山石油化工公司研究院 | 导电聚苯胺水胶乳及其制备方法和应用 |
| KR20010056209A (ko) * | 1999-12-17 | 2001-07-04 | 이형도 | 전도성 폴리아닐린의 합성방법 |
| KR20010109812A (ko) * | 2000-06-02 | 2001-12-12 | 오권오 | 다양한 유기 극성용매에 용해성을 갖는 폴리아닐린 염의제조방법 |
| US6803446B2 (en) | 2000-07-13 | 2004-10-12 | The Board Of Governors For Higher Education, State Of Rhode Island And Providence Plantations | Functionalized and processable conducting polymers |
| US6334945B1 (en) | 2000-09-07 | 2002-01-01 | Kemet Electronics Corporation | Aging process for solid electrode capacitor |
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| AU2002242943B1 (en) * | 2002-03-21 | 2003-10-08 | Council Of Scientific And Industrial Research | Process for the preparation of polyaniline salt |
| KR100445287B1 (ko) * | 2002-04-16 | 2004-08-21 | 주식회사 옴니켐 | 폴리아닐린의 새로운 제조 방법 |
| KR100514643B1 (ko) * | 2002-05-23 | 2005-09-13 | 주식회사 유진텍 이십일 | 폴리아닐린의 제조방법 |
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| BRPI0409260A (pt) * | 2003-04-11 | 2006-03-28 | Nippon Catalytic Chem Ind | composição contendo polianilina |
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| SE525033C2 (sv) * | 2003-04-30 | 2004-11-16 | Mikael Nutsos | Ledande luftreningsfilter och aggregat innefattande sådant filter |
| US8323385B2 (en) * | 2003-04-30 | 2012-12-04 | Mikael Nutsos | Conducting air filter and filter assembly |
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| US8153029B2 (en) * | 2006-12-28 | 2012-04-10 | E.I. Du Pont De Nemours And Company | Laser (230NM) ablatable compositions of electrically conducting polymers made with a perfluoropolymeric acid applications thereof |
| US20080191172A1 (en) | 2006-12-29 | 2008-08-14 | Che-Hsiung Hsu | High work-function and high conductivity compositions of electrically conducting polymers |
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| US8241526B2 (en) | 2007-05-18 | 2012-08-14 | E I Du Pont De Nemours And Company | Aqueous dispersions of electrically conducting polymers containing high boiling solvent and additives |
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| EP2406796A2 (en) | 2009-03-12 | 2012-01-18 | E. I. du Pont de Nemours and Company | Electrically conductive polymer compositions for coating applications |
| CN102395628B (zh) | 2009-04-21 | 2016-01-20 | E.I.内穆尔杜邦公司 | 导电聚合物组合物和由其制得的膜 |
| JP2012524834A (ja) | 2009-04-24 | 2012-10-18 | イー・アイ・デュポン・ドウ・ヌムール・アンド・カンパニー | 導電性ポリマー組成物およびそれから作製されたフィルム |
| JP2014509667A (ja) | 2011-03-29 | 2014-04-21 | エフピーイノベイションズ | ナノ結晶セルロース及びポリアニリンに基づく可撓性の半導体ナノコンポジット材料 |
| US9492288B2 (en) | 2013-02-20 | 2016-11-15 | Flexuspine, Inc. | Expandable fusion device for positioning between adjacent vertebral bodies |
| US10398565B2 (en) | 2014-04-24 | 2019-09-03 | Choice Spine, Llc | Limited profile intervertebral implant with incorporated fastening and locking mechanism |
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| BR112019024703A2 (pt) * | 2017-05-25 | 2020-06-09 | Nissan Chemical Corp | método de produção de um filme fino de transporte de carga |
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| CN112490450B (zh) * | 2020-10-26 | 2022-05-10 | 温州大学 | 一种用于微生物燃料电池的粘合剂、应用、阴极及微生物燃料电池 |
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|---|---|---|---|---|
| US4731408A (en) * | 1985-12-20 | 1988-03-15 | Polaroid Corporation | Processable conductive polymers |
| US5069820A (en) * | 1987-08-07 | 1991-12-03 | Allied-Signal Inc. | Thermally stable forms of electrically conductive polyaniline |
| US5160457A (en) * | 1987-08-07 | 1992-11-03 | Allied-Signal Inc. | Thermally stable forms of electrically conductive polyaniline |
| US5378403A (en) * | 1987-08-07 | 1995-01-03 | Alliedsignal Inc. | High electrically conductive polyanaline complexes having polar substitutents |
| US5281363A (en) * | 1991-04-22 | 1994-01-25 | Allied-Signal Inc. | Polyaniline compositions having a surface/core dopant arrangement |
| US5232631A (en) * | 1991-06-12 | 1993-08-03 | Uniax Corporation | Processible forms of electrically conductive polyaniline |
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| JP3204550B2 (ja) * | 1991-12-11 | 2001-09-04 | 日東電工株式会社 | 導電性有機重合体の製造方法 |
| US5324453A (en) * | 1992-08-07 | 1994-06-28 | Neste Oy | Electrically conducting polyaniline: method for emulsion polymerization |
| US5567356A (en) * | 1994-11-07 | 1996-10-22 | Monsanto Company | Emulsion-polymerization process and electrically-conductive polyaniline salts |
-
1994
- 1994-11-07 US US08/335,143 patent/US5567356A/en not_active Expired - Lifetime
-
1995
- 1995-11-07 ES ES95939869T patent/ES2146787T3/es not_active Expired - Lifetime
- 1995-11-07 WO PCT/US1995/014610 patent/WO1996014343A1/en not_active Ceased
- 1995-11-07 JP JP51552496A patent/JP3634866B2/ja not_active Expired - Fee Related
- 1995-11-07 CA CA002204653A patent/CA2204653C/en not_active Expired - Fee Related
- 1995-11-07 AU AU41529/96A patent/AU4152996A/en not_active Abandoned
- 1995-11-07 US US08/596,202 patent/US5863465A/en not_active Expired - Lifetime
- 1995-11-07 AT AT95939869T patent/ATE193708T1/de not_active IP Right Cessation
- 1995-11-07 DK DK95939869T patent/DK0796283T3/da active
- 1995-11-07 EP EP95939869A patent/EP0796283B1/en not_active Expired - Lifetime
- 1995-11-07 DE DE69517444T patent/DE69517444T2/de not_active Expired - Lifetime
- 1995-11-07 KR KR1019970703052A patent/KR100409109B1/ko not_active Expired - Fee Related
-
1997
- 1997-05-06 NO NO972084A patent/NO972084L/no not_active Application Discontinuation
- 1997-05-07 FI FI971954A patent/FI115059B/fi not_active IP Right Cessation
-
2000
- 2000-08-17 GR GR20000401908T patent/GR3034223T3/el not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| ATE193708T1 (de) | 2000-06-15 |
| JP3634866B2 (ja) | 2005-03-30 |
| CA2204653A1 (en) | 1996-05-17 |
| US5863465A (en) | 1999-01-26 |
| KR100409109B1 (ko) | 2004-05-06 |
| NO972084D0 (no) | 1997-05-06 |
| FI971954L (fi) | 1997-06-25 |
| DK0796283T3 (da) | 2000-08-07 |
| JPH10509751A (ja) | 1998-09-22 |
| AU4152996A (en) | 1996-05-31 |
| EP0796283A4 (en) | 1998-03-11 |
| ES2146787T3 (es) | 2000-08-16 |
| CA2204653C (en) | 2004-09-21 |
| DE69517444D1 (de) | 2000-07-13 |
| DE69517444T2 (de) | 2001-01-18 |
| WO1996014343A1 (en) | 1996-05-17 |
| US5567356A (en) | 1996-10-22 |
| EP0796283B1 (en) | 2000-06-07 |
| FI115059B (fi) | 2005-02-28 |
| EP0796283A1 (en) | 1997-09-24 |
| GR3034223T3 (en) | 2000-12-29 |
| FI971954A0 (fi) | 1997-05-07 |
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