JP4262203B2 - ポリアニリン塩の調製方法 - Google Patents
ポリアニリン塩の調製方法 Download PDFInfo
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- JP4262203B2 JP4262203B2 JP2004549395A JP2004549395A JP4262203B2 JP 4262203 B2 JP4262203 B2 JP 4262203B2 JP 2004549395 A JP2004549395 A JP 2004549395A JP 2004549395 A JP2004549395 A JP 2004549395A JP 4262203 B2 JP4262203 B2 JP 4262203B2
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- polyaniline
- polyaniline salt
- salt
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- emulsion
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- 229920000767 polyaniline Polymers 0.000 title claims description 161
- 150000003839 salts Chemical class 0.000 title claims description 126
- 238000000034 method Methods 0.000 title claims description 37
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 48
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 39
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 38
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims description 34
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 32
- 239000000839 emulsion Substances 0.000 claims description 31
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 30
- 239000003960 organic solvent Substances 0.000 claims description 23
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 21
- 239000012071 phase Substances 0.000 claims description 20
- 239000012046 mixed solvent Substances 0.000 claims description 19
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 13
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 claims description 13
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 claims description 13
- 239000011976 maleic acid Substances 0.000 claims description 13
- 235000019333 sodium laurylsulphate Nutrition 0.000 claims description 13
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims description 13
- 239000004342 Benzoyl peroxide Substances 0.000 claims description 12
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 claims description 12
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 12
- DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 claims description 12
- 235000019400 benzoyl peroxide Nutrition 0.000 claims description 12
- 239000000843 powder Substances 0.000 claims description 11
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 10
- 239000008346 aqueous phase Substances 0.000 claims description 10
- 239000012153 distilled water Substances 0.000 claims description 10
- 238000006116 polymerization reaction Methods 0.000 claims description 10
- 239000008096 xylene Substances 0.000 claims description 10
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 claims description 9
- 238000007720 emulsion polymerization reaction Methods 0.000 claims description 9
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 8
- 239000007787 solid Substances 0.000 claims description 8
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims description 6
- 239000003945 anionic surfactant Substances 0.000 claims description 6
- MWKFXSUHUHTGQN-UHFFFAOYSA-N decan-1-ol Chemical compound CCCCCCCCCCO MWKFXSUHUHTGQN-UHFFFAOYSA-N 0.000 claims description 6
- LQZZUXJYWNFBMV-UHFFFAOYSA-N dodecan-1-ol Chemical compound CCCCCCCCCCCCO LQZZUXJYWNFBMV-UHFFFAOYSA-N 0.000 claims description 6
- UAEPNZWRGJTJPN-UHFFFAOYSA-N methylcyclohexane Chemical compound CC1CCCCC1 UAEPNZWRGJTJPN-UHFFFAOYSA-N 0.000 claims description 6
- 239000000203 mixture Substances 0.000 claims description 6
- 150000004982 aromatic amines Chemical class 0.000 claims description 5
- 239000003999 initiator Substances 0.000 claims description 5
- 238000004519 manufacturing process Methods 0.000 claims description 5
- 150000003254 radicals Chemical class 0.000 claims description 5
- 238000001035 drying Methods 0.000 claims description 4
- 238000001914 filtration Methods 0.000 claims description 4
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 claims description 4
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims description 4
- MQIUGAXCHLFZKX-UHFFFAOYSA-N Di-n-octyl phthalate Natural products CCCCCCCCOC(=O)C1=CC=CC=C1C(=O)OCCCCCCCC MQIUGAXCHLFZKX-UHFFFAOYSA-N 0.000 claims description 3
- BJQHLKABXJIVAM-UHFFFAOYSA-N bis(2-ethylhexyl) phthalate Chemical compound CCCCC(CC)COC(=O)C1=CC=CC=C1C(=O)OCC(CC)CCCC BJQHLKABXJIVAM-UHFFFAOYSA-N 0.000 claims description 3
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 claims description 3
- GYNNXHKOJHMOHS-UHFFFAOYSA-N methyl-cycloheptane Natural products CC1CCCCCC1 GYNNXHKOJHMOHS-UHFFFAOYSA-N 0.000 claims description 3
- FRIBMENBGGCKPD-UHFFFAOYSA-N 3-(2,3-dimethoxyphenyl)prop-2-enal Chemical compound COC1=CC=CC(C=CC=O)=C1OC FRIBMENBGGCKPD-UHFFFAOYSA-N 0.000 claims description 2
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 claims description 2
- 235000019253 formic acid Nutrition 0.000 claims description 2
- 238000002156 mixing Methods 0.000 claims description 2
- BOUCRWJEKAGKKG-UHFFFAOYSA-N n-[3-(diethylaminomethyl)-4-hydroxyphenyl]acetamide Chemical compound CCN(CC)CC1=CC(NC(C)=O)=CC=C1O BOUCRWJEKAGKKG-UHFFFAOYSA-N 0.000 claims description 2
- 229910052708 sodium Inorganic materials 0.000 claims description 2
- 239000011734 sodium Substances 0.000 claims description 2
- 229940057950 sodium laureth sulfate Drugs 0.000 claims description 2
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 claims description 2
- CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 claims description 2
- 238000005406 washing Methods 0.000 claims description 2
- SXHLENDCVBIJFO-UHFFFAOYSA-M sodium;2-[2-(2-dodecoxyethoxy)ethoxy]ethyl sulfate Chemical compound [Na+].CCCCCCCCCCCCOCCOCCOCCOS([O-])(=O)=O SXHLENDCVBIJFO-UHFFFAOYSA-M 0.000 claims 1
- LPBNNQBYFCZCTA-UHFFFAOYSA-N sulfuric acid;1-tridecoxytridecane Chemical compound OS(O)(=O)=O.CCCCCCCCCCCCCOCCCCCCCCCCCCC LPBNNQBYFCZCTA-UHFFFAOYSA-N 0.000 claims 1
- 239000000243 solution Substances 0.000 description 32
- 239000002904 solvent Substances 0.000 description 30
- 238000002360 preparation method Methods 0.000 description 22
- 239000002253 acid Substances 0.000 description 16
- 239000012074 organic phase Substances 0.000 description 16
- 229920000642 polymer Polymers 0.000 description 14
- 238000006243 chemical reaction Methods 0.000 description 11
- 239000007864 aqueous solution Substances 0.000 description 10
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 9
- 229920002521 macromolecule Polymers 0.000 description 8
- 230000001590 oxidative effect Effects 0.000 description 8
- 229910052938 sodium sulfate Inorganic materials 0.000 description 8
- 235000011152 sodium sulphate Nutrition 0.000 description 8
- 239000000126 substance Substances 0.000 description 7
- 239000011541 reaction mixture Substances 0.000 description 6
- 150000007513 acids Chemical class 0.000 description 5
- 239000000463 material Substances 0.000 description 5
- 150000007524 organic acids Chemical class 0.000 description 5
- 238000012360 testing method Methods 0.000 description 5
- LCTONWCANYUPML-UHFFFAOYSA-N Pyruvic acid Chemical compound CC(=O)C(O)=O LCTONWCANYUPML-UHFFFAOYSA-N 0.000 description 4
- 239000000178 monomer Substances 0.000 description 4
- 239000008188 pellet Substances 0.000 description 4
- 235000006408 oxalic acid Nutrition 0.000 description 3
- 239000007800 oxidant agent Substances 0.000 description 3
- 238000011282 treatment Methods 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 229920001577 copolymer Polymers 0.000 description 2
- NNBZCPXTIHJBJL-UHFFFAOYSA-N decalin Chemical compound C1CCCC2CCCCC21 NNBZCPXTIHJBJL-UHFFFAOYSA-N 0.000 description 2
- 238000010556 emulsion polymerization method Methods 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 229920001519 homopolymer Polymers 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 230000003287 optical effect Effects 0.000 description 2
- 235000005985 organic acids Nutrition 0.000 description 2
- 230000003647 oxidation Effects 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- 239000003973 paint Substances 0.000 description 2
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 229940107700 pyruvic acid Drugs 0.000 description 2
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 2
- MIOPJNTWMNEORI-GMSGAONNSA-N (S)-camphorsulfonic acid Chemical compound C1C[C@@]2(CS(O)(=O)=O)C(=O)C[C@@H]1C2(C)C MIOPJNTWMNEORI-GMSGAONNSA-N 0.000 description 1
- RELMFMZEBKVZJC-UHFFFAOYSA-N 1,2,3-trichlorobenzene Chemical compound ClC1=CC=CC(Cl)=C1Cl RELMFMZEBKVZJC-UHFFFAOYSA-N 0.000 description 1
- WBIQQQGBSDOWNP-UHFFFAOYSA-N 2-dodecylbenzenesulfonic acid Chemical compound CCCCCCCCCCCCC1=CC=CC=C1S(O)(=O)=O WBIQQQGBSDOWNP-UHFFFAOYSA-N 0.000 description 1
- -1 3 H Chemical class 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 1
- 235000011114 ammonium hydroxide Nutrition 0.000 description 1
- 150000001448 anilines Chemical class 0.000 description 1
- 239000002216 antistatic agent Substances 0.000 description 1
- 239000000010 aprotic solvent Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 229920001940 conductive polymer Polymers 0.000 description 1
- 239000004020 conductor Substances 0.000 description 1
- 238000010494 dissociation reaction Methods 0.000 description 1
- 230000005593 dissociations Effects 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 229940060296 dodecylbenzenesulfonic acid Drugs 0.000 description 1
- 239000002019 doping agent Substances 0.000 description 1
- 239000007772 electrode material Substances 0.000 description 1
- 238000010894 electron beam technology Methods 0.000 description 1
- 238000006056 electrooxidation reaction Methods 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- SFNALCNOMXIBKG-UHFFFAOYSA-N ethylene glycol monododecyl ether Chemical compound CCCCCCCCCCCCOCCO SFNALCNOMXIBKG-UHFFFAOYSA-N 0.000 description 1
- 239000010408 film Substances 0.000 description 1
- 238000010528 free radical solution polymerization reaction Methods 0.000 description 1
- 238000011031 large-scale manufacturing process Methods 0.000 description 1
- 239000004973 liquid crystal related substance Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 230000015654 memory Effects 0.000 description 1
- IBIKHMZPHNKTHM-RDTXWAMCSA-N merck compound 25 Chemical compound C1C[C@@H](C(O)=O)[C@H](O)CN1C(C1=C(F)C=CC=C11)=NN1C(=O)C1=C(Cl)C=CC=C1C1CC1 IBIKHMZPHNKTHM-RDTXWAMCSA-N 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 230000000379 polymerizing effect Effects 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- 230000005588 protonation Effects 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 239000012266 salt solution Substances 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- KLYDBHUQNXKACI-UHFFFAOYSA-M sodium;2-[2-(2-tridecoxyethoxy)ethoxy]ethyl sulfate Chemical compound [Na+].CCCCCCCCCCCCCOCCOCCOCCOS([O-])(=O)=O KLYDBHUQNXKACI-UHFFFAOYSA-M 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000006276 transfer reaction Methods 0.000 description 1
- LEMQFBIYMVUIIG-UHFFFAOYSA-N trifluoroborane;hydrofluoride Chemical compound F.FB(F)F LEMQFBIYMVUIIG-UHFFFAOYSA-N 0.000 description 1
- 238000000870 ultraviolet spectroscopy Methods 0.000 description 1
Classifications
-
- 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
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Physics & Mathematics (AREA)
- Spectroscopy & Molecular Physics (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)
Description
・ポリアニリン塩のポリアニリン塩基への脱ドーピング、ポリアニリン塩基を非プロトン性溶媒へ溶解し、ポリアニリン塩へと再ドーピングする。この処理は、負担となり、製造費用を増加させる。
・置換ポリアニリンの調製、ポリアニリン塩のホモポリマーではないポリアニリンコポリマーの調製。前記置換ポリアニリンおよびコポリマーの導電率は、ポリアニリンよりもかなり低い。
・前記ポリアニリン塩の濃縮酸への溶解。しかし、濃縮酸を用いるため、それらは高い腐食性を有する。
・エマルジョン重合法による官能基性プロトン性酸を用いるポリアニリン塩の調製。
本発明の主な目的は、有機酸および芳香族アミンを用いるポリアニリン塩の調製方法を提供することである。
従って、本発明は、ポリアニリン塩が、有機溶媒および混合溶媒に可溶な溶液ならびに固体の両形態である、アニリンのポリアニリン塩への重合方法を提供する。
従って、本発明は、以下の工程を含む、ポリアニリン塩の改良された調製方法を提供する。
(a) アニオン界面活性剤を蒸留水に溶解し、ラジカル開始剤の有機溶媒溶液と混合することで、30℃-50℃の温度範囲で乳白色エマルジョンを得る工程、
(b) 芳香族アミンおよび有機酸の水溶性混合物を(a)工程のエマルジョンに滴下し、前記混合物を30℃-50℃の温度範囲で4〜24時間撹拌し、緑色エマルジョンを得る工程、
(c) (b)工程の前記緑色エマルジョンを静置し、そして、上部の水相と下部のポリアニリン塩を含む緑色油相とを分離する工程、
(d) (c)工程の前記緑色油相を水で数回洗浄し、それを過剰の無水硫酸ナトリウムで乾燥させ、濾過を行い、有機溶媒中のポリアニリン塩を得る工程、
(e) アセトンまたはギ酸に(d)工程の溶液を加えることによって、任意にポリアニリン塩を沈殿させる工程、および
(f) 前記沈殿した固体を分離し、約100℃で乾燥させ、固体ポリアニリン塩を得る工程。
導電率 = (厚さ)/(抵抗値 x 面積) = d/(RA)
本発明の主な長所は、(i)ポリアニリン塩が電気伝導性であり、前記ポリアニリン塩が他の溶媒および混合溶媒へ移転可能なキャリア有機溶媒中に存在する、マレイン酸を用いる前記ポリアニリン塩の調製、(2)粉末形態の前記ポリアニリン塩が溶媒および混合溶媒に可溶である。
Claims (14)
- 以下の工程を含む、重合によるポリアニリン塩の改良された調製方法。
(a) アニオン界面活性剤を蒸留水に溶解し、ラジカル開始剤の有機溶媒溶液と混合することで、30℃−50℃の温度範囲で乳白色エマルジョンを得る工程、
(b) 芳香族アミンおよびマレイン酸または無水マレイン酸の水溶性混合物を(a)工程のエマルジョンに滴下し、前記混合物を30℃−50℃の温度範囲で4〜24時間撹拌し、緑色エマルジョンを得る工程、
(c) (b)工程の前記緑色エマルジョンを静置し、そして、上部の水相と下部のポリアニリン塩を含む緑色油相とを分離する工程、
(d) (c)工程の前記緑色油相を水で数回洗浄し、それを過剰の無水硫酸ナトリウムで乾燥させ、濾過を行い、有機溶媒中のポリアニリン塩を得る工程、
(e) アセトンまたはギ酸に(d)工程の溶液を加えることによって、任意にポリアニリン塩を沈殿させる工程、および
(f) 前記沈殿した固体を分離し、100℃で乾燥させ、固体ポリアニリン塩を得る工程。 - (a)工程において使用される前記アニオン界面活性剤が、ラウレス硫酸アンモニウム、ラウレス硫酸ナトリウム、ラウリル硫酸ナトリウム、スルホン酸ナトリウム、およびトリデシルエーテル硫酸ナトリウムからなる群から選択される、請求項1記載の方法。
- (a)工程において使用される前記アニオン界面活性剤が、ラウリル硫酸ナトリウムである、請求項1記載の方法。
- (a)工程において使用される前記ラジカル開始剤が、ベンゾイルペルオキシド、t−ブチルヒドロペルオキシドおよびクメンヒドロペルオキシドからなる群から選択される、請求項1記載の方法。
- 使用される前記ラジカル開始剤が、ベンゾイルペルオキシドである、請求項1記載の方法。
- (a)工程において使用される前記有機溶媒が、クロロホルム、ジクロロメタン、ベンゾール、トルエンおよびキシレンからなる群から選択される、請求項1記載の方法。
- (b)工程において使用される前記芳香族アミンが、アニリンである、請求項1記載の方法。
- (d)工程において前記ポリアニリン塩が、キャリア有機溶媒中で得られる、請求項1記載の方法。
- (d)工程においてキャリア有機溶媒中の前記ポリアニリン塩が、電気伝導性である、請求項1記載の方法。
- (f)工程において粉末形態として得られる前記ポリアニリン塩が、電気伝導性である、請求項1記載の方法。
- (f)工程において得られる前記ポリアニリン塩が、有機溶媒または有機混合溶媒に可溶である、請求項1記載の方法。
- 使用される前記有機溶媒が、1−メチル−2−ピロリドン、N,N−ジメチルホルムアミド、ジメチルスルフォキサイド、クロロホルム、ジクロロメタン、ベンジン、トルエン、キシレン、ブタノール、デカノール、ドデカノール、シクロヘキサノール、メチルシクロヘキサン、ジオクチルフタレートまたはそれらの組み合わせからなる群から選択される、請求項1記載の方法。
- (b)工程において行われるエマルジョン重合の温度が、40℃である、請求項1記載
の方法。 - (b)工程において行われる重合の持続時間が、6時間である、請求項1記載の方法。
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
PCT/IB2002/004704 WO2004041911A1 (en) | 2002-11-06 | 2002-11-06 | A process for the preparation of polyaniline salt |
US10/290,458 US6942822B2 (en) | 2001-06-29 | 2002-11-08 | Process for the preparation of polyaniline salt |
Publications (3)
Publication Number | Publication Date |
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JP2006505649A JP2006505649A (ja) | 2006-02-16 |
JP2006505649A5 JP2006505649A5 (ja) | 2008-04-17 |
JP4262203B2 true JP4262203B2 (ja) | 2009-05-13 |
Family
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JP2004549395A Expired - Fee Related JP4262203B2 (ja) | 2002-11-06 | 2002-11-06 | ポリアニリン塩の調製方法 |
Country Status (5)
Country | Link |
---|---|
US (1) | US6942822B2 (ja) |
JP (1) | JP4262203B2 (ja) |
CN (1) | CN100354338C (ja) |
AU (1) | AU2002339693A1 (ja) |
WO (1) | WO2004041911A1 (ja) |
Families Citing this family (4)
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JP2009506156A (ja) * | 2005-08-26 | 2009-02-12 | カウンシル オブ サイエンティフィク アンド インダストリアル リサーチ | 導電性ポリマーの調製方法 |
TWI470856B (zh) * | 2013-10-11 | 2015-01-21 | Nanya Plastics Corp | An aluminum plastic packaging material for lithium batteries |
CN105524275B (zh) * | 2016-01-19 | 2017-11-10 | 四川大学 | 一种用于合成5‑羟甲基糠醛的改性聚苯胺催化剂的制备方法 |
CN114380995B (zh) * | 2022-03-23 | 2022-05-31 | 天津冶建特种材料有限公司 | 一种混凝土用导电聚苯胺的制备方法 |
Family Cites Families (7)
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US5728321A (en) * | 1988-09-30 | 1998-03-17 | Nitto Denko Corporation | Organic polymer, conducting organic polymer, production methods and uses of the same |
US5196144A (en) * | 1988-10-31 | 1993-03-23 | The Regents Of The University Of California | Electrically conductive polyaniline |
US5232631A (en) * | 1991-06-12 | 1993-08-03 | Uniax Corporation | Processible forms of electrically conductive polyaniline |
IL110318A (en) * | 1994-05-23 | 1998-12-27 | Al Coat Ltd | Solutions containing polyaniline for making transparent electrodes for liquid crystal devices |
US5567356A (en) * | 1994-11-07 | 1996-10-22 | Monsanto Company | Emulsion-polymerization process and electrically-conductive polyaniline salts |
US6586565B2 (en) * | 2000-11-17 | 2003-07-01 | Council Of Scientific & Industrial Research | Process for the preparation of a polyaniline salt |
US6630567B1 (en) * | 2002-03-13 | 2003-10-07 | Council Of Scientific And Industrial Research | Process for the preparation of polyaniline salt |
-
2002
- 2002-11-06 WO PCT/IB2002/004704 patent/WO2004041911A1/en active Application Filing
- 2002-11-06 AU AU2002339693A patent/AU2002339693A1/en not_active Abandoned
- 2002-11-06 JP JP2004549395A patent/JP4262203B2/ja not_active Expired - Fee Related
- 2002-11-06 CN CNB02830134XA patent/CN100354338C/zh not_active Expired - Fee Related
- 2002-11-08 US US10/290,458 patent/US6942822B2/en not_active Expired - Fee Related
Also Published As
Publication number | Publication date |
---|---|
US6942822B2 (en) | 2005-09-13 |
CN1720279A (zh) | 2006-01-11 |
AU2002339693A1 (en) | 2004-06-07 |
WO2004041911A1 (en) | 2004-05-21 |
US20040089848A1 (en) | 2004-05-13 |
JP2006505649A (ja) | 2006-02-16 |
CN100354338C (zh) | 2007-12-12 |
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