JP2011190452A - 電子工学用途のための、ポリマー酸コロイドを用いて製造された水分散性ポリアニリン - Google Patents
電子工学用途のための、ポリマー酸コロイドを用いて製造された水分散性ポリアニリン Download PDFInfo
- Publication number
- JP2011190452A JP2011190452A JP2011102939A JP2011102939A JP2011190452A JP 2011190452 A JP2011190452 A JP 2011190452A JP 2011102939 A JP2011102939 A JP 2011102939A JP 2011102939 A JP2011102939 A JP 2011102939A JP 2011190452 A JP2011190452 A JP 2011190452A
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- Prior art keywords
- dispersion
- acid
- colloid
- polyaniline
- polymer
- 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.)
- Granted
Links
- 229920000767 polyaniline Polymers 0.000 title claims abstract description 85
- 239000002253 acid Substances 0.000 title claims description 106
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 title claims description 77
- 239000000084 colloidal system Substances 0.000 title description 30
- 239000006185 dispersion Substances 0.000 claims abstract description 148
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims abstract description 115
- 239000000178 monomer Substances 0.000 claims abstract description 54
- 238000006116 polymerization reaction Methods 0.000 claims abstract description 40
- 238000000034 method Methods 0.000 claims abstract description 36
- 239000007800 oxidant agent Substances 0.000 claims abstract description 33
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims abstract description 32
- 239000011541 reaction mixture Substances 0.000 claims abstract description 16
- 238000002156 mixing Methods 0.000 claims abstract description 15
- 229920000642 polymer Polymers 0.000 claims description 89
- 239000000203 mixture Substances 0.000 claims description 64
- ROOXNKNUYICQNP-UHFFFAOYSA-N ammonium persulfate Chemical compound [NH4+].[NH4+].[O-]S(=O)(=O)OOS([O-])(=O)=O ROOXNKNUYICQNP-UHFFFAOYSA-N 0.000 claims description 54
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 claims description 32
- 229910001870 ammonium persulfate Inorganic materials 0.000 claims description 27
- 239000003456 ion exchange resin Substances 0.000 claims description 25
- 229920003303 ion-exchange polymer Polymers 0.000 claims description 25
- -1 perfluoroethylene sulfonic acid Chemical compound 0.000 claims description 23
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 22
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims description 20
- 239000003957 anion exchange resin Substances 0.000 claims description 17
- 238000004519 manufacturing process Methods 0.000 claims description 16
- 239000003729 cation exchange resin Substances 0.000 claims description 13
- 229910052757 nitrogen Inorganic materials 0.000 claims description 13
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 12
- 230000008569 process Effects 0.000 claims description 11
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 10
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims description 8
- 125000000217 alkyl group Chemical group 0.000 claims description 8
- 239000003054 catalyst Substances 0.000 claims description 8
- 229920001577 copolymer Polymers 0.000 claims description 8
- 229920002313 fluoropolymer Polymers 0.000 claims description 8
- 230000001590 oxidative effect Effects 0.000 claims description 8
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims description 6
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 6
- 125000003118 aryl group Chemical group 0.000 claims description 6
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 6
- 150000003512 tertiary amines Chemical class 0.000 claims description 6
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims description 5
- HYGWNUKOUCZBND-UHFFFAOYSA-N azanide Chemical group [NH2-] HYGWNUKOUCZBND-UHFFFAOYSA-N 0.000 claims description 5
- LCPVQAHEFVXVKT-UHFFFAOYSA-N 2-(2,4-difluorophenoxy)pyridin-3-amine Chemical group NC1=CC=CN=C1OC1=CC=C(F)C=C1F LCPVQAHEFVXVKT-UHFFFAOYSA-N 0.000 claims description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 4
- 229910052736 halogen Inorganic materials 0.000 claims description 4
- 150000002367 halogens Chemical group 0.000 claims description 4
- 230000003287 optical effect Effects 0.000 claims description 4
- USHAGKDGDHPEEY-UHFFFAOYSA-L potassium persulfate Chemical compound [K+].[K+].[O-]S(=O)(=O)OOS([O-])(=O)=O USHAGKDGDHPEEY-UHFFFAOYSA-L 0.000 claims description 4
- CHQMHPLRPQMAMX-UHFFFAOYSA-L sodium persulfate Substances [Na+].[Na+].[O-]S(=O)(=O)OOS([O-])(=O)=O CHQMHPLRPQMAMX-UHFFFAOYSA-L 0.000 claims description 4
- 239000004593 Epoxy Chemical group 0.000 claims description 3
- 229910021578 Iron(III) chloride Inorganic materials 0.000 claims description 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 3
- 125000002723 alicyclic group Chemical group 0.000 claims description 3
- 125000003342 alkenyl group Chemical group 0.000 claims description 3
- 125000004450 alkenylene group Chemical group 0.000 claims description 3
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 3
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 3
- 125000003282 alkyl amino group Chemical group 0.000 claims description 3
- 125000002877 alkyl aryl group Chemical group 0.000 claims description 3
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 3
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 3
- 125000006350 alkyl thio alkyl group Chemical group 0.000 claims description 3
- 125000004414 alkyl thio group Chemical group 0.000 claims description 3
- 125000002947 alkylene group Chemical group 0.000 claims description 3
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 3
- 125000005135 aryl sulfinyl group Chemical group 0.000 claims description 3
- 125000004391 aryl sulfonyl group Chemical group 0.000 claims description 3
- 125000005110 aryl thio group Chemical group 0.000 claims description 3
- 125000004104 aryloxy group Chemical group 0.000 claims description 3
- 125000001589 carboacyl group Chemical group 0.000 claims description 3
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 3
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 3
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 3
- 125000005843 halogen group Chemical group 0.000 claims description 3
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 claims description 3
- RUTXIHLAWFEWGM-UHFFFAOYSA-H iron(3+) sulfate Chemical compound [Fe+3].[Fe+3].[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O RUTXIHLAWFEWGM-UHFFFAOYSA-H 0.000 claims description 3
- 229910000360 iron(III) sulfate Inorganic materials 0.000 claims description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 3
- 229910052717 sulfur Inorganic materials 0.000 claims description 3
- 239000011593 sulfur Substances 0.000 claims description 3
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 claims description 2
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 claims description 2
- 239000006057 Non-nutritive feed additive Substances 0.000 claims description 2
- BULOCEWDRJUMEL-UHFFFAOYSA-N benzene formaldehyde Chemical compound C=O.C1=CC=CC=C1.C=O BULOCEWDRJUMEL-UHFFFAOYSA-N 0.000 claims description 2
- 239000012044 organic layer Substances 0.000 claims description 2
- 239000007788 liquid Substances 0.000 abstract description 14
- 239000010410 layer Substances 0.000 description 137
- 229920000557 Nafion® Polymers 0.000 description 46
- 239000000463 material Substances 0.000 description 35
- 229920001940 conductive polymer Polymers 0.000 description 22
- 238000003756 stirring Methods 0.000 description 22
- 239000010408 film Substances 0.000 description 20
- 239000011347 resin Substances 0.000 description 20
- 229920005989 resin Polymers 0.000 description 20
- 238000006243 chemical reaction Methods 0.000 description 17
- 239000008367 deionised water Substances 0.000 description 16
- 229910021641 deionized water Inorganic materials 0.000 description 16
- 239000000243 solution Substances 0.000 description 16
- 239000002245 particle Substances 0.000 description 15
- 239000007787 solid Substances 0.000 description 15
- 229910052751 metal Inorganic materials 0.000 description 14
- 239000002184 metal Substances 0.000 description 14
- 150000007513 acids Chemical class 0.000 description 13
- 230000002378 acidificating effect Effects 0.000 description 12
- 150000002500 ions Chemical class 0.000 description 12
- 239000011521 glass Substances 0.000 description 10
- 239000002585 base Substances 0.000 description 9
- 239000010409 thin film Substances 0.000 description 9
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 8
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 8
- 230000005669 field effect Effects 0.000 description 8
- 239000012530 fluid Substances 0.000 description 8
- 229920001467 poly(styrenesulfonates) Polymers 0.000 description 8
- 239000007864 aqueous solution Substances 0.000 description 7
- 238000005342 ion exchange Methods 0.000 description 7
- 229920000172 poly(styrenesulfonic acid) Polymers 0.000 description 7
- 150000003839 salts Chemical class 0.000 description 7
- BFKJFAAPBSQJPD-UHFFFAOYSA-N tetrafluoroethene Chemical group FC(F)=C(F)F BFKJFAAPBSQJPD-UHFFFAOYSA-N 0.000 description 7
- 101001102158 Homo sapiens Phosphatidylserine synthase 1 Proteins 0.000 description 6
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 6
- 102100039298 Phosphatidylserine synthase 1 Human genes 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 239000002041 carbon nanotube Substances 0.000 description 6
- 229910021393 carbon nanotube Inorganic materials 0.000 description 6
- 150000001768 cations Chemical group 0.000 description 6
- 238000002347 injection Methods 0.000 description 6
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- 238000002360 preparation method Methods 0.000 description 5
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- 238000004528 spin coating Methods 0.000 description 4
- 125000001273 sulfonato group Chemical group [O-]S(*)(=O)=O 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 241000579895 Chlorostilbon Species 0.000 description 3
- QYKIQEUNHZKYBP-UHFFFAOYSA-N Vinyl ether Chemical class C=COC=C QYKIQEUNHZKYBP-UHFFFAOYSA-N 0.000 description 3
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- 150000001298 alcohols Chemical class 0.000 description 3
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- 238000001246 colloidal dispersion Methods 0.000 description 3
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- DGEZNRSVGBDHLK-UHFFFAOYSA-N [1,10]phenanthroline Chemical compound C1=CN=C2C3=NC=CC=C3C=CC2=C1 DGEZNRSVGBDHLK-UHFFFAOYSA-N 0.000 description 1
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- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical group O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 1
- 229910052790 beryllium Inorganic materials 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
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- XZCJVWCMJYNSQO-UHFFFAOYSA-N butyl pbd Chemical compound C1=CC(C(C)(C)C)=CC=C1C1=NN=C(C=2C=CC(=CC=2)C=2C=CC=CC=2)O1 XZCJVWCMJYNSQO-UHFFFAOYSA-N 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
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- ZMIGMASIKSOYAM-UHFFFAOYSA-N cerium Chemical compound [Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce] ZMIGMASIKSOYAM-UHFFFAOYSA-N 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
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- 239000002131 composite material Substances 0.000 description 1
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- 238000007796 conventional method Methods 0.000 description 1
- 238000007334 copolymerization reaction Methods 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
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- OGPBJKLSAFTDLK-UHFFFAOYSA-N europium atom Chemical compound [Eu] OGPBJKLSAFTDLK-UHFFFAOYSA-N 0.000 description 1
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- 239000000835 fiber Substances 0.000 description 1
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- WSFSSNUMVMOOMR-UHFFFAOYSA-N formaldehyde Substances O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 1
- SLGWESQGEUXWJQ-UHFFFAOYSA-N formaldehyde;phenol Chemical compound O=C.OC1=CC=CC=C1 SLGWESQGEUXWJQ-UHFFFAOYSA-N 0.000 description 1
- 239000012634 fragment Substances 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
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- 239000010439 graphite Substances 0.000 description 1
- 229910002804 graphite Inorganic materials 0.000 description 1
- 229910021480 group 4 element Inorganic materials 0.000 description 1
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- 229910021476 group 6 element Inorganic materials 0.000 description 1
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- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
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- 230000007774 longterm Effects 0.000 description 1
- 238000004020 luminiscence type Methods 0.000 description 1
- 238000001755 magnetron sputter deposition Methods 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- 239000002082 metal nanoparticle Substances 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 150000004706 metal oxides Chemical class 0.000 description 1
- 239000002923 metal particle Substances 0.000 description 1
- 238000002488 metal-organic chemical vapour deposition Methods 0.000 description 1
- QLOAVXSYZAJECW-UHFFFAOYSA-N methane;molecular fluorine Chemical group C.FF QLOAVXSYZAJECW-UHFFFAOYSA-N 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012544 monitoring process Methods 0.000 description 1
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- 229910052755 nonmetal Inorganic materials 0.000 description 1
- 238000000059 patterning Methods 0.000 description 1
- 230000000737 periodic effect Effects 0.000 description 1
- 229920001568 phenolic resin Polymers 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 229920000768 polyamine Polymers 0.000 description 1
- 239000002685 polymerization catalyst Substances 0.000 description 1
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- 239000000047 product Substances 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 238000005215 recombination Methods 0.000 description 1
- 230000006798 recombination Effects 0.000 description 1
- 230000002441 reversible effect Effects 0.000 description 1
- IGLNJRXAVVLDKE-UHFFFAOYSA-N rubidium atom Chemical compound [Rb] IGLNJRXAVVLDKE-UHFFFAOYSA-N 0.000 description 1
- KZUNJOHGWZRPMI-UHFFFAOYSA-N samarium atom Chemical compound [Sm] KZUNJOHGWZRPMI-UHFFFAOYSA-N 0.000 description 1
- 238000007650 screen-printing Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 239000002356 single layer Substances 0.000 description 1
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- 241000894007 species Species 0.000 description 1
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- 229910052712 strontium Inorganic materials 0.000 description 1
- 238000000967 suction filtration Methods 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- ISIJQEHRDSCQIU-UHFFFAOYSA-N tert-butyl 2,7-diazaspiro[4.5]decane-7-carboxylate Chemical compound C1N(C(=O)OC(C)(C)C)CCCC11CNCC1 ISIJQEHRDSCQIU-UHFFFAOYSA-N 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 238000000427 thin-film deposition Methods 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- XOLBLPGZBRYERU-UHFFFAOYSA-N tin dioxide Chemical compound O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 description 1
- 229910001887 tin oxide Inorganic materials 0.000 description 1
- 238000004448 titration Methods 0.000 description 1
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- NLVXSWCKKBEXTG-UHFFFAOYSA-N vinylsulfonic acid Chemical class OS(=O)(=O)C=C NLVXSWCKKBEXTG-UHFFFAOYSA-N 0.000 description 1
- 229920003169 water-soluble polymer Polymers 0.000 description 1
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Abstract
【解決手段】(a)コロイド形成フッ素化ポリマースルホン酸との水性分散物を供給する工程と、および(b)酸化剤を、工程(a)の分散物と混合する工程と(c)アニリンモノマーを、工程(b)の分散物に混合して、ポリアニリンの水性分散物を得る工程、または、(b)アニリンモノマーを、工程(a)の分散物に混合する工程と、(c)酸化剤を、工程(b)の分散物と混合して、ポリアニリンの水性分散物を得る工程と、を含み、前記重合は、特定の補助分散液の存在下で行われ、前記補助分散液は、前記酸化剤または、前記アニリンモノマーの何れか最後に加えられたものの添加前の任意の点で、前記反応混合物に加えられることを特徴とする方法。
【選択図】なし
Description
アノード/バッファ層/ELポリマー/カソード
を一般的に有する。アノードは、典型的に、例えば、インジウム/酸化スズ(ITO)のような半導電性ELポリマーの別の充填π−帯中に正孔を注入する能力を有する、任意の材料である。アノードは、任意選択的に、ガラスまたはプラスチック基材上に支持されている。ELポリマーは、典型的に、ポリ(パラフェニレンビニレン)またはポリフルオレンのような共役半導電性ポリマーである。カソードは、典型的に、半導電性ELポリマーの別の空π*−帯中に電子を注入する能力を有する、任意の材料(例えば、CaまたはBa)である。
nは、0〜4の整数であり、
mは、1〜5の整数であるが、ただし、n+m=5であり、そして
R1は、独立して、出現するごとに同一であるかもしくは異なるように選択され、かつアルキル、アルケニル、アルコキシ、シクロアルキル、シクロアルケニル、アルカノイル、アルキルチオ(alkythio)、アリールオキシ、アルキルチオアルキル、アルキルアリール、アリールアルキル、アミノ、アルキルアミノ、ジアルキルアミノ、アリール、アルキルスルフィニル、アルコキシアルキル、アルキルスルホニル、アリールチオ、アリールスルフィニル、アルコキシカルボニル、アリールスルホニル、カルボン酸、ハロゲン、シアノ、または1つまたは複数のスルホン酸、カルボン酸、ハロ、ニトロ、シアノもしくはエポキシ部分によって置換されたアルキルから選択されるか、あるいは任意の2つのR1基が一緒になって、任意選択的に1つまたは複数の二価の窒素、イオウまたは酸素原子を含んでもよい3、4、5、6または7員の芳香族環もしくは脂環式環を完成するアルキレンまたはアルケニレン鎖を形成してもよい)を有するアニリンモノマーから誘導される。
−(O−CF2CFRf)a−O−CF2CFR’fSO3X
(式中、RfおよびR’fは、独立して、F、Cl、または炭素原子を1〜10個有する過フッ素化アルキル基であり、a=0、1または2であり、そしてXは、H、Li、Na、KまたはN(R1)(R2)(R3)(R4)であり、R1、R2、R3およびR4は、同一であるかまたは異なり、一実施形態において、H、CH3またはC2H5である)によって表される、過フッ素化されたものを含む、高度にフッ素化された炭素骨格および側鎖が挙げられる。もう1つの実施形態において、XはHである。上記の通り、Xは多価であってもよい。
−O−CF2CF(CF3)−O−CF2CF2SO3X
(式中、Xは、上記で定義された通りである)によって表されるペルフルオロカーボン骨格および側鎖を含む。この種類のFSAポリマーは米国特許公報(特許文献2)に開示されており、テトラフルオロエチレン(TFE)と、過フッ素化ビニルエーテルCF2=CF−O−CF2CF(CF3)−O−CF2CF2SO2F、ペルフルオロ(3,6−ジオキサ−4−メチル−7−オクテンスルホニルフロリド)(PDMOF)との共重合によって、続いて、フッ化スルホニル基の加水分解によるスルホネート基への転換、および必要であればそれらを所望のイオン型へと転換するためのイオン交換によって、製造することができる。側鎖−O−CF2CF2SO3X(式中、Xは上記の通りである)を有する種類の好ましいポリマーの例は、米国特許公報(特許文献3)および米国特許公報(特許文献4)に開示されている。テトラフルオロエチレン(TFE)と、過フッ素化ビニルエーテルCF2=CF−O−CF2CF2SO2F、ペルフルオロ(3−オキサ−4−ペンテンスルホニルフロリド)(POPF)との共重合、それに続く加水分解、および必要であればさらにイオン交換によって、このポリマーを製造することができる。
(a)コロイド形成ポリマー酸の水性分散物を供給する工程と、
(b)酸化剤を、工程(a)の分散物と混合する工程と、
(c)アニリンモノマーを、工程(b)の分散物と混合する工程と、
を含む。
この比較例は、オルメコン カンパニー(Ormecon Company)のD 005 W OLDから調製された乾燥固体の高い湿分取り込み、および再分散性を説明する。乾燥フィルムと接触する水の酸性度も説明する。
この比較例は、分散ポリアニリンがアニリンと水溶性PAAMSAから製造される、水性PAni/PAAMPSA分散物から調製された乾燥固体の再分散性を説明する。また水性分散物の酸性度も説明する。
この実施例は、分散ポリアニリンが、アニリンと、ナフィオン(Nafion)(登録商標)、コロイド状ペルフルオロエチレンスルホン酸とから製造される、水性PAni/ナフィオン(Nafion)(登録商標)分散物の調製を説明する。またこの実施例は、水性PAni/ナフィオン(Nafion)(登録商標)分散物から調製された乾燥固体の非分散性および低湿分取り込みも説明する。また、乾燥フィルムと接触する水の中性も説明する。
この実施例は、水性PAni/ナフィオン(Nafion)(登録商標)分散物の調製、ならびに分散物の安定性およびpHに及ぼす樹脂処理の影響を説明する。またこの実施例は、水性PAni/ナフィオン(Nafion)(登録商標)分散物から調製された乾燥固体の非分散性および低湿分取り込みも説明する。また、乾燥フィルムと接触する水の中性も説明する。
この参考例は、高pHの水性PAni/ナフィオン(Nafion)(登録商標)分散物の調製、およびデバイス特性を説明する。
室温で、500mL二重ジャケット付き反応容器中に直接、92.00gの脱イオン(DI)水および92.00gの99.7%n−プロパノールを集合させた。次に、ピペットを介して、3.58mL(43.59ミリモル)の37重量%HClおよび1.988mL(21.80ミリモル)のアニリン(蒸留)を反応容器に添加した。頭上に500RPMに設定されたU型撹拌ロッドを備えて、混合物を撹拌した。5分後、ガラス漏斗を介して、0.3μmプロフィールフィルターを通過した91.98g(10.90ミリモル)の水分散性ナフィオン(Nafion)(登録商標)(DE−1020、10.9%固体、920EW)をゆっくり添加した。さらに5分間、混合物を均質化させた。1時間かけて、シリンジ注入ポンプを介して、20gのDI水に溶解された1.99g(8.72ミリモル)の過硫酸アンモニウム(99.99+%)を反応物に滴下して添加した。8分後、溶液は淡いトルコ色に変わった。濃深緑色に変化する前に、溶液は濃青色へと進行した。APS添加開始後、混合物を90分間撹拌し、そして7.00gのアンバーリスト(Amberlyst)−15(ペンシルバニア州フィラデルフィアのローム アンド ハース カンパニー(Rohm and Haas Co.,Philadelphia,PA))カチオン交換樹脂(32%n−プロパノール(DI水中)混合物で数回すすぎ、窒素下で乾燥させた)を添加し、そして一晩200RPMで撹拌を開始した。翌朝、鋼メッシュを通して混合物を濾過し、アンバージェット(Amberjet)4400(OH)(ペンシルバニア州フィラデルフィアのローム アンド ハース カンパニー(Rohm and Haas Co.,Philadelphia,PA))アニオン交換樹脂(32%n−プロパノール(DI水中)混合物で数回すすぎ、窒素下で乾燥させた)と一緒に、pHが0.9から4.4へと変更するまで撹拌した。樹脂を再び濾過した。使用前、PVDF膜を有する0.45μmミリポア ミレックス(Millipore Millex)−HVシリンジフィルターを通して、分散物を濾過した。収量:32%n−プロパノール/68%DI水中4%固体を有する約300gの分散物。
600cd/m2における電圧および効率:3.45Vおよび9.8cd/A
−7Vにおける漏洩電流:2μA
80℃におけるt1/2(初期の輝度:412cd/m2):97時間
室温で、500mL二重ジャケット付き反応容器中に直接、88.11gの99.7%n−プロパノールおよび88.11gのDI水を集合させた。次に、ピペットを介して、0.167mL(2.0ミリモル)の37重量%HClおよび0.901mL(9.9ミリモル)のアニリン(蒸留)を反応容器に添加した。頭上に500RPMに設定されたU型撹拌ロッドを備えて、混合物を撹拌した。5分後、ガラス漏斗を介して、0.3μmプロフィールフィルターを通過した100.03g(11.90ミリモル)の水分散性ナフィオン(Nafion)(登録商標)(DE−1020、11.1%固体、935EW)をゆっくり添加した。さらに10分間、混合物を均質化させた。6時間かけて、シリンジ注入ポンプを介して、20gのDI水に溶解された2.82g(12.4ミリモル)の過硫酸アンモニウム(99.99+%)を反応物に滴下して添加した。7分後、溶液は淡いトルコ色に変わった。濃深緑色に変化する前に、溶液は濃青色へと進行した。APS添加開始後、混合物を360分間撹拌し、そして7.50gのアンバーリスト(Amberlyst)−15カチオン交換樹脂(32%n−プロパノール(DI水中)混合物で数回すすぎ、窒素下で乾燥させた)を添加し、そして一晩200RPMで撹拌を開始した。翌朝、鋼メッシュを通して混合物を濾過し、アンバージェット(Amberjet)4400(OH)アニオン交換樹脂(32%n−プロパノール(DI水中)混合物で数回すすぎ、窒素下で乾燥させた)と一緒に、pHが1.3から4.8へと変更するまで撹拌した。樹脂を再び濾過した。使用前、PVDF膜を有する0.45μmミリポア ミレックス(Millipore Millex)−HVシリンジフィルターを通して、分散物を濾過した。収量:31%n−プロパノール/69%DI水中4%固体を有する約270gの分散物。
600cd/m2における電圧および効率:3.56Vおよび10.3cd/A
−7Vにおける漏洩電流:6μA
80℃におけるt1/2(初期の輝度:490cd/m2):148時間
なお、本発明は、特許請求の範囲を含め、以下の発明を包含する。
1.ポリアニリンと、少なくとも1つのコロイド形成ポリマー酸との水性分散物を含むことを特徴とする組成物。
2.前記ポリアニリンが、次式IIおよび次式III:
nは、0〜4の整数であり、
mは、1〜5の整数であるが、ただし、n+m=5であり、そして
R1は、独立して、出現するごとに同一であるかもしくは異なるように選択され、かつアルキル、アルケニル、アルコキシ、シクロアルキル、シクロアルケニル、アルカノイル、アルキルチオ、アリールオキシ、アルキルチオアルキル、アルキルアリール、アリールアルキル、アミノ、アルキルアミノ、ジアルキルアミノ、アリール、アルキルスルフィニル、アルコキシアルキル、アルキルスルホニル、アリールチオ、アリールスルフィニル、アルコキシカルボニル、アリールスルホニル、カルボン酸、ハロゲン、シアノ、または1つまたは複数のスルホン酸、カルボン酸、ハロ、ニトロ、シアノもしくはエポキシ部分によって置換されたアルキルから選択されるか、あるいは任意の2つのR1基が一緒になって、任意選択的に1つまたは複数の二価の窒素、イオウまたは酸素原子を含んでもよい3、4、5、6または7員の芳香族環もしくは脂環式環を完成するアルキレンまたはアルケニレン鎖を形成してもよい)
から選択される式を有するアニリンモノマー単位を有することを特徴とする1に記載の組成物。
3.前記コロイド形成ポリマー酸が、ポリマースルホン酸、ポリマーカルボン酸、およびポリマーリン酸、またはポリマーアクリル酸、あるいはそれらの混合物から選択されることを特徴とする1または2に記載の組成物。
4.前記コロイド形成ポリマー酸が、ペルフルオロエチレンスルホン酸を含むことを特徴とする1または2に記載の組成物。
5.ポリアニリンと、少なくとも1つのコロイド形成ポリマー酸との水性分散物の製造方法であって、
(a)水とアニリンとの均質な水性混合物を供給する工程と、
(b)ポリマー酸の水性分散物を供給する工程と、
(c)前記アニリン混合物を、コロイド形成ポリマー酸の前記水性分散物に混合する工程と、
(d)任意の添加順序で、酸化剤および触媒を、工程(c)の前記分散物に混合する工程と
を含むことを特徴とする方法。
6.前記水性ポリアニリン分散物を、カチオン交換樹脂、アニオン交換樹脂またはそれらの混合物であるイオン交換樹脂の少なくとも1つと接触させる工程をさらに含むことを特徴とする5に記載の方法。
7.酸化剤、触媒、補助分散剤、補助酸、または全てのこれらの追加の加工助剤をさらに含むことを特徴とする5に記載の方法。
8.過硫酸ナトリウム、過硫酸カリウム、過硫酸アンモニウムまたはそれらの組合せから選択される酸化剤と、
硫酸第二鉄、塩化第二鉄またはそれらの混合物から選択される触媒と、
エーテル、アルコール、アルコールエーテル、環状エーテル、ケトン、ニトリル、スルホキシドおよびそれらの組合せから選択される補助分散剤と
をさらに含み、
そして前記分散物を、スルホン化スチレン−ジビニルベンゼンコポリマー、スルホン酸、スルホン化架橋スチレンポリマー、ベンゼン−ホルムアルデヒドスルホン酸、カルボン酸、アクリル酸、リン酸、第三級アミン、第四級アミンアニオン交換樹脂、およびそれらの混合物から選択されるイオン交換樹脂と接触させる工程をさらに含むことを特徴とする5に記載の方法。
9.ポリアニリンと、少なくともコロイド形成ポリマー酸との有機水性分散物を含む組成物から製造された、少なくとも1つの有機層を含むことを特徴とする有機電子デバイス。
10.9に記載のデバイスであって、前記デバイスは、光センサー、光スイッチ、フォトレジスター、フォトトランジスター、光電管、IR検出器、光電池、太陽電池、発光ダイオード、バイオセンサー、発光ダイオードディスプレーまたはダイオードレーザーであることを特徴とするデバイス。
Claims (10)
- ポリアニリンと、少なくとも1つのコロイド形成フッ素化ポリマースルホン酸との水性分散物の製造方法であって、
(a)コロイド形成フッ素化ポリマースルホン酸との水性分散物を供給する工程と、および、
(b)酸化剤を、工程(a)の分散物と混合する工程と、
(c)アニリンモノマーを、工程(b)の分散物に混合して、ポリアニリンの水性分散物を得る工程と、
または、
(b)アニリンモノマーを、工程(a)の分散物に混合する工程と、
(c)酸化剤を、工程(b)の分散物と混合して、ポリアニリンの水性分散物を得る工程と、
を含み、前記重合は、n−プロパノール、イソプロパノール、メタノール、ジメチルアセトアミド、ジメチルホルムアミド、N−メチルピロリドンおよびそれらの混合物から選択される補助分散液の存在下で行われ、
前記補助分散液は、前記酸化剤または、前記アニリンモノマーの何れか最後に加えられたものの添加前の任意の点で、前記反応混合物に加えられることを特徴とする方法。 - 請求項1に記載の製造方法であって、
(a)水とアニリンとの均質な水性混合物を供給する工程と、
(b)ポリマー酸の水性分散物を供給する工程と、
(c)前記アニリン混合物を、コロイド形成ポリマー酸の前記水性分散物に混合する工程と、
(d)任意の添加順序で、酸化剤および触媒を、工程(c)の前記分散物に混合する工程と
を含み、
前記補助分散液は、工程(d)の酸化剤の添加前に加えられることを特徴とする方法。 - 前記水性ポリアニリン分散物を、カチオン交換樹脂、アニオン交換樹脂またはそれらの混合物であるイオン交換樹脂の少なくとも1つと接触させる工程をさらに含むことを特徴とする請求項1または2に記載の方法。
- 触媒、補助酸、またはこれらの追加の加工助剤の両方をさらに含むことを特徴とする請求項1に記載の方法。
- 前記酸化剤は、過硫酸ナトリウム、過硫酸カリウム、過硫酸アンモニウムまたはそれらの組合せから選択され、
前記方法は、硫酸第二鉄、塩化第二鉄またはそれらの混合物から選択される触媒をさらに含み、
そして前記分散物を、スルホン化スチレン−ジビニルベンゼンコポリマー、スルホン酸、スルホン化架橋スチレンポリマー、ベンゼン−ホルムアルデヒドスルホン酸、カルボン酸、アクリル酸、リン酸、第三級アミン、第四級アミンアニオン交換樹脂、およびそれらの混合物から選択されるイオン交換樹脂と接触させる工程をさらに含むことを特徴とする請求項2に記載の方法。 - 前記ポリアニリンが、次式IIおよび次式III:
nは、0〜4の整数であり、
mは、1〜5の整数であるが、ただし、n+m=5であり、そして
R1は、独立して、出現するごとに同一であるかもしくは異なるように選択され、かつアルキル、アルケニル、アルコキシ、シクロアルキル、シクロアルケニル、アルカノイル、アルキルチオ、アリールオキシ、アルキルチオアルキル、アルキルアリール、アリールアルキル、アミノ、アルキルアミノ、ジアルキルアミノ、アリール、アルキルスルフィニル、アルコキシアルキル、アルキルスルホニル、アリールチオ、アリールスルフィニル、アルコキシカルボニル、アリールスルホニル、カルボン酸、ハロゲン、シアノ、または1つまたは複数のスルホン酸、カルボン酸、ハロ、ニトロ、シアノもしくはエポキシ部分によって置換されたアルキルから選択されるか、あるいは任意の2つのR1基が一緒になって、任意選択的に1つまたは複数の二価の窒素、イオウまたは酸素原子を含んでもよい3、4、5、6または7員の芳香族環もしくは脂環式環を完成するアルキレンまたはアルケニレン鎖を形成してもよい)
から選択される式を有するアニリンモノマー単位を有することを特徴とする請求項2に記載の方法。 - 前記コロイド形成フッ素化ポリマースルホン酸が、ペルフルオロエチレンスルホン酸を含むことを特徴とする請求項2に記載の方法。
- 請求項1〜7の何れか一項に記載の方法により得られた水性分散物。
- 請求項8の水性分散物から製造された、少なくとも1つの有機層を含むことを特徴とする有機電子デバイス。
- 請求項9に記載のデバイスであって、前記デバイスは、光センサー、光スイッチ、フォトレジスター、フォトトランジスター、光電管、IR検出器、光電池、太陽電池、発光ダイオード、バイオセンサー、発光ダイオードディスプレーまたはダイオードレーザーであることを特徴とするデバイス。
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- 2003-09-24 WO PCT/US2003/030512 patent/WO2004029133A1/en active Application Filing
- 2003-09-24 JP JP2004540020A patent/JP2006500461A/ja active Pending
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Publication number | Publication date |
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KR101148285B1 (ko) | 2012-05-21 |
AU2003279014A1 (en) | 2004-04-19 |
JP2006500461A (ja) | 2006-01-05 |
US7462298B2 (en) | 2008-12-09 |
CN1681869A (zh) | 2005-10-12 |
US20040127637A1 (en) | 2004-07-01 |
WO2004029133A1 (en) | 2004-04-08 |
JP5562899B2 (ja) | 2014-07-30 |
US20090072201A1 (en) | 2009-03-19 |
EP1549696A1 (en) | 2005-07-06 |
CN1681869B (zh) | 2010-05-26 |
CA2499364A1 (en) | 2004-04-08 |
KR20050061475A (ko) | 2005-06-22 |
HK1080875A1 (en) | 2006-05-04 |
US8318046B2 (en) | 2012-11-27 |
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