FI113374B - Processabila former av elledande polyanilin och därav formade ledande produkter - Google Patents
Processabila former av elledande polyanilin och därav formade ledande produkter Download PDFInfo
- Publication number
- FI113374B FI113374B FI935498A FI935498A FI113374B FI 113374 B FI113374 B FI 113374B FI 935498 A FI935498 A FI 935498A FI 935498 A FI935498 A FI 935498A FI 113374 B FI113374 B FI 113374B
- Authority
- FI
- Finland
- Prior art keywords
- polyaniline
- conductive
- acid
- conductive polymer
- substrate
- Prior art date
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- 229920000767 polyaniline Polymers 0.000 title claims abstract description 239
- 229920000642 polymer Polymers 0.000 claims abstract description 138
- 239000002253 acid Substances 0.000 claims abstract description 118
- 239000000203 mixture Substances 0.000 claims abstract description 103
- 239000000758 substrate Substances 0.000 claims abstract description 100
- 239000002904 solvent Substances 0.000 claims abstract description 72
- 238000000034 method Methods 0.000 claims abstract description 71
- 239000000243 solution Substances 0.000 claims description 138
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims description 72
- -1 2-ethylhexyl Chemical group 0.000 claims description 71
- 239000000463 material Substances 0.000 claims description 59
- 229920001940 conductive polymer Polymers 0.000 claims description 55
- 239000008096 xylene Substances 0.000 claims description 44
- 239000007788 liquid Substances 0.000 claims description 42
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 41
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 36
- 125000000217 alkyl group Chemical group 0.000 claims description 36
- 239000007787 solid Substances 0.000 claims description 35
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 33
- 125000004432 carbon atom Chemical group C* 0.000 claims description 26
- 239000000835 fiber Substances 0.000 claims description 26
- 239000004698 Polyethylene Substances 0.000 claims description 23
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 23
- 239000000047 product Substances 0.000 claims description 23
- 125000003545 alkoxy group Chemical group 0.000 claims description 19
- 229920000573 polyethylene Polymers 0.000 claims description 19
- 239000004014 plasticizer Substances 0.000 claims description 18
- 229920000547 conjugated polymer Polymers 0.000 claims description 17
- 239000000178 monomer Substances 0.000 claims description 17
- 229920001778 nylon Polymers 0.000 claims description 17
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 16
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 16
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 15
- 239000004793 Polystyrene Substances 0.000 claims description 15
- 239000003960 organic solvent Substances 0.000 claims description 15
- 239000004677 Nylon Substances 0.000 claims description 14
- 239000004417 polycarbonate Substances 0.000 claims description 14
- 229920000515 polycarbonate Polymers 0.000 claims description 14
- 229920002223 polystyrene Polymers 0.000 claims description 14
- 229910052736 halogen Inorganic materials 0.000 claims description 13
- 230000008569 process Effects 0.000 claims description 13
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 12
- 125000003118 aryl group Chemical group 0.000 claims description 12
- 239000012530 fluid Substances 0.000 claims description 12
- 239000000126 substance Substances 0.000 claims description 12
- 239000004743 Polypropylene Substances 0.000 claims description 11
- 229920000139 polyethylene terephthalate Polymers 0.000 claims description 11
- 239000005020 polyethylene terephthalate Substances 0.000 claims description 11
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 10
- 150000002367 halogens Chemical class 0.000 claims description 10
- 150000002500 ions Chemical class 0.000 claims description 10
- 229920001155 polypropylene Polymers 0.000 claims description 10
- 125000003342 alkenyl group Chemical group 0.000 claims description 9
- 239000004020 conductor Substances 0.000 claims description 9
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims description 8
- JHWNWJKBPDFINM-UHFFFAOYSA-N Laurolactam Chemical compound O=C1CCCCCCCCCCCN1 JHWNWJKBPDFINM-UHFFFAOYSA-N 0.000 claims description 8
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 8
- 229920000299 Nylon 12 Polymers 0.000 claims description 8
- 150000001335 aliphatic alkanes Chemical class 0.000 claims description 8
- 229920001577 copolymer Polymers 0.000 claims description 8
- 229910052757 nitrogen Inorganic materials 0.000 claims description 8
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 7
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 7
- 230000000379 polymerizing effect Effects 0.000 claims description 7
- XFRVVPUIAFSTFO-UHFFFAOYSA-N 1-Tridecanol Chemical compound CCCCCCCCCCCCCO XFRVVPUIAFSTFO-UHFFFAOYSA-N 0.000 claims description 6
- NXXYKOUNUYWIHA-UHFFFAOYSA-N 2,6-Dimethylphenol Chemical compound CC1=CC=CC(C)=C1O NXXYKOUNUYWIHA-UHFFFAOYSA-N 0.000 claims description 6
- YCOXTKKNXUZSKD-UHFFFAOYSA-N 3,4-xylenol Chemical compound CC1=CC=C(O)C=C1C YCOXTKKNXUZSKD-UHFFFAOYSA-N 0.000 claims description 6
- PTFIPECGHSYQNR-UHFFFAOYSA-N 3-Pentadecylphenol Chemical compound CCCCCCCCCCCCCCCC1=CC=CC(O)=C1 PTFIPECGHSYQNR-UHFFFAOYSA-N 0.000 claims description 6
- 239000004593 Epoxy Substances 0.000 claims description 6
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims description 6
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 6
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 6
- 125000002877 alkyl aryl group Chemical group 0.000 claims description 6
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 6
- 125000004414 alkyl thio group Chemical group 0.000 claims description 6
- 150000001448 anilines Chemical class 0.000 claims description 6
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 6
- DIKBFYAXUHHXCS-UHFFFAOYSA-N bromoform Chemical compound BrC(Br)Br DIKBFYAXUHHXCS-UHFFFAOYSA-N 0.000 claims description 6
- 125000001589 carboacyl group Chemical group 0.000 claims description 6
- NOPFSRXAKWQILS-UHFFFAOYSA-N docosan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCCCCCO NOPFSRXAKWQILS-UHFFFAOYSA-N 0.000 claims description 6
- LQZZUXJYWNFBMV-UHFFFAOYSA-N dodecan-1-ol Chemical compound CCCCCCCCCCCCO LQZZUXJYWNFBMV-UHFFFAOYSA-N 0.000 claims description 6
- 229920002857 polybutadiene Polymers 0.000 claims description 6
- 125000001424 substituent group Chemical group 0.000 claims description 6
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 claims description 6
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 5
- 125000004391 aryl sulfonyl group Chemical group 0.000 claims description 5
- 229920000307 polymer substrate Polymers 0.000 claims description 5
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 claims description 4
- 239000005062 Polybutadiene Substances 0.000 claims description 4
- 125000002723 alicyclic group Chemical group 0.000 claims description 4
- 125000004450 alkenylene group Chemical group 0.000 claims description 4
- 125000006350 alkyl thio alkyl group Chemical group 0.000 claims description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 4
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 4
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 4
- 150000002576 ketones Chemical class 0.000 claims description 4
- SNQQPOLDUKLAAF-UHFFFAOYSA-N nonylphenol Chemical compound CCCCCCCCCC1=CC=CC=C1O SNQQPOLDUKLAAF-UHFFFAOYSA-N 0.000 claims description 4
- 229960003742 phenol Drugs 0.000 claims description 4
- 239000011593 sulfur Substances 0.000 claims description 4
- 229910052717 sulfur Inorganic materials 0.000 claims description 4
- 239000001993 wax Substances 0.000 claims description 4
- XIIIHRLCKLSYNH-UHFFFAOYSA-N 4-Hexyloxyphenol Chemical compound CCCCCCOC1=CC=C(O)C=C1 XIIIHRLCKLSYNH-UHFFFAOYSA-N 0.000 claims description 3
- JJWVPHWHEGQZOE-UHFFFAOYSA-N 4-dodecylbenzene-1,3-diol Chemical compound CCCCCCCCCCCCC1=CC=C(O)C=C1O JJWVPHWHEGQZOE-UHFFFAOYSA-N 0.000 claims description 3
- ASMQGLCHMVWBQR-UHFFFAOYSA-N Diphenyl phosphate Chemical group C=1C=CC=CC=1OP(=O)(O)OC1=CC=CC=C1 ASMQGLCHMVWBQR-UHFFFAOYSA-N 0.000 claims description 3
- IGFHQQFPSIBGKE-UHFFFAOYSA-N Nonylphenol Natural products CCCCCCCCCC1=CC=C(O)C=C1 IGFHQQFPSIBGKE-UHFFFAOYSA-N 0.000 claims description 3
- NBIIXXVUZAFLBC-UHFFFAOYSA-L Phosphate ion(2-) Chemical compound OP([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-L 0.000 claims description 3
- ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical compound OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 claims description 3
- 150000001298 alcohols Chemical class 0.000 claims description 3
- 150000001336 alkenes Chemical class 0.000 claims description 3
- 125000005233 alkylalcohol group Chemical group 0.000 claims description 3
- 125000002947 alkylene group Chemical group 0.000 claims description 3
- 125000005135 aryl sulfinyl group Chemical group 0.000 claims description 3
- 125000004104 aryloxy group Chemical group 0.000 claims description 3
- 229950005228 bromoform Drugs 0.000 claims description 3
- 238000000576 coating method Methods 0.000 claims description 3
- 150000001924 cycloalkanes Chemical class 0.000 claims description 3
- 229960000735 docosanol Drugs 0.000 claims description 3
- 229940060296 dodecylbenzenesulfonic acid Drugs 0.000 claims description 3
- BFMKFCLXZSUVPI-UHFFFAOYSA-N ethyl but-3-enoate Chemical compound CCOC(=O)CC=C BFMKFCLXZSUVPI-UHFFFAOYSA-N 0.000 claims description 3
- IVQOVYWBHRSGJI-UHFFFAOYSA-N hexyl 4-methylbenzenesulfonate Chemical compound CCCCCCOS(=O)(=O)C1=CC=C(C)C=C1 IVQOVYWBHRSGJI-UHFFFAOYSA-N 0.000 claims description 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 3
- 239000000155 melt Substances 0.000 claims description 3
- VUQUOGPMUUJORT-UHFFFAOYSA-N methyl 4-methylbenzenesulfonate Chemical compound COS(=O)(=O)C1=CC=C(C)C=C1 VUQUOGPMUUJORT-UHFFFAOYSA-N 0.000 claims description 3
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 3
- 239000003921 oil Substances 0.000 claims description 3
- 150000002989 phenols Chemical class 0.000 claims description 3
- 229920002492 poly(sulfone) Polymers 0.000 claims description 3
- 239000002243 precursor Substances 0.000 claims description 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 3
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 claims description 3
- 150000003460 sulfonic acids Chemical group 0.000 claims description 3
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 3
- 229920001169 thermoplastic Polymers 0.000 claims description 3
- WBIQQQGBSDOWNP-UHFFFAOYSA-N 2-dodecylbenzenesulfonic acid Chemical compound CCCCCCCCCCCCC1=CC=CC=C1S(O)(=O)=O WBIQQQGBSDOWNP-UHFFFAOYSA-N 0.000 claims description 2
- QTWJRLJHJPIABL-UHFFFAOYSA-N 2-methylphenol;3-methylphenol;4-methylphenol Chemical compound CC1=CC=C(O)C=C1.CC1=CC=CC(O)=C1.CC1=CC=CC=C1O QTWJRLJHJPIABL-UHFFFAOYSA-N 0.000 claims description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 2
- 229920002292 Nylon 6 Polymers 0.000 claims description 2
- 239000007983 Tris buffer Substances 0.000 claims description 2
- 125000005110 aryl thio group Chemical group 0.000 claims description 2
- 229960000846 camphor Drugs 0.000 claims description 2
- 238000004891 communication Methods 0.000 claims description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- 229920005570 flexible polymer Polymers 0.000 claims description 2
- QAOWNCQODCNURD-UHFFFAOYSA-M hydrogensulfate Chemical compound OS([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-M 0.000 claims description 2
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 2
- KDQQMEAEIKFPLQ-UHFFFAOYSA-N n-(1-cyanocyclohexyl)-2-fluorobenzamide Chemical compound FC1=CC=CC=C1C(=O)NC1(C#N)CCCCC1 KDQQMEAEIKFPLQ-UHFFFAOYSA-N 0.000 claims description 2
- 230000035699 permeability Effects 0.000 claims description 2
- WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 claims description 2
- 229920002037 poly(vinyl butyral) polymer Polymers 0.000 claims description 2
- 229920001195 polyisoprene Polymers 0.000 claims description 2
- 229920001296 polysiloxane Polymers 0.000 claims description 2
- 239000012265 solid product Substances 0.000 claims description 2
- 239000004416 thermosoftening plastic Substances 0.000 claims description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims 6
- 150000005215 alkyl ethers Chemical class 0.000 claims 2
- 150000003863 ammonium salts Chemical class 0.000 claims 2
- QGJOPFRUJISHPQ-NJFSPNSNSA-N carbon disulfide-14c Chemical compound S=[14C]=S QGJOPFRUJISHPQ-NJFSPNSNSA-N 0.000 claims 2
- 150000001925 cycloalkenes Chemical class 0.000 claims 2
- 239000000428 dust Substances 0.000 claims 2
- 239000002480 mineral oil Substances 0.000 claims 2
- 235000010446 mineral oil Nutrition 0.000 claims 2
- 238000007493 shaping process Methods 0.000 claims 2
- RAADJDWNEAXLBL-UHFFFAOYSA-N 1,2-di(nonyl)naphthalene Chemical compound C1=CC=CC2=C(CCCCCCCCC)C(CCCCCCCCC)=CC=C21 RAADJDWNEAXLBL-UHFFFAOYSA-N 0.000 claims 1
- FEXBEKLLSUWSIM-UHFFFAOYSA-N 2-Butyl-4-methylphenol Chemical compound CCCCC1=CC(C)=CC=C1O FEXBEKLLSUWSIM-UHFFFAOYSA-N 0.000 claims 1
- WEUIUHILWVJOPZ-UHFFFAOYSA-N 2-dodecyl-3-ethylbenzenesulfonic acid Chemical compound CCCCCCCCCCCCC1=C(CC)C=CC=C1S(O)(=O)=O WEUIUHILWVJOPZ-UHFFFAOYSA-N 0.000 claims 1
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 claims 1
- NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-UHFFFAOYSA-N 0.000 claims 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims 1
- WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 claims 1
- 150000001252 acrylic acid derivatives Chemical class 0.000 claims 1
- 239000000853 adhesive Substances 0.000 claims 1
- 230000001070 adhesive effect Effects 0.000 claims 1
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- 125000003700 epoxy group Chemical group 0.000 claims 1
- 125000001475 halogen functional group Chemical group 0.000 claims 1
- 239000000976 ink Substances 0.000 claims 1
- DXGLGDHPHMLXJC-UHFFFAOYSA-N oxybenzone Chemical compound OC1=CC(OC)=CC=C1C(=O)C1=CC=CC=C1 DXGLGDHPHMLXJC-UHFFFAOYSA-N 0.000 claims 1
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- 239000007921 spray Substances 0.000 claims 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 claims 1
- 150000007513 acids Chemical class 0.000 abstract description 26
- 239000010408 film Substances 0.000 description 117
- RLSSMJSEOOYNOY-UHFFFAOYSA-N m-cresol Chemical compound CC1=CC=CC(O)=C1 RLSSMJSEOOYNOY-UHFFFAOYSA-N 0.000 description 62
- 239000012528 membrane Substances 0.000 description 37
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 24
- NNBZCPXTIHJBJL-UHFFFAOYSA-N decalin Chemical compound C1CCCC2CCCCC21 NNBZCPXTIHJBJL-UHFFFAOYSA-N 0.000 description 20
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- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 9
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- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 7
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- PBKONEOXTCPAFI-UHFFFAOYSA-N 1,2,4-trichlorobenzene Chemical compound ClC1=CC=C(Cl)C(Cl)=C1 PBKONEOXTCPAFI-UHFFFAOYSA-N 0.000 description 6
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
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- ROOXNKNUYICQNP-UHFFFAOYSA-N ammonium persulfate Chemical compound [NH4+].[NH4+].[O-]S(=O)(=O)OOS([O-])(=O)=O ROOXNKNUYICQNP-UHFFFAOYSA-N 0.000 description 4
- 230000005540 biological transmission Effects 0.000 description 4
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- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 4
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- 229910052737 gold Inorganic materials 0.000 description 4
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- 239000002244 precipitate Substances 0.000 description 1
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- KCXFHTAICRTXLI-UHFFFAOYSA-N propane-1-sulfonic acid Chemical compound CCCS(O)(=O)=O KCXFHTAICRTXLI-UHFFFAOYSA-N 0.000 description 1
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- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 description 1
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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
-
- 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
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/80—Constructional details
- H10K50/805—Electrodes
- H10K50/81—Anodes
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- Physics & Mathematics (AREA)
- Chemical & Material Sciences (AREA)
- Optics & Photonics (AREA)
- Medicinal Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
- Polymers With Sulfur, Phosphorus Or Metals In The Main Chain (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Conductive Materials (AREA)
Claims (30)
1 S/cm. 113374
1. En elektriskt ledande polymersammansättning, vilken omfat-tar 20 (i) ett organiskt substrat valt mellan bulkpolymer och en > blandning av bulkpolymer med ett organiskt lösningsmedel, • ^ varvid nämnda substrat är flytande eller kan göras flytande genom smältning, dess ledningsförmäga är under 10‘8 S-cm"1 och : dess dielektricitetskonstant är under 22 vid rumstemperatur; :v.* 25 (ii) polyanilin, vars molvikt tili sitt viktmedeltal är över 10000 dalton och väri den repeterande anilinenheten är N-osubstituerad; i blandning med ’ . 30 (iii) en effektiv protonerande mängd protonsyra, vilken inne- häller en motjon som är funktionaliserad att lösa sig i sub-·’ stratet, varvid nämnda syra med polyanilinet formar ett kom- plex vars ledningsförmäga är större än ca 10“3 S/cm, och vars formel är * 113374 A - Ri VI väri A är sulfonsyra, fosfonsyra, vätesulfat eller vätefosfat; 5 och Ri är (R)V -ö. <H>'- VII väri 10 m* är 4 och n* är 1 och R* är alkyl, alkenyl eller alkoxy med 2-14 kolatomer, eller alkyl substituerad med en eller flere karboxylsyra-, halogen-, nitro-, cyano- eller epoxigrupper; eller A är HOSO2- och Ri on är vald ur mängden bestäende av 15 grupperna (L, D)-10-kamfer-, O-anisidin-5-, hydroxibenzen-, 2-hydroxi-4-metoxi-bentsofenon-, dinonylnaftalen-, 4-morfolinetan- och 2-{[tris(hydroxymetyl)metyl]amino}-l-etan-; eller A är vätefosfat och Ri är bis(2-etylhexyl-; ’’ 20 eller A-Ri är difenylvätefosfat; * · · » » · * I » varvid nämnda ledande polymersammansättning i fast tillständ * * · * * 1 har en mikrostruktur som omfattar en kontinuerlig fas som om-25 fattar polyanilinet och protonsyran med dess funktionaliserade motjon.
‘ 2. Ledande polymersammansättning enligt patentkrav 1, vilken omfattar tillräckligt polyanilin och protonsyra för att polya-30 nilin skall uppkomma vars ledningsförmäga är ätminstone ca 10"
3. Ledande polymersammansättning enligt patentkrav 1, i vilken substratet omfattar ett lösningsmedel i vilket den funktiona-liserade motjonen är löslig.
4. Ledande polymersaxnmansättning enligt patentkrav 1, i vilken substratet omfattar en bulkpolymer i vilken den funktiona-liserade motjonen är löslig.
5. Ledande polymersammansättning enligt patentkrav 1, i vilken 10 substratet omfattar ett lösningsmedel samt en bulkpolymer och den funktionaliserade motjonen är löslig i vardera.
6. Ledande polymersammansättning enligt patentkrav 1, vilken omfattar ätminstone ca 10 viktprocent substrat, och vilken är 15 en fast substans vars mikrostruktur omfattar polyanilinet och protonsyran med dess funktionaliserade motjon.
7. Ledande polymersammansättning enligt patentkrav 1, vilken omfattar tillräckligt polyanilin och funktionaliserad proton- 20 syra för att protonerat polyanilin skall uppkomma vars led-ningsförmäga är ätminstone ca 3 x 102 S/cm.
» ,:. 8. Ledande polymersammansättning enligt patentkrav 1, i vilken t » * * : polyanilinets molvikt till sitt viktmedeltal överstiger ca 10 25 000 och är framställt genom polymerisation av ett anilin med formeln • » · j. X v !··: <H)m (R>n vari n är ett heltal i intervallet 0-4, 30 m är ett heltal i intervallet 1-5 förutsatt att summan n+m är 5; 113374 R representerar var gang samma eller varierande substituent, nämligen alkyl, alkenyl, alkoxy, sykloalkyl, cykloalkenyl, al-kanoyl, alkyltio, aryloxy, alkyltioalkyl, alkylaryl, arylal-kyl, alkylsulfinyl, alkoxyalkyl, alkylsulfonyl, aryl, aryltio, 5 arylsulfinyl, alkoxykarbonyl, arylsulfonyl, karboxylsyra, halogen, cyano eller alkyl substituerad med en eller flere sul-fonsyror, karboxylsyror, halogen, nitro, cyano eller epoxy; eller vilka som heist R-substituenter kan tillsamans forma en alkylen- eller alkenylengrupp, som kompletterar en aromatisk 10 eller alicyklisk 3-, 4-, 5-, 6- eller 7-kolring, vilken ring kan innehälla en eller flere tvavärda kväve-, svavel-, sulfin-yl-, sulfonyl- eller syreheteroatomer.
9. Ledande polymersammansättning enligt patentkrav 8, väri m 15 är 5 och n är 0, varvid anilinet utgörs av osubstituerat ani- lin.
10. Ledande polymersammansättning enligt patentkrav 1, vilken omfattar polyanilin samt dodekylbensensulfonsyra vilken med 20 polyanilinet formar ett komplex i mängden 5-95 % och vars led-ningsförmäga är ca 10”8 S/cm eller större. * * · » · I f · • » ·
11. Ledande polymersammansättning enligt patentkrav 1, vilken ; .·. omfattar mjukgörare vald ur gruppen vilken omfattar: 4- 1 · · » » » · 25 hexyloxyfenol, 3-pentadekylfenol, nonylfenol, 4- dodekylresorcinol, 4-(tert.oktyl) fenol, 2, 6-ditert.butyl-4-metylfenol, 3,4-dimetylfenol, 2,6-dimetylfenol, metylparatolu-I. ensulfonat, etylparatoluensulfonat, n-hexylparatoluensulfonat, etyldodekylbensensulfonsyra, isopropylaminalkylarylsulfonat, 30 1-dodekanol, 1-tridekanol, 1-dokosanol, etoxylat med formeln CH3(CH2)xCH2(OCH2CH2)nOH, i vilka x=10-14, n=l,3; x=6, 8, n=l,0; x=10-12, n=3; x=6-8, n=2; poly(oxy-1,2-etandiyl), a-(nonyl-fenoxy)-ω-hydroxy och sulfaterat alkylalkoholetoxylatammonium-salt. 89 1 13374
12. Ledande polymersammansättning enligt patentkrav 1, i vil-ken dielektricitetskonstanten hos nämnda lösningsmedel är mindre än ca 22 och i vilken lösningsmedlet väljs ur gruppen 5 omfattande alkaner och alkener med ca 5 - ca 12 kolatomer, mi-neralolja, aromatiska föreningar, halogenerade aromatiska fö-reningar, halogenerade alkaner och alifatiska alkoholer, al-kyletrar och ketoner med ca 4 - ca 12 kolatomer, cykloalkaner, cykloalkener, koltetraklorid, koldisulfid, kloroform, bromo-10 form, diklormetan, morfolin, anilin, alkylbensener, xylen, töllien, dekahydronaftalen, styren, bensylalkohol, naftalen, fender och kresoler.
13. Ledande polymersammansättning enligt patentkrav 1, i vil-15 ken substratet ytterligare omfattar mjukgörare i vätskeform.
14. Ledande polymersammansättning enligt patentkrav 13, i vilken mjukgöraren väljs ur gruppen vilken omfattar: 4-hexyloxyfenol, 3-pentadekylfenol, nonylfenol, 4- 20 dodekylresorcinol, 4-(tert.oktyl)fenol, 2,6-ditert.butyl-4- metylfenol, 3,4-dimetylfenol, 2, 6-dimetylfenol, metylparatolu- ensulfonat, etylparatoluensulfonat, n-hexylparatoluensulfonat, ,:. etyldodekylbensensulfonsyra, isopropylaminalkylarylsulfonat, ' « * ¥ : 1-dodekanol, 1-tridekanol, 1-dokosanol, etoxylat med formeln I I · t I * I
15. Ledande polymersammansättning enligt patentkrav 4, i vil- ,···. ken polymeren väljs ur gruppen vilken omfattar polyetylener, * » isotaktisk polypropen, polystyren, poly (etylvinylacetat) , po-lybutadien, polyisopren, etylenvinylenkopolymerer, * » poly(vinylklorid), etylenpropylenkopolymerer, polysiloxan, po- 113374 lysulfon, polykarbonater, poly(etylentereftalat), homo- och kopolymerer av akrylonitril, poly(butylentereftalat) och nylon 12, nylon 8, nylon 6, nylon 6.6, nylon 4.6, amorf nylon, poly(vinylacetat), poly(vinylbutyral) och po-5 ly(vinylpyrrolidon).
16. Ledande polymersammansättning enligt patentkrav 1, vari substratet omfattar smält eller vätskeformig oligomer eller polymer. 10
17. Ledande polymersammansättning enligt patentkrav 1, varvid sammansättningen kan solidifieras till en transparent ledare vars ledningsförmäga är större än ca 10 ~8 S/cm och vars in-tegrerade transmittans är större än 60 % inom spektralomrädet 15 485-675 nm.
18. Ledande polymersammansättning enligt patentkrav 1, varvid nämnda lösningsmedel väljs ur gruppen vilken omfattar alkaner och alkener med ca 5 - ca 12 kolatomer, mineralolja, aromatis- 20 ka föreningar, halogenerade aromatiska föreningar, halogenera-*. de alkaner och alifatiska alkoholer, alkyletrar och ketoner • , med ca 4 - ca 12 kolatomer, cykloalkaner, cykloalkener, kol- tetraklorid, koldisulfid, kloroform, bromoform, diklormetan, morfolin, anilin, alkylbensener, xylen, toluen, dekahydronaf-25 talen, styren, bensylalkohol, naftalen, fenoler, kresoler och akrylater.
• 19. Ledande polymersammansättning enligt patentkrav 1, vars ledningsförmäga är ätminstone 10 S/cm och vilken omfattar po-' ; 30 lyanilin och (L,D)-10-kamfersulfonsyra.
20. Förfarande för framställning av en ledande polymerprodukt av nägon sammansättning enligt patentkrav 1-18, vilket förfarande omfattar följande steg: 113374 a. en lösning framställs vilken omfattar polyanilin, substrat med ledningsförmäga under 10'8 S/cm och dielektrici-tetskonstant under 22, och vilket substrat innehäller sub-stratpolymer och organiskt lösningsmedel i vätskeform; samt 5 funktionaliserad protonsyra löslig i nämnda polymer och nämnda lösningsmedel; och b. nämnda lösningsmedel eller en del därav avlägsnas ur nämnda lösning dä lösningen har bearbetats tili den önskade produkten, eller samtidigt med bearbetningen. 10
21. Förfarande för framställning av en ledande polymerprodukt av nägon sammansättning enligt patentkrav 1-19, vilket förfarande omfattar följande steg: a. en lösning framställs vilken omfattar polyanilin, 15 substrat i vätskeform av organiska, vätskeformade monomerer, vilket substrat har en dielektricitetskonstant under 22, samt funktionaliserad protonsyra löslig i nämnda polymer och nämnda lösningsmedel; och b. monomererna polymeriseras i nämnda lösning efter 20 det lösningen har bearbetats tili den önskade produkten, eller samtidigt med bearbetningen. » 1 · t I
22. Förfarande för framställning av en ledande polymerprodukt ; ur en lösning vilken har en sammansättning enligt patentkrav ><i · :v. 25 1-19, vilket förfarande omfattar följande steg: a. en lösning framställs vilken omfattar polyanilin, ett lösningsmedel vilket har en dielektricitetskonstant under 22, samt funktionaliserad protonsyra kompatibel med bade lös-ningsmedlet och substratpolymerer, samt en eller flere bulk-,1 ; 30 substratpolymerer; och «1·, b. nämnda lösningsmedel avlägsnas helt eller delvis ur nämnda lösning varvid en ledande polymerprodukt uppstär. 113374
23. Förfarande för framställning av en fast, ledande polymer-produkt ur en sammansättning enligt patentkrav 1-19, vilken produkt innehäller en ickeledande substratpolymer och vilket förfarande omfattar följande steg: 5 a. en lösning framställs vilken omfattar pölyäni Iin, organisk, vätskeformad prekursor tili nämnda substratpolymer, upplöst funktionaliserad protonsyra kompatibel med nämnda monomer; och b. monomeren polymeriseras sä en fast produkt upp- 10 star.
24. Förfarande för framställning av en ledande polymerprodukt av nägon sammansättning enligt patentkrav 1-19, ur ledande po-lyanilin och substrat 15 a. genom att framställa en smälta vilken omfattar po- lyanilin och upplöst, funktionaliserad protonsyra noga blandad med smält polymersubstrat vilket väljs ur gruppen termoplas-ter; och b. nämnda smälta tilläts stelna. 20
25. Ljusemitterande diod vilken omfattar en genomskinlig elek-trod vilken omfattar ett material enligt nägot av patentkrav 1-19. a i t I I ·
25 CH3 (CH2)xCH2 (OCH2CH2)nOH, vari x=10-14, n=l,3; x=6, 8, n=l,0; J · .x=10-12, n=3; x=6-8, n=2; poly (oxy-1,2-etandiyl) , a- (nonylfenoxy)-ω-hydroxy och sulfaterat alkylalkoholetoxylatam- ·· moniumsalt. * > I * *
26. Elektriskt ledande produkt vilken omfattar material enligt nägot av patentkrav 1-19, valt ur gruppen fibrer, stänger, a profiler, beläggningar, filmer, behällare, fodral; samt an-• |· vändning därav. [ \ 30
27. Elektriskt ledande produkt vilken omfattar material enligt ·, nägot av patentkrav 1-19, valt ur gruppen lim, bläck, mälfärg, sprayprodukter, oljor, pastor, vaxer; samt användning därav. 113374
28. Flexibel 1jusemitterande diod vilken omfattar en ledande hälinjicerande elektrod vilken omfattar elektriskt ledande material enligt patentkrav 1-19 samt ett elektroluminescent skikt som omfattar flexibel, konjugerad polymer. 5
29. Flexibel 1jusemitterande diod enligt patentkrav 28, vilken ytterligare omfattar en elektroninjicerande kontakt vars ar-betsfunktion är under 4,3.
30. Flexibel 1jusemitterande diod enligt patentkrav 29, vilken ytterligare omfattar ett flexibelt polymerstöd förenat med den ledande, hälinjicerande elektroden. t » * · · t t > iti · * I » t 1 * » · * 1 »
Applications Claiming Priority (8)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US07/714,165 US5232631A (en) | 1991-06-12 | 1991-06-12 | Processible forms of electrically conductive polyaniline |
| US71416591 | 1991-06-12 | ||
| US80055591A | 1991-11-27 | 1991-11-27 | |
| US80055991A | 1991-11-27 | 1991-11-27 | |
| US80055591 | 1991-11-27 | ||
| US80055991 | 1991-11-27 | ||
| US9204167 | 1992-05-19 | ||
| PCT/US1992/004167 WO1992022911A1 (en) | 1991-06-12 | 1992-05-19 | Processible forms of electrically conductive polyaniline and conductive products formed therefrom |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| FI935498A0 FI935498A0 (fi) | 1993-12-08 |
| FI935498A FI935498A (fi) | 1993-12-08 |
| FI113374B true FI113374B (sv) | 2004-04-15 |
Family
ID=27418922
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FI935498A FI113374B (sv) | 1991-06-12 | 1993-12-08 | Processabila former av elledande polyanilin och därav formade ledande produkter |
Country Status (10)
| Country | Link |
|---|---|
| EP (1) | EP0588906B2 (sv) |
| JP (2) | JP3384566B2 (sv) |
| KR (1) | KR100261971B1 (sv) |
| AT (1) | ATE195197T1 (sv) |
| AU (1) | AU669662B2 (sv) |
| CA (1) | CA2111150C (sv) |
| DE (1) | DE69231312T3 (sv) |
| FI (1) | FI113374B (sv) |
| NO (1) | NO308704B1 (sv) |
| WO (1) | WO1992022911A1 (sv) |
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| US5408109A (en) | 1991-02-27 | 1995-04-18 | The Regents Of The University Of California | Visible light emitting diodes fabricated from soluble semiconducting polymers |
| FI101077B (sv) * | 1993-06-04 | 1998-04-15 | Neste Oy | Elledande polymermaterial och förfarande för framställning därav |
| FI98820C (sv) * | 1993-06-04 | 1997-08-25 | Neste Oy | Förfarande för framställning av ett bearbetbart material av ledande polymer |
| NL9301307A (nl) * | 1993-07-26 | 1995-02-16 | Oce Nederland Bv | Electrisch geleidend tonerpoeder voor beeldontwikkeling in electrostatische, elektrofotografische of magnetografische beeldvormingsprocessen. |
| US5783111A (en) * | 1993-09-03 | 1998-07-21 | Uniax Corporation | Electrically conducting compositions |
| CN1046750C (zh) * | 1993-09-03 | 1999-11-24 | 耐斯特欧公司 | 导电组合物 |
| US5520852A (en) * | 1994-06-08 | 1996-05-28 | Neste Oy | Processible electrically conducting polyaniline compositions |
| WO1996004687A1 (fr) * | 1994-08-05 | 1996-02-15 | Hoechst Aktiengesellschaft | Diode electroluminescente organique a jonction p-n |
| NL9402196A (nl) * | 1994-12-23 | 1996-08-01 | Oce Nederland Bv | Werkwijze voor het registreren van beelden, alsmede een beeldvormingsinrichting voor toepassing van de werkwijze. |
| US5804100A (en) * | 1995-01-09 | 1998-09-08 | International Business Machines Corporation | Deaggregated electrically conductive polymers and precursors thereof |
| US5645764A (en) * | 1995-01-19 | 1997-07-08 | International Business Machines Corporation | Electrically conductive pressure sensitive adhesives |
| US5716550A (en) * | 1995-08-10 | 1998-02-10 | Eastman Kodak Company | Electrically conductive composition and elements containing solubilized polyaniline complex and solvent mixture |
| 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 |
| KR970058474A (ko) * | 1995-12-20 | 1997-07-31 | 정몽원 | 전자파 차폐용 케이스 |
| US5798170A (en) * | 1996-02-29 | 1998-08-25 | Uniax Corporation | Long operating life for polymer light-emitting diodes |
| GB2311166A (en) * | 1996-03-13 | 1997-09-17 | Sharp Kk | An optoelectronic semiconductor device |
| US5871671A (en) * | 1997-10-14 | 1999-02-16 | Monsanto Company | Intrinsically conductive polymer/plasticizer blends with enhanced conductivity |
| DE19757542A1 (de) * | 1997-12-23 | 1999-06-24 | Bayer Ag | Siebdruckpaste zur Herstellung elektrisch leitfähiger Beschichtungen |
| GB9816130D0 (en) * | 1998-07-23 | 1998-09-23 | Instance Ltd David J | Display device |
| JP4258583B2 (ja) * | 1999-02-23 | 2009-04-30 | 淳二 城戸 | 電界発光素子 |
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| US6030551A (en) * | 1999-04-07 | 2000-02-29 | Conpoly Technology Co., Ltd. | Polyaniline-containing solution and method for preparing the same |
| GB9907931D0 (en) * | 1999-04-07 | 1999-06-02 | Univ Edinburgh | An optoelectronic display |
| JP3459203B2 (ja) * | 1999-08-06 | 2003-10-20 | 株式会社マルアイ | 導電性インキまたは導電性塗料とその製造方法並びに導電性インキを充填した筆記具 |
| KR100392196B1 (ko) * | 2000-11-23 | 2003-07-23 | (주)해은켐텍 | 전도성 페이스트 |
| EP1451887B1 (de) * | 2001-11-12 | 2015-06-24 | Volkswagen Aktiengesellschaft | Protonenleitende elektrolytmembran, verfahren zu ihrer herstellung und deren verwendung in einer brennstoffzelle |
| US7538165B2 (en) | 2001-12-19 | 2009-05-26 | Nitto Denko Corporation | Conductive polyaniline composition, film thereof and processes for producing these |
| DE10208188B4 (de) * | 2002-02-20 | 2006-05-24 | Amaxa Gmbh | Behälter mit zumindest einer Elektrode |
| US7351359B2 (en) | 2003-10-08 | 2008-04-01 | The Yokohama Rubber Co., Ltd. | Method for producing conductive polyaniline and organic polymer composition |
| WO2005052058A1 (ja) * | 2003-11-28 | 2005-06-09 | Idemitsu Kosan Co., Ltd. | 導電性ポリアニリン組成物、その製造方法及びそれからなる成形体 |
| JP4187764B2 (ja) | 2004-03-31 | 2008-11-26 | 横浜ゴム株式会社 | 光電変換素子及びそれを用いた色素増感太陽電池 |
| GB2418064A (en) * | 2004-09-09 | 2006-03-15 | Stephen Harvey | Vehicle brake and hazard lights |
| EP1884354A4 (en) * | 2005-05-27 | 2008-08-06 | Idemitsu Kosan Co | MULTILAYER BODY OF A CONDUCTIVE POLYMER |
| JP4485420B2 (ja) * | 2005-06-22 | 2010-06-23 | 日東電工株式会社 | 結晶薄膜を製造する方法 |
| JP5492413B2 (ja) * | 2006-08-10 | 2014-05-14 | 出光興産株式会社 | 導電性ポリアニリン組成物及びその製造方法 |
| JP5303107B2 (ja) * | 2006-09-25 | 2013-10-02 | 出光興産株式会社 | 導電性ポリアニリン複合体の製造方法 |
| US20080299293A1 (en) * | 2007-05-02 | 2008-12-04 | Plextronics, Inc. | Solvent system for conjugated polymers |
| JPWO2009084418A1 (ja) * | 2007-12-27 | 2011-05-19 | 出光興産株式会社 | ポリアニリン複合体、その組成物及び成形体 |
| WO2009084419A1 (ja) * | 2007-12-27 | 2009-07-09 | Idemitsu Kosan Co., Ltd. | ポリアニリン複合体、その組成物及び成形体 |
| WO2010072646A1 (en) | 2008-12-23 | 2010-07-01 | Oce-Technologies B.V. | Method for operating an image-forming device and an image forming device for application of the method |
| KR101807325B1 (ko) * | 2009-09-07 | 2017-12-08 | 이데미쓰 고산 가부시키가이샤 | 도전성 조성물 |
| US9384866B2 (en) | 2011-01-27 | 2016-07-05 | Idemitsu Kosan Co., Ltd. | Polyaniline composite, method for producing same, and composition |
| US9496502B2 (en) * | 2011-05-12 | 2016-11-15 | Merck Patent Gmbh | Organic ionic compounds, compositions and electronic devices |
| JP5955786B2 (ja) | 2013-01-07 | 2016-07-20 | 出光興産株式会社 | 導電性高分子組成物 |
| WO2016006251A1 (ja) | 2014-07-11 | 2016-01-14 | 出光興産株式会社 | ポリアニリン複合体組成物の製造方法及びポリアニリン複合体組成物 |
| US11767399B2 (en) | 2018-05-08 | 2023-09-26 | Idemitsu Kosan Co., Ltd. | Composition, method for producing conductive film, conductive film, capacitor |
| CN114293277A (zh) * | 2022-01-14 | 2022-04-08 | 中国纺织科学研究院有限公司 | 导电聚乙烯纤维及其制备方法 |
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| JPH0788424B2 (ja) * | 1987-07-24 | 1995-09-27 | 株式会社小松製作所 | フィルム状導電性高分子の製造方法 |
| US5160457A (en) * | 1987-08-07 | 1992-11-03 | Allied-Signal Inc. | Thermally stable forms of electrically conductive polyaniline |
| US5069820A (en) * | 1987-08-07 | 1991-12-03 | Allied-Signal Inc. | Thermally stable forms of electrically conductive polyaniline |
| DE3729566A1 (de) * | 1987-09-04 | 1989-03-16 | Zipperling Kessler & Co | Intrinsisch leitfaehiges polymer in form eines dispergierbaren feststoffes, dessen herstellung und dessen verwendung |
| US4851487A (en) * | 1988-02-22 | 1989-07-25 | Lockheed Corporation | Conductive polymer materials and method of producing same |
| US4935163A (en) * | 1988-08-01 | 1990-06-19 | Lockheed Corporation | High service temperature conductive polymers and method of producing same |
| JP2868564B2 (ja) * | 1989-03-13 | 1999-03-10 | 日立マクセル株式会社 | 磁気記録媒体 |
| JPH02240163A (ja) * | 1989-03-14 | 1990-09-25 | Tomoegawa Paper Co Ltd | 高分子導電性溶液 |
| WO1990013601A1 (en) * | 1989-05-12 | 1990-11-15 | Lockheed Corporation | Conductive polymer-polyamide blends and method of producing same |
| US5093439A (en) * | 1989-10-19 | 1992-03-03 | Ohio State University Research Foundation | Processes for preparation of sulfonated polyaniline compositions and uses thereof |
| US5008041A (en) * | 1990-01-30 | 1991-04-16 | Lockheed Corporation | Preparation of conductive polyaniline having controlled molecular weight |
| US5278213A (en) * | 1991-04-22 | 1994-01-11 | Allied Signal Inc. | Method of processing neutral polyanilines in solvent and solvent mixtures |
-
1992
- 1992-05-19 AU AU20166/92A patent/AU669662B2/en not_active Expired
- 1992-05-19 KR KR1019930703839A patent/KR100261971B1/ko not_active IP Right Cessation
- 1992-05-19 CA CA002111150A patent/CA2111150C/en not_active Expired - Lifetime
- 1992-05-19 AT AT92912738T patent/ATE195197T1/de active
- 1992-05-19 JP JP50085993A patent/JP3384566B2/ja not_active Expired - Lifetime
- 1992-05-19 WO PCT/US1992/004167 patent/WO1992022911A1/en active IP Right Grant
- 1992-05-19 EP EP92912738A patent/EP0588906B2/en not_active Expired - Lifetime
- 1992-05-19 DE DE69231312T patent/DE69231312T3/de not_active Expired - Lifetime
-
1993
- 1993-12-08 FI FI935498A patent/FI113374B/sv not_active IP Right Cessation
- 1993-12-09 NO NO934517A patent/NO308704B1/no not_active IP Right Cessation
-
2002
- 2002-09-11 JP JP2002265945A patent/JP2003176409A/ja not_active Withdrawn
Also Published As
| Publication number | Publication date |
|---|---|
| WO1992022911A1 (en) | 1992-12-23 |
| JP3384566B2 (ja) | 2003-03-10 |
| AU669662B2 (en) | 1996-06-20 |
| CA2111150A1 (en) | 1992-12-23 |
| NO934517D0 (no) | 1993-12-09 |
| JP2003176409A (ja) | 2003-06-24 |
| DE69231312D1 (de) | 2000-09-07 |
| EP0588906B2 (en) | 2003-06-18 |
| EP0588906A1 (en) | 1994-03-30 |
| DE69231312T2 (de) | 2000-12-28 |
| CA2111150C (en) | 2001-10-30 |
| EP0588906A4 (en) | 1994-08-24 |
| AU2016692A (en) | 1993-01-12 |
| JPH06508390A (ja) | 1994-09-22 |
| NO308704B1 (no) | 2000-10-16 |
| FI935498A0 (fi) | 1993-12-08 |
| ATE195197T1 (de) | 2000-08-15 |
| KR100261971B1 (ko) | 2000-07-15 |
| DE69231312T3 (de) | 2003-12-11 |
| FI935498A (fi) | 1993-12-08 |
| EP0588906B1 (en) | 2000-08-02 |
| NO934517L (no) | 1994-01-31 |
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