JP2008546899A5 - - Google Patents
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- JP2008546899A5 JP2008546899A5 JP2008519492A JP2008519492A JP2008546899A5 JP 2008546899 A5 JP2008546899 A5 JP 2008546899A5 JP 2008519492 A JP2008519492 A JP 2008519492A JP 2008519492 A JP2008519492 A JP 2008519492A JP 2008546899 A5 JP2008546899 A5 JP 2008546899A5
- Authority
- JP
- Japan
- Prior art keywords
- fluorinated
- polymer
- wetted
- organic solvent
- acid
- 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.)
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- 229920000642 polymer Polymers 0.000 claims description 43
- 239000000203 mixture Substances 0.000 claims description 31
- 239000003960 organic solvent Substances 0.000 claims description 29
- 239000002253 acid Substances 0.000 claims description 28
- 229920001940 conductive polymer Polymers 0.000 claims description 13
- 239000000178 monomer Substances 0.000 claims description 12
- 239000006185 dispersion Substances 0.000 claims description 9
- 238000000034 method Methods 0.000 claims description 8
- 150000003460 sulfonic acids Chemical class 0.000 claims description 6
- 239000002243 precursor Substances 0.000 claims description 5
- 239000007800 oxidant agent Substances 0.000 claims description 4
- 239000011541 reaction mixture Substances 0.000 claims description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 21
- -1 cyano, hydroxyl Chemical group 0.000 description 21
- 125000000217 alkyl group Chemical group 0.000 description 18
- 125000003118 aryl group Chemical group 0.000 description 14
- RZXLPPRPEOUENN-UHFFFAOYSA-N Chlorfenson Chemical compound C1=CC(Cl)=CC=C1OS(=O)(=O)C1=CC=C(Cl)C=C1 RZXLPPRPEOUENN-UHFFFAOYSA-N 0.000 description 12
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 10
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- 229920001577 copolymer Polymers 0.000 description 8
- 229910052739 hydrogen Inorganic materials 0.000 description 8
- 239000001257 hydrogen Substances 0.000 description 8
- 125000003342 alkenyl group Chemical group 0.000 description 7
- 125000002947 alkylene group Chemical group 0.000 description 7
- 150000002431 hydrogen Chemical class 0.000 description 7
- 239000004593 Epoxy Substances 0.000 description 6
- ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical compound OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 description 6
- 125000003545 alkoxy group Chemical group 0.000 description 6
- 125000002877 alkyl aryl group Chemical group 0.000 description 6
- 125000006350 alkyl thio alkyl group Chemical group 0.000 description 6
- 125000003710 aryl alkyl group Chemical group 0.000 description 6
- 125000001589 carboacyl group Chemical group 0.000 description 6
- 150000007942 carboxylates Chemical class 0.000 description 6
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 6
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 5
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 5
- 125000004450 alkenylene group Chemical group 0.000 description 5
- 125000004183 alkoxy alkyl group Chemical group 0.000 description 5
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 5
- 125000003282 alkyl amino group Chemical group 0.000 description 5
- 125000004644 alkyl sulfinyl group Chemical group 0.000 description 5
- 125000004390 alkyl sulfonyl group Chemical group 0.000 description 5
- 125000004414 alkyl thio group Chemical group 0.000 description 5
- 125000005135 aryl sulfinyl group Chemical group 0.000 description 5
- 125000004391 aryl sulfonyl group Chemical group 0.000 description 5
- 125000005110 aryl thio group Chemical group 0.000 description 5
- 125000004104 aryloxy group Chemical group 0.000 description 5
- 125000004663 dialkyl amino group Chemical group 0.000 description 5
- 229910052736 halogen Inorganic materials 0.000 description 5
- 150000002367 halogens Chemical class 0.000 description 5
- ZAHSNWXGKUBLHM-UHFFFAOYSA-N hydroperoxy(hydroxy)silane Chemical compound OO[SiH2]O ZAHSNWXGKUBLHM-UHFFFAOYSA-N 0.000 description 5
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 5
- 229920000767 polyaniline Polymers 0.000 description 5
- 229920000128 polypyrrole Polymers 0.000 description 5
- 229910000077 silane Inorganic materials 0.000 description 5
- 229910052717 sulfur Inorganic materials 0.000 description 5
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 4
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 4
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 4
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 4
- 125000003709 fluoroalkyl group Chemical group 0.000 description 4
- 125000004474 heteroalkylene group Chemical group 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 229920000123 polythiophene Polymers 0.000 description 4
- 125000004963 sulfonylalkyl group Chemical group 0.000 description 4
- 239000011593 sulfur Substances 0.000 description 4
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 125000002723 alicyclic group Chemical group 0.000 description 3
- 125000000732 arylene group Chemical group 0.000 description 3
- 125000005549 heteroarylene group Chemical group 0.000 description 3
- 125000004430 oxygen atom Chemical group O* 0.000 description 3
- BQCIDUSAKPWEOX-UHFFFAOYSA-N 1,1-Difluoroethene Chemical group FC(F)=C BQCIDUSAKPWEOX-UHFFFAOYSA-N 0.000 description 2
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 2
- 239000005977 Ethylene Substances 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- YHBTXTFFTYXOFV-UHFFFAOYSA-N Liquid thiophthene Chemical compound C1=CSC2=C1C=CS2 YHBTXTFFTYXOFV-UHFFFAOYSA-N 0.000 description 2
- 229920001609 Poly(3,4-ethylenedioxythiophene) Polymers 0.000 description 2
- 239000004952 Polyamide Substances 0.000 description 2
- 239000004642 Polyimide Substances 0.000 description 2
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 150000001336 alkenes Chemical class 0.000 description 2
- 125000005336 allyloxy group Chemical group 0.000 description 2
- 229920003235 aromatic polyamide Polymers 0.000 description 2
- JHRWWRDRBPCWTF-OLQVQODUSA-N captafol Chemical group C1C=CC[C@H]2C(=O)N(SC(Cl)(Cl)C(Cl)Cl)C(=O)[C@H]21 JHRWWRDRBPCWTF-OLQVQODUSA-N 0.000 description 2
- 125000002843 carboxylic acid group Chemical group 0.000 description 2
- 125000004093 cyano group Chemical group *C#N 0.000 description 2
- 229920002313 fluoropolymer Polymers 0.000 description 2
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 2
- 229920002401 polyacrylamide Polymers 0.000 description 2
- 229920000058 polyacrylate Polymers 0.000 description 2
- 229920002647 polyamide Polymers 0.000 description 2
- 229920001721 polyimide Polymers 0.000 description 2
- 229920000193 polymethacrylate Polymers 0.000 description 2
- 229920000098 polyolefin Polymers 0.000 description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
- 125000000542 sulfonic acid group Chemical group 0.000 description 2
- PFZLGKHSYILJTH-UHFFFAOYSA-N thieno[2,3-c]thiophene Chemical compound S1C=C2SC=CC2=C1 PFZLGKHSYILJTH-UHFFFAOYSA-N 0.000 description 2
- NMFKEMBATXKZSP-UHFFFAOYSA-N thieno[3,2-b]thiophene Chemical compound S1C=CC2=C1C=CS2.S1C=CC2=C1C=CS2 NMFKEMBATXKZSP-UHFFFAOYSA-N 0.000 description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 2
- 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 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- LTEQMZWBSYACLV-UHFFFAOYSA-N Hexylbenzene Chemical compound CCCCCCC1=CC=CC=C1 LTEQMZWBSYACLV-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 1
- 125000003368 amide group Chemical group 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 125000000392 cycloalkenyl group Chemical group 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- 125000001033 ether group Chemical group 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 125000004404 heteroalkyl group Chemical group 0.000 description 1
- 239000003456 ion exchange resin Substances 0.000 description 1
- 229920003303 ion-exchange polymer Polymers 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052711 selenium Inorganic materials 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 150000003673 urethanes Chemical class 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US69427705P | 2005-06-27 | 2005-06-27 | |
| US60/694,277 | 2005-06-27 | ||
| PCT/US2006/025013 WO2007002682A2 (en) | 2005-06-27 | 2006-06-27 | Electrically conductive polymer compositions |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2008546899A JP2008546899A (ja) | 2008-12-25 |
| JP2008546899A5 true JP2008546899A5 (https=) | 2009-08-13 |
| JP5323478B2 JP5323478B2 (ja) | 2013-10-23 |
Family
ID=37595984
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2008519492A Expired - Fee Related JP5323478B2 (ja) | 2005-06-27 | 2006-06-27 | 導電性ポリマー組成物 |
Country Status (5)
| Country | Link |
|---|---|
| US (2) | US7837901B2 (https=) |
| EP (1) | EP1899985A4 (https=) |
| JP (1) | JP5323478B2 (https=) |
| KR (1) | KR101294892B1 (https=) |
| WO (1) | WO2007002682A2 (https=) |
Families Citing this family (63)
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| CA2499364A1 (en) | 2002-09-24 | 2004-04-08 | E. I. Du Pont De Nemours And Company | Water dispersible polyanilines made with polymeric acid colloids for electronics applications |
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| JP4464277B2 (ja) | 2002-09-24 | 2010-05-19 | イー・アイ・デュポン・ドウ・ヌムール・アンド・カンパニー | 導電性有機ポリマー／ナノ粒子複合材料およびその使用方法 |
| AU2003275203A1 (en) * | 2002-09-24 | 2004-04-19 | E.I. Du Pont De Nemours And Company | Water dispersible polythiophenes made with polymeric acid colloids |
| US7390438B2 (en) | 2003-04-22 | 2008-06-24 | E.I. Du Pont De Nemours And Company | Water dispersible substituted polydioxythiophenes made with fluorinated polymeric sulfonic acid colloids |
| US7351358B2 (en) | 2004-03-17 | 2008-04-01 | E.I. Du Pont De Nemours And Company | Water dispersible polypyrroles made with polymeric acid colloids for electronics applications |
| US8147962B2 (en) | 2004-04-13 | 2012-04-03 | E. I. Du Pont De Nemours And Company | Conductive polymer composites |
| US7638072B2 (en) * | 2005-06-27 | 2009-12-29 | E. I. Du Pont De Nemours And Company | Electrically conductive polymer compositions |
| KR101356296B1 (ko) * | 2005-06-28 | 2014-02-06 | 이 아이 듀폰 디 네모아 앤드 캄파니 | 높은 일 함수의 투명한 도체 |
| WO2007002740A2 (en) | 2005-06-28 | 2007-01-04 | E. I. Du Pont De Nemours And Company | Buffer compositions |
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| US7354532B2 (en) * | 2004-04-13 | 2008-04-08 | E.I. Du Pont De Nemours And Company | Compositions of electrically conductive polymers and non-polymeric fluorinated organic acids |
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-
2006
- 2006-06-27 EP EP06785660A patent/EP1899985A4/en not_active Withdrawn
- 2006-06-27 JP JP2008519492A patent/JP5323478B2/ja not_active Expired - Fee Related
- 2006-06-27 WO PCT/US2006/025013 patent/WO2007002682A2/en not_active Ceased
- 2006-06-27 KR KR1020087002163A patent/KR101294892B1/ko not_active Expired - Fee Related
- 2006-06-27 US US11/475,715 patent/US7837901B2/en active Active
-
2010
- 2010-10-15 US US12/905,673 patent/US8568616B2/en active Active
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