JP2013532769A - 水溶性ポリマー材料の加工方法 - Google Patents
水溶性ポリマー材料の加工方法 Download PDFInfo
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- JP2013532769A JP2013532769A JP2013523273A JP2013523273A JP2013532769A JP 2013532769 A JP2013532769 A JP 2013532769A JP 2013523273 A JP2013523273 A JP 2013523273A JP 2013523273 A JP2013523273 A JP 2013523273A JP 2013532769 A JP2013532769 A JP 2013532769A
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- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
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- KTWOOEGAPBSYNW-UHFFFAOYSA-N ferrocene Chemical compound [Fe+2].C=1C=C[CH-]C=1.C=1C=C[CH-]C=1 KTWOOEGAPBSYNW-UHFFFAOYSA-N 0.000 description 1
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- WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 description 1
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- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
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- 125000004437 phosphorous atom Chemical group 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 229920001467 poly(styrenesulfonates) Polymers 0.000 description 1
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- 125000003367 polycyclic group Chemical group 0.000 description 1
- 239000011970 polystyrene sulfonate Substances 0.000 description 1
- 229960002796 polystyrene sulfonate Drugs 0.000 description 1
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
- CASUWPDYGGAUQV-UHFFFAOYSA-M potassium;methanol;hydroxide Chemical compound [OH-].[K+].OC CASUWPDYGGAUQV-UHFFFAOYSA-M 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
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- 235000019260 propionic acid Nutrition 0.000 description 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 1
- 150000003233 pyrroles Chemical class 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 150000005839 radical cations Chemical class 0.000 description 1
- 229920005604 random copolymer Polymers 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- SBIBMFFZSBJNJF-UHFFFAOYSA-N selenium;zinc Chemical compound [Se]=[Zn] SBIBMFFZSBJNJF-UHFFFAOYSA-N 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 150000003384 small molecules Chemical class 0.000 description 1
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- 238000009718 spray deposition Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 229920001897 terpolymer Polymers 0.000 description 1
- 229920006029 tetra-polymer Polymers 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 238000005809 transesterification reaction Methods 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003624 transition metals Chemical class 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 description 1
- LWIHDJKSTIGBAC-UHFFFAOYSA-K tripotassium phosphate Chemical compound [K+].[K+].[K+].[O-]P([O-])([O-])=O LWIHDJKSTIGBAC-UHFFFAOYSA-K 0.000 description 1
- 238000001429 visible spectrum Methods 0.000 description 1
- 239000003021 water soluble solvent Substances 0.000 description 1
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- 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
- H01B1/122—Ionic conductors
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- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01G—CAPACITORS; CAPACITORS, RECTIFIERS, DETECTORS, SWITCHING DEVICES, LIGHT-SENSITIVE OR TEMPERATURE-SENSITIVE DEVICES OF THE ELECTROLYTIC TYPE
- H01G9/00—Electrolytic capacitors, rectifiers, detectors, switching devices, light-sensitive or temperature-sensitive devices; Processes of their manufacture
- H01G9/004—Details
- H01G9/022—Electrolytes; Absorbents
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- C—CHEMISTRY; METALLURGY
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- C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G2261/30—Monomer units or repeat units incorporating structural elements in the main chain
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- C08G2261/322—Monomer units or repeat units incorporating structural elements in the main chain incorporating heteroaromatic structural elements in the main chain non-condensed
- C08G2261/3223—Monomer units or repeat units incorporating structural elements in the main chain incorporating heteroaromatic structural elements in the main chain non-condensed containing one or more sulfur atoms as the only heteroatom, e.g. thiophene
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Abstract
【選択図】なし
Description
本願は、2010年8月2日に出願された米国仮出願第61/369,821号の利益を主張するものであり、すべての図、表および図面を含む当該出願の開示内容は、出典明示によりすべて本明細書に組み入れられる。
水溶性のイオン性CPの形態を有する酸塩に変換できる。イオン性CPは、水溶液から該イオン性CPを堆積させた後で不溶性CPに変換できる。アニオン性CP系の典型的なカルボン酸塩について先に説明したように、不溶化CPへの変換は酸性化により行うことができる。本発明の別の態様では、アニオン性CPの対イオンは交換するに際し、1価のカチオンを2価カチオンまたは多価カチオンと交換することにより、あるいはカチオン性オリゴマーまたはポリマー等の2価カチオン種または多価カチオン種と交換することにより、可溶性CPをイオン性の“架橋”を有する不溶性CPに変えることもできる。例えば、アルカリ金属対イオンを有するイオン性CPの膜をカルシウムトリフラート溶液に浸漬してアルカリイオンをカルシウムと置換することにより、イオン性CPを、イオン性官能基を側鎖に有する不溶性CPへと変換することができる。イオン性CPをイオン性の不溶性CPへ変換するために、2価カチオンまたは多価カチオンあるいは2価カチオン種または多価カチオン種の水溶液または非水溶液、例えばカルシウムトリフラートのメタノール溶液を用いることができる。
すべての試薬および出発材料は、市販元から購入し、特に断らない限りそのまま用いた。ITO電極は、デルタテクノロジー社から購入した(7×50×0.7mm、シート抵抗 Rs 8−12Ω/sq)。
1H NMR(300MHz,CDCl3):δ=6.61(s,2H),4.02(s,4H),2.74(s,4H)。
13CNMR(75MHz,CDCl3):δ=148.64,115.4,107.49,75.0,43.1,21.25。
C11H10O2N2SのHRMS 計算値 235.0536;分析値 235.0552。C11H10O2N2Sの計算値:C 56.39;H 4.3;N 11.96;S 13.69,分析値:C 56.39;H 4.3;N 11.93;S 13.53。
1H NMR(300MHz,CDCl3):δ=12.3(s,2H),6.74(s,2H),4.0(s,4H),2.5(s,4H)。
13CNMR(75MHz,CDCl3):δ=172.9,150.1,106.7,76.6,42.9,35.8。
C11H12O6SのHRMS 計算値 273.0427;分析値 273.0427。
C11H12O6Sの計算値:C 48.52;H 4.44;S 11.78,分析値:C 48.62;H 4.37;S 11.07。
1H NMR(300MHz,CDCl3):δ=6.45(s,2H),4.1(s,4H),4.06(t,4H),2.68(s,4H),1.61(t,4H),1.26(m,36H)。
13CNMR(75MHz,CDCl3):δ=171.16,149.5,105.43,76.43,65.07,43.36,36.38,32.14,29.88,29.85,29.81,29.75,29.58,29.48,28.76,26.15,22.91,14.34。
C35H60O6SのHRMS 計算値 609.4144;分析値 609.4170。
C35H60O6Sの計算値:C 69.04;H 9.93;S 5.27;分析値 C 69.47;H 10.06;S 5.10。
1H NMR(300MHz,CDCl3):δ=4.23(bs,4H),4.09(bs,4H),2.81(bs,4H),1.61(bs,4H),1.25(bs,36H),0.87(bs,6H)。
GPC分析:Mn=39.5kDa、Mw=84.9kDa、PDI=2.15。
C11H8K206Sの元素分析計算値:C 38.14,H 2.33;分析値 C 37.63,H 3.34。
Claims (26)
- 水溶性電解質によって膨潤および/または水溶性電解質に接触するとともに、有機溶媒を実質的に含まない不溶性CPを含むπ共役ポリマー(CP)膜であって、塩基ではなく酸の添加によって、あるいは酸ではなく塩基の添加によって膜が溶解可能である、該π共役ポリマー膜。
- 前記CPが酸性官能基を含む少なくとも1つの側鎖を有する繰り返し単位を有し、前記の膜が塩基の存在下で溶解する請求項1記載のCP膜。
- 前記酸性官能基が、カルボン酸、チオカルボン酸、ジチオカルボン酸、スルホン酸、リン酸、ホウ酸またはそれらの組み合わせである請求項2記載のCP膜。
- 前記CPが塩基性官能基を含む少なくとも1種の側鎖を有する繰り返し単位を有し、前記の膜が酸の存在下で溶解する請求項1記載のCP膜。
- 前記の塩基単位が、アミン、イミン、ホスフィン、チオールまたはチオエーテルである請求項4記載のCP膜。
- 水溶性のイオン性CPの懸濁液または溶液を用意し、
該水溶性のイオン性CPの懸濁液または溶液を表面上に堆積させてイオン性CPの膜を形成し、および
該イオン性CP膜を不溶性CP膜に変換する、不溶性π共役ポリマー(CP)膜の形成方法。 - 前駆体CPの有機溶媒懸濁液または有機溶媒溶液を用意し、および
該前駆体CPの有機溶媒懸濁液または有機溶媒溶液をイオン性CPの懸濁液または溶液に転換することをさらに含む請求項6記載の方法。 - 前記の前駆体CPの懸濁液または溶液の前駆体CPが、カルボン酸、チオカルボン酸、ジチオカルボン酸、スルホン酸、リン酸、またはホウ酸のエステルを含む少なくとも1つの側鎖を有する繰り返し単位を含む請求項7記載の方法。
- 前記エステルがアルキル置換カルボン酸エステルである請求項8記載の方法。
- 前記の転換が、1当量またはそれより多い当量の塩基を用いて前記エステルを加水分解すること、あるいは前記酸エステルの加水分解および続いて1当量またはそれより多い当量の塩基を添加して酸の塩を生成させることを含む請求項8記載の方法。
- 前記塩基が、アルカリ金属またはテトラアルキルアンモニウムの水酸化物である請求項10記載の方法。
- 前記の変換が、酸との反応を含む請求項11記載の方法。
- 前記の水酸化物がテトラアルキルアンモニウムの水酸化物であり、前記の変換が、テトラアルキルアンモニウムの熱劣化を含む請求項11記載の方法。
- 前記の変換が、アルカリ金属カチオンまたはテトラアルキルアンモニウムカチオンと、二価カチオンまたは多価カチオンとの交換を含む請求項11記載の方法。
- 前記前駆体CPが、アミン、イミン、ホスフィンまたはチオエーテルを含む少なくとも1つの側鎖を有する繰り返し単位を含む請求項7記載の方法。
- 前記の変換が、酸によるプロトン化を含む請求項15記載の方法。
- 前記の変換が、塩基の添加を含む請求項16記載の方法。
- 前記の転換が、求電子性炭素との反応を含む請求項15記載の方法。
- 前記求電子性炭素が、アルキル化剤の求電子性炭素である請求項18記載の方法。
- 前記の変換が、熱劣化を含む請求項18記載の方法。
- 前記の変換が、求核性試薬との反応を含む請求項18記載の方法。
- 前記前駆体CPが、二座配位子または多座配位子を含む少なくとも1つの側鎖を有する繰り返し単位を含む請求項7記載の方法。
- 前記の転換が、金属塩との反応を含む請求項22記載の方法。
- 前記の変換が、前記の二座配位子または多座配位子から第2の二座配位子または多座配位子へと金属塩を交換することを含む請求項23記載の方法。
- 前記の膜形成が、水溶性のイオン性CP溶液を印刷または噴霧することを含む請求項6記載の方法。
- 水溶性電解質によって膨潤および/または水溶性電解質に接触するとともに、有機溶媒を実質的に含まない不溶性CPを含むデバイスであって、
前記不溶性CPの膜が、塩基ではなく酸の添加によって、あるいは酸ではなく塩基の添加によって膜が溶解可能であり、および
前記不溶性CPが、カルボン酸、スルホン酸、リン酸、ホウ酸、アミン、イミン、ホスフィン、チオエーテル、あるいは配位していない二座配位子または多座配位子を有する複数の繰り返し単位を含む、該デバイス。
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EP2601248A2 (en) | 2013-06-12 |
WO2012018815A2 (en) | 2012-02-09 |
WO2012018815A3 (en) | 2012-05-10 |
CN103052673A (zh) | 2013-04-17 |
RU2013101994A (ru) | 2014-09-10 |
BR112013002602A2 (pt) | 2016-06-07 |
US9093193B2 (en) | 2015-07-28 |
CA2805638A1 (en) | 2012-02-09 |
US20120032104A1 (en) | 2012-02-09 |
WO2012018815A9 (en) | 2013-09-19 |
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