JP2016535135A - Pedot−電解質(コ)ポリマーの合成方法 - Google Patents
Pedot−電解質(コ)ポリマーの合成方法 Download PDFInfo
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- 229920001577 copolymer Polymers 0.000 title claims abstract description 18
- 239000003792 electrolyte Substances 0.000 title claims abstract description 17
- 238000000034 method Methods 0.000 title claims abstract description 17
- 230000002194 synthesizing effect Effects 0.000 title abstract description 3
- 229920001609 Poly(3,4-ethylenedioxythiophene) Polymers 0.000 claims abstract description 10
- 239000004816 latex Substances 0.000 claims description 18
- 229920000126 latex Polymers 0.000 claims description 18
- GKWLILHTTGWKLQ-UHFFFAOYSA-N 2,3-dihydrothieno[3,4-b][1,4]dioxine Chemical compound O1CCOC2=CSC=C21 GKWLILHTTGWKLQ-UHFFFAOYSA-N 0.000 claims description 16
- 239000000178 monomer Substances 0.000 claims description 14
- 238000006243 chemical reaction Methods 0.000 claims description 13
- 239000003999 initiator Substances 0.000 claims description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 9
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims description 8
- ROOXNKNUYICQNP-UHFFFAOYSA-N ammonium persulfate Chemical group [NH4+].[NH4+].[O-]S(=O)(=O)OOS([O-])(=O)=O ROOXNKNUYICQNP-UHFFFAOYSA-N 0.000 claims description 8
- 230000015572 biosynthetic process Effects 0.000 claims description 8
- 238000003756 stirring Methods 0.000 claims description 8
- 238000003786 synthesis reaction Methods 0.000 claims description 7
- 239000006185 dispersion Substances 0.000 claims description 6
- 238000010438 heat treatment Methods 0.000 claims description 6
- AGBXYHCHUYARJY-UHFFFAOYSA-N 2-phenylethenesulfonic acid Chemical compound OS(=O)(=O)C=CC1=CC=CC=C1 AGBXYHCHUYARJY-UHFFFAOYSA-N 0.000 claims description 5
- 229910001870 ammonium persulfate Inorganic materials 0.000 claims description 4
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 3
- 230000005693 optoelectronics Effects 0.000 claims description 3
- 239000002904 solvent Substances 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 239000002041 carbon nanotube Substances 0.000 claims description 2
- 229910021393 carbon nanotube Inorganic materials 0.000 claims description 2
- JRKICGRDRMAZLK-UHFFFAOYSA-L persulfate group Chemical group S(=O)(=O)([O-])OOS(=O)(=O)[O-] JRKICGRDRMAZLK-UHFFFAOYSA-L 0.000 claims description 2
- 239000002109 single walled nanotube Substances 0.000 claims description 2
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims 1
- 150000003839 salts Chemical class 0.000 claims 1
- 239000002131 composite material Substances 0.000 abstract description 10
- 238000006116 polymerization reaction Methods 0.000 description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 5
- 239000002245 particle Substances 0.000 description 5
- 229920000642 polymer Polymers 0.000 description 5
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- 210000003739 neck Anatomy 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 238000002296 dynamic light scattering Methods 0.000 description 3
- 229920000867 polyelectrolyte Polymers 0.000 description 3
- 239000002243 precursor Substances 0.000 description 3
- 239000000654 additive Substances 0.000 description 2
- 239000007810 chemical reaction solvent Substances 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 239000012467 final product Substances 0.000 description 2
- 125000000524 functional group Chemical group 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 229920001467 poly(styrenesulfonates) Polymers 0.000 description 2
- 229960002796 polystyrene sulfonate Drugs 0.000 description 2
- 239000011970 polystyrene sulfonate Substances 0.000 description 2
- 159000000000 sodium salts Chemical group 0.000 description 2
- 125000003011 styrenyl group Chemical group [H]\C(*)=C(/[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 2
- 239000004094 surface-active agent Substances 0.000 description 2
- 241001479434 Agfa Species 0.000 description 1
- XMWRBQBLMFGWIX-UHFFFAOYSA-N C60 fullerene Chemical compound C12=C3C(C4=C56)=C7C8=C5C5=C9C%10=C6C6=C4C1=C1C4=C6C6=C%10C%10=C9C9=C%11C5=C8C5=C8C7=C3C3=C7C2=C1C1=C2C4=C6C4=C%10C6=C9C9=C%11C5=C5C8=C3C3=C7C1=C1C2=C4C6=C2C9=C5C3=C12 XMWRBQBLMFGWIX-UHFFFAOYSA-N 0.000 description 1
- 238000003917 TEM image Methods 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- 238000000089 atomic force micrograph Methods 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 239000008367 deionised water Substances 0.000 description 1
- 229910021641 deionized water Inorganic materials 0.000 description 1
- 229910001873 dinitrogen Inorganic materials 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 229910003472 fullerene Inorganic materials 0.000 description 1
- 229910021389 graphene Inorganic materials 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000002048 multi walled nanotube Substances 0.000 description 1
- 238000010899 nucleation Methods 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 230000037361 pathway Effects 0.000 description 1
- 230000035699 permeability Effects 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
- 239000002994 raw material Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000000523 sample Substances 0.000 description 1
- 239000012798 spherical particle Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 150000003440 styrenes Chemical class 0.000 description 1
- 125000005463 sulfonylimide group Chemical group 0.000 description 1
- 238000004627 transmission electron microscopy Methods 0.000 description 1
- 238000000108 ultra-filtration Methods 0.000 description 1
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Abstract
Description
− 反応容器内で15℃から25℃の間の温度で攪拌しながら、水とイオン性モノマーとの溶液を調製し、
− 溶媒に予め溶解させたEDOT溶液を導入し、
− 溶解するまで攪拌し、
− 溶媒−非イオン性モノマー分散液を導入し、
− 得られた分散液が白くなるまで攪拌し、
− 35℃から55℃の間の温度に加熱し、
− 開始剤と残りのEDOTとの溶液を導入し、
− 残りのEDOTと開始剤との溶液の連続的または半連続的な導入と並行して、攪拌及び加熱を継続する。
PEDOT-ポリスチレン−コ−ポリスチレンスルホネートラテックスの合成:
重合反応容器は、その系を加熱/冷却するための熱交換流体の循環用のジャケット、溶媒の温度を測定するためのプローブ導入用のネック、重合反応を抑制する傾向にある酸素を流し出すための窒素ガス導入用のネック、可変速度で回転させるためモーターに接続されたスターラー、添加剤を添加するための2つのネック、及び凝縮/還流系に接続されたネックを備えている。
a)0.2ml(すなわち266mg=1モル/当量)のEDOTと6.6mlのイソプロパノールから作製される溶液;
b)超音波浴を使用する、3.4mlのイソプロパノール中、0.15ml(すなわち137.2mg=0.6モル/当量)のスチレン(St)の分散液;
c)26.4mlの脱塩水(濃度0.04g/ml)中、1.057g(すなわち、EDOTに対して2.3モル/当量、及びSt+SSに対して0.1モル/当量)の過硫酸アンモニウムの溶液。
実施例1で調製されたPEDOT-ポリスチレン−コ−ポリスチレンスルホネートラテックスを市販のラテックス(Clevios社製のPH1000)と比較する。
Claims (13)
- PEDOTと電解質(コ)ポリマーとの同時合成のための方法であって、次の連続工程:
− 反応容器内で15℃から25℃の間の温度で攪拌しながら、水とイオン性モノマーとの溶液を調製する工程、
− 溶媒に予め溶解させたEDOT溶液を導入する工程、
− 溶解するまで攪拌する工程、
− 溶媒−非イオン性モノマー分散液を導入する工程、
− 得られた分散液が白くなるまで攪拌する工程、
− 35℃から55℃の間の温度に加熱する工程、
− 開始剤と残りのEDOTとの溶液を導入する工程、
− 残りのEDOTと開始剤との溶液の連続的または半連続的な導入と並行して、攪拌及び加熱を継続する工程
を含む、方法。 - 電解質(コ)ポリマーがスチレンとスチレンスルホン酸塩とからなる、請求項1に記載の方法。
- 電解質(コ)ポリマーが、アクリル酸の塩と少なくとも1種類のアルキル(メタ)アクリレートとからなる、請求項1に記載の方法。
- 開始剤が水溶性である、請求項1に記載の方法。
- 開始剤が過硫酸塩である、請求項1に記載の方法。
- 開始剤が過硫酸アンモニウムである、請求項1に記載の方法。
- 請求項1から6のいずれか一項に記載の方法によって得られるラテックス。
- ナノ充填剤を分散させるための請求項7に記載のラテックスの使用。
- ナノ充填剤がカーボンナノチューブである、請求項8に記載のラテックスの使用。
- ナノ充填剤が単層カーボンナノチューブである、請求項8に記載のラテックスの使用。
- 透明導電膜を調製するための請求項7から10のいずれか一項に記載のラテックスの使用。
- 請求項11に記載の使用から得られる透明導電膜。
- オプトエレクトロニクス用途、とりわけ光起電力有機電池における、請求項12に記載の透明導電膜の使用。
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PCT/FR2014/052749 WO2015063415A1 (fr) | 2013-10-31 | 2014-10-29 | Procédé de synthese de pedot-(co) - polymère électrolyte |
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WO2012042492A2 (fr) * | 2010-09-29 | 2012-04-05 | Hutchinson | Nouvelle composition pour film transparent conducteur |
WO2012078191A1 (en) * | 2010-12-07 | 2012-06-14 | Rhodia Operations | Electrically conductive nanostructures, method for making such nanostructures, electrically conductive polymer films containing such nanostructures, and electronic devices containing such films |
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WO2012042492A2 (fr) * | 2010-09-29 | 2012-04-05 | Hutchinson | Nouvelle composition pour film transparent conducteur |
WO2012078191A1 (en) * | 2010-12-07 | 2012-06-14 | Rhodia Operations | Electrically conductive nanostructures, method for making such nanostructures, electrically conductive polymer films containing such nanostructures, and electronic devices containing such films |
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US20160257780A1 (en) | 2016-09-08 |
KR101828194B1 (ko) | 2018-02-09 |
EP3063248A1 (fr) | 2016-09-07 |
WO2015063415A1 (fr) | 2015-05-07 |
FR3012456A1 (fr) | 2015-05-01 |
DK3063248T3 (da) | 2019-11-18 |
CN105916960A (zh) | 2016-08-31 |
TWI543990B (zh) | 2016-08-01 |
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