JP6328609B2 - 水にナノフィラーを分散させるブロックコポリマー - Google Patents
水にナノフィラーを分散させるブロックコポリマー Download PDFInfo
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Description
本発明はまた、本発明のブロックコポリマーによって得られる、ナノフィラーの分散系に関し、有機太陽電池又は他の発光体若しくは受光体デバイスにおける透明電極として前記分散系の使用にも関する。
「安定な分散系」という用語は、沈渣を呈さず、少なくとも1週間均一なままの分散系を意味するよう意図されている。
ポリ(3−ヘキシルチオフェン)−ポリ(スチレン−co−スチレンスルホネート)ブロックコポリマーの合成
蒸留したばかりのテトラヒドロフラン(THF)50ml、2,5−ジブロモ−3−ヘキシルチオフェン7g及び塩化tert−ブチルマグネシウム10.7mlを、真空下で乾燥させ攪拌機を備えた丸底フラスコ500mlに導入し、アルゴンでパージする。周囲温度にて、3時間で反応を完了させる。次いで、蒸留したばかりのTHF150ml及び[1,3−ビス−(ジフェニルホスフィノ)プロパン]ジクロロニッケル(II)であるNi(dppp)Cl20.3628gを加えつつ、40分間撹拌し続ける。次いで、臭化アリルマグネシウム8.64mlを加える。真空下で溶媒を蒸発させた後、過量のメタノールを用いてポリマーを沈殿させる。次いで、ソックスレー装置を使用し、メタノールを用いて3日間、及びクロロホルムを用いて2日間ポリマーを精製する。ポリスチレン試料で較正したSECを用い、数平均分子量を測定し、4522g/molとなる。分散度は1.1である。
蒸留したばかりのテトラヒドロフラン(THF)120mlを、真空下で乾燥させ攪拌機を備えた500mlの丸底フラスコに導入し、アルゴンでパージする。a)で調製したポリマー1.4g及び9−ボラビシクロ[3.3.1]ノナン(9−BBN)1.75mlを丸底フラスコに導入する。次いで、溶液を45℃で24h撹拌し、次いで、周囲温度に冷却し、続いて水中30%の過酸化水素1.21mlを加える。混合物を、撹拌しながら、24hにわたり再度45℃に加熱する。次いで、メタノールからポリマーを沈殿させる。
3−メルカプトプロピオン酸10ml(1当量)を水酸化カリウムの溶液(13g、2当量)に加える。次いで、二硫化炭素15mlを加え、次いで、反応物を周囲温度で5h撹拌する。次いで、臭化ベンジル27.4mlをこの溶液に加え、生じた混合物を80℃で12h撹拌する。次いで、反応混合物を周囲温度に冷却し、クロロホルム150mlをそこに加え、次いで、反応混合物が黄色になるまで、塩酸を用いて反応混合物を酸性化する。混合物の水性相をクロロホルムを用いて抽出する。有機相を取り除き、硫酸マグネシウムで乾燥させる。フラッシュクロマトグラフィーにより、3:1のヘプタン/酢酸エチル混合物を用いて最終生成物を精製すると、最終的に黄色の粉末が得られる。
蒸留したばかりのジクロロメタン20mlを、真空下で乾燥させ攪拌機を備えた100mlの丸底フラスコに導入し、アルゴンでパージする。工程b)で調製したポリマー1gを加える。混合物を45℃で加熱することにより可溶化を実行する。次いで、工程c)で調製したRAFT剤0.125g、続いて、4−(ジメチルアミノ)−4−トルエンスルホン酸ピリジニウム0.03g及びN,N'−ジイソプロピル−カルボジイミド0.09mlを加える。得られた混合物を、撹拌しながら30℃で3日間放置する。次いで、ポリマーをメタノールから沈殿させる。
工程d)で得たRAFTの高分子開始剤1g及びスチレン5mlを、100mlの丸底フラスコに撹拌しながら導入する。媒体の良好な均一化を促進するために、混合物を45℃にする。アルゴンを用いて不活性化した後で、温度を120℃にし、この温度で、混合物を4h撹拌しながら保持する。丸底フラスコを液体窒素に浸すことにより得られた混合物を冷却する。得られたブロックコポリマーは、SECにより特性決定され、49755g/molのMn及び分散度1.2を有する(陽子NMRにより14000g/molのMn(PS)が測定される)。
ジクロロエタン3ml及び無水酢酸2mlを、50mlの丸底フラスコに導入する。アルゴン下で保持したこの溶液(1)を、氷浴で0℃に冷却し、96%の硫酸0.88mlをそこに加える。
コポリマーの物理化学的特性決定
100℃で24h撹拌して、0.2g/l超の濃度のコポリマー水溶液を得る。0.2g/l未満の濃度に関しては、希釈を実行する。
多層カーボンナノチューブの分散系
本発明のブロックコポリマーの存在下で、水中のカーボンナノチューブの分散系を、超音波処理器を使用して、出力950ワット、02/02パルスで10分間実行し、最終的には水浴中で、周囲温度にて、出力285ワットで実行する。
膜の形成及び特性決定
「ドクターブレード法」の技術により、ガラス表面において、実施例3の分散系を使用して膜を調製する。次いで、この膜を、400−800nmの波長範囲(Shimadzu UV−VIS−NIR分光光度計機器(UV−3600)を用いた)の透過率、及び抵抗性(Jandel instrument、RM3−ARモデルを用いた)により特性決定する。形成される膜の厚さ(ナノメートル)も、(Alpha−Step IQ表面形状測定機器を用いて)特性決定する。
官能基化した単層カーボンナノチューブ(Carbon solution Inc.)を、硝酸を使用して精製し、実施例3と同一の技術を用いて分散させる。
実施例3に記載されている方法に従って、10重量%の触媒及び20重量%のグラファイトを含有する非官能基化単層カーボンナノチューブ(Hanwha Nanotech、Korea)を分散させ、凍結乾燥後、高解像度透過顕微鏡法により観察する。写真3では、本発明のコポリマーに対応する、これらのナノチューブの良好な分散系及びカーボンナノチューブの表面の薄層が観察される。
ポリ(3−ヘキシルチオフェン)−ポリ(アクリル酸)ブロックコポリマーの合成:
まず、Arkema社から入手できるBlocbuilder(登録商標)を使用して、ニトロキシドを介した精密ラジカル重合(NMP)により、ポリ(3−ヘキシルチオフェン)−ポリ(アクリル酸tert−ブチル)ブロックコポリマーを合成する。Mougnier等による出版物、Journal of Pol.Science Part A:Polymer chemistry.2012年、50、2463で記載されている、Blocbuilder(登録商標)終端ポリ(3−ヘキシルチオフェン)高分子開始剤を合成した。トルエン中にて120℃で、酸素なしでアクリル酸tert−ブチルの重合を実行する。次いで、ポリ(3−ヘキシルチオフェン)−ポリ(アクリル酸tert−ブチル)コポリマーを、メタノールを用いて沈殿させ、次いで、1:4のジオキサン/トリフルオロ酢酸(TFA)混合物中で加水分解することにより、ポリ(3−ヘキシルチオフェン)−ポリ(アクリル酸)に変換させる。
本発明のコポリマー又はポリ(3−ヘキシルチオフェン)−ポリ(アクリル酸)の何れかを使用する同一条件下で、実施例3及び4に従って、分散系及び膜を調製する。
Claims (12)
- 可溶性である又は水中で安定な分散系を呈し、かつ共役ポリマーからなる少なくとも1つのブロック及びスチレン−スチレンスルホネート型の多価電解質ポリマーからなる少なくとも1つのブロックを有する少なくとも1つのブロックコポリマー、並びにナノフィラーを含み、ナノフィラーが、グラフェン、フラーレン、カーボンナノチューブ、又はそれらの組み合わせから選択される、組成物。
- ブロックコポリマー(複数可)が、ジブロック、トリブロック若しくはマルチブロック型又はそれらの混合物であり、各ブロックのホモポリマーを含む、請求項1に記載の組成物。
- 少なくとも1つのジブロックコポリマーを含む、請求項1に記載の組成物。
- 共役ポリマーが、チオフェン誘導体である、請求項1に記載の組成物。
- チオフェン誘導体が、3−アルキルチオフェンである、請求項4に記載の組成物。
- チオフェン誘導体が、3−ヘキシルチオフェンである、請求項5に記載の組成物。
- 多価電解質ブロックが、1000から500000g/molの重量平均分子量を有する、請求項1に記載の組成物。
- 共役ポリマーブロックが、1000から50000g/molの重量平均分子量を有する、請求項1に記載の組成物。
- 太陽光発電フィールド、又は発光体若しくは受光体デバイスにおける、請求項1から8の何れか一項に記載のブロックコポリマー、及びナノフィラーを含む、水性分散系の使用。
- ナノフィラーが、グラフェン、フラーレン、カーボンナノチューブ、又はそれらの組み合わせから選択される、請求項9に記載の使用。
- ナノフィラーが、カーボンナノチューブからなる、請求項9に記載の使用。
- ナノフィラーが、多層カーボンナノチューブからなる、請求項9に記載の使用。
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FR1253228A FR2989091B1 (fr) | 2012-04-06 | 2012-04-06 | Copolymeres a bloc dispersants de nanocharges dans l'eau |
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PCT/FR2013/050734 WO2013150242A1 (fr) | 2012-04-06 | 2013-04-03 | Copolymeres a bloc dispersants de nanocharges dans l' eau |
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FR3012456B1 (fr) * | 2013-10-31 | 2018-01-26 | Arkema France | Procede de synthese de pedot-(co) - polymere electrolyte |
FR3012461B1 (fr) * | 2013-10-31 | 2016-01-01 | Arkema France | Compositions stables de nanotubes de carbone - polymeres electrolytes |
KR101681186B1 (ko) | 2014-07-21 | 2016-12-01 | 한국과학기술연구원 | 외부자극에 의하여 자가도핑이 가능한 cnt-고분자 복합체 및 이의 제조방법 |
EP3421545A4 (en) * | 2016-02-22 | 2020-03-11 | Sekisui Chemical Co., Ltd. | COMPOSITE MATERIAL, CONDUCTIVE MATERIAL, CONDUCTIVE PARTICLES AND CONDUCTIVE FILM |
WO2020022503A1 (ja) | 2018-07-26 | 2020-01-30 | 国立大学法人名古屋大学 | 非共有結合性ナノカーボン-ポリマーハイブリッド組成物 |
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FR2870121B1 (fr) * | 2004-05-12 | 2006-07-21 | Oreal | Composition cosmetique comprenant au moins un copolymere bloc specifique. |
TWI271876B (en) * | 2005-05-27 | 2007-01-21 | Univ Nat Taiwan | Block copolymer containing nano-particles, electron transporting material and photoelectric device employing the same |
US20080319131A1 (en) * | 2005-08-26 | 2008-12-25 | Mccullough Richard D | Electrically Conductive Polymers and Raft Polymerization |
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US8211969B2 (en) * | 2007-10-10 | 2012-07-03 | University Of Central Florida Research Foundation, Inc. | Dispersions of carbon nanotubes in copolymer solutions and functional composite materials and coatings therefrom |
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US8715606B2 (en) * | 2007-12-21 | 2014-05-06 | Plextronics, Inc. | Organic photovoltaic devices comprising fullerenes and derivatives thereof and improved methods of making fullerene derivatives |
US8211996B2 (en) * | 2008-12-01 | 2012-07-03 | The Regents Of The University Of California | Well-defined donor-acceptor rod-coil diblock copolymer based on P3HT containing C60 |
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FR2989091A1 (fr) | 2013-10-11 |
US20150060737A1 (en) | 2015-03-05 |
JP2015517010A (ja) | 2015-06-18 |
KR20140147882A (ko) | 2014-12-30 |
EP2834305A1 (fr) | 2015-02-11 |
US9558861B2 (en) | 2017-01-31 |
CN104428367A (zh) | 2015-03-18 |
FR2989091B1 (fr) | 2015-07-03 |
WO2013150242A1 (fr) | 2013-10-10 |
EP2834305B1 (fr) | 2018-07-11 |
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