JP2010257981A - 導電性ポリマー及びポリウレタンを含む分散体から形成された導電性フィルム - Google Patents
導電性ポリマー及びポリウレタンを含む分散体から形成された導電性フィルム Download PDFInfo
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- JP2010257981A JP2010257981A JP2010101245A JP2010101245A JP2010257981A JP 2010257981 A JP2010257981 A JP 2010257981A JP 2010101245 A JP2010101245 A JP 2010101245A JP 2010101245 A JP2010101245 A JP 2010101245A JP 2010257981 A JP2010257981 A JP 2010257981A
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Images
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Abstract
【解決手段】水性分散体及び該水性分散体の製造方法である。ポリチエノチオフェンなどの少なくとも1つの導電性ポリマー、少なくとも1つのポリウレタンポリマー、及び所望により、少なくとも1つのコロイド形成ポリマー酸及び1つの非フッ素化ポリマー酸を含む分散体である。また、本発明の分散体から形成された層を用いるデバイスも開示される。
【選択図】図1
Description
アノード/正孔注入層/EL層/カソード
を有する。
陽極/正孔抽出層/集光層(単数又は複数)/陰極
を有する。
(a)少なくとも1つの酸化剤及び/又は少なくとも1つの触媒を含む水溶液を準備する工程;
(b)有効量のポリウレタンポリマーを含む水性分散体を準備する工程;
(c)前記の酸化剤及び/又は触媒の水溶液と前記ポリウレタンポリマーの水性分散体を混合する工程;
(d)導電性ポリマーのモノマー又は前駆体を工程(c)の混合された水性分散体に加える工程;
(e)前記モノマー又は前駆体含有ポリウレタン分散体を重合して、ポリマー分散体を形成する工程;
(f)ポリマー分散体をイオン交換樹脂(単数又は複数)に接触させて、不純物を除去する工程;並びに
(g)所望により、前記ポリマー分散体のpHを、さらに好ましい性質を提供するのに十分に高いpHに調整する工程
を含む。
(a)少なくとも1つの酸化剤及び/又は少なくとも1つの触媒を含む水溶液を準備する工程;
(b)適量のポリウレタンポリマーを含む水性分散体を準備する工程;
(c)工程(b)のポリウレタンポリマーの水性分散体を導電性ポリマーのモノマー又は前駆体に加える工程;
(d)工程(a)の酸化剤及び/又は触媒溶液を工程(c)の混合物に加える工程;
(e)前記モノマー又は前駆体含有ポリウレタン分散体を重合して、導電性ポリマー分散体を形成する工程;
(f)前記ポリマー分散体をイオン交換樹脂(単数又は複数)と接触させて、不純物を除去する工程;並びに
(g)所望により、前記ポリマー分散体のpHを、さらに好ましい性質を提供するのに十分に高いpHに調整する工程
を含む。
(i)有機イソシアネートに、−−OH、−−NH2、及び−−SH、及び所望により低分子量イソシアネート反応性化合物から選択される1つ以上のイソシアネート反応性基を含む化合物を反応させることにより、少なくとも1つのイソシアネート基を有するプレポリマーを調製する工程であって;イソシアネート及びイソシアネート反応性基を含む化合物(所望により、イソシアネート−反応性化合物)の一方又は両方は、親水性部分を含み;そして所望により、イソシアネート及びイソシアネート反応性基を含む化合物の一方又は両方は、式(1A)〜(1D)の少なくとも1つのペンダント側鎖を含む工程;
(ii)所望により、工程(i)のプレポリマーに、式(1A)〜(1D)の少なくとも1つのペンダント側鎖を有するアミン鎖延長剤を反応させる工程;
(iii)所望により、未反応イソシアネート末端基に、連鎖停止剤としてのモノ−イソシアネート反応性化合物を反応させる工程;並びに
(iv)工程(ii)の反応生成物を水性媒体に分散する工程
を含む、水性ポリウレタン/尿素分散体の製造方法を提供する。
i)側部の親水性エチレンオキシド単位を含むジイソシアネート、
ii)イソシアネート−重付加反応において二官能であり、かつ側部の親水性エチレンオキシド単位を含む化合物、
iii)末端の親水性エチレンオキシド単位を含むモノイソシアネート
iv)イソシアネート−重付加反応において単官能であり、かつ末端の親水性エチレンオキシド単位を含む化合物、並びに
v)これらの混合物
を含む。
−−(O−−CF2CFRf)a−−O−−CF2CFR’fSO3X
(式中、Rf及びR’fは、独立してF、Cl又は1〜10個の炭素原子を有する完フッ素化アルキル基から選択され、a=0、1又は2、そしてXはH、Li、Na、K又はN(R1’’)(R2’’)(R3)(R4)の少なくとも1種を含み、そしてR1”、R2”、R3、及びR4は、同一であるか、又は異なっており、そして一実施形態では、H、CH3又はC2H5である)によって表される側鎖を含む。別の実施形態では、XはHを含む。上記の通り、Xは多価でもよい。
−−O−−CF2CF(CF3)−−O−−CF2CF2SO3X’
{式中、X’は上記で規定した通りである)
により表される側鎖を含む。この種類のFSAポリマーは、米国特許第3,282,875号明細書に開示されており、テトラフルオロエチレン(TFE)及び完フッ素化ビニルエーテルCF2=CF−−O−−CF2CF(CF3)−−O−−CF2CF2SO2F、ペルフルオロ(3,6−ジオキサ−4−メチル−7−オクテンスルホニルフルオリド)(PDMOF)を共重合し、次に、フッ化スルホニル基の加水分解によってスルホネート基に変換して、必要に応じてイオン交換してそれらを好ましいイオン形態に変えることにより、形成できる。米国特許第4,358,545号明細書及び第4,940,525号明細書に開示されている種類のポリマーの例は、側鎖−−O−−CF2CF2SO3X’{式中、X’は上記で規定した通りである)を有する。このポリマーは、テトラフルオロエチレン(TFE)及び完フッ素化ビニルエーテルCF2=CF−−O−−CF2CF2SO2F、ペルフルオロ(3−オキサ−4−ペンテンスルホニルフルオリド)(POPF)の共重合と、次の加水分解、さらに必要に応じてイオン交換により形成できる。
(1)アルコール、例えばメチルアルコール、エチルアルコール、n−プロピルアルコール、イソプロピルアルコール、n−ブチルアルコール、sec−ブチルアルコール、t−ブチルアルコール、イソ‐ブチルアルコール、フルフリルアルコール、及びテトラヒドロフルフリルアルコールなど;
(2)多価アルコール、例えばエチレングリコール、ジエチレングリコール、トリエチレングリコール、テトラエチレングリコール、プロピレングリコール、ポリエチレングリコール、グリセロール、2−メチル−2,4−ペンタンジオール、1,2,6−ヘキサントリオール、2−エチル−2−ヒドロキシメチル−1,3−−プロパンジオール、1,5ペンタンジオール、1,2−ヘキサンジオール、及びチオグリコールなど;
(3)多価アルコール由来の低級モノ−及びジ−アルキルエーテル;
(4)窒素含有化合物、例えば2−ピロリドン、N−メチル−2−ピロリドン、及び1,3−ジメチル−2−イミダゾリジノン;並びに
(5)硫黄含有化合物、例えば、2,2’−チオジエタノール、ジメチルスルホキシド及びテトラメチレンスルホン、
6)ケトン、エーテル及びエステル
が挙げられる。
(1)電気エネルギーを放射線に変換するデバイス(例えば、発光ダイオード、発光ダイオードディスプレー、又はダイオードレーザー)、(2)電子プロセスを通してシグナルを検出するデバイス{例えば、光検出器(例えば、光伝導セル、光レジスタ、光スイッチ、光トランジスタ、光電管)、IR検出器}、(3)放射線を電気エネルギーに変換するデバイス(例えば、光電池デバイス又は太陽電池)、並びに(4)1つ以上の有機半導体層(例えば、トランジスタ又はダイオード)を含む1つ以上の電子部品を含むデバイスが挙げられる。
ポリウレタンポリマーの合成のための一般的な手順について以下に概略が説明されており、本開示に従って合成されたポリウレタンポリマーが表1にまとめられている。
1.ポリオール及びジイソシアネート、並びに任意の溶媒を反応器中に加えて攪拌した。反応器の温度を緩やかに40℃に上げてポリオールを溶解した。
2.反応物が均質の混合物になった後、1滴のジブチル錫ジラウレート(DBTDL T−12、0.1wt%未満で十分であった)を反応器中に加えた。この反応の発熱性のために、反応の温度を50〜80℃(122〜176°F)へ上昇させた。循環水により該温度を制御した。
3.理論上のNCO数に達するまで、反応の温度を約40℃(104°F)に維持した。通常では、約1時間かかった。
4.理論上のNCO数に達した後、反応温度を室温に下げて、アセトンを加えてプレポリマーを50重量%に希釈した。
1.所望により、次にジアミン鎖延長剤EES−200Lを反応器中に加えた。
2.所望により、EES−200Lによる鎖延長反応後、20重量%水溶液として連鎖停止剤タウリン−Na+を加えて、反応を停止させた。
3.反応物が約20%固体で通常は透明になるまで、等量の水及びアセトン、所望により、テトラヒドロフラン(THF)で該反応物を希釈した。
4.アセトンを減圧下で除去した。等量のイオン交換樹脂AMBERLITE(登録商標)IR−120カチオン交換樹脂(シグマ−アルドリッチケミカル(Sigma−Aldrich Chemical)社)並びに94.0gのLEWATIT(登録商標)MP−62アニオン交換樹脂(Fluka、シグマ−アルドリッチケミカル社)IR−120及びMP−62によりイオン性不純物を除去して、透明な水性分散体を得た。
5.分析技術によりポリウレタン分散体を分析して、分子量、カチオン及びアニオン性不純物、並びに残留溶媒、pH、粘度、粒径、並びに仕事関数を決定した。
一般的な手順を用いて、本開示の導電性ポリマー分散体を合成した。
1700gの脱イオン水を3Lジャケット付き反応器に加えた。水中の600gの12%NAFION(登録商標)(デラウェア州Wilmingtonのデュポン社より供給されたEW1100)分散体を反応器中に加え、オーバーヘッド攪拌器で5分間混合した。ジャケット付きフラスコを調整して22℃(72°F)の反応温度を維持した。350gの脱イオン水に溶解している17.7g(34.2mmol)のFe2(SO4)3・H2Oを有する反応器中に4.0g(28.6mmol)のEDOTを個別に共供給した。充填時のNAFION(登録商標):EDOTの質量比は18:1であった。本反応体は、20分以内に薄緑から、エメラルドグリーンへ、そしてダークブルーへ変わった。モノマー及び酸化剤の導入後、重合を4時間進めさせた。次に、94.0gのAMBERLITE(登録商標)IR−120カチオン交換樹脂(シグマ−アルドリッチケミカル社)及び94.0gのLEWATIT(登録商標)MP−62アニオン交換樹脂(Fluka、シグマ−アルドリッチケミカル社)を含む4L NALGENE(登録商標)ボトルに反応器の含有物を加えることによって、得られた分散体を精製したところ、不透明なダークブルーの水性ポリ(チエノ[3,4−b]チオフェン)/NAFION(登録商標)(PTT/NAFION(登録商標)分散体)が生成した。該分散体を10、5、0.65及び0.45μm細孔径のフィルターに連続して通してろ過した。
500mLポリボトルに、202gのイオン交換樹脂、ナトリウム形態のAMBERLITE(登録商標)IR120{AMBERLITE(登録商標)は、ペンシルバニア州フィラデルフィアのローム・アンド・ハーズ(Rohm&Haas)社のイオン交換樹脂について連邦政府によって登録された商標である}、及び300mLのエレクトロニクス用水を充填した。材料充填物を攪拌せずに20〜24℃(68〜75°F)で1〜4時間浸して、その後に60メッシュステンレス鋼スクリーン上に樹脂を回収した。この洗浄工程を室温で合計5回繰り返して、次に、混合物を70℃(158°F)で2時間加熱すること以外は同量の材料を用いて3回以上洗浄した。最終的に、樹脂を60メッシュスクリーン上に回収して、55.2%固体を有する洗浄されたIR120−Naを形成した。
500mLポリボトルに、100gのイオン交換樹脂、水素形態のAMBERLITE(登録商標)IR120、300mLのエレクトロニクス用水、及び100mLの濃縮(28〜30%)水酸化アンモニウムを充填した。20〜24℃(68〜75℃)でジャーローラー(jar roller)上で材料充填物を16時間混合し、その後に、樹脂を60メッシュステンレス鋼スクリーン上に回収した。次に、攪拌せずに1〜4時間300mLのエレクトロニクス用水中に浸すことによって樹脂を洗浄した。この洗浄工程を室温で合計5回繰り返して、次に、混合物を70℃(158°F)で2時間加熱すること以外は同量の材料を用いて3回以上洗浄した。最終的に、樹脂を60メッシュスクリーン上に回収して、56.9%固体を有する洗浄されたIR120−NH4を形成した。
ガラス基板上のITO交差指電極(interdigitated electrode)を用いて、分散体から成型された導電性ポリマー膜の抵抗を測定した。有効電極長は15cmであり、指間の差は20μm(ミクロン)であった。分散体を0.45μm親水性PVDFフィルターでろ過して、抵抗試験のためのITO交差指基材上へ1000rpmのスピン速度で1分間スピンコートした。スピンコート前に、UVOCZ装置上でUV−オゾン処理によってITO基材を洗浄した。次に、窒素を充満させたグローブ・ボックス中にスピンコートされた膜を移し、社内開発したLabVIEWプログラムを用いるコンピュータと適合させたKeithley2400ソースメータ及び自動スイッチを用いて、抵抗を測定した。次に、窒素を充満させたグローブ・ボックス内において、ホットプレート上で膜を180℃(356°F)で15分間アニールし、再び抵抗を測定した。
10〜15Ω/□(Colorado Concept Coating社製)の表面抵抗を有するパターン化されたITO基材を使用して、PLEDデバイスを製造した。脱イオン水、洗剤、メタノール及びアセトンを併用してITO基材を洗浄した。次に、SPI PrepIIプラズマエッチャー内でO2プラズマによってITO基材を約10分間洗浄した。その後に、約50〜100nmの膜厚を得るために選択したスピン速度で、ITO基板に導電性ポリマー分散体をスピンコートした。Laurell型WS−400−N6PPスピナー上で1〜3分であるようにスピン長をプログラミングする。スピンコート前に、0.45μmPVDF親水性フィルターによって、全ての導電性ポリマー分散体をろ過した。均質な膜を得た。次に、窒素を充満させたグローブ・ボックス内において、ホットプレート上で180℃(356°F)でコーティングされたITO基材を15分間アニールした。アニール後、トルエン又はキシレン溶液から約10〜20nm厚の中間層ポリマーの層(住友化学社により供給された)をスピンコートした。次に、N2保護下、ホットプレート上で180〜200℃(356〜392°F)でサンプルを30〜60分ベークした。その後、トルエン又はキシレン溶液から約50〜90nm厚の青色発光ポリマー(住友化学社により供給された)の層をスピンコートした。次に、N2保護下、ホットプレート上でサンプルを130℃(266°F)で10分間ベークした。また、緑色PLEDデバイスを製造した。導電性ポリマー層のアニール後、トルエン溶液から約80nm厚のLUMATION(登録商標)緑色1304LEP発光ポリマー(住友化学社により供給された)の層をスピンコートした。次に、N2保護下、ホットプレート上でサンプルを130℃(266°F)20分間ベークした。次に、窒素雰囲気のグローブ・ボックス内に位置している真空蒸発装置のチャンバ中にサンプルを移した。約1.5Å/sの速度で、防塵マスクを通して、1〜2×10−6mBar以下で5nm厚のBaの層を真空堆積させ、約3.0〜4.0Å/sの堆積速度でBa層の上部に120nm厚のAgの別の層を真空堆積させた。次に、ガラスカバーの蓋及びUV硬化性エポキシによって、窒素グローブ・ボックス内にデバイスを封入した。デバイスの活性面積は、約6.2mm2であった。次に、室温で空気中の試験のためにグローブ・ボックスからLEDデバイスを出した。KLA Tencor P−15プロファイラー上で厚さを測定した。Keithley2400ソースメータ上で電流電圧特性を測定した。Oriel InstaSpec IV CCDカメラを用いて、デバイスのエレクトロルミネッセンス(EL)スペクトルを測定した。また、それは、参照により全体で本明細書に援用される米国特許出願公開第2006/0076557号明細書の図3に示されている。目盛り付きSi光ダイオードと連結したNewport2835−C多機能光学メータを用いて、EL発光の出力を測定した。EL発光のランバート分布と仮定して、デバイスのEL前方出力及びELスペクトルを用いて、明度を算出し、Photo Research PR650比色計によって検証した。室温で定電流駆動条件下で、ELIPSE(商標) PLEDライフタイムテスター(Cambridge Display Technology社製)上でPLEDデバイスの寿命を測定した。Si光ダイオードを用いて測定された初期明度を達成するのに必要な電流密度によって、駆動電流を設定した。この開示の実験のために、青色PLEDデバイスのための初期デバイス明度として3000ニト及び緑色PLEDデバイスのために5000ニトを選択し、デバイスの寿命を、明度が初期値の50%に達するのにかかる時間として規定した。同一インク組成を用いて複合デバイスを形成したため、デバイス性能データを表5に示すような範囲として記録した。これらは、3000ニト(Cd/m2)明度で駆動電圧(ボルト)及び電流(Cd/A)を含み、初期からT50までの電圧変化の百分率(%)によって決定した通り、寿命試験中に駆動電圧は増加する。さらに、デバイス歩留まりの測定を考案して、特定の導電性ポリマーインク由来のデバイス性能のコンシステンシーを評価した。デバイス歩留まりは、実験内で形成された重複デバイスの総数の内で適度なデバイス性能を示したデバイス数の%である。 この点では、用語「適度なデバイス性能」は、下記:電流効率が2Cd/Aを超え、かつ駆動電圧が10ボルト未満である、として規定される。
Claims (23)
- 少なくとも1つの導電性ポリマー;及び
少なくとも1つのポリウレタンポリマー
を含む水性分散体であって、前記ポリウレタンポリマーが少なくとも部分的に水溶性又は水分散性である、水性分散体。 - 前記導電性ポリマーが、ポリアニリン、ポリピロール、ポリチオフェン、ポリセレノフェン;ポリアニリン、ポリピロール、ポリセレノフェン、ポリチオフェンの誘導体;及びこれらの組み合わせからなる群から選択される、請求項1に記載の分散体。
- 前記導電性ポリマーが、ポリアセチレン、ポリチエノチオフェン/ポリスチレンスルホン酸、ポリジオキシチオフェン/ポリスチレンスルホン酸、ポリアニリン−ポリマー酸−コロイド、ポリ(3,4−エチレンジオキシチオフェン)(PEDOT)、PEDOT−ポリマー酸−コロイド、及びこれらの混合物からなる群から選択される少なくとも1種を含む、請求項1に記載の分散体。
- 導電性ポリマーが、ポリ(チエノ[3,4−b]チオフェン)を含む、請求項1に記載の分散体。
- 少なくとも1つのコロイド形成ポリマー酸及び少なくとも1つの非フッ素化ポリマー酸を含む、請求項1に記載の分散体。
- 少なくとも1つのフッ素化スルホン酸ポリマーを含むコロイド形成ポリマー酸を含む、請求項1に記載の分散体。
- 塩基性イオン交換樹脂で処理される、請求項1に記載の分散体。
- 少なくとも1つの塩基性化合物で処理される、請求項1に記載の分散体。
- 前記塩基性化合物が、水酸化ナトリウム、水酸化アンモニウム、水酸化テトラメチルアンモニウム、水酸化テトラエチルアンモニウム、水酸化カルシウム、水酸化セシウム、及びこれらの組み合わせからなる群から選択される少なくとも1種を含む、請求項8に記載の分散体。
- 前記ポリウレタンポリマーが、酸形態又は中和された形態のいずれかの少なくとも1つのスルホン酸、ホスホン酸、ボロン酸、若しくはカルボン酸、又はこれらの組み合わせを含む、請求項1に記載の分散体。
- 前記ポリウレタンポリマーが、ケイ素及びフッ素原子を含む、請求項1に記載の分散体。
- 前記ポリウレタンポリマーが、フッ素化アルキレンオキシド部分を含む、請求項1に記載の分散体。
- 前記ポリウレタンポリマーが、シロキサン部分を含む、請求項1に記載の分散体。
- 前記ポリウレタンポリマーが、ポリアルキレンオキシド部分を含む、請求項1に記載の分散体。
- 前記ポリウレタンポリマーが、前記ポリウレタンの全繰り返し単位を基準に、ペンダント側鎖として、酸形態又は中和された形態のいずれかのスルホン酸、ホスホン酸、ボロン酸、若しくはカルボン酸、又はこれらの組み合わせを組み込んでいる少なくとも5モル%の繰り返し単位を含む、請求項1に記載の分散体。
- ポリアニリン、ポリピロール、ポリチオフェン、ポリセレノフェン;ポリアニリン、ポリピロール、ポリセレノフェン、ポリチオフェンの誘導体;及びこれらの組み合わせを含むポリウレタンポリマーを分散した導電性膜を含む、電子デバイス。
- 前記導電性膜と接触している少なくとも1つのポリチオフェン及び少なくとも1つの導電性電極をさらに含む、請求項16に記載のデバイス。
- 有機電子デバイスを含む、請求項16に記載のデバイス。
- 有機発光ダイオード、有機光電子デバイス、有機太陽電池デバイス、ダイオード及びトランジスタからなる群から選択される少なくとも1種を含む、請求項16に記載のデバイス。
- (a)酸化剤及び触媒の1つ以上を含む水溶液を準備する工程;
(b)有効量のポリウレタンポリマーを含む水性分散体を準備する工程;
(c)前記酸化剤及び/又は触媒の水溶液と前記ポリウレタンポリマーの水性分散体を混合する工程;
(d)導電性ポリマーのモノマー又は前駆体を工程(c)の混合された水性分散体に加える工程;
(e)前記モノマー又は前駆体含有ポリウレタン分散体を重合して、ポリマー分散体を形成する工程;並びに
(f)前記ポリマー分散体を単数又は複数のイオン交換樹脂に接触させて、不純物を除去する工程
を含む、少なくとも1つの導電性ポリマー、及び少なくとも1つのポリウレタンポリマーを含む水性分散体の製造方法。 - イオン交換樹脂又は塩基性溶液を用いて、前記ポリマー分散体のpHを調整する工程をさらに含む、請求項20に記載の方法。
- (a)少なくとも1つの酸化剤及び/又は少なくとも1つの触媒を含む水溶液を準備する工程;
(b)有効量のポリウレタンポリマーを含む水性分散体を準備する工程;
(c)工程(b)のポリウレタンポリマーの水性分散体を導電性ポリマーのモノマー又は前駆体に加える工程;
(d)工程(a)の酸化剤及び/又は触媒溶液を工程(c)の混合物に加える工程;
(e)前記モノマー又は前駆体含有ポリウレタン分散体を重合して、導電性ポリマー分散体を形成する工程;並びに
(f)前記ポリマー分散体を単数又は複数のイオン交換樹脂に接触させて、不純物を除去する工程
を含む、少なくとも1つの導電性ポリマー、及び少なくとも1つのポリウレタンポリマーを含む水性分散体の製造方法。 - イオン交換樹脂又は塩基性溶液を用いて、前記ポリマー分散体のpHを調整する工程をさらに含む、請求項22に記載の方法。
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JP2013531077A (ja) * | 2010-04-21 | 2013-08-01 | ソルヴェイ・スペシャルティ・ポリマーズ・イタリー・エッセ・ピ・ア | 含フッ素ポリウレタン組成物 |
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KR20200067261A (ko) | 2017-01-31 | 2020-06-12 | 도쿄 오카 고교 가부시키가이샤 | 중합성 조성물, 경화막의 제조 방법 및 경화막 |
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Also Published As
Publication number | Publication date |
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KR20100118083A (ko) | 2010-11-04 |
JP5270611B2 (ja) | 2013-08-21 |
KR101193121B1 (ko) | 2012-10-19 |
TW201038668A (en) | 2010-11-01 |
TWI432518B (zh) | 2014-04-01 |
EP2253650A1 (en) | 2010-11-24 |
US20100270055A1 (en) | 2010-10-28 |
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