JP2008007781A - 表面変性された炭化物質 - Google Patents
表面変性された炭化物質 Download PDFInfo
- Publication number
- JP2008007781A JP2008007781A JP2007193021A JP2007193021A JP2008007781A JP 2008007781 A JP2008007781 A JP 2008007781A JP 2007193021 A JP2007193021 A JP 2007193021A JP 2007193021 A JP2007193021 A JP 2007193021A JP 2008007781 A JP2008007781 A JP 2008007781A
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- Prior art keywords
- carbon
- polymer
- grafted
- carbonized material
- solution
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Abstract
【解決手段】カルボキシル基、アミン基、および/またはヒドロキシル基を有するグラフトさせようとするポリマーを含み、そしてさらにポリマーの溶媒を含んだ溶液中に炭化物質を懸濁させる。次いで、カルボキシル基、アミド基、および/またはヒドロキシル基に脱水を引き起こさせる処理を施し、このようにしてポリマーをエステル結合またはアミド結合によって炭化物質にグラフトさせる。このように表面変性された炭化物質は、電気化学的発電体のカソードまたはアノードとして、極性の低いポリマー物質として、そしてインキとして使用され、また軟質プラスチック上への導電性デポジットは、電気接点、電磁気に対する保護物、および帯電防止用保護物として使用される。
【選択図】なし
Description
本発明は、炭化物質の表面にポリマーをグラフトさせるための新規方法、およびこのようにして得られる物質を導電性添加剤として〔特に電気化学的発電体(electrochemical generator)において〕、導電性のデポジットとして、あるいはインキとして応用することに関する。
従来の技術
炭化物質は、多くの分野〔例えば、構造用成分(炭素繊維をベースとする複合材料等)、顔料(インキ、トーナー、またはペイント等)、電極(二重層キャパシタンスやアルミニウムの電気分解等)、イオン交換体(重金属の除去や水の精製等)、触媒担体(可燃性のマテリアルバッテリー(material battery)等)、および無機装入材料(ゴム工業やタイヤ等)〕において重要な役割を果たしている。
発明の総括
これらの問題点を解消すべく検討を重ねた結果、発明者らは、本発明において、実施の容易な脱水メカニズムによってエステル結合またはアミド結合を介してポリマーセグメントを炭化物質の表面に固定させることからなる、ポリマーでグラフトされた炭化物質の新規製造法を提供する。
発明の説明
本発明は、粉末または繊維の形態をとっている炭化物質の表面に存在しているカルボキシル基、アミン基、またはヒドロキシル官能基に、少なくとも1つのカルボキシル基、ヒドロキシル基、またはアミン官能基を有するポリマーをグラフト結合させることのできる新規方法を提供する。このように、化学結合は、エステル結合またはアミド結合を介してもたらされる。
さらに、FW200/J-2000とリチウムビス(トリフルオロメタンスルホニル)イミドとを含有するポリオキシエチレンのマトリックスの押し出しは、ある容量フラクションのシャウィニガンブラックを含有する同じマトリックスの場合よりはるかに容易である、ということを示すことができた。
重合可能なビニルエーテル官能基を含んだ炭素は、導電性のデポジットを得るのに、あるいはオフセットインキを製造するのに特に有用である。このように、ビニルエーテル官能基と光開始剤とを含んだ反応性溶媒中への、ビニルエーテル官能基を有する炭素の懸濁液を調製することができる。これらの懸濁液をある支持体上に塗布した後、表面を紫外線ランプで照射することによって炭素デポジットが得られる。これらのデポジットは、液体、ゲル、またはポリマー電解質のリチウム電池(イオンの拡散を制限する極性の低い溶媒が好ましい)において使用されているアルミニウムコレクタの腐食を防止するのに特に有用である。一方、これらの懸濁液は、オフセットプロセスのための紫外線照射後の固定化が速やかな印刷用インキを製造するのに使用することができる。これらの懸濁液はさらに、ポリマー電解質リチウム電池において使用されるリチウムアノードヘの導電性デポジットを得るのにも使用することができる。
表面に0.61ミリモル/gのカルボキシル基を有する200g(122ミリモルのカルボキシル基)の酸化炭素FW200(デグッサ社から市販)を600mlのトルエン中に懸濁させて得られる懸濁液に、136g(122ミリモル)のポリオキシアルキレンモノアミン〔1116g/モルの平均分子量を有するジェファーミン(登録商標)M-1000(J-1000、ハンツマン社から市販)〕を加えた。ジェファーミン(登録商標)の分子量は塩酸滴定によって測定した。ジェファーミン(登録商標)中に存在している水とアンモニアは、乾燥アルゴンを60℃で24時間バブリングすることによって除去した。カールフィッシャー滴定法による残留水分の測定値が100ppm以下であることから、このプロセスの有効性が確認された。磁化テフロン(登録商標)のオリーブ形状物(olive)で撹拌を保持することによって、懸濁液の共沸蒸留を行った。約30分後にデイーン−シュタルク中にて溶媒の還流が始まり、そしてその約10分後に最初の液滴が観察された。20時間の還流後、捕集した水の量は約2.lmlであって、これは予想値と一致しており(122ミリモルの−COOHのアミド化に対しては2.2ml)、新たな水滴の生成は観察されなかった。還流を4時間継続した。冷却後、反応混合物を200mlに濃縮し、1リットルのエーテル中に注ぎ込んだ。次いでグラフト化炭素を濾過によって回収し、これを減圧乾燥した。
実施例2
実施例1に記載のプロセスと類似のプロセスにしたがって、表面に0.61ミリモル/gのカルボキシル基を有する50g(30.5ミリモルのカルボキシル基)のFW200(デグッサ社から市販)と、2219g/モルの平均分子量を有する67.7g(30.5ミリモル)のジェファーミン(登録商標)M-2070(J-2070、ハンツマン社から市販)(実施例1に記載のように精製・特性付けした)とを反応させた。光沢ある外観をもつ物質が得られ、このことは表面がジェファーミン(登録商標)M-2070で被覆されていることを示している。
表面に0.61ミリ当量/gのカルボキシル基を有する200g(122ミリモルのカルボキシル基)の酸化炭素FW200(デグッサ社から市販)を300mlのベンゼン中に懸濁させて得られる懸濁液に、13.15g(130ミリモル)のモノアミンビニルエーテル、3−アミノ−1−プロパノールビニルエーテル〔CH=CHO(CH2)3NH2〕(BASF社から市販)を加えた。次いで、磁化テフロン(登録商標)のオリーブ形状物で撹拌を保持することによって懸濁液の共沸蒸留を行った。約30分後にディーン−シュタルク中にて溶媒の還流が始まり、そしてその約10分後に最初の液滴が観察された。14時間の還流後、捕集した水の量は約2.lmlであって、これは予想値と一致しており(122ミリ当量の−COOHのアミド化に対しては2.2ml)、新たな水滴の生成は観察されなかった。還流を2時間継続した。冷却後、グラフト化炭素を濾過によって回収し、これを減圧乾燥した。
実施例1に記載のプロセスと類似のプロセスにしたがって、164gのFW200(100ミリモルのカルボキシル基)を、2219g/モルの平均分子量を有する166.4g(75ミリモル)のジェファーミン(登録商標)M-2070(J-2070)(実施例1に記載のように精製・特性付けした)および2.53g(25ミリモル)の3−アミノ−1−プロパノールビニルエーテル(BASFから市販)と反応させた。
ナルゲネフラスコ(Nalgene flask)中に、7g(70重量%)の実施例2で得られたグラフト化炭素、3g(30重量%)のポリ(エチレンオキシド)(MW=3×105)、および50mlのアセトニトリルを導入した。ジルコニアロールを加え、フラスコをシャフトにより回転させた。24時間後、ポリ(エチレンオキシド)中炭素がアセトニトリル中に懸濁した状態の安定な懸濁液が得られた。次いでこの懸濁液を、テフロン処理アルミニウムのシート上に配置されたガラスリング中に注ぎ込んだ。溶媒を蒸発させるのに必要とされた時間(約24時間)中、グラフト化炭素の沈降は観察されなかった。溶媒を蒸発除去した後、得られたフィルムを減圧下で48時間乾燥した。実際に29重量%の炭化物質(すなわち20重量%)を含有するこのフィルムは、驚くべきことに、極めて均一な外観をもち、孔が認められない。このフィルムは10-3Ω.cm-1以上の導電率を有する。
実施例6
実施例2で得られたグラフト化炭素を酸化バナジウムV2O5と共に粉砕することによって複合カソードを製造した。次いで2トンでプレスすることによって、緻密で非多孔質の複合カソードを得た。次に打ち抜きすることによってパステル(pastil)をカットし、カソードとして使用される電気化学的発電体上に据え付けた〔このとき前記発電体はさらに、ビス(トリフルオロメタンスルホニル)イミドのリチウム塩をO/Li=15/1の濃度にて含有する、5×106g/モルの分子量を有するポリオキシエチレンをベースとしたポリマー電解質とリチウムカソードとを含む〕。図1に示されている各面に、ステンレス鋼製の集電体を配置した。
ナルゲネフラスコ中に、7g(70重量%)の実施例4で得られたグラフト化炭素、1g(10重量%)のシクロヘキサンジメタノールビニルジエーテル(BASF社から市販)、2g(20重量%)のオクタデシルビニルエーテル(BASF社から市販)、および50mgの、ビス(ペルフルオロブタンスルホニル)イミドのジフェニルヨードニウム塩を導入した。20mlのアセトニトリルを加えた後、実施例5のように本混合物をジルコニアロールと共に粉砕した。
グローブボックス中で4時間経過後、フィルムに254nmの紫外線を1900mW/cm2のエネルギーにて30秒照射し、次いで媒体中で生成される化学種の増殖を可能にするためにさらに10分照射した。最終的には、アルミニウムシート上に厚さ11μmのフィルム(以後これをF1と呼ぶ)が得られた。同じ原理を使用して、シクロヘキサンジメタノールビニルジエーテル(60重量%)のマトリックス中に、実施例3において得られたようなグラフト化炭素(40重量%)のデポジットを得た。このように、アルミニウムシート上に厚さ8μmのフィルム(以後これをF2と呼ぶ)を得た。
これら3つの発電体を、実施例6の場合と類似の条件下でサイクル作動させた。これら条件下で得られたサイクル曲線を図4に示す。
1M濃度の塩化アンモニウム水溶液で構成される電解質、および70容量%の二酸化マンガンMnO2と30容量%の実施例2で得られたグラフト化炭素とで構成される複合カソードを使用して、塩類技術(saline technology)に基づいて3つのZn/MnO2電池を製造した。
特に保存時において、標準電池に比較してこれら電池の性能向上が認められ、自己放電は6ヶ月間で20%から5%になり、電池から取り出される容量は、断続的作動で25%以上増大する。
実施例3において得られたグラフト化炭素(3重量%)を、290の分子量を有するポリ−THF一ジビニルエーテル(96重量%)中に分散して得られる安定なコロイド分散系〔ビス(ペルフルオロブタンスルホニル)イミドのジ(ドデシルフェニル)ヨードニウム塩を光開始剤として含有〕を製造した。この分散系を紙の上に層状に広げ、254nmで1900mW/cm2のエネルギーの紫外線を数秒間照射した。デポジットはほぼ瞬間的に固化した。このインキを水で希釈することによって良好な結果が得られた。
実施例10
ジェファーミン(登録商標)モノアミンを分子量800のポリエチレンモノアルコール(アルドリッチから市販)で置き換えることによって、分子量800のポリエチレンでグラフトしたものと類似の炭素の存在下にて、実施例1に記載のプロセスと類似のプロセスにしたがって、ニトリルゴム(96重量%)のジクロロメタン溶液を作製した。グラフト化炭素はこの溶媒中に容易に分散した。この粘性溶液を注いで乾燥した後、ポリマー中炭素の均質な分散系が得られた。このポリマーは、10-6S.cm-1の導電率と静電防止特性を有する。
Claims (2)
- カルボキシル基、アミド基、および/またはヒドロキシル基を表面に含有する炭化物質を、前記炭化物質にグラフトさせようとする少なくとも1種のポリマーを含んだ溶液中に懸濁させること、このとき前記ポリマーが、少なくとも1つのカルボキシル基、アミン基、および/またはヒドロキシル基を含有し、前記溶液がさらに、四塩化炭素、クロロホルム、ベンゼン、トルエン、クロロベンゼン、およびテトラクロロエタンから選ばれる前記ポリマーの溶媒を含む;および
前記ポリマーの少なくとも1種をエステル結合またはアミド結合によって炭化物質にグラフトさせるよう、ある1つのカルボキシル基とアミン基および/またはヒドロキシル基との間の脱水反応を促進するような条件下で前記溶液を処理し、前記脱水反応が、炭化物質のポリマー溶液の前記溶媒中懸濁液を共沸蒸留することによって行われること;
を特徴とする、炭化物質の表面に少なくとも1種のポリマーをグラフトさせる方法。 - 請求項1に記載の方法によって得られる物質を含むインキ。
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CA002194127A CA2194127A1 (fr) | 1996-12-30 | 1996-12-30 | Anions delocalises utiles en tant que solutes electrolytiques |
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2000
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2001
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KR20140143201A (ko) * | 2012-03-28 | 2014-12-15 | 캐보트 코포레이션 | 폴리에테르아민으로 처리된 산화된 카본 블랙 및 그를 포함하는 코팅 조성물 |
JP2015512458A (ja) * | 2012-03-28 | 2015-04-27 | キャボット コーポレイションCabot Corporation | ポリエーテルアミンで処理された酸化カーボンブラックおよびそれを含むコーティング組成物 |
KR101704889B1 (ko) * | 2012-03-28 | 2017-02-08 | 캐보트 코포레이션 | 폴리에테르아민으로 처리된 산화된 카본 블랙 및 그를 포함하는 코팅 조성물 |
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