JP4070244B2 - 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
- JP4070244B2 JP4070244B2 JP52951398A JP52951398A JP4070244B2 JP 4070244 B2 JP4070244 B2 JP 4070244B2 JP 52951398 A JP52951398 A JP 52951398A JP 52951398 A JP52951398 A JP 52951398A JP 4070244 B2 JP4070244 B2 JP 4070244B2
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- JP
- Japan
- Prior art keywords
- polymer
- vinyl ether
- carbon
- power generator
- carbonized material
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
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- 239000005539 carbonized material Substances 0.000 title claims description 26
- 238000000034 method Methods 0.000 claims description 55
- 229920000642 polymer Polymers 0.000 claims description 49
- -1 polyethylene Polymers 0.000 claims description 36
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 24
- 239000000463 material Substances 0.000 claims description 20
- QYKIQEUNHZKYBP-UHFFFAOYSA-N Vinyl ether Chemical group C=COC=C QYKIQEUNHZKYBP-UHFFFAOYSA-N 0.000 claims description 18
- 239000002904 solvent Substances 0.000 claims description 17
- 239000000725 suspension Substances 0.000 claims description 17
- 230000008569 process Effects 0.000 claims description 16
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 15
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 15
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 claims description 14
- 229910052744 lithium Inorganic materials 0.000 claims description 14
- 239000000178 monomer Substances 0.000 claims description 14
- 229910052782 aluminium Inorganic materials 0.000 claims description 13
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims description 13
- 239000004698 Polyethylene Substances 0.000 claims description 11
- 150000001412 amines Chemical class 0.000 claims description 11
- 125000000524 functional group Chemical group 0.000 claims description 11
- 229920000573 polyethylene Polymers 0.000 claims description 11
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- QPFMBZIOSGYJDE-UHFFFAOYSA-N 1,1,2,2-tetrachloroethane Chemical compound ClC(Cl)C(Cl)Cl QPFMBZIOSGYJDE-UHFFFAOYSA-N 0.000 claims description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 4
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- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 claims description 4
- DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 claims description 3
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- WULAHPYSGCVQHM-UHFFFAOYSA-N 2-(2-ethenoxyethoxy)ethanol Chemical compound OCCOCCOC=C WULAHPYSGCVQHM-UHFFFAOYSA-N 0.000 claims description 2
- VUIWJRYTWUGOOF-UHFFFAOYSA-N 2-ethenoxyethanol Chemical compound OCCOC=C VUIWJRYTWUGOOF-UHFFFAOYSA-N 0.000 claims description 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 2
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- WUGQZFFCHPXWKQ-UHFFFAOYSA-N Propanolamine Chemical group NCCCO WUGQZFFCHPXWKQ-UHFFFAOYSA-N 0.000 claims description 2
- MOOIXEMFUKBQLJ-UHFFFAOYSA-N [1-(ethenoxymethyl)cyclohexyl]methanol Chemical compound C=COCC1(CO)CCCCC1 MOOIXEMFUKBQLJ-UHFFFAOYSA-N 0.000 claims description 2
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- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical group I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 claims description 2
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- 239000004800 polyvinyl chloride Substances 0.000 claims 4
- 229920000915 polyvinyl chloride Polymers 0.000 claims 4
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims 2
- 238000010438 heat treatment Methods 0.000 claims 2
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- 229910052725 zinc Inorganic materials 0.000 claims 2
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- 125000005520 diaryliodonium group Chemical group 0.000 claims 1
- 229920000098 polyolefin Polymers 0.000 claims 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 81
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- 239000000976 ink Substances 0.000 description 10
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
- 239000005518 polymer electrolyte Substances 0.000 description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 8
- 239000010408 film Substances 0.000 description 8
- 239000011159 matrix material Substances 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- 238000010992 reflux Methods 0.000 description 7
- NUJOXMJBOLGQSY-UHFFFAOYSA-N manganese dioxide Inorganic materials O=[Mn]=O NUJOXMJBOLGQSY-UHFFFAOYSA-N 0.000 description 6
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 5
- 238000010521 absorption reaction Methods 0.000 description 5
- 239000000654 additive Substances 0.000 description 5
- 238000004458 analytical method Methods 0.000 description 5
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- 239000003960 organic solvent Substances 0.000 description 5
- 238000006116 polymerization reaction Methods 0.000 description 5
- 229960000834 vinyl ether Drugs 0.000 description 5
- JPVNTYZOJCDQBK-UHFFFAOYSA-N 3-ethenoxypropan-1-amine Chemical compound NCCCOC=C JPVNTYZOJCDQBK-UHFFFAOYSA-N 0.000 description 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
- 229920000049 Carbon (fiber) Polymers 0.000 description 4
- 238000004566 IR spectroscopy Methods 0.000 description 4
- MCMNRKCIXSYSNV-UHFFFAOYSA-N Zirconium dioxide Chemical compound O=[Zr]=O MCMNRKCIXSYSNV-UHFFFAOYSA-N 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
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- 238000003756 stirring Methods 0.000 description 4
- 238000003786 synthesis reaction Methods 0.000 description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 3
- PEEHTFAAVSWFBL-UHFFFAOYSA-N Maleimide Chemical compound O=C1NC(=O)C=C1 PEEHTFAAVSWFBL-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
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- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
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- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
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- ZXMGHDIOOHOAAE-UHFFFAOYSA-N 1,1,1-trifluoro-n-(trifluoromethylsulfonyl)methanesulfonamide Chemical compound FC(F)(F)S(=O)(=O)NS(=O)(=O)C(F)(F)F ZXMGHDIOOHOAAE-UHFFFAOYSA-N 0.000 description 1
- KZJUHXVCAHXJLR-UHFFFAOYSA-N 1,1,2,2,3,3,4,4,4-nonafluoro-n-(1,1,2,2,3,3,4,4,4-nonafluorobutylsulfonyl)butane-1-sulfonamide Chemical compound FC(F)(F)C(F)(F)C(F)(F)C(F)(F)S(=O)(=O)NS(=O)(=O)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F KZJUHXVCAHXJLR-UHFFFAOYSA-N 0.000 description 1
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- XHCLAFWTIXFWPH-UHFFFAOYSA-N [O-2].[O-2].[O-2].[O-2].[O-2].[V+5].[V+5] Chemical compound [O-2].[O-2].[O-2].[O-2].[O-2].[V+5].[V+5] XHCLAFWTIXFWPH-UHFFFAOYSA-N 0.000 description 1
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- AENNXXRRACDJAY-UHFFFAOYSA-N bis(2-dodecylphenyl)iodanium Chemical class CCCCCCCCCCCCC1=CC=CC=C1[I+]C1=CC=CC=C1CCCCCCCCCCCC AENNXXRRACDJAY-UHFFFAOYSA-N 0.000 description 1
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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。
このように応用が広い範囲にわたるのは、炭化物質がもつ特異な物理化学的性質〔すなわち、耐熱性、優れた導電性、広範囲の比表面積(一般には、m2/g〜数千m2/gのオーダー)、および着色力(coloring power)〕によるものである。
炭化物質を特徴づける全ての物理化学的パラメーターのうちで最も重要なものは、最終的な分析において、炭化物質とその周囲媒体との間の界面を状態調節する炭化物質の表面状態である。したがってよく知られているように、炭化物質の表面に種々の官能基が存在していてもよいし、あるいはまた異なったプロセス〔化学的プロセス(酸化やスルホン化等)、物理化学的プロセス(電解処理やプラズマ処理等)、または熱的プロセス〕によって種々の官能基をあとで合成中に導入することができる。
このように、炭化物質の表面に、ラジカル、カルバニオン、カルボン酸、スルホン酸、ホスホン酸、ヒドロキシル、アミン、ピリジン、ハロゲン、無水物、ラクトン、ピロン、およびキノン等の種々の官能基(functions)を導入することができる。炭素表面におけるこれら異なった基の濃度は、一般には炭素1g当たり0.1〜10ミリ当量である。したがって、これら物質の表面特性(例えば、酸−塩基特性や親水−疎水特性)を制御し、最終的には表面特性を変性させることができる。この点に関しては、I.N.Ermolenko, I.P.Lyubliner,およびN.V.Gulkoによる“Chemically Modified Carbon Fibers, VCH Publishers Inc., New York, 1990”を参照のこと。このように、表面にカルボキシル官能基を有する炭素粉末は、高能力インクジェット式プリンター用顔料の分野に使用されている(デグッサAG技術情報:“Pigmentruβe/Pigment Blacks”を参照)。
炭化物質の官能化を可能にするには、多くの化学反応をその表面から開始させるようにしなければならない。界面特性を変性しようとする全ての方策のうちでは、ポリマーのグラフト化が特に重要なものである。例えば、グラフト化ポリマーの表面に種々の超微細粒子(炭素、二酸化チタン、シリカ、セライト等)が存在すると、このように変性された物質の有機溶媒中または適切なポリマーマトリックス中への分散性を改良することができる。したがって、炭素1g当たり約1gのポリスチレンを表面にグラフトすることによって、テトラヒドロフラン中において極めて安定であるような炭素ホイスカーのコロイド分散系を得ることができる(N.Tsubokawa, T.Yoshida,及びY.Soneによる“J. Polym. Sci., Part A, Polym. Chem., Vol.30, 561-567, 1992”)。
炭化物質の表面にポリマーをグラフトするために種々の合成法が使用された。2つの代表的なアプローチを挙げることができる。すなわち、炭素表面に存在する官能基からモノマーの重合を開始させるというアプローチ、および炭素表面と反応することのできる少なくとも1つの官能基(chemical function)を含むプレポリマーをグラフトさせるというアプローチである。
第一のケースにおいては、多くの研究が、ほとんどの場合、炭化物質上に存在している官能基を変性して、起こさせようとする重合のタイプに対して官能基を活性にすることによって、モノマーのアニオン重合、カチオン重合、またはラジカル重合を開始させることに重点が置かれた。例えば、炭化物質の酸化によって容易に導入できるカルボキシレート官能基からもたらされる可能性について考えてみると、アニオン重合に対してはアルカリ金属塩(リチウム塩、ナトリウム塩、カリウム塩、セシウム塩、およびルビジウム塩等)に変換し、カチオン重合に対してはアシリウム塩(過塩素酸アシリウムや六フッ化アンチモンアシリウム等)に変換し、またラジカル重合に対してはペルオキシエステルに変換する。
第二のケースにおいて、他の研究では、炭素表面に存在している基と反応することのできる官能基(a chemical function)を含んだプレポリマーのグラフト結合が検討されている(ほとんどの場合、炭素原子上に存在する基を変性して、その基を反応性にしている)。例えば、カルボキシル官能基をイソシアネート、エポキシド、または酸塩化物等に変換することによってもたらされる可能性について考えてみると、例えばポリエチレングリコール、ポリビニルアルコール、ポリエチレンイミン、シリコンジオール、およびシリコンジアミン等のグラフト結合が可能である。
これらの異なった合成プロセスは完全に満足できるものとは言えない。なぜなら、炭素原子上に固定されている基に化学的変性を施すことが必要であり、および/またはグラフト結合させようとするポリマーにより、大規模操作に対してはこうした合成が複雑でかつコスト高になるからである。さらに、グラフト結合が重合によって開始されると、その後の反応が、これら炭化物質に処理を施していく上で系の操作にとって望ましくない連鎖停止という問題を引き起こす。これらのプロセスはさらに、溶液中において形成されているポリマー鎖と炭素上のグラフト鎖とを分離する必要がある。
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。
本発明はさらに、これらの物質を、電気伝導の添加剤として(特に電気化学的発電体において)、種々の支持体(プラスチックやアルミニウム等)に対する耐食性デポジットおよび/または電気伝導体として、ならびにインキ(特にオフセットインキ)として応用することに関する。
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。
本発明の方法の新規性は、ポリマーセグメントによって変性しようとする炭素が、グラフトさせようとするポリマーを含有する溶液中において懸濁液状態になるような仕方で反応が行われる、という事実、ならびにカルボキシル官能基とアミン官能基および/またはヒドロキシル官能基との間で適切な温度で脱水反応を起こせるように溶媒が選択される、という事実による。
溶媒の中では、ジメチルホルムアミドやジメチルアセトアミドがこのタイプの反応に特に適している。これらの溶媒は多くのポリマーを溶解することができ、100〜150℃のオーダーの温度で数時間以内に反応を起こさせることができた。これとは別に、共沸蒸留を行うことのできる溶媒(例えば、クロロホルム、四塩化炭素、ベンゼン、トルエン、クロロベンゼン、またはテトラクロロエタン)を使用することもできる。これらの溶媒は、その沸点にて(すなわち、これらの4種の溶媒に対しては61〜147℃の温度にて)数時間で脱水反応を達成することができる。
官能化された炭素(functionalized carbons)のうちで、アミン官能基を有する炭素は、炭素繊維または炭素粉末を窒素含有ガス(アンモニアやアミン等)で処理することによって得られる(例えば、LoskutovとKuzinによる“Synthesis and Properties of Ion-Exchange Materials,(1968), Chmutov, K.V. ed., Moscow:Nauka, 95-101”に説明されている)。しかしながら、ヒドロキシル官能基またはカルボキシル官能基を有する炭素はより簡単に入手できる。なぜなら、酸化によって簡単に得られるし、あるいは種々のサプライヤー(キャボット社、コロンビアン・カーボン社、およびデグッサ社等)から粉末の形態で市販されているからである。デグッサ社の化合物FW200は、0.6ミリモル/gというオーダーの比較的重要な量のカルボキシル基をその表面に有しているので、こうした用途に特に適している。
少なくとも1つのアミン官能基、カルボキシル官能基、またはヒドロキシル官能基を有するポリマーのうちでは、単一の官能価を有していて炭素の表面と反応することのできるコポリマーが好ましい。こうした用途に対しては特定の系列の化合物が有用であり、ポリオキシアルキレンアミン〔Huntsmanからジェファーミン(JeffamineR)の商品名で市販されており、600〜2100g/モルの分子量を有する(Huntsman技術情報:”The JeffamineRポリオキシアルキレンアミン”を参照)、ポリオキシアルキレンモノアルコール〔例えば、ポリ(エチレングリコール)メチルエーテルやポリ(プロピレングリコール)モノブチルエーテル等〕、およびポリアルカンジオールモノアルコールが特に有用である。したがって、例えばポリオキシアルキレンモノアミン、ポリアルキレンモノアルコール、およびポリアルカンジオールモノアルコールから選ばれる親水性ポリマーを使用することができる。ポリアルカンモノアルコールから選ばれる疎水性ポリマー(例えばポリエチレンモノアルコール)も使用することができる。
特殊なクラスのモノアミンまたはモノアルコールも実用的な観点から重要である。このクラスは、ポリマーを含まないが、アミン官能基もしくはアルコール官能基とビニルエーテル官能基とを有するモノマーを含む(但し、全部または一部をポリマーと置き換えるのに使用することのできるアルキルビニルエーテルは除外する)。特に重要なモノアミンとしては3−アミノ−1−プロパノールのビニルエーテルがあり、特に重要なアルコールとしてはエチレングリコールビニルエーテル、ブタンジオールビニルエーテル、シクロヘキサンジメタノールビニルエーテル、ジエチレングリコールビニルエーテル、およびヘキサンジオールビニルエーテル(これらはBASF社から市販されている)がある。次いで、このように変性した炭素を、ビニルエーテルまたは単官能もしくは多官能のビニルアルキルエーテルで、および/または単官能もしくは多官能の不飽和モノマー(例えば、マレイミドやフマレート等)で共架橋することができ(co-crosslinked)、したがって高分子ネットワーク中に炭素を組み込むことができる。ビニルエーテルまたはアルキルビニルエーテルによる架橋は、化学線(β線を含めて)の照射下での光重合開始剤の活性化によって開始させることができる。光開始剤としては、例えば、化学線の照射下で酸を放出することのできるヨードニウム化合物、スルホニウム化合物、ホスホニウム化合物、および有機金属化合物などがある。使用できる開始剤としては、例えば、置換もしくは非置換のジアリール化合物、置換もしくは非置換のフェナシル−ジアルキルスルホニウム化合物、および置換もしくは非置換のアレーン−フェロセニウム化合物などがある。架橋はさらに、熱を加えるとラジカルを放出する(当業者にはよく知られている現象)ラジカル開始剤の存在下で行うことができ、あるいは種々の成分を薄膜(プラスチック支持体、セラミック支持体、または金属支持体上に配置することができる)に形成させた後に行うこともできる。支持体は、例えばアルミニウム、ニッケル、または銅であってもよいし、あるいはポリプロピレン、ポリエチレン、ポリエチレンテレフタレート、またはポリイミドのシートであってもよい。ビニルエーテル官能基のグラフト結合のほうが他の多くの重合可能基より高い関心を引いており、実際、カチオンタイプのメカニズムを含んだ重合は多くの利点をもたらす。特に、低温であってもモノマーの消費速度は高く、大気中の汚染物(例えば酸素)に対する感度は、ラジカル重合またはアニオン重合に比較して低い。
好ましい一般的なプロセスによれば、カルボキシル官能基を有する炭素のトルエンもしくはベンゼン中懸濁液を、アミン官能基またはヒドロキシル官能基を有する単官能ポリマーの共沸蒸留によって化学量論的に処理する。24時間還流した後、グラフトされた炭素を反応混合物の濾過によって回収し、これを乾燥する。最終的には、高純度エーテルまたは高純度エーテルと共溶媒(例えば酢酸エチル)との混合物等の溶媒中で攪拌することによって洗浄する。グラフトされた炭素がベンゼンまたはトルエンに溶解する場合、グラフト化炭素は、エーテル中での反応混合物の再沈澱、濾過、および乾燥によって回収される。
したがって、異なったポリマーセグメントでグラフトされた炭素粒子、特にジェファーミンRモノアミンM-600(≒600g/モル)、M-715、M-1000、M-2005、またはM-2070でグラフトされたFW200;ポリエチレンモノアルコールでグラフトされたFW200;ポリ(プロピレングリコール)モノブチルエーテルでグラフトされたFW200;ポリ(エチレングリコール)メチルエーテルでグラフトされたFW200;3−アミノ−1−プロパノールビニルエーテルでグラフトされたFW200;またはヘキサンジオールビニルエーテルでグラフトされたFW200が得られる。
発明者らはさらに、これら炭化物質が電気化学的発電体における電気伝導の添加剤として有用であることを示すのに成功した。実際、電気化学系は、電極内での電子とイオンの同時的な移送を確実に起こさせて、酸化還元反応(操作の初期において起こる)の生成を可能にしなければならない。
電気学的発電体だけに単純化して言えば、例えばアルカリ電池、すなわちZn/MnO2電池またはリチウム電池においては、カソード内に電気伝導体を加えることが作動のための必須条件である。この電気伝導体が電気活性物質およびバインダーと混ざり合って複合電極を形成すると、発電体は、これらの系に対して提唱されている用途に適合した出力を与えることができる。
この用途に対してしばしば使用される炭化物質はカーボンブラック(例えばシャウィニガンブラック)であり、ビーズ形態の三次元配列により、10容量%のオーダーの付加割合にて複合材料に高い導電性が確実に付与される。アクゾ社のケトジェンブラック(KetjenblackR)タイプの炭素も、複合材料中に分散させることによって複合材料に重要な導電性を付与することができる。小さな比表面積(≒20m2/g)を有するシャウィニガンブラックとは対照的に、これらの炭素は300〜600m2/gという重要な比表面積を有する。この場合は、ケトジェンブラックによって引き起こされる高い導電性が、“シェル”形態における炭素粒子の特定のモルホロジーに関連している。実際、このようなモルホロジーは、炭素粒子の重要な構造化を必要とすることなく、異なった粒子間のトンネル効果によって高い導電性をもたらすことができる。電気伝導を可能にする添加剤としてはさらに、ロンザ社(Lonza)から市販の高い比表面積を有するグラファイトがある。
これら炭化物質の製造に対して使用される技術が、確実に作動する複合材料の製造を可能にしているので、これらの炭化物質は電気化学的発電体においてその役割を果たす。こうしたことにも関わらず、これらの物質は、使用する上でまだ多くの欠点を有する。
したがって、これまで説明してきた炭素のタイプはいずれも、Sn/MnO2電池の場合にはカソード材料を炭素で被覆するために、またポリマー電解質リチウム電池の場合には、挿入物質、炭素、およびポリマーの複合混合物を均一に分散させるために、比較的高い剪断強度を有する機械的システムを使用する必要がある。さらに、炭素を加えると、例えばケトジェンブラックK600の場合、これを10容量%以下の量にて含有するポリマーマトリックスの粘度が急速に増大する。これによって一般にはカソードの外観が多孔質となり、こうしたことは、特にポリマー電解質電池においては容積エネルギー密度(density of volumic energy)に対して有害である。さらに、炭素はポリマーマトリックス中において膨脹効果を有し、このため、炭素を含有するマトリックスの押し出しが極めて困難となる。
電気化学的発電体において通常使用される炭素を充分な量の適切なポリマーでグラフトした炭素粉末で置き換えることが有利であり、これによって前記の問題点を解消できる、ということを示すことができた。
特に、ジェファーミンM-2070でグラフトしたFW200(FW200/J-2070)(大部分がポリエチレンオキシドからなる)を評価した。この物質は、有機溶媒に容易に分散可能な、光沢のある外観をもった緻密な粉末であり、こうした外観は、炭素表面がポリマーで完全に被覆されていることを示している。比較すると、ジェファーミンM-1000でグラフトしたFW200(FW200/J-1000)は光沢のない外観を有する。
先ず第一に、FW200/J-2000の緻密なパステル(pastil)の導電率を測定した。現時点では、炭素の表面を変性するとその導電率が急激に低下すると認識されている。驚くべきことに、FW200/J-2000の緻密な錠剤の導電率は≒2×10-2Ω.cm-1または≒50S-1.cmであって、この値は多くの炭素繊維が示す導電率と同等であるが、本物質は実際、わずか29容量%の炭素しか含有していない。
逆に言えば、濃度が29容量%であること、そしてFW200の比表面積が増大していること(300m2/gより高い)ことを考慮すると、このようなして得られる錠剤が均一な外観と良好な機械的挙動を有するということを認識することは驚くべきことであった。
このように、挿入物質、ポリオキシエチレン誘導体、およびFW200/J-2000〔シャウィニガンブラックを同じ容量フラクションで使用している類似のカソードとは対照的に残留多孔性(residual porosity)をもたない〕を含むポリマー電解質リチウム電池のための複合カソードを製造することができた。さらに、FW200/J-2000と挿入物質を圧密処理することによってカソードを直接製造することができた。このカソードは残留多孔性を示さなかった。これらのカソードを使用すると、シャウィニガンブラックを使用している電池と類似の性能を有するリチウム電池を製造することができた。
これらの物質は、アノード、カソード、あるいはリチウムの代わりに炭素を使用するLi-イオン電池における電気伝導の添加剤としてとしても有用である。
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。
化合物FW200/J-2000はさらに、塩類Zn/MnO2電池用として極めて有用である。実際、放電時におけるカソードの水分の減少は、これら電池の性能を制約する因子である。親水性のポリオキシエチレンセグメントが存在すれば、完全な放電時においてカソードの充分な水分の保持が可能となる。この結果、これら一次電池のより良好な作動が得られる。
さらに、ポリオキシエチレン鎖でグラフトされた炭素は、分散性が良好であるために、また水性媒体中の顔料として得られるコロイド懸濁液が安定であるために高い関心を呼んでいる。
アルキル鎖でグラフトされた炭素は、ニトリルゴムのような極性の低いポリマー中への添加剤として特に有用である。
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へ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。
使用されるプロセスは多種多様であり、異なったポリマーまたは官能基を有するグラフト化炭素を得ることができる。このように、例えば、一部がジェファーミンM-2000で、そして一部が3−アミノ−1−プロパノールビニルエーテルでグラフトされたFW200を得ることができ、したがって最終的な分析において、反応性溶媒または適切なポリマーマトリックスによる炭素の共架橋が可能となる。
さらに、このプロセスの利点は、鎖中に種々の官能性(例えば、レドックス対、非局在化アニオン、金属カチオンと錯体を形成する分子、および光学的特性を有する分子)を組み込んだポリマーのグラフトにも適用されることは言うまでもない。
下記に実施例を挙げて、本発明の実施手順および応用について例示する。本発明がこれらの実施例によって限定されることはなく、また当業者にとっては、本発明の範囲を逸脱することなく種々の変形が可能である。
【図面の簡単な説明】
図1は、本発明によるグラフト化炭素を組み込んだ電気化学的発電体を示している。
図2は、図1の発電体を使用して得られるサイクル曲線である。
図3は、本発明による他のタイプのグラフト化炭素を組み込んだ電気化学的発電体を示している。
図4は、図3の発電体を使用して得られるサイクル曲線である。
実施例1
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RM-1000(J-1000、ハンツマン社から市販)〕を加えた。ジェファーミンRの分子量は塩酸滴定によって測定した。ジェファーミンR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Rのオリーブ形状物(olive)で攪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。20時間の還流後、捕集した水の量は約2.1ml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。
繰り返し反射を利用する赤外線分光法によって得られる物質の分析により、アミドに典型的な吸収バンドの存在と、カルボキシル基に関係するバンドの消失(グラフト化されていない酸化炭素の対照スペクトルとの比較でわかる)が確認された。一方、グラフト化炭素の微量分析により、理論的な結果との良好な一致が得られた(表1)。
このグラフト化炭素は40重量%のポリマーを含有し、有機溶媒や水中に容易に分散するが、分散液の攪拌を停止すると、数分後に炭素のデカンティングが観察される。
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RM-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RM-2070で被覆されていることを示している。
繰り返し反射を利用する赤外線分光法により、アミド結合でジェファーミンRM-2070がグラフトしていることが確認された。グラフト化炭素の微量分析の結果により、この物質に対して予測される理論的結果が確認された。
このグラフト化炭素は58重量%のポリマーを含有し、有機溶媒や水中に容易に分散する。得られる分散液は、時間が経過しても安定である。したがって、つけペンやボールペンに有用な水性媒体中インキを得ることができる。
実施例3
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Rのオリーブ形状物で攪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2.1ml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。
繰り返し反射を利用する赤外線分光法によって得られる物質の分析により、アミドに典型的な吸収バンドの存在とビニルエーテルに典型的な吸収バンドの存在が確認され、そしてグラフト化されていない酸化炭素の対照スペクトルとの比較により、カルボキシル基に関係するバンドの消失が観察された。
このグラフト化炭素は、単官能もしくは多官能のビニルエーテルおよび/または不飽和モノマー(マレイミドやフマレート等)と共架橋させることができ、したがって高分子ネットワーク中への炭素の組み込みが可能となる。
実施例4
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RM-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。
繰り返し反射を利用する赤外線分光法によって得られる物質の分析により、アミドに典型的な吸収バンドの存在とビニルエーテルに典型的な吸収バンドの存在が確認され、そしてグラフト化されていない酸化炭素の対照スペクトルとの比較により、カルボキシル基に関係するバンドの消失が確認された。
この物質は、ジェファーミンRM-2070のグラフト化ポリマーセグメントを充分な量(50重量%)にて含有し、これによって炭素の分散が容易となり、安定な懸濁液が得られ、そして単官能もしくは多官能のビニルエーテルおよび/または不飽和モノマー(マレイミドやフマレート等)と炭素との共架橋が可能となるので特に有用である。
実施例5
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。
こうした結果から、特に、ポリマー電解質リチウム電池の電極用の複合材料を製造するのに、本発明のグラフト化炭素が重要であることが確認される。
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。
発電体を大気から保護するのを可能にする、そしてまたフィルムの機械的歪みをはたらかせることを可能にするパステル電池ケーシング中に、上記の集成体を密閉した。この電池を、60℃の乾燥器中に置かれたアルゴン雰囲気下のエンクロージャー中に配置した。次いで、C/10(10時間で充電または放電される公称容量)の充電−放電速度にて、1.8Vと3.3Vの間でサイクルさせた。これらの条件下で得られるサイクル曲線を図2に示す。
この電池はサイクル作動において極めて優れた性能を示し、600サイクル後でも、10サイクルでの容量の70%以上の放電容量がある。こうした結果から、ポリマー電解質リチウム電池用に本発明のグラフト化炭素が重要であることが確認される。
実施例7
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。
24時間後、得られた懸濁液を、あらかじめ清浄にした厚さ20μmのアルミニウムシート上に配置されたガラスリング中の、アルゴン雰囲気のグローブボックス中に注ぎ込んだ。
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。
二酸化バナジウム(45重量%)、シャウィニガンブラック(5容量%)、およびポリエチレンオキシド(50重量%)をベースとする複合カソードを使用して、第1の電気化学的発電体を製造した。得られた懸濁液から、実施例5の場合と類似の条件下でフィルムを製造した。減圧で72時間乾燥した後、実施例5の場合と同じ手順にしたがって発電体を組み立てた。但しこのとき、本実施例の複合物をカソードとして使用し、炭素/ポリマーのデポジット(F1)で被覆されたアルミニウムシートを集電体として使用した。
同じ手順にしたがって〔但し、炭素/ポリマーのデポジット(F2)で被覆されたアルミニウムシートを集電体として使用〕、第2の電気化学的発電体を製造した。図3を参照。
比較のため、同じ手順にしたがって、あらかじめ清浄にしておいたアルミニウムのブランクシートを使用することによって第3の電気化学的発電体を製造した。
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。
本実施例において完全に例示されているように、本発明のグラフト化炭素は、特にポリマー電解質リチウム電池の集電体用の耐食性デポジットを製造するのに適している。ポリエチレンセグメントを含まない炭素デポジットでも、この用途に対しては良好な性能を示す。なぜなら、使用されるマトリックスの極性が低く、また非溶媒和特性をもつために、アルミニウム集電気体に対する腐食をより充分に保護するからである。
実施例8
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。
第1の発電体をC/10の放電速度で放電した。第2の発電体をC/10の速度で1時間断続的に放電し、次いで24時間休止し、これを繰り返した。第3の発電体は保存した。
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9
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−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。
このようなインキ組成物は、プロセス中に有機溶媒が存在しないので、オフセット印刷に対して特に有用である。さらに、重合速度も適切である。
実施例10
ジェファーミンR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。
当業者にとっては、請求の範囲に規定の本発明の範囲を逸脱することなく、種々の変形が可能であることは言うまでもない。
Claims (36)
- 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。 - 前記脱水反応が加熱することによって行われることを特徴とする、請求項1記載の方法。
- 前記加熱が60〜150℃の温度で行われることを特徴とする、請求項2記載の方法。
- 前記共沸蒸留が前記溶媒の沸点以下の温度で行われることを特徴とする、請求項1記載の方法。
- 前記ポリマーが単一の官能基を有することを特徴とする、請求項1記載の方法。
- 前記ポリマーが、ポリオキシアルキレンモノアミン、ポリオキシアルキレンアルコール、およびポリアルカンジオールから選ばれる親水性ポリマーであることを特徴とする、請求項1記載の方法。
- 前記ポリマーが、ポリアルケンモノアルコールから選ばれる疎水性ポリマーであることを特徴とする、請求項5記載の方法。
- 前記ポリマーが、ポリオキシアルキレンアミン、ポリ(エチレングリコール)メチルエーテル、およびポリ(プロピレングリコール)モノブチルエーテルから選ばれることを特徴とする、請求項6記載の方法。
- 前記ポリマーがポリエチレンモノアルコールから選ばれることを特徴とする、請求項7記載の方法。
- 前記ポリマーを、アミン官能基もしくはアルコール官能基と、ビニルエーテル官能基もしくはアルキルビニルエーテル官能基とを含んだモノマーで置き換えることを特徴とする、請求項1記載の方法。
- 前記ポリマーの一部を、アミン官能基もしくはアルコール官能基と、ビニルエーテル官能基もしくはアルキルビニルエーテル官能基とを含んだモノマーで置き換えることを特徴とする、請求項1記載の方法。
- 前記モノマーが、3−アミノ−1−プロパノール、エチレングリコールビニルエーテル、ブタンジオールビニルエーテル、シクロヘキサンジメタノールビニルエーテル、ジエチレングリコールビニルエーテル、およびヘキサンジオールビニルエーテルから選ばれることを特徴とする、請求項10または11に記載の方法。
- 得られたモノマーグラフト炭化物質を、単官能または多官能のビニルエーテルもしくはアルキルビニルエーテルで架橋することを特徴とする、請求項10または11に記載の方法。
- 得られたモノマーグラフト炭化物質を、単官能または多官能のビニルエーテルもしくはアルキルビニルエーテル、および単官能または多官能の不飽和モノマーで架橋することを特徴とする、請求項10または11に記載の方法。
- ビニルエーテルもしくはアルキルビニルエーテルによる架橋が、β線を含む化学線の照射による光重合開始剤の活性化によって開始されることを特徴とする、請求項13記載の方法。
- 前記光開始剤が、化学線の作用によって酸を生成させることのできるヨードニウム化合物、スルホニウム化合物、ホスホニウム化合物、および有機金属化合物からなる群から選ばれることを特徴とする、請求項15記載の方法。
- 前記光開始剤が、置換または非置換のジアリールヨードニウム化合物、置換または非置換のフェナンシル−ジアルキルスルホニウム化合物、および置換または非置換のアレーン−フェロセニウム化合物から選ばれることを特徴とする、請求項16記載の方法。
- 前記架橋が、熱の作用によってラジカルを生成するラジカル開始剤の存在下で行われることを特徴とする、請求項14記載の方法。
- 前記架橋が、種々の構成成分を薄膜の形態で供給した後に行われることを特徴とする、請求項13〜18のいずれか1項に記載の方法。
- 前記薄膜がプラスチック支持体、セラミック支持体、または金属支持体上に配置されることを特徴とする、請求項19記載の方法。
- 前記支持体がアルミニウム、ニッケル、亜鉛、リチウム、または銅を含むことを特徴とする、請求項20記載の方法。
- 前記支持体が、ポリプロピレン、ポリエチレン、ポリエチレンテレフタレート、ポリイミド、ポリアクリロニトリル、ポリ塩化ビニル、ポリエステル、ポリエーテル、ナイロン、ポリ酢酸ビニル、ポリスチレン、メチルポリメタクリレート、ポリブタジエン、ポリイソプレン、またはポリアミドのシートであることを特徴とする、請求項20記載の方法。
- 前記炭化物質がカーボンブラックであることを特徴とする、請求項1記載の方法。
- 前記ポリマーがそのポリマー鎖中に他の官能基を含むことを特徴とする、請求項1記載の方法。
- 前記他の官能基が、レドックス対、非局在化アニオン、金属カチオンと錯体を形成する分子、および光学的特性を有する分子から選ばれることを特徴とする、請求項1記載の方法。
- 前記溶液がさらに、アミン官能基またはアルコール官能基を含有するモノマーを含むことを特徴とする、請求項1記載の方法。
- アノードおよび/またはカソードが、請求項1〜26のいずれか1項に記載の方法によって得られた物質を含むことを特徴とする、アノード、カソード、および電解質からなる電気化学的発電体。
- Li−ポリマータイプまたはLi−イオンタイプであることを特徴とする、請求項27記載の電気化学的発電体。
- 前記物質が請求項6および9〜26のいずれか1項に記載の方法によって得られることを特徴とする、請求項28記載の電気化学的発電体。
- 請求項21に記載の方法により得られる支持体を含む集電体を使用することを特徴とする、請求項29記載の電気化学的発電体。
- 亜鉛を含む一次発電体であることを特徴とする、請求項27記載の電気化学的発電体。
- 前記物質が請求項6および9〜26のいずれか1項に記載の方法によって得られることを特徴とする、請求項31記載の電気化学的発電体。
- 請求項21に記載の方法により得られる支持体を含む少なくとも1つの集電体を使用することを特徴とする、請求項31記載の電気化学的発電体。
- 請求項22記載の方法により得られる、ポリプロピレン、ポリエチレン、ポリエチレンテレフタレート、ポリイミド、ポリアクリロニトリル、ポリ塩化ビニル、ポリエステル、ポリエーテル、ナイロン、ポリ酢酸ビニル、ポリスチレン、メチルポリメタクリレート、ポリブタジエン、ポリイソプレン、またはポリアミドのシートである軟質支持体上における、フレキシブルな電気接点としての導体デポジットの使用方法。
- 請求項22記載の方法により得られる、ポリプロピレン、ポリエチレン、ポリエチレンテレフタレート、ポリイミド、ポリアクリロニトリル、ポリ塩化ビニル、ポリエステル、ポリエーテル、ナイロン、ポリ酢酸ビニル、ポリスチレン、メチルポリメタクリレート、ポリブタジエン、ポリイソプレン、またはポリアミドのシートである軟質支持体上における、電磁気に対する保護物としての導体デポジットの使用方法。
- 請求項22記載の方法により得られる、ポリプロピレン、ポリエチレン、ポリエチレンテレフタレート、ポリイミド、ポリアクリロニトリル、ポリ塩化ビニル、ポリエステル、ポリエーテル、ナイロン、ポリ酢酸ビニル、ポリスチレン、メチルポリメタクリレート、ポリブタジエン、ポリイソプレン、またはポリアミドのシートである軟質支持体上における、帯電防止用保護物としての導体デポジットの使用方法。
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JP52951898A Expired - Lifetime JP4823401B2 (ja) | 1996-12-30 | 1997-12-30 | 過フッ化アミド塩及びイオン伝導物質としてのその使用方法 |
JP52951498A Expired - Lifetime JP4124487B2 (ja) | 1996-12-30 | 1997-12-30 | 五員環アニオン塩又はテトラアザペンタレン誘導体と、イオン伝導性物質としてのそれらの使用 |
JP52951398A Expired - Lifetime JP4070244B2 (ja) | 1996-12-30 | 1997-12-30 | 表面変性された炭化物質 |
JP52951798A Expired - Lifetime JP4361137B2 (ja) | 1996-12-30 | 1997-12-30 | 液体形態のプロトン伝導体 |
JP52951598A Pending JP2000508677A (ja) | 1996-12-30 | 1997-12-30 | マロン酸ニトリル誘導体アニオン塩、及びイオン伝導性材料としてのそれらの使用 |
JP52951698A Expired - Lifetime JP4683675B2 (ja) | 1996-12-30 | 1997-12-30 | 複素環式芳香族アニオン塩及びイオン性導電材料としてのその使用 |
JP2007193021A Pending JP2008007781A (ja) | 1996-12-30 | 2007-07-25 | 表面変性された炭化物質 |
JP2008143090A Pending JP2009004374A (ja) | 1996-12-30 | 2008-05-30 | 液体形態のプロトン伝導体 |
JP2009010733A Expired - Lifetime JP4927108B2 (ja) | 1996-12-30 | 2009-01-21 | 複素環式芳香族アニオン塩及びイオン性導電材料としてのその使用 |
JP2009120239A Expired - Lifetime JP5629061B2 (ja) | 1996-12-30 | 2009-05-18 | 過フッ化アミド塩及びイオン伝導物質としてのその使用方法 |
JP2010006864A Expired - Lifetime JP5209649B2 (ja) | 1996-12-30 | 2010-01-15 | マロン酸ニトリル誘導体アニオン塩、及びイオン伝導性材料としてのそれらの使用 |
JP2013033109A Pending JP2013173740A (ja) | 1996-12-30 | 2013-02-22 | 過フッ化アミド塩及びイオン伝導物質としてのその使用方法 |
JP2014001687A Withdrawn JP2014169271A (ja) | 1996-12-30 | 2014-01-08 | 過フッ化アミド塩及びイオン伝導物質としてのその使用方法 |
JP2015234934A Pending JP2016104739A (ja) | 1996-12-30 | 2015-12-01 | 過フッ化アミド塩及びイオン伝導物質としてのその使用方法 |
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JP52951498A Expired - Lifetime JP4124487B2 (ja) | 1996-12-30 | 1997-12-30 | 五員環アニオン塩又はテトラアザペンタレン誘導体と、イオン伝導性物質としてのそれらの使用 |
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JP52951798A Expired - Lifetime JP4361137B2 (ja) | 1996-12-30 | 1997-12-30 | 液体形態のプロトン伝導体 |
JP52951598A Pending JP2000508677A (ja) | 1996-12-30 | 1997-12-30 | マロン酸ニトリル誘導体アニオン塩、及びイオン伝導性材料としてのそれらの使用 |
JP52951698A Expired - Lifetime JP4683675B2 (ja) | 1996-12-30 | 1997-12-30 | 複素環式芳香族アニオン塩及びイオン性導電材料としてのその使用 |
JP2007193021A Pending JP2008007781A (ja) | 1996-12-30 | 2007-07-25 | 表面変性された炭化物質 |
JP2008143090A Pending JP2009004374A (ja) | 1996-12-30 | 2008-05-30 | 液体形態のプロトン伝導体 |
JP2009010733A Expired - Lifetime JP4927108B2 (ja) | 1996-12-30 | 2009-01-21 | 複素環式芳香族アニオン塩及びイオン性導電材料としてのその使用 |
JP2009120239A Expired - Lifetime JP5629061B2 (ja) | 1996-12-30 | 2009-05-18 | 過フッ化アミド塩及びイオン伝導物質としてのその使用方法 |
JP2010006864A Expired - Lifetime JP5209649B2 (ja) | 1996-12-30 | 2010-01-15 | マロン酸ニトリル誘導体アニオン塩、及びイオン伝導性材料としてのそれらの使用 |
JP2013033109A Pending JP2013173740A (ja) | 1996-12-30 | 2013-02-22 | 過フッ化アミド塩及びイオン伝導物質としてのその使用方法 |
JP2014001687A Withdrawn JP2014169271A (ja) | 1996-12-30 | 2014-01-08 | 過フッ化アミド塩及びイオン伝導物質としてのその使用方法 |
JP2015234934A Pending JP2016104739A (ja) | 1996-12-30 | 2015-12-01 | 過フッ化アミド塩及びイオン伝導物質としてのその使用方法 |
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US (16) | US6319428B1 (ja) |
EP (9) | EP0850933A1 (ja) |
JP (14) | JP4823401B2 (ja) |
CA (9) | CA2704986C (ja) |
DE (6) | DE69739501D1 (ja) |
WO (6) | WO1998029358A2 (ja) |
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CA2704986C (fr) * | 1996-12-30 | 2013-04-09 | Hydro-Quebec | Utilisation d'un compose ionique derive du malononitrile comme photoinitiateur, amorceur radicalaire ou catalyseur dans les procedes de polymerisation, ou comme colorant cationique |
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