JP2010518239A - ハイブリッド材料及びその製造方法 - Google Patents
ハイブリッド材料及びその製造方法 Download PDFInfo
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- JP2010518239A JP2010518239A JP2009549443A JP2009549443A JP2010518239A JP 2010518239 A JP2010518239 A JP 2010518239A JP 2009549443 A JP2009549443 A JP 2009549443A JP 2009549443 A JP2009549443 A JP 2009549443A JP 2010518239 A JP2010518239 A JP 2010518239A
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- PKFHRDQMVBGXGO-UHFFFAOYSA-N 2,4-dinitro-n-(3-triethoxysilylpropyl)aniline Chemical compound CCO[Si](OCC)(OCC)CCCNC1=CC=C([N+]([O-])=O)C=C1[N+]([O-])=O PKFHRDQMVBGXGO-UHFFFAOYSA-N 0.000 claims description 4
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Classifications
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
- B01J31/12—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides containing organo-metallic compounds or metal hydrides
- B01J31/123—Organometallic polymers, e.g. comprising C-Si bonds in the main chain or in subunits grafted to the main chain
- B01J31/124—Silicones or siloxanes or comprising such units
- B01J31/125—Cyclic siloxanes
-
- C—CHEMISTRY; METALLURGY
- C04—CEMENTS; CONCRETE; ARTIFICIAL STONE; CERAMICS; REFRACTORIES
- C04B—LIME, MAGNESIA; SLAG; CEMENTS; COMPOSITIONS THEREOF, e.g. MORTARS, CONCRETE OR LIKE BUILDING MATERIALS; ARTIFICIAL STONE; CERAMICS; REFRACTORIES; TREATMENT OF NATURAL STONE
- C04B35/00—Shaped ceramic products characterised by their composition; Ceramics compositions; Processing powders of inorganic compounds preparatory to the manufacturing of ceramic products
- C04B35/622—Forming processes; Processing powders of inorganic compounds preparatory to the manufacturing of ceramic products
- C04B35/624—Sol-gel processing
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D53/00—Separation of gases or vapours; Recovering vapours of volatile solvents from gases; Chemical or biological purification of waste gases, e.g. engine exhaust gases, smoke, fumes, flue gases, aerosols
- B01D53/34—Chemical or biological purification of waste gases
- B01D53/46—Removing components of defined structure
- B01D53/72—Organic compounds not provided for in groups B01D53/48 - B01D53/70, e.g. hydrocarbons
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D53/00—Separation of gases or vapours; Recovering vapours of volatile solvents from gases; Chemical or biological purification of waste gases, e.g. engine exhaust gases, smoke, fumes, flue gases, aerosols
- B01D53/34—Chemical or biological purification of waste gases
- B01D53/74—General processes for purification of waste gases; Apparatus or devices specially adapted therefor
- B01D53/81—Solid phase processes
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Abstract
Description
(a)前記セルラーモノリスが、4μm〜50μmの平均寸法dAを有するマクロ孔、20〜30Åの平均寸法dEを有するメソ孔及び5〜10Åの平均寸法dIを有するミクロ孔を有し、これらの孔が互いにつながっている(連続孔である)こと;
(b)前記の無機酸化物のポリマーが式−(CH2)n−R1に相当する有機基Rを有し、ここで、0≦n≦5であり、且つR1が
・チオール基、
・ピロリル基C4H3N−(これは、窒素によって−(CH2)n−に結合する)、
・アミノ基(これは、随意に置換されたアルキル、アルキルアミノ若しくはアリール置換基を1個以上有することができる)、
・アルキル基(好ましくは1〜5個の炭素原子を有するもの)、又は
・フェニル基(これは、アルキル置換基、特にメチル基を有することができる)
を表わすこと:
を特徴とする。
・3−メルカプトプロピル基;
・3−アミノプロピル基;
・3−ピロリルプロピル基;
・N−(2−アミノエチル)−3−アミノプロピル基;
・3−(2,4−ジニトロフェニルアミノ)プロピル基;
・フェニル若しくはベンジル基;又は
・メチル基:
であることができる。
(3−メルカプトプロピル)トリメトキシシラン、
(3−アミノプロピル)トリエトキシシラン、
N−(3−トリメトキシシリルプロピル)ピロール、
3−(2,4−ジニトロフェニルアミノ)プロピルトリエトキシシラン、
N−(2−アミノエチル)−3−アミノプロピルトリメトキシシラン、
フェニルトリエトキシシラン、及び
メチルトリエトキシシラン。
・メチル−SiO−1aモノリス(写真3b及び図3g)並びにメルカプト−SiO−1aモノリス(写真3e及び図3j)については、メソ孔が統計学的態様で分散した;
・ピロール−SiO−1a、DNP−アミノ−SiO−1a及びベンジル−SiO−2aモノリスにおいては、メソ孔が六角形態様で組織化された;
・g−アミノ−SiO及びg−メルカプト−SiOモノリスにおいては、メソ孔が10〜6000nmの範囲で多分散分布を有し、g−アミノ−SiOについては150nm及び700nmを中心とする2つの大きいピークがあり、そしてg−メルカプト−SiOについては60nm及び4000nmを中心とする2つの大きいピークがあった。
・Pd@g−アミノ−SiO(0.11g):四角□で示したカーブ;
・Pd@g−メルカプト−SiO(0.11g):黒丸●で示したカーブ;
・Pd@メルカプト−SiO(0.11g):三角Δで示したカーブ;
・Pd@−アミノ−SiO(0.055g):丸○で示したカーブ。この触媒の調製については、0.11gではなくて0.055gの担体を用いた。これは、同じ触媒を半分の量で用いたものである。
Claims (26)
- 無機酸化物のポリマーから成る固体状セルラーモノリスの形の材料であって、
前記セルラーモノリスが、4μm〜50μmの平均寸法dAを有するマクロ孔、20〜30Åの平均寸法dEを有するメソ孔及び5〜10Åの平均寸法dIを有するミクロ孔を有し、これらの孔が互いにつながっていること;
前記の無機酸化物のポリマーが式−(CH2)n−R1に相当する有機基Rを有し、ここで、0≦n≦5であり、且つR1がチオール基、ピロリル基、アルキル基、アミノ基(これは、置換されていてよいアルキル、アルキルアミノ若しくはアリール置換基を1個以上有することができる)又はフェニル基(これは、アルキル置換基を有することができる)を表わすこと:
を特徴とする、前記材料。 - 前記無機酸化物が1種以上の元素の酸化物であって、これらの元素の内の少なくとも1種がアルコキシドを形成することができるタイプのものであることを特徴とする、請求項1に記載の材料。
- 前記の元素の内の少なくとも1種がSi、Ti、Zr、Th、Nb、Ta、V、W及びAlから選択されることを特徴とする、請求項2に記載の材料。
- 前記酸化物がB及びSnを追加的に含有する混合酸化物であることを特徴とする、請求項2又は3に記載の材料。
- 前記無機ポリマーがケイ素酸化物又はケイ素の混合酸化物のポリマーであることを特徴とする、請求項1〜4のいずれかに記載の材料。
- R1が1〜5個の炭素原子を有するアルキル基であることを特徴とする、請求項1に記載の材料。
- 前記無機酸化物ポリマーが単一のタイプのR基を有することを特徴とする、請求項1に記載の材料。
- 前記無機酸化物ポリマーが少なくとも2つの異なるタイプのR基を有することを特徴とする、請求項1に記載の材料。
- 前記有機基Rが3−メルカプトプロピル基、3−アミノプロピル基、3−ピロリルプロピル基、N−(2−アミノエチル)−3−アミノプロピル基、3−(2,4−ジニトロフェニルアミノ)プロピル基、フェニル基、ベンジル基又はメチル基であることを特徴とする、請求項1〜8のいずれかに記載の材料。
- 請求項1に記載の材料の製造方法であって、
界面活性剤の水溶液に油性相を添加することによってエマルションを調製し、
前記エマルションを調製する前又は調製した後に、前記界面活性剤水溶液に前記無機酸化物ポリマーのテトラアルコキシド(TAM)前駆体少なくとも1種を添加し、
前記前駆体が縮合するまでこの反応混合物を放置し、
次いでこの混合物を乾燥させてモノリスを得る
ことを含み、有機基Rを有する前駆体アルコキシド(AMR化合物)少なくとも1種を添加することを特徴とする、前記方法。 - 前記油性相を添加する前に前記アルコキシドAMRを前記界面活性剤水溶液に導入することを特徴とする、請求項10に記載の方法。
- 前記アルコキシドAMRを前記油性相に導入し、次いでこれをTAM水溶液に添加してエマルションを形成させることを特徴とする、請求項10に記載の方法。
- 前記界面活性剤水溶液及びTAMから乾燥後に得られた無機モノリスにAMRの溶液を含浸させることを特徴とする、請求項10に記載の方法。
- 前記乾燥工程の終わりに得られるハイブリッドモノリスを熱処理に付すことを特徴とする、請求項11又は12に記載の方法。
- (アルコキシドAMR/テトラアルコキシドTAM)の質量比を20/80より小さくすることを特徴とする、請求項10〜14のいずれかに記載の方法。
- テトラアルコキシドTAMがケイ素のテトラアルコキシドであることを特徴とする、請求項10〜15のいずれかに記載の方法。
- 前記テトラアルコキシドTAMがテトラメトキシシラン又はテトラエトキシシランであることを特徴とする、請求項16に記載の方法。
- 前記アルコキシドAMRが
(3−メルカプトプロピル)トリメトキシシラン、
(3−アミノプロピル)トリエトキシシラン、
N−(3−トリメトキシシリルプロピル)ピロール、
3−(2,4−ジニトロフェニルアミノ)プロピルトリエトキシシラン、
N−(2−アミノエチル)−3−アミノプロピルトリメトキシシラン、
フェニルトリエトキシシラン、及び
メチルトリエトキシシラン
から選択されるトリアルコキシシランであることを特徴とする、請求項10〜17のいずれかに記載の方法。 - 前記油性相がドデカン又はシリコーン油から選択されることを特徴とする、請求項10〜18のいずれかに記載の方法。
- 前記界面活性剤化合物がカチオン性界面活性剤であり、且つ反応媒体を3より小さいpHにすることを特徴とする、請求項10〜19のいずれかに記載の方法。
- 前記界面活性剤化合物がアニオン性界面活性剤であり、且つ反応媒体を10より大きいpHにすることを特徴とする、請求項10〜19のいずれかに記載の方法。
- 前記界面活性剤化合物が非イオン性界面活性剤であり、且つ反応媒体を10より大きいpH又は3より小さいpHにすることを特徴とする、請求項10〜19のいずれかに記載の方法。
- 液体又は気体状媒体中に含有されるベンゼン、トルエン又はキシレンを除去するための、請求項1〜9のいずれかに記載の材料の使用。
- 担体及び金属触媒から成る触媒系であって、前記担体が請求項1〜9のいずれかに記載の材料であることを特徴とする、前記触媒系。
- 前記金属触媒がナノ粒子の形にあることを特徴とする、請求項24に記載の触媒系。
- 溝呂木−ヘック反応又は鈴木−宮浦反応に従ってビフェニル化合物を生成させるための炭素−炭素カップリング反応を触媒するための、請求項24に記載の触媒系の使用。
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JP2011527327A (ja) * | 2008-07-11 | 2011-10-27 | コミサリア ア レネルジー アトミック エ オ ゼネルジー アルテルナティブ | 単環式芳香族化合物およびその他の汚染物質のナノ多孔質検出器 |
JP2013544743A (ja) * | 2010-10-11 | 2013-12-19 | サントル ナスィオナル ド ラ ルシェルシュ スィアンティフィク | 泡状無機モノリシック材料を製造する方法、及び該材料の使用 |
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US8945804B2 (en) * | 2008-07-09 | 2015-02-03 | Cabot Corporation | Treated metal oxide particles and toner compositions |
FR2947564B1 (fr) | 2009-07-06 | 2011-07-22 | Univ Paris Curie | Catalyseur enzymatique heterogene, procede de preparation et utilisation |
FR2955429B1 (fr) | 2010-01-20 | 2012-03-02 | Centre Nat Rech Scient | Modifications enzymatiques d'un carbone monolithique alveolaire et applications |
FR3015476B1 (fr) | 2013-12-20 | 2016-02-12 | Commissariat Energie Atomique | Materiaux monolithiques inorganiques alveolaires echangeurs cationiques, leur procede de preparation, et procede de separation les mettant en œuvre. |
FR3037583B1 (fr) * | 2015-06-17 | 2020-01-03 | Commissariat A L'energie Atomique Et Aux Energies Alternatives | Materiaux monolithiques inorganiques alveolaires echangeurs cationiques, leur procede de preparation, et procede de separation les mettant en œuvre. |
CN106825549A (zh) * | 2017-04-13 | 2017-06-13 | 江苏金奕达铜业股份有限公司 | 一种具有大表面积结构的铜粒 |
Citations (9)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPH10182260A (ja) * | 1996-12-26 | 1998-07-07 | Naohiro Soga | 無機系多孔質体の製造方法 |
JP2002102698A (ja) * | 2000-09-27 | 2002-04-09 | Toyota Central Res & Dev Lab Inc | 金属細線触媒 |
JP2003001106A (ja) * | 2001-06-22 | 2003-01-07 | Nippon Steel Corp | ガス選択吸着材料及びガス検知システム |
WO2003002458A1 (fr) * | 2001-06-29 | 2003-01-09 | Japan Science And Technology Corporation | Procede de preparation d'une matiere inorganique poreuse |
JP2005290032A (ja) * | 2004-03-31 | 2005-10-20 | Kazuki Nakanishi | 長距離秩序を有するメソ孔を含む階層的多孔質体の製造方法 |
JP2005290033A (ja) * | 2004-03-31 | 2005-10-20 | Kazuki Nakanishi | 有機無機ハイブリッド系多孔質体の製造方法 |
WO2006019988A1 (en) * | 2004-07-30 | 2006-02-23 | Waters Investments Limited | Porous inorganic/organic hybrid materials with ordered domains for chromatographic separations and processes for their preparation |
JP2007516821A (ja) * | 2003-11-06 | 2007-06-28 | メルク パテント ゲゼルシャフト ミット ベシュレンクテル ハフトング | モノリシック成形品の製造方法 |
JP2007523331A (ja) * | 2004-02-17 | 2007-08-16 | ウオーターズ・インベストメンツ・リミテツド | 有機基を表面から除去した多孔質ハイブリッドモノリス材料 |
Family Cites Families (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR2852947B1 (fr) * | 2003-03-27 | 2005-06-03 | Centre Nat Rech Scient | Materiau inorganique a structure hierarchisee, et procede pour sa preparation |
CN1880277A (zh) * | 2005-06-13 | 2006-12-20 | 中国科学院福建物质结构研究所 | 一种纳米结构玻璃陶瓷及其溶胶-凝胶制备方法 |
CN100398492C (zh) * | 2005-08-01 | 2008-07-02 | 中国人民解放军国防科学技术大学 | 一种气凝胶绝热复合材料及其制备方法 |
-
2007
- 2007-02-14 FR FR0701077A patent/FR2912400B1/fr not_active Expired - Fee Related
-
2008
- 2008-02-14 US US12/527,161 patent/US20210316288A1/en not_active Abandoned
- 2008-02-14 CA CA002677958A patent/CA2677958A1/fr not_active Abandoned
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- 2008-02-14 JP JP2009549443A patent/JP2010518239A/ja active Pending
- 2008-02-14 EP EP08775553A patent/EP2117709A2/fr not_active Withdrawn
Patent Citations (10)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPH10182260A (ja) * | 1996-12-26 | 1998-07-07 | Naohiro Soga | 無機系多孔質体の製造方法 |
JP2002102698A (ja) * | 2000-09-27 | 2002-04-09 | Toyota Central Res & Dev Lab Inc | 金属細線触媒 |
JP2003001106A (ja) * | 2001-06-22 | 2003-01-07 | Nippon Steel Corp | ガス選択吸着材料及びガス検知システム |
WO2003002458A1 (fr) * | 2001-06-29 | 2003-01-09 | Japan Science And Technology Corporation | Procede de preparation d'une matiere inorganique poreuse |
JP2007516821A (ja) * | 2003-11-06 | 2007-06-28 | メルク パテント ゲゼルシャフト ミット ベシュレンクテル ハフトング | モノリシック成形品の製造方法 |
JP2007523331A (ja) * | 2004-02-17 | 2007-08-16 | ウオーターズ・インベストメンツ・リミテツド | 有機基を表面から除去した多孔質ハイブリッドモノリス材料 |
JP2005290032A (ja) * | 2004-03-31 | 2005-10-20 | Kazuki Nakanishi | 長距離秩序を有するメソ孔を含む階層的多孔質体の製造方法 |
JP2005290033A (ja) * | 2004-03-31 | 2005-10-20 | Kazuki Nakanishi | 有機無機ハイブリッド系多孔質体の製造方法 |
WO2006019988A1 (en) * | 2004-07-30 | 2006-02-23 | Waters Investments Limited | Porous inorganic/organic hybrid materials with ordered domains for chromatographic separations and processes for their preparation |
JP2008508516A (ja) * | 2004-07-30 | 2008-03-21 | ウオーターズ・インベストメンツ・リミテツド | クロマトグラフィー分離用の秩序領域を有する多孔質無機/有機のハイブリッド材料およびこれらの調製方法 |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2011527327A (ja) * | 2008-07-11 | 2011-10-27 | コミサリア ア レネルジー アトミック エ オ ゼネルジー アルテルナティブ | 単環式芳香族化合物およびその他の汚染物質のナノ多孔質検出器 |
JP2013544743A (ja) * | 2010-10-11 | 2013-12-19 | サントル ナスィオナル ド ラ ルシェルシュ スィアンティフィク | 泡状無機モノリシック材料を製造する方法、及び該材料の使用 |
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FR2912400B1 (fr) | 2009-04-17 |
WO2008129151A2 (fr) | 2008-10-30 |
CN101641155A (zh) | 2010-02-03 |
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WO2008129151A3 (fr) | 2009-02-19 |
US20210316288A1 (en) | 2021-10-14 |
CN101641155B (zh) | 2013-07-10 |
CA2677958A1 (fr) | 2008-10-30 |
FR2912400A1 (fr) | 2008-08-15 |
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