JP5308665B2 - 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 - Google Patents
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 Download PDFInfo
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- JP5308665B2 JP5308665B2 JP2007523612A JP2007523612A JP5308665B2 JP 5308665 B2 JP5308665 B2 JP 5308665B2 JP 2007523612 A JP2007523612 A JP 2007523612A JP 2007523612 A JP2007523612 A JP 2007523612A JP 5308665 B2 JP5308665 B2 JP 5308665B2
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- 239000000463 material Substances 0.000 title claims abstract description 183
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- 238000000034 method Methods 0.000 claims abstract description 91
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- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 27
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical group [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 24
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- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 15
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- 238000000634 powder X-ray diffraction Methods 0.000 claims description 11
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- AUHZEENZYGFFBQ-UHFFFAOYSA-N 1,3,5-trimethylbenzene Chemical compound CC1=CC(C)=CC(C)=C1 AUHZEENZYGFFBQ-UHFFFAOYSA-N 0.000 claims description 8
- VUMCUSHVMYIRMB-UHFFFAOYSA-N 1,3,5-tri(propan-2-yl)benzene Chemical compound CC(C)C1=CC(C(C)C)=CC(C(C)C)=C1 VUMCUSHVMYIRMB-UHFFFAOYSA-N 0.000 claims description 7
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 claims description 7
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- WOWHHFRSBJGXCM-UHFFFAOYSA-M cetyltrimethylammonium chloride Chemical compound [Cl-].CCCCCCCCCCCCCCCC[N+](C)(C)C WOWHHFRSBJGXCM-UHFFFAOYSA-M 0.000 claims description 7
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- DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 claims description 6
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- LZZYPRNAOMGNLH-UHFFFAOYSA-M Cetrimonium bromide Chemical compound [Br-].CCCCCCCCCCCCCCCC[N+](C)(C)C LZZYPRNAOMGNLH-UHFFFAOYSA-M 0.000 claims description 5
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- NKJOXAZJBOMXID-UHFFFAOYSA-N 1,1'-Oxybisoctane Chemical compound CCCCCCCCOCCCCCCCC NKJOXAZJBOMXID-UHFFFAOYSA-N 0.000 claims description 2
- YAYNEUUHHLGGAH-UHFFFAOYSA-N 1-chlorododecane Chemical compound CCCCCCCCCCCCCl YAYNEUUHHLGGAH-UHFFFAOYSA-N 0.000 claims description 2
- CMCBDXRRFKYBDG-UHFFFAOYSA-N 1-dodecoxydodecane Chemical compound CCCCCCCCCCCCOCCCCCCCCCCCC CMCBDXRRFKYBDG-UHFFFAOYSA-N 0.000 claims description 2
- CKQAOGOZKZJUGA-UHFFFAOYSA-N 1-nonyl-4-(4-nonylphenoxy)benzene Chemical compound C1=CC(CCCCCCCCC)=CC=C1OC1=CC=C(CCCCCCCCC)C=C1 CKQAOGOZKZJUGA-UHFFFAOYSA-N 0.000 claims description 2
- TYTUELFFKLZOTE-UHFFFAOYSA-N 2-amino-2-(hydroxymethyl)propane-1,3-diol;dodecyl hydrogen sulfate Chemical compound OCC(N)(CO)CO.CCCCCCCCCCCCOS(O)(=O)=O TYTUELFFKLZOTE-UHFFFAOYSA-N 0.000 claims description 2
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 claims description 2
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 claims description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical class OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 claims description 2
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims description 2
- BTBJBAZGXNKLQC-UHFFFAOYSA-N ammonium lauryl sulfate Chemical compound [NH4+].CCCCCCCCCCCCOS([O-])(=O)=O BTBJBAZGXNKLQC-UHFFFAOYSA-N 0.000 claims description 2
- 229940063953 ammonium lauryl sulfate Drugs 0.000 claims description 2
- 150000004649 carbonic acid derivatives Chemical class 0.000 claims description 2
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 claims description 2
- FBELJLCOAHMRJK-UHFFFAOYSA-L disodium;2,2-bis(2-ethylhexyl)-3-sulfobutanedioate Chemical group [Na+].[Na+].CCCCC(CC)CC(C([O-])=O)(C(C([O-])=O)S(O)(=O)=O)CC(CC)CCCC FBELJLCOAHMRJK-UHFFFAOYSA-L 0.000 claims description 2
- 235000019253 formic acid Nutrition 0.000 claims description 2
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 claims description 2
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- 125000001827 mesitylenyl group Chemical group [H]C1=C(C(*)=C(C([H])=C1C([H])([H])[H])C([H])([H])[H])C([H])([H])[H] 0.000 claims description 2
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- YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 claims description 2
- QNXQYOUWVYCTEL-UHFFFAOYSA-N 1-chloro-18,18-dimethylnonadecane Chemical compound CC(C)(C)CCCCCCCCCCCCCCCCCCl QNXQYOUWVYCTEL-UHFFFAOYSA-N 0.000 claims 1
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- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
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Images
Classifications
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- B01J20/28054—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof characterised by their form or physical properties characterised by their surface properties or porosity
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- B29—WORKING OF PLASTICS; WORKING OF SUBSTANCES IN A PLASTIC STATE IN GENERAL
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G83/00—Macromolecular compounds not provided for in groups C08G2/00 - C08G81/00
- C08G83/001—Macromolecular compounds containing organic and inorganic sequences, e.g. organic polymers grafted onto silica
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L83/00—Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon only; Compositions of derivatives of such polymers
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
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Description
(A)x(B)y(C)z(式I)
(式中、繰り返し単位A、B、およびCの順序は、ランダム、ブロック、またはランダムとブロックとの組み合わせであってよく;
Aは、有機結合を介して1つ以上の繰り返し単位AまたはBに共有結合している、有機繰り返し単位であり;
Bは、無機シロキサン結合を介して1つ以上の繰り返し単位BまたはCに結合しており、有機結合を介して1つ以上の繰り返し単位AまたはBにさらに結合することができる、オルガノシロキサン繰り返し単位であり;
Cは、無機結合を介して1つ以上の繰り返し単位BまたはCに結合している、無機繰り返し単位であり;
x、yは正の数であり、zは負でない数であり、z=0である場合、0.002≦x/y≦210であり、z≠0である場合、0.0003≦y/z≦500および0.002≦x/(y+z)≦210である);
(A)x(B)y(B*)y*(C)z(式II)
(式中、繰り返し単位A、B、B*、およびCの順序は、ランダム、ブロック、またはランダムとブロックとの組み合わせであってよく;
Aは、有機結合を介して1つ以上の繰り返し単位AまたはBに共有結合している、有機繰り返し単位であり;
Bは、無機シロキサン結合を介して1つ以上の繰り返し単位BまたはB*またはCに結合しており、有機結合を介して1つ以上の繰り返し単位AまたはBにさらに結合することができる、オルガノシロキサン繰り返し単位であり;
B*は、無機シロキサン結合を介して1つ以上の繰り返し単位BまたはB*またはCに結合しているオルガノシロキサン繰り返し単位であり、B*は、反応性(すなわち重合性)有機成分を有さず、重合後に脱保護可能な保護された官能基をさらに有することができる、オルガノシロキサン繰り返し単位であり;
Cは、無機結合を介して1つ以上の繰り返し単位BまたはB*またはCに結合している、無機繰り返し単位であり;
x、yは正の数であり、zは負でない数であり、z=0である場合、0.002≦x/(y+y*)≦210であり、z≠0である場合、0.0003≦(y+y*)/z≦500および0.002≦x/(y+y*+z)≦210である);または
[A]y[B]x(式III)
(式中、xおよびyは整数であり、Aは、
SiO2/(R1 pR2 qSiOt)nまたはSiO2/[R3(R1 rSiOt)m]n
であり;式中、R1およびR2は独立して、置換または非置換C1−C7アルキル基、もしくは置換または非置換アリール基であり、R3は、2つ以上のケイ素原子を架橋させる置換または非置換C1−C7アルキレン基、アルケニレン基、アルキニレン基、またはアリーレン基であり、pおよびqは0、1、または2であり、但しp+q=1または2であり、p+q=1の場合、t=1.5であり、p+q=2の場合、t=1であり;rは0または1であり、但しr=0の場合、t=1.5であり、r=1の場合、t=1であり;mは2以上の整数であり;nは0.01から100の数であり;
Bは:
SiO2/(R4 vSiOt)n
であり、式中、R4は、ヒドロキシル、フッ素、アルコキシ、アリールオキシ、置換シロキサン、タンパク質、ペプチド、炭水化物、核酸、またはこれらの組み合わせであり、R4は、R1、R2、およびR3ではなく;vは1または2であり、但し、v=1の場合、t=1.5であり、v=2の場合、t=1であり;nは0.01から100の数であり;
式IIIの材料は、内部領域および外面を有し、前記材料の前記内部領域はAで表される組成を有し;前記材料の前記外面はAおよびBで表される組成を有し、前記外部の組成は、約1から約99%の間のBの組成と、残分を構成するAとである)。
(a)孔再構成テンプレートを形成する工程と;
(b)多孔質ハイブリッド無機/有機材料の孔を、孔再構成テンプレートと接触させることで、孔を秩序領域に再構成させることによって、多孔質ハイブリッド無機/有機材料の孔を再構成させる工程と;
(c)孔再構成テンプレートを再構成された孔から除去し、これによって秩序領域を含む多孔質ハイブリッド無機/有機材料を調製する工程とを含む。
(a)孔再構成テンプレートを形成する工程と;
(b)多孔質ハイブリッド無機/有機材料の孔を、孔再構成テンプレートと接触させることで、孔を秩序領域に再構成させることによって、多孔質ハイブリッド無機/有機材料の孔を再構成させる工程と;
(c)孔再構成テンプレートを再構成された孔から除去する工程とを含む方法によって調製された材料を提供する。
本発明は、秩序領域を有する、多孔質ハイブリッド無機/有機材料を提供する。ある実施形態においては、本発明のハイブリッド材料は、クロマトグラフィー的に向上した孔形状も有する。本発明の材料は、球状粒子またはモノリスとして存在することができる。
本発明は、適切に形成されたメソポーラス材料を使用する。このような材料は、たとえば、米国特許第6,686,035号、WO03/014450、米国特許第6,528,167号、およびWO04/041398に記載されている。
(A)x(B)y(C)z(式I)
(式中、繰り返し単位A、B、およびCの順序は、ランダム、ブロック、またはランダムとブロックとの組み合わせであってよく;
Aは、有機結合を介して1つ以上の繰り返し単位AまたはBに共有結合している、有機繰り返し単位であり;
Bは、無機シロキサン結合を介して1つ以上の繰り返し単位BまたはCに結合しており、有機結合を介して1つ以上の繰り返し単位AまたはBにさらに結合することができる、オルガノシロキサン繰り返し単位であり;
Cは、無機結合を介して1つ以上の繰り返し単位BまたはCに結合している、無機繰り返し単位であり;
x、yは正の数であり、zは負でない数であり、z=0である場合、0.002≦x/y≦210であり、z≠0である場合、0.0003≦y/z≦500および0.002≦x/(y+z)≦210である);
(A)x(B)y(B*)y*(C)z(式II)
(式中、繰り返し単位A、B、B*、およびCの順序は、ランダム、ブロック、またはランダムとブロックとの組み合わせであってよく;
Aは、有機結合を介して1つ以上の繰り返し単位AまたはBに共有結合している、有機繰り返し単位であり;
Bは、無機シロキサン結合を介して1つ以上の繰り返し単位BまたはB*またはCに結合しており、有機結合を介して1つ以上の繰り返し単位AまたはBにさらに結合することができる、オルガノシロキサン繰り返し単位であり;
B*は、無機シロキサン結合を介して1つ以上の繰り返し単位BまたはB*またはCに結合しているオルガノシロキサン繰り返し単位であり、B*は、反応性(すなわち重合性)有機成分を有さず、重合後に脱保護可能な保護された官能基をさらに有することができる、オルガノシロキサン繰り返し単位であり;
Cは、無機結合を介して1つ以上の繰り返し単位BまたはB*またはCに結合している、無機繰り返し単位であり;
x、yは正の数であり、zは負でない数であり、z=0である場合、0.002≦x/(y+y*)≦210であり、z≠0である場合、0.0003≦(y+y*)/z≦500および0.002≦x/(y+y*+z)≦210である);または
[A]y[B]x(式III)
(式中、xおよびyは自然数であり、Aは、
SiO2/(R1 pR2 qSiOt)nまたはSiO2/[R3(R1 rSiOt)m]n
であり;式中、R1およびR2は独立して、置換または非置換C1−C7アルキル基、もしくは置換または非置換アリール基であり、R3は、2つ以上のケイ素原子を架橋させる置換または非置換C1−C7アルキレン基、アルケニレン基、アルキニレン基、またはアリーレン基であり、pおよびqは0、1、または2であり、但しp+q=1または2であり、p+q=1の場合、t=1.5であり、p+q=2の場合、t=1であり;rは0または1であり、但しr=0の場合、t=1.5であり、r=1の場合,t=1であり;mは2以上の整数であり;nは0.01から100の数であり;
Bは:
SiO2/(R4 vSiOt)n
であり、式中、R4は、ヒドロキシル、フッ素、アルコキシ、アリールオキシ、置換シロキサン、タンパク質、ペプチド、炭水化物、核酸、またはこれらの組み合わせであり、R4は、R1、R2、およびR3ではなく;vは1または2であり、但し、v=1の場合、t=1.5であり、v=2の場合、t=1であり;nは0.01から100の数であり;
式IIIの材料は、内部領域および外面を有し、前記材料の前記内部領域はAで表される組成を有し;この材料の前記外面はAおよびBで表される組成を有し、前記外部の組成は、約1から約99%の間のBの組成と、残分を構成するAとである)。
式中、各Rは独立して、HまたはC1−C10アルキル基であり;mは1から20の整数であり;nは0から10の整数であり;Qは、水素、N(C1‐6アルキル)3、N(C1‐6アルキル)2(C1‐6アルキレン−SO3)、またはC(C1‐6ヒドロキシアルキル)3である。ある実施形態においては、各Rは独立して、水素、メチル、エチル、またはプロピルである。
−OSi(R5)2−R6
であり、式中、R5は、C1−C6直鎖、環状、または分岐のアルキル、アリール、またはアルコキシ基、ヒドロキシル基、もしくはシロキサン基であり、R6は、C1−C36直鎖、環状、または分岐のアルキル、アリール、またはアルコキシ基であり、R6は、非置換であるか、もしくは、ハロゲン、シアノ、アミノ、ジオール、ニトロ、エーテル、カルボニル、エポキシド、スルホニル、陽イオン交換体、陰イオン交換体、カルバメート、アミド、尿素、ペプチド、タンパク質、炭水化物、核酸官能基、およびこれらの組み合わせからなる群より選択される1つ以上の部分で置換されているかである。ある実施形態においては、R6はC18基であり、別の実施形態においては、R6はシアノプロピル基である。
前述のようにして調製した多孔質無機/有機ハイブリッド材料は、秩序領域を有する材料を得るためにさらに加工される。秩序領域は、塩基触媒による変換によってこれらのメソポーラスハイブリッド材料中に形成される。この方法によると、種々の孔テンプレート分子を使用し、場合によりテンプレート膨潤分子を併用することによって、種々のメソポーラスハイブリッド材料に孔再構成テンプレートを形成することができる。本発明の方法は、多孔質無機材料(すなわちシリカゲル)の再構成に使用されているメソ孔再構成プロトコル(たとえば、孔テンプレート分子の選択、溶液組成、テンプレート膨潤分子の選択、温度、および時間)を使用する(T.マーティン(Martin)、A.ガラルノー(Galarneau)、F.ディ・レンゾ(Di Renzo)、F.ファジュラ(Fajula)、D.プリー(Plee)、Angew.Chem.Int.Ed.41(2002)2590)。
(a)孔テンプレート分子を含む孔再構成テンプレートを形成する工程と;
(b)多孔質ハイブリッド無機/有機材料の孔を、孔再構成テンプレートと接触させることで、孔を秩序領域に再構成させることによって、多孔質ハイブリッド無機/有機材料の孔を再構成させる工程と;
(c)孔再構成テンプレートを再構成された孔から除去し、これによって秩序領域を含む多孔質ハイブリッド無機/有機材料を調製する工程とによって調製される。
秩序領域を有する多孔質無機/有機ハイブリッド材料の調製、およびこれらの使用を説明する以下の非限定的実施例によって、本発明をさらに説明することができる。
特に明記しない限り、すべての試薬は入手したままの状態で使用した。当業者であれば、存在する以下の供給品および供給元と同等のものを理解できるであろうし、したがって以下に示す供給元は限定のために構成されたものではない。
当業者であれば、存在する以下の機器および供給元と同等のものを理解できるであろうし、したがって以下に示す供給元は限定のために構成されたものではない。
本明細書に記載されるすべての特許、公開特許出願、および他の参考文献のすべての内容は、これらの内容全体が参照により明示的に本明細書に組み込まれる。
(同等物)
当業者であれば、単に日常的な実験によって、本明細書に記載される具体的な手順の多数の同等物を認識し、確認することができる。このような同等物は、本発明の範囲内にあると見なされ、特許請求の範囲に含まれている。本出願全体に記載されるすべての参考文献、交付済み特許、および公開特許出願は、参照により本明細書に組み込まれる。
Claims (36)
- 秩序領域を含み、クロマトグラフィー的に向上した孔形状を有する多孔質ハイブリッド無機/有機材料を調製する方法であって、該多孔質ハイブリッド無機/有機材料は、有機官能性が内部構造または骨格無機構造と、ハイブリッド材料表面との両方と一体となっている無機系構造を含み、該秩序領域は、X線粉末回折(XRPD)で測定して0.8から20°スキャン範囲(x軸、2θ単位)に回折ピークを示し、多孔質無機/有機ハイブリッド材料中に見られる領域であり、
34Å未満の直径の孔が、材料の比表面積の110m 2 /g未満に寄与し、材料について観察される最大回折ピークが、非晶質材料による原子範囲秩序によって得られる回折ピークを排除した2θ位置を示す、
材料であり、
(a)孔再構成テンプレートを準備する工程と、ここで、該孔再構成テンプレートが1種類以上の孔テンプレート分子を含み、該孔テンプレート分子が、ビス(2−エチルヘキシル)スルホコハク酸ナトリウム、グリコール酸エトキシレート4−tert−ブチルフェニルエーテル、グリコール酸エトキシレートラウリルエーテル、グリコール酸エトキシレート4−ノニルフェニルエーテル、グリコール酸エトキシレートオクチルエーテル、グリコール酸エトキシレートオレイルエーテル、ドデシル硫酸ナトリウム(SDS)、またはトリス(ヒドロキシメチル)アミノメタンラウリルサルフェート(TDS)、ラウリル硫酸アンモニウム、塩化セチルトリメチルアンモニウム、臭化セチルトリメチルアンモニウム、塩化トリメチルステアリルアンモニウム、ポリ(エチレンオキシド)−ポリ(プロピレンオキシド)−ポリ(エチレンオキシド)、プルロニック(Pluronic)(登録商標)P123、プルロニック(登録商標)P64、プルロニックP105、ブリジ(Brij)(登録商標)76、及びブリジ(登録商標)30からなる群から選択され;
(b)多孔質ハイブリッド無機/有機材料の孔を、前記孔再構成テンプレートと接触させることで、前記孔を秩序領域に再構成させることによって、前記多孔質ハイブリッド無機/有機材料の前記孔を再構成させる工程と;および
(c)前記孔再構成テンプレートを再構成された前記孔から除去し、これによって秩序領域を含む多孔質ハイブリッド無機/有機材料を調製する工程と
を含む、前記方法。 - 工程(b)の再構成が、多孔質ハイブリッド無機/有機材料を、塩基と孔再構成テンプレートとを含有する水溶液と混合する工程と、および秩序領域を形成するのに十分な温度および時間、前記混合物を加熱する工程とを含む、請求項1に記載の方法。
- 混合物が、25から200℃の範囲の温度に1から120時間の範囲の時間加熱される、請求項2に記載の方法。
- 混合物が、80から150℃の範囲の温度に7から120時間の範囲の時間加熱される、請求項3に記載の方法。
- 混合物が、100から130℃の範囲の温度に20から48時間の範囲の時間加熱される、請求項3に記載の方法。
- 工程(b)の接触が、多孔質ハイブリッド無機/有機材料の孔に、孔再構成テンプレートを充填する工程を含む、請求項1に記載の方法。
- 孔再構成テンプレートがテンプレート膨潤分子をさらに含む、請求項1に記載の方法。
- 多孔質ハイブリッド無機/有機材料を得る工程をさらに含む、請求項1に記載の方法。
- 多孔質ハイブリッド無機/有機材料を調製する工程をさらに含む、請求項1に記載の方法。
- 工程(c)の除去が、工程(b)の生成物を酸洗浄することによって孔再構成テンプレートを抽出することで、孔再構成テンプレートを除去する工程を含む、請求項1に記載の方法。
- 酸洗浄液が、水溶性溶媒と酸との混合物を含む、請求項10に記載の方法。
- 水溶性溶媒が、アセトニトリル、テトラヒドロフラン、ジメチルスルホキシド、ジメチルホルムアミド、メタノール、エタノール、およびイソプロパノールからなる群より選択される、請求項11に記載の方法。
- 酸が、塩酸、臭化水素酸、フッ化水素酸、ヨウ化水素酸、硫酸、ギ酸、酢酸、トリクロロ酢酸、トリフルオロ酢酸、およびリン酸からなる群より選択される、請求項11に記載の方法。
- 酸洗浄液が、エタノールと濃塩酸との混合物を含む、請求項11に記載の方法。
- 工程(b)の生成物が、25から100℃の範囲の温度で、1から30時間の範囲の時間、酸洗浄される、請求項10に記載の方法。
- 工程(b)の生成物が、40から60℃の範囲の温度で、4から25時間の範囲の時間、酸洗浄される、請求項10に記載の方法。
- 工程(b)の生成物が、50℃の温度で、20時間、酸洗浄される、請求項10に記載の方法。
- 工程(c)の除去が、工程(b)の生成物の熱処理によって孔再構成テンプレートを除去することを含む、請求項1に記載の方法。
- 工程(b)の生成物が、250から600℃の範囲の温度に、1から30時間の範囲の時間加熱される、請求項18に記載の方法。
- 工程(b)の生成物が、275から350℃の範囲の温度に、4から25時間の範囲の時間加熱される、請求項18に記載の方法。
- 工程(b)の生成物が、300℃の温度に、16時間加熱される、請求項18に記載の方法。
- 工程(b)の生成物が、空気、窒素、およびアルゴンからなる群より選択されるガスの動的パージ下で、100℃で40分間加熱され、続いて、250から550℃で16時間加熱される、請求項18に記載の方法。
- 工程(c)の除去が、工程(b)の生成物をオゾンで処理することによって孔再構成テンプレートを除去する工程を含む、請求項1に記載の方法。
- 多孔質ハイブリッド無機/有機材料の孔構造を改質することによって、クロマトグラフィー的に向上した孔形状を形成し、これによって、秩序領域を含み、クロマトグラフィー的に向上した孔形状を有する多孔質ハイブリッド無機/有機材料を調製する工程をさらに含む、請求項1に記載の方法。
- 多孔質ハイブリッド無機/有機材料の孔構造が、工程(b)の前に改質される、請求項24に記載の方法。
- 多孔質ハイブリッド無機/有機材料の孔構造が、工程(c)の後で改質される、請求項24に記載の方法。
- 多孔質ハイブリッド無機/有機材料の表面改質を行う工程をさらに含む、請求項25に記載の方法。
- 前記表面改質が、工程(b)の前に行われる、請求項27に記載の方法。
- 多孔質ハイブリッド無機/有機材料の孔構造が、熱水処理によって改質される、請求項24に記載の方法。
- テンプレート膨潤分子が、ベンゼン、トルエン、シクロヘキサン、シクロヘキサノール、ドデカノール、クロロドデカン、1,3,5−トリメチルベンゼン、および1,3,5−トリイソプロピルベンゼンからなる群より選択される、請求項3に記載の方法。
- テンプレート膨潤分子が1,3,5−トリメチルベンゼンまたは1,3,5−トリイソプロピルベンゼンである、請求項30に記載の方法。
- 多孔質ハイブリッド無機/有機材料が多孔質ハイブリッド無機/有機粒子を含む、請求項1に記載の方法。
- 多孔質ハイブリッド無機/有機材料がモノリスを含む、請求項1に記載の方法。
- モノリスが、合体した多孔質ハイブリッド無機/有機粒子を含む、請求項33に記載の方法。
- 塩基が、水酸化アンモニウム、I族およびII族金属の水酸化物塩、I族金属の炭酸塩および炭酸水素塩、もしくはI族およびII族金属のアルコキシド塩、ならびにアルキルアミンからなる群より選択される、請求項2に記載の方法。
- 塩基が水酸化ナトリウムである、請求項35に記載の方法。
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WO2006019988A1 (en) | 2006-02-23 |
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US9145481B2 (en) | 2015-09-29 |
GB0703767D0 (en) | 2007-04-04 |
GB2433937A (en) | 2007-07-11 |
JP6225099B2 (ja) | 2017-11-01 |
JP2008508516A (ja) | 2008-03-21 |
JP2015111120A (ja) | 2015-06-18 |
JP2013210382A (ja) | 2013-10-10 |
GB2433937B (en) | 2009-09-02 |
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