CA2544636A1 - Polar silanes for binding to substrates and use of the bound substrates in chromatography - Google Patents
Polar silanes for binding to substrates and use of the bound substrates in chromatography Download PDFInfo
- Publication number
- CA2544636A1 CA2544636A1 CA 2544636 CA2544636A CA2544636A1 CA 2544636 A1 CA2544636 A1 CA 2544636A1 CA 2544636 CA2544636 CA 2544636 CA 2544636 A CA2544636 A CA 2544636A CA 2544636 A1 CA2544636 A1 CA 2544636A1
- Authority
- CA
- Canada
- Prior art keywords
- silicon compound
- composition
- group
- substrate
- alkyl
- 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.)
- Abandoned
Links
- 239000000758 substrate Substances 0.000 title claims abstract 15
- 238000004587 chromatography analysis Methods 0.000 title claims abstract 3
- 150000004756 silanes Chemical class 0.000 title 1
- 150000003377 silicon compounds Chemical class 0.000 claims abstract 16
- 125000000217 alkyl group Chemical group 0.000 claims abstract 8
- 125000000547 substituted alkyl group Chemical group 0.000 claims abstract 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract 4
- 229910002808 Si–O–Si Inorganic materials 0.000 claims abstract 3
- -1 amino, thio Chemical group 0.000 claims abstract 3
- 125000003118 aryl group Chemical group 0.000 claims abstract 3
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract 3
- 125000000524 functional group Chemical group 0.000 claims abstract 3
- 125000001475 halogen functional group Chemical group 0.000 claims abstract 3
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims abstract 3
- 125000003107 substituted aryl group Chemical group 0.000 claims abstract 3
- 125000001273 sulfonato group Chemical group [O-]S(*)(=O)=O 0.000 claims abstract 3
- 239000000203 mixture Substances 0.000 claims 9
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims 6
- 239000000499 gel Substances 0.000 claims 4
- 239000007788 liquid Substances 0.000 claims 3
- 239000002609 medium Substances 0.000 claims 3
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 claims 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims 2
- 150000001408 amides Chemical class 0.000 claims 2
- 239000004202 carbamide Substances 0.000 claims 2
- 229920000642 polymer Polymers 0.000 claims 2
- 238000004366 reverse phase liquid chromatography Methods 0.000 claims 2
- 238000000926 separation method Methods 0.000 claims 2
- 239000000741 silica gel Substances 0.000 claims 2
- 229910002027 silica gel Inorganic materials 0.000 claims 2
- 239000000377 silicon dioxide Substances 0.000 claims 2
- 229940124530 sulfonamide Drugs 0.000 claims 2
- 150000003456 sulfonamides Chemical class 0.000 claims 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
- 125000003545 alkoxy group Chemical group 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
- 238000013375 chromatographic separation Methods 0.000 claims 1
- 239000012501 chromatography medium Substances 0.000 claims 1
- 125000004093 cyano group Chemical group *C#N 0.000 claims 1
- 239000011521 glass Substances 0.000 claims 1
- 150000004820 halides Chemical group 0.000 claims 1
- 238000000034 method Methods 0.000 claims 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 1
- FZHAPNGMFPVSLP-UHFFFAOYSA-N silanamine Chemical group [SiH3]N FZHAPNGMFPVSLP-UHFFFAOYSA-N 0.000 claims 1
- SCPYDCQAZCOKTP-UHFFFAOYSA-N silanol Chemical compound [SiH3]O SCPYDCQAZCOKTP-UHFFFAOYSA-N 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 238000012856 packing Methods 0.000 abstract 1
- 0 CN(CCI(C)[Si]I)** Chemical compound CN(CCI(C)[Si]I)** 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
-
- 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
- B01J20/00—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof
- B01J20/30—Processes for preparing, regenerating, or reactivating
- B01J20/32—Impregnating or coating ; Solid sorbent compositions obtained from processes involving impregnating or coating
- B01J20/3231—Impregnating or coating ; Solid sorbent compositions obtained from processes involving impregnating or coating characterised by the coating or impregnating layer
- B01J20/3242—Layers with a functional group, e.g. an affinity material, a ligand, a reactant or a complexing group
-
- 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
- B01J20/00—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof
- B01J20/281—Sorbents specially adapted for preparative, analytical or investigative chromatography
- B01J20/286—Phases chemically bonded to a substrate, e.g. to silica or to polymers
-
- 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
- B01J20/00—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof
- B01J20/281—Sorbents specially adapted for preparative, analytical or investigative chromatography
- B01J20/286—Phases chemically bonded to a substrate, e.g. to silica or to polymers
- B01J20/287—Non-polar phases; Reversed phases
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
- C07F7/1804—Compounds having Si-O-C linkages
-
- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N30/00—Investigating or analysing materials by separation into components using adsorption, absorption or similar phenomena or using ion-exchange, e.g. chromatography or field flow fractionation
-
- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N30/00—Investigating or analysing materials by separation into components using adsorption, absorption or similar phenomena or using ion-exchange, e.g. chromatography or field flow fractionation
- G01N30/02—Column chromatography
-
- 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
- B01J2220/00—Aspects relating to sorbent materials
- B01J2220/50—Aspects relating to the use of sorbent or filter aid materials
- B01J2220/54—Sorbents specially adapted for analytical or investigative chromatography
-
- 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
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/31504—Composite [nonstructural laminate]
- Y10T428/31652—Of asbestos
- Y10T428/31663—As siloxane, silicone or silane
Landscapes
- Chemical & Material Sciences (AREA)
- Analytical Chemistry (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Physics & Mathematics (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- General Physics & Mathematics (AREA)
- Immunology (AREA)
- Pathology (AREA)
- Solid-Sorbent Or Filter-Aiding Compositions (AREA)
- Treatment Of Liquids With Adsorbents In General (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US10/702,109 | 2003-11-04 | ||
| US10/702,109 US7074491B2 (en) | 2003-11-04 | 2003-11-04 | Polar silanes for binding to substrates and use of the bound substrates |
| PCT/US2004/032655 WO2005047886A1 (en) | 2003-11-04 | 2004-10-04 | Polar silanes for binding to substrates and use of the bound substrates in chromatography |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2544636A1 true CA2544636A1 (en) | 2005-05-26 |
Family
ID=34551590
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA 2544636 Abandoned CA2544636A1 (en) | 2003-11-04 | 2004-10-04 | Polar silanes for binding to substrates and use of the bound substrates in chromatography |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US7074491B2 (enExample) |
| EP (1) | EP1680432B1 (enExample) |
| JP (1) | JP4904161B2 (enExample) |
| KR (1) | KR20060125788A (enExample) |
| CN (1) | CN1901990B (enExample) |
| AU (1) | AU2004288994B2 (enExample) |
| CA (1) | CA2544636A1 (enExample) |
| WO (1) | WO2005047886A1 (enExample) |
Families Citing this family (22)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7402243B2 (en) | 2004-09-10 | 2008-07-22 | Dionex Corporation | Organosilanes and substrate bonded with same |
| US7468130B2 (en) * | 2005-02-15 | 2008-12-23 | Dionex Corporation | Organosilanes and substrates covalently bonded with same and methods for synthesis and use same |
| US7557232B2 (en) * | 2007-05-25 | 2009-07-07 | Dionex Corporation | Compositions useful as chromatography stationary phases |
| US9314712B2 (en) | 2008-05-09 | 2016-04-19 | Dionex Corporation | Functionalized substrates with ion-exchange properties |
| CN102939140B (zh) | 2010-05-19 | 2015-05-20 | 迪奥内克斯公司 | 具有芳香族堆积特性的官能化的基质 |
| EP2675560B1 (en) | 2011-02-14 | 2019-08-28 | Dionex Corporation | Liquid chromatographic column including a ligand comprising a polyhedral oligomeric silsequioxane moiety, and liquid chromatografic method using the column |
| CN104428045B (zh) | 2012-05-15 | 2017-12-01 | 沃特世科技公司 | 色谱材料 |
| CN111644164B (zh) * | 2012-05-15 | 2024-03-08 | 沃特世科技公司 | 用于分离不饱和分子的色谱材料 |
| SG11201404681VA (en) | 2012-09-17 | 2014-09-26 | Grace W R & Co | Chromatography media and devices |
| US9610576B2 (en) | 2012-09-27 | 2017-04-04 | Agilent Technologies, Inc. | Hydrolytically stable ion-exchange stationary phases and uses thereof |
| CN103357390A (zh) * | 2012-11-12 | 2013-10-23 | 北京迪马欧泰科技发展中心 | 多层结构键合硅胶液相色谱填料及其合成方法 |
| US9169331B2 (en) | 2012-12-21 | 2015-10-27 | Dionex Corporation | Separation of glycans by mixed-mode liquid chromatography |
| EP2745904B1 (en) | 2012-12-21 | 2015-12-16 | Dionex Corporation | HILIC/Anion-Exchange/Cation-Exchange Multimodal Media |
| US9310344B2 (en) | 2013-06-14 | 2016-04-12 | Dionex Corporation | HILIC/anion-exchange/cation-exchange multimodal media |
| CN103170311A (zh) * | 2013-03-20 | 2013-06-26 | 华东理工大学 | 新型氨基系列色谱固定相及制备方法 |
| EP3936226A3 (en) | 2013-06-11 | 2022-03-16 | Waters Technologies Corporation | Chromatographic columns and separation devices comprising a superficially porous material; and use thereof for supercritical fluid chromatography and other chromatography |
| CN107847907A (zh) | 2014-05-02 | 2018-03-27 | 格雷斯公司 | 官能化载体材料以及制备和使用官能化载体材料的方法 |
| WO2016115101A1 (en) | 2015-01-15 | 2016-07-21 | Dionex Corporation | Chromatographic material having improved ph stability, method for preparation thereof and uses thereof |
| US10695744B2 (en) | 2015-06-05 | 2020-06-30 | W. R. Grace & Co.-Conn. | Adsorbent biprocessing clarification agents and methods of making and using the same |
| US10618920B2 (en) | 2016-06-03 | 2020-04-14 | Agilent Technologies, Inc. | Functionalized particles having modified phases |
| US20190126167A1 (en) | 2017-11-01 | 2019-05-02 | Dionex Corporation | Sulfonamide based anion exchange resins |
| CN111135808B (zh) * | 2019-12-30 | 2023-03-31 | 纳谱分析技术（苏州）有限公司 | 硅化合物、固定相及其应用 |
Family Cites Families (28)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE623601A (enExample) * | 1961-10-16 | 1900-01-01 | ||
| DE2250921A1 (de) | 1972-10-18 | 1974-04-25 | Dynamit Nobel Ag | Neue silane von sulfon- und phosphorsaeureamiden |
| DE2357184A1 (de) * | 1973-11-16 | 1975-05-22 | Merck Patent Gmbh | Verfahren zur herstellung von organisch modifizierten siliciumdioxiden |
| DE2641201A1 (de) * | 1976-09-14 | 1978-03-16 | Consortium Elektrochem Ind | Diorganopolysiloxane enthaltende gemische und verfahren zu ihrer herstellung |
| US4584138A (en) * | 1983-09-30 | 1986-04-22 | Union Carbide Corporation | Novel fatty ethenoid acylaminoorganosilicon compounds and their use as a coupling agent |
| DE3424534A1 (de) * | 1984-07-04 | 1986-01-09 | Degussa Ag, 6000 Frankfurt | N,n'- und n,n',n'-substituierte silylharnstoffe und verfahren zu deren herstellung |
| US4705725A (en) * | 1986-11-28 | 1987-11-10 | E. I. Du Pont De Nemours And Company | Substrates with sterically-protected, stable, covalently-bonded organo-silane films |
| DE3706521A1 (de) * | 1987-02-28 | 1988-09-08 | Degussa | Benzoylthioharnstoffgruppen-haltige organosilane, verfahren zu ihrer herstellung |
| DE3821465A1 (de) * | 1988-06-25 | 1989-12-28 | Degussa | Verfahren zur herstellung ein- oder mehrfach substituierter organyloxysilylfunktioneller thioharnstoffe und diese verbindungen |
| JPH0219387A (ja) * | 1988-07-08 | 1990-01-23 | Toshiba Silicone Co Ltd | 有機ケイ素化合物およびその製造方法 |
| US4990641A (en) * | 1988-07-08 | 1991-02-05 | Toshiba Silicone Co., Ltd. | Organosilicon compound and its preparing method |
| JPH02107650A (ja) * | 1988-10-17 | 1990-04-19 | Toshiba Silicone Co Ltd | 無機ケイ素質充填剤用処理剤 |
| DE3837415A1 (de) * | 1988-11-04 | 1990-05-10 | Degussa | Organopolysiloxan-harnstoff- und organopolysiloxan-thioharnstoff-derivate, verfahren zu ihrer herstellung und verwendung |
| US5290440A (en) | 1992-06-23 | 1994-03-01 | Research Corporation Technologies, Inc. | High performance chiral selector |
| US5374755A (en) * | 1992-07-17 | 1994-12-20 | Millipore Corporation | Liquid chromatography stationary phases with reduced silanol interactions |
| US5523443A (en) | 1992-10-13 | 1996-06-04 | Caschem, Inc. | Dual curing conformal coatings |
| US5888491A (en) | 1993-12-06 | 1999-03-30 | Minnesota Mining And Manufacturing Company | Optionally crosslinkable coatings, compositions and methods of use |
| CA2222137A1 (en) * | 1995-06-05 | 1996-12-12 | Basil V. Gregorovich | Coating composition containing silane functionality |
| DE69721748T2 (de) * | 1996-12-30 | 2004-03-11 | Hydro-Québec, Montréal | Oberflächenmodifizierte kohlenstoffmaterialien |
| DE19756831A1 (de) * | 1997-12-19 | 1999-07-01 | Wacker Chemie Gmbh | Siliciumdioxid, das an seiner Oberfläche teil- oder vollständig silylierte Polykieselsäureketten trägt |
| JPH11335380A (ja) | 1998-05-22 | 1999-12-07 | Nitto Boseki Co Ltd | 耐水性向上シランカップリング剤 |
| US6262216B1 (en) * | 1998-10-13 | 2001-07-17 | Affymetrix, Inc. | Functionalized silicon compounds and methods for their synthesis and use |
| EP1163050B1 (en) | 1999-02-05 | 2007-01-03 | Waters Investments Limited | Preparation of porous inorganic/organic hybrid particles for chromatographic separations |
| JP4387518B2 (ja) | 1999-10-18 | 2009-12-16 | 日東電工株式会社 | 接着剤組成物 |
| US6528167B2 (en) * | 2001-01-31 | 2003-03-04 | Waters Investments Limited | Porous hybrid particles with organic groups removed from the surface |
| US6800777B2 (en) * | 2001-05-03 | 2004-10-05 | Gelest, Inc. | Trialkylsilanes for use in chromatographic applications, substrates including such compounds and methods of producing the same |
| US6645378B1 (en) * | 2002-03-05 | 2003-11-11 | Dionex Corporation | Polar silanes and their use on silica supports |
| DE10393599T5 (de) * | 2002-10-30 | 2005-10-27 | Waters Investments Ltd., New Castle | Poröse anorganische/organische Homogene copolymerische Hybridmaterialien für chromatographische Auftrennungen und Verfahren für deren Herstellung |
-
2003
- 2003-11-04 US US10/702,109 patent/US7074491B2/en not_active Expired - Lifetime
-
2004
- 2004-10-04 CN CN2004800398117A patent/CN1901990B/zh not_active Expired - Lifetime
- 2004-10-04 JP JP2006538010A patent/JP4904161B2/ja not_active Expired - Lifetime
- 2004-10-04 KR KR1020067011025A patent/KR20060125788A/ko not_active Ceased
- 2004-10-04 WO PCT/US2004/032655 patent/WO2005047886A1/en not_active Ceased
- 2004-10-04 CA CA 2544636 patent/CA2544636A1/en not_active Abandoned
- 2004-10-04 AU AU2004288994A patent/AU2004288994B2/en not_active Ceased
- 2004-10-04 EP EP20040794125 patent/EP1680432B1/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| WO2005047886A1 (en) | 2005-05-26 |
| KR20060125788A (ko) | 2006-12-06 |
| JP2007510644A (ja) | 2007-04-26 |
| EP1680432B1 (en) | 2014-08-20 |
| EP1680432A1 (en) | 2006-07-19 |
| AU2004288994A1 (en) | 2005-05-26 |
| CN1901990B (zh) | 2013-04-03 |
| JP4904161B2 (ja) | 2012-03-28 |
| US7074491B2 (en) | 2006-07-11 |
| US20050095440A1 (en) | 2005-05-05 |
| CN1901990A (zh) | 2007-01-24 |
| AU2004288994B2 (en) | 2011-07-14 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| FZDE | Discontinued |
Effective date: 20131004 |