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WO2011012019A1 - Matière de séparation basée sur du gel de silice ayant une réaction de copolymérisation en surface et son procédé de préparation - Google Patents

Matière de séparation basée sur du gel de silice ayant une réaction de copolymérisation en surface et son procédé de préparation Download PDF

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WO2011012019A1
WO2011012019A1 PCT/CN2010/073468 CN2010073468W WO2011012019A1 WO 2011012019 A1 WO2011012019 A1 WO 2011012019A1 CN 2010073468 W CN2010073468 W CN 2010073468W WO 2011012019 A1 WO2011012019 A1 WO 2011012019A1
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polar
silica gel
preparation
separation material
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郭志谋
梁图
金高娃
梁鑫淼
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Dalian Institute of Chemical Physics of CAS
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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
    • 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
    • B01J20/30—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
    • B01J20/3244—Non-macromolecular compounds
    • 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
    • B01J20/3244—Non-macromolecular compounds
    • B01J20/3246—Non-macromolecular compounds having a well defined chemical structure
    • 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
    • B01J20/3244—Non-macromolecular compounds
    • B01J20/3246—Non-macromolecular compounds having a well defined chemical structure
    • B01J20/3257—Non-macromolecular compounds having a well defined chemical structure the functional group or the linking, spacer or anchoring group as a whole comprising at least one of the heteroatoms nitrogen, oxygen or sulfur together with at least one silicon atom, these atoms not being part of the carrier as such
    • 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
    • B01J20/3268—Macromolecular compounds
    • B01J20/3272—Polymers obtained by reactions otherwise than involving only carbon to carbon unsaturated bonds
    • 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
    • B01J20/3268—Macromolecular compounds
    • B01J20/328—Polymers on the carrier being further modified
    • 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
    • B01J20/3285—Coating or impregnation layers comprising different type of functional groups or interactions, e.g. different ligands in various parts of the sorbent, mixed mode, dual zone, bimodal, multimodal, ionic or hydrophobic, cationic or anionic, hydrophilic or hydrophobic
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01D—SEPARATION
    • B01D15/00—Separating processes involving the treatment of liquids with solid sorbents; Apparatus therefor
    • B01D15/08—Selective adsorption, e.g. chromatography
    • B01D15/26—Selective adsorption, e.g. chromatography characterised by the separation mechanism
    • B01D15/32—Bonded phase chromatography

Definitions

  • the invention relates to a separating material, in particular to a silica gel matrix bonding "non-polar/polar copolymerized stationary phase" based on copolymerization of silica gel surface and a preparation method thereof.
  • Reversed-phase high performance liquid chromatography is currently the most widely used separation analysis and purification separation technology.
  • Solid phase extraction based on reverse phase mode is also a common sample preparation and enrichment technique.
  • Silica-based alkyl groups e.g., octadecyl C18, octane C8, etc.
  • bonded stationary phases are the most commonly used separation materials for reversed phase chromatography and solid phase extraction.
  • the alkyl stationary phase provides only a single hydrophobic interaction, insufficient polar interaction, and poor selectivity for retention and separation of polar compounds.
  • the alkyl stationary phase is too hydrophobic and lacks a hydrophilic group.
  • the method of polar embedding is to insert a polar group between each non-polar ligand and silica gel, that is, the ratio between the polar group and the non-polar ligand is substantially 1:1.
  • the ratio between the polar group and the non-polar ligand is regulated.
  • the spatial positions of polar groups and non-polar ligands are relatively fixed and difficult to control.
  • Some polar embedding stationary phases also present a problem of lower stability.
  • the polar tailing method is to introduce a polar group by reacting residual silanol groups on the surface of the silica gel with a polar silane reagent after bonding the nonpolar ligand, and the number and position distribution of the polar groups are more uncertain.
  • the polar capping phase has a problem in shielding the silanol group activity and does not significantly reduce the silanol group activity on the silica surface.
  • Wirth et al. developed a method for preparing a chromatographic stationary phase by horizontal polymerization of a silane reagent using silane reagent [Peter Fairbank, R. W. et al, Anal. Chem. 1995, 67, 3879-3885]. This method was used to prepare a propyl/octadecyl mixed reverse phase stationary phase and a methyl/octadecyl mixed stationary phase [Peter Fairbank, RW et al, J. Chromatogr. A, 1999, 830, 285-291 ]. In addition, the method is also used to prepare 3-chloropropyl silica gel [Hughes, MA et al, Ind. Eng. Chem. Res.
  • the structural formula of the separation material of the present invention is as follows:
  • Silica Gel is a silica gel
  • NP is a non-polar group, and includes a normal alkyl group having 1 to 30 carbon atoms, a phenyl group and the like.
  • P is a polar group, and includes a chlorine atom, a bromine atom, a cyano group, an amine group, a benzenesulfonate group, a sulfonic acid group, a carboxyl group, a quaternary ammonium group, an alcohol bonded to a normal-chain alkyl group having 1 to 12 carbon atoms.
  • Base is a polar group, and includes a chlorine atom, a bromine atom, a cyano group, an amine group, a benzenesulfonate group, a sulfonic acid group, a carboxyl group, a quaternary ammonium group, an alcohol bonded to a normal-chain alkyl group having 1 to 12 carbon atoms.
  • the preparation method of the separation material of the present invention comprises the following steps:
  • silica gel added to a hydrochloric acid or nitric acid solution having a volume concentration of 1% to 38%, heating and refluxing for 1 to 48 hours, filtering, washing to neutrality, and drying to constant weight at 100 to 160 ° C;
  • the dried silica gel obtained in the step (1) is placed in an atmosphere having a relative humidity of 20% to 80% for 24 to 72 hours, so that the silica gel absorbs water by weight by 0.5% to 10%;
  • the organic solvent used is an organic solvent which is immiscible with water, and includes benzenes and alkanes such as toluene, ethylbenzene, xylene, n-hexane, n-heptane, n-pentane, n-octane, cyclohexane.
  • the structural formula of the non-polar silane reagent is:
  • X is a chlorine atom, a methoxy group or an ethoxy group; n is 0 to 29, and A is a phenyl group or a methyl group.
  • the structural formula of the polar silane reagent is:
  • X is a chlorine atom, a methoxy group or an ethoxy group; n is 1 to 12, and B is a chlorine atom, a bromine atom, a cyano group, an amine group, a benzenesulfonic acid group, a sulfonic acid group, a carboxyl group, a quaternary ammonium group, or a diol group.
  • the molar ratio of the non-polar silane reagent to the polar silane reagent is from 1/100 to 100/1.
  • the polar silane reagent and the non-polar silane reagent are generally used in an amount of 0.5 mmol to 5 mmol of silane reagent per gram of hydrated silica gel;
  • the separation material prepared by the invention has both a non-polar group and a polar group, and can simultaneously provide hydrophobic force and various forms of polar forces, such as hydrogen bonding, dipole- Dipole action, electrostatic attraction or repulsion can greatly improve separation selectivity. Due to the introduction of polar groups, the separation material prepared by the present invention will have improved wettability under the condition that the mobile phase contains a high content of aqueous solution, and effectively avoids the problem of loss of infiltration of the conventional reverse phase separation material. In addition, the polar group can also shield the activity of silanol groups very well. Peak shape and separation efficiency of good basic compounds.
  • the types and ratios of non-polar groups and polar groups in the stationary phase structure can be freely regulated compared to existing polar reverse phase stationary phases.
  • the preparation method provided by the present invention can prepare various types of stationary phases by combining different kinds of non-polar groups and polar groups or adjusting the ratio of polar groups and non-polar groups, as needed. Meet the separation needs of different samples.
  • the stationary phase obtained by the preparation method provided by the invention has the advantages of uniform and stable surface bonding groups, large bonding amount, and the like, and has wide application range of technology.
  • Figure 1 is a chromatogram of the infiltration property of the separation material C18HCE obtained in Example 17;
  • Figure 2 is a differential chromatogram of the separation material C18HCE obtained in Example 17 and a commercial C18 column in the separation of alkaloids;
  • Fig. 3 is a solid phase extraction chromatogram using the separation material C18/SCX-10S obtained in Example 13 for melamine. detailed description
  • spherical silica gel (particle size 5 ⁇ , pore size 10 nm, specific surface area 305 m2 / g), placed in a 250 mL glass flask, add 150 mL of a 10% hydrochloric acid solution, and heat to reflux for 12 hours. Cool to room temperature, filter, wash to neutral, and dry at 150 ° C for 24 hours. The dried silica gel was placed in a 150 mL three-neck glass bottle, and nitrogen gas with a relative humidity of 50% was continuously supplied for 48 hours to obtain a hydrated silica gel. 10.5 go. Under the condition of passing dry nitrogen, 80 mL of the hydrated silica gel was added to dry.
  • the preparation method is as follows: Weigh 10 g spherical silica gel (particle size 3 ⁇ , pore diameter 12 nm, specific surface area 290 m 2 /g), place it in a 250 mL glass flask, and add 100 mL of a 38% hydrochloric acid solution. Heat under reflux for 2 hours, cool to room temperature, filter, wash with water until neutral, and dry at 120 ° C for 24 hours. The dried silica gel was placed in a 150 mL three-neck glass bottle, and nitrogen gas having a relative humidity of 60% was continuously supplied for 24 hours to obtain 10.3 g of hydrated silica gel.
  • spherical silica gel (particle size 5 ⁇ , pore size 10 nm, specific surface area 305 m2 / g), placed in a 250 mL glass flask, add 150 mL of a 10% hydrochloric acid solution, and heat to reflux for 12 hours. Cool to room temperature, filter, wash to neutral, dry at 120 ° C for 24 hours. The dried silica gel was placed in a 150 mL three-necked glass bottle, and nitrogen gas having a relative humidity of 30% was continuously introduced for 72 hours to obtain hydrated silica gel 10.6 go. Under the condition of passing dry nitrogen, 100 mL of dry gel was added to the hydrated silica gel.
  • spherical silica gel (particle size 5 ⁇ , pore size 10 nm, specific surface area 305 m2 / g), placed in a 250 mL glass flask, add 150 mL of a 10% hydrochloric acid solution, and heat to reflux for 24 hours. Cool to room temperature, filter, wash to neutral, and dry at 150 ° C for 12 hours. The dried silica gel was placed in a 150 mL three-neck glass bottle, and nitrogen gas having a relative humidity of 50% was continuously supplied for 48 hours to obtain hydrated silica gel 10.5 go. Under the condition of passing dry nitrogen, 100 mL of dry water was added to the hydrated silica gel.
  • spherical silica gel (particle size 5 ⁇ , pore size 10 nm, specific surface area 305 m2 / g), placed in a 250 mL glass flask, add 120 mL of a 5% hydrochloric acid solution, and heat to reflux for 24 hours. Cool to room temperature, filter, wash to neutral, and dry at 150 ° C for 1 hour. The dried silica gel was placed in a 150 mL three-necked glass bottle, and nitrogen gas having a relative humidity of 30% was continuously introduced for 72 hours to obtain a hydrated silica gel 10.6 go. Under the condition of passing dry nitrogen, 100 mL of dry water was added to the hydrated silica gel.
  • Example 2 The remainder of the preparation process was the same as in Example 1 except that the silane reagent added was 18 mmol (4.2 mL) of octyltrichlorosilane and 6 mmol (0.9 mL) of 3-propyltrichlorosilane. Elemental analysis results: C 12.35%, H 2.78%; Infrared spectrum: Characteristic absorption peak at 2900-2800 cm-1. Elemental analysis and infrared spectroscopy results confirmed that the non-polar/polar copolymerized stationary phase C8/HC-3 structural formula of this example was:
  • Example 2 The remainder of the preparation was the same as in Example 1 except that the silane reagent added was 18 mmol (3.0 mL) of butyltrichlorosilane and 6 mmol (0.9 mL) of 3-chloropropyltrichlorosilane. Elemental analysis results: C 7.25%, H 1.77%; Infrared spectrum: Characteristic absorption peak at 2900-2800 cm-1. Elemental analysis and infrared spectroscopy confirmed that the non-polar/polar copolymerized stationary phase C4/HC-3 structure of this example was:
  • the silane reagent added dropwise in this example was a mixture of 12 mmol (4.8 mL) of octadecyltrichlorosilane and 12 mmol (1.8 mL) of 3-chloropropyltrichlorosilane. Elemental analysis results: C 16.24%, H 3.03%; infrared spectrum: characteristic absorption peak at 2900-2800 cm-1. Elemental analysis and infrared spectroscopy results confirmed that the non-polar/polar copolymerized stationary phase C18/HC-1 structural formula of this example was:
  • the silane reagent added dropwise in this example was a mixture of 8 mmol (3.2 mL) of octadecyltrichlorosilane and 16 mmol (2.4 mL) of 3-chloropropyltrichlorosilane. Elemental analysis results: C 14.37%, H 2.71%; Infrared spectrum: Characteristic absorption peak at 2900-2800 cm-1. Elemental analysis and infrared spectroscopy results confirmed that the non-polar/polar copolymerized stationary phase C18/HC-G5 structure of this example was:
  • the silane reagent added dropwise in this example was 200 mmol (80.0 mL) of octadecyltrichlorosilane and 2 mmol (1.2 mL) of a mixture of p-sulfonic acid phenethyltrichlorosilane. Elemental analysis results: C 24.41%, H 5.32%; Infrared spectrum: Characteristic absorption peak at 2900-2800 cm-1 confirms the non-polar/polar copolymerization phase of the present embodiment.
  • the C18/SCX-100S structural formula is:
  • spherical silica gel (particle size 5 urn, pore size 30 nm, specific surface area 80 m2 / g), placed at 1000 In a mL glass flask, 700 mL of a 10% strength hydrochloric acid solution was added, and the mixture was heated under reflux for 12 hours, cooled to room temperature, filtered, washed with water until neutral, and dried at 150 ° C for 24 hours.
  • the dried silica gel was placed in a 500 mL three-neck glass bottle, and nitrogen gas having a relative humidity of 50% was continuously supplied for 48 hours to obtain a hydrated silica gel 40.5 go. Under the condition of passing dry nitrogen, 300 mL of dry water was added to the hydrated silica gel.
  • Example 15 The remainder of the preparation was the same as in Example 15 except that the silane reagent added was 18 mmol (4.2 mL) of octyltrichlorosilane and 6 mmol (0.9 mL) of 3-chloropropyltrichlorosilane. Elemental analysis results: C 3.75%, H 0.92%; Infrared spectrum: Characteristic absorption peak at 2900-2800 cm-1. Elemental analysis and infrared spectroscopy confirmed that the non-polar/polar copolymerized stationary phase C8/HC-3L structural formula of this example was:
  • spherical silica gel (particle size 5 ⁇ , pore size 10 nm, specific surface area 305 m2 / g), placed in a 250 mL glass flask, add 150 mL of a 10% hydrochloric acid solution, and heat to reflux for 12 hours. Cool to room temperature, filter, wash to neutral, and dry at 150 ° C for 24 hours. The dried silica gel was placed in a 150 mL three-neck glass bottle, and nitrogen gas with a relative humidity of 50% was continuously supplied for 48 hours to obtain a hydrated silica gel. 10.5 go. Under the condition of passing dry nitrogen, 80 mL of the hydrated silica gel was added to dry.
  • the dried solid was placed in a 200 mL three-necked flask, and 100 mL of toluene was added, followed by 3.8 mL of trimethylchlorosilane, 7.0 mL of hexamethyldisilazane and 2.0 mL of pyridine, and the mixture was heated to 110 ° C to stir the reaction. End-sealing treatment for 24 hours.
  • the reaction system was filtered, washed successively with dichloromethane, methanol, water, tetrahydrofuran, and methanol, and the product was dried at 80 ° C for 12 hours to obtain a separation material of the formula.
  • stop flow rate test is as follows: Balance the column with 10 mM ammonium formate solution for 10 minutes, run the sample, collect the data as Befroe stop flow chromatogram; then stop the flow rate for 30 minutes, and re-equilibrate the column with 10 mM ammonium formate solution. 10 minutes, the injection run, the data collected is the After stop flow chromatogram.
  • Mobile phase conditions mobile phase enthalpy, 0.1% formic acid water, mobile phase B, ACN; gradient conditions for C18HCE column: 0-30 min, 0% ⁇ 30% B; gradient conditions for XBridge C18 column: 0-30 min, 5% ⁇ 35% B; 30-40 min, 35% ⁇ 60% B;
  • the separation material C18/SCX-10S obtained in Example 13 was packed with a solid phase extraction (SPE) cartridge and subjected to solid phase extraction of melamine to test the adsorption performance of the separation material on melamine.
  • SPE solid phase extraction
  • the results indicate that the separation material has a good adsorption capacity for melamine, and is suitable as a reverse phase/ion exchange mixed mode solid phase extraction filler.
  • the solid phase extraction conditions are:
  • SPE cartridge volume l mL, filled with 60 mg of separation material
  • Sample aqueous melamine solution, concentration 0.5 mg/mL
  • Activate the SPE column Rinse the SPE column with 2 mL of methanol and 2 mL of water in sequence, the flow rate is less than 1 mL/min; Load: Add 1 mL of the melamine aqueous solution sample to the SPE cartridge;
  • the chromatographic conditions are:

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  • Chemical & Material Sciences (AREA)
  • Analytical Chemistry (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Silicon Polymers (AREA)
  • Solid-Sorbent Or Filter-Aiding Compositions (AREA)

Abstract

L'invention porte sur une matière de séparation basée sur un substrat de type gel de silice et sur son procédé de préparation. La matière de séparation basée sur un substrat de type gel de silice, qui est obtenue par la copolymérisation de deux ou plus de deux réactifs silanes sur la surface de gel de silice pour former une « phase stationnaire co-polymérisée non polaire/polaire », est représentée par la formule suivante, dans laquelle NP désigne des groupes non polaires qui comprennent des groupes n-alcanes en C1-30, phényle, et ainsi de suite; P désigne des groupes polaires qui comprennent des groupes n-alcanes en C1-12 unis à un groupe Cl, Br, CN, amino, un groupe benzène sulfonique, un groupe sulfonique, un groupe carboxyle, un groupe ammonium quaternaire, un groupe alcool, et ainsi de suite. Le procédé de préparation de la matière de séparation susmentionnée comporte les étapes suivantes : le prétraitement d'acidification du gel de silice, l'hydratation, la copolymérisation d'un mélange d'un réactif silane non polaire et d'un réactif silane polaire sur la surface du gel de silice hydraté, la filtration, le lavage, le séchage, et ainsi de suite. La matière de séparation de la présente invention présente à la fois des groupes non polaires et des groupes polaires, qui permettent de fournir une force appliquée hydrophobe et plusieurs sortes de forces appliquées polaires, et améliorent ainsi considérablement la sélectivité de séparation et d'enrichissement. La matière de séparation obtenue par le procédé de préparation de la présente invention présente des avantages tels que des groupes de liaison uniformes et stables sur la surface, une plus grande fixation et ainsi de suite, et peut être appliquée à la chromatographie liquide et l'extraction en phase solide.
PCT/CN2010/073468 2009-07-31 2010-06-02 Matière de séparation basée sur du gel de silice ayant une réaction de copolymérisation en surface et son procédé de préparation Ceased WO2011012019A1 (fr)

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CH706332A1 (de) * 2012-03-28 2013-09-30 Zeochem Ag Dotierte Materialien für die Umkehrphasen-Chromatographie.
CN104001347A (zh) * 2014-05-13 2014-08-27 齐鲁工业大学 一种亲水性广谱固相萃取柱的制备方法
CN104275155A (zh) * 2014-10-28 2015-01-14 武汉大学 一种新型镉离子印迹磁性介孔硅胶固相萃取剂的制备方法与应用
US10618920B2 (en) 2016-06-03 2020-04-14 Agilent Technologies, Inc. Functionalized particles having modified phases
CN112237898A (zh) * 2019-07-17 2021-01-19 上海安谱实验科技股份有限公司 一种强阴离子型固相萃取柱填料及其制备方法
CN112892505A (zh) * 2019-12-04 2021-06-04 中国科学院大连化学物理研究所 一种表面电荷改性的反相色谱分离材料及制备和应用

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