EP1458475A2 - Optisch aktive trägermaterialien, herstellungsverfahren dafür und verwendung davon - Google Patents

Optisch aktive trägermaterialien, herstellungsverfahren dafür und verwendung davon

Info

Publication number
EP1458475A2
EP1458475A2 EP02805798A EP02805798A EP1458475A2 EP 1458475 A2 EP1458475 A2 EP 1458475A2 EP 02805798 A EP02805798 A EP 02805798A EP 02805798 A EP02805798 A EP 02805798A EP 1458475 A2 EP1458475 A2 EP 1458475A2
Authority
EP
European Patent Office
Prior art keywords
poly
optically active
support material
material according
ethylene
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.)
Ceased
Application number
EP02805798A
Other languages
English (en)
French (fr)
Inventor
Raphael Duval
Hubert Leveque
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Nouryon Pulp and Performance Chemicals AB
Original Assignee
Eka Chemicals AB
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Eka Chemicals AB filed Critical Eka Chemicals AB
Publication of EP1458475A2 publication Critical patent/EP1458475A2/de
Ceased legal-status Critical Current

Links

Classifications

    • 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
    • B01D15/38—Selective adsorption, e.g. chromatography characterised by the separation mechanism involving specific interaction not covered by one or more of groups B01D15/265 - B01D15/36
    • B01D15/3833—Chiral chromatography
    • 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
    • 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
    • B01J20/02—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof comprising inorganic material
    • B01J20/04—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof comprising inorganic material comprising compounds of alkali metals, alkaline earth metals or magnesium
    • B01J20/041—Oxides or hydroxides
    • 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
    • B01J20/02—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof comprising inorganic material
    • B01J20/06—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof comprising inorganic material comprising oxides or hydroxides of metals not provided for in group B01J20/04
    • 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
    • B01J20/02—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof comprising inorganic material
    • B01J20/10—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof comprising inorganic material comprising silica or silicate
    • B01J20/14—Diatomaceous earth
    • 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
    • B01J20/02—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof comprising inorganic material
    • B01J20/10—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof comprising inorganic material comprising silica or silicate
    • B01J20/16—Alumino-silicates
    • B01J20/165—Natural alumino-silicates, e.g. zeolites
    • 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
    • B01J20/02—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof comprising inorganic material
    • B01J20/20—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof comprising inorganic material comprising free carbon; comprising carbon obtained by carbonising processes
    • 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
    • B01J20/22—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof comprising organic material
    • 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
    • B01J20/22—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof comprising organic material
    • B01J20/24—Naturally occurring macromolecular compounds, e.g. humic acids or their derivatives
    • 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
    • B01J20/22—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof comprising organic material
    • B01J20/26—Synthetic macromolecular compounds
    • B01J20/261—Synthetic macromolecular compounds obtained by reactions only involving 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
    • B01J20/22—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof comprising organic material
    • B01J20/26—Synthetic macromolecular compounds
    • B01J20/262—Synthetic macromolecular compounds obtained otherwise than by reactions only involving carbon to carbon unsaturated bonds, e.g. obtained by polycondensation
    • 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
    • B01J20/22—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof comprising organic material
    • B01J20/26—Synthetic macromolecular compounds
    • B01J20/264—Synthetic macromolecular compounds derived from different types of monomers, e.g. linear or branched copolymers, block copolymers, graft copolymers
    • 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
    • B01J20/22—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof comprising organic material
    • B01J20/26—Synthetic macromolecular compounds
    • B01J20/265—Synthetic macromolecular compounds modified or post-treated polymers
    • B01J20/267—Cross-linked 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
    • B01J20/28—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof characterised by their form or physical properties
    • B01J20/28002—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 physical properties
    • B01J20/28004—Sorbent size or size distribution, e.g. particle size
    • 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
    • B01J20/28—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof characterised by their form or physical properties
    • B01J20/28014—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 form
    • B01J20/28016—Particle form
    • 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
    • B01J20/28—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof characterised by their form or physical properties
    • 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
    • B01J20/28078—Pore diameter
    • 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
    • B01J20/29—Chiral phases
    • 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
    • B01J20/3092—Packing of a container, e.g. packing a cartridge or column
    • 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
    • B01J20/3202—Impregnating or coating ; Solid sorbent compositions obtained from processes involving impregnating or coating characterised by the carrier, support or substrate used for impregnation or coating
    • B01J20/3204—Inorganic carriers, supports or substrates
    • 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
    • B01J20/3202—Impregnating or coating ; Solid sorbent compositions obtained from processes involving impregnating or coating characterised by the carrier, support or substrate used for impregnation or coating
    • B01J20/3206—Organic carriers, supports or substrates
    • B01J20/3208—Polymeric carriers, supports or substrates
    • B01J20/321—Polymeric carriers, supports or substrates consisting of a polymer obtained by reactions 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
    • B01J20/3202—Impregnating or coating ; Solid sorbent compositions obtained from processes involving impregnating or coating characterised by the carrier, support or substrate used for impregnation or coating
    • B01J20/3206—Organic carriers, supports or substrates
    • B01J20/3208—Polymeric carriers, supports or substrates
    • B01J20/3212—Polymeric carriers, supports or substrates consisting of a polymer 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
    • B01J20/3214—Impregnating or coating ; Solid sorbent compositions obtained from processes involving impregnating or coating characterised by the method for obtaining this coating or impregnating
    • B01J20/3217—Resulting in a chemical bond between the coating or impregnating layer and the carrier, support or substrate, e.g. a covalent bond
    • 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
    • B01J20/3274—Proteins, nucleic acids, polysaccharides, antibodies or antigens
    • 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
    • B01J20/3276—Copolymers
    • 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
    • B01J20/3282—Crosslinked 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
    • B01J2220/00—Aspects relating to sorbent materials
    • B01J2220/40—Aspects relating to the composition of sorbent or filter aid materials
    • B01J2220/46—Materials comprising a mixture of inorganic and organic materials
    • 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
    • B01J2220/40—Aspects relating to the composition of sorbent or filter aid materials
    • B01J2220/48—Sorbents characterised by the starting material used for their preparation
    • B01J2220/4812—Sorbents characterised by the starting material used for their preparation the starting material being of organic character
    • B01J2220/4825—Polysaccharides or cellulose materials, e.g. starch, chitin, sawdust, wood, straw, cotton
    • 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
    • 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
    • B01J2220/58—Use in a single column
    • 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
    • C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
    • C08G2261/30—Monomer units or repeat units incorporating structural elements in the main chain
    • C08G2261/33—Monomer units or repeat units incorporating structural elements in the main chain incorporating non-aromatic structural elements in the main chain
    • C08G2261/332—Monomer units or repeat units incorporating structural elements in the main chain incorporating non-aromatic structural elements in the main chain containing only carbon atoms

Definitions

  • optically active support materials constituted by one or more esters and / or one or more carbamates and / or one or more mixed ester and carbamate compounds of polysaccharide or oligosaccharide, and an organic support and / or mineral.
  • the invention also relates to their preparation process and their uses for the optical enrichment of chiral molecules, and more particularly for the separation of enantiomers by liquid, supercritical, gas or gas / liquid chromatography.
  • the support materials of the invention When used in a chromatographic process, the support materials of the invention, also called enantioselective chromatographic support materials, constitute unichiral stationary phases, or “PSCs”, also called enantioselective, or optically active stationary phases, and the the technique used is then called chiral or enantioselective chromatography.
  • PSCs unichiral stationary phases
  • enantioselective chromatographic support materials constitute unichiral stationary phases, or “PSCs”, also called enantioselective, or optically active stationary phases, and the technique used is then called chiral or enantioselective chromatography.
  • Enantioselective chromatography has experienced considerable growth during the last twenty armies, both for analytical applications, but also for the preparation on an industrial scale, of unichiral or optically active pharmaceutical molecules of high enantiomeric purity.
  • ester and carbamate derivatives of polysaccharides although very broad in terms of chromatographic resolution of molecules of extremely varied chemical structures, is limited by the fact that said ester and carbamate derivatives of polysaccharides are physically deposited and / or linked by covalent bond to silica.
  • silica and more particularly silica gels, which are soluble in basic aqueous media and in the presence of fluoride ions.
  • EP957358 describes stationary chiral phases whose performance is improved by the presence of a remaining quantity of solvent for deposition on the solid support.
  • the Depositing Company has found, quite surprisingly and unexpectedly, that the chemical nature of the support on which a polysaccharide ester or carbamate derivative is placed in order to form an enantioselective chromatographic support material, or PSC, has a direct influence on the enantioselectivity factor of the PSC thus constituted.
  • ester derivative or more ester derivatives, or else from one or more carbamate derivatives, or alternatively from one or more mixed ester and carbamate derivatives d oligosaccharide or polysaccharide, to have a whole range of different PSCs, made from support materials of different chemical nature, and having a different enantioselectivity factor with respect to the same racemic molecule, or else d '' a same mixture of enantiomers to separate.
  • the invention therefore relates to an optically active support material constituted by one or more ester derivatives, and / or by one or more carbamate derivatives, and / or by one or more mixed ester and carbamate derivatives of polysaccharides or oligosaccharides, and by a solid support of organic and / or mineral origin, said solid support not being able to be chosen from the group comprising silica gel, alumina, magnesia, titanium oxide, glass, kaolin , silicates, chromium oxide, boron oxide, zirconia, clay, polyvinyl alcohols, carbon, polyamide, polystyrene, polyacrylate and polyacrylamide.
  • the solid support is of organic origin, it is an organic polymer chosen from the group comprising in particular poly (substituted styrenes), polyolefins, polyvinyl ethers, polyalkylvinyl ketones, polyalkynes, polyisocyanates, polyisonitriles, polyoxiranes, polythiiranes, polyaziridines, polyesters, polythioesters, polyurethanes, polyureas, polysulfonamides, phenol / fomaldehyde, polyacenaphthylene, poly (acrylamide-co-acrylic acid), poly- (acrylamide-co-diallyl dimethyl ammonium chloride) resins ), poly- (2- acrylamido-2-methyl-1-propane sulfonic acid), poly- (2-acrylamido-2-methyl-1- propane sulfonic acid -co-acrylonitrile), poly (2-acrylamido-2 acid -methyl-l- sulfonic
  • polyacrylonitrile poly (acrylonitrile-co-butadiene), poly (acrylonitrile-co-butadiene-co-acrylic acid), poly (acrylonitrile-co-butadiene-co-styrene), poly (acrylonitrile-co-methacrylonitrile), poly (acrylonitrile-co-methylacrylate), poly- (acrylonitrile-co-vinylidenechloride-co-methylmethacrylate), poly (allylamine), poly (amide-imide), polyaniline, poly (aspartic acid), poly (azelaic anhydride), polyaziridine, poly (benzyl methacrylate), poly (bisphenol A carbonate), poly (bisphenol A-co-epichlorohydrin), poly (4-bromostyrene), poly (l-butene), poly (tert-butyl acrylate-co-ethylacrylate-co- methacrylic acid), poly (1,4-butylene
  • polymer is used interchangeably for polymers and copolymers.
  • the solid support is of organic and mineral origin, it can be chosen from all types of existing organic and mineral-based composite materials, such as, for example, silica / dextran or hydroxyapatite / agarose composites.
  • the solid support is of mineral origin, it is chosen from the group comprising magnesium silicate, zeolites, diatomaceous earths, phosphates such as calcium, zirconium, titanium, hafiiium, germanium phosphates , tin or lead, arsenates such as titanium, zirconium or tin arsenates, ceramics such as titanium oxide / magnesium oxide, alumina / silicon oxide, zirconia / silicon oxide, apatites like fiuoroapatite or hydroxyapatite.
  • magnesium silicate such as calcium, zirconium, titanium, hafiiium, germanium phosphates , tin or lead
  • arsenates such as titanium, zirconium or tin arsenates
  • ceramics such as titanium oxide / magnesium oxide, alumina / silicon oxide, zirconia / silicon oxide, apatites like fiuoroapatite or hydroxyapatite.
  • the supports whether of organic or mineral origin, or both of organic and mineral origin (composite) can be in the form of particles having a diameter of 1 ⁇ m to 10 mm and pores having a diameter from 1 to 4000 ⁇ .
  • ester or carbamate derivatives or the mixed ester and carbamate derivatives of polysaccharides and oligosaccharides used in the constitution of the optically active support material according to the invention have the following general formula: PS - (OZ) n (I)
  • PS represents a polysaccharide or an oligosaccharide having at least 6 sugar units
  • n varies from 12 to 30,000, each OZ group being able to represent independently of each other OH, -OC (O) -NH-R or -OC (O) - R, with R representing an alkyl, aryl, alkylaryl or arylalkyl group having 1 to 40 carbon atoms, optionally substituted by at least one heteroatom chosen from the group comprising in particular sulfur, nitrogen, oxygen, phosphorus, chlorine, fluorine, bromine, iodine and silicon.
  • R is chosen from the group comprising phenyl, tolyl, 3,5-dimethylphenyl, 4-chlorophenyl, 3,5-dichlorophenyl and 4-tertio butylphenyl.
  • PS when in formula (I) PS represents a polysaccharide, it is chosen from the group comprising in particular cellulose, amylose, starch, chitosan, having an average degree of polymerization of 20 to 10,000 .
  • PS represents an oligosaccharide
  • this is preferably chosen from the group comprising ⁇ , ⁇ and ⁇ -cyclodextrins.
  • the optically active support material according to the invention comprises 2 to 70% by weight of the ester or carbamate derivative or of the mixed ester derivative and polysaccharide and oligosaccharide carbamate, and 30 to 98% by weight of said solid support.
  • the ester derivative (s), and / or the carbamate derivative (s), and / or the mixed ester and carbamate derivative (s) of polysaccharide or oligosaccharide are not linked by a covalent bond to the support d organic and / or mineral origin and are not chemically linked to each other, that is to say are not crosslinked.
  • the support of organic origin is one of the polymers mentioned above and can also be polyamide or a polyvinyl alcohol.
  • the support is of mineral origin, in this first embodiment, it is as described above and can also be chromium oxide, boron oxide, aluminum silicate, clay and carbon.
  • the enantioselective supports in accordance with this first embodiment are prepared by physical deposition of the ester or carbamate derivative or of the mixed ester and carbamate derivative of polysaccharide or oligosaccharide on the solid support of organic and / or mineral origin.
  • This physical deposition can be done in two different ways, namely: evaporation of a suspension, produced from the solid support and from a solution of said ester and / or carbamate derivative of polysaccharide or oligosaccharide, at ordinary pressure or under vacuum, at room temperature or by heating,
  • the invention also relates to a process for the preparation of the optically active support material in accordance with the first embodiment described above which presents the successive stages consisting in: dissolving a compound of formula (I) in a polar organic protic or aprotic solvent, adding to the solution obtained a solid support according to the invention and perfectly homogenize the suspension obtained, evaporate the solvent at ordinary pressure and / or under vacuum, at a temperature ranging from room temperature to approximately 100 ° C., or else gently add to the suspension obtained in the preceding step a non-solvent for the compound of formula (I), dry at room temperature or by heating, at ordinary pressure or under vacuum the optically active support material obtained.
  • the preferred organic solvents of the ester and / or carbamate derivatives of polysaccharide or oligosaccharide are tetrahydrofuran, 1,4-dioxane, pyridine, and the preferred non-solvents are heptane, hexane and alkanes in general , alcohol and water.
  • the compound of general formula (I) is dissolved preferably in a protic solvent, so as not to dissolve or excessively swell the part organic polymer, on the other hand, when the support is of mineral origin, the compound of formula (I) is dissolved either in a polar organic protic or aprotic solvent.
  • the ester derivative (s) and / or the carbamate derivative (s) and / or the mixed ester and carbamate derivative (s) of polysaccharide or oligosaccharide are linked by a covalent chemical bond to a support of organic and / or mineral origin, the solid support having optionally been chemically modified beforehand with a bifunctional agent.
  • the solid support is chemically modified beforehand if it does not contain groups capable of forming covalent bonds with the derivative ester or carbamate or the mixed ester and carbamate derivative of polysaccharide or oligosaccharide.
  • the support of organic origin is one of the polymers mentioned above and can also be polyamide or a polyvinyl alcohol.
  • the support is of mineral origin, in this second embodiment, it is as described above and can also be clay or carbon.
  • the enantioselective supports in accordance with this second embodiment are prepared using a method as described above which further comprises, before or after the drying step, a reaction step consisting in creating a covalent bond between the solid support and the ester and / or carbamate derivative or the mixed ester and carbamate derivative, as described in "Journal of Chromatography A, 839, 15-21, 1999".
  • ester derivative (s) and / or the carbamate derivative (s) and / or the mixed ester and carbamate derivative (s) of polysaccharide or the oligosaccharide are not linked by a covalent bond to the original support organic and / or mineral but are chemically linked to each other, that is to say are crosslinked.
  • the support of organic origin is one of the polymers mentioned above and can also be polyamide.
  • the support is of mineral origin, in this third embodiment, it is as described above and can also be aluminum silicate, chromium oxide or boron oxide.
  • the enantioselective supports in accordance with this third embodiment are prepared using a process comprising the steps consisting in physically depositing the compounds of formula (I) on a solid support which is inert with respect to it. ci, that is to say a solid support which does not contain reactive functions making it possible to create a covalent bond with the compound of formula (I) as described in connection with the first embodiment, then with polymerize the compounds of formula (I) with one another, optionally using bi- or polyfunctional crosslinking agents.
  • the crosslinking step can be carried out using bifunctional agents as indicated in US patents 6,342,592, EP0985681 and US5,302,633.
  • the ester derivative (s) and / or the carbamate derivative (s) and / or the mixed ester and carbamate derivative (s) of polysaccharide or oligosaccharide are linked by a covalent chemical bond to the support of organic origin and / or mineral and are also chemically bonded to each other, that is to say crosslinked
  • the support is of mineral origin
  • it is as described above and can also be the aluminum silicate, chromium oxide or boron oxide.
  • the enantioselective supports in accordance with this fourth embodiment are prepared using a method as described in connection with the first embodiment which further comprises a step of forming a covalent bond, a step of crosslinking which are performed in any order before or after the drying step.
  • ester derivative (s) and / or the carbamate derivative (s) and / or the mixed ester and carbamate derivative (s) of polysaccharide or oligosaccharide are fixed by covalent bond to the solid support of organic and mineral origin, as described for example in the "Journal of chromatography A, 839,
  • the invention also relates to the use of an optically active support material, for removing from a mixture of at least two constituents, chosen from the group comprising organic, mineral or organo-mineral molecules, at least part of one of these constituents, or to separate the said constituents by a chromatographic method. It also relates to the use of the optically active support material, to remove from a mixture of at least two enantiomers, chosen from the group comprising organic, inorganic or organomineral molecules, at least part of one of these constituents , to enrich the mixture with one of the enantiomers and thus obtain the other enriched enantiomer, that is to say of a rotary power greater than that of the initial mixture.
  • the invention also relates to the use of the optically active support material, for separating enantiomers by a chromatographic method.
  • the invention is illustrated by the following examples which are not limiting.
  • Examples I to VI illustrate the first embodiment of the enantioselective supports in accordance with the invention.
  • EXAMPLE I a / Preparation of a tris-2,3,6- (3,5-dimethylphenyl carbamate cellulose
  • microcrystalline cellulose (average degree of polymerization n of 100), 75 ml of pyridine and 38 ml of heptane are placed in a reactor. Agitation and heating at reflux make it possible to dehydrate the cellulose by azeotropic entrainment. 8.15 g of 3,5-dimethylphenylisocyanate and 0.05 g of dimethylaminopyridine are added and the medium is brought to reflux for 24 hours.
  • a polyamide support marketed by Merck under the reference 32
  • CDMPC tetrahydrofuran
  • the THF is then slowly evaporated at ordinary pressure and then under vacuum until a perfectly dry and homogeneous powder is obtained.
  • the column is inserted into an HPLC system and the entire system is then balanced under the following conditions: temperature 20 ° C., elution rate 1 ml / min, detection wavelength 254 nm, variable eluting mobile phase ( see table of results), quantity of racemic mixture injected: 1 ⁇ g, 25 ⁇ l injection loop, ethanol injection solvent.
  • elution rate 1 ml / min
  • detection wavelength 254 nm
  • variable eluting mobile phase see table of results
  • quantity of racemic mixture injected 1 ⁇ g, 25 ⁇ l injection loop, ethanol injection solvent.
  • microcrystalline cellulose (average degree of polymerization n of 100), 75 ml of pyridine and 38 ml of heptane are placed in a reactor. Agitation and heating at reflux make it possible to dehydrate the cellulose by azeotropic entrainment. 10.42 g of 3,5-dichlorophenylisocyanate and 0.05 g of dimethylaminopyridine are added and the medium is brought to reflux for 24 hours.
  • the solution is cooled and then poured onto 100 ml of methanol.
  • the precipitate is washed with 300 ml of methanol and then dried under vacuum at 50 ° C.
  • Biosepra is dried at 150 ° C under vacuum.
  • CDMPCs prepared in step a / of Example I, are then dissolved in 40 ml of tetrahydrofuran or THF. 3 g of previously dried titanium support are added to the previous solution and the suspension obtained is perfectly homogenized with stirring.
  • the solid is dried at ordinary pressure and then under vacuum until a perfectly dry and homogeneous powder is obtained.
  • PSCs were prepared from cellulose tris-2,3,6- (3,5-dimethylphenyl) carbamate, or CDMPC, which was synthesized as in step a / of Example I and various references solid supports.
  • the solid supports used are magnesium silicate and titanium oxide. They are of chromatographic quality and consist of irregular particles of 5 to 15 ⁇ m having a pore diameter varying from 200 to 2000 ⁇ .
  • the cellulose carbamate derivative obtained, or CDMPC was physically deposited by evaporation from a tetrahydrofuran solution, at a content of 15% by weight relative to the support.
  • each enantioselective chromatographic support material obtained was conditioned in a chromatographic column of dimensions 100 ⁇ 4.6 mm (length ⁇ internal diameter).
  • PSCs were prepared from cellulose tris-2,3,6- (3,5-dimethylphenyl) carbarnate, or CDMPC, which was synthesized as in step a / of Example I and from different supports solid.
  • the solid supports used are silica gel, magnesium silicate and zeolite.
  • Silica gel consists of irregular particles of 5 to 15 ⁇ m having a pore diameter varying from 200 to 2000 ⁇ .
  • the magnesium silicate used is Florisil (Supelco / Aldrich catalog reference 288705) sieved between 5 and 10 ⁇ m.
  • the zeolite comes from FLUKA (reference 9606).
  • the cellulose carbamate derivative obtained, or CDMPC was physically deposited by evaporation from a tetrahydrofuran solution, at a content of 15% by weight relative to the support silica gel and magnesium silicate and at a content of 5 % by weight relative to the zeolite support.
  • each enantioselective chromatographic support material obtained was conditioned in a chromatographic column of dimensions 250 x 4.6 mm (length x internal diameter).
  • Example V The procedure is the same as in Example V, except that a solid support is used, a polystyrene / divinylbenzene from the company Purolite (5 ⁇ m / 2000 ⁇ ).
  • test conditions are identical to those described above and the eluting mobile phase consists of a heptane / isopropanol 90/10 mixture:
  • EXAMPLE VII Enantioselective solid support in accordance with the fourth embodiment of the invention a / Preparation of a mixed tris-2 amyloidosis. 3, 6- (3, 5-dimethylphenylcarbamate and 4-vinylbenzoate).
  • zeolite from FLUKA, reference 9606 are dehydrated by azeotropic entrainment at reflux in 50 ml of toluene. 3 g of ⁇ -mercaptopropyltrimethoxysilane are added all at once and the reaction suspension is brought to reflux for 72 hours. The suspension is filtered and the solid is washed with 2 x 50 ml of toluene. After drying at 60 ° C. under vacuum, 6.25 g of mercaptopropyl derivative zeolite are obtained.
  • the solid is taken up in 20 ml of tetrahydrofuran and 80 ml of heptane and 2 ml of ethanedithiol are added as well as 10 mg of AIBN (azo-bis-isobutyronitrile). The suspension is brought to reflux for 10 minutes.
  • AIBN azo-bis-isobutyronitrile
  • the precipitate is filtered and then washed with 3 x 20 ml of boiling tretrahydrofuran then 3 x 20 ml of heptane.
  • the solid is then suspended in 30 ml of heptane and is then conditioned in a chromatographic column of 100 mm x 4.6 mm (length x diameter).
  • the column is conditioned in heptane / isopropanol 90/10 at a flow rate of 1 ml / mm and the detection is carried out at 254 nm. 10 ⁇ g of racemic solutes are injected.
  • the enantioselectivity of the separation is calculated after measurement of the chromatographic parameters and the calculation of the selectivity factor ⁇ .
  • magnesium silicate (reference 288705, absorbent Florisil from the company SUPELCO) are dehydrated by azeotropic entrainment at reflux in 50 ml of toluene.
  • the column obtained is conditioned in pure chloroform.
  • the eluting phase and pure chloroform which is percolated through the column at a flow rate of 1 ml / min.
  • the enantioselectivity of the separation is calculated after measurement of chromatographic parameters and calculation of the selectivity factor ⁇ .
  • EXAMPLE IX Enantioselective support in accordance with the second embodiment of the invention a / Preparation of a mixed tris-2 amyloidosis. 3, 6- (3, 5-dimethylphenylcarbamate and 4-vinylbenzoate. 2.5 g of amylose (average degree of polymerization of 100), 75 ml of pyridine and 38 ml of heptane are placed in a reactor. amylose is dehydrated by azeotropic entrainment, the suspension medium is cooled, then 6 g of 3,5-dimethylphenyl isocyanate and 3 g of 4-vinylbenzoyl chloride are successively added.
  • the solid is taken up in 20 ml of tetrahydrofuran and 80 ml of heptane and 10 mg of AIBN (azo-bis-isobutyronitrile) are added. The suspension is brought to reflux for 10 minutes. The precipitate is filtered and then washed with 3 x 20 ml of boiling tretrahydrofuran then 3 x 20 ml of heptane. The solid is then suspended in 30 ml of heptane and is then conditioned in a chromatographic column of 100 mm x 4.6 mm (length x diameter). The column is conditioned in pure chloroform at a flow rate of 1 ml / mm and the detection is carried out at 254 nm. 10 ⁇ g of racemic solutes are injected. The enantioselectivity of the separation is calculated after measurement of the chromatographic parameters and the calculation of the selectivity factor ⁇ .
  • AIBN azo-bis-isobutyronitrile

Landscapes

  • Chemical & Material Sciences (AREA)
  • Analytical Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Chemistry (AREA)
  • Inorganic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Molecular Biology (AREA)
  • General Health & Medical Sciences (AREA)
  • Biochemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Geochemistry & Mineralogy (AREA)
  • Solid-Sorbent Or Filter-Aiding Compositions (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
EP02805798A 2001-12-27 2002-12-17 Optisch aktive trägermaterialien, herstellungsverfahren dafür und verwendung davon Ceased EP1458475A2 (de)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
FR0116933A FR2834227A1 (fr) 2001-12-27 2001-12-27 Materiaux supports optiquement actifs, leur procede de preparation et leurs utilisations
FR0116933 2001-12-27
PCT/FR2002/004391 WO2003055594A2 (fr) 2001-12-27 2002-12-17 Materiaux supports optiquement actifs, leur procede de prepartion et leurs utilisations

Publications (1)

Publication Number Publication Date
EP1458475A2 true EP1458475A2 (de) 2004-09-22

Family

ID=8871026

Family Applications (1)

Application Number Title Priority Date Filing Date
EP02805798A Ceased EP1458475A2 (de) 2001-12-27 2002-12-17 Optisch aktive trägermaterialien, herstellungsverfahren dafür und verwendung davon

Country Status (9)

Country Link
US (1) US7597804B2 (de)
EP (1) EP1458475A2 (de)
JP (1) JP2005513492A (de)
KR (1) KR20040078656A (de)
CN (1) CN1617762A (de)
AU (1) AU2002364659B2 (de)
FR (1) FR2834227A1 (de)
NO (1) NO20043125L (de)
WO (1) WO2003055594A2 (de)

Families Citing this family (28)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR20060132711A (ko) * 2004-02-03 2006-12-21 다이셀 가가꾸 고교 가부시끼가이샤 초임계 유체 크로마토그래피를 사용한 광학 이성질체의분리 방법
DE102007043366A1 (de) * 2007-09-12 2009-03-19 Degudent Gmbh Verfahren zur Positionsbestimmung eines intraoral messenden Messgerätes
WO2009137058A1 (en) 2008-05-06 2009-11-12 Metabolix, Inc. Biodegradable polyester blends
JP5775072B2 (ja) * 2009-06-17 2015-09-09 ボード・オブ・リージエンツ，ザ・ユニバーシテイ・オブ・テキサス・システム 分離剤としてのシクロフルクタン用の組成物および方法
US8951807B2 (en) 2010-01-15 2015-02-10 Bio-Rad Laboratories, Inc. Surface neutralization of apatite
US8895707B2 (en) 2010-08-18 2014-11-25 Bio-Rad Laboratories, Inc. Elution of proteins from hydroxyapatite resins without resin deterioration
EP2670704B1 (de) 2011-02-02 2018-12-12 Bio-Rad Laboratories, Inc. Apatitoberflächenneutralisierung mit alkalischen lösungen
CN102205770B (zh) * 2011-03-16 2013-09-25 北京培宏望志科技有限公司 将平面图片中的影像做成立体实物的方法
EP2855501B1 (de) 2012-05-30 2018-04-25 Bio-Rad Laboratories, Inc. In-situ-wiederherstellung von apatitbasierten chromatografieharzen
US9302203B2 (en) * 2012-07-20 2016-04-05 Mitsubishi Chemical Corporation Chromatographic separation material
US9475930B2 (en) 2012-08-17 2016-10-25 Metabolix, Inc. Biobased rubber modifiers for polymer blends
CN103105442B (zh) * 2013-01-18 2014-06-18 华侨大学 凝胶渗透色谱检测高分子嵌段共聚物结构参数的方法
CN103111271B (zh) * 2013-03-04 2014-10-15 福州大学 一种壳聚糖接枝β-环糊精键合硅胶吸附剂的制备方法
US10669417B2 (en) 2013-05-30 2020-06-02 Cj Cheiljedang Corporation Recyclate blends
WO2015149029A1 (en) 2014-03-27 2015-10-01 Metabolix, Inc. Highly filled polymer systems
CN103962106B (zh) * 2014-06-03 2016-09-14 湖南大学 一种壳聚糖/腐植酸修饰的磁性吸附剂去除废水中铅的方法
CN105392569B (zh) 2014-06-23 2019-08-20 生物辐射实验室股份有限公司 磷灰石预处理
EP3157551B1 (de) 2014-06-23 2023-02-15 Bio-Rad Laboratories, Inc. In-situ-restaurierung von apatit
JP6810039B2 (ja) 2015-07-31 2021-01-06 株式会社ダイセル 超臨界流体クロマトグラフィー用の固定相
CN106582580A (zh) * 2016-12-22 2017-04-26 苏州楚博生物技术有限公司 层析柱用耐高压亲和层析介质
CN106475074A (zh) * 2016-12-22 2017-03-08 苏州楚博生物技术有限公司 高机械强度亲和层析介质
CN107376656A (zh) * 2017-07-13 2017-11-24 杭州水处理技术研究开发中心有限公司 一种基于墨鱼骨纳米粒子改性的高通量反渗透膜的制备方法
CN107252638A (zh) * 2017-07-13 2017-10-17 杭州水处理技术研究开发中心有限公司 一种含有改性墨鱼骨纳米粒子的高通量纳滤膜的制备方法
CN110548494B (zh) * 2019-10-11 2020-10-09 湖北工业大学 一种利用动植物废料制备磁性吸附材料的方法
CN111662791A (zh) * 2020-06-08 2020-09-15 江苏欣捷衬布有限公司 一种活性染料染色衬布的低温清洁化皂洗剂及制备方法
CN113231047A (zh) * 2020-09-18 2021-08-10 董晓明 一种吸附剂在去除含锑印染废水中的应用
CN112778437B (zh) * 2020-12-31 2022-07-15 北京科华微电子材料有限公司 一种天然多糖改性树脂及其制备方法和应用、光刻胶
CN115999522A (zh) * 2023-01-05 2023-04-25 昆明医科大学 一种硅胶@聚苯胺@多糖衍生物csp填料及其制备方法和应用

Family Cites Families (39)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS5247355B2 (de) * 1974-10-15 1977-12-01
US4335017A (en) * 1975-12-15 1982-06-15 United Kingdom Atomic Energy Authority Composite materials comprising deformable xerogel within the pores of particulate rigid supports useful in chromatography
EP0147804B2 (de) 1983-12-28 2001-01-03 Daicel Chemical Industries, Ltd. Verfahren zur Trennung optischer und geometrischer Isomere
JPS60142930A (ja) * 1983-12-28 1985-07-29 Daicel Chem Ind Ltd 分離剤
US4724207A (en) * 1984-02-02 1988-02-09 Cuno Incorporated Modified siliceous chromatographic supports
US4694044A (en) * 1984-03-09 1987-09-15 Research Development Corp. Of Japan Adsorbent
JPS60196663A (ja) 1984-03-19 1985-10-05 Daicel Chem Ind Ltd 分離剤
JPS60226831A (ja) * 1984-04-02 1985-11-12 Daicel Chem Ind Ltd 分離剤
JPS60226832A (ja) * 1984-04-02 1985-11-12 Daicel Chem Ind Ltd 多糖の脂肪族エステルを含む分離剤
US4861872A (en) * 1986-03-20 1989-08-29 Daicel Chemical Industries, Ltd. Alkyl-phenylcarbamate derivative of polysaccharide
JPS62278450A (ja) 1986-05-28 1987-12-03 Chuichi Hirayama 光学分割剤
DE3850148T2 (de) * 1987-03-04 1994-09-22 Daicel Chem Alkylphenylcarbamatderivat von einem Polysaccharid.
FR2616437B1 (fr) * 1987-06-11 1990-09-07 Ibf Polymeres composites, leur preparation et leur utilisation en chromatographie liquide
JPH01199643A (ja) * 1988-01-30 1989-08-11 Mitsubishi Kasei Corp 光学分割用吸着剤
JPH01216943A (ja) * 1988-02-26 1989-08-30 Mitsui Toatsu Chem Inc 光学分割用分離剤
US5302633A (en) * 1990-11-29 1994-04-12 Nacalai Tesque, Inc. Optical resolution agent and process for the preparation of the same
US5268097A (en) * 1992-06-19 1993-12-07 Sepracor Inc. Passivated and stabilized porous mineral oxide supports and method for the preparation and use of same
SE500248C2 (sv) * 1992-12-03 1994-05-24 Eka Nobel Ab Kirala adsorbenter och framställning av dessa samt föreningar på vilka adsorbenterna är baserade och framställning av dessa föreningar
JPH06308108A (ja) * 1993-04-27 1994-11-04 Showa Denko Kk クロマトグラフィー用吸着担体及びその製造方法
JP3190206B2 (ja) 1993-06-22 2001-07-23 ダイセル化学工業株式会社 光学異性体用分離剤およびその製造法
DE69408795D1 (de) 1993-11-29 1998-04-09 Nippon Oil Co Ltd Verfahren zur Herstellung von Kohlenstoff/Kohlenstoffverbundmaterial
JP3493706B2 (ja) 1994-02-15 2004-02-03 昭和電工株式会社 クロマトグラフィー用吸着担体
ATE217859T1 (de) * 1994-02-25 2002-06-15 Daicel Chem Verfahren zur herstellung von optisch aktiven mevalonolactonen
JPH07260762A (ja) * 1994-03-17 1995-10-13 Daicel Chem Ind Ltd 高速液体クロマトグラフィー用充填剤及びその製造法
US5502022A (en) * 1994-05-16 1996-03-26 Biosepra, Inc. Chromatography adsorbents utilizing mercapto heterocyclic ligands
JP3611343B2 (ja) 1994-06-02 2005-01-19 ダイセル化学工業株式会社 擬似移動層式クロマト分離装置における光学異性体分離のモニター方法、擬似移動層式クロマト分離装置および擬似移動層式クロマト分離方法
JP3188102B2 (ja) * 1994-06-07 2001-07-16 ダイセル化学工業株式会社 多糖誘導体の製造方法
US6011149A (en) 1995-03-07 2000-01-04 Novartis Ag Photochemically cross-linked polysaccharide derivatives as supports for the chromatographic separation of enantiomers
TW362100B (en) 1995-07-21 1999-06-21 Novartis Ag The preparation and use of photochemically cross-linked polysaccharide derivatives having no photopolymerisable functional groups
DE69637415T2 (de) * 1995-12-21 2008-05-21 Daicel Chemical Industries, Ltd. Füllmaterial für sehr schnelle flüssigkeitschromatographie
JPH09194399A (ja) 1996-01-23 1997-07-29 Ube Ind Ltd カラム用光学分割剤
FR2760752A1 (fr) 1997-03-14 1998-09-18 Inst Francais Du Petrole Composes chiraux, leur synthese et leur utilisation en support
US5811532A (en) * 1997-06-30 1998-09-22 Uop Llc Covalently bound, polysaccharide-based chiral stationary phases
FR2767834B1 (fr) 1997-08-29 1999-12-03 Inst Francais Du Petrole Mono et di-derives de cyclodextrines, leurs synthese et purification et leur utilisation en support
JP4320068B2 (ja) * 1997-10-03 2009-08-26 ダイセル化学工業株式会社 光学異性体用分離剤及びその製造法
FR2784108A1 (fr) 1998-09-11 2000-04-07 Inst Francais Du Petrole Nouveaux polymeres reticules a base de derives bis-silanes, bis-thioethers, bis-sulfoxydes, bis-sulfones et butane di-yl de polysaccharides et d'oligosaccharides, et leur mise en forme en materiaux supports
FR2784109B1 (fr) 1998-09-11 2003-09-26 Inst Francais Du Petrole Derives chloro-, hydroxy-, et alkoxysilanes de polysaccharides ou d'oligosaccharides, polymerisables et reticulables, leur synthese et leur utilisation comme sources de nouveaux materiaux supports
JP3635002B2 (ja) 2000-04-18 2005-03-30 ダイセル化学工業株式会社 液体クロマトグラフィー用光学異性体分離用充填剤
AU2002350258A1 (en) * 2001-11-27 2003-06-23 Ciphergen Biosystems, Inc. Composite chromatographic sorbent of mineral oxide beads with hydroxyapatite-filled pores

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See references of WO03055594A2 *

Also Published As

Publication number Publication date
AU2002364659A1 (en) 2003-07-15
US7597804B2 (en) 2009-10-06
KR20040078656A (ko) 2004-09-10
CN1617762A (zh) 2005-05-18
WO2003055594A2 (fr) 2003-07-10
AU2002364659B2 (en) 2008-02-28
NO20043125L (no) 2004-09-27
FR2834227A1 (fr) 2003-07-04
US20050209100A1 (en) 2005-09-22
WO2003055594A3 (fr) 2003-12-24
JP2005513492A (ja) 2005-05-12

Similar Documents

Publication Publication Date Title
EP1458475A2 (de) Optisch aktive trägermaterialien, herstellungsverfahren dafür und verwendung davon
Stalcup et al. (S)-2-Hydroxyprophyl-β-cyclodextrin, a new chiral stationary phase for reversed-phase liquid chromatography
US7749389B2 (en) Filler used for separating optical isomers and process for separating optical isomers with the filler
JPH0475213B2 (de)
EP0978498B1 (de) Trennmittel für optische isomere und verfahren zu ihrer herstellung
EP0899272A1 (de) Mono und Di-Derivate von Cyclodextrine, deren Synthese und Reinigung und deren Verwendung als Träger
JPH0475214B2 (de)
US8053543B2 (en) Filler for optical isomer separation
Krause et al. Improved chiral stationary phase based on cellulose triacetate supported on non-macroporous silica gel diol for the high-performance liquid chromatographic separation of racemic flavanones and diastereomeric flavanone glycosides
US7615150B2 (en) Separation agent for separating optical isomer and method for preparation thereof
EP0738284B1 (de) Polysaccharidderivate und deren verwendung zur herstellung chiraler stationärer phasen zur trennung von isomeren
Hilton et al. Comparison of the enantioselectivity of phenethyl-and naphthylethyl-carbamate substituted cyclodextrin bonded phases
KR101013252B1 (ko) 크로마토그래피용 분리제 및 그의 제조 방법
JPH0442371B2 (de)
WO2003026793A2 (fr) Reseau polymere tridemensionnel reticule, son procede de preparation, materiau support comportant ce reseau et leurs utilisations
Lienne et al. Optimization of the direct chiral separation of potential cytotoxic α-methylene-γ-butyrolactones and α-methylene-γ-butyrolactams by liquid chromatography
JPS6082858A (ja) 光学分割用吸着剤
Guntari et al. Fabrication of chiral stationary phases via continuous assembly of polymers for resolution of enantiomers by liquid chromatography
WO1992012180A1 (fr) Polymeres cyclodextrine-epichlorhydrine utilisables pour la separation et l'adsorption de substances
Ghanem et al. Chiral recognition ability and solvent versatility of bonded amylose tris (3, 5‐dimethylphenylcarbamate) chiral stationary phase: Enantioselective liquid chromatographic resolution of racemic N‐alkylated barbiturates and thalidomide analogs
JPH0426639A (ja) ２―シクロヘキセン―１―オールの光学分割方法
JPH0671170A (ja) カラム用分離剤
Félix et al. An amylopectin tris (phenylcarbamate) chiral stationary phase for high performance liquid chromatography
WO2003085000A9 (fr) Derives de polysaccharides reticules sur un support et leur mode d'obtention
FR2810978A1 (fr) Procede de dedoublement de l'intermediaire tetralone de la sertraline

Legal Events

Date Code Title Description
PUAI Public reference made under article 153(3) epc to a published international application that has entered the european phase

Free format text: ORIGINAL CODE: 0009012

17P Request for examination filed

Effective date: 20040623

AK Designated contracting states

Kind code of ref document: A2

Designated state(s): AT BE BG CH CY CZ DE DK EE ES FI FR GB GR IE IT LI LU MC NL PT SE SI SK TR

AX Request for extension of the european patent

Extension state: AL LT LV MK RO

RIN1 Information on inventor provided before grant (corrected)

Inventor name: LEVEQUE, HUBERT

Inventor name: DUVAL, RAPHAEL

17Q First examination report despatched

Effective date: 20050629

REG Reference to a national code

Ref country code: DE

Ref legal event code: R003

STAA Information on the status of an ep patent application or granted ep patent

Free format text: STATUS: THE APPLICATION HAS BEEN REFUSED

18R Application refused

Effective date: 20121023