WO2004002618A1 - Materiau adsorbant et procede de preparation de celui-ci - Google Patents

Materiau adsorbant et procede de preparation de celui-ci Download PDF

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Publication number
WO2004002618A1
WO2004002618A1 PCT/SE2003/001118 SE0301118W WO2004002618A1 WO 2004002618 A1 WO2004002618 A1 WO 2004002618A1 SE 0301118 W SE0301118 W SE 0301118W WO 2004002618 A1 WO2004002618 A1 WO 2004002618A1
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WIPO (PCT)
Prior art keywords
adsorbent material
support
polymer
hydrogen
alkyl
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PCT/SE2003/001118
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English (en)
Inventor
Per Möller
Domingo Sanchez
Peter Gidlund
Börje S. PERSSON
Lars Jonsson
Original Assignee
Akzo Nobel N.V.
Eka Chemicals Ab
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Application filed by Akzo Nobel N.V., Eka Chemicals Ab filed Critical Akzo Nobel N.V.
Priority to JP2004517453A priority Critical patent/JP4219327B2/ja
Priority to AU2003243105A priority patent/AU2003243105A1/en
Priority to EP03761886A priority patent/EP1515800A1/fr
Publication of WO2004002618A1 publication Critical patent/WO2004002618A1/fr

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Classifications

    • 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
    • B01J20/3202—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
    • B01J20/3214—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
    • B01J20/3219—Resulting in a chemical bond between the coating or impregnating layer and the carrier, support or substrate, e.g. a covalent bond involving a particular spacer or linking group, e.g. for attaching an active 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
    • B01J20/30—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
    • B01J20/3276—Copolymers

Definitions

  • the present invention relates to an adsorbent material. It also relates to a method of preparing an adsorbent material, and the use of the adsorbent material in chromatographic separation methods.
  • a stationary phase When using chromatography for separating individual chemical compounds present in a mixture, the choice of a stationary phase is important to get good resolution, i.e., good separation of the compounds.
  • stationary phases There is a wide variety of stationary phases available, which have different affinities to different compounds. More specifically, it is usually the surface of the stationary phase that interacts with the components of the mobile phase in a desired manner, i.e., the stationary phase acts as an adsorbent material. Silica, or other inorganic oxides, can be used as the base material for stationary phases in chromatography.
  • a specific organic compound may be attached to the surface by reaction with e.g. silanol groups on a silica surface.
  • silica and other inorganic oxides may start to dissolve at high pH, causing leakage of inorganic material, usually referred to as inorganic leakage.
  • inorganic leakage it is important to cover as much of the support surface as possible.
  • the support is suitably a porous material having pores of various sizes. The main part of the surface area of the support material is the area within the pores. It is therefore important that this part can be coated with, e.g., a polymer, to avoid inorganic leakage and to give good resolution.
  • chromatographic stability of an adsorbent material is also an important factor.
  • chromatographic stability is herein meant the ability of the adsorbent material to keep its selectivity and retention over a period of use.
  • Polymers may also be attached to a support surface by first attaching a monomer onto the support surface followed by further polymerisation.
  • H. Engelhardt et al. Chemically Modified Surfaces, Proc. Symp 4 th , Elsevier, 1992, 225-241 , discloses a method of coating a solid support where a vinylsilane is bonded to a silica surface followed by co-polymerisation of acrylamide onto the vinyl group of the covalently attached vinylsilane.
  • this will give a predominantly tentacle-type coating where most polymer chains are attached in a single point, with each polymer chain extending from the support as a "tentacle", giving a both chemically and mechanically unstable attachment.
  • a coating and e.g. silica is often unstable, especially at low pH, which may give leakage of organic material, usually referred to as organic leakage.
  • organic leakage when polymerising vinyl monomers onto a solid support, remaining monomers may be present on the support surface giving chemical instability.
  • a preformed polymer may be attached onto a support surface in multiple points.
  • WO 98/27418 A1 discloses a method of coating a silica support by first binding a coupling agent onto the support surface and thereafter binding a preformed polymer to the coupling agent.
  • the preformed polymer comprises a totally saturated carbon chain with leaving groups. It is a rather complicated method requiring several process steps.
  • Kurganov et al Journal of Chromatography 261 (1983) 223-233, discloses a method for bonding a copolymer of styrene and methylvinyldimethoxysilane onto a surface of silica.
  • the reactivity of methylvinyldimethoxysilane is much lower than for styrene, which will favour homopolymerisation of styrene giving only few silane monomer parts in the copolymer, thereby effecting the number of linkages to the silica in a disadvantageous way.
  • a chloromethylated polystyrene is reacted with aminopropylthethoxysilane and thereafter bonded to a surface of silica.
  • U.S. patent 4,914,159 discloses a process for immobilising copolymers of (meth)acrylamides onto a silica gel.
  • a (meth)acrylamide monomer is copolymerised with a silylating agent such as methacryloyloxypropyltrimethoxysilane.
  • adsorbent material for chromatography which has high chromatographic stability, which gives excellent resolution of chemical compounds to be separated from a mixture and which has a high degree of surface coverage of the solid support.
  • a method for preparing an adsorbent material for chromatography which comprises few steps, which gives an adsorbent material with high degree of surface coverage of the solid support, and which enables flexibility in providing adsorbent materials with different chromatographic behaviour.
  • an adsorbent material for chromatography having chromatographic stability, having a high degree of surface coverage of a support, giving excellent resolution, and which can be tailor-made for a desired separation characteristic, can be provided.
  • the adsorbent material for chromatography comprises a polymer immobilised onto a support, wherein the polymer backbone is attached to the support by one or more linkages which comprise one or more amide groups.
  • the present invention further comprises a method of preparing an adsorbent material for chromatography comprising immobilising a polymer onto a support, wherein the support is reacted with the polymer, thereby forming one or more linkages between the polymer backbone and the support, each linkage comprises one or more amide groups.
  • the present invention comprises a method of preparing an adsorbent material for chromatography comprising providing a polymer from a monomer mixture comprising an amide group containing silane, reacting the polymer with a support to form one or more linkages between the polymer backbone and the support.
  • the polymer is suitably added as a solution to a suspension of the support.
  • the support is suitably filtered off, washed, and dried.
  • a further acid treatment step is also suitably performed, suitably followed by an end-capping step wherein an end-capping agent, for example, chloro-trimethylsilane, hexamethyldisilazane or (N,N-dimethylamino)-trimethylsilane, is added to the support.
  • an end-capping agent for example, chloro-trimethylsilane, hexamethyldisilazane or (N,N-dimethylamino)-trimethylsilane
  • the present invention further comprises the use of the adsorbent material for chromatography in chromatographic separation methods. It also comprises the use of an adsorbent material for chromatography prepared according to any of the methods of the present invention, in chromatographic separation methods.
  • chromatographic separation methods can be, for example, HPLC, supercritical fluid chromatography (SFC), and simulating moving bed (SMB).
  • the present invention further comprises a method of separating chemical compounds from a mixture comprising contacting the mixture with the adsorbent material for chromatography according to the present invention.
  • the support material of the present invention is suitably a material whose surface comprises groups susceptible to reaction with groups on the polymer.
  • the support material can be either an organic or an inorganic material.
  • Organic support materials include polymeric support materials such as poly(styrene-divinyl benzene), polyacrylate resins and poiyacrylamide resins.
  • Organic support materials, such as polymeric support materials are suitably functionalised to comprise groups, such as hydroxyl groups, halogen groups, amino groups, or vinyl groups, susceptible to reaction with the polymer to be immobilised onto the support.
  • Inorganic support materials include inorganic oxides.
  • the surface of inorganic support materials comprises hydroxyl groups or groups convertible to hydroxyl groups.
  • the support is an inorganic support, preferably an inorganic oxide such as alumina, titania, zirconia, chromia, silica, boria, toria, beryllia, silica-alumina and combinations thereof. Most preferably, the support is silica.
  • the support material can be a particulate material, or, in the form of a piece, a sheet, a rod or a capillary coating.
  • the support material is a particulate material, suitably having a volume average particle size of from about 0.5 to about 500 ⁇ m, preferably from about 0.7 to about 200 ⁇ m, most preferably from about 1 to about 40 ⁇ m.
  • the particles are preferably substantially spherical.
  • the particulate material suitably comprises pores.
  • the pore size, pore volume and specific surface area of the particulate support material may vary depending on the type of support material used, the characteristics of the polymer to be linked to the support and the desired separation characteristics when in use.
  • the pore size range may be different for diffusion pores and perfusion pores (flow pores).
  • the pore size is suitably from about 20 to about 4000 A, preferably from about 50 to about 500 A.
  • the pore size is suitably from about 1000 to about 80000 A, preferably from about 5000 to about 50000 A.
  • the pore volume is suitably from about 0.1 to about 4 ml/g, preferably from about 0.3 to about 2 ml/g, most preferably from about 0.5 to about 1.5 ml/g.
  • the specific surface area is suitably from about 1 to about 1000 m 2 /g, preferably from about 25 to about 700 m 2 /g. most preferably from about 100 to about 500 m 2 /g.
  • the polymer of the present invention suitably comprises groups susceptible to reaction with the support.
  • groups can be, for example, vinyl groups, alkoxy groups such as methoxy, ethoxy, propoxy, butoxy and isobutoxy, halogens such as chlorine, bromine, iodine, and fluorine, secondary amino groups such as dialkylamine, an imidazol group, a morpholine group, or an azide group.
  • the polymer is a preformed polymer, preferably a co-polymer.
  • the polymer is suitably prepared by polymerising a monomer mixture comprising at least one vinyl monomer mi of the general formula (I):
  • desired separation characteristics is herein meant that a certain resolution between a specific chemical compound of interest and other compounds is achieved.
  • R 7 the affinity of the adsorbent material to certain chemical compounds will be different. For example, properties such as hydrophobic-, dipol-dipol-, ⁇ - ⁇ -, electrostatic-, and steric interactions, or chiral discrimination can be varied.
  • R 7 is any of C C 3 o alkyl, CrC 30 hydroxyalkyl, C C 3 o alkylcarboxyl, and C C 30 aminoalkyl, preferably C C 10 alkyl, C!-C 10 hydroxyalkyl, C C 10 alkylcarboxyl, and C ⁇ CTM aminoalkyl is used, most preferably C 1 -C5 alkyl, Ci-Cs hydroxyalkyl, C 1 -C 5 alkylcarboxyl, and C 1 -C 5 aminoalkyl.
  • the monomer mixture suitably further comprises at least one vinyl monomer m 3 of the general formula (III):
  • ITH is preferably a monomer comprising a silane group.
  • the silane group is suitably of the general formula (IV):
  • B is C C alkyl, C C alkoxy, halogen, hydroxyl, hydrogen, -N(R 3 ) Z (R 4 ) 2-Z , an imidazol group, a morpholine group, or an azide group
  • D is C C alkyl
  • y 1-3
  • z 1-2
  • R 3 and R 4 are, independently from each other, hydrogen, C C 20 alkyl, or aryl.
  • Preferred monomers m-i are (meth)acrylamido alkylalkoxysilanes such as (meth)acrylamidopropyl- trimethoxysilane, (meth)acrylamidopropyldimethoxymethylsilane, (meth)acrylamidopropyl- dimethoxyethylsilane, (meth)acrylamidopropyl-monomethoxydimethylsilane, (meth)acryl- amidopropylmonomethoxydiethylsilane, (meth)acrylamidopropyltriethoxysilane,
  • (meth)acrylamidobutyl-diethoxyethylsilane (meth)acrylamidobutylmonoethoxy- dimethylsilane, (meth)acrylamidobutylmonoethoxydiethylsilane, (meth)acrylamidoalkyl- aminosilanes such as (meth)acrylamidodimethylaminosilane, and (meth)acryl- amidodiethylaminosilane, (meth)acrylamidoalkylhalogensilanes such as (meth)acryl- amidodimethylchlorosilane, (meth)acrylamidodiethylchlorosilane, (meth)acryl- amidodipropylchlorosilane, (meth)acryl-amidomethyldichlorosilane (meth)acrylamidoethyl- dichlorosilane, and (meth)acrylamido-propyldichlorosi
  • Examples of preferred (meth)acrylamide-based monomers m 2 are functionalised, or non-functionalised, C ⁇ -C 30 alkylbutyl(meth)acrylamides such as propyl(meth)acrylamide, isopropyl(meth)acrylamide, butyl(meth)acrylamide, tert- butyl(meth)acrylamide, pentyl(meth)acrylamide, hexyl(meth)acrylamide, heptyl(meth)acrylamide, octyl(meth)-acrylamide, nonyl(meth)acrylamide, decyl(meth)acrylamide, and, octadecyl(meth)-acrylamide.
  • C ⁇ -C 30 alkylbutyl(meth)acrylamides such as propyl(meth)acrylamide, isopropyl(meth)acrylamide, butyl(meth)acrylamide, tert- butyl(meth)acrylamide, pentyl(
  • Examples of preferred monomers m 3 are bis-acrylamides such as N,N'- ethylenebis-acrylamide, N,N'-propylenebis-acrylamide, and, N,N'-butylenebis-acrylamide.
  • the monomers, mi, m 2 and m 3 are suitably selected so that a random distribution of monomers in the polymer is achieved.
  • the polymer suitably comprises from about 1 to about 100 mole % of units of monomer m,, preferably from about 10 to about 90 mole %, most preferably from about 30 to about 70 mole %.
  • the polymer suitably comprises from 0 to about 99 mole % of units of monomer m 2 , preferably from about 10 to about 90 mole %, most preferably from about 30 to about 70 mole %. Furthermore, the polymer suitably comprises from 0 to about 99 mole % of units of monomer m 3 , preferably from 0 to about 50 mole %.
  • the weight average molecular weight of the polymer is suitably from about 1000 to about 500000 g/mole, preferably from about 1500 to about 100000 g/mole, most preferably from about 2000 to about 25000 g/mole.
  • the number of monomer units per polymer chain is suitably from about 5 to about 2000, preferably from about 8 to about 500, most preferably from about 10 to about 100.
  • the polymer is suitably prepared by polymerising the monomers in an organic solvent in the presence of an initiator, and optionally a chain-transfer agent such as a ercapto compound.
  • the solvent may be any organic solvent suitable as polymerisation medium and includes xylene, toluene, dioxane, tetrahydrofurane, chlorinated hydrocarbons, benzene, dimethylformamide, and N-methylpyrrolidone.
  • suitable initiators include peroxides and azo-compounds.
  • the polymer of the present invention is suitably covalently bonded to the support material.
  • a preformed polymer which is a copolymer of an acrylamide monomer comprising silane and alkoxy groups and a further acrylamide monomer is covalently bonded to the surface of a silica particle.
  • the polymer is suitably reacted with the support material by preparing a mixture from a suspension of the support material in a solvent with a solution of the polymer.
  • the solvent used to suspend the support material is suitably an organic solvent.
  • the amount support material added to the solvent is from about 0.01 to about 1 g support material /ml solvent, preferably from about 0.05 to about 0.5 g/ml.
  • the amount polymer, added to the support material is a measurement of the degree of surface coverage of the support material.
  • the amount polymer added to the support material is suitably from about 0.5 to about 20 ⁇ mole of monomer per m 2 support material surface, preferably from about 1 to about 15 ⁇ mole of monomer per m 2 support material surface, even more preferably from about 4 to about 12 ⁇ mole of monomer per m 2 support material surface, most preferably from about 6 to about 10 ⁇ mole of monomer per m 2 support material surface.
  • the support material comprises pores, the amount polymer added to the support material may also be dependent on the pore size of the support material.
  • the amount polymer added to the support material, calculated as monomers within the polymer is preferably from about 3 to about 10 ⁇ mole of monomer per m 2 support material surface.
  • the amount polymer added to the support material, calculated as monomers within the polymer is preferably from about 5 to about 12 ⁇ mole of monomer per m 2 support material surface.
  • the amount polymer added to the support material, calculated as monomers within the polymer is preferably from about 7 to about 15 ⁇ mole of monomer per m 2 support material surface.
  • the temperature during the reaction is suitably from about 10 to about 200°C, preferably from about 50 to about 160°C.
  • the mixture is kept under inert atmosphere.
  • silica particles of the type Kromasil® having a volume average particle size of 5 ⁇ m, a pore size of 100 A, and a specific surface area of 330 m 2 /g, were suspended in 30 ml xylene.
  • 12 ml of the polymer solution of example 1 was added and the mixture was left for 18 hours at 140 °C under inert atmosphere.
  • the particles were thereafter filtered off, washed and dried.
  • the particles were analysed by elemental analysis to comprise 13.7 % carbon and 1.53 % nitrogen, which corresponds to a coverage of 4.5 ⁇ mole/m 2 , calculated as ⁇ mole/m 2 of monomers included in the polymer.
  • the formula for calculating the surface coverage is: N c 10 6 / [(14 x 100 x n c - (N c x M - N c )) x S], wherein N c is the measured nitrogen weight percentage, n c is the number of nitrogen atoms in the monomer of the polymer bonded to silica, M is the average molecular weight of the monomer(s) included in the polymer, and S is the specific surface area of the silica.
  • Example 3 The same procedure as in example 2 was employed, but with using silica particles of the type Kromasil® having a volume average particle size of 5 ⁇ m, a pore size of 200 A, and a specific surface area of 213 m 2 /g. The particles were analysed to comprise 11.3 % carbon and 1.285 % nitrogen, which corresponds to a surface coverage of 5.2 ⁇ mole/m 2 .
  • Example 5 The same procedure as in example 2 was employed, but with using silica particles of the type Kromasil® having a volume average particle size of 5 ⁇ m, a pore size of 300 A, and a specific surface area of 77 m 2 /g. The particles were analysed to comprise 5.75 % carbon and 0.735 % nitrogen, which corresponds to a surface coverage of 7.6 ⁇ mole/m 2 .
  • Example 5
  • Example 6 5.5 g N-(monomethoxy-dimethyl-propylsilyl) acrylamide and 7.0 g n-butyl acrylamide were dissolved in 100 ml xylene. This solution was added into a reaction vessel together with a peroxide initiator dissolved in 45 ml xylene. The polymerisation was performed during 6 hours under inert atmosphere at 140°C. The resulting polymer had a weight average molecular weight of 2500 Dalton. The conversion of monomers was more than 98%.
  • silica particles of the type Kromasil® having a volume average particle size of 5 ⁇ m, a pore size of 100 A, and a specific surface area of 330 m 2 /g, were suspended in 150 ml polymer solution made according to example 5. The mixture was left for 18 hours at 140 °C under inert atmosphere. The particles were thereafter filtered off, washed and dried. The particles were analysed by elemental analysis to comprise
  • Example 7 The same procedure as in example 7 was employed, except that a polymer solution made according to example 6 was used.
  • the particles were analysed by elemental analysis to comprise 16.7 % carbon and 2.5 % nitrogen, which corresponds to a surface coverage of 7.0 ⁇ mole/m 2 , calculated as ⁇ mole/m 2 of monomers included in the polymer.

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  • Chemical & Material Sciences (AREA)
  • Analytical Chemistry (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Inorganic Chemistry (AREA)
  • Solid-Sorbent Or Filter-Aiding Compositions (AREA)
  • Treatment Of Liquids With Adsorbents In General (AREA)
  • Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)

Abstract

L'invention concerne un matériau adsorbant destiné à la chromatographie et comprenant un polymère immobilisé sur un support, le squelette du polymère étant fixé sur le support au moyen d'un ou de plusieurs éléments de liaison comprenant un ou plusieurs groupes amide. L'invention concerne également un procédé de préparation d'un matériau adsorbant destiné à la chromatographie consistant à faire réagir un support avec un polymère.
PCT/SE2003/001118 2002-06-27 2003-06-26 Materiau adsorbant et procede de preparation de celui-ci WO2004002618A1 (fr)

Priority Applications (3)

Application Number Priority Date Filing Date Title
JP2004517453A JP4219327B2 (ja) 2002-06-27 2003-06-26 吸着材料及び吸着材料の調製方法
AU2003243105A AU2003243105A1 (en) 2002-06-27 2003-06-26 Adsorbent material and method of preparing an adsorbent material
EP03761886A EP1515800A1 (fr) 2002-06-27 2003-06-26 Materiau adsorbant et procede de preparation de celui-ci

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EP02445088 2002-06-27
EP02445088.4 2002-06-27

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WO2004002618A1 true WO2004002618A1 (fr) 2004-01-08

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WO2013184796A1 (fr) * 2012-06-08 2013-12-12 Illumina, Inc. Revêtements polymères
EP3021114A4 (fr) * 2013-07-08 2016-07-27 Nat Univ Corp Kyoto Inst Tech Agent de séparation
EP3845307A4 (fr) * 2018-08-30 2021-11-03 Daicel Corporation Phase stationnaire pour la chromatographie

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CN108165119A (zh) * 2012-06-08 2018-06-15 Illumina公司 聚合物包被
CN108165119B (zh) * 2012-06-08 2020-09-04 Illumina公司 聚合物包被
US9012022B2 (en) 2012-06-08 2015-04-21 Illumina, Inc. Polymer coatings
KR101559983B1 (ko) 2012-06-08 2015-10-13 일루미나, 인코포레이티드 중합체 코팅
US11702694B2 (en) 2012-06-08 2023-07-18 Illumina, Inc. Polymer coatings
US9752186B2 (en) 2012-06-08 2017-09-05 Illumina, Inc. Polymer coatings
CN104508060A (zh) * 2012-06-08 2015-04-08 Illumina公司 聚合物包被
WO2013184796A1 (fr) * 2012-06-08 2013-12-12 Illumina, Inc. Revêtements polymères
US10954561B2 (en) 2012-06-08 2021-03-23 Illumina, Inc. Polymer coatings
EP3792320A1 (fr) * 2012-06-08 2021-03-17 Illumina, Inc. Revêtements polymères
US10266891B2 (en) 2012-06-08 2019-04-23 Illumina, Inc. Polymer coatings
US11285458B2 (en) 2013-07-08 2022-03-29 National University Corporation Kyoto Institute Of Technology Separating agent
EP3021114A4 (fr) * 2013-07-08 2016-07-27 Nat Univ Corp Kyoto Inst Tech Agent de séparation
EP3845307A4 (fr) * 2018-08-30 2021-11-03 Daicel Corporation Phase stationnaire pour la chromatographie

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EP1515800A1 (fr) 2005-03-23
AU2003243105A1 (en) 2004-01-19
JP4219327B2 (ja) 2009-02-04
JP2005536719A (ja) 2005-12-02

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