CA1302614C - Polymeres composites, leur preparation et leur utilisation en chromatographie liquide - Google Patents
Polymeres composites, leur preparation et leur utilisation en chromatographie liquideInfo
- Publication number
- CA1302614C CA1302614C CA000569262A CA569262A CA1302614C CA 1302614 C CA1302614 C CA 1302614C CA 000569262 A CA000569262 A CA 000569262A CA 569262 A CA569262 A CA 569262A CA 1302614 C CA1302614 C CA 1302614C
- Authority
- CA
- Canada
- Prior art keywords
- acrylic
- allylic
- weight
- acrylamide
- vinyl
- 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.)
- Expired - Lifetime
Links
- 229920000642 polymer Polymers 0.000 title claims abstract description 22
- 239000002131 composite material Substances 0.000 title claims abstract description 10
- 238000004811 liquid chromatography Methods 0.000 title claims description 6
- 238000002360 preparation method Methods 0.000 title claims description 3
- 239000000178 monomer Substances 0.000 claims abstract description 23
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims abstract description 22
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims abstract description 16
- 229920002554 vinyl polymer Polymers 0.000 claims abstract description 16
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims abstract description 12
- 238000004132 cross linking Methods 0.000 claims abstract description 8
- 230000001588 bifunctional effect Effects 0.000 claims abstract description 6
- 239000000377 silicon dioxide Substances 0.000 claims abstract description 6
- 229920001577 copolymer Polymers 0.000 claims abstract description 4
- 125000000746 allylic group Chemical group 0.000 claims description 17
- 238000006116 polymerization reaction Methods 0.000 claims description 16
- 239000004115 Sodium Silicate Substances 0.000 claims description 10
- NTHWMYGWWRZVTN-UHFFFAOYSA-N sodium silicate Chemical compound [Na+].[Na+].[O-][Si]([O-])=O NTHWMYGWWRZVTN-UHFFFAOYSA-N 0.000 claims description 10
- 229910052911 sodium silicate Inorganic materials 0.000 claims description 10
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 claims description 9
- 238000000034 method Methods 0.000 claims description 9
- 239000012985 polymerization agent Substances 0.000 claims description 6
- HGINCPLSRVDWNT-UHFFFAOYSA-N Acrolein Chemical compound C=CC=O HGINCPLSRVDWNT-UHFFFAOYSA-N 0.000 claims description 4
- VVJKKWFAADXIJK-UHFFFAOYSA-N Allylamine Chemical compound NCC=C VVJKKWFAADXIJK-UHFFFAOYSA-N 0.000 claims description 4
- WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 claims description 4
- 239000002253 acid Substances 0.000 claims description 4
- 239000003795 chemical substances by application Substances 0.000 claims description 4
- WZISPVCKWGNITO-UHFFFAOYSA-N 4-(diethylamino)-2-methylidenebutanamide Chemical compound CCN(CC)CCC(=C)C(N)=O WZISPVCKWGNITO-UHFFFAOYSA-N 0.000 claims description 3
- -1 acryloyl .beta.-alanine Chemical compound 0.000 claims description 3
- 239000007788 liquid Substances 0.000 claims description 3
- FQPSGWSUVKBHSU-UHFFFAOYSA-N methacrylamide Chemical compound CC(=C)C(N)=O FQPSGWSUVKBHSU-UHFFFAOYSA-N 0.000 claims description 3
- PQWVIUSCFLEBHJ-UHFFFAOYSA-N n-[1,3-dihydroxy-2-(hydroxymethyl)propan-2-yl]-2-methylprop-2-enamide Chemical compound CC(=C)C(=O)NC(CO)(CO)CO PQWVIUSCFLEBHJ-UHFFFAOYSA-N 0.000 claims description 3
- MVBJSQCJPSRKSW-UHFFFAOYSA-N n-[1,3-dihydroxy-2-(hydroxymethyl)propan-2-yl]prop-2-enamide Chemical compound OCC(CO)(CO)NC(=O)C=C MVBJSQCJPSRKSW-UHFFFAOYSA-N 0.000 claims description 3
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims description 2
- KUDUQBURMYMBIJ-UHFFFAOYSA-N 2-prop-2-enoyloxyethyl prop-2-enoate Chemical compound C=CC(=O)OCCOC(=O)C=C KUDUQBURMYMBIJ-UHFFFAOYSA-N 0.000 claims description 2
- NFKIMJJASFDDJG-UHFFFAOYSA-N 5-amino-N,N-diethyl-2-methylpent-2-enamide Chemical compound NCCC=C(C(=O)N(CC)CC)C NFKIMJJASFDDJG-UHFFFAOYSA-N 0.000 claims description 2
- SAQWCPXBLNGTCC-UHFFFAOYSA-N 6-(prop-2-enoylamino)hexanoic acid Chemical compound OC(=O)CCCCCNC(=O)C=C SAQWCPXBLNGTCC-UHFFFAOYSA-N 0.000 claims description 2
- LZCXCXDOGAEFQX-UHFFFAOYSA-N N-Acryloylglycine Chemical compound OC(=O)CNC(=O)C=C LZCXCXDOGAEFQX-UHFFFAOYSA-N 0.000 claims description 2
- CNCOEDDPFOAUMB-UHFFFAOYSA-N N-Methylolacrylamide Chemical compound OCNC(=O)C=C CNCOEDDPFOAUMB-UHFFFAOYSA-N 0.000 claims description 2
- 229920006243 acrylic copolymer Polymers 0.000 claims description 2
- 125000004386 diacrylate group Chemical group 0.000 claims description 2
- YQCFXPARMSSRRK-UHFFFAOYSA-N n-[6-(prop-2-enoylamino)hexyl]prop-2-enamide Chemical compound C=CC(=O)NCCCCCCNC(=O)C=C YQCFXPARMSSRRK-UHFFFAOYSA-N 0.000 claims description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims 3
- 239000004971 Cross linker Substances 0.000 claims 1
- 229920006063 Lamide® Polymers 0.000 claims 1
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims 1
- 239000012736 aqueous medium Substances 0.000 claims 1
- FCDZZFLRLVQGEH-UHFFFAOYSA-N ethane-1,2-diol;prop-2-enoic acid Chemical compound OCCO.OC(=O)C=C FCDZZFLRLVQGEH-UHFFFAOYSA-N 0.000 claims 1
- 239000002609 medium Substances 0.000 claims 1
- 229940070721 polyacrylate Drugs 0.000 claims 1
- YPFDHNVEDLHUCE-UHFFFAOYSA-N propane-1,3-diol Chemical compound OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 claims 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 abstract 2
- 239000000243 solution Substances 0.000 description 27
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 19
- 239000000839 emulsion Substances 0.000 description 12
- 238000003756 stirring Methods 0.000 description 12
- KWYHDKDOAIKMQN-UHFFFAOYSA-N N,N,N',N'-tetramethylethylenediamine Chemical compound CN(C)CCN(C)C KWYHDKDOAIKMQN-UHFFFAOYSA-N 0.000 description 11
- 239000005662 Paraffin oil Substances 0.000 description 11
- 239000011049 pearl Substances 0.000 description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- ROOXNKNUYICQNP-UHFFFAOYSA-N ammonium persulfate Chemical compound [NH4+].[NH4+].[O-]S(=O)(=O)OOS([O-])(=O)=O ROOXNKNUYICQNP-UHFFFAOYSA-N 0.000 description 10
- CUNWUEBNSZSNRX-RKGWDQTMSA-N (2r,3r,4r,5s)-hexane-1,2,3,4,5,6-hexol;(z)-octadec-9-enoic acid Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO.OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO.CCCCCCCC\C=C/CCCCCCCC(O)=O.CCCCCCCC\C=C/CCCCCCCC(O)=O.CCCCCCCC\C=C/CCCCCCCC(O)=O CUNWUEBNSZSNRX-RKGWDQTMSA-N 0.000 description 9
- 229910052500 inorganic mineral Inorganic materials 0.000 description 9
- 239000011707 mineral Substances 0.000 description 9
- 239000007864 aqueous solution Substances 0.000 description 8
- 229960000583 acetic acid Drugs 0.000 description 7
- 239000003995 emulsifying agent Substances 0.000 description 7
- ZIUHHBKFKCYYJD-UHFFFAOYSA-N n,n'-methylenebisacrylamide Chemical compound C=CC(=O)NCNC(=O)C=C ZIUHHBKFKCYYJD-UHFFFAOYSA-N 0.000 description 7
- 239000000725 suspension Substances 0.000 description 7
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 6
- 229940117913 acrylamide Drugs 0.000 description 6
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- 229910001870 ammonium persulfate Inorganic materials 0.000 description 5
- 238000013019 agitation Methods 0.000 description 4
- 239000011324 bead Substances 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- 238000000926 separation method Methods 0.000 description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000007983 Tris buffer Substances 0.000 description 3
- NWGKJDSIEKMTRX-BFWOXRRGSA-N [(2r)-2-[(3r,4s)-3,4-dihydroxyoxolan-2-yl]-2-hydroxyethyl] (z)-octadec-9-enoate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OC[C@@H](O)C1OC[C@H](O)[C@H]1O NWGKJDSIEKMTRX-BFWOXRRGSA-N 0.000 description 3
- 239000002245 particle Substances 0.000 description 3
- JRKICGRDRMAZLK-UHFFFAOYSA-L peroxydisulfate Chemical compound [O-]S(=O)(=O)OOS([O-])(=O)=O JRKICGRDRMAZLK-UHFFFAOYSA-L 0.000 description 3
- 239000012071 phase Substances 0.000 description 3
- 239000012429 reaction media Substances 0.000 description 3
- 238000007873 sieving Methods 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
- BPQQTUXANYXVAA-UHFFFAOYSA-N Orthosilicate Chemical compound [O-][Si]([O-])([O-])[O-] BPQQTUXANYXVAA-UHFFFAOYSA-N 0.000 description 2
- 239000002202 Polyethylene glycol Substances 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 238000007792 addition Methods 0.000 description 2
- 239000007853 buffer solution Substances 0.000 description 2
- 238000004090 dissolution Methods 0.000 description 2
- 238000005194 fractionation Methods 0.000 description 2
- 238000002523 gelfiltration Methods 0.000 description 2
- 239000012362 glacial acetic acid Substances 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- 235000019198 oils Nutrition 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- 229920001223 polyethylene glycol Polymers 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- XHZPRMZZQOIPDS-UHFFFAOYSA-N 2-Methyl-2-[(1-oxo-2-propenyl)amino]-1-propanesulfonic acid Chemical compound OS(=O)(=O)CC(C)(C)NC(=O)C=C XHZPRMZZQOIPDS-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 1
- 235000003276 Apios tuberosa Nutrition 0.000 description 1
- 244000105624 Arachis hypogaea Species 0.000 description 1
- 235000010777 Arachis hypogaea Nutrition 0.000 description 1
- 235000010744 Arachis villosulicarpa Nutrition 0.000 description 1
- 108091003079 Bovine Serum Albumin Proteins 0.000 description 1
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
- 102000018832 Cytochromes Human genes 0.000 description 1
- 108010052832 Cytochromes Proteins 0.000 description 1
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 1
- 101100166829 Mus musculus Cenpk gene Proteins 0.000 description 1
- 102000036675 Myoglobin Human genes 0.000 description 1
- 108010062374 Myoglobin Proteins 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- 235000019486 Sunflower oil Nutrition 0.000 description 1
- 125000003647 acryloyl group Chemical group O=C([*])C([H])=C([H])[H] 0.000 description 1
- 150000001413 amino acids Chemical class 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 230000001580 bacterial effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000013043 chemical agent Substances 0.000 description 1
- 229910052804 chromium Inorganic materials 0.000 description 1
- 239000011651 chromium Substances 0.000 description 1
- 239000003431 cross linking reagent Substances 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000001804 emulsifying effect Effects 0.000 description 1
- 238000007720 emulsion polymerization reaction Methods 0.000 description 1
- 230000002255 enzymatic effect Effects 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 150000004676 glycans Chemical class 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 238000005342 ion exchange Methods 0.000 description 1
- 238000004255 ion exchange chromatography Methods 0.000 description 1
- 125000005395 methacrylic acid group Chemical group 0.000 description 1
- 102000039446 nucleic acids Human genes 0.000 description 1
- 108020004707 nucleic acids Proteins 0.000 description 1
- 239000002773 nucleotide Substances 0.000 description 1
- 125000003729 nucleotide group Chemical group 0.000 description 1
- QYSGYZVSCZSLHT-UHFFFAOYSA-N octafluoropropane Chemical compound FC(F)(F)C(F)(F)C(F)(F)F QYSGYZVSCZSLHT-UHFFFAOYSA-N 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 229920001282 polysaccharide Polymers 0.000 description 1
- 239000005017 polysaccharide Substances 0.000 description 1
- 229920000136 polysorbate Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 238000010526 radical polymerization reaction Methods 0.000 description 1
- 229920002545 silicone oil Polymers 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 235000012424 soybean oil Nutrition 0.000 description 1
- 239000003549 soybean oil Substances 0.000 description 1
- 235000000346 sugar Nutrition 0.000 description 1
- 150000008163 sugars Chemical class 0.000 description 1
- 239000002600 sunflower oil Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K3/00—Use of inorganic substances as compounding ingredients
- C08K3/34—Silicon-containing compounds
- C08K3/36—Silica
-
- 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
- B01J20/22—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
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F2/00—Processes of polymerisation
- C08F2/44—Polymerisation in the presence of compounding ingredients, e.g. plasticisers, dyestuffs, fillers
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S524/00—Synthetic resins or natural rubbers -- part of the class 520 series
- Y10S524/903—Aerosol compositions
Landscapes
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Analytical Chemistry (AREA)
- Graft Or Block Polymers (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Treatment Of Liquids With Adsorbents In General (AREA)
- Solid-Sorbent Or Filter-Aiding Compositions (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR878125 | 1987-06-11 | ||
| FR8708125A FR2616437B1 (fr) | 1987-06-11 | 1987-06-11 | Polymeres composites, leur preparation et leur utilisation en chromatographie liquide |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1302614C true CA1302614C (fr) | 1992-06-02 |
Family
ID=9351924
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000569262A Expired - Lifetime CA1302614C (fr) | 1987-06-11 | 1988-06-10 | Polymeres composites, leur preparation et leur utilisation en chromatographie liquide |
Country Status (9)
| Country | Link |
|---|---|
| US (2) | US5053135A (en, 2012) |
| EP (1) | EP0296926B1 (en, 2012) |
| JP (1) | JP2839144B2 (en, 2012) |
| AT (1) | ATE81521T1 (en, 2012) |
| CA (1) | CA1302614C (en, 2012) |
| DE (1) | DE3875287T2 (en, 2012) |
| ES (1) | ES2052756T3 (en, 2012) |
| FR (1) | FR2616437B1 (en, 2012) |
| GR (1) | GR3005982T3 (en, 2012) |
Families Citing this family (28)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE9013137U1 (de) * | 1990-09-15 | 1992-01-23 | Röhm GmbH, 6100 Darmstadt | Hochvernetztes, perlförmiges, aktivierbares, hydrophiles Trägermaterial |
| SE9101149D0 (sv) * | 1991-04-17 | 1991-04-17 | Pharmacia Lkb Biotech | Beads for down stream processing |
| DE4139747A1 (de) * | 1991-12-03 | 1993-06-09 | Bayer Ag, 5090 Leverkusen, De | Fuellstoffhaltige, optisch aktive perlpolymerisate |
| US5470463A (en) * | 1992-06-19 | 1995-11-28 | Sepracor Inc. | Passivated porous supports and methods for the preparation and use of same |
| US5445732A (en) * | 1992-06-19 | 1995-08-29 | Sepracor Inc. | Passivated porous polymer supports and methods for the preparation and use of same |
| WO1994000214A1 (en) * | 1992-06-19 | 1994-01-06 | Sepracor Inc. | Passivated and stabilized porous supports and methods for the preparation and use of 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 |
| US5906734A (en) * | 1992-06-19 | 1999-05-25 | Biosepra Inc. | Passivated porous polymer supports and methods for the preparation and use of same |
| US6706188B2 (en) | 1993-05-03 | 2004-03-16 | Amersham Biociences Ab | Process and means for down stream processing |
| US5486293A (en) * | 1994-03-21 | 1996-01-23 | Hemasure, Inc. | Removal of small exogenous molecules from biological fluids |
| US5906747A (en) * | 1995-11-13 | 1999-05-25 | Biosepra Inc. | Separation of molecules from dilute solutions using composite chromatography media having high dynamic sorptive capacity at high flow rates |
| DE19854575A1 (de) * | 1998-11-26 | 2000-05-31 | Basf Ag | Vernetzte quellfähige Polymere |
| KR100441283B1 (ko) * | 2001-09-11 | 2004-07-22 | 한국과학기술원 | 박리형 고분자/실리케이트 나노복합체의 제조방법 |
| FR2834227A1 (fr) * | 2001-12-27 | 2003-07-04 | Chiralsep Sarl | Materiaux supports optiquement actifs, leur procede de preparation et leurs utilisations |
| US20060292701A1 (en) * | 2002-09-13 | 2006-12-28 | Ciphergen Biosystems Inc. | Photocrosslinked hydrogel blend surface coatings |
| US7045366B2 (en) * | 2003-09-12 | 2006-05-16 | Ciphergen Biosystems, Inc. | Photocrosslinked hydrogel blend surface coatings |
| US7144743B2 (en) * | 2002-09-13 | 2006-12-05 | Pall Corporation | Preparation and use of mixed mode solid substrates for chromatography adsorbents and biochip arrays |
| US8021889B2 (en) * | 2004-01-20 | 2011-09-20 | Pall Corporation | Chromatographic material for the absorption of proteins at physiological ionic strength |
| US7125488B2 (en) * | 2004-02-12 | 2006-10-24 | Varian, Inc. | Polar-modified bonded phase materials for chromatographic separations |
| US20050272917A1 (en) * | 2004-05-14 | 2005-12-08 | Hematech, Llc | Methods for immunoglobulin purification |
| US7691263B1 (en) * | 2005-05-20 | 2010-04-06 | Brigham Young University | Monolithic column technology for liquid chromatography |
| US7628915B2 (en) | 2006-12-08 | 2009-12-08 | Varian, Inc. | Metal cyano bonded phases |
| EP2027875A1 (en) | 2007-08-23 | 2009-02-25 | Octapharma AG | A Process for Isolation and Purification of a Target Protein free of Prion Protein (PrPSC) |
| KR101808751B1 (ko) | 2009-11-13 | 2017-12-13 | 그리폴스 테라퓨틱스 인코포레이티드 | 폰 빌레브란트 인자(ｖＷＦ)-함유 제제, 및 그와 관련된 방법, 키트 및 용도 |
| US20110240541A1 (en) * | 2010-04-06 | 2011-10-06 | Binghe Gu | Monolithic column technology for liquid chromatography |
| JP5711510B2 (ja) * | 2010-12-08 | 2015-04-30 | 株式会社東芝 | 吸着材用アクリル系樹脂、水処理用カラム、および水処理方法 |
| US8802448B2 (en) | 2011-07-27 | 2014-08-12 | Pall Corporation | Mixed mode ligands |
| CN113149627A (zh) * | 2021-05-13 | 2021-07-23 | 武汉理工大学 | 一种熔融石英陶瓷及其制备方法 |
Family Cites Families (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2467341A (en) * | 1944-11-17 | 1949-04-12 | Monsanto Chemicals | Methacrylate compositions containing colloidal silica |
| US3557562A (en) * | 1968-01-31 | 1971-01-26 | Halliburton Co | Method of forming a flexible sealant |
| US3592834A (en) * | 1969-01-27 | 1971-07-13 | Buckman Labor Inc | Organo-silica polymers |
| JPS4888109A (en, 2012) * | 1972-02-25 | 1973-11-19 | ||
| SE7712058L (sv) * | 1976-11-12 | 1978-05-13 | Ceskoslovenska Akademie Ved | Tredimensionell berare av oorganiskt, porost material och en reaktiv polymer och ett forfarande for framstellning derav |
| US4281233A (en) * | 1977-05-03 | 1981-07-28 | Ceskoslovenska Akademie Ved | Hydrophilic macroporous three dimensional copolymers of hydroxyalkyl acrylates or methacrylates with crosslinking agents and the method of their manufacturing |
| EP0011190B1 (de) * | 1978-11-14 | 1983-02-16 | Bayer Ag | Füllstoffhaltige, vernetzte Perlpolymerisate |
| US4396476A (en) * | 1979-02-01 | 1983-08-02 | Dentsply Research & Development Corporation | Blend of cross-linked polymer, swelling monomer and cross-linking agent and curing process |
| US4368341A (en) * | 1980-09-15 | 1983-01-11 | Monsanto Company | Novel compounds and their use in elastomer-containing compositions |
| JPS58222101A (ja) * | 1982-06-18 | 1983-12-23 | Japan Synthetic Rubber Co Ltd | 充填剤を含有する重合体粒子 |
| JPS598711A (ja) * | 1982-07-06 | 1984-01-18 | Sumitomo Chem Co Ltd | ヒドロゲルの製造法 |
| US4442240A (en) * | 1983-07-14 | 1984-04-10 | Bisco, Inc. | Dental filling materials |
| HU190910B (en) * | 1983-08-16 | 1986-12-28 | Reanal Finomvegyszergyar,Hu | Method for producing glue suitable for fixing sorbent layer of pressurized one and multiple layer chromatography |
| US4724207A (en) * | 1984-02-02 | 1988-02-09 | Cuno Incorporated | Modified siliceous chromatographic supports |
| DE3706890A1 (de) * | 1987-03-04 | 1988-09-15 | Bayer Ag | Optisch aktive (meth)acrylamide, verfahren zu ihrer herstellung und ihre verwendung zur racematspaltung |
-
1987
- 1987-06-11 FR FR8708125A patent/FR2616437B1/fr not_active Expired - Fee Related
-
1988
- 1988-06-09 JP JP63140643A patent/JP2839144B2/ja not_active Expired - Lifetime
- 1988-06-10 DE DE8888401424T patent/DE3875287T2/de not_active Expired - Lifetime
- 1988-06-10 ES ES88401424T patent/ES2052756T3/es not_active Expired - Lifetime
- 1988-06-10 CA CA000569262A patent/CA1302614C/fr not_active Expired - Lifetime
- 1988-06-10 EP EP88401424A patent/EP0296926B1/fr not_active Expired - Lifetime
- 1988-06-10 AT AT88401424T patent/ATE81521T1/de not_active IP Right Cessation
-
1990
- 1990-05-11 US US07/521,988 patent/US5053135A/en not_active Expired - Lifetime
- 1990-11-29 US US07/619,822 patent/US5075371A/en not_active Expired - Lifetime
-
1992
- 1992-10-15 GR GR920400079T patent/GR3005982T3/el unknown
Also Published As
| Publication number | Publication date |
|---|---|
| US5053135A (en) | 1991-10-01 |
| DE3875287D1 (de) | 1992-11-19 |
| JPS6479247A (en) | 1989-03-24 |
| EP0296926B1 (fr) | 1992-10-14 |
| GR3005982T3 (en, 2012) | 1993-06-07 |
| FR2616437A1 (fr) | 1988-12-16 |
| EP0296926A1 (fr) | 1988-12-28 |
| DE3875287T2 (de) | 1993-04-15 |
| FR2616437B1 (fr) | 1990-09-07 |
| JP2839144B2 (ja) | 1998-12-16 |
| ATE81521T1 (de) | 1992-10-15 |
| US5075371A (en) | 1991-12-24 |
| ES2052756T3 (es) | 1994-07-16 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CA1302614C (fr) | Polymeres composites, leur preparation et leur utilisation en chromatographie liquide | |
| EP0040124B1 (fr) | Nouveaux copolymères hydrophiles à base de N- tris (hydroxyméthyl) méthyl acrylamide, procédés pour leur préparation, gels aqueux desdits copolymères et leur utilisation comme échangeurs d'ions | |
| CH631467A5 (fr) | Copolymeres statistiques reticules. | |
| EP0079842B1 (fr) | Nouveaux copolymères acryliques à base de N-acrylylpolyméthylèneimines ou de N-acrylyldialcoylamides, de N,N'-acrylyldiaminoalcanes et de N-acrylylaminoacides (ou esters), leur préparation et leur emploi comme échangeurs cationiques | |
| US4208309A (en) | Pearl polymer containing hollow pearls | |
| DE69027803T2 (de) | Polymerträger | |
| US5336742A (en) | Polymeric supports | |
| EP1268567B1 (fr) | Procede d'obtention d'un latex photochromique | |
| US5306561A (en) | Preparation of surface-functional polymer particles | |
| CA1202748A (en) | Hydrophilic polymer carrier for proteins | |
| HK1008029B (en) | Polymeric supports | |
| JPH11507402A (ja) | 分子的にインプリントされた粒状ポリマー及び同ポリマーのペルフロオロカーボン液中における安定化懸濁重合 | |
| US4190713A (en) | Pearl polymer containing hollow pearls | |
| FI72985C (fi) | Vinylenkarbonatpolymer, foerfarande foer dess framstaellning, och dess anvaendning. | |
| JPH0689055B2 (ja) | 担体に結合された生物学的に活性な物質 | |
| CA1291844C (fr) | Oligomeres a sequences polydieniques et a greffons photoreticulables et leurs applications notamment dans le revetement des metaux | |
| EP0133392A1 (fr) | Procédé de préparation de copolymères en grains, fonctionnalisés, par polymérisation en suspension dans un milieu non aqueux | |
| FR2682609A1 (fr) | Support pour la preparation de colonnes chromatographiques et procede pour sa preparation. | |
| JPS61162750A (ja) | 光学分割用充填剤 | |
| EP0564570A1 (fr) | Polymeres cyclodextrine-epichlorhydrine utilisables pour la separation et l'adsorption de substances | |
| Milbrath et al. | Heilman et al.[45] Date of Patent: Mar. 8, 1994 | |
| JPS61160054A (ja) | 光学分割用充填剤 | |
| KR920704135A (ko) | 카치온 교환액체 크로마토그라피용 담체의 제조방법 및 그 담체를 사용한 당화 헤모글로빈의 정량방법 |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |