EP1458475A2 - Optically active support materials, method for preparing same and uses thereof - Google Patents
Optically active support materials, method for preparing same and uses thereofInfo
- 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
Links
- 239000000463 material Substances 0.000 title claims abstract description 41
- 238000000034 method Methods 0.000 title claims abstract description 16
- AKZWRTCWNXHHFR-PDIZUQLASA-N [(3S)-oxolan-3-yl] N-[(2S,3S)-4-[(5S)-5-benzyl-3-[(2R)-2-carbamoyloxy-2,3-dihydro-1H-inden-1-yl]-4-oxo-3H-pyrrol-5-yl]-3-hydroxy-1-phenylbutan-2-yl]carbamate Chemical compound NC(=O)O[C@@H]1Cc2ccccc2C1C1C=N[C@](C[C@H](O)[C@H](Cc2ccccc2)NC(=O)O[C@H]2CCOC2)(Cc2ccccc2)C1=O AKZWRTCWNXHHFR-PDIZUQLASA-N 0.000 claims abstract description 72
- 150000002148 esters Chemical class 0.000 claims abstract description 57
- 229920001282 polysaccharide Polymers 0.000 claims abstract description 48
- 239000005017 polysaccharide Substances 0.000 claims abstract description 48
- 150000004676 glycans Chemical class 0.000 claims abstract description 47
- 239000007787 solid Substances 0.000 claims abstract description 46
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims abstract description 38
- 229910052500 inorganic mineral Inorganic materials 0.000 claims abstract description 35
- 239000011707 mineral Substances 0.000 claims abstract description 35
- 229920001542 oligosaccharide Polymers 0.000 claims abstract description 34
- -1 oligosaccharide ester Chemical class 0.000 claims abstract description 34
- MCMNRKCIXSYSNV-UHFFFAOYSA-N Zirconium dioxide Chemical compound O=[Zr]=O MCMNRKCIXSYSNV-UHFFFAOYSA-N 0.000 claims abstract description 20
- 239000000377 silicon dioxide Substances 0.000 claims abstract description 12
- 150000002482 oligosaccharides Chemical class 0.000 claims description 32
- 235000010755 mineral Nutrition 0.000 claims description 31
- 239000004793 Polystyrene Substances 0.000 claims description 22
- 150000004657 carbamic acid derivatives Chemical class 0.000 claims description 20
- 239000000725 suspension Substances 0.000 claims description 20
- MYRTYDVEIRVNKP-UHFFFAOYSA-N divinylbenzene Substances C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 claims description 18
- 229920002223 polystyrene Polymers 0.000 claims description 16
- 229920002678 cellulose Polymers 0.000 claims description 15
- 229920002554 vinyl polymer Polymers 0.000 claims description 15
- 239000004952 Polyamide Substances 0.000 claims description 14
- 239000001913 cellulose Substances 0.000 claims description 14
- 239000000203 mixture Substances 0.000 claims description 14
- 229920002647 polyamide Polymers 0.000 claims description 14
- 239000010457 zeolite Substances 0.000 claims description 14
- 229920000856 Amylose Polymers 0.000 claims description 12
- 239000000126 substance Substances 0.000 claims description 12
- 229910002027 silica gel Inorganic materials 0.000 claims description 10
- 239000000741 silica gel Substances 0.000 claims description 10
- 229920000936 Agarose Polymers 0.000 claims description 9
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 9
- HCWCAKKEBCNQJP-UHFFFAOYSA-N magnesium orthosilicate Chemical compound [Mg+2].[Mg+2].[O-][Si]([O-])([O-])[O-] HCWCAKKEBCNQJP-UHFFFAOYSA-N 0.000 claims description 9
- 239000000391 magnesium silicate Substances 0.000 claims description 9
- 229910052919 magnesium silicate Inorganic materials 0.000 claims description 9
- 235000019792 magnesium silicate Nutrition 0.000 claims description 9
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims description 8
- 229920002292 Nylon 6 Polymers 0.000 claims description 8
- WGLPBDUCMAPZCE-UHFFFAOYSA-N Trioxochromium Chemical compound O=[Cr](=O)=O WGLPBDUCMAPZCE-UHFFFAOYSA-N 0.000 claims description 8
- 229910052810 boron oxide Inorganic materials 0.000 claims description 8
- 229910000423 chromium oxide Inorganic materials 0.000 claims description 8
- 239000000470 constituent Substances 0.000 claims description 8
- JKWMSGQKBLHBQQ-UHFFFAOYSA-N diboron trioxide Chemical compound O=BOB=O JKWMSGQKBLHBQQ-UHFFFAOYSA-N 0.000 claims description 8
- 229920002451 polyvinyl alcohol Polymers 0.000 claims description 8
- 229920002307 Dextran Polymers 0.000 claims description 7
- 230000001588 bifunctional effect Effects 0.000 claims description 7
- 229910052799 carbon Inorganic materials 0.000 claims description 7
- 239000003795 chemical substances by application Substances 0.000 claims description 7
- 239000002131 composite material Substances 0.000 claims description 7
- 229920001577 copolymer Chemical compound 0.000 claims description 7
- 238000001035 drying Methods 0.000 claims description 7
- 239000002904 solvent Substances 0.000 claims description 7
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 6
- 229920001661 Chitosan Polymers 0.000 claims description 6
- 229920000858 Cyclodextrin Polymers 0.000 claims description 6
- CPLXHLVBOLITMK-UHFFFAOYSA-N Magnesium oxide Chemical compound [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 claims description 6
- YKTSYUJCYHOUJP-UHFFFAOYSA-N [O--].[Al+3].[Al+3].[O-][Si]([O-])([O-])[O-] Chemical compound [O--].[Al+3].[Al+3].[O-][Si]([O-])([O-])[O-] YKTSYUJCYHOUJP-UHFFFAOYSA-N 0.000 claims description 6
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 claims description 6
- 238000004587 chromatography analysis Methods 0.000 claims description 6
- 239000004927 clay Substances 0.000 claims description 6
- 238000006116 polymerization reaction Methods 0.000 claims description 6
- 235000019422 polyvinyl alcohol Nutrition 0.000 claims description 6
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 claims description 5
- 238000010438 heat treatment Methods 0.000 claims description 5
- 235000012245 magnesium oxide Nutrition 0.000 claims description 5
- 229920000131 polyvinylidene Polymers 0.000 claims description 5
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 claims description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 4
- 239000004698 Polyethylene Substances 0.000 claims description 4
- 229920002873 Polyethylenimine Polymers 0.000 claims description 4
- 239000004372 Polyvinyl alcohol Substances 0.000 claims description 4
- 229920002125 Sokalan® Polymers 0.000 claims description 4
- 229920002472 Starch Polymers 0.000 claims description 4
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 claims description 4
- QCWXUUIWCKQGHC-UHFFFAOYSA-N Zirconium Chemical compound [Zr] QCWXUUIWCKQGHC-UHFFFAOYSA-N 0.000 claims description 4
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
- STVZJERGLQHEKB-UHFFFAOYSA-N ethylene glycol dimethacrylate Substances CC(=C)C(=O)OCCOC(=O)C(C)=C STVZJERGLQHEKB-UHFFFAOYSA-N 0.000 claims description 4
- 229910052588 hydroxylapatite Inorganic materials 0.000 claims description 4
- 239000000395 magnesium oxide Substances 0.000 claims description 4
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 claims description 4
- 239000002245 particle Substances 0.000 claims description 4
- XYJRXVWERLGGKC-UHFFFAOYSA-D pentacalcium;hydroxide;triphosphate Chemical compound [OH-].[Ca+2].[Ca+2].[Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O XYJRXVWERLGGKC-UHFFFAOYSA-D 0.000 claims description 4
- 229920002401 polyacrylamide Polymers 0.000 claims description 4
- 229920000573 polyethylene Polymers 0.000 claims description 4
- 239000011148 porous material Substances 0.000 claims description 4
- 239000003586 protic polar solvent Substances 0.000 claims description 4
- 229910052814 silicon oxide Inorganic materials 0.000 claims description 4
- 235000019698 starch Nutrition 0.000 claims description 4
- 239000008107 starch Substances 0.000 claims description 4
- 229910052718 tin Inorganic materials 0.000 claims description 4
- 239000010936 titanium Substances 0.000 claims description 4
- 229910052719 titanium Inorganic materials 0.000 claims description 4
- 229910052726 zirconium Inorganic materials 0.000 claims description 4
- 239000002253 acid Substances 0.000 claims description 3
- 239000000010 aprotic solvent Substances 0.000 claims description 3
- 239000000460 chlorine Substances 0.000 claims description 3
- 238000004132 cross linking Methods 0.000 claims description 3
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 claims description 3
- XJRBAMWJDBPFIM-UHFFFAOYSA-N methyl vinyl ether Chemical compound COC=C XJRBAMWJDBPFIM-UHFFFAOYSA-N 0.000 claims description 3
- 229920000620 organic polymer Polymers 0.000 claims description 3
- ROLAGNYPWIVYTG-UHFFFAOYSA-N 1,2-bis(4-methoxyphenyl)ethanamine;hydrochloride Chemical compound Cl.C1=CC(OC)=CC=C1CC(N)C1=CC=C(OC)C=C1 ROLAGNYPWIVYTG-UHFFFAOYSA-N 0.000 claims description 2
- UWFRVQVNYNPBEF-UHFFFAOYSA-N 1-(2,4-dimethylphenyl)propan-1-one Chemical compound CCC(=O)C1=CC=C(C)C=C1C UWFRVQVNYNPBEF-UHFFFAOYSA-N 0.000 claims description 2
- WGGLDBIZIQMEGH-UHFFFAOYSA-N 1-bromo-4-ethenylbenzene Chemical compound BrC1=CC=C(C=C)C=C1 WGGLDBIZIQMEGH-UHFFFAOYSA-N 0.000 claims description 2
- KUIZKZHDMPERHR-UHFFFAOYSA-N 1-phenylprop-2-en-1-one Chemical compound C=CC(=O)C1=CC=CC=C1 KUIZKZHDMPERHR-UHFFFAOYSA-N 0.000 claims description 2
- QWVCIORZLNBIIC-UHFFFAOYSA-N 2,3-dibromopropan-1-ol Chemical compound OCC(Br)CBr QWVCIORZLNBIIC-UHFFFAOYSA-N 0.000 claims description 2
- OEPOKWHJYJXUGD-UHFFFAOYSA-N 2-(3-phenylmethoxyphenyl)-1,3-thiazole-4-carbaldehyde Chemical compound O=CC1=CSC(C=2C=C(OCC=3C=CC=CC=3)C=CC=2)=N1 OEPOKWHJYJXUGD-UHFFFAOYSA-N 0.000 claims description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 2
- 125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 claims description 2
- 125000005999 2-bromoethyl group Chemical group 0.000 claims description 2
- WSQZNZLOZXSBHA-UHFFFAOYSA-N 3,8-dioxabicyclo[8.2.2]tetradeca-1(12),10,13-triene-2,9-dione Chemical compound O=C1OCCCCOC(=O)C2=CC=C1C=C2 WSQZNZLOZXSBHA-UHFFFAOYSA-N 0.000 claims description 2
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 2
- 229920001450 Alpha-Cyclodextrin Polymers 0.000 claims description 2
- 239000005995 Aluminium silicate Substances 0.000 claims description 2
- DJHGAFSJWGLOIV-UHFFFAOYSA-K Arsenate3- Chemical class [O-][As]([O-])([O-])=O DJHGAFSJWGLOIV-UHFFFAOYSA-K 0.000 claims description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 claims description 2
- 229920002284 Cellulose triacetate Polymers 0.000 claims description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 2
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 claims description 2
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 2
- 239000005977 Ethylene Substances 0.000 claims description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 2
- 229910019142 PO4 Inorganic materials 0.000 claims description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 2
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims description 2
- 229920003171 Poly (ethylene oxide) Polymers 0.000 claims description 2
- 229920000754 Poly(1,4-phenylene ether-ether-sulfone) Polymers 0.000 claims description 2
- 229920000488 Poly(1,4-phenylene sulfide) Polymers 0.000 claims description 2
- 229920001054 Poly(ethylene‐co‐vinyl acetate) Polymers 0.000 claims description 2
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 2
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 claims description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 2
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 claims description 2
- NNLVGZFZQQXQNW-ADJNRHBOSA-N [(2r,3r,4s,5r,6s)-4,5-diacetyloxy-3-[(2s,3r,4s,5r,6r)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxy-6-[(2r,3r,4s,5r,6s)-4,5,6-triacetyloxy-2-(acetyloxymethyl)oxan-3-yl]oxyoxan-2-yl]methyl acetate Chemical compound O([C@@H]1O[C@@H]([C@H]([C@H](OC(C)=O)[C@H]1OC(C)=O)O[C@H]1[C@@H]([C@@H](OC(C)=O)[C@H](OC(C)=O)[C@@H](COC(C)=O)O1)OC(C)=O)COC(=O)C)[C@@H]1[C@@H](COC(C)=O)O[C@@H](OC(C)=O)[C@H](OC(C)=O)[C@H]1OC(C)=O NNLVGZFZQQXQNW-ADJNRHBOSA-N 0.000 claims description 2
- 125000002877 alkyl aryl group Chemical group 0.000 claims description 2
- 235000012211 aluminium silicate Nutrition 0.000 claims description 2
- 125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 claims description 2
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 2
- 125000003118 aryl group Chemical group 0.000 claims description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 2
- 229910052794 bromium Inorganic materials 0.000 claims description 2
- NTXGQCSETZTARF-UHFFFAOYSA-N buta-1,3-diene;prop-2-enenitrile Polymers C=CC=C.C=CC#N NTXGQCSETZTARF-UHFFFAOYSA-N 0.000 claims description 2
- 239000011575 calcium Substances 0.000 claims description 2
- 229910052791 calcium Inorganic materials 0.000 claims description 2
- 239000004202 carbamide Substances 0.000 claims description 2
- 150000001720 carbohydrates Chemical group 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 229920002301 cellulose acetate Polymers 0.000 claims description 2
- 239000000919 ceramic Substances 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- 229910052570 clay Inorganic materials 0.000 claims description 2
- 229940097362 cyclodextrins Drugs 0.000 claims description 2
- NLDGJRWPPOSWLC-UHFFFAOYSA-N deca-1,9-diene Chemical compound C=CCCCCCCC=C NLDGJRWPPOSWLC-UHFFFAOYSA-N 0.000 claims description 2
- AFOSIXZFDONLBT-UHFFFAOYSA-N divinyl sulfone Chemical compound C=CS(=O)(=O)C=C AFOSIXZFDONLBT-UHFFFAOYSA-N 0.000 claims description 2
- WGXGKXTZIQFQFO-CMDGGOBGSA-N ethenyl (e)-3-phenylprop-2-enoate Chemical compound C=COC(=O)\C=C\C1=CC=CC=C1 WGXGKXTZIQFQFO-CMDGGOBGSA-N 0.000 claims description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 2
- 229920005648 ethylene methacrylic acid copolymer Polymers 0.000 claims description 2
- 239000011737 fluorine Substances 0.000 claims description 2
- 229910052731 fluorine Inorganic materials 0.000 claims description 2
- 239000011521 glass Substances 0.000 claims description 2
- PBZROIMXDZTJDF-UHFFFAOYSA-N hepta-1,6-dien-4-one Chemical compound C=CCC(=O)CC=C PBZROIMXDZTJDF-UHFFFAOYSA-N 0.000 claims description 2
- 125000005842 heteroatom Chemical group 0.000 claims description 2
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims description 2
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 2
- 239000011630 iodine Substances 0.000 claims description 2
- 229910052740 iodine Inorganic materials 0.000 claims description 2
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 claims description 2
- 150000002576 ketones Chemical class 0.000 claims description 2
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 claims description 2
- 239000011976 maleic acid Substances 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 229910052757 nitrogen Inorganic materials 0.000 claims description 2
- JFNLZVQOOSMTJK-KNVOCYPGSA-N norbornene Chemical compound C1[C@@H]2CC[C@H]1C=C2 JFNLZVQOOSMTJK-KNVOCYPGSA-N 0.000 claims description 2
- LJAGLQVRUZWQGK-UHFFFAOYSA-N oxecane-2,10-dione Chemical compound O=C1CCCCCCCC(=O)O1 LJAGLQVRUZWQGK-UHFFFAOYSA-N 0.000 claims description 2
- 239000001301 oxygen Substances 0.000 claims description 2
- 229910052760 oxygen Inorganic materials 0.000 claims description 2
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- 235000021317 phosphate Nutrition 0.000 claims description 2
- 150000003013 phosphoric acid derivatives Chemical class 0.000 claims description 2
- 229910052698 phosphorus Inorganic materials 0.000 claims description 2
- 239000011574 phosphorus Substances 0.000 claims description 2
- 229920000314 poly p-methyl styrene Polymers 0.000 claims description 2
- 229920000705 poly(2-acrylamido-2-methyl-1-propanesulfonic acid-co-acrylonitrile) Polymers 0.000 claims description 2
- 229920000559 poly(Bisphenol A-co-epichlorohydrin) Polymers 0.000 claims description 2
- 229920003227 poly(N-vinyl carbazole) Polymers 0.000 claims description 2
- 229920000712 poly(acrylamide-co-diallyldimethylammonium chloride) Polymers 0.000 claims description 2
- 229920001446 poly(acrylic acid-co-maleic acid) Polymers 0.000 claims description 2
- 229920000083 poly(allylamine) Polymers 0.000 claims description 2
- 229920005593 poly(benzyl methacrylate) Polymers 0.000 claims description 2
- 229920001490 poly(butyl methacrylate) polymer Polymers 0.000 claims description 2
- 229920001200 poly(ethylene-vinyl acetate) Polymers 0.000 claims description 2
- 229920000352 poly(styrene-co-divinylbenzene) Polymers 0.000 claims description 2
- 229920002492 poly(sulfone) Polymers 0.000 claims description 2
- 229920003251 poly(α-methylstyrene) Polymers 0.000 claims description 2
- 229920001798 poly[2-(acrylamido)-2-methyl-1-propanesulfonic acid] polymer Polymers 0.000 claims description 2
- 229920000058 polyacrylate Polymers 0.000 claims description 2
- 229920002239 polyacrylonitrile Polymers 0.000 claims description 2
- 229920000767 polyaniline Polymers 0.000 claims description 2
- 229920001610 polycaprolactone Polymers 0.000 claims description 2
- 239000004632 polycaprolactone Substances 0.000 claims description 2
- 229920000682 polycarbomethylsilane Polymers 0.000 claims description 2
- 229920000728 polyester Polymers 0.000 claims description 2
- 229920000139 polyethylene terephthalate Polymers 0.000 claims description 2
- 239000005020 polyethylene terephthalate Substances 0.000 claims description 2
- 229920002338 polyhydroxyethylmethacrylate Polymers 0.000 claims description 2
- 229920001228 polyisocyanate Polymers 0.000 claims description 2
- 239000005056 polyisocyanate Substances 0.000 claims description 2
- 229920000098 polyolefin Polymers 0.000 claims description 2
- 229920000379 polypropylene carbonate Polymers 0.000 claims description 2
- 229920001343 polytetrafluoroethylene Polymers 0.000 claims description 2
- 239000004810 polytetrafluoroethylene Substances 0.000 claims description 2
- 229920000909 polytetrahydrofuran Polymers 0.000 claims description 2
- 229920002635 polyurethane Polymers 0.000 claims description 2
- 239000004814 polyurethane Substances 0.000 claims description 2
- 229920002689 polyvinyl acetate Polymers 0.000 claims description 2
- 239000011118 polyvinyl acetate Substances 0.000 claims description 2
- 229920001289 polyvinyl ether Polymers 0.000 claims description 2
- 229920002981 polyvinylidene fluoride Polymers 0.000 claims description 2
- 229920000036 polyvinylpyrrolidone Polymers 0.000 claims description 2
- 239000001267 polyvinylpyrrolidone Substances 0.000 claims description 2
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 claims description 2
- 229920005989 resin Polymers 0.000 claims description 2
- 239000011347 resin Substances 0.000 claims description 2
- 150000004760 silicates Chemical class 0.000 claims description 2
- 239000010703 silicon Substances 0.000 claims description 2
- 229910052710 silicon Inorganic materials 0.000 claims description 2
- 150000003440 styrenes Chemical class 0.000 claims description 2
- 239000011593 sulfur Substances 0.000 claims description 2
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- KKEYFWRCBNTPAC-UHFFFAOYSA-L terephthalate(2-) Chemical compound [O-]C(=O)C1=CC=C(C([O-])=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-L 0.000 claims description 2
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Abstract
Description
Claims
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
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FR0116933A FR2834227A1 (en) | 2001-12-27 | 2001-12-27 | OPTICALLY ACTIVE SUPPORTING MATERIALS, PROCESS FOR PREPARING THEM AND USES THEREOF |
FR0116933 | 2001-12-27 | ||
PCT/FR2002/004391 WO2003055594A2 (en) | 2001-12-27 | 2002-12-17 | Optically active support materials, method for preparing same and uses thereof |
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EP1458475A2 true EP1458475A2 (en) | 2004-09-22 |
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EP02805798A Ceased EP1458475A2 (en) | 2001-12-27 | 2002-12-17 | Optically active support materials, method for preparing same and uses thereof |
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EP (1) | EP1458475A2 (en) |
JP (1) | JP2005513492A (en) |
KR (1) | KR20040078656A (en) |
CN (1) | CN1617762A (en) |
AU (1) | AU2002364659B2 (en) |
FR (1) | FR2834227A1 (en) |
NO (1) | NO20043125L (en) |
WO (1) | WO2003055594A2 (en) |
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CN102741258B (en) * | 2009-06-17 | 2015-09-30 | 德州大学体系董事会 | As constituent and the method for the cyclofructan of separating agent |
WO2011088225A1 (en) | 2010-01-15 | 2011-07-21 | 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 |
CA2825651C (en) | 2011-02-02 | 2020-03-24 | Bio-Rad Laboratories, Inc. | Apatite surface neutralization with alkali solutions |
CN102205770B (en) * | 2011-03-16 | 2013-09-25 | 北京培宏望志科技有限公司 | Method for using image in tabulate photo to make three-dimensional entity |
WO2013180933A1 (en) * | 2012-05-30 | 2013-12-05 | Bio-Rad Laboratories, Inc. | In situ restoration of apatite-based chromatography resins |
US9302203B2 (en) * | 2012-07-20 | 2016-04-05 | Mitsubishi Chemical Corporation | Chromatographic separation material |
CN109054254B (en) | 2012-08-17 | 2021-02-02 | Cj第一制糖株式会社 | Bio-based rubber modifiers for polymer blends |
CN103105442B (en) * | 2013-01-18 | 2014-06-18 | 华侨大学 | Method for detecting high-molecule block polymer structure parameters by gel permeation chromatography |
CN103111271B (en) * | 2013-03-04 | 2014-10-15 | 福州大学 | Preparation method of chitosan-grafted beta-cyclodextrin bonded silica gel absorbent |
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WO2015200299A2 (en) | 2014-06-23 | 2015-12-30 | Bio-Rad Laboratories, Inc. | Apatite in-situ restoration |
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JP6810039B2 (en) * | 2015-07-31 | 2021-01-06 | 株式会社ダイセル | Stationary phase for supercritical fluid chromatography |
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CN106582580A (en) * | 2016-12-22 | 2017-04-26 | 苏州楚博生物技术有限公司 | High-pressure-resistant affinity chromatography media for chromatographic column |
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CN107252638A (en) * | 2017-07-13 | 2017-10-17 | 杭州水处理技术研究开发中心有限公司 | A kind of preparation method of the high-flux nanofiltration membrane containing modified cuttlebone nano-particle |
CN110548494B (en) * | 2019-10-11 | 2020-10-09 | 湖北工业大学 | Method for preparing magnetic adsorption material by using animal and plant wastes |
CN111662791A (en) * | 2020-06-08 | 2020-09-15 | 江苏欣捷衬布有限公司 | Low-temperature cleaning soaping agent for reactive dye dyed lining cloth and preparation method thereof |
CN112121776B (en) * | 2020-09-18 | 2021-06-15 | 董晓明 | Adsorbent for removing antimony in printing and dyeing wastewater and preparation method and application thereof |
CN112778437B (en) * | 2020-12-31 | 2022-07-15 | 北京科华微电子材料有限公司 | Natural polysaccharide modified resin, preparation method and application thereof, and photoresist |
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JPH07260762A (en) * | 1994-03-17 | 1995-10-13 | Daicel Chem Ind Ltd | Filler for high-speed liquid chromatography and manufacture thereof |
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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 |
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FR2784108A1 (en) | 1998-09-11 | 2000-04-07 | Inst Francais Du Petrole | NEW CROSS-LINKED POLYMERS BASED ON BIS-SILANE DERIVATIVES, BIS-THIOETHERS, BIS-SULFOXIDES, BIS-SULPHONES AND BUTANE DI-YL FROM POLYSACCHARIDES AND OLIGOSACCHARIDES, AND THEIR FORMATION INTO SUPPORTED MATERIALS |
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WO2003049833A1 (en) * | 2001-11-27 | 2003-06-19 | Ciphergen Biosystems, Inc. | Composite chromatographic sorbent of mineral oxide beads with hydroxyapatite-filled pores |
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AU2002364659B2 (en) | 2008-02-28 |
JP2005513492A (en) | 2005-05-12 |
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