JP4750280B2 - クロマトグラフィ分離のための多孔質の無機／有機ハイブリッド粒子、及び、その調製プロセス - Google Patents
クロマトグラフィ分離のための多孔質の無機／有機ハイブリッド粒子、及び、その調製プロセス Download PDFInfo
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- JP4750280B2 JP4750280B2 JP2000597060A JP2000597060A JP4750280B2 JP 4750280 B2 JP4750280 B2 JP 4750280B2 JP 2000597060 A JP2000597060 A JP 2000597060A JP 2000597060 A JP2000597060 A JP 2000597060A JP 4750280 B2 JP4750280 B2 JP 4750280B2
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- 238000000034 method Methods 0.000 title claims abstract description 102
- 239000002245 particle Substances 0.000 title claims abstract description 92
- 238000013375 chromatographic separation Methods 0.000 title abstract description 4
- 238000002360 preparation method Methods 0.000 title abstract description 4
- 239000011148 porous material Substances 0.000 claims abstract description 79
- 239000000463 material Substances 0.000 claims abstract description 76
- 238000000926 separation method Methods 0.000 claims abstract description 10
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 107
- 125000000217 alkyl group Chemical group 0.000 claims description 64
- 239000000377 silicon dioxide Substances 0.000 claims description 45
- 125000003118 aryl group Chemical group 0.000 claims description 43
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Natural products CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 42
- 125000000524 functional group Chemical group 0.000 claims description 35
- 125000003277 amino group Chemical group 0.000 claims description 28
- 238000004587 chromatography analysis Methods 0.000 claims description 27
- 239000002585 base Substances 0.000 claims description 22
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 22
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 22
- -1 alkaline earth metal cation Chemical class 0.000 claims description 21
- 239000000203 mixture Substances 0.000 claims description 21
- 150000002009 diols Chemical group 0.000 claims description 19
- 239000004094 surface-active agent Substances 0.000 claims description 19
- 239000003054 catalyst Substances 0.000 claims description 18
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 16
- 239000000725 suspension Substances 0.000 claims description 16
- GZGREZWGCWVAEE-UHFFFAOYSA-N chloro-dimethyl-octadecylsilane Chemical compound CCCCCCCCCCCCCCCCCC[Si](C)(C)Cl GZGREZWGCWVAEE-UHFFFAOYSA-N 0.000 claims description 15
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical group [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 claims description 13
- 125000004450 alkenylene group Chemical group 0.000 claims description 13
- 125000002947 alkylene group Chemical group 0.000 claims description 13
- 125000004419 alkynylene group Chemical group 0.000 claims description 13
- 125000000732 arylene group Chemical group 0.000 claims description 13
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 13
- 239000003607 modifier Substances 0.000 claims description 13
- 125000005372 silanol group Chemical group 0.000 claims description 13
- BOTDANWDWHJENH-UHFFFAOYSA-N Tetraethyl orthosilicate Chemical compound CCO[Si](OCC)(OCC)OCC BOTDANWDWHJENH-UHFFFAOYSA-N 0.000 claims description 12
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 11
- 230000005526 G1 to G0 transition Effects 0.000 claims description 10
- 125000001931 aliphatic group Chemical group 0.000 claims description 10
- 238000000576 coating method Methods 0.000 claims description 10
- 238000012986 modification Methods 0.000 claims description 10
- 230000004048 modification Effects 0.000 claims description 10
- 229920000642 polymer Polymers 0.000 claims description 10
- 239000003377 acid catalyst Substances 0.000 claims description 9
- 239000011248 coating agent Substances 0.000 claims description 9
- 238000010335 hydrothermal treatment Methods 0.000 claims description 9
- 238000012856 packing Methods 0.000 claims description 9
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 9
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 8
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 8
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical group [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 claims description 7
- 150000001768 cations Chemical class 0.000 claims description 7
- DBKNGKYVNBJWHL-UHFFFAOYSA-N chloro-dimethyl-octylsilane Chemical compound CCCCCCCC[Si](C)(C)Cl DBKNGKYVNBJWHL-UHFFFAOYSA-N 0.000 claims description 7
- 125000004122 cyclic group Chemical group 0.000 claims description 7
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 7
- 238000006116 polymerization reaction Methods 0.000 claims description 7
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 7
- 239000000908 ammonium hydroxide Substances 0.000 claims description 6
- 238000005349 anion exchange Methods 0.000 claims description 6
- 229910052794 bromium Inorganic materials 0.000 claims description 6
- 238000005341 cation exchange Methods 0.000 claims description 6
- 229910052801 chlorine Inorganic materials 0.000 claims description 6
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 6
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 6
- 230000007062 hydrolysis Effects 0.000 claims description 6
- 238000006460 hydrolysis reaction Methods 0.000 claims description 6
- 229910052740 iodine Inorganic materials 0.000 claims description 6
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 claims description 6
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 claims description 6
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 6
- 229910052799 carbon Inorganic materials 0.000 claims description 4
- 238000001914 filtration Methods 0.000 claims description 4
- 230000003301 hydrolyzing effect Effects 0.000 claims description 4
- 239000012528 membrane Substances 0.000 claims description 4
- 125000000962 organic group Chemical group 0.000 claims description 4
- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 claims description 4
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 claims description 3
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 claims description 3
- 229910010293 ceramic material Inorganic materials 0.000 claims description 3
- RVTZCBVAJQQJTK-UHFFFAOYSA-N oxygen(2-);zirconium(4+) Chemical compound [O-2].[O-2].[Zr+4] RVTZCBVAJQQJTK-UHFFFAOYSA-N 0.000 claims description 3
- 238000000746 purification Methods 0.000 claims description 3
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 claims description 3
- 229910001928 zirconium oxide Inorganic materials 0.000 claims description 3
- 125000002827 triflate group Chemical group FC(S(=O)(=O)O*)(F)F 0.000 claims description 2
- 229910004298 SiO 2 Inorganic materials 0.000 claims 16
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims 6
- 239000007900 aqueous suspension Substances 0.000 claims 6
- LFQCEHFDDXELDD-UHFFFAOYSA-N tetramethyl orthosilicate Chemical compound CO[Si](OC)(OC)OC LFQCEHFDDXELDD-UHFFFAOYSA-N 0.000 claims 5
- 125000003837 (C1-C20) alkyl group Chemical group 0.000 claims 3
- 239000003513 alkali Substances 0.000 claims 3
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 claims 3
- 238000007306 functionalization reaction Methods 0.000 claims 3
- 125000003944 tolyl group Chemical group 0.000 claims 3
- 239000003795 chemical substances by application Substances 0.000 claims 2
- 239000012504 chromatography matrix Substances 0.000 claims 2
- 238000009833 condensation Methods 0.000 claims 2
- 230000005494 condensation Effects 0.000 claims 2
- 150000002500 ions Chemical group 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 32
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 21
- 239000000243 solution Substances 0.000 description 16
- 125000004432 carbon atom Chemical group C* 0.000 description 15
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 15
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 14
- 239000000047 product Substances 0.000 description 14
- 238000001879 gelation Methods 0.000 description 12
- 125000004079 stearyl group Chemical group [H]C([*])([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])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 12
- 239000011324 bead Substances 0.000 description 11
- 125000003545 alkoxy group Chemical group 0.000 description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 9
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
- 125000002723 alicyclic group Chemical group 0.000 description 8
- 239000002002 slurry Substances 0.000 description 8
- 125000003342 alkenyl group Chemical group 0.000 description 7
- 125000004414 alkyl thio group Chemical group 0.000 description 7
- 125000000753 cycloalkyl group Chemical group 0.000 description 7
- 125000000623 heterocyclic group Chemical group 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- KXDHJXZQYSOELW-UHFFFAOYSA-N Carbamic acid Chemical group NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 description 6
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical group C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 6
- 125000003282 alkyl amino group Chemical group 0.000 description 6
- 239000008346 aqueous phase Substances 0.000 description 6
- IJOOHPMOJXWVHK-UHFFFAOYSA-N chlorotrimethylsilane Chemical compound C[Si](C)(C)Cl IJOOHPMOJXWVHK-UHFFFAOYSA-N 0.000 description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 6
- 239000000741 silica gel Substances 0.000 description 6
- 229910002027 silica gel Inorganic materials 0.000 description 6
- 238000001179 sorption measurement Methods 0.000 description 6
- KAESVJOAVNADME-UHFFFAOYSA-N 1H-pyrrole Natural products C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 5
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 5
- 125000005157 alkyl carboxy group Chemical group 0.000 description 5
- 125000004429 atom Chemical group 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- 125000004966 cyanoalkyl group Chemical group 0.000 description 5
- 238000001212 derivatisation Methods 0.000 description 5
- 239000000839 emulsion Substances 0.000 description 5
- 229910052736 halogen Inorganic materials 0.000 description 5
- 150000002367 halogens Chemical class 0.000 description 5
- 239000001257 hydrogen Substances 0.000 description 5
- 229910052739 hydrogen Inorganic materials 0.000 description 5
- 125000001424 substituent group Chemical group 0.000 description 5
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 description 4
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 4
- 229920004897 Triton X-45 Polymers 0.000 description 4
- 125000000304 alkynyl group Chemical group 0.000 description 4
- 235000011114 ammonium hydroxide Nutrition 0.000 description 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 4
- 229910052681 coesite Inorganic materials 0.000 description 4
- 229910052906 cristobalite Inorganic materials 0.000 description 4
- 238000011049 filling Methods 0.000 description 4
- 239000000499 gel Substances 0.000 description 4
- 238000004128 high performance liquid chromatography Methods 0.000 description 4
- 125000004430 oxygen atom Chemical group O* 0.000 description 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 229910052682 stishovite Inorganic materials 0.000 description 4
- 238000004809 thin layer chromatography Methods 0.000 description 4
- 125000003396 thiol group Chemical group [H]S* 0.000 description 4
- 238000012546 transfer Methods 0.000 description 4
- 229910052905 tridymite Inorganic materials 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 239000013504 Triton X-100 Substances 0.000 description 3
- 229920004890 Triton X-100 Polymers 0.000 description 3
- 230000002378 acidificating effect Effects 0.000 description 3
- 125000002877 alkyl aryl group Chemical group 0.000 description 3
- 239000012491 analyte Substances 0.000 description 3
- 239000012300 argon atmosphere Substances 0.000 description 3
- 125000003710 aryl alkyl group Chemical group 0.000 description 3
- 238000004132 cross linking Methods 0.000 description 3
- 239000008367 deionised water Substances 0.000 description 3
- 229910021641 deionized water Inorganic materials 0.000 description 3
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 3
- 125000001183 hydrocarbyl group Chemical group 0.000 description 3
- 150000002431 hydrogen Chemical class 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 238000004811 liquid chromatography Methods 0.000 description 3
- 238000005259 measurement Methods 0.000 description 3
- 239000012071 phase Substances 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 229910000077 silane Inorganic materials 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 239000005051 trimethylchlorosilane Substances 0.000 description 3
- KDCGOANMDULRCW-UHFFFAOYSA-N 7H-purine Chemical compound N1=CNC2=NC=NC2=C1 KDCGOANMDULRCW-UHFFFAOYSA-N 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- RGSFGYAAUTVSQA-UHFFFAOYSA-N Cyclopentane Chemical compound C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 description 2
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 description 2
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 description 2
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
- 229910020381 SiO1.5 Inorganic materials 0.000 description 2
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 description 2
- CWRYPZZKDGJXCA-UHFFFAOYSA-N acenaphthene Chemical compound C1=CC(CC2)=C3C2=CC=CC3=C1 CWRYPZZKDGJXCA-UHFFFAOYSA-N 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 239000012736 aqueous medium Substances 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 2
- 239000000969 carrier Substances 0.000 description 2
- 150000001925 cycloalkenes Chemical class 0.000 description 2
- ZSWFCLXCOIISFI-UHFFFAOYSA-N cyclopentadiene Chemical compound C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 description 2
- 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 description 2
- 239000003480 eluent Substances 0.000 description 2
- 125000001072 heteroaryl group Chemical group 0.000 description 2
- 238000005470 impregnation Methods 0.000 description 2
- 125000001041 indolyl group Chemical group 0.000 description 2
- 238000005342 ion exchange Methods 0.000 description 2
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 description 2
- 239000000178 monomer Substances 0.000 description 2
- 125000001421 myristyl group Chemical group [H]C([*])([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])C([H])([H])[H] 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 description 2
- 150000007530 organic bases Chemical class 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 125000003386 piperidinyl group Chemical group 0.000 description 2
- 230000000379 polymerizing effect Effects 0.000 description 2
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 description 2
- 125000000719 pyrrolidinyl group Chemical group 0.000 description 2
- 125000000168 pyrrolyl group Chemical group 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000012798 spherical particle Substances 0.000 description 2
- 125000000547 substituted alkyl group Chemical group 0.000 description 2
- 229930192474 thiophene Natural products 0.000 description 2
- 150000003852 triazoles Chemical class 0.000 description 2
- CPUDPFPXCZDNGI-UHFFFAOYSA-N triethoxy(methyl)silane Chemical compound CCO[Si](C)(OCC)OCC CPUDPFPXCZDNGI-UHFFFAOYSA-N 0.000 description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 2
- KKZUMAMOMRDVKA-UHFFFAOYSA-N 2-chloropropane Chemical group [CH2]C(C)Cl KKZUMAMOMRDVKA-UHFFFAOYSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- LVZWSLJZHVFIQJ-UHFFFAOYSA-N Cyclopropane Chemical compound C1CC1 LVZWSLJZHVFIQJ-UHFFFAOYSA-N 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 229910003827 NRaRb Inorganic materials 0.000 description 1
- ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical group OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- HXGDTGSAIMULJN-UHFFFAOYSA-N acetnaphthylene Natural products C1=CC(C=C2)=C3C2=CC=CC3=C1 HXGDTGSAIMULJN-UHFFFAOYSA-N 0.000 description 1
- 125000004442 acylamino group Chemical group 0.000 description 1
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 1
- 125000005194 alkoxycarbonyloxy group Chemical group 0.000 description 1
- 125000004947 alkyl aryl amino group Chemical group 0.000 description 1
- 125000003806 alkyl carbonyl amino group Chemical group 0.000 description 1
- 125000004448 alkyl carbonyl group Chemical group 0.000 description 1
- 125000005196 alkyl carbonyloxy group Chemical group 0.000 description 1
- 125000004691 alkyl thio carbonyl group Chemical group 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- 125000001769 aryl amino group Chemical group 0.000 description 1
- 125000004658 aryl carbonyl amino group Chemical group 0.000 description 1
- 125000005199 aryl carbonyloxy group Chemical group 0.000 description 1
- 125000005110 aryl thio group Chemical group 0.000 description 1
- 125000005200 aryloxy carbonyloxy group Chemical group 0.000 description 1
- 125000004104 aryloxy group Chemical group 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 description 1
- 150000001555 benzenes Chemical class 0.000 description 1
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 description 1
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 description 1
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 description 1
- 239000000872 buffer Substances 0.000 description 1
- 125000003739 carbamimidoyl group Chemical group C(N)(=N)* 0.000 description 1
- 125000001951 carbamoylamino group Chemical group C(N)(=O)N* 0.000 description 1
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- 238000010561 standard procedure Methods 0.000 description 1
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- IZRJPHXTEXTLHY-UHFFFAOYSA-N triethoxy(2-triethoxysilylethyl)silane Chemical compound CCO[Si](OCC)(OCC)CC[Si](OCC)(OCC)OCC IZRJPHXTEXTLHY-UHFFFAOYSA-N 0.000 description 1
- PQDJYEQOELDLCP-UHFFFAOYSA-N trimethylsilane Chemical compound C[SiH](C)C PQDJYEQOELDLCP-UHFFFAOYSA-N 0.000 description 1
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Classifications
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- B01J20/3227—Impregnating or coating ; Solid sorbent compositions obtained from processes involving impregnating or coating characterised by the method for obtaining this coating or impregnating involving a post-treatment of the coated or impregnated product by end-capping, i.e. with or after the introduction of functional or ligand groups
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- 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
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- B01J20/3261—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 comprising a cyclic structure not containing any of the heteroatoms nitrogen, oxygen or sulfur, e.g. aromatic structures
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- B01J39/00—Cation exchange; Use of material as cation exchangers; Treatment of material for improving the cation exchange properties
- B01J39/26—Cation exchangers for chromatographic processes
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- B—PERFORMING OPERATIONS; TRANSPORTING
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- B01J41/00—Anion exchange; Use of material as anion exchangers; Treatment of material for improving the anion exchange properties
- B01J41/20—Anion exchangers for chromatographic processes
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- 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
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/29—Coated or structually defined flake, particle, cell, strand, strand portion, rod, filament, macroscopic fiber or mass thereof
- Y10T428/2982—Particulate matter [e.g., sphere, flake, etc.]
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- 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
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
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- Y10T428/2982—Particulate matter [e.g., sphere, flake, etc.]
- Y10T428/2991—Coated
- Y10T428/2993—Silicic or refractory material containing [e.g., tungsten oxide, glass, cement, etc.]
- Y10T428/2995—Silane, siloxane or silicone coating
Landscapes
- Chemical & Material Sciences (AREA)
- Analytical Chemistry (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Inorganic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Nanotechnology (AREA)
- Solid-Sorbent Or Filter-Aiding Compositions (AREA)
- Treatment Of Liquids With Adsorbents In General (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US24479599A | 1999-02-05 | 1999-02-05 | |
| US09/244,795 | 1999-02-05 | ||
| PCT/US2000/003052 WO2000045951A1 (en) | 1999-02-05 | 2000-02-04 | Porous inorganic/organic hybrid particles for chromatographic separations and process for its preparation |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2002536630A JP2002536630A (ja) | 2002-10-29 |
| JP2002536630A5 JP2002536630A5 (https=) | 2011-03-03 |
| JP4750280B2 true JP4750280B2 (ja) | 2011-08-17 |
Family
ID=22924139
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2000597060A Expired - Lifetime JP4750280B2 (ja) | 1999-02-05 | 2000-02-04 | クロマトグラフィ分離のための多孔質の無機／有機ハイブリッド粒子、及び、その調製プロセス |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US20010033931A1 (https=) |
| EP (2) | EP1163050B1 (https=) |
| JP (1) | JP4750280B2 (https=) |
| AT (2) | ATE464118T1 (https=) |
| AU (1) | AU2872100A (https=) |
| DE (2) | DE60044217D1 (https=) |
| WO (1) | WO2000045951A1 (https=) |
Families Citing this family (32)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6686035B2 (en) * | 1999-02-05 | 2004-02-03 | Waters Investments Limited | Porous inorganic/organic hybrid particles for chromatographic separations and process for their preparation |
| US6528167B2 (en) * | 2001-01-31 | 2003-03-04 | Waters Investments Limited | Porous hybrid particles with organic groups removed from the surface |
| US7250214B2 (en) * | 2001-08-09 | 2007-07-31 | Waters Investments Limited | Porous inorganic/organic hybrid monolith materials for chromatographic separations and process for their preparation |
| DE10393599T5 (de) | 2002-10-30 | 2005-10-27 | Waters Investments Ltd., New Castle | Poröse anorganische/organische Homogene copolymerische Hybridmaterialien für chromatographische Auftrennungen und Verfahren für deren Herstellung |
| US7887754B2 (en) | 2003-02-07 | 2011-02-15 | Waters Technologies Corporation | Polymeric solid supports for chromatography nanocolumns |
| DE112004000906T5 (de) * | 2003-05-28 | 2006-10-19 | Waters Investments Ltd., New Castle | Neue Nanoverbundstoffe und ihre Anwendung als Monolithsäulen |
| US7074491B2 (en) * | 2003-11-04 | 2006-07-11 | Dionex Corporation | Polar silanes for binding to substrates and use of the bound substrates |
| WO2005079427A2 (en) * | 2004-02-17 | 2005-09-01 | Waters Investments Limited | Porous hybrid monolith materials with organic groups removed from the surface |
| JP4538785B2 (ja) * | 2004-03-31 | 2010-09-08 | 和樹 中西 | 有機無機ハイブリッド系多孔質体の製造方法 |
| US8658277B2 (en) | 2004-07-30 | 2014-02-25 | Waters Technologies Corporation | Porous inorganic/organic hybrid materials with ordered domains for chromatographic separations and processes for their preparation |
| US10773186B2 (en) | 2004-07-30 | 2020-09-15 | Waters Technologies Corporation | Porous inorganic/organic hybrid materials with ordered domains for chromatographic separations and processes for their preparation |
| US7439272B2 (en) * | 2004-12-20 | 2008-10-21 | Varian, Inc. | Ultraporous sol gel monoliths |
| SE0502485L (sv) * | 2005-11-09 | 2007-05-10 | Peter Viberg | Partiklar |
| WO2008085435A1 (en) | 2007-01-12 | 2008-07-17 | Waters Investments Limited | Porous carbon-heteroatom-silicon hybrid inorganic/organic materials for chromatographic separations and process for the preparation thereof |
| CN101657325B (zh) * | 2007-02-21 | 2013-11-20 | 沃特世科技公司 | 用于色谱分离的具有高有机质含量和增进的孔几何特征的多孔无机/有机混合颗粒 |
| EP2262576B1 (en) * | 2008-04-08 | 2025-03-12 | Waters Technologies Corporation | Composite materials containing nanoparticles and their use in chromatography |
| US11439977B2 (en) | 2009-06-01 | 2022-09-13 | Waters Technologies Corporation | Hybrid material for chromatographic separations comprising a superficially porous core and a surrounding material |
| JP6151021B2 (ja) | 2009-06-01 | 2017-06-21 | ウオーターズ・テクノロジーズ・コーポレイシヨン | クロマトグラフ分離用ハイブリッド材料 |
| US10159911B2 (en) * | 2009-08-04 | 2018-12-25 | Waters Technologies Corporation | High purity chromatographic materials comprising an ionizable modifier |
| US10150098B2 (en) * | 2009-08-04 | 2018-12-11 | Waters Technologies Corporation | High purity chromatographic materials comprising an ionizable modifier |
| CN101797520B (zh) * | 2010-03-19 | 2011-11-09 | 山西大学 | 铝掺杂有机-无机杂化粘土催化剂及其制备方法和应用 |
| JP5856162B2 (ja) | 2010-07-26 | 2016-02-09 | ウオーターズ・テクノロジーズ・コーポレイシヨン | 粒度分布の狭い実質的に非多孔質のハイブリッドコアを含む表面多孔質材料 |
| WO2012166916A1 (en) * | 2011-06-03 | 2012-12-06 | Waters Technologies Corporation | Method of separation of lipid and biological molecular species using high purity chromatographic materials |
| JP2014521809A (ja) * | 2011-08-02 | 2014-08-28 | エイビーエス マテリアルズ インコーポレイテッド | ゾル−ゲル誘導組成物 |
| CN107754776B (zh) | 2012-05-15 | 2021-09-21 | 沃特世科技公司 | 色谱材料 |
| CN107106932B (zh) | 2015-01-15 | 2021-05-25 | 戴安公司 | 具有改进的pH稳定性的色谱材料、其制备方法和其用途 |
| US20190134604A1 (en) | 2016-03-06 | 2019-05-09 | Waters Technologies Corporation | Porous materials with controlled porosity; process for the preparation thereof; and use thereof for chromatographic separations |
| CN107029715B (zh) * | 2017-05-27 | 2019-12-03 | 上海应用技术大学 | 一种聚乙烯吡咯烷酮pvp改性的铑基催化剂及其制备方法和应用 |
| EP3744684A1 (en) | 2019-05-29 | 2020-12-02 | Nouryon Chemicals International B.V. | Porous silica particles |
| EP3744683A1 (en) * | 2019-05-29 | 2020-12-02 | Nouryon Chemicals International B.V. | Porous silica particles |
| EP4613370A1 (en) | 2024-03-04 | 2025-09-10 | Dionex Softron GmbH | Mixed mode chromatographic packing material |
| EP4613371A1 (en) | 2024-03-04 | 2025-09-10 | Dionex Softron GmbH | Mixed mode chromatographic packing material |
Citations (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5080400A (https=) * | 1973-11-16 | 1975-06-30 | ||
| JPS58120525A (ja) * | 1982-01-05 | 1983-07-18 | Asahi Glass Co Ltd | 珪酸塩中空球の製造方法 |
| JPS5954619A (ja) * | 1982-09-24 | 1984-03-29 | Asahi Glass Co Ltd | 珪酸塩粒状体の製造方法 |
| JPH0664915A (ja) * | 1992-06-19 | 1994-03-08 | Asahi Glass Co Ltd | 球状シリカの製造方法 |
| JPH07113011A (ja) * | 1993-10-18 | 1995-05-02 | Nippon Sheet Glass Co Ltd | 多孔質体及びこれを充填材とするカラム及びこれらの製造方法 |
| US5637135A (en) * | 1995-06-26 | 1997-06-10 | Capillary Technology Corporation | Chromatographic stationary phases and adsorbents from hybrid organic-inorganic sol-gels |
| JPH09278485A (ja) * | 1996-04-11 | 1997-10-28 | Tosoh Corp | 耐アルカリ性球状ガラスとその製造方法 |
| JPH11113011A (ja) * | 1997-09-29 | 1999-04-23 | Toshiba Corp | キャリアブースト補正回路 |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4724207A (en) * | 1984-02-02 | 1988-02-09 | Cuno Incorporated | Modified siliceous chromatographic supports |
| US5565142A (en) * | 1992-04-01 | 1996-10-15 | Deshpande; Ravindra | Preparation of high porosity xerogels by chemical surface modification. |
| US5378790A (en) * | 1992-09-16 | 1995-01-03 | E. I. Du Pont De Nemours & Co. | Single component inorganic/organic network materials and precursors thereof |
| JP3818689B2 (ja) * | 1996-01-16 | 2006-09-06 | 富士写真フイルム株式会社 | コロイド状シリカをコアとし、有機ポリマーをシェルとするコア／シェル状複合粒子の水性分散物及びその製造方法 |
| US5965202A (en) * | 1996-05-02 | 1999-10-12 | Lucent Technologies, Inc. | Hybrid inorganic-organic composite for use as an interlayer dielectric |
-
2000
- 2000-02-04 AT AT06014856T patent/ATE464118T1/de not_active IP Right Cessation
- 2000-02-04 JP JP2000597060A patent/JP4750280B2/ja not_active Expired - Lifetime
- 2000-02-04 DE DE60044217T patent/DE60044217D1/de not_active Expired - Lifetime
- 2000-02-04 WO PCT/US2000/003052 patent/WO2000045951A1/en not_active Ceased
- 2000-02-04 EP EP00907186A patent/EP1163050B1/en not_active Expired - Lifetime
- 2000-02-04 DE DE60032750T patent/DE60032750T2/de not_active Expired - Lifetime
- 2000-02-04 EP EP06014856A patent/EP1733786B1/en not_active Expired - Lifetime
- 2000-02-04 AT AT00907186T patent/ATE350154T1/de not_active IP Right Cessation
- 2000-02-04 AU AU28721/00A patent/AU2872100A/en not_active Abandoned
-
2001
- 2001-05-14 US US09/858,087 patent/US20010033931A1/en not_active Abandoned
Patent Citations (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5080400A (https=) * | 1973-11-16 | 1975-06-30 | ||
| JPS58120525A (ja) * | 1982-01-05 | 1983-07-18 | Asahi Glass Co Ltd | 珪酸塩中空球の製造方法 |
| JPS5954619A (ja) * | 1982-09-24 | 1984-03-29 | Asahi Glass Co Ltd | 珪酸塩粒状体の製造方法 |
| JPH0664915A (ja) * | 1992-06-19 | 1994-03-08 | Asahi Glass Co Ltd | 球状シリカの製造方法 |
| JPH07113011A (ja) * | 1993-10-18 | 1995-05-02 | Nippon Sheet Glass Co Ltd | 多孔質体及びこれを充填材とするカラム及びこれらの製造方法 |
| US5637135A (en) * | 1995-06-26 | 1997-06-10 | Capillary Technology Corporation | Chromatographic stationary phases and adsorbents from hybrid organic-inorganic sol-gels |
| JPH09278485A (ja) * | 1996-04-11 | 1997-10-28 | Tosoh Corp | 耐アルカリ性球状ガラスとその製造方法 |
| JPH11113011A (ja) * | 1997-09-29 | 1999-04-23 | Toshiba Corp | キャリアブースト補正回路 |
Also Published As
| Publication number | Publication date |
|---|---|
| EP1163050A1 (en) | 2001-12-19 |
| EP1733786B1 (en) | 2010-04-14 |
| EP1163050A4 (en) | 2003-08-06 |
| JP2002536630A (ja) | 2002-10-29 |
| DE60032750D1 (de) | 2007-02-15 |
| AU2872100A (en) | 2000-08-25 |
| EP1733786A1 (en) | 2006-12-20 |
| ATE350154T1 (de) | 2007-01-15 |
| WO2000045951A1 (en) | 2000-08-10 |
| DE60032750T2 (de) | 2007-11-08 |
| US20010033931A1 (en) | 2001-10-25 |
| EP1163050B1 (en) | 2007-01-03 |
| DE60044217D1 (de) | 2010-05-27 |
| ATE464118T1 (de) | 2010-04-15 |
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