JP2010519542A5 - - Google Patents
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- JP2010519542A5 JP2010519542A5 JP2009550915A JP2009550915A JP2010519542A5 JP 2010519542 A5 JP2010519542 A5 JP 2010519542A5 JP 2009550915 A JP2009550915 A JP 2009550915A JP 2009550915 A JP2009550915 A JP 2009550915A JP 2010519542 A5 JP2010519542 A5 JP 2010519542A5
- Authority
- JP
- Japan
- Prior art keywords
- particles
- organic
- porous inorganic
- organic hybrid
- inorganic
- 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.)
- Granted
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- 239000002245 particle Substances 0.000 claims 58
- 125000000217 alkyl group Chemical group 0.000 claims 11
- 239000011148 porous material Substances 0.000 claims 11
- 125000003342 alkenyl group Chemical group 0.000 claims 10
- 125000003118 aryl group Chemical group 0.000 claims 9
- 125000000304 alkynyl group Chemical group 0.000 claims 8
- 239000000178 monomer Substances 0.000 claims 8
- 125000000753 cycloalkyl group Chemical group 0.000 claims 7
- 125000001072 heteroaryl group Chemical group 0.000 claims 7
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims 7
- 238000012986 modification Methods 0.000 claims 7
- 230000004048 modification Effects 0.000 claims 7
- 239000000463 material Substances 0.000 claims 6
- 238000000034 method Methods 0.000 claims 6
- 125000000962 organic group Chemical group 0.000 claims 6
- 229910004298 SiO 2 Inorganic materials 0.000 claims 5
- 229910052799 carbon Inorganic materials 0.000 claims 5
- 230000003301 hydrolyzing effect Effects 0.000 claims 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 4
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical group [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 claims 4
- 125000003545 alkoxy group Chemical group 0.000 claims 4
- 239000011248 coating agent Substances 0.000 claims 4
- 238000000576 coating method Methods 0.000 claims 4
- 125000005375 organosiloxane group Chemical group 0.000 claims 4
- 229920000642 polymer Polymers 0.000 claims 4
- 125000005372 silanol group Chemical group 0.000 claims 4
- 125000004104 aryloxy group Chemical group 0.000 claims 3
- 238000004587 chromatography analysis Methods 0.000 claims 3
- 125000000524 functional group Chemical group 0.000 claims 3
- 239000012702 metal oxide precursor Substances 0.000 claims 3
- FIPWRIJSWJWJAI-UHFFFAOYSA-N Butyl carbitol 6-propylpiperonyl ether Chemical compound C1=C(CCC)C(COCCOCCOCCCC)=CC2=C1OCO2 FIPWRIJSWJWJAI-UHFFFAOYSA-N 0.000 claims 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims 2
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 claims 2
- 150000001336 alkenes Chemical class 0.000 claims 2
- 238000010335 hydrothermal treatment Methods 0.000 claims 2
- 238000004519 manufacturing process Methods 0.000 claims 2
- 239000003607 modifier Substances 0.000 claims 2
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims 2
- 150000001282 organosilanes Chemical class 0.000 claims 2
- 229960005235 piperonyl butoxide Drugs 0.000 claims 2
- 238000000926 separation method Methods 0.000 claims 2
- 229910052719 titanium Inorganic materials 0.000 claims 2
- 239000010936 titanium Substances 0.000 claims 2
- PYJJCSYBSYXGQQ-UHFFFAOYSA-N trichloro(octadecyl)silane Chemical compound CCCCCCCCCCCCCCCCCC[Si](Cl)(Cl)Cl PYJJCSYBSYXGQQ-UHFFFAOYSA-N 0.000 claims 2
- RCHUVCPBWWSUMC-UHFFFAOYSA-N trichloro(octyl)silane Chemical group CCCCCCCC[Si](Cl)(Cl)Cl RCHUVCPBWWSUMC-UHFFFAOYSA-N 0.000 claims 2
- 125000003837 (C1-C20) alkyl group Chemical group 0.000 claims 1
- 125000000923 (C1-C30) alkyl group Chemical group 0.000 claims 1
- QCEOZLISXJGWSW-UHFFFAOYSA-K 1,2,3,4,5-pentamethylcyclopentane;trichlorotitanium Chemical compound [Cl-].[Cl-].[Cl-].CC1=C(C)C(C)([Ti+3])C(C)=C1C QCEOZLISXJGWSW-UHFFFAOYSA-K 0.000 claims 1
- DKZRLCHWDNEKRH-UHFFFAOYSA-N 1-nonoxynonane Chemical compound CCCCCCCCCOCCCCCCCCC DKZRLCHWDNEKRH-UHFFFAOYSA-N 0.000 claims 1
- HITBDIPWYKTHIH-UHFFFAOYSA-N 2-[diethoxy(methyl)silyl]ethyl-diethoxy-methylsilane Chemical compound CCO[Si](C)(OCC)CC[Si](C)(OCC)OCC HITBDIPWYKTHIH-UHFFFAOYSA-N 0.000 claims 1
- KOAUHLUAUFQHBM-UHFFFAOYSA-M 2-methylprop-2-enoate;propan-2-olate;titanium(4+) Chemical compound [Ti+4].CC(C)[O-].CC(C)[O-].CC(C)[O-].CC(=C)C([O-])=O KOAUHLUAUFQHBM-UHFFFAOYSA-M 0.000 claims 1
- SDTMFDGELKWGFT-UHFFFAOYSA-N 2-methylpropan-2-olate Chemical compound CC(C)(C)[O-] SDTMFDGELKWGFT-UHFFFAOYSA-N 0.000 claims 1
- YHCCCMIWRBJYHG-UHFFFAOYSA-N 3-(2-ethylhexoxymethyl)heptane Chemical compound CCCCC(CC)COCC(CC)CCCC YHCCCMIWRBJYHG-UHFFFAOYSA-N 0.000 claims 1
- JJDGTGGQXAAVQX-UHFFFAOYSA-N 6-methyl-1-(6-methylheptoxy)heptane Chemical compound CC(C)CCCCCOCCCCCC(C)C JJDGTGGQXAAVQX-UHFFFAOYSA-N 0.000 claims 1
- IXTWGQGLWOKFHB-UHFFFAOYSA-N C(CC)O[Zr](OCCC)OCCC.C(CC(=O)C)(=O)OCCOC(C(=C)C)=O Chemical compound C(CC)O[Zr](OCCC)OCCC.C(CC(=O)C)(=O)OCCOC(C(=C)C)=O IXTWGQGLWOKFHB-UHFFFAOYSA-N 0.000 claims 1
- XVKRMWQDAAWGGH-UHFFFAOYSA-N CC([O-])C.CC([O-])C.CC([O-])C.[Ti+3].C(C(=C)C)(=O)OCCOC(CC(=O)C)=O Chemical compound CC([O-])C.CC([O-])C.CC([O-])C.[Ti+3].C(C(=C)C)(=O)OCCOC(CC(=O)C)=O XVKRMWQDAAWGGH-UHFFFAOYSA-N 0.000 claims 1
- UBPATBXONXTOHO-UHFFFAOYSA-N C[Ti](OC)(OC)(OC)C1C=CC=C1 Chemical compound C[Ti](OC)(OC)(OC)C1C=CC=C1 UBPATBXONXTOHO-UHFFFAOYSA-N 0.000 claims 1
- UGZUNKLJSDCQSC-UHFFFAOYSA-K C[Ti](Oc1ccccc1)(Oc1ccccc1)Oc1ccccc1 Chemical compound C[Ti](Oc1ccccc1)(Oc1ccccc1)Oc1ccccc1 UGZUNKLJSDCQSC-UHFFFAOYSA-K 0.000 claims 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims 1
- 230000005526 G1 to G0 transition Effects 0.000 claims 1
- AEMRFAOFKBGASW-UHFFFAOYSA-M Glycolate Chemical compound OCC([O-])=O AEMRFAOFKBGASW-UHFFFAOYSA-M 0.000 claims 1
- 229910002651 NO3 Inorganic materials 0.000 claims 1
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 claims 1
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 claims 1
- QCWXUUIWCKQGHC-UHFFFAOYSA-N Zirconium Chemical compound [Zr] QCWXUUIWCKQGHC-UHFFFAOYSA-N 0.000 claims 1
- 229910052782 aluminium Inorganic materials 0.000 claims 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 claims 1
- 238000005349 anion exchange Methods 0.000 claims 1
- 230000015572 biosynthetic process Effects 0.000 claims 1
- WRMFBHHNOHZECA-UHFFFAOYSA-N butan-2-olate Chemical compound CCC(C)[O-] WRMFBHHNOHZECA-UHFFFAOYSA-N 0.000 claims 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- QBLPAZNBFFURKB-UHFFFAOYSA-N carbanide;propan-2-ol;titanium Chemical group [CH3-].[Ti].CC(C)O.CC(C)O.CC(C)O QBLPAZNBFFURKB-UHFFFAOYSA-N 0.000 claims 1
- 150000007942 carboxylates Chemical class 0.000 claims 1
- 238000005341 cation exchange Methods 0.000 claims 1
- 150000001768 cations Chemical class 0.000 claims 1
- 229910010293 ceramic material Inorganic materials 0.000 claims 1
- 239000012700 ceramic precursor Substances 0.000 claims 1
- 239000003153 chemical reaction reagent Substances 0.000 claims 1
- GZGREZWGCWVAEE-UHFFFAOYSA-N chloro-dimethyl-octadecylsilane Chemical compound CCCCCCCCCCCCCCCCCC[Si](C)(C)Cl GZGREZWGCWVAEE-UHFFFAOYSA-N 0.000 claims 1
- DBKNGKYVNBJWHL-UHFFFAOYSA-N chloro-dimethyl-octylsilane Chemical compound CCCCCCCC[Si](C)(C)Cl DBKNGKYVNBJWHL-UHFFFAOYSA-N 0.000 claims 1
- 238000009833 condensation Methods 0.000 claims 1
- 230000005494 condensation Effects 0.000 claims 1
- -1 cyano, amino Chemical group 0.000 claims 1
- 125000004122 cyclic group Chemical group 0.000 claims 1
- 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 1
- 125000004663 dialkyl amino group Chemical group 0.000 claims 1
- 150000002009 diols Chemical class 0.000 claims 1
- 150000002148 esters Chemical class 0.000 claims 1
- HHFAWKCIHAUFRX-UHFFFAOYSA-N ethoxide Chemical compound CC[O-] HHFAWKCIHAUFRX-UHFFFAOYSA-N 0.000 claims 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
- 238000001914 filtration Methods 0.000 claims 1
- 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 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 claims 1
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 claims 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 claims 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 1
- 239000012528 membrane Substances 0.000 claims 1
- NBTOZLQBSIZIKS-UHFFFAOYSA-N methoxide Chemical compound [O-]C NBTOZLQBSIZIKS-UHFFFAOYSA-N 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- 239000000203 mixture Substances 0.000 claims 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 1
- 239000005416 organic matter Substances 0.000 claims 1
- RVTZCBVAJQQJTK-UHFFFAOYSA-N oxygen(2-);zirconium(4+) Chemical compound [O-2].[O-2].[Zr+4] RVTZCBVAJQQJTK-UHFFFAOYSA-N 0.000 claims 1
- 238000012856 packing Methods 0.000 claims 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 claims 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-M phenolate Chemical compound [O-]C1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-M 0.000 claims 1
- 238000006116 polymerization reaction Methods 0.000 claims 1
- AXLMPTNTPOWPLT-UHFFFAOYSA-N prop-2-enyl 3-oxobutanoate Chemical compound CC(=O)CC(=O)OCC=C AXLMPTNTPOWPLT-UHFFFAOYSA-N 0.000 claims 1
- IKNCGYCHMGNBCP-UHFFFAOYSA-N propan-1-olate Chemical compound CCC[O-] IKNCGYCHMGNBCP-UHFFFAOYSA-N 0.000 claims 1
- OGHBATFHNDZKSO-UHFFFAOYSA-N propan-2-olate Chemical compound CC(C)[O-] OGHBATFHNDZKSO-UHFFFAOYSA-N 0.000 claims 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- 230000001681 protective effect Effects 0.000 claims 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 1
- 239000000377 silicon dioxide Substances 0.000 claims 1
- 239000012798 spherical particle Substances 0.000 claims 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 claims 1
- IZRJPHXTEXTLHY-UHFFFAOYSA-N triethoxy(2-triethoxysilylethyl)silane Chemical group CCO[Si](OCC)(OCC)CC[Si](OCC)(OCC)OCC IZRJPHXTEXTLHY-UHFFFAOYSA-N 0.000 claims 1
- OSAJVUUALHWJEM-UHFFFAOYSA-N triethoxy(8-triethoxysilyloctyl)silane Chemical compound CCO[Si](OCC)(OCC)CCCCCCCC[Si](OCC)(OCC)OCC OSAJVUUALHWJEM-UHFFFAOYSA-N 0.000 claims 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 claims 1
- 229910052726 zirconium Inorganic materials 0.000 claims 1
- 229910001928 zirconium oxide Inorganic materials 0.000 claims 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US90265507P | 2007-02-21 | 2007-02-21 | |
| US60/902,655 | 2007-02-21 | ||
| PCT/US2008/002312 WO2008103423A1 (en) | 2007-02-21 | 2008-02-21 | Porous inorganic/organic hybrid particles having high organic content and enhanced pore geometry for chromatographic separations |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2010519542A JP2010519542A (ja) | 2010-06-03 |
| JP2010519542A5 true JP2010519542A5 (enExample) | 2011-01-13 |
| JP5152600B2 JP5152600B2 (ja) | 2013-02-27 |
Family
ID=39710396
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2009550915A Expired - Fee Related JP5152600B2 (ja) | 2007-02-21 | 2008-02-21 | 高い有機物含有量および向上性細孔形状を有するクロマトグラフィー分離用の多孔質無機／有機ハイブリッド粒子 |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US9120083B2 (enExample) |
| EP (1) | EP2150402A4 (enExample) |
| JP (1) | JP5152600B2 (enExample) |
| CN (2) | CN101657325B (enExample) |
| WO (1) | WO2008103423A1 (enExample) |
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| WO2004041398A2 (en) | 2002-10-30 | 2004-05-21 | Waters Investments Limited | Porous inorganic/organic hybrid materials and preparation thereof |
| 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 |
| US9440869B2 (en) | 2005-09-30 | 2016-09-13 | Abs Materials, Inc. | Sol-gel derived compositions |
| 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 |
| US20090208542A1 (en) * | 2008-02-18 | 2009-08-20 | Conopco, Inc., D/B/A Unilever | Product and method for transferring heated flowable cosmetic onto skin |
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| WO2012012311A2 (en) * | 2010-07-23 | 2012-01-26 | The Regents Of The University Of California | Compositions and methods for synthesis of organic-silica hybrid materials |
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| EP4613371A1 (en) | 2024-03-04 | 2025-09-10 | Dionex Softron GmbH | Mixed mode chromatographic packing material |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5403908A (en) * | 1989-10-06 | 1995-04-04 | Idemitsu Kosan Company, Limited | Aryl styrene-based copolymer |
| DE19751857A1 (de) * | 1997-11-22 | 1999-05-27 | Kronos Titan Gmbh | Phosphonatosiloxanbehandelte anorganische Partikel |
| EP1163050B1 (en) * | 1999-02-05 | 2007-01-03 | Waters Investments Limited | Preparation of porous inorganic/organic hybrid particles for chromatographic separations |
| US6686035B2 (en) * | 1999-02-05 | 2004-02-03 | Waters Investments Limited | Porous inorganic/organic hybrid particles for chromatographic separations and process for their preparation |
| US20060194919A1 (en) * | 1999-08-04 | 2006-08-31 | Lichtenhan Joseph D | Porosity control with polyhedral oligomeric silsesquioxanes |
| 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 |
| WO2004041398A2 (en) | 2002-10-30 | 2004-05-21 | Waters Investments Limited | Porous inorganic/organic hybrid materials and preparation thereof |
| DE112005000269T5 (de) * | 2004-02-17 | 2007-01-25 | Waters Investments Ltd., New Castle | Poröse Hybridmonolithmaterialien mit von der Oberfläche entfernten organischen Gruppen |
-
2008
- 2008-02-21 WO PCT/US2008/002312 patent/WO2008103423A1/en not_active Ceased
- 2008-02-21 CN CN2008800056207A patent/CN101657325B/zh not_active Expired - Fee Related
- 2008-02-21 EP EP08725902.4A patent/EP2150402A4/en not_active Ceased
- 2008-02-21 JP JP2009550915A patent/JP5152600B2/ja not_active Expired - Fee Related
- 2008-02-21 CN CN201310499813.5A patent/CN103551132B/zh not_active Expired - Fee Related
- 2008-02-21 US US12/516,964 patent/US9120083B2/en active Active
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