DE112015000675T5 - Chromatographisches Material und Verfahren für dessen Synthese - Google Patents
Chromatographisches Material und Verfahren für dessen Synthese Download PDFInfo
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- DE112015000675T5 DE112015000675T5 DE112015000675.3T DE112015000675T DE112015000675T5 DE 112015000675 T5 DE112015000675 T5 DE 112015000675T5 DE 112015000675 T DE112015000675 T DE 112015000675T DE 112015000675 T5 DE112015000675 T5 DE 112015000675T5
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- particulate material
- silsesquioxane
- particles
- producing
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- Prior art date
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- 238000000034 method Methods 0.000 title claims abstract description 110
- 239000000463 material Substances 0.000 title claims abstract description 51
- 230000008569 process Effects 0.000 title claims abstract description 35
- 230000015572 biosynthetic process Effects 0.000 title claims description 19
- 238000003786 synthesis reaction Methods 0.000 title description 11
- 239000002245 particle Substances 0.000 claims abstract description 257
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims abstract description 244
- 239000000377 silicon dioxide Substances 0.000 claims abstract description 80
- 239000000203 mixture Substances 0.000 claims abstract description 70
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical group [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 claims abstract description 60
- 239000011236 particulate material Substances 0.000 claims abstract description 55
- 230000007062 hydrolysis Effects 0.000 claims abstract description 35
- 238000006460 hydrolysis reaction Methods 0.000 claims abstract description 35
- 125000000962 organic group Chemical group 0.000 claims abstract description 20
- 230000003301 hydrolyzing effect Effects 0.000 claims abstract description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 136
- BOTDANWDWHJENH-UHFFFAOYSA-N Tetraethyl orthosilicate Chemical group CCO[Si](OCC)(OCC)OCC BOTDANWDWHJENH-UHFFFAOYSA-N 0.000 claims description 68
- 239000011148 porous material Substances 0.000 claims description 55
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 49
- 125000000217 alkyl group Chemical group 0.000 claims description 43
- 239000004094 surface-active agent Substances 0.000 claims description 40
- 238000004519 manufacturing process Methods 0.000 claims description 30
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 claims description 28
- 239000000908 ammonium hydroxide Substances 0.000 claims description 25
- 125000003118 aryl group Chemical group 0.000 claims description 21
- 238000001354 calcination Methods 0.000 claims description 18
- 229910052710 silicon Inorganic materials 0.000 claims description 18
- 238000009833 condensation Methods 0.000 claims description 13
- 238000004587 chromatography analysis Methods 0.000 claims description 12
- 229910004298 SiO 2 Inorganic materials 0.000 claims description 11
- 239000012071 phase Substances 0.000 claims description 11
- 229910000077 silane Inorganic materials 0.000 claims description 11
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 claims description 10
- 125000001183 hydrocarbyl group Chemical group 0.000 claims description 10
- 125000005372 silanol group Chemical group 0.000 claims description 10
- 238000001035 drying Methods 0.000 claims description 9
- SCPYDCQAZCOKTP-UHFFFAOYSA-N silanol Chemical compound [SiH3]O SCPYDCQAZCOKTP-UHFFFAOYSA-N 0.000 claims description 8
- 238000004811 liquid chromatography Methods 0.000 claims description 7
- 238000002414 normal-phase solid-phase extraction Methods 0.000 claims description 7
- 239000002244 precipitate Substances 0.000 claims description 7
- 239000003960 organic solvent Substances 0.000 claims description 6
- 238000006482 condensation reaction Methods 0.000 claims description 5
- 238000005406 washing Methods 0.000 claims description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 4
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 claims description 3
- 125000005211 alkyl trimethyl ammonium group Chemical group 0.000 claims description 2
- 239000003361 porogen Substances 0.000 claims description 2
- GKOZKEKDBJADSV-UHFFFAOYSA-N disilanol Chemical compound O[SiH2][SiH3] GKOZKEKDBJADSV-UHFFFAOYSA-N 0.000 claims 1
- 125000001453 quaternary ammonium group Chemical group 0.000 claims 1
- 238000004128 high performance liquid chromatography Methods 0.000 abstract description 8
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 120
- 239000000243 solution Substances 0.000 description 91
- -1 alkyl silicates Chemical class 0.000 description 62
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 36
- 125000001424 substituent group Chemical group 0.000 description 31
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 30
- 235000011114 ammonium hydroxide Nutrition 0.000 description 27
- 238000003756 stirring Methods 0.000 description 25
- 238000009826 distribution Methods 0.000 description 24
- 125000004432 carbon atom Chemical group C* 0.000 description 23
- 238000010438 heat treatment Methods 0.000 description 23
- LZZYPRNAOMGNLH-UHFFFAOYSA-M Cetrimonium bromide Chemical compound [Br-].CCCCCCCCCCCCCCCC[N+](C)(C)C LZZYPRNAOMGNLH-UHFFFAOYSA-M 0.000 description 22
- 239000000725 suspension Substances 0.000 description 20
- 238000005245 sintering Methods 0.000 description 19
- 239000011324 bead Substances 0.000 description 18
- 230000012010 growth Effects 0.000 description 18
- 238000006243 chemical reaction Methods 0.000 description 17
- 239000000839 emulsion Substances 0.000 description 17
- 238000013459 approach Methods 0.000 description 16
- 238000005119 centrifugation Methods 0.000 description 16
- 238000001878 scanning electron micrograph Methods 0.000 description 16
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 15
- 229910052799 carbon Inorganic materials 0.000 description 15
- 238000002360 preparation method Methods 0.000 description 15
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 14
- 239000002243 precursor Substances 0.000 description 13
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 12
- 230000005526 G1 to G0 transition Effects 0.000 description 12
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 12
- 229910052757 nitrogen Inorganic materials 0.000 description 12
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 11
- 239000000126 substance Substances 0.000 description 11
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 10
- 239000003153 chemical reaction reagent Substances 0.000 description 10
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 10
- 150000003254 radicals Chemical class 0.000 description 10
- 150000001875 compounds Chemical class 0.000 description 9
- 238000004945 emulsification Methods 0.000 description 9
- 125000001072 heteroaryl group Chemical group 0.000 description 9
- 150000004819 silanols Chemical class 0.000 description 9
- 239000000470 constituent Substances 0.000 description 8
- 238000000605 extraction Methods 0.000 description 8
- 125000004404 heteroalkyl group Chemical group 0.000 description 8
- 125000005842 heteroatom Chemical group 0.000 description 8
- 239000010703 silicon Substances 0.000 description 8
- 125000002947 alkylene group Chemical group 0.000 description 7
- 239000004615 ingredient Substances 0.000 description 7
- RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 7
- 239000002585 base Substances 0.000 description 6
- 238000002474 experimental method Methods 0.000 description 6
- 239000000499 gel Substances 0.000 description 6
- 125000000592 heterocycloalkyl group Chemical group 0.000 description 6
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 6
- 239000007788 liquid Substances 0.000 description 6
- 239000003921 oil Substances 0.000 description 6
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 6
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 5
- 239000004215 Carbon black (E152) Substances 0.000 description 5
- 230000002378 acidificating effect Effects 0.000 description 5
- 239000000654 additive Substances 0.000 description 5
- 230000005494 condensation Effects 0.000 description 5
- 238000001914 filtration Methods 0.000 description 5
- 125000004474 heteroalkylene group Chemical group 0.000 description 5
- 229910052739 hydrogen Inorganic materials 0.000 description 5
- 238000005259 measurement Methods 0.000 description 5
- 239000011259 mixed solution Substances 0.000 description 5
- 239000002105 nanoparticle Substances 0.000 description 5
- 239000012299 nitrogen atmosphere Substances 0.000 description 5
- 125000004430 oxygen atom Chemical group O* 0.000 description 5
- 230000000704 physical effect Effects 0.000 description 5
- 238000000926 separation method Methods 0.000 description 5
- 229910052717 sulfur Inorganic materials 0.000 description 5
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
- 125000001118 alkylidene group Chemical group 0.000 description 4
- HXCHRJMJMALFHP-UHFFFAOYSA-N azanium;ethanol;hydroxide Chemical compound N.O.CCO HXCHRJMJMALFHP-UHFFFAOYSA-N 0.000 description 4
- 238000010923 batch production Methods 0.000 description 4
- 239000003054 catalyst Substances 0.000 description 4
- 229930195733 hydrocarbon Natural products 0.000 description 4
- 239000001257 hydrogen Substances 0.000 description 4
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 4
- 239000000693 micelle Substances 0.000 description 4
- 239000004005 microsphere Substances 0.000 description 4
- 238000012986 modification Methods 0.000 description 4
- 230000004048 modification Effects 0.000 description 4
- 239000012429 reaction media Substances 0.000 description 4
- 241000894007 species Species 0.000 description 4
- 239000007858 starting material Substances 0.000 description 4
- 102100021792 Gamma-sarcoglycan Human genes 0.000 description 3
- 101000616435 Homo sapiens Gamma-sarcoglycan Proteins 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- NWGKJDSIEKMTRX-AAZCQSIUSA-N Sorbitan monooleate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O NWGKJDSIEKMTRX-AAZCQSIUSA-N 0.000 description 3
- 235000021355 Stearic acid Nutrition 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 3
- 125000003710 aryl alkyl group Chemical group 0.000 description 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 3
- 229910052796 boron Inorganic materials 0.000 description 3
- 125000000753 cycloalkyl group Chemical group 0.000 description 3
- 238000010908 decantation Methods 0.000 description 3
- 239000006185 dispersion Substances 0.000 description 3
- 239000003995 emulsifying agent Substances 0.000 description 3
- 238000009472 formulation Methods 0.000 description 3
- 125000000524 functional group Chemical group 0.000 description 3
- 150000002430 hydrocarbons Chemical class 0.000 description 3
- 238000010348 incorporation Methods 0.000 description 3
- 125000005647 linker group Chemical group 0.000 description 3
- 238000003760 magnetic stirring Methods 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- 239000003607 modifier Substances 0.000 description 3
- 125000004433 nitrogen atom Chemical group N* 0.000 description 3
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 3
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 3
- 229910052760 oxygen Inorganic materials 0.000 description 3
- 239000004033 plastic Substances 0.000 description 3
- 229920003023 plastic Polymers 0.000 description 3
- 238000006116 polymerization reaction Methods 0.000 description 3
- XTUSEBKMEQERQV-UHFFFAOYSA-N propan-2-ol;hydrate Chemical compound O.CC(C)O XTUSEBKMEQERQV-UHFFFAOYSA-N 0.000 description 3
- 150000003839 salts Chemical group 0.000 description 3
- 239000000741 silica gel Substances 0.000 description 3
- 229910002027 silica gel Inorganic materials 0.000 description 3
- 235000012239 silicon dioxide Nutrition 0.000 description 3
- 239000002002 slurry Substances 0.000 description 3
- 238000003980 solgel method Methods 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 239000008117 stearic acid Substances 0.000 description 3
- 125000004434 sulfur atom Chemical group 0.000 description 3
- 239000006228 supernatant Substances 0.000 description 3
- RNAMYOYQYRYFQY-UHFFFAOYSA-N 2-(4,4-difluoropiperidin-1-yl)-6-methoxy-n-(1-propan-2-ylpiperidin-4-yl)-7-(3-pyrrolidin-1-ylpropoxy)quinazolin-4-amine Chemical compound N1=C(N2CCC(F)(F)CC2)N=C2C=C(OCCCN3CCCC3)C(OC)=CC2=C1NC1CCN(C(C)C)CC1 RNAMYOYQYRYFQY-UHFFFAOYSA-N 0.000 description 2
- 238000004438 BET method Methods 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical group CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- 230000000996 additive effect Effects 0.000 description 2
- 238000004220 aggregation Methods 0.000 description 2
- 230000002776 aggregation Effects 0.000 description 2
- 125000003342 alkenyl group Chemical group 0.000 description 2
- 125000003545 alkoxy group Chemical group 0.000 description 2
- 125000000304 alkynyl group Chemical group 0.000 description 2
- 229910021529 ammonia Inorganic materials 0.000 description 2
- ZXVOCOLRQJZVBW-UHFFFAOYSA-N azane;ethanol Chemical compound N.CCO ZXVOCOLRQJZVBW-UHFFFAOYSA-N 0.000 description 2
- 239000000919 ceramic Substances 0.000 description 2
- WOWHHFRSBJGXCM-UHFFFAOYSA-M cetyltrimethylammonium chloride Chemical compound [Cl-].CCCCCCCCCCCCCCCC[N+](C)(C)C WOWHHFRSBJGXCM-UHFFFAOYSA-M 0.000 description 2
- 238000013375 chromatographic separation Methods 0.000 description 2
- 239000007771 core particle Substances 0.000 description 2
- 230000001186 cumulative effect Effects 0.000 description 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 2
- 238000003795 desorption Methods 0.000 description 2
- 238000001514 detection method Methods 0.000 description 2
- 238000010790 dilution Methods 0.000 description 2
- 239000012895 dilution Substances 0.000 description 2
- VFFDVELHRCMPLY-UHFFFAOYSA-N dimethyldodecyl amine Natural products CC(C)CCCCCCCCCCCN VFFDVELHRCMPLY-UHFFFAOYSA-N 0.000 description 2
- IDGUHHHQCWSQLU-UHFFFAOYSA-N ethanol;hydrate Chemical compound O.CCO IDGUHHHQCWSQLU-UHFFFAOYSA-N 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 125000001188 haloalkyl group Chemical group 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- 125000005843 halogen group Chemical group 0.000 description 2
- 238000010335 hydrothermal treatment Methods 0.000 description 2
- 238000003780 insertion Methods 0.000 description 2
- 230000037431 insertion Effects 0.000 description 2
- 230000001788 irregular Effects 0.000 description 2
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 2
- 229910052753 mercury Inorganic materials 0.000 description 2
- GBMDVOWEEQVZKZ-UHFFFAOYSA-N methanol;hydrate Chemical compound O.OC GBMDVOWEEQVZKZ-UHFFFAOYSA-N 0.000 description 2
- QPJVMBTYPHYUOC-UHFFFAOYSA-N methyl benzoate Chemical compound COC(=O)C1=CC=CC=C1 QPJVMBTYPHYUOC-UHFFFAOYSA-N 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 239000011859 microparticle Substances 0.000 description 2
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 description 2
- YWFWDNVOPHGWMX-UHFFFAOYSA-N n,n-dimethyldodecan-1-amine Chemical compound CCCCCCCCCCCCN(C)C YWFWDNVOPHGWMX-UHFFFAOYSA-N 0.000 description 2
- 238000005580 one pot reaction Methods 0.000 description 2
- 238000012856 packing Methods 0.000 description 2
- 238000006068 polycondensation reaction Methods 0.000 description 2
- 238000002459 porosimetry Methods 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- KCIKCCHXZMLVDE-UHFFFAOYSA-N silanediol Chemical group O[SiH2]O KCIKCCHXZMLVDE-UHFFFAOYSA-N 0.000 description 2
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 2
- 238000000527 sonication Methods 0.000 description 2
- 238000001179 sorption measurement Methods 0.000 description 2
- 239000012798 spherical particle Substances 0.000 description 2
- QEMXHQIAXOOASZ-UHFFFAOYSA-N tetramethylammonium Chemical compound C[N+](C)(C)C QEMXHQIAXOOASZ-UHFFFAOYSA-N 0.000 description 2
- ZFXYFBGIUFBOJW-UHFFFAOYSA-N theophylline Chemical compound O=C1N(C)C(=O)N(C)C2=C1NC=N2 ZFXYFBGIUFBOJW-UHFFFAOYSA-N 0.000 description 2
- 238000007669 thermal treatment Methods 0.000 description 2
- 238000011282 treatment Methods 0.000 description 2
- 125000004417 unsaturated alkyl group Chemical group 0.000 description 2
- 125000000196 1,4-pentadienyl group Chemical group [H]C([*])=C([H])C([H])([H])C([H])=C([H])[H] 0.000 description 1
- 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 description 1
- 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 125000001462 1-pyrrolyl group Chemical group [*]N1C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 description 1
- 125000004174 2-benzimidazolyl group Chemical group [H]N1C(*)=NC2=C([H])C([H])=C([H])C([H])=C12 0.000 description 1
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 description 1
- 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 description 1
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 125000000389 2-pyrrolyl group Chemical group [H]N1C([*])=C([H])C([H])=C1[H] 0.000 description 1
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 description 1
- 125000000474 3-butynyl group Chemical group [H]C#CC([H])([H])C([H])([H])* 0.000 description 1
- 125000003682 3-furyl group Chemical group O1C([H])=C([*])C([H])=C1[H] 0.000 description 1
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 description 1
- 125000001397 3-pyrrolyl group Chemical group [H]N1C([H])=C([*])C([H])=C1[H] 0.000 description 1
- 125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 description 1
- TYMLOMAKGOJONV-UHFFFAOYSA-N 4-nitroaniline Chemical compound NC1=CC=C([N+]([O-])=O)C=C1 TYMLOMAKGOJONV-UHFFFAOYSA-N 0.000 description 1
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 1
- KDDQRKBRJSGMQE-UHFFFAOYSA-N 4-thiazolyl Chemical group [C]1=CSC=N1 KDDQRKBRJSGMQE-UHFFFAOYSA-N 0.000 description 1
- CWDWFSXUQODZGW-UHFFFAOYSA-N 5-thiazolyl Chemical group [C]1=CN=CS1 CWDWFSXUQODZGW-UHFFFAOYSA-N 0.000 description 1
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 1
- 239000004971 Cross linker Substances 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 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 1
- 229910003849 O-Si Inorganic materials 0.000 description 1
- 229910003872 O—Si Inorganic materials 0.000 description 1
- 229910020381 SiO1.5 Inorganic materials 0.000 description 1
- 229910002808 Si–O–Si Inorganic materials 0.000 description 1
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 1
- 229930006000 Sucrose Natural products 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 125000003282 alkyl amino group Chemical group 0.000 description 1
- 125000004414 alkyl thio group Chemical group 0.000 description 1
- 125000005237 alkyleneamino group Chemical group 0.000 description 1
- 125000005238 alkylenediamino group Chemical group 0.000 description 1
- 125000005530 alkylenedioxy group Chemical group 0.000 description 1
- 125000005529 alkyleneoxy group Chemical group 0.000 description 1
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- 125000005165 aryl thioxy group Chemical group 0.000 description 1
- 125000004104 aryloxy group Chemical group 0.000 description 1
- 125000000319 biphenyl-4-yl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 1
- 125000001246 bromo group Chemical group Br* 0.000 description 1
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- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J2220/00—Aspects relating to sorbent materials
- B01J2220/80—Aspects related to sorbents specially adapted for preparative, analytical or investigative chromatography
- B01J2220/82—Shaped bodies, e.g. monoliths, plugs, tubes, continuous beds
- B01J2220/825—Shaped bodies, e.g. monoliths, plugs, tubes, continuous beds comprising a cladding or external coating
Landscapes
- Chemical & Material Sciences (AREA)
- Analytical Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Chemistry (AREA)
- Nanotechnology (AREA)
- Engineering & Computer Science (AREA)
- Inorganic Chemistry (AREA)
- Physics & Mathematics (AREA)
- Thermal Sciences (AREA)
- Silicon Polymers (AREA)
- Solid-Sorbent Or Filter-Aiding Compositions (AREA)
- Treatment Of Liquids With Adsorbents In General (AREA)
- Silicon Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US14/175,689 US20150224473A1 (en) | 2014-02-07 | 2014-02-07 | Chromatographic material and methods for the synthesis thereof |
| US14/175,689 | 2014-02-07 | ||
| PCT/EP2015/052511 WO2015118105A1 (en) | 2014-02-07 | 2015-02-06 | Chromatographic material and methods for the synthesis thereof |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE112015000675T5 true DE112015000675T5 (de) | 2016-10-27 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE112015000675.3T Pending DE112015000675T5 (de) | 2014-02-07 | 2015-02-06 | Chromatographisches Material und Verfahren für dessen Synthese |
Country Status (6)
| Country | Link |
|---|---|
| US (2) | US20150224473A1 (enExample) |
| JP (1) | JP6480471B2 (enExample) |
| CN (1) | CN105960281B (enExample) |
| DE (1) | DE112015000675T5 (enExample) |
| GB (1) | GB2540269B (enExample) |
| WO (1) | WO2015118105A1 (enExample) |
Families Citing this family (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105233811B (zh) * | 2015-10-16 | 2018-03-09 | 苏州大学 | 一种键合型色谱柱固定相及其制备方法 |
| CN110520430B (zh) * | 2017-04-20 | 2023-09-05 | 国立研究开发法人产业技术综合研究所 | 硅烷醇化合物及硅烷醇化合物的制造方法 |
| CN108774413A (zh) * | 2018-04-13 | 2018-11-09 | 太仓运通新材料科技有限公司 | 纳米二氧化硅分散液及其制备方法 |
| US10661250B2 (en) * | 2018-04-13 | 2020-05-26 | Agilent Technologies, Inc. | Synthetic silica as packing material in supported liquid extraction |
| CN111468087B (zh) * | 2019-01-23 | 2023-05-02 | 中国科学院大连化学物理研究所 | 一种修饰杂化整体材料及其制备和应用 |
| CN112619705B (zh) * | 2019-09-24 | 2023-08-04 | 中国石油化工股份有限公司 | 环氧烷烃加成反应催化剂及其应用 |
| US11964874B2 (en) | 2020-06-09 | 2024-04-23 | Agilent Technologies, Inc. | Etched non-porous particles and method of producing thereof |
| CN113797903A (zh) * | 2020-06-12 | 2021-12-17 | 江苏汉邦科技有限公司 | 一种杂化硅胶色谱填料的制备方法 |
| US20220354757A1 (en) * | 2021-05-04 | 2022-11-10 | Momentive Performance Materials Japan Llc | Method for producing silica particles and their use in cosmetic compositions |
| CN114133571B (zh) * | 2021-10-18 | 2022-10-04 | 镇江海关综合技术中心 | Pmo(slltp-poss)亲水微球及其制备方法与应用 |
| CN114878734B (zh) * | 2022-03-28 | 2023-12-01 | 中国科学院上海微系统与信息技术研究所 | 基于逐层沉积介孔二氧化硅为固定相的微色谱柱制备方法 |
| EP4279454A4 (en) * | 2022-03-29 | 2024-04-03 | Nissan Chemical Corporation | Cage silicate and method for producing same |
| WO2023188930A1 (ja) * | 2022-03-29 | 2023-10-05 | 日産化学株式会社 | 層状ケイ酸塩の製造方法、及びシリカナノシートの製造等におけるその応用 |
| TWI802377B (zh) | 2022-04-20 | 2023-05-11 | 台灣創新材料股份有限公司 | 用於吸附層析術的靜相媒質及其製造方法 |
| CN115178245A (zh) * | 2022-06-21 | 2022-10-14 | 南通裕弘分析仪器有限公司 | 一种有机无机杂化硅胶颗粒的制备方法及其应用 |
| US20240229242A9 (en) * | 2022-10-20 | 2024-07-11 | The Regents Of The University Of Michigan | Additive Solution-Processed Structural Colors |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2357184A1 (de) | 1973-11-16 | 1975-05-22 | Merck Patent Gmbh | Verfahren zur herstellung von organisch modifizierten siliciumdioxiden |
| JPH04269656A (ja) * | 1991-02-26 | 1992-09-25 | Toray Dow Corning Silicone Co Ltd | 液体クロマトグラフィー用充填剤 |
| US6686035B2 (en) | 1999-02-05 | 2004-02-03 | Waters Investments Limited | Porous inorganic/organic hybrid particles for chromatographic separations and process for their preparation |
| JP2008530312A (ja) * | 2005-02-14 | 2008-08-07 | ハイブリッド・プラスティックス・インコーポレイテッド | ポリヘドラルオリゴメリックシルセスキオキサンによる多孔性制御 |
| JP5358570B2 (ja) * | 2007-07-13 | 2013-12-04 | ユニバーシティ・カレッジ・コークーナショナル・ユニバーシティ・オブ・アイルランド,コーク | 微粒子合成方法 |
| US8063113B2 (en) * | 2008-04-23 | 2011-11-22 | Momentive Performance Materials Inc. | Polyurethane foam-forming compositions containing polysilsesquioxane cell opening agents |
| US20120205315A1 (en) * | 2011-02-14 | 2012-08-16 | Dionex Corporation | Nanometer size chemical modified materials and uses |
-
2014
- 2014-02-07 US US14/175,689 patent/US20150224473A1/en not_active Abandoned
-
2015
- 2015-02-06 GB GB1610858.1A patent/GB2540269B/en active Active
- 2015-02-06 WO PCT/EP2015/052511 patent/WO2015118105A1/en not_active Ceased
- 2015-02-06 DE DE112015000675.3T patent/DE112015000675T5/de active Pending
- 2015-02-06 JP JP2016568118A patent/JP6480471B2/ja active Active
- 2015-02-06 CN CN201580006617.7A patent/CN105960281B/zh active Active
-
2019
- 2019-04-08 US US16/378,296 patent/US20190232252A1/en not_active Abandoned
Also Published As
| Publication number | Publication date |
|---|---|
| GB2540269B (en) | 2020-08-19 |
| JP2017512132A (ja) | 2017-05-18 |
| CN105960281B (zh) | 2018-10-26 |
| GB2540269A (en) | 2017-01-11 |
| US20150224473A1 (en) | 2015-08-13 |
| US20190232252A1 (en) | 2019-08-01 |
| WO2015118105A1 (en) | 2015-08-13 |
| CN105960281A (zh) | 2016-09-21 |
| GB201610858D0 (en) | 2016-08-03 |
| JP6480471B2 (ja) | 2019-03-13 |
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