JP7156146B2 - 親水性材料の疎水化方法 - Google Patents
親水性材料の疎水化方法 Download PDFInfo
- Publication number
- JP7156146B2 JP7156146B2 JP2019074772A JP2019074772A JP7156146B2 JP 7156146 B2 JP7156146 B2 JP 7156146B2 JP 2019074772 A JP2019074772 A JP 2019074772A JP 2019074772 A JP2019074772 A JP 2019074772A JP 7156146 B2 JP7156146 B2 JP 7156146B2
- Authority
- JP
- Japan
- Prior art keywords
- group
- hydrophobized
- hollow fiber
- hydrophobic group
- fiber material
- 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.)
- Active
Links
- 239000000463 material Substances 0.000 title claims description 76
- 238000000034 method Methods 0.000 title claims description 29
- 230000002209 hydrophobic effect Effects 0.000 title description 3
- 125000001165 hydrophobic group Chemical group 0.000 claims description 45
- 239000000758 substrate Substances 0.000 claims description 39
- 238000006243 chemical reaction Methods 0.000 claims description 37
- 150000001413 amino acids Chemical class 0.000 claims description 35
- 239000003795 chemical substances by application Substances 0.000 claims description 25
- 239000012510 hollow fiber Substances 0.000 claims description 18
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 claims description 18
- 238000004519 manufacturing process Methods 0.000 claims description 15
- 238000000926 separation method Methods 0.000 claims description 14
- IJOOHPMOJXWVHK-UHFFFAOYSA-N chlorotrimethylsilane Chemical group C[Si](C)(C)Cl IJOOHPMOJXWVHK-UHFFFAOYSA-N 0.000 claims description 10
- 125000003545 alkoxy group Chemical group 0.000 claims description 8
- 125000005843 halogen group Chemical group 0.000 claims description 8
- 125000001183 hydrocarbyl group Chemical group 0.000 claims description 7
- 125000003118 aryl group Chemical group 0.000 claims description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims description 6
- GZGREZWGCWVAEE-UHFFFAOYSA-N chloro-dimethyl-octadecylsilane Chemical compound CCCCCCCCCCCCCCCCCC[Si](C)(C)Cl GZGREZWGCWVAEE-UHFFFAOYSA-N 0.000 claims description 6
- 125000001424 substituent group Chemical group 0.000 claims description 5
- 239000005051 trimethylchlorosilane Substances 0.000 claims description 5
- 239000004475 Arginine Substances 0.000 claims description 4
- 125000001931 aliphatic group Chemical group 0.000 claims description 4
- ODKSFYDXXFIFQN-UHFFFAOYSA-N arginine Natural products OC(=O)C(N)CCCNC(N)=N ODKSFYDXXFIFQN-UHFFFAOYSA-N 0.000 claims description 4
- 229920006395 saturated elastomer Polymers 0.000 claims description 4
- PYJJCSYBSYXGQQ-UHFFFAOYSA-N trichloro(octadecyl)silane Chemical compound CCCCCCCCCCCCCCCCCC[Si](Cl)(Cl)Cl PYJJCSYBSYXGQQ-UHFFFAOYSA-N 0.000 claims description 4
- AHLPHDHHMVZTML-BYPYZUCNSA-N L-Ornithine Chemical compound NCCC[C@H](N)C(O)=O AHLPHDHHMVZTML-BYPYZUCNSA-N 0.000 claims description 3
- ODKSFYDXXFIFQN-BYPYZUCNSA-P L-argininium(2+) Chemical compound NC(=[NH2+])NCCC[C@H]([NH3+])C(O)=O ODKSFYDXXFIFQN-BYPYZUCNSA-P 0.000 claims description 3
- HNDVDQJCIGZPNO-YFKPBYRVSA-N L-histidine Chemical compound OC(=O)[C@@H](N)CC1=CN=CN1 HNDVDQJCIGZPNO-YFKPBYRVSA-N 0.000 claims description 3
- KDXKERNSBIXSRK-YFKPBYRVSA-N L-lysine Chemical compound NCCCC[C@H](N)C(O)=O KDXKERNSBIXSRK-YFKPBYRVSA-N 0.000 claims description 3
- QIVBCDIJIAJPQS-VIFPVBQESA-N L-tryptophane Chemical compound C1=CC=C2C(C[C@H](N)C(O)=O)=CNC2=C1 QIVBCDIJIAJPQS-VIFPVBQESA-N 0.000 claims description 3
- KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 claims description 3
- 239000004472 Lysine Substances 0.000 claims description 3
- AHLPHDHHMVZTML-UHFFFAOYSA-N Orn-delta-NH2 Natural products NCCCC(N)C(O)=O AHLPHDHHMVZTML-UHFFFAOYSA-N 0.000 claims description 3
- UTJLXEIPEHZYQJ-UHFFFAOYSA-N Ornithine Natural products OC(=O)C(C)CCCN UTJLXEIPEHZYQJ-UHFFFAOYSA-N 0.000 claims description 3
- QIVBCDIJIAJPQS-UHFFFAOYSA-N Tryptophan Natural products C1=CC=C2C(CC(N)C(O)=O)=CNC2=C1 QIVBCDIJIAJPQS-UHFFFAOYSA-N 0.000 claims description 3
- FQEKAFQSVPLXON-UHFFFAOYSA-N butyl(trichloro)silane Chemical compound CCCC[Si](Cl)(Cl)Cl FQEKAFQSVPLXON-UHFFFAOYSA-N 0.000 claims description 3
- MXOSTENCGSDMRE-UHFFFAOYSA-N butyl-chloro-dimethylsilane Chemical compound CCCC[Si](C)(C)Cl MXOSTENCGSDMRE-UHFFFAOYSA-N 0.000 claims description 3
- 229910052801 chlorine Inorganic materials 0.000 claims description 3
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 3
- ZLZGHBNDPINFKG-UHFFFAOYSA-N chloro-decyl-dimethylsilane Chemical compound CCCCCCCCCC[Si](C)(C)Cl ZLZGHBNDPINFKG-UHFFFAOYSA-N 0.000 claims description 3
- DBKNGKYVNBJWHL-UHFFFAOYSA-N chloro-dimethyl-octylsilane Chemical compound CCCCCCCC[Si](C)(C)Cl DBKNGKYVNBJWHL-UHFFFAOYSA-N 0.000 claims description 3
- KWYZNESIGBQHJK-UHFFFAOYSA-N chloro-dimethyl-phenylsilane Chemical compound C[Si](C)(Cl)C1=CC=CC=C1 KWYZNESIGBQHJK-UHFFFAOYSA-N 0.000 claims description 3
- HXVPUKPVLPTVCQ-UHFFFAOYSA-N chloro-dimethyl-propylsilane Chemical compound CCC[Si](C)(C)Cl HXVPUKPVLPTVCQ-UHFFFAOYSA-N 0.000 claims description 3
- DLLABNOCKQMTEJ-UHFFFAOYSA-N chloro-dodecyl-dimethylsilane Chemical compound CCCCCCCCCCCC[Si](C)(C)Cl DLLABNOCKQMTEJ-UHFFFAOYSA-N 0.000 claims description 3
- AQWKIRVGNVDYEZ-UHFFFAOYSA-N chloro-hexadecyl-dimethylsilane Chemical compound CCCCCCCCCCCCCCCC[Si](C)(C)Cl AQWKIRVGNVDYEZ-UHFFFAOYSA-N 0.000 claims description 3
- JQYKSDDVPXVEOL-UHFFFAOYSA-N chloro-hexyl-dimethylsilane Chemical compound CCCCCC[Si](C)(C)Cl JQYKSDDVPXVEOL-UHFFFAOYSA-N 0.000 claims description 3
- 150000001875 compounds Chemical class 0.000 claims description 3
- HNDVDQJCIGZPNO-UHFFFAOYSA-N histidine Natural products OC(=O)C(N)CC1=CN=CN1 HNDVDQJCIGZPNO-UHFFFAOYSA-N 0.000 claims description 3
- 150000003961 organosilicon compounds Chemical class 0.000 claims description 3
- 229960003104 ornithine Drugs 0.000 claims description 3
- 239000005054 phenyltrichlorosilane Substances 0.000 claims description 3
- 239000005053 propyltrichlorosilane Substances 0.000 claims description 3
- HLWCOIUDOLYBGD-UHFFFAOYSA-N trichloro(decyl)silane Chemical compound CCCCCCCCCC[Si](Cl)(Cl)Cl HLWCOIUDOLYBGD-UHFFFAOYSA-N 0.000 claims description 3
- BNCXNUWGWUZTCN-UHFFFAOYSA-N trichloro(dodecyl)silane Chemical compound CCCCCCCCCCCC[Si](Cl)(Cl)Cl BNCXNUWGWUZTCN-UHFFFAOYSA-N 0.000 claims description 3
- RYPYGDUZKOPBEL-UHFFFAOYSA-N trichloro(hexadecyl)silane Chemical compound CCCCCCCCCCCCCCCC[Si](Cl)(Cl)Cl RYPYGDUZKOPBEL-UHFFFAOYSA-N 0.000 claims description 3
- LFXJGGDONSCPOF-UHFFFAOYSA-N trichloro(hexyl)silane Chemical compound CCCCCC[Si](Cl)(Cl)Cl LFXJGGDONSCPOF-UHFFFAOYSA-N 0.000 claims description 3
- RCHUVCPBWWSUMC-UHFFFAOYSA-N trichloro(octyl)silane Chemical compound CCCCCCCC[Si](Cl)(Cl)Cl RCHUVCPBWWSUMC-UHFFFAOYSA-N 0.000 claims description 3
- ORVMIVQULIKXCP-UHFFFAOYSA-N trichloro(phenyl)silane Chemical compound Cl[Si](Cl)(Cl)C1=CC=CC=C1 ORVMIVQULIKXCP-UHFFFAOYSA-N 0.000 claims description 3
- DOEHJNBEOVLHGL-UHFFFAOYSA-N trichloro(propyl)silane Chemical compound CCC[Si](Cl)(Cl)Cl DOEHJNBEOVLHGL-UHFFFAOYSA-N 0.000 claims description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 27
- 239000000741 silica gel Substances 0.000 description 20
- 229910002027 silica gel Inorganic materials 0.000 description 20
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 17
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 16
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 16
- 239000000126 substance Substances 0.000 description 15
- VZSRBBMJRBPUNF-UHFFFAOYSA-N 2-(2,3-dihydro-1H-inden-2-ylamino)-N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]pyrimidine-5-carboxamide Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C(=O)NCCC(N1CC2=C(CC1)NN=N2)=O VZSRBBMJRBPUNF-UHFFFAOYSA-N 0.000 description 12
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 10
- 239000003054 catalyst Substances 0.000 description 9
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 8
- -1 octadecylsilyl Chemical group 0.000 description 8
- 230000000052 comparative effect Effects 0.000 description 7
- AFCARXCZXQIEQB-UHFFFAOYSA-N N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C(CCNC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)N1CC2=C(CC1)NN=N2 AFCARXCZXQIEQB-UHFFFAOYSA-N 0.000 description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
- 239000003153 chemical reaction reagent Substances 0.000 description 6
- 238000012856 packing Methods 0.000 description 6
- 125000005372 silanol group Chemical group 0.000 description 6
- 230000003373 anti-fouling effect Effects 0.000 description 5
- 230000003197 catalytic effect Effects 0.000 description 5
- 238000011282 treatment Methods 0.000 description 5
- 238000005406 washing Methods 0.000 description 5
- UBOXGVDOUJQMTN-UHFFFAOYSA-N 1,1,2-trichloroethane Chemical compound ClCC(Cl)Cl UBOXGVDOUJQMTN-UHFFFAOYSA-N 0.000 description 4
- 150000004982 aromatic amines Chemical class 0.000 description 4
- 239000007810 chemical reaction solvent Substances 0.000 description 4
- 230000001747 exhibiting effect Effects 0.000 description 4
- 239000002657 fibrous material Substances 0.000 description 4
- 230000007062 hydrolysis Effects 0.000 description 4
- 238000006460 hydrolysis reaction Methods 0.000 description 4
- 239000004065 semiconductor Substances 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 239000000835 fiber Substances 0.000 description 3
- 238000001249 flow field-flow fractionation Methods 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 238000006053 organic reaction Methods 0.000 description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
- 239000000377 silicon dioxide Substances 0.000 description 3
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- 229910008051 Si-OH Inorganic materials 0.000 description 2
- 229910006358 Si—OH Inorganic materials 0.000 description 2
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 2
- 239000000945 filler Substances 0.000 description 2
- 238000004128 high performance liquid chromatography Methods 0.000 description 2
- 230000001771 impaired effect Effects 0.000 description 2
- 238000011866 long-term treatment Methods 0.000 description 2
- 229910044991 metal oxide Inorganic materials 0.000 description 2
- 150000004706 metal oxides Chemical class 0.000 description 2
- 231100000252 nontoxic Toxicity 0.000 description 2
- 230000003000 nontoxic effect Effects 0.000 description 2
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 239000004627 regenerated cellulose Substances 0.000 description 2
- 150000003335 secondary amines Chemical class 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 239000002344 surface layer Substances 0.000 description 2
- 150000003512 tertiary amines Chemical class 0.000 description 2
- WROMPOXWARCANT-UHFFFAOYSA-N tfa trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.OC(=O)C(F)(F)F WROMPOXWARCANT-UHFFFAOYSA-N 0.000 description 2
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 2
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- ODKSFYDXXFIFQN-BYPYZUCNSA-N L-arginine Chemical compound OC(=O)[C@@H](N)CCCN=C(N)N ODKSFYDXXFIFQN-BYPYZUCNSA-N 0.000 description 1
- 238000005903 acid hydrolysis reaction Methods 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- 150000007514 bases Chemical class 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- AZUXXYCNTKYZJB-UHFFFAOYSA-N chloro(octadecyl)silane Chemical compound CCCCCCCCCCCCCCCCCC[SiH2]Cl AZUXXYCNTKYZJB-UHFFFAOYSA-N 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 125000002704 decyl 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])* 0.000 description 1
- 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 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000010408 film Substances 0.000 description 1
- 229940083124 ganglion-blocking antiadrenergic secondary and tertiary amines Drugs 0.000 description 1
- FFUAGWLWBBFQJT-UHFFFAOYSA-N hexamethyldisilazane Chemical compound C[Si](C)(C)N[Si](C)(C)C FFUAGWLWBBFQJT-UHFFFAOYSA-N 0.000 description 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 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000010410 layer Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 125000002960 margaryl 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])[H] 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000011259 mixed solution Substances 0.000 description 1
- 239000002808 molecular sieve Substances 0.000 description 1
- 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 1
- 125000001196 nonadecyl 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])C([H])([H])[H] 0.000 description 1
- 125000001400 nonyl 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])[H] 0.000 description 1
- 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 1
- 125000001117 oleyl 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])=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])[H] 0.000 description 1
- 125000000913 palmityl 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])[H] 0.000 description 1
- 125000002958 pentadecyl 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])[H] 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 230000005588 protonation Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000004366 reverse phase liquid chromatography Methods 0.000 description 1
- 238000006884 silylation reaction Methods 0.000 description 1
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 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 1
- 239000010409 thin film Substances 0.000 description 1
- 125000002889 tridecyl 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])[H] 0.000 description 1
- 238000007039 two-step reaction Methods 0.000 description 1
Images
Classifications
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D15/00—Separating processes involving the treatment of liquids with solid sorbents; Apparatus therefor
- B01D15/08—Selective adsorption, e.g. chromatography
- B01D15/10—Selective adsorption, e.g. chromatography characterised by constructional or operational features
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D15/00—Separating processes involving the treatment of liquids with solid sorbents; Apparatus therefor
- B01D15/08—Selective adsorption, e.g. chromatography
- B01D15/10—Selective adsorption, e.g. chromatography characterised by constructional or operational features
- B01D15/20—Selective adsorption, e.g. chromatography characterised by constructional or operational features relating to the conditioning of the sorbent material
- B01D15/206—Packing or coating
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D15/00—Separating processes involving the treatment of liquids with solid sorbents; Apparatus therefor
- B01D15/08—Selective adsorption, e.g. chromatography
- B01D15/26—Selective adsorption, e.g. chromatography characterised by the separation mechanism
- B01D15/32—Bonded phase chromatography
- B01D15/325—Reversed phase
- B01D15/327—Reversed phase with hydrophobic interaction
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J20/00—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof
- B01J20/22—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof comprising organic material
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J20/00—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof
- B01J20/28—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof characterised by their form or physical properties
- B01J20/28014—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof characterised by their form or physical properties characterised by their form
- B01J20/28028—Particles immobilised within fibres or filaments
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J20/00—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof
- B01J20/28—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof characterised by their form or physical properties
- B01J20/28014—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof characterised by their form or physical properties characterised by their form
- B01J20/28047—Gels
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J20/00—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof
- B01J20/281—Sorbents specially adapted for preparative, analytical or investigative chromatography
- B01J20/286—Phases chemically bonded to a substrate, e.g. to silica or to polymers
- B01J20/287—Non-polar phases; Reversed phases
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J20/00—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof
- B01J20/281—Sorbents specially adapted for preparative, analytical or investigative chromatography
- B01J20/291—Gel sorbents
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J20/00—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof
- B01J20/30—Processes for preparing, regenerating, or reactivating
- B01J20/3092—Packing of a container, e.g. packing a cartridge or column
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J20/00—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof
- B01J20/30—Processes for preparing, regenerating, or reactivating
- B01J20/32—Impregnating or coating ; Solid sorbent compositions obtained from processes involving impregnating or coating
- B01J20/3202—Impregnating or coating ; Solid sorbent compositions obtained from processes involving impregnating or coating characterised by the carrier, support or substrate used for impregnation or coating
- B01J20/3204—Inorganic carriers, supports or substrates
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J20/00—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof
- B01J20/30—Processes for preparing, regenerating, or reactivating
- B01J20/32—Impregnating or coating ; Solid sorbent compositions obtained from processes involving impregnating or coating
- B01J20/3214—Impregnating or coating ; Solid sorbent compositions obtained from processes involving impregnating or coating characterised by the method for obtaining this coating or impregnating
- B01J20/3217—Resulting in a chemical bond between the coating or impregnating layer and the carrier, support or substrate, e.g. a covalent bond
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J20/00—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof
- B01J20/30—Processes for preparing, regenerating, or reactivating
- B01J20/32—Impregnating or coating ; Solid sorbent compositions obtained from processes involving impregnating or coating
- B01J20/3231—Impregnating or coating ; Solid sorbent compositions obtained from processes involving impregnating or coating characterised by the coating or impregnating layer
- B01J20/3242—Layers with a functional group, e.g. an affinity material, a ligand, a reactant or a complexing group
- B01J20/3244—Non-macromolecular compounds
- B01J20/3246—Non-macromolecular compounds having a well defined chemical structure
- 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
- B01J20/3259—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 at least two different types of heteroatoms selected from nitrogen, oxygen or sulfur with at least one silicon atom
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J20/00—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof
- B01J20/30—Processes for preparing, regenerating, or reactivating
- B01J20/32—Impregnating or coating ; Solid sorbent compositions obtained from processes involving impregnating or coating
- B01J20/3291—Characterised by the shape of the carrier, the coating or the obtained coated product
- B01J20/3293—Coatings on a core, the core being particle or fiber shaped, e.g. encapsulated particles, coated fibers
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
- B01J31/0234—Nitrogen-, phosphorus-, arsenic- or antimony-containing compounds
- B01J31/0235—Nitrogen containing compounds
- B01J31/0237—Amines
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/0803—Compounds with Si-C or Si-Si linkages
- C07F7/0805—Compounds with Si-C or Si-Si linkages comprising only Si, C or H atoms
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J2220/00—Aspects relating to sorbent materials
- B01J2220/50—Aspects relating to the use of sorbent or filter aid materials
- B01J2220/52—Sorbents specially adapted for preparative chromatography
Landscapes
- Chemical & Material Sciences (AREA)
- Analytical Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Chemistry (AREA)
- Dispersion Chemistry (AREA)
- Inorganic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Solid-Sorbent Or Filter-Aiding Compositions (AREA)
Description
疎水化すべき親水性材料を、反応促進剤としてアミノ酸存在下で、疎水性基含有シリル化剤と反応させ、前記親水性材料の表面に疎水性基含有シリル基を導入することを含む、親水性材料の疎水化方法である。
疎水化すべき親水性材料を、反応促進剤としてアミノ酸存在下で、疎水性基含有シリル化剤と反応させ、前記親水性材料の表面に疎水性基含有シリル基を導入することを含む。
ここで、Xは、ハロゲン原子又はアルコキシ基を表し、Rは、4-nにより、同一又は異なっていてもよく、置換基を有していてもよい炭化水素基を表す。nは、1、2、又は3を表す。
ジメチルプロピルクロロシラン、プロピルトリクロロシラン、
ジメチルブチルクロロシラン、ブチルトリクロロシラン、
ジメチルヘキシルクロロシラン、ヘキシルトリクロロシラン、
ジメチルオクチルクロロシラン、オクチルトリクロロシラン、
ジメチルデシルクロロシラン、デシルトリクロロシラン、
ジメチルドデシルクロロシラン、ドデシルトリクロロシラン、
ジメチルヘキサデシルクロロシラン、ヘキサデシルトリクロロシラン、
ジメチルオクタデシルクロロシラン、オクタデシルトリクロロシラン、
ジメチルフェニルクロロシラン、及びフェニルトリクロロシランを例示することができる。
反応試剤としての疎水性基含有シリル化剤に対する量としては、0.2nMのシラノール基に対して10倍量(2nM)程度あればよい。
試薬は和光純薬(株)又は東京化成工業(株)製の特級グレード試薬を用いた。
予め、オクタデシルシリル(ODS)化剤としてジメチルオクタデシルクロロシラン(MW:347.09,mp28-31℃,東京化成工業(株)特級グレード試薬)を60℃の乾熱機オーブン中で30分間加温して一部溶解させておいた。
接触角計(協和界面科学株式会社製,DMo-601)を用いて、温度25℃、相対湿度50%の雰囲気中で、得られたODS化Si基板表面の純水の接触角を測定した。接触角は、98.7であった。n=5の平均値。この際の写真を図1、及び図2に示す。
実施例1-1で得られたODS化Si基板表面の0.02(v/v)トリフルオロ酢酸(TFA)による耐加水分解性を確かめた。
[比較例1-1]
オクタデシルクロロシランの添加を行わなかった以外は実施例1-1と同様にして、Si基板表面に対する処理を行った。実施例1-1と同様に接触角を測定した。接触角は、59.5であった。n=5の平均値。この際の写真を図4、及び図5に示す。
次に、比較例1-1で得られたSi基板に対して、実施例1-2と同様に、0.02(v/v)トリフルオロ酢酸(TFA)による耐加水分解性を確かめた。実施例1-2と同様に接触角を測定した。接触角は、55.7であった。n=5の平均値。オクタデシルシリル基の導入は行われておらず、接触角はTFA処理前と同等レベルであった。この際の写真を図6に示す。
疎水化すべき親水性材料を、反応促進剤としてアミノ酸存在下で、疎水性基含有シリル化剤と反応させ、親水性材料表面に疎水性基含有シリル基を導入することを含む、親水性材料の疎水化方法。
前記疎水性基含有シリル化剤は、式(I)
(X)n Si(R)4-n (I)
(ここで、Xは、ハロゲン原子又はアルコキシ基を表し、Rは、同一又は異なっていてもよく、置換基を有していてもよい炭化水素基を表す。nは、1、2、又は3を表す。)
で示される有機ケイ素化合物である、上記(1)に記載の方法。
前記式(I)において、Rが表す炭化水素基は、炭素数1~20の飽和又は不飽和の脂肪族基、又は芳香族基である、上記(2)に記載の方法。
前記一般式(I)において、Xが表すハロゲン原子は、塩素原子である、上記(2)又は(3)に記載の方法。
前記疎水基含有シリル化剤は、トリメチルクロロシラン、
ジメチルプロピルクロロシラン、プロピルトリクロロシラン、
ジメチルブチルクロロシラン、ブチルトリクロロシラン、
ジメチルヘキシルクロロシラン、ヘキシルトリクロロシラン、
ジメチルオクチルクロロシラン、オクチルトリクロロシラン、
ジメチルデシルクロロシラン、デシルトリクロロシラン、
ジメチルドデシルクロロシラン、ドデシルトリクロロシラン、
ジメチルヘキサデシルクロロシラン、ヘキサデシルトリクロロシラン、
ジメチルオクタデシルクロロシラン、オクタデシルトリクロロシラン、
ジメチルフェニルクロロシラン、及びフェニルトリクロロシランからなる群から選ばれる、上記(1)~(4)のいずれかに記載の方法。
前記アミノ酸は、塩基性アミノ酸である、上記(1)~(5)のいずれかに記載の方法。
前記アミノ酸は、アルギニン、リジン、ヒスチジン、トリプトファン、オルニチン、及びこれらアミノ酸の修飾化合物からなる群から選ばれる、上記(1)~(6)のいずれかに記載の方法。
疎水化すべきシリカゲル材料を、反応促進剤としてアミノ酸存在下で、疎水性基含有シリル化剤と反応させ、前記シリカゲルの表面に疎水性基含有シリル基を導入することを含む、疎水化されたシリカゲルカラム充填剤の製造方法。
疎水化すべきシリカゲル材料を、反応促進剤としてアミノ酸存在下で、疎水性基含有シリル化剤と反応させ、前記シリカゲルの表面に疎水性基含有シリル基を導入して、疎水化されたシリカゲルカラム充填剤を得て、
前記疎水化されたシリカゲルカラム充填剤をカラムに充填することを含む、疎水化されたシリカゲルカラムの製造方法。
疎水化すべきSi基板材料を、反応促進剤としてアミノ酸存在下で、疎水性基含有シリル化剤と反応させ、前記Si基板の表面に疎水性基含有シリル基を導入することを含む、疎水化されたSi基板の製造方法。
疎水化すべき中空ファイバー材料を、反応促進剤としてアミノ酸存在下で、疎水性基含有シリル化剤と反応させ、前記ファイバー材料の表面の親水性基に疎水性基含有シリル基を導入することを含む、疎水化された中空ファイバー材料の製造方法。
疎水化すべき中空ファイバー材料を、反応促進剤としてアミノ酸存在下で、疎水性基含有シリル化剤と反応させ、前記ファイバー材料の表面に疎水性基含有シリル基を導入して、疎水化された中空ファイバー材料を得て、
前記疎水化された中空ファイバー材料を用いて、AF4/HF5分離モジュールを製造する方法。
Claims (8)
- 疎水化すべきSi基板材料を、反応促進剤としてアミノ酸存在下で、疎水性基含有シリル化剤と反応させ、前記Si基板材料の表面に疎水性基含有シリル基を導入することを含む、疎水化されたSi基板の製造方法。
- 疎水化すべき中空ファイバー材料を、反応促進剤としてアミノ酸存在下で、疎水性基含有シリル化剤と反応させ、前記中空ファイバー材料の表面の親水性基に疎水性基含有シリル基を導入することを含む、疎水化された中空ファイバー材料の製造方法。
- 疎水化すべき中空ファイバー材料を、反応促進剤としてアミノ酸存在下で、疎水性基含有シリル化剤と反応させ、前記中空ファイバー材料の表面の親水性基に疎水性基含有シリル基を導入して、疎水化された中空ファイバー材料を得て、
前記疎水化された中空ファイバー材料を用いて、AF4/HF5分離モジュールを製造する方法。 - 前記疎水性基含有シリル化剤は、式(I)
(X) n Si(R) 4-n (I)
(ここで、Xは、ハロゲン原子又はアルコキシ基を表し、Rは、同一又は異なっていてもよく、置換基を有していてもよい炭化水素基を表す。nは、1、2、又は3を表す。)
で示される有機ケイ素化合物である、請求項1~3のいずれかに記載の方法。 - 前記式(I)において、Rが表す炭化水素基は、炭素数1~20の飽和又は不飽和の脂肪族基、又は芳香族基である、請求項4に記載の方法。
- 前記式(I)において、Xが表すハロゲン原子は、塩素原子である、請求項4又は5に記載の方法。
- 前記疎水性基含有シリル化剤は、トリメチルクロロシラン、
ジメチルプロピルクロロシラン、プロピルトリクロロシラン、
ジメチルブチルクロロシラン、ブチルトリクロロシラン、
ジメチルヘキシルクロロシラン、ヘキシルトリクロロシラン、
ジメチルオクチルクロロシラン、オクチルトリクロロシラン、
ジメチルデシルクロロシラン、デシルトリクロロシラン、
ジメチルドデシルクロロシラン、ドデシルトリクロロシラン、
ジメチルヘキサデシルクロロシラン、ヘキサデシルトリクロロシラン、
ジメチルオクタデシルクロロシラン、オクタデシルトリクロロシラン、
ジメチルフェニルクロロシラン、及びフェニルトリクロロシランからなる群から選ばれる、請求項1~6のいずれかに記載の方法。 - 前記アミノ酸は、アルギニン、リジン、ヒスチジン、トリプトファン、オルニチン、及びこれらアミノ酸の修飾化合物からなる群から選ばれる、請求項1~7のいずれかに記載の方法。
Priority Applications (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2019074772A JP7156146B2 (ja) | 2019-04-10 | 2019-04-10 | 親水性材料の疎水化方法 |
CN202010058411.1A CN111804007B (zh) | 2019-04-10 | 2020-01-19 | 亲水性材料的疏水化方法 |
US16/811,329 US11090631B2 (en) | 2019-04-10 | 2020-03-06 | Method for hydrophobization of hydrophilic material |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2019074772A JP7156146B2 (ja) | 2019-04-10 | 2019-04-10 | 親水性材料の疎水化方法 |
Publications (2)
Publication Number | Publication Date |
---|---|
JP2020171882A JP2020171882A (ja) | 2020-10-22 |
JP7156146B2 true JP7156146B2 (ja) | 2022-10-19 |
Family
ID=72747645
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2019074772A Active JP7156146B2 (ja) | 2019-04-10 | 2019-04-10 | 親水性材料の疎水化方法 |
Country Status (3)
Country | Link |
---|---|
US (1) | US11090631B2 (ja) |
JP (1) | JP7156146B2 (ja) |
CN (1) | CN111804007B (ja) |
Families Citing this family (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US11709155B2 (en) | 2017-09-18 | 2023-07-25 | Waters Technologies Corporation | Use of vapor deposition coated flow paths for improved chromatography of metal interacting analytes |
US11709156B2 (en) | 2017-09-18 | 2023-07-25 | Waters Technologies Corporation | Use of vapor deposition coated flow paths for improved analytical analysis |
US11918936B2 (en) | 2020-01-17 | 2024-03-05 | Waters Technologies Corporation | Performance and dynamic range for oligonucleotide bioanalysis through reduction of non specific binding |
CN114570328A (zh) * | 2022-03-30 | 2022-06-03 | 大连理工大学盘锦产业技术研究院 | 一种疏水改性分子筛及其制备方法和应用 |
Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2002167212A (ja) | 2000-09-25 | 2002-06-11 | Matsushita Electric Ind Co Ltd | シリカ多孔体の製造方法、それを用いた断熱材 |
JP2003172733A (ja) | 2001-09-27 | 2003-06-20 | Kanto Chem Co Inc | 液体クロマトグラフィー用ods化シリカゲル充填剤の製造方法 |
US20150246339A1 (en) | 2012-09-28 | 2015-09-03 | Consiglio Nazionale Delle Ricerche | Functionalized siliceous filters for sampling and purification of organic compounds |
JP2016534201A (ja) | 2013-08-30 | 2016-11-04 | モーメンティブ・パフォーマンス・マテリアルズ・インク | アミノ酸を含む湿気硬化性化合物 |
Family Cites Families (9)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
SE8802126D0 (sv) * | 1988-06-07 | 1988-06-07 | Pharmacia Ab | Apparatus for flow field flow fractionation |
US20040118762A1 (en) * | 2002-12-18 | 2004-06-24 | Jishou Xu | Packing materials for liquid chromatography using chemically modified diamond powders |
US7125488B2 (en) * | 2004-02-12 | 2006-10-24 | Varian, Inc. | Polar-modified bonded phase materials for chromatographic separations |
JP5173691B2 (ja) * | 2008-09-17 | 2013-04-03 | 株式会社 資生堂 | 親水性相互作用クロマトグラフィー用充填剤 |
CN107754776B (zh) * | 2012-05-15 | 2021-09-21 | 沃特世科技公司 | 色谱材料 |
JP6231263B2 (ja) * | 2012-07-17 | 2017-11-15 | 株式会社島津製作所 | アフィニティ支持体及びそれを用いた物質の捕捉方法 |
CA2889914C (en) * | 2012-11-01 | 2021-09-14 | Santosh RAHANE | Surface modification of porous base supports |
DE102014213428A1 (de) * | 2014-07-10 | 2014-11-27 | Postnova Analytics Gmbh | Vorrichtung für die Feldflussfraktionierung |
US10618920B2 (en) * | 2016-06-03 | 2020-04-14 | Agilent Technologies, Inc. | Functionalized particles having modified phases |
-
2019
- 2019-04-10 JP JP2019074772A patent/JP7156146B2/ja active Active
-
2020
- 2020-01-19 CN CN202010058411.1A patent/CN111804007B/zh active Active
- 2020-03-06 US US16/811,329 patent/US11090631B2/en active Active
Patent Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2002167212A (ja) | 2000-09-25 | 2002-06-11 | Matsushita Electric Ind Co Ltd | シリカ多孔体の製造方法、それを用いた断熱材 |
JP2003172733A (ja) | 2001-09-27 | 2003-06-20 | Kanto Chem Co Inc | 液体クロマトグラフィー用ods化シリカゲル充填剤の製造方法 |
US20150246339A1 (en) | 2012-09-28 | 2015-09-03 | Consiglio Nazionale Delle Ricerche | Functionalized siliceous filters for sampling and purification of organic compounds |
JP2016534201A (ja) | 2013-08-30 | 2016-11-04 | モーメンティブ・パフォーマンス・マテリアルズ・インク | アミノ酸を含む湿気硬化性化合物 |
Non-Patent Citations (1)
Title |
---|
QIAO, X. G. et al.,L-Arginine-Catalyzed Synthesis of Nanometric Organosilica Particles through a Waterborne Sol-Gel Process and Their Porous Structure Analysis,Langmuir,2018年,Vol.34, No.23,p.6784-6796 |
Also Published As
Publication number | Publication date |
---|---|
US20200324272A1 (en) | 2020-10-15 |
JP2020171882A (ja) | 2020-10-22 |
CN111804007B (zh) | 2022-02-25 |
US11090631B2 (en) | 2021-08-17 |
CN111804007A (zh) | 2020-10-23 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
JP7156146B2 (ja) | 親水性材料の疎水化方法 | |
CN101356003B (zh) | 二氧化硅基材料 | |
JP2014065300A (ja) | クロマトグラフィシステムおよび用途に用いるためのポリシラザン熱硬化性ポリマー | |
JP2007523331A (ja) | 有機基を表面から除去した多孔質ハイブリッドモノリス材料 | |
JP2009080128A (ja) | 表面から有機基を取り除いた多孔質混成物粒子 | |
JP4904161B2 (ja) | 基材結合用の極性シラン及び結合された基材のクロマトグラフィーにおける使用 | |
JPWO2006001300A1 (ja) | 高耐久性液体クロマトグラフィー用充填剤 | |
US20050191503A1 (en) | Polycarbosilane treatment of substrates | |
US7033505B2 (en) | Packings for liquid chromatography, process for preparing and usage | |
EP0470255A1 (en) | Chromatographic packing and preparation thereof | |
JP2010052986A (ja) | 表面処理されたシリカ及びその製造方法 | |
US7534352B2 (en) | Reversed endcapping and bonding of chromatographic stationary phases using hydrosilanes | |
US7265236B2 (en) | Polypodal silanes with embedded hydrophilicity | |
JPH04212058A (ja) | 液体クロマトグラフィー用充填剤の製造方法 | |
EP3435079A1 (en) | Chromatography stationary phase | |
US9610576B2 (en) | Hydrolytically stable ion-exchange stationary phases and uses thereof | |
KR101720359B1 (ko) | 충전제의 제조방법, 충전제 및 칼럼 | |
JP5190640B2 (ja) | アルキルスルフィニル基またはアルキルスルホニル基を有するクロマトグラフィー担体及びその製造方法 | |
JPH08304371A (ja) | クロマトグラフィー用充填剤の製造方法 | |
KR101751915B1 (ko) | 내산성이 우수한 고도 엔드캡핑 충전제 제조방법과 이를 이용하여 제조된 충전제 및 충전컬럼 | |
JP5993553B2 (ja) | 充填剤の製造方法 | |
US20090078633A1 (en) | Chromatographic stationary phases | |
Pfrommer et al. | Isoelectronic Zwitterionic Pentacoordinate Silicon Compounds with SiO4 and Si O5 Frameworks | |
JP6199140B2 (ja) | 充填剤の製造方法、充填剤及びカラム | |
Van Meter III | Synthesis and Characterization of Surface-Confined Ionic Liquid Stationary Phases for High Performance Liquid Chromatography |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
A621 | Written request for application examination |
Free format text: JAPANESE INTERMEDIATE CODE: A621 Effective date: 20210804 |
|
A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20220622 |
|
A977 | Report on retrieval |
Free format text: JAPANESE INTERMEDIATE CODE: A971007 Effective date: 20220624 |
|
A601 | Written request for extension of time |
Free format text: JAPANESE INTERMEDIATE CODE: A601 Effective date: 20220808 |
|
A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20220818 |
|
TRDD | Decision of grant or rejection written | ||
A01 | Written decision to grant a patent or to grant a registration (utility model) |
Free format text: JAPANESE INTERMEDIATE CODE: A01 Effective date: 20220906 |
|
A61 | First payment of annual fees (during grant procedure) |
Free format text: JAPANESE INTERMEDIATE CODE: A61 Effective date: 20220919 |
|
R151 | Written notification of patent or utility model registration |
Ref document number: 7156146 Country of ref document: JP Free format text: JAPANESE INTERMEDIATE CODE: R151 |