JPH0475216B2 - - Google Patents

Info

Publication number: JPH0475216B2
Authority: JP; Japan
Prior art keywords: cellulose; formula; ethanol; polysaccharide; separation
Prior art date: 1984-04-05
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.): Expired - Lifetime

Application number

JP59068088A

Other languages

English (en)

Japanese (ja)

Other versions

JPS60214748A (ja

Priority date (The priority date 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 date listed.)

1984-04-05

Filing date

1984-04-05

Publication date

1992-11-30

1984-04-05 Application filed filed Critical

1984-04-05 Priority to JP59068088A priority Critical patent/JPS60214748A/ja

1984-12-20 Priority to EP84115960A priority patent/EP0147804B2/fr

1984-12-20 Priority to DE8484115960T priority patent/DE3483311D1/de

1985-10-28 Publication of JPS60214748A publication Critical patent/JPS60214748A/ja

1992-11-30 Publication of JPH0475216B2 publication Critical patent/JPH0475216B2/ja

Status Granted legal-status Critical Current

Links

239000003795 chemical substances by application Substances 0.000 claims description 32
229920002678 cellulose Polymers 0.000 claims description 26
239000001913 cellulose Substances 0.000 claims description 26
238000000926 separation method Methods 0.000 claims description 19
125000001072 heteroaryl group Chemical group 0.000 claims description 9
239000004480 active ingredient Substances 0.000 claims description 4
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 42
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 33
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 17
230000015572 biosynthetic process Effects 0.000 description 17
229920001282 polysaccharide Polymers 0.000 description 17
239000005017 polysaccharide Substances 0.000 description 17
238000003786 synthesis reaction Methods 0.000 description 17
150000004804 polysaccharides Chemical class 0.000 description 16
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
238000000034 method Methods 0.000 description 15
230000003287 optical effect Effects 0.000 description 14
239000002904 solvent Substances 0.000 description 13
239000011521 glass Substances 0.000 description 12
239000000126 substance Substances 0.000 description 11
150000001875 compounds Chemical class 0.000 description 10
239000000047 product Substances 0.000 description 9
239000011324 bead Substances 0.000 description 8
239000000203 mixture Substances 0.000 description 8
239000000377 silicon dioxide Substances 0.000 description 8
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical class CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 7
VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 6
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
238000010521 absorption reaction Methods 0.000 description 6
239000007788 liquid Substances 0.000 description 5
229920002284 Cellulose triacetate Polymers 0.000 description 4
229920001503 Glucan Polymers 0.000 description 4
NNLVGZFZQQXQNW-ADJNRHBOSA-N [(2r,3r,4s,5r,6s)-4,5-diacetyloxy-3-[(2s,3r,4s,5r,6r)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxy-6-[(2r,3r,4s,5r,6s)-4,5,6-triacetyloxy-2-(acetyloxymethyl)oxan-3-yl]oxyoxan-2-yl]methyl acetate Chemical compound O([C@@H]1O[C@@H]([C@H]([C@H](OC(C)=O)[C@H]1OC(C)=O)O[C@H]1[C@@H]([C@@H](OC(C)=O)[C@H](OC(C)=O)[C@@H](COC(C)=O)O1)OC(C)=O)COC(=O)C)[C@@H]1[C@@H](COC(C)=O)O[C@@H](OC(C)=O)[C@H](OC(C)=O)[C@H]1OC(C)=O NNLVGZFZQQXQNW-ADJNRHBOSA-N 0.000 description 4
238000006243 chemical reaction Methods 0.000 description 4
238000004587 chromatography analysis Methods 0.000 description 4
125000002887 hydroxy group Chemical class [H]O* 0.000 description 4
238000006116 polymerization reaction Methods 0.000 description 4
239000000843 powder Substances 0.000 description 4
238000003756 stirring Methods 0.000 description 4
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
229920000856 Amylose Polymers 0.000 description 3
229920001661 Chitosan Polymers 0.000 description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 3
YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical group C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 3
238000001816 cooling Methods 0.000 description 3
230000000694 effects Effects 0.000 description 3
150000002148 esters Chemical class 0.000 description 3
-1 etc.) Polymers 0.000 description 3
238000001914 filtration Methods 0.000 description 3
238000004811 liquid chromatography Methods 0.000 description 3
239000002245 particle Substances 0.000 description 3
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
235000002639 sodium chloride Nutrition 0.000 description 3
239000011780 sodium chloride Substances 0.000 description 3
229910052717 sulfur Inorganic materials 0.000 description 3
239000011593 sulfur Substances 0.000 description 3
QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 3
238000004809 thin layer chromatography Methods 0.000 description 3
238000001291 vacuum drying Methods 0.000 description 3
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
229920001221 xylan Polymers 0.000 description 3
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
229920002498 Beta-glucan Polymers 0.000 description 2
229920002101 Chitin Polymers 0.000 description 2
229920002558 Curdlan Polymers 0.000 description 2
239000001879 Curdlan Substances 0.000 description 2
229920002670 Fructan Polymers 0.000 description 2
OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 2
229920001202 Inulin Polymers 0.000 description 2
CPLXHLVBOLITMK-UHFFFAOYSA-N Magnesium oxide Chemical compound [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 2
PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-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
238000000862 absorption spectrum Methods 0.000 description 2
239000002253 acid Substances 0.000 description 2
125000002252 acyl group Chemical group 0.000 description 2
125000003277 amino group Chemical group 0.000 description 2
ISAOCJYIOMOJEB-UHFFFAOYSA-N benzoin Chemical compound C=1C=CC=CC=1C(O)C(=O)C1=CC=CC=C1 ISAOCJYIOMOJEB-UHFFFAOYSA-N 0.000 description 2
WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 2
WQZGKKKJIJFFOK-RWOPYEJCSA-N beta-D-mannose Chemical compound OC[C@H]1O[C@@H](O)[C@@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-RWOPYEJCSA-N 0.000 description 2
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 2
150000001732 carboxylic acid derivatives Chemical class 0.000 description 2
239000000969 carrier Substances 0.000 description 2
239000007795 chemical reaction product Substances 0.000 description 2
239000007810 chemical reaction solvent Substances 0.000 description 2
235000019316 curdlan Nutrition 0.000 description 2
229940078035 curdlan Drugs 0.000 description 2
239000003814 drug Substances 0.000 description 2
238000001035 drying Methods 0.000 description 2
238000005886 esterification reaction Methods 0.000 description 2
238000010438 heat treatment Methods 0.000 description 2
238000002329 infrared spectrum Methods 0.000 description 2
JYJIGFIDKWBXDU-MNNPPOADSA-N inulin Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)OC[C@]1(OC[C@]2(OC[C@]3(OC[C@]4(OC[C@]5(OC[C@]6(OC[C@]7(OC[C@]8(OC[C@]9(OC[C@]%10(OC[C@]%11(OC[C@]%12(OC[C@]%13(OC[C@]%14(OC[C@]%15(OC[C@]%16(OC[C@]%17(OC[C@]%18(OC[C@]%19(OC[C@]%20(OC[C@]%21(OC[C@]%22(OC[C@]%23(OC[C@]%24(OC[C@]%25(OC[C@]%26(OC[C@]%27(OC[C@]%28(OC[C@]%29(OC[C@]%30(OC[C@]%31(OC[C@]%32(OC[C@]%33(OC[C@]%34(OC[C@]%35(OC[C@]%36(O[C@@H]%37[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O%37)O)[C@H]([C@H](O)[C@@H](CO)O%36)O)[C@H]([C@H](O)[C@@H](CO)O%35)O)[C@H]([C@H](O)[C@@H](CO)O%34)O)[C@H]([C@H](O)[C@@H](CO)O%33)O)[C@H]([C@H](O)[C@@H](CO)O%32)O)[C@H]([C@H](O)[C@@H](CO)O%31)O)[C@H]([C@H](O)[C@@H](CO)O%30)O)[C@H]([C@H](O)[C@@H](CO)O%29)O)[C@H]([C@H](O)[C@@H](CO)O%28)O)[C@H]([C@H](O)[C@@H](CO)O%27)O)[C@H]([C@H](O)[C@@H](CO)O%26)O)[C@H]([C@H](O)[C@@H](CO)O%25)O)[C@H]([C@H](O)[C@@H](CO)O%24)O)[C@H]([C@H](O)[C@@H](CO)O%23)O)[C@H]([C@H](O)[C@@H](CO)O%22)O)[C@H]([C@H](O)[C@@H](CO)O%21)O)[C@H]([C@H](O)[C@@H](CO)O%20)O)[C@H]([C@H](O)[C@@H](CO)O%19)O)[C@H]([C@H](O)[C@@H](CO)O%18)O)[C@H]([C@H](O)[C@@H](CO)O%17)O)[C@H]([C@H](O)[C@@H](CO)O%16)O)[C@H]([C@H](O)[C@@H](CO)O%15)O)[C@H]([C@H](O)[C@@H](CO)O%14)O)[C@H]([C@H](O)[C@@H](CO)O%13)O)[C@H]([C@H](O)[C@@H](CO)O%12)O)[C@H]([C@H](O)[C@@H](CO)O%11)O)[C@H]([C@H](O)[C@@H](CO)O%10)O)[C@H]([C@H](O)[C@@H](CO)O9)O)[C@H]([C@H](O)[C@@H](CO)O8)O)[C@H]([C@H](O)[C@@H](CO)O7)O)[C@H]([C@H](O)[C@@H](CO)O6)O)[C@H]([C@H](O)[C@@H](CO)O5)O)[C@H]([C@H](O)[C@@H](CO)O4)O)[C@H]([C@H](O)[C@@H](CO)O3)O)[C@H]([C@H](O)[C@@H](CO)O2)O)[C@@H](O)[C@H](O)[C@@H](CO)O1 JYJIGFIDKWBXDU-MNNPPOADSA-N 0.000 description 2
229940029339 inulin Drugs 0.000 description 2
230000014759 maintenance of location Effects 0.000 description 2
239000000463 material Substances 0.000 description 2
239000012528 membrane Substances 0.000 description 2
235000001968 nicotinic acid Nutrition 0.000 description 2
239000011664 nicotinic acid Substances 0.000 description 2
238000000053 physical method Methods 0.000 description 2
230000000717 retained effect Effects 0.000 description 2
238000006467 substitution reaction Methods 0.000 description 2
238000004381 surface treatment Methods 0.000 description 2
238000005406 washing Methods 0.000 description 2
WDQLRUYAYXDIFW-RWKIJVEZSA-N (2r,3r,4s,5r,6r)-4-[(2s,3r,4s,5r,6r)-3,5-dihydroxy-4-[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-6-[[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]oxan-2-yl]oxy-6-(hydroxymethyl)oxane-2,3,5-triol Chemical compound O[C@@H]1[C@@H](CO)O[C@@H](O)[C@H](O)[C@H]1O[C@H]1[C@H](O)[C@@H](O[C@H]2[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O2)O)[C@H](O)[C@@H](CO[C@H]2[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O2)O)O1 WDQLRUYAYXDIFW-RWKIJVEZSA-N 0.000 description 1
MDQHTWMXYBVSHU-UHFFFAOYSA-N 2-trimethylsilylacetamide Chemical compound C[Si](C)(C)CC(N)=O MDQHTWMXYBVSHU-UHFFFAOYSA-N 0.000 description 1
ZDHKVKPZQKYREU-UHFFFAOYSA-N 4-(chloromethyl)pyridine;hydron;chloride Chemical compound Cl.ClCC1=CC=NC=C1 ZDHKVKPZQKYREU-UHFFFAOYSA-N 0.000 description 1
229920000936 Agarose Polymers 0.000 description 1
239000005995 Aluminium silicate Substances 0.000 description 1
229920000945 Amylopectin Polymers 0.000 description 1
229920002307 Dextran Polymers 0.000 description 1
229920000057 Mannan Polymers 0.000 description 1
RJUFJBKOKNCXHH-UHFFFAOYSA-N Methyl propionate Chemical compound CCC(=O)OC RJUFJBKOKNCXHH-UHFFFAOYSA-N 0.000 description 1
239000004793 Polystyrene Substances 0.000 description 1
ARCJQKUWGAZPFX-KBPBESRZSA-N S-trans-stilbene oxide Chemical compound C1([C@H]2[C@@H](O2)C=2C=CC=CC=2)=CC=CC=C1 ARCJQKUWGAZPFX-KBPBESRZSA-N 0.000 description 1
229920002305 Schizophyllan Polymers 0.000 description 1
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
244000028419 Styrax benzoin Species 0.000 description 1
235000000126 Styrax benzoin Nutrition 0.000 description 1
235000008411 Sumatra benzointree Nutrition 0.000 description 1
GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 1
239000003905 agrochemical Substances 0.000 description 1
239000000783 alginic acid Substances 0.000 description 1
229920000615 alginic acid Polymers 0.000 description 1
235000010443 alginic acid Nutrition 0.000 description 1
229960001126 alginic acid Drugs 0.000 description 1
150000004781 alginic acids Chemical class 0.000 description 1
125000000217 alkyl group Chemical group 0.000 description 1
PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
235000012211 aluminium silicate Nutrition 0.000 description 1
238000004458 analytical method Methods 0.000 description 1
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
238000005452 bending Methods 0.000 description 1
229960002130 benzoin Drugs 0.000 description 1
239000011230 binding agent Substances 0.000 description 1
125000004432 carbon atom Chemical group C* 0.000 description 1
KXDHJXZQYSOELW-UHFFFAOYSA-N carbonic acid monoamide Natural products NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 description 1
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
125000003178 carboxy group Chemical class [H]OC(*)=O 0.000 description 1
150000001244 carboxylic acid anhydrides Chemical class 0.000 description 1
150000001733 carboxylic acid esters Chemical class 0.000 description 1
150000001735 carboxylic acids Chemical class 0.000 description 1
239000003054 catalyst Substances 0.000 description 1
150000001805 chlorine compounds Chemical class 0.000 description 1
239000011248 coating agent Substances 0.000 description 1
238000000576 coating method Methods 0.000 description 1
238000004132 cross linking Methods 0.000 description 1
238000002425 crystallisation Methods 0.000 description 1
125000004093 cyano group Chemical class *C#N 0.000 description 1
239000012024 dehydrating agents‎ Substances 0.000 description 1
AHUXYBVKTIBBJW-UHFFFAOYSA-N dimethoxy(diphenyl)silane Chemical compound C=1C=CC=CC=1[Si](OC)(OC)C1=CC=CC=C1 AHUXYBVKTIBBJW-UHFFFAOYSA-N 0.000 description 1
229940079593 drug Drugs 0.000 description 1
238000000921 elemental analysis Methods 0.000 description 1
239000003480 eluent Substances 0.000 description 1
230000032050 esterification Effects 0.000 description 1
239000000835 fiber Substances 0.000 description 1
238000011049 filling Methods 0.000 description 1
238000004108 freeze drying Methods 0.000 description 1
125000000524 functional group Chemical group 0.000 description 1
150000002243 furanoses Chemical group 0.000 description 1
238000004817 gas chromatography Methods 0.000 description 1
235000019382 gum benzoic Nutrition 0.000 description 1
150000004820 halides Chemical class 0.000 description 1
229910052736 halogen Inorganic materials 0.000 description 1
150000002367 halogens Chemical class 0.000 description 1
125000005842 heteroatom Chemical group 0.000 description 1
MSYBLBLAMDYKKZ-UHFFFAOYSA-N hydron;pyridine-3-carbonyl chloride;chloride Chemical compound Cl.ClC(=O)C1=CC=CN=C1 MSYBLBLAMDYKKZ-UHFFFAOYSA-N 0.000 description 1
TWBYWOBDOCUKOW-UHFFFAOYSA-M isonicotinate Chemical compound [O-]C(=O)C1=CC=NC=C1 TWBYWOBDOCUKOW-UHFFFAOYSA-M 0.000 description 1
NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
AIHDCSAXVMAMJH-GFBKWZILSA-N levan Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)OC[C@@H]1[C@@H](O)[C@H](O)[C@](CO)(CO[C@@H]2[C@H]([C@H](O)[C@@](O)(CO)O2)O)O1 AIHDCSAXVMAMJH-GFBKWZILSA-N 0.000 description 1
UEGPKNKPLBYCNK-UHFFFAOYSA-L magnesium acetate Chemical compound [Mg+2].CC([O-])=O.CC([O-])=O UEGPKNKPLBYCNK-UHFFFAOYSA-L 0.000 description 1
239000011654 magnesium acetate Substances 0.000 description 1
235000011285 magnesium acetate Nutrition 0.000 description 1
229940069446 magnesium acetate Drugs 0.000 description 1
239000000395 magnesium oxide Substances 0.000 description 1
229940017219 methyl propionate Drugs 0.000 description 1
125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
239000012046 mixed solvent Substances 0.000 description 1
PSHKMPUSSFXUIA-UHFFFAOYSA-N n,n-dimethylpyridin-2-amine Chemical compound CN(C)C1=CC=CC=N1 PSHKMPUSSFXUIA-UHFFFAOYSA-N 0.000 description 1
229920005615 natural polymer Polymers 0.000 description 1
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
229910052760 oxygen Inorganic materials 0.000 description 1
239000001301 oxygen Substances 0.000 description 1
125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
229920005640 poly alpha-1,3-glucan Polymers 0.000 description 1
229920002401 polyacrylamide Polymers 0.000 description 1
229920000058 polyacrylate Polymers 0.000 description 1
229920002223 polystyrene Polymers 0.000 description 1
239000011148 porous material Substances 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
238000001556 precipitation Methods 0.000 description 1
238000002360 preparation method Methods 0.000 description 1
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 1
150000003214 pyranose derivatives Chemical class 0.000 description 1
150000003222 pyridines Chemical class 0.000 description 1
239000002994 raw material Substances 0.000 description 1
230000009257 reactivity Effects 0.000 description 1
229910000077 silane Inorganic materials 0.000 description 1
238000002444 silanisation Methods 0.000 description 1
239000000741 silica gel Substances 0.000 description 1
229910002027 silica gel Inorganic materials 0.000 description 1
150000004760 silicates Chemical class 0.000 description 1
238000007613 slurry method Methods 0.000 description 1
238000001179 sorption measurement Methods 0.000 description 1
238000009987 spinning Methods 0.000 description 1
229910001220 stainless steel Inorganic materials 0.000 description 1
239000010935 stainless steel Substances 0.000 description 1
125000000547 substituted alkyl group Chemical group 0.000 description 1
239000000725 suspension Substances 0.000 description 1
230000008961 swelling Effects 0.000 description 1
238000001308 synthesis method Methods 0.000 description 1
QIQITDHWZYEEPA-UHFFFAOYSA-N thiophene-2-carbonyl chloride Chemical compound ClC(=O)C1=CC=CS1 QIQITDHWZYEEPA-UHFFFAOYSA-N 0.000 description 1
QERYCTSHXKAMIS-UHFFFAOYSA-M thiophene-2-carboxylate Chemical compound [O-]C(=O)C1=CC=CS1 QERYCTSHXKAMIS-UHFFFAOYSA-M 0.000 description 1
150000003577 thiophenes Chemical class 0.000 description 1
KJAMZCVTJDTESW-UHFFFAOYSA-N tiracizine Chemical compound C1CC2=CC=CC=C2N(C(=O)CN(C)C)C2=CC(NC(=O)OCC)=CC=C21 KJAMZCVTJDTESW-UHFFFAOYSA-N 0.000 description 1
OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
238000000214 vapour pressure osmometry Methods 0.000 description 1

Landscapes

Solid-Sorbent Or Filter-Aiding Compositions (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Treatment Of Liquids With Adsorbents In General (AREA)

JP59068088A 1983-12-28 1984-04-05 多糖のヘテロ芳香族誘導体より成る分離剤 Granted JPS60214748A (ja)

Priority Applications (3)

Application Number	Priority Date	Filing Date	Title
JP59068088A JPS60214748A (ja)	1984-04-05	1984-04-05	多糖のヘテロ芳香族誘導体より成る分離剤
EP84115960A EP0147804B2 (fr)	1983-12-28	1984-12-20	Procédé de séparation de isomères optiques et de isomères géometriques
DE8484115960T DE3483311D1 (de)	1983-12-28	1984-12-20	Verfahren zur trennung optischer und geometrischer isomere.

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
JP59068088A JPS60214748A (ja)	1984-04-05	1984-04-05	多糖のヘテロ芳香族誘導体より成る分離剤

Publications (2)

Publication Number	Publication Date
JPS60214748A JPS60214748A (ja)	1985-10-28
JPH0475216B2 true JPH0475216B2 (fr)	1992-11-30

Family

ID=13363629

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
JP59068088A Granted JPS60214748A (ja)	1983-12-28	1984-04-05	多糖のヘテロ芳香族誘導体より成る分離剤

Country Status (1)

Country	Link
JP (1)	JPS60214748A (fr)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US5066793A (en) *	1987-10-26	1991-11-19	Ciba-Geigy Corporation	Finely particulate cellulose esters of aromatic or aromatic-aliphatic carboxylic acids, process for their preparation, and the use thereof

Citations (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPS5959365A (ja) *	1982-09-28	1984-04-05	株式会社東芝	マスタスレ−ブ形マニピユレ−タの手首機構
JPS5962661A (ja) *	1982-09-30	1984-04-10	Nitto Electric Ind Co Ltd	感光性樹脂組成物
JPS5965322A (ja) *	1982-10-07	1984-04-13	Ricoh Co Ltd	ヒ−タ制御装置
JPS5968087A (ja) *	1982-10-09	1984-04-17	角野　博光	ホツパ−型コイン類払出し装置
JPS5968089A (ja) *	1982-10-12	1984-04-17	オムロン株式会社	入金装置

1984
- 1984-04-05 JP JP59068088A patent/JPS60214748A/ja active Granted

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPS5959365A (ja) *	1982-09-28	1984-04-05	株式会社東芝	マスタスレ−ブ形マニピユレ−タの手首機構
JPS5962661A (ja) *	1982-09-30	1984-04-10	Nitto Electric Ind Co Ltd	感光性樹脂組成物
JPS5965322A (ja) *	1982-10-07	1984-04-13	Ricoh Co Ltd	ヒ−タ制御装置
JPS5968087A (ja) *	1982-10-09	1984-04-17	角野　博光	ホツパ−型コイン類払出し装置
JPS5968089A (ja) *	1982-10-12	1984-04-17	オムロン株式会社	入金装置

Also Published As

Publication number	Publication date
JPS60214748A (ja)	1985-10-28

Publication	Publication Date	Title
US4786415A (en)	1988-11-22	Separation agent comprising aliphatic ester of polysaccharide
EP0156382B1 (fr)	1990-10-24	Agent de séparation contenant un polysaccharide ayant des substituants acyle ou carbamoyle
JPH0475214B2 (fr)	1992-11-30
JPH0813844B2 (ja)	1996-02-14	多糖のアルキル置換フエニルカルバメ−ト誘導体
JP2004167343A (ja)	2004-06-17	光学異性体用分離剤
EP0147804B2 (fr)	2001-01-03	Procédé de séparation de isomères optiques et de isomères géometriques
US5032277A (en)	1991-07-16	Optical resolution with β-1,4-mannan tribenzoate
EP0150849B1 (fr)	1990-10-31	Agent de séparation
JPWO2002070123A1 (ja)	2004-07-02	光学異性体用分離剤
JPH0442371B2 (fr)	1992-07-13
EP0157364B1 (fr)	1990-09-19	Agent de séparation renfermant les esters alphatiques ou aromatiques de polysaccharide
US5772876A (en)	1998-06-30	Separating agent
JPH0475216B2 (fr)	1992-11-30
JPH0475893B2 (fr)	1992-12-02
JP4293792B2 (ja)	2009-07-08	多環式構造を有する多糖誘導体よりなる分離剤
US5135653A (en)	1992-08-04	Optical resolution with β-1,4-xylan dibenzoate
JPH01203402A (ja)	1989-08-16	多糖類カルバメート誘導体
US5192444A (en)	1993-03-09	Separating with an agent comprising an aliphatic ester of a polysaccharide
JP3746315B2 (ja)	2006-02-15	分離剤
JPH0425061B2 (fr)	1992-04-28
JPH10185894A (ja)	1998-07-14	高速液体クロマトグラフィ−用充填剤の製造法
JPH02289601A (ja)	1990-11-29	新規な多糖誘導体及び分離剤
JPH11255671A (ja)	1999-09-21	光学異性体のクロマト分離法
US5268098A (en)	1993-12-07	Separation agent comprising aliphatic or aromatic ester of polysaccharide
JPS60214749A (ja)	1985-10-28	多糖の置換芳香族エステル誘導体より成る分離剤