FI116840B - Fotokemiallisesti ristisidottuja polysakkaridijohdannaisia alustoina enantiomeerien kromatografiselle erotukselle - Google Patents
Fotokemiallisesti ristisidottuja polysakkaridijohdannaisia alustoina enantiomeerien kromatografiselle erotukselle Download PDFInfo
- Publication number
- FI116840B FI116840B FI973149A FI973149A FI116840B FI 116840 B FI116840 B FI 116840B FI 973149 A FI973149 A FI 973149A FI 973149 A FI973149 A FI 973149A FI 116840 B FI116840 B FI 116840B
- Authority
- FI
- Finland
- Prior art keywords
- cellulose
- groups
- unsubstituted
- formula
- polysaccharide
- Prior art date
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- 229920001282 polysaccharide Polymers 0.000 title claims abstract description 25
- 239000005017 polysaccharide Substances 0.000 title claims abstract description 25
- 150000004676 glycans Chemical class 0.000 title claims description 6
- 238000013375 chromatographic separation Methods 0.000 title abstract description 5
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 title abstract description 4
- 238000002360 preparation method Methods 0.000 claims abstract description 17
- 150000001875 compounds Chemical class 0.000 claims abstract description 15
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 15
- 238000000034 method Methods 0.000 claims abstract description 15
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 claims abstract description 9
- 230000008569 process Effects 0.000 claims abstract description 8
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims abstract description 7
- 125000003107 substituted aryl group Chemical group 0.000 claims abstract 4
- 229920002678 cellulose Polymers 0.000 claims description 38
- 239000001913 cellulose Substances 0.000 claims description 38
- -1 polysaccharide compound Chemical class 0.000 claims description 25
- 238000006243 chemical reaction Methods 0.000 claims description 21
- 239000000463 material Substances 0.000 claims description 19
- 239000011248 coating agent Substances 0.000 claims description 18
- 238000000576 coating method Methods 0.000 claims description 18
- 239000012948 isocyanate Substances 0.000 claims description 17
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 16
- 150000002513 isocyanates Chemical class 0.000 claims description 14
- 239000000725 suspension Substances 0.000 claims description 14
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 13
- 238000004132 cross linking Methods 0.000 claims description 13
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 10
- 229920000856 Amylose Polymers 0.000 claims description 9
- 239000003054 catalyst Substances 0.000 claims description 7
- 239000000741 silica gel Substances 0.000 claims description 5
- 229910002027 silica gel Inorganic materials 0.000 claims description 5
- 229920000742 Cotton Polymers 0.000 claims description 4
- MCMNRKCIXSYSNV-UHFFFAOYSA-N Zirconium dioxide Chemical compound O=[Zr]=O MCMNRKCIXSYSNV-UHFFFAOYSA-N 0.000 claims description 3
- UKLDJPRMSDWDSL-UHFFFAOYSA-L [dibutyl(dodecanoyloxy)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC UKLDJPRMSDWDSL-UHFFFAOYSA-L 0.000 claims description 3
- 239000012975 dibutyltin dilaurate Substances 0.000 claims description 3
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 claims description 3
- 229910052753 mercury Inorganic materials 0.000 claims description 3
- 239000000758 substrate Substances 0.000 claims description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 2
- 239000002841 Lewis acid Substances 0.000 claims description 2
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 claims description 2
- 150000001720 carbohydrates Chemical class 0.000 claims description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- 229910002804 graphite Inorganic materials 0.000 claims description 2
- 239000010439 graphite Substances 0.000 claims description 2
- 239000012442 inert solvent Substances 0.000 claims description 2
- 150000007517 lewis acids Chemical class 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- NPPQSCRMBWNHMW-UHFFFAOYSA-N Meprobamate Chemical compound NC(=O)OCC(C)(CCC)COC(N)=O NPPQSCRMBWNHMW-UHFFFAOYSA-N 0.000 claims 1
- 239000002253 acid Substances 0.000 claims 1
- 150000001266 acyl halides Chemical class 0.000 claims 1
- 229940037003 alum Drugs 0.000 claims 1
- 230000015572 biosynthetic process Effects 0.000 claims 1
- 150000001719 carbohydrate derivatives Chemical class 0.000 claims 1
- 229920001971 elastomer Polymers 0.000 claims 1
- 239000000806 elastomer Substances 0.000 claims 1
- 239000000839 emulsion Substances 0.000 claims 1
- 230000001678 irradiating effect Effects 0.000 claims 1
- 125000000217 alkyl group Chemical group 0.000 abstract description 6
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 abstract description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 81
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 60
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 40
- 239000000243 solution Substances 0.000 description 36
- 239000000047 product Substances 0.000 description 35
- 239000000543 intermediate Substances 0.000 description 34
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 32
- 238000000921 elemental analysis Methods 0.000 description 25
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 24
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 24
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 19
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 16
- 239000007790 solid phase Substances 0.000 description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 15
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 14
- 229910052757 nitrogen Inorganic materials 0.000 description 11
- 150000004804 polysaccharides Chemical class 0.000 description 11
- PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 description 10
- 238000001816 cooling Methods 0.000 description 10
- 239000000203 mixture Substances 0.000 description 10
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- 239000007787 solid Substances 0.000 description 7
- 238000005160 1H NMR spectroscopy Methods 0.000 description 6
- KNHJIEOCVVIBIV-UHFFFAOYSA-N 2,3-dimethylphenyl isocyanate Chemical compound CC1=CC=CC(N=C=O)=C1C KNHJIEOCVVIBIV-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- 239000000460 chlorine Substances 0.000 description 6
- 238000002844 melting Methods 0.000 description 6
- 230000008018 melting Effects 0.000 description 6
- 239000012071 phase Substances 0.000 description 6
- 239000002244 precipitate Substances 0.000 description 6
- 239000000126 substance Substances 0.000 description 6
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 6
- PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical class ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 5
- 239000000706 filtrate Substances 0.000 description 5
- 239000000377 silicon dioxide Substances 0.000 description 5
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 4
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 4
- 229910000831 Steel Inorganic materials 0.000 description 4
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 4
- 239000007789 gas Substances 0.000 description 4
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 4
- 239000002002 slurry Substances 0.000 description 4
- 239000010959 steel 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
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- 238000005481 NMR spectroscopy Methods 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 230000032050 esterification Effects 0.000 description 3
- 238000005886 esterification reaction Methods 0.000 description 3
- 238000012856 packing Methods 0.000 description 3
- 229920000642 polymer Polymers 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 238000006277 sulfonation reaction Methods 0.000 description 3
- 238000010626 work up procedure Methods 0.000 description 3
- GPZXFICWCMCQPF-UHFFFAOYSA-N 2-methylbenzoyl chloride Chemical compound CC1=CC=CC=C1C(Cl)=O GPZXFICWCMCQPF-UHFFFAOYSA-N 0.000 description 2
- ZTWMBHJPUJJJME-UHFFFAOYSA-N 3,4-dimethylpyrrole-2,5-dione Chemical compound CC1=C(C)C(=O)NC1=O ZTWMBHJPUJJJME-UHFFFAOYSA-N 0.000 description 2
- UZFMOKQJFYMBGY-UHFFFAOYSA-N 4-hydroxy-TEMPO Chemical compound CC1(C)CC(O)CC(C)(C)N1[O] UZFMOKQJFYMBGY-UHFFFAOYSA-N 0.000 description 2
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 2
- 239000007983 Tris buffer Substances 0.000 description 2
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 2
- 239000012346 acetyl chloride Substances 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- 235000010233 benzoic acid Nutrition 0.000 description 2
- HTZCNXWZYVXIMZ-UHFFFAOYSA-M benzyl(triethyl)azanium;chloride Chemical compound [Cl-].CC[N+](CC)(CC)CC1=CC=CC=C1 HTZCNXWZYVXIMZ-UHFFFAOYSA-M 0.000 description 2
- 235000014121 butter Nutrition 0.000 description 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 238000004587 chromatography analysis Methods 0.000 description 2
- 239000012141 concentrate Substances 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 239000004744 fabric Substances 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- 229910052740 iodine Inorganic materials 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- 230000001681 protective effect Effects 0.000 description 2
- 238000010926 purge Methods 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 125000000446 sulfanediyl group Chemical group *S* 0.000 description 2
- OMJLGCDQPXRIHT-UHFFFAOYSA-N (3,5-dichlorophenyl)carbamic acid Chemical group OC(=O)NC1=CC(Cl)=CC(Cl)=C1 OMJLGCDQPXRIHT-UHFFFAOYSA-N 0.000 description 1
- KPCOLEDDUNYSQA-UHFFFAOYSA-N (3,5-dimethylphenyl)carbamic acid Chemical class CC1=CC(C)=CC(NC(O)=O)=C1 KPCOLEDDUNYSQA-UHFFFAOYSA-N 0.000 description 1
- MJTFENDZXOFBLA-UHFFFAOYSA-N 1,2,3-tritert-butylbenzene Chemical compound CC(C)(C)C1=CC=CC(C(C)(C)C)=C1C(C)(C)C MJTFENDZXOFBLA-UHFFFAOYSA-N 0.000 description 1
- DZSGDHNHQAJZCO-UHFFFAOYSA-N 1-isocyanato-3,5-dimethylbenzene Chemical compound CC1=CC(C)=CC(N=C=O)=C1 DZSGDHNHQAJZCO-UHFFFAOYSA-N 0.000 description 1
- OQURWGJAWSLGQG-UHFFFAOYSA-N 1-isocyanatopropane Chemical compound CCCN=C=O OQURWGJAWSLGQG-UHFFFAOYSA-N 0.000 description 1
- MFGALGYVFGDXIX-UHFFFAOYSA-N 2,3-Dimethylmaleic anhydride Chemical compound CC1=C(C)C(=O)OC1=O MFGALGYVFGDXIX-UHFFFAOYSA-N 0.000 description 1
- 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 1
- LUQAGMIGBHEUCY-UHFFFAOYSA-N 2-(3,4-dimethyl-2,5-dioxopyrrol-1-yl)acetyl chloride Chemical compound CC1=C(C)C(=O)N(CC(Cl)=O)C1=O LUQAGMIGBHEUCY-UHFFFAOYSA-N 0.000 description 1
- ATNLSPQDFUMNHX-UHFFFAOYSA-N 2-(3,4-dimethyl-2,5-dioxopyrrol-1-yl)benzoyl chloride Chemical compound O=C1C(C)=C(C)C(=O)N1C1=CC=CC=C1C(Cl)=O ATNLSPQDFUMNHX-UHFFFAOYSA-N 0.000 description 1
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
- UPMLOUAZCHDJJD-UHFFFAOYSA-N 4,4'-Diphenylmethane Diisocyanate Chemical compound C1=CC(N=C=O)=CC=C1CC1=CC=C(N=C=O)C=C1 UPMLOUAZCHDJJD-UHFFFAOYSA-N 0.000 description 1
- FVWQRMGTWWXIJK-UHFFFAOYSA-N 4-(3,4-dimethyl-2,5-dioxopyrrol-1-yl)benzoyl chloride Chemical compound O=C1C(C)=C(C)C(=O)N1C1=CC=C(C(Cl)=O)C=C1 FVWQRMGTWWXIJK-UHFFFAOYSA-N 0.000 description 1
- UDCDMLRZYLNYGK-UHFFFAOYSA-N 4-[(3,4-dimethyl-2,5-dioxopyrrol-1-yl)methyl]benzoic acid Chemical compound O=C1C(C)=C(C)C(=O)N1CC1=CC=C(C(O)=O)C=C1 UDCDMLRZYLNYGK-UHFFFAOYSA-N 0.000 description 1
- TUMKOINKXKEKBV-UHFFFAOYSA-N 4-[(3,4-dimethyl-2,5-dioxopyrrol-1-yl)methyl]benzoyl chloride Chemical compound O=C1C(C)=C(C)C(=O)N1CC1=CC=C(C(Cl)=O)C=C1 TUMKOINKXKEKBV-UHFFFAOYSA-N 0.000 description 1
- 241000238017 Astacoidea Species 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- 101100177670 Caenorhabditis elegans hpk-1 gene Proteins 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- 229920001661 Chitosan Polymers 0.000 description 1
- 229920002307 Dextran Polymers 0.000 description 1
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
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- 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
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- KUGRPPRAQNPSQD-UHFFFAOYSA-N OOOOO Chemical compound OOOOO KUGRPPRAQNPSQD-UHFFFAOYSA-N 0.000 description 1
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 1
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- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 229920002807 Thiomer Polymers 0.000 description 1
- BWLKKFSDKDJGDZ-UHFFFAOYSA-N [isocyanato(phenyl)methyl]benzene Chemical compound C=1C=CC=CC=1C(N=C=O)C1=CC=CC=C1 BWLKKFSDKDJGDZ-UHFFFAOYSA-N 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 125000004423 acyloxy group Chemical group 0.000 description 1
- 238000005273 aeration Methods 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 150000001413 amino acids Chemical class 0.000 description 1
- 125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 description 1
- BFUGKXAXHFIYPA-UHFFFAOYSA-N aminooxo-silanol Chemical class N[Si](O)=O BFUGKXAXHFIYPA-UHFFFAOYSA-N 0.000 description 1
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- 125000003118 aryl group Chemical group 0.000 description 1
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- 235000014633 carbohydrates Nutrition 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
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- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- NEHMKBQYUWJMIP-UHFFFAOYSA-N chloromethane Chemical compound ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 description 1
- 150000001851 cinnamic acid derivatives Chemical class 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 150000001913 cyanates Chemical class 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- AYOHIQLKSOJJQH-UHFFFAOYSA-N dibutyltin Chemical compound CCCC[Sn]CCCC AYOHIQLKSOJJQH-UHFFFAOYSA-N 0.000 description 1
- 125000005442 diisocyanate group Chemical group 0.000 description 1
- 230000000447 dimerizing effect Effects 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 229910001873 dinitrogen Inorganic materials 0.000 description 1
- BRWZYZWZBMGMMG-UHFFFAOYSA-J dodecanoate tin(4+) Chemical compound [Sn+4].CCCCCCCCCCCC([O-])=O.CCCCCCCCCCCC([O-])=O.CCCCCCCCCCCC([O-])=O.CCCCCCCCCCCC([O-])=O BRWZYZWZBMGMMG-UHFFFAOYSA-J 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 150000002148 esters Chemical group 0.000 description 1
- 239000012065 filter cake Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 description 1
- 150000002243 furanoses Chemical class 0.000 description 1
- 239000008103 glucose Substances 0.000 description 1
- 150000002367 halogens Chemical group 0.000 description 1
- AXMPFOXRWZXZFA-UHFFFAOYSA-N heptyl carbamate Chemical compound CCCCCCCOC(N)=O AXMPFOXRWZXZFA-UHFFFAOYSA-N 0.000 description 1
- JYVHOGDBFNJNMR-UHFFFAOYSA-N hexane;hydrate Chemical compound O.CCCCCC JYVHOGDBFNJNMR-UHFFFAOYSA-N 0.000 description 1
- 125000002346 iodo group Chemical group I* 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 239000007937 lozenge Substances 0.000 description 1
- TWXDDNPPQUTEOV-FVGYRXGTSA-N methamphetamine hydrochloride Chemical compound Cl.CN[C@@H](C)CC1=CC=CC=C1 TWXDDNPPQUTEOV-FVGYRXGTSA-N 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- HAMGRBXTJNITHG-UHFFFAOYSA-N methyl isocyanate Chemical compound CN=C=O HAMGRBXTJNITHG-UHFFFAOYSA-N 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
- 125000006606 n-butoxy group Chemical group 0.000 description 1
- 125000003506 n-propoxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 244000052769 pathogen Species 0.000 description 1
- 230000001717 pathogenic effect Effects 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- DGTNSSLYPYDJGL-UHFFFAOYSA-N phenyl isocyanate Chemical compound O=C=NC1=CC=CC=C1 DGTNSSLYPYDJGL-UHFFFAOYSA-N 0.000 description 1
- PWXJULSLLONQHY-UHFFFAOYSA-N phenylcarbamic acid Chemical class OC(=O)NC1=CC=CC=C1 PWXJULSLLONQHY-UHFFFAOYSA-N 0.000 description 1
- 238000006552 photochemical reaction Methods 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 150000003214 pyranose derivatives Chemical class 0.000 description 1
- 150000003222 pyridines Chemical class 0.000 description 1
- 230000008707 rearrangement Effects 0.000 description 1
- 238000002390 rotary evaporation Methods 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000012798 spherical particle Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 235000013616 tea Nutrition 0.000 description 1
- 125000004213 tert-butoxy group Chemical group [H]C([H])([H])C(O*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 150000003606 tin compounds Chemical class 0.000 description 1
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 1
- NIUZJTWSUGSWJI-UHFFFAOYSA-M triethyl(methyl)azanium;chloride Chemical compound [Cl-].CC[N+](C)(CC)CC NIUZJTWSUGSWJI-UHFFFAOYSA-M 0.000 description 1
- ILWRPSCZWQJDMK-UHFFFAOYSA-N triethylazanium;chloride Chemical compound Cl.CCN(CC)CC ILWRPSCZWQJDMK-UHFFFAOYSA-N 0.000 description 1
- 238000000870 ultraviolet spectroscopy Methods 0.000 description 1
- 210000002268 wool Anatomy 0.000 description 1
- 229920001221 xylan Polymers 0.000 description 1
- 150000004823 xylans Chemical class 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B57/00—Separation of optically-active compounds
-
- 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
-
- 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
- B01J20/29—Chiral 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
- B01J20/30—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
- B01J20/3231—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
- B01J20/3268—Macromolecular compounds
- B01J20/3272—Polymers obtained by reactions otherwise than involving only carbon to carbon unsaturated bonds
- B01J20/3274—Proteins, nucleic acids, polysaccharides, antibodies or antigens
-
- 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
- B01J20/3268—Macromolecular compounds
- B01J20/328—Polymers on the carrier being further modified
- B01J20/3282—Crosslinked polymers
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08B—POLYSACCHARIDES; DERIVATIVES THEREOF
- C08B15/00—Preparation of other cellulose derivatives or modified cellulose, e.g. complexes
- C08B15/005—Crosslinking of cellulose derivatives
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08B—POLYSACCHARIDES; DERIVATIVES THEREOF
- C08B15/00—Preparation of other cellulose derivatives or modified cellulose, e.g. complexes
- C08B15/05—Derivatives containing elements other than carbon, hydrogen, oxygen, halogens or sulfur
- C08B15/06—Derivatives containing elements other than carbon, hydrogen, oxygen, halogens or sulfur containing nitrogen, e.g. carbamates
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08B—POLYSACCHARIDES; DERIVATIVES THEREOF
- C08B33/00—Preparation of derivatives of amylose
-
- 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
- B01J2220/54—Sorbents specially adapted for analytical or investigative chromatography
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Analytical Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Biochemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Inorganic Chemistry (AREA)
- Polysaccharides And Polysaccharide Derivatives (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Solid-Sorbent Or Filter-Aiding Compositions (AREA)
- Treatment Of Liquids With Adsorbents In General (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH64095 | 1995-03-07 | ||
| CH64095 | 1995-03-07 | ||
| PCT/EP1996/000773 WO1996027615A1 (en) | 1995-03-07 | 1996-02-24 | Photochemically cross-linked polysaccharide derivatives as supports for the chromatographic separation of enantiomers |
| EP9600773 | 1996-02-24 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| FI973149A0 FI973149A0 (fi) | 1997-07-29 |
| FI973149A FI973149A (fi) | 1997-09-04 |
| FI116840B true FI116840B (fi) | 2006-03-15 |
Family
ID=4191727
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FI973149A FI116840B (fi) | 1995-03-07 | 1997-07-29 | Fotokemiallisesti ristisidottuja polysakkaridijohdannaisia alustoina enantiomeerien kromatografiselle erotukselle |
Country Status (18)
| Country | Link |
|---|---|
| US (1) | US6011149A (cs) |
| EP (1) | EP0813546B1 (cs) |
| JP (2) | JP4201832B2 (cs) |
| KR (1) | KR19980702832A (cs) |
| CN (1) | CN1177358A (cs) |
| AT (1) | ATE220691T1 (cs) |
| AU (1) | AU708454B2 (cs) |
| CA (1) | CA2212057C (cs) |
| CY (1) | CY2419B1 (cs) |
| CZ (1) | CZ278797A3 (cs) |
| DE (1) | DE69622381T2 (cs) |
| DK (1) | DK0813546T3 (cs) |
| ES (1) | ES2179935T3 (cs) |
| FI (1) | FI116840B (cs) |
| HU (1) | HUP9802744A3 (cs) |
| NO (1) | NO974092D0 (cs) |
| PT (1) | PT813546E (cs) |
| WO (1) | WO1996027615A1 (cs) |
Families Citing this family (26)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20080132695A1 (en) * | 1995-07-21 | 2008-06-05 | Eric Francotte | Cross-linked Polysaccharide Derivatives |
| US6107492A (en) * | 1998-05-08 | 2000-08-22 | Ucb, S.A. | Process for the preparation of levetiracetam |
| NL1015313C2 (nl) | 2000-05-26 | 2001-11-27 | Dsm Nv | Werkwijze voor de bereiding van enantiomeer verrijkte esters en alcoholen. |
| US20040149660A1 (en) * | 2001-06-15 | 2004-08-05 | Natsuki Kasuya | Separatory agent for optical isomer |
| FR2829947B1 (fr) * | 2001-09-21 | 2004-10-15 | Chiralsep Sarl | Reseau polymere tridimensionnel reticule, son procede de preparation, materiau support comportant ce reseau et leurs utilisations |
| FR2834227A1 (fr) | 2001-12-27 | 2003-07-04 | Chiralsep Sarl | Materiaux supports optiquement actifs, leur procede de preparation et leurs utilisations |
| WO2004085485A1 (en) * | 2003-03-27 | 2004-10-07 | Chirosep | Crosslinked three-dimensional polymer network, method for preparing same, support material comprising same and uses thereof |
| CN100386142C (zh) * | 2003-12-05 | 2008-05-07 | 中国科学院大连化学物理研究所 | 一种合成键合型多糖类手性固定相的方法 |
| CN100387333C (zh) * | 2003-12-05 | 2008-05-14 | 中国科学院大连化学物理研究所 | 一种自由基共聚法制备键合型多糖类手性固定相的方法 |
| CZ2009836A3 (cs) | 2009-12-11 | 2011-06-22 | Contipro C A.S. | Derivát kyseliny hyaluronové oxidovaný v poloze 6 glukosaminové cásti polysacharidu selektivne na aldehyd, zpusob jeho prípravy a zpusob jeho modifikace |
| CZ2009835A3 (cs) | 2009-12-11 | 2011-06-22 | Contipro C A.S. | Zpusob prípravy derivátu kyseliny hyaluronové oxidovaného v poloze 6 glukosaminové cásti polysacharidu selektivne na aldehyd a zpusob jeho modifikace |
| CN102423699B (zh) * | 2011-09-02 | 2013-08-07 | 武汉工程大学 | 一种涂覆型多糖类手性固定相的制备方法 |
| CZ2012136A3 (cs) | 2012-02-28 | 2013-06-05 | Contipro Biotech S.R.O. | Deriváty na bázi kyseliny hyaluronové schopné tvorit hydrogely, zpusob jejich prípravy, hydrogely na bázi techto derivátu, zpusob jejich prípravy a pouzití |
| CZ304512B6 (cs) | 2012-08-08 | 2014-06-11 | Contipro Biotech S.R.O. | Derivát kyseliny hyaluronové, způsob jeho přípravy, způsob jeho modifikace a použití |
| CZ304654B6 (cs) | 2012-11-27 | 2014-08-20 | Contipro Biotech S.R.O. | Nanomicelární kompozice na bázi C6-C18-acylovaného hyaluronanu, způsob přípravy C6-C18-acylovaného hyaluronanu, způsob přípravy nanomicelární kompozice a stabilizované nanomicelární kompozice a použití |
| CZ304267B6 (cs) | 2012-11-27 | 2014-02-05 | Contipro Biotech S.R.O. | Fotoreaktivní derivát kyseliny hyaluronové, způsob jeho přípravy, 3D síťovaný derivát kyseliny hyaluronové, způsob jeho přípravy a použití |
| CZ2014150A3 (cs) | 2014-03-11 | 2015-05-20 | Contipro Biotech S.R.O. | Konjugáty oligomeru kyseliny hyaluronové nebo její soli, způsob jejich přípravy a použití |
| CZ2014451A3 (cs) | 2014-06-30 | 2016-01-13 | Contipro Pharma A.S. | Protinádorová kompozice na bázi kyseliny hyaluronové a anorganických nanočástic, způsob její přípravy a použití |
| CZ309295B6 (cs) | 2015-03-09 | 2022-08-10 | Contipro A.S. | Samonosný, biodegradabilní film na bázi hydrofobizované kyseliny hyaluronové, způsob jeho přípravy a použití |
| KR101956832B1 (ko) | 2015-06-12 | 2019-03-12 | 주식회사 엘지화학 | 폴리카보네이트 수지 조성물 및 이로 이루어진 광학 성형품 |
| CZ2015398A3 (cs) | 2015-06-15 | 2017-02-08 | Contipro A.S. | Způsob síťování polysacharidů s využitím fotolabilních chránicích skupin |
| CZ306662B6 (cs) | 2015-06-26 | 2017-04-26 | Contipro A.S. | Deriváty sulfatovaných polysacharidů, způsob jejich přípravy, způsob jejich modifikace a použití |
| US10385163B2 (en) | 2016-02-18 | 2019-08-20 | Lg Chem, Ltd. | Polycarbonate resin composition and optical molded article using the same |
| CZ308106B6 (cs) | 2016-06-27 | 2020-01-08 | Contipro A.S. | Nenasycené deriváty polysacharidů, způsob jejich přípravy a jejich použití |
| KR102049577B1 (ko) | 2016-10-31 | 2019-11-27 | 주식회사 엘지화학 | 폴리카보네이트 수지 조성물 및 이로 이루어진 광학 성형품 |
| CN111909281B (zh) * | 2020-08-31 | 2022-05-10 | 武汉工程大学 | 直链淀粉-2,3-二(芳香基氨基甲酸酯)-6-脱氧-6-芳香基脲的制备方法 |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3960685A (en) * | 1973-11-12 | 1976-06-01 | Sumitomo Chemical Company, Limited | Photosensitive resin composition containing pullulan or esters thereof |
| DE2626795A1 (de) * | 1975-06-18 | 1976-12-30 | Ciba Geigy Ag | Imidylverbindungen |
| CH599153A5 (cs) * | 1975-06-18 | 1978-05-12 | Ciba Geigy Ag | |
| US4079041A (en) * | 1975-06-18 | 1978-03-14 | Ciba-Geigy Corporation | Crosslinkable polymeric compounds |
| US4861872A (en) * | 1986-03-20 | 1989-08-29 | Daicel Chemical Industries, Ltd. | Alkyl-phenylcarbamate derivative of polysaccharide |
| US4861629A (en) * | 1987-12-23 | 1989-08-29 | Hercules Incorporated | Polyfunctional ethylenically unsaturated cellulosic polymer-based photocurable compositions |
| US5138006A (en) * | 1991-02-11 | 1992-08-11 | Eastman Kodak Company | Radiation polymerizable starch ester-urethanes |
| JP2855307B2 (ja) * | 1992-02-05 | 1999-02-10 | 生化学工業株式会社 | 光反応性グリコサミノグリカン、架橋グリコサミノグリカン及びそれらの製造方法 |
-
1996
- 1996-02-24 DE DE69622381T patent/DE69622381T2/de not_active Expired - Lifetime
- 1996-02-24 AU AU49414/96A patent/AU708454B2/en not_active Expired
- 1996-02-24 CZ CZ972787A patent/CZ278797A3/cs unknown
- 1996-02-24 JP JP52656796A patent/JP4201832B2/ja not_active Expired - Lifetime
- 1996-02-24 AT AT96905796T patent/ATE220691T1/de active
- 1996-02-24 CN CN96192364A patent/CN1177358A/zh active Pending
- 1996-02-24 WO PCT/EP1996/000773 patent/WO1996027615A1/en active IP Right Grant
- 1996-02-24 EP EP96905796A patent/EP0813546B1/en not_active Expired - Lifetime
- 1996-02-24 HU HU9802744A patent/HUP9802744A3/hu unknown
- 1996-02-24 KR KR1019970706239A patent/KR19980702832A/ko not_active Application Discontinuation
- 1996-02-24 PT PT96905796T patent/PT813546E/pt unknown
- 1996-02-24 US US08/894,976 patent/US6011149A/en not_active Expired - Lifetime
- 1996-02-24 DK DK96905796T patent/DK0813546T3/da active
- 1996-02-24 CA CA002212057A patent/CA2212057C/en not_active Expired - Lifetime
- 1996-02-24 ES ES96905796T patent/ES2179935T3/es not_active Expired - Lifetime
-
1997
- 1997-07-29 FI FI973149A patent/FI116840B/fi not_active IP Right Cessation
- 1997-09-05 NO NO974092A patent/NO974092D0/no unknown
-
2003
- 2003-11-12 CY CY0300084A patent/CY2419B1/xx unknown
-
2007
- 2007-08-27 JP JP2007219839A patent/JP4836897B2/ja not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| HUP9802744A2 (hu) | 1999-03-29 |
| MX9706802A (es) | 1997-11-29 |
| CA2212057C (en) | 2007-02-13 |
| JP4201832B2 (ja) | 2008-12-24 |
| JP4836897B2 (ja) | 2011-12-14 |
| JPH11509875A (ja) | 1999-08-31 |
| PT813546E (pt) | 2002-11-29 |
| CZ278797A3 (en) | 1997-11-12 |
| NO974092L (no) | 1997-09-05 |
| AU4941496A (en) | 1996-09-23 |
| JP2008045131A (ja) | 2008-02-28 |
| DK0813546T3 (da) | 2002-11-04 |
| US6011149A (en) | 2000-01-04 |
| FI973149A (fi) | 1997-09-04 |
| DE69622381D1 (de) | 2002-08-22 |
| FI973149A0 (fi) | 1997-07-29 |
| HUP9802744A3 (en) | 1999-04-28 |
| NO974092D0 (no) | 1997-09-05 |
| EP0813546B1 (en) | 2002-07-17 |
| ES2179935T3 (es) | 2003-02-01 |
| EP0813546A1 (en) | 1997-12-29 |
| WO1996027615A1 (en) | 1996-09-12 |
| AU708454B2 (en) | 1999-08-05 |
| CN1177358A (zh) | 1998-03-25 |
| KR19980702832A (ko) | 1998-08-05 |
| DE69622381T2 (de) | 2003-01-16 |
| CA2212057A1 (en) | 1996-09-12 |
| CY2419B1 (en) | 2004-11-12 |
| ATE220691T1 (de) | 2002-08-15 |
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