SK278147B6 - Biodegradable polymers - Google Patents
Biodegradable polymers Download PDFInfo
- Publication number
- SK278147B6 SK278147B6 SK157-93A SK15793A SK278147B6 SK 278147 B6 SK278147 B6 SK 278147B6 SK 15793 A SK15793 A SK 15793A SK 278147 B6 SK278147 B6 SK 278147B6
- Authority
- SK
- Slovakia
- Prior art keywords
- mmol
- polymer
- water
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- 229920002988 biodegradable polymer Polymers 0.000 title claims abstract description 17
- 239000004621 biodegradable polymer Substances 0.000 title claims abstract description 17
- 229920000642 polymer Polymers 0.000 claims abstract description 147
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 27
- 150000005690 diesters Chemical group 0.000 claims abstract description 21
- 229920001577 copolymer Polymers 0.000 claims abstract description 12
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 12
- 229910052799 carbon Inorganic materials 0.000 claims abstract description 11
- 125000000962 organic group Chemical group 0.000 claims abstract description 9
- 229920006037 cross link polymer Polymers 0.000 claims abstract description 6
- 229920000515 polycarbonate Polymers 0.000 claims abstract description 4
- 239000004417 polycarbonate Substances 0.000 claims abstract description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 21
- 239000002245 particle Substances 0.000 claims description 9
- 125000001931 aliphatic group Chemical group 0.000 claims description 8
- 125000000623 heterocyclic group Chemical group 0.000 claims description 8
- 239000000032 diagnostic agent Substances 0.000 claims description 7
- 229940039227 diagnostic agent Drugs 0.000 claims description 7
- 239000001257 hydrogen Substances 0.000 claims description 7
- 229910052760 oxygen Inorganic materials 0.000 claims description 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical group [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
- 239000013543 active substance Substances 0.000 claims description 6
- 150000002430 hydrocarbons Chemical group 0.000 claims description 6
- 239000004215 Carbon black (E152) Chemical group 0.000 claims description 5
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 5
- 125000005842 heteroatom Chemical group 0.000 claims description 5
- 229930195733 hydrocarbon Chemical group 0.000 claims description 5
- 239000001301 oxygen Substances 0.000 claims description 5
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 4
- 125000002947 alkylene group Chemical group 0.000 claims description 4
- 125000001424 substituent group Chemical group 0.000 claims description 4
- 229910052717 sulfur Inorganic materials 0.000 claims description 4
- 239000011593 sulfur Substances 0.000 claims description 4
- 125000004450 alkenylene group Chemical group 0.000 claims description 3
- 229920000578 graft copolymer Polymers 0.000 claims description 3
- NJWJLMYWQCXQOZ-UHFFFAOYSA-N [2-hydroxy-3-(4-propylphenoxy)propyl] 2-methylprop-2-enoate Chemical compound CCCC1=CC=C(OCC(O)COC(=O)C(C)=C)C=C1 NJWJLMYWQCXQOZ-UHFFFAOYSA-N 0.000 claims description 2
- 125000000732 arylene group Chemical group 0.000 claims description 2
- 229920001400 block copolymer Polymers 0.000 claims description 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 2
- 125000002993 cycloalkylene group Chemical group 0.000 claims description 2
- 239000002961 echo contrast media Substances 0.000 claims description 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 2
- 125000001183 hydrocarbyl group Chemical group 0.000 claims 1
- 239000003795 chemical substances by application Substances 0.000 abstract description 7
- 238000004519 manufacturing process Methods 0.000 abstract description 7
- 239000002872 contrast media Substances 0.000 abstract description 4
- 239000007943 implant Substances 0.000 abstract description 4
- 239000011888 foil Substances 0.000 abstract description 3
- 239000006261 foam material Substances 0.000 abstract description 2
- 210000004872 soft tissue Anatomy 0.000 abstract description 2
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 abstract 2
- 238000005452 bending Methods 0.000 abstract 1
- 239000001294 propane Substances 0.000 abstract 1
- 238000001356 surgical procedure Methods 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 174
- 239000000243 solution Substances 0.000 description 132
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 123
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 117
- 239000000499 gel Substances 0.000 description 105
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 92
- 239000011541 reaction mixture Substances 0.000 description 74
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 58
- 239000002904 solvent Substances 0.000 description 55
- 150000001875 compounds Chemical class 0.000 description 53
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 50
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 48
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 46
- 229910052757 nitrogen Inorganic materials 0.000 description 46
- 239000000203 mixture Substances 0.000 description 39
- 239000000047 product Substances 0.000 description 37
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 36
- 239000000178 monomer Substances 0.000 description 36
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 34
- 239000000725 suspension Substances 0.000 description 33
- 238000000034 method Methods 0.000 description 32
- 239000012298 atmosphere Substances 0.000 description 30
- 238000006243 chemical reaction Methods 0.000 description 30
- 238000005160 1H NMR spectroscopy Methods 0.000 description 29
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 29
- 239000012074 organic phase Substances 0.000 description 29
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 29
- 239000004372 Polyvinyl alcohol Substances 0.000 description 28
- 239000007864 aqueous solution Substances 0.000 description 28
- 238000004132 cross linking Methods 0.000 description 28
- -1 polyethylene adipate Polymers 0.000 description 28
- 229920002451 polyvinyl alcohol Polymers 0.000 description 28
- 239000000463 material Substances 0.000 description 26
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 25
- 235000019341 magnesium sulphate Nutrition 0.000 description 25
- 229920002401 polyacrylamide Polymers 0.000 description 25
- 229920006395 saturated elastomer Polymers 0.000 description 23
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 22
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 21
- ZHESMCIWZWYNLC-UHFFFAOYSA-N 2-methylprop-2-enoyloxymethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCOC(=O)C(C)=C ZHESMCIWZWYNLC-UHFFFAOYSA-N 0.000 description 20
- 238000001035 drying Methods 0.000 description 20
- OZAIFHULBGXAKX-VAWYXSNFSA-N AIBN Substances N#CC(C)(C)\N=N\C(C)(C)C#N OZAIFHULBGXAKX-VAWYXSNFSA-N 0.000 description 19
- 238000006116 polymerization reaction Methods 0.000 description 19
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 18
- 238000003756 stirring Methods 0.000 description 18
- QYDMMTAPHLKXNJ-UHFFFAOYSA-N 3,3-dimethoxypropanoyloxymethyl 3,3-dimethoxypropanoate Chemical compound COC(OC)CC(=O)OCOC(=O)CC(OC)OC QYDMMTAPHLKXNJ-UHFFFAOYSA-N 0.000 description 17
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 17
- 239000012299 nitrogen atmosphere Substances 0.000 description 15
- XEZNGIUYQVAUSS-UHFFFAOYSA-N 18-crown-6 Chemical compound C1COCCOCCOCCOCCOCCO1 XEZNGIUYQVAUSS-UHFFFAOYSA-N 0.000 description 14
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 14
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 14
- 235000017557 sodium bicarbonate Nutrition 0.000 description 14
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 13
- 238000010438 heat treatment Methods 0.000 description 13
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 13
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 12
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 12
- 239000002253 acid Substances 0.000 description 12
- 239000004480 active ingredient Substances 0.000 description 12
- 239000010410 layer Substances 0.000 description 12
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 12
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 12
- 239000007787 solid Substances 0.000 description 12
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 11
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 11
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 10
- 239000000839 emulsion Substances 0.000 description 10
- 239000012071 phase Substances 0.000 description 10
- IOLCXVTUBQKXJR-UHFFFAOYSA-M potassium bromide Chemical compound [K+].[Br-] IOLCXVTUBQKXJR-UHFFFAOYSA-M 0.000 description 10
- ODUTZNVTSOAHCJ-UHFFFAOYSA-N 4-(prop-2-enoyloxymethoxycarbonyloxy)butyl prop-2-enoate Chemical compound C=CC(=O)OCCCCOC(=O)OCOC(=O)C=C ODUTZNVTSOAHCJ-UHFFFAOYSA-N 0.000 description 9
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- NZZFYRREKKOMAT-UHFFFAOYSA-N diiodomethane Chemical compound ICI NZZFYRREKKOMAT-UHFFFAOYSA-N 0.000 description 9
- WOBHKFSMXKNTIM-UHFFFAOYSA-N Hydroxyethyl methacrylate Chemical compound CC(=C)C(=O)OCCO WOBHKFSMXKNTIM-UHFFFAOYSA-N 0.000 description 8
- 229920002472 Starch Polymers 0.000 description 8
- CVASMYWHWRNWOX-UHFFFAOYSA-N chloro methyl carbonate Chemical compound COC(=O)OCl CVASMYWHWRNWOX-UHFFFAOYSA-N 0.000 description 8
- 125000000524 functional group Chemical group 0.000 description 8
- 235000019698 starch Nutrition 0.000 description 8
- 239000008107 starch Substances 0.000 description 8
- TYMBNRMIBWOQGH-UHFFFAOYSA-N 3,3-dimethoxypropanoic acid Chemical compound COC(OC)CC(O)=O TYMBNRMIBWOQGH-UHFFFAOYSA-N 0.000 description 7
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 7
- 108090000790 Enzymes Proteins 0.000 description 7
- 102000004190 Enzymes Human genes 0.000 description 7
- 239000001361 adipic acid Substances 0.000 description 7
- 235000011037 adipic acid Nutrition 0.000 description 7
- 239000008346 aqueous phase Substances 0.000 description 7
- 238000006065 biodegradation reaction Methods 0.000 description 7
- 230000015572 biosynthetic process Effects 0.000 description 7
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 7
- 150000001721 carbon Chemical group 0.000 description 7
- 238000003776 cleavage reaction Methods 0.000 description 7
- 238000007334 copolymerization reaction Methods 0.000 description 7
- 229910052740 iodine Inorganic materials 0.000 description 7
- 230000005291 magnetic effect Effects 0.000 description 7
- 239000003094 microcapsule Substances 0.000 description 7
- UQMZDGOZAWEVRF-UHFFFAOYSA-N prop-2-enoyloxymethyl prop-2-enoate Chemical compound C=CC(=O)OCOC(=O)C=C UQMZDGOZAWEVRF-UHFFFAOYSA-N 0.000 description 7
- 230000007017 scission Effects 0.000 description 7
- JLFYPMYFFZMXEQ-UHFFFAOYSA-N 4-(1-prop-2-enoyloxyethoxycarbonyloxy)butyl prop-2-enoate Chemical compound C=CC(=O)OC(C)OC(=O)OCCCCOC(=O)C=C JLFYPMYFFZMXEQ-UHFFFAOYSA-N 0.000 description 6
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 6
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 6
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 6
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 6
- RJKFOVLPORLFTN-LEKSSAKUSA-N Progesterone Chemical compound C1CC2=CC(=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H](C(=O)C)[C@@]1(C)CC2 RJKFOVLPORLFTN-LEKSSAKUSA-N 0.000 description 6
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 6
- MUMGGOZAMZWBJJ-DYKIIFRCSA-N Testostosterone Chemical compound O=C1CC[C@]2(C)[C@H]3CC[C@](C)([C@H](CC4)O)[C@@H]4[C@@H]3CCC2=C1 MUMGGOZAMZWBJJ-DYKIIFRCSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 230000015556 catabolic process Effects 0.000 description 6
- 239000000460 chlorine Substances 0.000 description 6
- 238000006731 degradation reaction Methods 0.000 description 6
- UMGLBHQOFQXXSI-UHFFFAOYSA-N hepta-2,5-dienedioic acid Chemical compound OC(=O)C=CCC=CC(O)=O UMGLBHQOFQXXSI-UHFFFAOYSA-N 0.000 description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 6
- 239000012044 organic layer Substances 0.000 description 6
- 125000006239 protecting group Chemical group 0.000 description 6
- 238000000926 separation method Methods 0.000 description 6
- 238000001228 spectrum Methods 0.000 description 6
- 239000000126 substance Substances 0.000 description 6
- 108090000371 Esterases Proteins 0.000 description 5
- 229910052794 bromium Inorganic materials 0.000 description 5
- 229910052801 chlorine Inorganic materials 0.000 description 5
- JYWJULGYGOLCGW-UHFFFAOYSA-N chloromethyl chloroformate Chemical compound ClCOC(Cl)=O JYWJULGYGOLCGW-UHFFFAOYSA-N 0.000 description 5
- 239000003431 cross linking reagent Substances 0.000 description 5
- 239000012043 crude product Substances 0.000 description 5
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 5
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 description 5
- 229920001519 homopolymer Polymers 0.000 description 5
- 230000007062 hydrolysis Effects 0.000 description 5
- 238000006460 hydrolysis reaction Methods 0.000 description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 5
- 239000011630 iodine Substances 0.000 description 5
- 229920000728 polyester Polymers 0.000 description 5
- 238000010526 radical polymerization reaction Methods 0.000 description 5
- HJPLDEIWOANMRT-UHFFFAOYSA-N (4-hydroxybenzoyl)oxymethyl 4-hydroxybenzoate Chemical compound C1=CC(O)=CC=C1C(=O)OCOC(=O)C1=CC=C(O)C=C1 HJPLDEIWOANMRT-UHFFFAOYSA-N 0.000 description 4
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 4
- KGRVJHAUYBGFFP-UHFFFAOYSA-N 2,2'-Methylenebis(4-methyl-6-tert-butylphenol) Chemical compound CC(C)(C)C1=CC(C)=CC(CC=2C(=C(C=C(C)C=2)C(C)(C)C)O)=C1O KGRVJHAUYBGFFP-UHFFFAOYSA-N 0.000 description 4
- DULDSZGXAZPJRI-UHFFFAOYSA-N 2,4-bis[7-(oxiran-2-yl)heptyl]pentanedioic acid Chemical compound C1OC1CCCCCCCC(C(O)=O)CC(C(=O)O)CCCCCCCC1CO1 DULDSZGXAZPJRI-UHFFFAOYSA-N 0.000 description 4
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 4
- GXAODDSUFOEQCB-UHFFFAOYSA-N 2-(2-methylprop-2-enoyloxymethoxycarbonyloxy)ethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCOC(=O)OCOC(=O)C(C)=C GXAODDSUFOEQCB-UHFFFAOYSA-N 0.000 description 4
- ANQBHOLHRHLQDA-UHFFFAOYSA-N 3-methoxyprop-2-enoyloxymethyl 3-methoxyprop-2-enoate Chemical compound COC=CC(=O)OCOC(=O)C=COC ANQBHOLHRHLQDA-UHFFFAOYSA-N 0.000 description 4
- NFQBQKIUHJNBPV-UHFFFAOYSA-N 9-(oxiran-2-yl)nonanoyloxymethyl 9-(oxiran-2-yl)nonanoate Chemical compound C1OC1CCCCCCCCC(=O)OCOC(=O)CCCCCCCCC1CO1 NFQBQKIUHJNBPV-UHFFFAOYSA-N 0.000 description 4
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 4
- GHASVSINZRGABV-UHFFFAOYSA-N Fluorouracil Chemical compound FC1=CNC(=O)NC1=O GHASVSINZRGABV-UHFFFAOYSA-N 0.000 description 4
- 239000005574 MCPA Substances 0.000 description 4
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 4
- DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 4
- WHKUVVPPKQRRBV-UHFFFAOYSA-N Trasan Chemical compound CC1=CC(Cl)=CC=C1OCC(O)=O WHKUVVPPKQRRBV-UHFFFAOYSA-N 0.000 description 4
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 4
- 125000000217 alkyl group Chemical group 0.000 description 4
- 125000003277 amino group Chemical group 0.000 description 4
- 125000003118 aryl group Chemical group 0.000 description 4
- KCIDZIIHRGYJAE-YGFYJFDDSA-L dipotassium;[(2r,3r,4s,5r,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl] phosphate Chemical class [K+].[K+].OC[C@H]1O[C@H](OP([O-])([O-])=O)[C@H](O)[C@@H](O)[C@H]1O KCIDZIIHRGYJAE-YGFYJFDDSA-L 0.000 description 4
- 238000009826 distribution Methods 0.000 description 4
- WBZKQQHYRPRKNJ-UHFFFAOYSA-L disulfite Chemical compound [O-]S(=O)S([O-])(=O)=O WBZKQQHYRPRKNJ-UHFFFAOYSA-L 0.000 description 4
- 230000002255 enzymatic effect Effects 0.000 description 4
- 150000002148 esters Chemical class 0.000 description 4
- 229960002949 fluorouracil Drugs 0.000 description 4
- 229910021645 metal ion Inorganic materials 0.000 description 4
- GGGDNPWHMNJRFN-UHFFFAOYSA-N metrizoic acid Chemical compound CC(=O)N(C)C1=C(I)C(NC(C)=O)=C(I)C(C(O)=O)=C1I GGGDNPWHMNJRFN-UHFFFAOYSA-N 0.000 description 4
- 231100000252 nontoxic Toxicity 0.000 description 4
- 230000003000 nontoxic effect Effects 0.000 description 4
- 229920000768 polyamine Polymers 0.000 description 4
- 229920000098 polyolefin Polymers 0.000 description 4
- USHAGKDGDHPEEY-UHFFFAOYSA-L potassium persulfate Chemical compound [K+].[K+].[O-]S(=O)(=O)OOS([O-])(=O)=O USHAGKDGDHPEEY-UHFFFAOYSA-L 0.000 description 4
- 239000012254 powdered material Substances 0.000 description 4
- 235000018102 proteins Nutrition 0.000 description 4
- 102000004169 proteins and genes Human genes 0.000 description 4
- 108090000623 proteins and genes Proteins 0.000 description 4
- 239000011780 sodium chloride Substances 0.000 description 4
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 4
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- 239000002202 Polyethylene glycol Substances 0.000 description 3
- 239000004793 Polystyrene Substances 0.000 description 3
- 125000002252 acyl group Chemical group 0.000 description 3
- PWAXUOGZOSVGBO-UHFFFAOYSA-N adipoyl chloride Chemical compound ClC(=O)CCCCC(Cl)=O PWAXUOGZOSVGBO-UHFFFAOYSA-N 0.000 description 3
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 3
- 235000001014 amino acid Nutrition 0.000 description 3
- 150000001413 amino acids Chemical class 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 3
- 239000007900 aqueous suspension Substances 0.000 description 3
- 125000003710 aryl alkyl group Chemical group 0.000 description 3
- 239000001569 carbon dioxide Substances 0.000 description 3
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- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
- A61L31/00—Materials for other surgical articles, e.g. stents, stent-grafts, shunts, surgical drapes, guide wires, materials for adhesion prevention, occluding devices, surgical gloves, tissue fixation devices
- A61L31/14—Materials characterised by their function or physical properties, e.g. injectable or lubricating compositions, shape-memory materials, surface modified materials
- A61L31/148—Materials at least partially resorbable by the body
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S977/00—Nanotechnology
- Y10S977/84—Manufacture, treatment, or detection of nanostructure
- Y10S977/895—Manufacture, treatment, or detection of nanostructure having step or means utilizing chemical property
- Y10S977/896—Chemical synthesis, e.g. chemical bonding or breaking
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Epidemiology (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Radiology & Medical Imaging (AREA)
- Materials Engineering (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Vascular Medicine (AREA)
- Surgery (AREA)
- Pharmacology & Pharmacy (AREA)
- Organic Chemistry (AREA)
- Heart & Thoracic Surgery (AREA)
- Dispersion Chemistry (AREA)
- Inorganic Chemistry (AREA)
- Acoustics & Sound (AREA)
- Physics & Mathematics (AREA)
- Dermatology (AREA)
- Oral & Maxillofacial Surgery (AREA)
- Transplantation (AREA)
- General Chemical & Material Sciences (AREA)
- Biochemistry (AREA)
- Molecular Biology (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Biological Depolymerization Polymers (AREA)
- Polyesters Or Polycarbonates (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Macromonomer-Based Addition Polymer (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Other Resins Obtained By Reactions Not Involving Carbon-To-Carbon Unsaturated Bonds (AREA)
- Polyamides (AREA)
- Materials For Medical Uses (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB909019650A GB9019650D0 (en) | 1990-09-07 | 1990-09-07 | Chemical compounds |
| GB919114678A GB9114678D0 (en) | 1991-07-08 | 1991-07-08 | Chemical compounds |
| PCT/EP1991/001751 WO1992004392A1 (en) | 1990-09-07 | 1991-09-07 | Polymers containing diester units |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| SK15793A3 SK15793A3 (en) | 1993-10-06 |
| SK278147B6 true SK278147B6 (en) | 1996-02-07 |
Family
ID=26297628
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SK157-93A SK278147B6 (en) | 1990-09-07 | 1991-09-07 | Biodegradable polymers |
Country Status (24)
| Country | Link |
|---|---|
| US (2) | US5534250A (de) |
| EP (1) | EP0547126B1 (de) |
| JP (1) | JP3161728B2 (de) |
| AT (1) | ATE134668T1 (de) |
| AU (1) | AU662490B2 (de) |
| BG (1) | BG61268B1 (de) |
| BR (1) | BR9106819A (de) |
| CA (1) | CA2091165C (de) |
| CZ (1) | CZ282532B6 (de) |
| DE (1) | DE69117518T2 (de) |
| DK (1) | DK0547126T3 (de) |
| ES (1) | ES2084180T3 (de) |
| FI (1) | FI930991A (de) |
| GR (1) | GR3019624T3 (de) |
| HU (1) | HU221088B1 (de) |
| IE (1) | IE73487B1 (de) |
| IL (1) | IL99438A (de) |
| NO (1) | NO304432B1 (de) |
| OA (1) | OA10052A (de) |
| PH (1) | PH31064A (de) |
| RO (1) | RO112033B1 (de) |
| SG (1) | SG49084A1 (de) |
| SK (1) | SK278147B6 (de) |
| WO (1) | WO1992004392A1 (de) |
Families Citing this family (40)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB9106686D0 (en) * | 1991-03-28 | 1991-05-15 | Hafslund Nycomed As | Improvements in or relating to contrast agents |
| GB9106673D0 (en) * | 1991-03-28 | 1991-05-15 | Hafslund Nycomed As | Improvements in or relating to contrast agents |
| WO1992021382A1 (en) * | 1991-06-03 | 1992-12-10 | Holmes, Michael, John | Improvements in or relating to contrast agents |
| MX9205298A (es) * | 1991-09-17 | 1993-05-01 | Steven Carl Quay | Medios gaseosos de contraste de ultrasonido y metodo para seleccionar gases para usarse como medios de contraste de ultrasonido |
| US5674468A (en) * | 1992-03-06 | 1997-10-07 | Nycomed Imaging As | Contrast agents comprising gas-containing or gas-generating polymer microparticles or microballoons |
| EP0627942B1 (de) * | 1992-03-06 | 1999-09-15 | Nycomed Imaging As | Verbesserungen in bezug auf kontrastmittel |
| GB9204918D0 (en) | 1992-03-06 | 1992-04-22 | Nycomed As | Chemical compounds |
| US6383470B1 (en) | 1992-09-26 | 2002-05-07 | Thomas Fritzsch | Microparticle preparations made of biodegradable copolymers |
| IL108416A (en) | 1993-01-25 | 1998-10-30 | Sonus Pharma Inc | Colloids with phase difference as contrast ultrasound agents |
| FR2705352B1 (fr) * | 1993-05-19 | 1995-08-04 | Cray Valley Sa | Procédé de dégradation de déchets de polyesters insaturés en vue de leur recyclage. |
| GB9318288D0 (en) * | 1993-09-03 | 1993-10-20 | Nycomed Imaging As | Improvements in or relating to contrast agents |
| GB9417941D0 (en) * | 1994-09-06 | 1994-10-26 | Nycomed Imaging As | Improvements in or relating to contrast agents |
| DE19726191A1 (de) * | 1997-06-20 | 1998-12-24 | Bayer Ag | Verwendung von Jod-phenyl-carbonat-haltigen Polycarbonaten zur Herstellung von speziellen Formteilen |
| US7343710B2 (en) * | 1998-07-03 | 2008-03-18 | I.D.A Limited | Method and apparatus for controlling pests |
| GB9814507D0 (en) * | 1998-07-03 | 1998-09-02 | Univ Southampton | A method and apparatus for controlling pests |
| US6498153B1 (en) * | 1998-12-31 | 2002-12-24 | Akzo Nobel N.V. | Extended release growth promoting two component composition |
| US6426145B1 (en) | 1999-05-20 | 2002-07-30 | Scimed Life Systems, Inc. | Radiopaque compositions for visualization of medical devices |
| DE10101387A1 (de) | 2001-01-13 | 2002-07-18 | Merck Patent Gmbh | Polyester mit Methacrylatendgruppen |
| CN100341589C (zh) | 2002-05-24 | 2007-10-10 | 血管技术国际股份公司 | 用于涂覆医用植入物的组合物和方法 |
| US8313760B2 (en) | 2002-05-24 | 2012-11-20 | Angiotech International Ag | Compositions and methods for coating medical implants |
| US20030235610A1 (en) * | 2002-06-21 | 2003-12-25 | Piedmont Pharmaceuticals, Llc | Liposomes containing biologically active compounds |
| JP2007513650A (ja) * | 2003-11-20 | 2007-05-31 | アンジオテック インターナショナル アーゲー | 移植可能なセンサーおよび移植可能なポンプならびに瘢痕化抑制剤 |
| US8012457B2 (en) | 2004-06-04 | 2011-09-06 | Acusphere, Inc. | Ultrasound contrast agent dosage formulation |
| AU2005100176A4 (en) * | 2005-03-01 | 2005-04-07 | Gym Tv Pty Ltd | Garbage bin clip |
| JP5581202B2 (ja) * | 2007-05-02 | 2014-08-27 | タイレックス・インコーポレイテッド | ジヒドロキシベンゾエートポリマーおよびその使用 |
| DE102008008522A1 (de) * | 2008-02-11 | 2009-08-13 | Magforce Nanotechnologies Ag | Implantierbare Nanopartikel-enthaltende Produkte |
| DK2334378T3 (da) | 2008-08-19 | 2014-07-07 | Xenoport Inc | Prodrugs af methylhydrogenfumarat, farmaceutiske sammensætninger deraf og fremgangsmåder til anvendelse |
| US20110015672A1 (en) * | 2009-07-17 | 2011-01-20 | Tyco Healthcare Group Lp | Method for Coating a Medical Device |
| US20140056973A1 (en) | 2012-08-22 | 2014-02-27 | Xenoport, Inc. | Oral Dosage Forms Having a High Loading of a Methyl Hydrogen Fumarate Prodrug |
| CA2882713A1 (en) | 2012-08-22 | 2014-02-27 | Xenoport, Inc. | Methods of administering monomethyl fumarate and prodrugs thereof having reduced side effects |
| SG11201507371RA (en) | 2013-03-14 | 2015-10-29 | Alkermes Pharma Ireland Ltd | Prodrugs of fumarates and their use in treating various deseases |
| US8669281B1 (en) | 2013-03-14 | 2014-03-11 | Alkermes Pharma Ireland Limited | Prodrugs of fumarates and their use in treating various diseases |
| US10179118B2 (en) | 2013-03-24 | 2019-01-15 | Arbor Pharmaceuticals, Llc | Pharmaceutical compositions of dimethyl fumarate |
| WO2014197860A1 (en) | 2013-06-07 | 2014-12-11 | Xenoport, Inc. | Method of making monomethyl fumarate |
| US9421182B2 (en) | 2013-06-21 | 2016-08-23 | Xenoport, Inc. | Cocrystals of dimethyl fumarate |
| JP2016534133A (ja) | 2013-09-06 | 2016-11-04 | ゼノポート，インコーポレイティド | （ｎ，ｎ−ジエチルカルバモイル）メチル メチル（２ｅ）ブト−２−エン−１，４−ジオエートの結晶形態、その合成方法及び使用 |
| JP6337135B2 (ja) | 2014-02-24 | 2018-06-06 | アルカーメス ファーマ アイルランド リミテッド | フマル酸エステルのスルホンアミドプロドラッグ及びスルフィンアミドプロドラッグ並びに種々の疾患の治療におけるその使用 |
| US9999672B2 (en) | 2014-03-24 | 2018-06-19 | Xenoport, Inc. | Pharmaceutical compositions of fumaric acid esters |
| US20220119588A1 (en) * | 2019-02-04 | 2022-04-21 | Aditya Birla Chemicals (Thailand) Ltd. (Epoxy Division) | Recyclable and reworkable epoxy resins |
| WO2023168562A1 (zh) * | 2022-03-07 | 2023-09-14 | 上纬创新育成股份有限公司 | 含碳酸酯的不饱和化合物、其制备方法、其制备的固化物及降解固化物的方法 |
Family Cites Families (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE95108C (de) * | ||||
| US2341334A (en) * | 1939-03-14 | 1944-02-08 | Du Pont | Interpolymers of alkylidene esters of alpha-methylene monocarboxylic acids with vinyl and vinylidene compounds |
| DE1104900B (de) * | 1953-11-23 | 1961-04-13 | Helmut Junghans Dr Ing | Armbanduhrwerk |
| US2839572A (en) * | 1956-03-29 | 1958-06-17 | Union Carbide Corp | Allylidene dicrotonates and process for their production |
| BE592804A (de) * | 1959-07-11 | |||
| US3293220A (en) * | 1962-10-11 | 1966-12-20 | Toyo Rayon Co Ltd | Process for heat stabilization of polyoxymethylene |
| JPS4926946B1 (de) * | 1970-12-24 | 1974-07-13 | ||
| DD95108A1 (de) * | 1971-12-06 | 1973-01-12 | ||
| US3894118A (en) * | 1974-01-21 | 1975-07-08 | Itt | Crosslinking agents for fluorocarbon polymers |
| NL174734C (nl) * | 1974-02-18 | 1984-08-01 | Tno | Werkwijze voor het bereiden van onder invloed van water afbreekbare kunststofmaterialen, alsmede voorwerpen, gevormd uit kunststofmaterialen verkregen onder toepassing van de werkwijze. |
| US4180646A (en) * | 1975-01-28 | 1979-12-25 | Alza Corporation | Novel orthoester polymers and orthocarbonate polymers |
| CH653558A5 (fr) * | 1979-11-23 | 1986-01-15 | Battelle Memorial Institute | Fil de suture muni d'un manchon protecteur. |
| JPS6014861A (ja) * | 1983-07-05 | 1985-01-25 | 株式会社日本メデイカル・サプライ | 癒着防止材 |
| US4481353A (en) * | 1983-10-07 | 1984-11-06 | The Children's Medical Center Corporation | Bioresorbable polyesters and polyester composites |
| NL8402178A (nl) * | 1984-07-10 | 1986-02-03 | Rijksuniversiteit | Entstuk, geschikt voor behandeling door reconstructieve chirurgie van beschadigingen van beenachtig materiaal. |
| DE3610808A1 (de) * | 1985-03-29 | 1986-10-02 | Pentron Corp., Wallingford, Conn. | Dental-klebmittel |
| JP2551756B2 (ja) * | 1985-05-07 | 1996-11-06 | 武田薬品工業株式会社 | ポリオキシカルボン酸エステルおよびその製造法 |
| AU2536388A (en) * | 1987-09-30 | 1989-04-18 | Ecoplastics Limited | Production of photodegradable polyester plastics |
| NL8703115A (nl) * | 1987-12-23 | 1989-07-17 | Groningen Science Park | Biodegradeerbare polyurethanen, daarop gebaseerde voortbrengselen, en polyesterpolyol prepolymeren. |
-
1991
- 1991-09-06 PH PH43068A patent/PH31064A/en unknown
- 1991-09-07 AU AU85256/91A patent/AU662490B2/en not_active Ceased
- 1991-09-07 SG SG1996005902A patent/SG49084A1/en unknown
- 1991-09-07 ES ES91916326T patent/ES2084180T3/es not_active Expired - Lifetime
- 1991-09-07 DK DK91916326.1T patent/DK0547126T3/da active
- 1991-09-07 US US07/982,746 patent/US5534250A/en not_active Expired - Lifetime
- 1991-09-07 WO PCT/EP1991/001751 patent/WO1992004392A1/en active IP Right Grant
- 1991-09-07 HU HU9300608A patent/HU221088B1/hu unknown
- 1991-09-07 RO RO93-00306A patent/RO112033B1/ro unknown
- 1991-09-07 CA CA002091165A patent/CA2091165C/en not_active Expired - Fee Related
- 1991-09-07 BR BR919106819A patent/BR9106819A/pt not_active Application Discontinuation
- 1991-09-07 JP JP51546591A patent/JP3161728B2/ja not_active Expired - Fee Related
- 1991-09-07 DE DE69117518T patent/DE69117518T2/de not_active Expired - Fee Related
- 1991-09-07 SK SK157-93A patent/SK278147B6/sk unknown
- 1991-09-07 AT AT91916326T patent/ATE134668T1/de not_active IP Right Cessation
- 1991-09-07 EP EP91916326A patent/EP0547126B1/de not_active Expired - Lifetime
- 1991-09-08 IL IL9943891A patent/IL99438A/en not_active IP Right Cessation
- 1991-09-09 IE IE315491A patent/IE73487B1/en not_active IP Right Cessation
-
1993
- 1993-03-04 CZ CZ93337A patent/CZ282532B6/cs unknown
- 1993-03-05 OA OA60347A patent/OA10052A/en unknown
- 1993-03-05 BG BG97499A patent/BG61268B1/bg unknown
- 1993-03-05 NO NO930807A patent/NO304432B1/no not_active IP Right Cessation
- 1993-03-05 FI FI930991A patent/FI930991A/fi unknown
-
1995
- 1995-06-02 US US08/458,612 patent/US5693321A/en not_active Expired - Fee Related
-
1996
- 1996-04-10 GR GR960401021T patent/GR3019624T3/el unknown
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