DE60306693T2 - Heterozyklische Verbindungen enthaltende opthalmische Gegenstände und Verfahren zu deren Herstellung - Google Patents
Heterozyklische Verbindungen enthaltende opthalmische Gegenstände und Verfahren zu deren Herstellung Download PDFInfo
- Publication number
- DE60306693T2 DE60306693T2 DE60306693T DE60306693T DE60306693T2 DE 60306693 T2 DE60306693 T2 DE 60306693T2 DE 60306693 T DE60306693 T DE 60306693T DE 60306693 T DE60306693 T DE 60306693T DE 60306693 T2 DE60306693 T2 DE 60306693T2
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- Germany
- Prior art keywords
- lens
- heterocyclic
- heterocyclic compound
- compound
- group
- Prior art date
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- Expired - Lifetime
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- 150000002391 heterocyclic compounds Chemical class 0.000 title claims description 58
- 238000000034 method Methods 0.000 title claims description 43
- 238000002360 preparation method Methods 0.000 title description 7
- 239000000203 mixture Substances 0.000 claims description 45
- -1 heterocyclic amine Chemical group 0.000 claims description 30
- 239000002243 precursor Substances 0.000 claims description 25
- 150000001875 compounds Chemical class 0.000 claims description 24
- 229920000642 polymer Polymers 0.000 claims description 24
- 239000000460 chlorine Substances 0.000 claims description 22
- 230000000845 anti-microbial effect Effects 0.000 claims description 21
- 229910052801 chlorine Inorganic materials 0.000 claims description 20
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 14
- 238000000576 coating method Methods 0.000 claims description 13
- 230000000813 microbial effect Effects 0.000 claims description 13
- 239000011248 coating agent Substances 0.000 claims description 12
- 229910052760 oxygen Inorganic materials 0.000 claims description 12
- 239000000017 hydrogel Substances 0.000 claims description 11
- 229910052794 bromium Inorganic materials 0.000 claims description 9
- 125000000623 heterocyclic group Chemical group 0.000 claims description 9
- 229910052739 hydrogen Inorganic materials 0.000 claims description 9
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 8
- 239000001257 hydrogen Substances 0.000 claims description 8
- 239000001301 oxygen Substances 0.000 claims description 8
- 229910052717 sulfur Inorganic materials 0.000 claims description 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 7
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 6
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 6
- 125000005842 heteroatom Chemical group 0.000 claims description 6
- 238000004519 manufacturing process Methods 0.000 claims description 6
- NLAIHECABDOZBR-UHFFFAOYSA-M sodium 2,2-bis(2-methylprop-2-enoyloxymethyl)butyl 2-methylprop-2-enoate 2-hydroxyethyl 2-methylprop-2-enoate 2-methylprop-2-enoate Chemical compound [Na+].CC(=C)C([O-])=O.CC(=C)C(=O)OCCO.CCC(COC(=O)C(C)=C)(COC(=O)C(C)=C)COC(=O)C(C)=C NLAIHECABDOZBR-UHFFFAOYSA-M 0.000 claims description 6
- 239000011593 sulfur Substances 0.000 claims description 6
- UURVHRGPGCBHIC-UHFFFAOYSA-N 3-(ethenoxycarbonylamino)propanoic acid 4-[[[[[[[[[[[[[[[[[[[[[[[[[[[4-ethenoxycarbonyloxybutyl(dimethyl)silyl]oxy-dimethylsilyl]oxy-dimethylsilyl]oxy-dimethylsilyl]oxy-dimethylsilyl]oxy-dimethylsilyl]oxy-dimethylsilyl]oxy-dimethylsilyl]oxy-dimethylsilyl]oxy-dimethylsilyl]oxy-dimethylsilyl]oxy-dimethylsilyl]oxy-dimethylsilyl]oxy-dimethylsilyl]oxy-dimethylsilyl]oxy-dimethylsilyl]oxy-dimethylsilyl]oxy-dimethylsilyl]oxy-dimethylsilyl]oxy-dimethylsilyl]oxy-dimethylsilyl]oxy-dimethylsilyl]oxy-dimethylsilyl]oxy-dimethylsilyl]oxy-dimethylsilyl]oxy-dimethylsilyl]oxy-dimethylsilyl]butyl ethenyl carbonate 1-ethenylpyrrolidin-2-one ethenyl N-[3-tris(trimethylsilyloxy)silylpropyl]carbamate Chemical compound C=CN1CCCC1=O.OC(=O)CCNC(=O)OC=C.C[Si](C)(C)O[Si](CCCNC(=O)OC=C)(O[Si](C)(C)C)O[Si](C)(C)C.C[Si](C)(CCCCOC(=O)OC=C)O[Si](C)(C)O[Si](C)(C)O[Si](C)(C)O[Si](C)(C)O[Si](C)(C)O[Si](C)(C)O[Si](C)(C)O[Si](C)(C)O[Si](C)(C)O[Si](C)(C)O[Si](C)(C)O[Si](C)(C)O[Si](C)(C)O[Si](C)(C)O[Si](C)(C)O[Si](C)(C)O[Si](C)(C)O[Si](C)(C)O[Si](C)(C)O[Si](C)(C)O[Si](C)(C)O[Si](C)(C)O[Si](C)(C)O[Si](C)(C)O[Si](C)(C)O[Si](C)(C)CCCCOC(=O)OC=C UURVHRGPGCBHIC-UHFFFAOYSA-N 0.000 claims description 5
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 5
- 229910052799 carbon Inorganic materials 0.000 claims description 5
- 239000008199 coating composition Substances 0.000 claims description 5
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 5
- 229920001296 polysiloxane Polymers 0.000 claims description 5
- 150000001252 acrylic acid derivatives Chemical class 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 4
- 229910052736 halogen Inorganic materials 0.000 claims description 4
- 150000002367 halogens Chemical class 0.000 claims description 4
- 239000004599 antimicrobial Substances 0.000 claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 3
- 229920000728 polyester Polymers 0.000 claims description 3
- 229920000570 polyether Polymers 0.000 claims description 3
- HHEDWQWUXLSDHJ-UHFFFAOYSA-N (3-chloro-4-ethyl-2-oxo-1,3-oxazolidin-4-yl)methyl prop-2-enoate Chemical compound C=CC(=O)OCC1(CC)COC(=O)N1Cl HHEDWQWUXLSDHJ-UHFFFAOYSA-N 0.000 claims description 2
- VISGDCFUXPEFDW-UHFFFAOYSA-N 1,3-dichloro-2,2,5,5-tetramethylimidazolidin-4-one Chemical compound CC1(C)N(Cl)C(=O)C(C)(C)N1Cl VISGDCFUXPEFDW-UHFFFAOYSA-N 0.000 claims description 2
- BROYWHABVCPAPN-UHFFFAOYSA-N 1,3-dichloro-4,4,5,5-tetramethylimidazolidin-2-one Chemical compound CC1(C)N(Cl)C(=O)N(Cl)C1(C)C BROYWHABVCPAPN-UHFFFAOYSA-N 0.000 claims description 2
- KEQGZUUPPQEDPF-UHFFFAOYSA-N 1,3-dichloro-5,5-dimethylimidazolidine-2,4-dione Chemical compound CC1(C)N(Cl)C(=O)N(Cl)C1=O KEQGZUUPPQEDPF-UHFFFAOYSA-N 0.000 claims description 2
- HUPNLWZFGMGNKB-UHFFFAOYSA-N 3-chloro-4,4-dimethyl-1,3-oxazolidin-2-one Chemical compound CC1(C)COC(=O)N1Cl HUPNLWZFGMGNKB-UHFFFAOYSA-N 0.000 claims description 2
- ZKQDCIXGCQPQNV-UHFFFAOYSA-N Calcium hypochlorite Chemical compound [Ca+2].Cl[O-].Cl[O-] ZKQDCIXGCQPQNV-UHFFFAOYSA-N 0.000 claims description 2
- 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 claims description 2
- 241000124008 Mammalia Species 0.000 claims description 2
- 239000004952 Polyamide Substances 0.000 claims description 2
- 125000003118 aryl group Chemical group 0.000 claims description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
- CEJLBZWIKQJOAT-UHFFFAOYSA-N dichloroisocyanuric acid Chemical compound ClN1C(=O)NC(=O)N(Cl)C1=O CEJLBZWIKQJOAT-UHFFFAOYSA-N 0.000 claims description 2
- WJRBRSLFGCUECM-UHFFFAOYSA-N hydantoin Chemical compound O=C1CNC(=O)N1 WJRBRSLFGCUECM-UHFFFAOYSA-N 0.000 claims description 2
- 229940091173 hydantoin Drugs 0.000 claims description 2
- 150000002734 metacrylic acid derivatives Chemical class 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- 229920002647 polyamide Polymers 0.000 claims description 2
- 239000011734 sodium Substances 0.000 claims description 2
- 229910052708 sodium Inorganic materials 0.000 claims description 2
- 125000004417 unsaturated alkyl group Chemical group 0.000 claims description 2
- 230000000379 polymerizing effect Effects 0.000 claims 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 1
- 125000003011 styrenyl group Chemical class [H]\C(*)=C(/[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims 1
- 125000001424 substituent group Chemical group 0.000 claims 1
- 241000219739 Lens Species 0.000 description 113
- 239000000243 solution Substances 0.000 description 25
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 25
- 241000894006 Bacteria Species 0.000 description 24
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 19
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 16
- WOBHKFSMXKNTIM-UHFFFAOYSA-N Hydroxyethyl methacrylate Chemical compound CC(=C)C(=O)OCCO WOBHKFSMXKNTIM-UHFFFAOYSA-N 0.000 description 15
- 102100026735 Coagulation factor VIII Human genes 0.000 description 13
- 101000911390 Homo sapiens Coagulation factor VIII Proteins 0.000 description 13
- 239000000178 monomer Substances 0.000 description 13
- 238000006243 chemical reaction Methods 0.000 description 11
- 239000000463 material Substances 0.000 description 11
- 238000004806 packaging method and process Methods 0.000 description 11
- 229910052757 nitrogen Inorganic materials 0.000 description 10
- LOKCTEFSRHRXRJ-UHFFFAOYSA-I dipotassium trisodium dihydrogen phosphate hydrogen phosphate dichloride Chemical compound P(=O)(O)(O)[O-].[K+].P(=O)(O)([O-])[O-].[Na+].[Na+].[Cl-].[K+].[Cl-].[Na+] LOKCTEFSRHRXRJ-UHFFFAOYSA-I 0.000 description 9
- 239000002953 phosphate buffered saline Substances 0.000 description 9
- WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 description 7
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 7
- 239000003999 initiator Substances 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 230000005764 inhibitory process Effects 0.000 description 6
- SUKJFIGYRHOWBL-UHFFFAOYSA-N sodium hypochlorite Chemical compound [Na+].Cl[O-] SUKJFIGYRHOWBL-UHFFFAOYSA-N 0.000 description 6
- 239000007983 Tris buffer Substances 0.000 description 5
- 229920001577 copolymer Polymers 0.000 description 5
- 239000008367 deionised water Substances 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- HWSSEYVMGDIFMH-UHFFFAOYSA-N 2-[2-[2-(2-methylprop-2-enoyloxy)ethoxy]ethoxy]ethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCOCCOCCOC(=O)C(C)=C HWSSEYVMGDIFMH-UHFFFAOYSA-N 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 4
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- 238000009472 formulation Methods 0.000 description 4
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- 238000003860 storage Methods 0.000 description 4
- GNMCBCWJPIVMQR-UHFFFAOYSA-N (4-ethyl-2-oxo-1,3-oxazolidin-4-yl)methyl prop-2-enoate Chemical compound C=CC(=O)OCC1(CC)COC(=O)N1 GNMCBCWJPIVMQR-UHFFFAOYSA-N 0.000 description 3
- WUGOQZFPNUYUOO-UHFFFAOYSA-N 2-trimethylsilyloxyethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCO[Si](C)(C)C WUGOQZFPNUYUOO-UHFFFAOYSA-N 0.000 description 3
- DLHQZZUEERVIGQ-UHFFFAOYSA-N 3,7-dimethyl-3-octanol Chemical compound CCC(C)(O)CCCC(C)C DLHQZZUEERVIGQ-UHFFFAOYSA-N 0.000 description 3
- FCMBXDLFGKHPLS-UHFFFAOYSA-N 4-ethyl-4-(hydroxymethyl)-1,3-oxazolidin-2-one Chemical compound CCC1(CO)COC(=O)N1 FCMBXDLFGKHPLS-UHFFFAOYSA-N 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
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- 235000014647 Lens culinaris subsp culinaris Nutrition 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
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- VBYLGQXERITIBP-UHFFFAOYSA-N n-[dimethylamino(methyl)silyl]-n-methylmethanamine Chemical compound CN(C)[SiH](C)N(C)C VBYLGQXERITIBP-UHFFFAOYSA-N 0.000 description 3
- 230000003287 optical effect Effects 0.000 description 3
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- 239000002904 solvent Substances 0.000 description 3
- WKBPZYKAUNRMKP-UHFFFAOYSA-N 1-[2-(2,4-dichlorophenyl)pentyl]1,2,4-triazole Chemical compound C=1C=C(Cl)C=C(Cl)C=1C(CCC)CN1C=NC=N1 WKBPZYKAUNRMKP-UHFFFAOYSA-N 0.000 description 2
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 2
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- VCYCUECVHJJFIQ-UHFFFAOYSA-N 2-[3-(benzotriazol-2-yl)-4-hydroxyphenyl]ethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCC1=CC=C(O)C(N2N=C3C=CC=CC3=N2)=C1 VCYCUECVHJJFIQ-UHFFFAOYSA-N 0.000 description 2
- ZSPOJBDHHFFJAP-UHFFFAOYSA-M 3-chlorobenzoate;tetrabutylazanium Chemical group [O-]C(=O)C1=CC=CC(Cl)=C1.CCCC[N+](CCCC)(CCCC)CCCC ZSPOJBDHHFFJAP-UHFFFAOYSA-M 0.000 description 2
- BESKSSIEODQWBP-UHFFFAOYSA-N 3-tris(trimethylsilyloxy)silylpropyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCC[Si](O[Si](C)(C)C)(O[Si](C)(C)C)O[Si](C)(C)C BESKSSIEODQWBP-UHFFFAOYSA-N 0.000 description 2
- 206010067484 Adverse reaction Diseases 0.000 description 2
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- MQDJYUACMFCOFT-UHFFFAOYSA-N bis[2-(1-hydroxycyclohexyl)phenyl]methanone Chemical compound C=1C=CC=C(C(=O)C=2C(=CC=CC=2)C2(O)CCCCC2)C=1C1(O)CCCCC1 MQDJYUACMFCOFT-UHFFFAOYSA-N 0.000 description 2
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- UQGFMSUEHSUPRD-UHFFFAOYSA-N disodium;3,7-dioxido-2,4,6,8,9-pentaoxa-1,3,5,7-tetraborabicyclo[3.3.1]nonane Chemical compound [Na+].[Na+].O1B([O-])OB2OB([O-])OB1O2 UQGFMSUEHSUPRD-UHFFFAOYSA-N 0.000 description 2
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- 239000012956 1-hydroxycyclohexylphenyl-ketone Substances 0.000 description 1
- LTHJXDSHSVNJKG-UHFFFAOYSA-N 2-[2-[2-[2-(2-methylprop-2-enoyloxy)ethoxy]ethoxy]ethoxy]ethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCOCCOCCOCCOC(=O)C(C)=C LTHJXDSHSVNJKG-UHFFFAOYSA-N 0.000 description 1
- IOAOAKDONABGPZ-UHFFFAOYSA-N 2-amino-2-ethylpropane-1,3-diol Chemical compound CCC(N)(CO)CO IOAOAKDONABGPZ-UHFFFAOYSA-N 0.000 description 1
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- 0 CC(C)(*(*)C1(C)*)C(*)(*)N1Cl Chemical compound CC(C)(*(*)C1(C)*)C(*)(*)N1Cl 0.000 description 1
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Classifications
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- G02B1/00—Optical elements characterised by the material of which they are made; Optical coatings for optical elements
- G02B1/04—Optical elements characterised by the material of which they are made; Optical coatings for optical elements made of organic materials, e.g. plastics
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- A—HUMAN NECESSITIES
- 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
- A61L27/00—Materials for grafts or prostheses or for coating grafts or prostheses
- A61L27/50—Materials characterised by their function or physical properties, e.g. injectable or lubricating compositions, shape-memory materials, surface modified materials
- A61L27/54—Biologically active materials, e.g. therapeutic substances
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J7/00—Chemical treatment or coating of shaped articles made of macromolecular substances
- C08J7/12—Chemical modification
-
- G—PHYSICS
- G02—OPTICS
- G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
- G02B1/00—Optical elements characterised by the material of which they are made; Optical coatings for optical elements
- G02B1/04—Optical elements characterised by the material of which they are made; Optical coatings for optical elements made of organic materials, e.g. plastics
- G02B1/041—Lenses
- G02B1/043—Contact lenses
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- A—HUMAN NECESSITIES
- 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
- A61L2300/00—Biologically active materials used in bandages, wound dressings, absorbent pads or medical devices
- A61L2300/20—Biologically active materials used in bandages, wound dressings, absorbent pads or medical devices containing or releasing organic materials
- A61L2300/202—Biologically active materials used in bandages, wound dressings, absorbent pads or medical devices containing or releasing organic materials with halogen atoms, e.g. triclosan, povidone-iodine
-
- A—HUMAN NECESSITIES
- 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
- A61L2300/00—Biologically active materials used in bandages, wound dressings, absorbent pads or medical devices
- A61L2300/40—Biologically active materials used in bandages, wound dressings, absorbent pads or medical devices characterised by a specific therapeutic activity or mode of action
- A61L2300/404—Biocides, antimicrobial agents, antiseptic agents
-
- A—HUMAN NECESSITIES
- 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
- A61L2300/00—Biologically active materials used in bandages, wound dressings, absorbent pads or medical devices
- A61L2300/60—Biologically active materials used in bandages, wound dressings, absorbent pads or medical devices characterised by a special physical form
- A61L2300/606—Coatings
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- A—HUMAN NECESSITIES
- 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
- A61L2430/00—Materials or treatment for tissue regeneration
- A61L2430/16—Materials or treatment for tissue regeneration for reconstruction of eye parts, e.g. intraocular lens, cornea
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Physics & Mathematics (AREA)
- Life Sciences & Earth Sciences (AREA)
- Optics & Photonics (AREA)
- General Physics & Mathematics (AREA)
- Veterinary Medicine (AREA)
- General Chemical & Material Sciences (AREA)
- Transplantation (AREA)
- Epidemiology (AREA)
- Animal Behavior & Ethology (AREA)
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- Dermatology (AREA)
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- Biomedical Technology (AREA)
- Engineering & Computer Science (AREA)
- Oral & Maxillofacial Surgery (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Eyeglasses (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Surface Treatment Of Optical Elements (AREA)
- Apparatus For Disinfection Or Sterilisation (AREA)
- Coating Of Shaped Articles Made Of Macromolecular Substances (AREA)
- Prostheses (AREA)
- Materials For Medical Uses (AREA)
Applications Claiming Priority (4)
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| US34858502P | 2002-01-14 | 2002-01-14 | |
| US348585P | 2002-01-14 | ||
| US320572 | 2002-12-16 | ||
| US10/320,572 US7173073B2 (en) | 2002-01-14 | 2002-12-16 | Ophthalmic devices containing heterocyclic compounds and methods for their production |
Publications (2)
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| DE60306693D1 DE60306693D1 (de) | 2006-08-24 |
| DE60306693T2 true DE60306693T2 (de) | 2007-08-02 |
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| EP (1) | EP1327893B1 (enExample) |
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| BR (1) | BR0302680A (enExample) |
| CA (1) | CA2416335C (enExample) |
| DE (1) | DE60306693T2 (enExample) |
| TW (1) | TWI265306B (enExample) |
| WO (1) | WO2003060572A1 (enExample) |
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| KR101389300B1 (ko) * | 2005-02-14 | 2014-04-25 | 존슨 앤드 존슨 비젼 케어, 인코포레이티드 | 안과용 렌즈의 제조방법, 안과용 장치 및 콘택트 렌즈 |
| EP1851572A2 (en) * | 2005-02-17 | 2007-11-07 | Oxyband Technologies, Inc. | Method and apparatus for supplying gas to an area |
| US9052529B2 (en) | 2006-02-10 | 2015-06-09 | Johnson & Johnson Vision Care, Inc. | Comfortable ophthalmic device and methods of its production |
| US20070195260A1 (en) * | 2006-02-22 | 2007-08-23 | Microban Products Company | Antimicrobial spectacle |
| US8648127B2 (en) * | 2008-06-02 | 2014-02-11 | The Boeing Company | Self decontaminating chemical and biological agent resistant coating |
| US8722715B2 (en) * | 2008-11-07 | 2014-05-13 | NovaBay Pharmaceuticals | Antimicrobial oxazolidinone, hydantoin and imidazolidinone compositions |
| US8883077B2 (en) * | 2010-02-18 | 2014-11-11 | Auburn University | Disinfecting, nonbleaching N-halamine for use with contact lens |
| WO2012054521A2 (en) * | 2010-10-19 | 2012-04-26 | Novabay Pharmaceuticlas, Inc. | Antimicrobial polyether and polyol compounds |
| JP5944987B2 (ja) * | 2011-06-30 | 2016-07-05 | ディーエスエム アイピー アセッツ ビー．ブイ． | シリコーン含有モノマー |
| US9010933B2 (en) | 2013-02-12 | 2015-04-21 | Shin-Etsu Silicones Of America, Inc. | Silicone contact lens and method for manufacturing thereof |
| JP6351384B2 (ja) * | 2014-06-03 | 2018-07-04 | 株式会社メニコン | コンタクトレンズおよびその製造方法 |
| JP6351385B2 (ja) * | 2014-06-03 | 2018-07-04 | 株式会社メニコン | コンタクトレンズの製造方法 |
| EP4481478A3 (en) | 2017-06-07 | 2025-03-26 | Alcon Inc. | Silicone hydrogel contact lenses |
| AU2018279285B2 (en) | 2017-06-07 | 2020-12-17 | Alcon Inc. | Silicone hydrogel contact lenses |
| US10843422B2 (en) | 2017-06-07 | 2020-11-24 | Alcon, Inc. | Method for producing silicone hydrogel contact lenses |
| CA3103339A1 (en) * | 2018-06-18 | 2019-12-26 | Cornell University | Systems and methods for n-halamine-dopamine copolymers for high-performance, low-cost, and easy-to-apply antimicrobial coatings |
| WO2025006728A1 (en) * | 2023-06-28 | 2025-01-02 | Ppg Industries Ohio, Inc. | Coated optical articles demonstrating anti-fogging properties and methods of providing an optical article with anti-fogging properties |
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| GB1391438A (en) | 1971-04-20 | 1975-04-23 | Contact Lens Mfg Ltd | Hydrophilic copolymers and articles formed therefrom |
| US3916033A (en) * | 1971-06-09 | 1975-10-28 | High Voltage Engineering Corp | Contact lens |
| US3854982A (en) * | 1972-05-12 | 1974-12-17 | Hydroplastics Inc | Method for preparing hydrophilic polymer grafts including irradiation |
| US4330383A (en) * | 1978-07-18 | 1982-05-18 | Polymer Technology Corporation | Dimensionally stable oxygen permeable hard contact lens material and method of manufacture |
| JPS6027965B2 (ja) | 1980-02-23 | 1985-07-02 | 東洋コンタクトレンズ株式会社 | コンタクトレンズに付着した汚れの除去方法 |
| US4973493A (en) * | 1982-09-29 | 1990-11-27 | Bio-Metric Systems, Inc. | Method of improving the biocompatibility of solid surfaces |
| GB8501955D0 (en) | 1985-01-25 | 1985-02-27 | Contact Lens Mfg Ltd | Disinfection of contact lenses |
| DE3517615C2 (de) * | 1985-05-15 | 1987-04-09 | Titmus Eurocon Kontaktlinsen GmbH, 8750 Aschaffenburg | Verfahren zur Hydrophilierung eines Siliconkautschukformkörpers an seiner Oberfläche |
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| GB9118597D0 (en) * | 1991-08-30 | 1991-10-16 | Biocompatibles Ltd | Polymer treatments |
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| FR2772033A1 (fr) | 1997-12-05 | 1999-06-04 | Essilor Int | Procede de fabrication d'un materiau polymere transparent resistant au depot de proteines, materiau obtenu par ce procede, lentilles de contact et implants intraoculaires faits de ce materiau |
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| US6469177B1 (en) | 1997-12-09 | 2002-10-22 | Auburn University | Surface active N-Halamine compounds |
| US5998498A (en) | 1998-03-02 | 1999-12-07 | Johnson & Johnson Vision Products, Inc. | Soft contact lenses |
| US6087415A (en) | 1998-06-11 | 2000-07-11 | Johnson & Johnson Vision Care, Inc. | Biomedical devices with hydrophilic coatings |
| JP2000010055A (ja) | 1998-06-19 | 2000-01-14 | Seed Co Ltd | 親水性眼用レンズ及びその製造方法 |
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| JP3824791B2 (ja) | 1998-10-01 | 2006-09-20 | 株式会社ニデック | 眼内レンズの製造方法 |
| SE9803481D0 (sv) | 1998-10-13 | 1998-10-13 | Pharmacia & Upjohn Ab | Photocurable siloxane polymers |
| CZ20011290A3 (cs) | 1998-10-13 | 2001-11-14 | Pharmacia Groningen Bv | Injikovatelné intraokulární čočky |
| AU760960B2 (en) | 1998-10-29 | 2003-05-22 | Advanced Medical Optics, Inc. | Intraocular lenses made from polymeric compositions |
| US6029808A (en) | 1999-01-29 | 2000-02-29 | Johnson & Johnson Vision Products, Inc. | Primary package for contact lens |
| US6630243B2 (en) * | 1999-05-20 | 2003-10-07 | Bausch & Lomb Incorporated | Surface treatment of silicone hydrogel contact lenses comprising hydrophilic polymer chains attached to an intermediate carbon coating |
| DE60043907D1 (de) | 1999-10-07 | 2010-04-08 | Johnson & Johnson Vision Care | Weiche Kontaktlinsen |
| CN1313842C (zh) | 1999-10-12 | 2007-05-02 | 庄臣及庄臣视力保护公司 | 接触透镜涂层选择及其制造工艺 |
| JP4229822B2 (ja) | 2003-12-12 | 2009-02-25 | 帝人テクノプロダクツ株式会社 | ベルト補強用アラミド繊維コードの製造方法 |
-
2002
- 2002-12-16 US US10/320,572 patent/US7173073B2/en not_active Expired - Lifetime
-
2003
- 2003-01-10 WO PCT/US2003/000772 patent/WO2003060572A1/en not_active Ceased
- 2003-01-10 AU AU2003205091A patent/AU2003205091A1/en not_active Abandoned
- 2003-01-10 KR KR1020030002511A patent/KR100901085B1/ko not_active Expired - Fee Related
- 2003-01-14 DE DE60306693T patent/DE60306693T2/de not_active Expired - Lifetime
- 2003-01-14 AU AU2003200095A patent/AU2003200095B2/en not_active Ceased
- 2003-01-14 BR BR0302680-9A patent/BR0302680A/pt not_active IP Right Cessation
- 2003-01-14 TW TW092101060A patent/TWI265306B/zh not_active IP Right Cessation
- 2003-01-14 CA CA2416335A patent/CA2416335C/en not_active Expired - Fee Related
- 2003-01-14 CN CN03120672A patent/CN1441262A/zh active Pending
- 2003-01-14 EP EP03250210A patent/EP1327893B1/en not_active Expired - Lifetime
- 2003-01-14 JP JP2003006084A patent/JP4642323B2/ja not_active Expired - Fee Related
-
2006
- 2006-12-20 US US11/613,496 patent/US7767730B2/en not_active Expired - Lifetime
-
2010
- 2010-06-01 US US12/791,217 patent/US8017665B2/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| AU2003200095B8 (en) | 2003-07-31 |
| US20070155852A1 (en) | 2007-07-05 |
| CN1441262A (zh) | 2003-09-10 |
| BR0302680A (pt) | 2004-08-24 |
| TWI265306B (en) | 2006-11-01 |
| DE60306693D1 (de) | 2006-08-24 |
| KR20030061689A (ko) | 2003-07-22 |
| AU2003205091A1 (en) | 2003-07-30 |
| JP2003248200A (ja) | 2003-09-05 |
| US20030139490A1 (en) | 2003-07-24 |
| EP1327893A1 (en) | 2003-07-16 |
| EP1327893B1 (en) | 2006-07-12 |
| US8017665B2 (en) | 2011-09-13 |
| US20100238399A1 (en) | 2010-09-23 |
| CA2416335A1 (en) | 2003-07-14 |
| CA2416335C (en) | 2011-09-27 |
| JP4642323B2 (ja) | 2011-03-02 |
| US7173073B2 (en) | 2007-02-06 |
| US7767730B2 (en) | 2010-08-03 |
| AU2003200095B2 (en) | 2007-07-26 |
| TW200307142A (en) | 2003-12-01 |
| WO2003060572A1 (en) | 2003-07-24 |
| KR100901085B1 (ko) | 2009-06-08 |
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