CA2416335C - Ophthalmic devices containing heterocyclic compounds and methods for their production - Google Patents
Ophthalmic devices containing heterocyclic compounds and methods for their production Download PDFInfo
- Publication number
- CA2416335C CA2416335C CA2416335A CA2416335A CA2416335C CA 2416335 C CA2416335 C CA 2416335C CA 2416335 A CA2416335 A CA 2416335A CA 2416335 A CA2416335 A CA 2416335A CA 2416335 C CA2416335 C CA 2416335C
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- Prior art keywords
- lens
- heterocyclic
- heterocyclic compound
- compound
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- 150000002391 heterocyclic compounds Chemical class 0.000 title claims abstract description 66
- 238000000034 method Methods 0.000 title claims abstract description 52
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 9
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- 239000000203 mixture Substances 0.000 claims description 51
- -1 heterocyclic amine Chemical class 0.000 claims description 40
- 150000001875 compounds Chemical class 0.000 claims description 36
- 239000002243 precursor Substances 0.000 claims description 33
- 238000000576 coating method Methods 0.000 claims description 21
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- 239000011248 coating agent Substances 0.000 claims description 15
- 229910052760 oxygen Inorganic materials 0.000 claims description 13
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 12
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 12
- 239000001301 oxygen Substances 0.000 claims description 12
- 239000000017 hydrogel Substances 0.000 claims description 11
- 229910052739 hydrogen Inorganic materials 0.000 claims description 9
- 229910052794 bromium Inorganic materials 0.000 claims description 8
- 239000001257 hydrogen Substances 0.000 claims description 8
- 229910052717 sulfur Inorganic materials 0.000 claims description 8
- 239000008199 coating composition Substances 0.000 claims description 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 6
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- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 5
- 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 5
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- 230000010065 bacterial adhesion Effects 0.000 description 1
- 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 1
- 235000012206 bottled water Nutrition 0.000 description 1
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- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
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- 238000003618 dip coating Methods 0.000 description 1
- BNIILDVGGAEEIG-UHFFFAOYSA-L disodium hydrogen phosphate Chemical compound [Na+].[Na+].OP([O-])([O-])=O BNIILDVGGAEEIG-UHFFFAOYSA-L 0.000 description 1
- 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 1
- 238000004821 distillation Methods 0.000 description 1
- 239000003651 drinking water Substances 0.000 description 1
- 239000000806 elastomer Substances 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- FXPHJTKVWZVEGA-UHFFFAOYSA-N ethenyl hydrogen carbonate Chemical class OC(=O)OC=C FXPHJTKVWZVEGA-UHFFFAOYSA-N 0.000 description 1
- SUPCQIBBMFXVTL-UHFFFAOYSA-N ethyl 2-methylprop-2-enoate Chemical compound CCOC(=O)C(C)=C SUPCQIBBMFXVTL-UHFFFAOYSA-N 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000007730 finishing process Methods 0.000 description 1
- NBVXSUQYWXRMNV-UHFFFAOYSA-N fluoromethane Chemical compound FC NBVXSUQYWXRMNV-UHFFFAOYSA-N 0.000 description 1
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- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- FQPSGWSUVKBHSU-UHFFFAOYSA-N methacrylamide Chemical compound CC(=C)C(N)=O FQPSGWSUVKBHSU-UHFFFAOYSA-N 0.000 description 1
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- 230000003278 mimic effect Effects 0.000 description 1
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- 229940088644 n,n-dimethylacrylamide Drugs 0.000 description 1
- YLGYACDQVQQZSW-UHFFFAOYSA-N n,n-dimethylprop-2-enamide Chemical compound CN(C)C(=O)C=C YLGYACDQVQQZSW-UHFFFAOYSA-N 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- AUONHKJOIZSQGR-UHFFFAOYSA-N oxophosphane Chemical compound P=O AUONHKJOIZSQGR-UHFFFAOYSA-N 0.000 description 1
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 description 1
- 230000002093 peripheral effect Effects 0.000 description 1
- 229920000435 poly(dimethylsiloxane) Polymers 0.000 description 1
- 229920001197 polyacetylene Polymers 0.000 description 1
- 229920001721 polyimide Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 229920000193 polymethacrylate Polymers 0.000 description 1
- 229920005862 polyol Polymers 0.000 description 1
- 229920000098 polyolefin Polymers 0.000 description 1
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- 239000004814 polyurethane Substances 0.000 description 1
- 239000011118 polyvinyl acetate Substances 0.000 description 1
- 229940075065 polyvinyl acetate Drugs 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 235000019422 polyvinyl alcohol Nutrition 0.000 description 1
- 229940068984 polyvinyl alcohol Drugs 0.000 description 1
- 239000004800 polyvinyl chloride Substances 0.000 description 1
- 229920000915 polyvinyl chloride Polymers 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 230000035755 proliferation Effects 0.000 description 1
- SOGFHWHHBILCSX-UHFFFAOYSA-J prop-2-enoate silicon(4+) Chemical class [Si+4].[O-]C(=O)C=C.[O-]C(=O)C=C.[O-]C(=O)C=C.[O-]C(=O)C=C SOGFHWHHBILCSX-UHFFFAOYSA-J 0.000 description 1
- 125000006239 protecting group Chemical group 0.000 description 1
- 238000010926 purge Methods 0.000 description 1
- VTGOHKSTWXHQJK-UHFFFAOYSA-N pyrimidin-2-ol Chemical class OC1=NC=CC=N1 VTGOHKSTWXHQJK-UHFFFAOYSA-N 0.000 description 1
- 239000005060 rubber Substances 0.000 description 1
- 238000012216 screening Methods 0.000 description 1
- 229920002379 silicone rubber Polymers 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- AJPJDKMHJJGVTQ-UHFFFAOYSA-M sodium dihydrogen phosphate Chemical compound [Na+].OP(O)([O-])=O AJPJDKMHJJGVTQ-UHFFFAOYSA-M 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 125000005504 styryl group Chemical group 0.000 description 1
- 125000000542 sulfonic acid group Chemical group 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
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- BFGQTWYXWNCTSX-UHFFFAOYSA-N triazine-4,5-dione Chemical class O=C1C=NN=NC1=O BFGQTWYXWNCTSX-UHFFFAOYSA-N 0.000 description 1
- 231100000397 ulcer Toxicity 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
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Classifications
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- 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
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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
-
- 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)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Dermatology (AREA)
- Molecular Biology (AREA)
- 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)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US34858502P | 2002-01-14 | 2002-01-14 | |
| US60/348,585 | 2002-01-14 | ||
| US10/320,572 | 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)
| Publication Number | Publication Date |
|---|---|
| CA2416335A1 CA2416335A1 (en) | 2003-07-14 |
| CA2416335C true CA2416335C (en) | 2011-09-27 |
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|---|---|---|---|
| CA2416335A Expired - Fee Related CA2416335C (en) | 2002-01-14 | 2003-01-14 | Ophthalmic devices containing heterocyclic compounds and methods for their production |
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| Country | Link |
|---|---|
| US (3) | US7173073B2 (enExample) |
| EP (1) | EP1327893B1 (enExample) |
| JP (1) | JP4642323B2 (enExample) |
| KR (1) | KR100901085B1 (enExample) |
| CN (1) | CN1441262A (enExample) |
| AU (2) | AU2003205091A1 (enExample) |
| 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 |
Family Cites Families (52)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| US4681948A (en) * | 1986-03-31 | 1987-07-21 | Ppg Industries, Inc. | N,N'dihalo-2-imidazolidinones |
| US5712327A (en) | 1987-01-07 | 1998-01-27 | Chang; Sing-Hsiung | Soft gas permeable contact lens having improved clinical performance |
| GB2218823B (en) | 1988-05-19 | 1992-02-19 | Sauflon Pharm Ltd | Disinfection of contact lenses |
| US5115056A (en) | 1989-06-20 | 1992-05-19 | Ciba-Geigy Corporation | Fluorine and/or silicone containing poly(alkylene-oxide)-block copolymers and contact lenses thereof |
| US5002794A (en) * | 1989-08-31 | 1991-03-26 | The Board Of Regents Of The University Of Washington | Method of controlling the chemical structure of polymeric films by plasma |
| GB9004881D0 (en) * | 1990-03-05 | 1990-05-02 | Biocompatibles Ltd | Method of improving the ocular of synthetic polymers haemo and biocompatibility |
| ZA913506B (en) * | 1990-05-22 | 1992-02-26 | Alcon Lab Inc | Double redox system for disinfecting contact lenses |
| JPH0476518A (ja) * | 1990-07-19 | 1992-03-11 | Sangi Co Ltd | 抗菌性コンタクトレンズ |
| GB9113875D0 (en) | 1991-06-27 | 1991-08-14 | Biointeractions Ltd | Polymer coatings |
| GB9118597D0 (en) * | 1991-08-30 | 1991-10-16 | Biocompatibles Ltd | Polymer treatments |
| US5256420A (en) * | 1991-12-23 | 1993-10-26 | Ciba-Geigy Corporation | Method of imparting antimicrobial acitivity to an ophthalmic composition |
| FR2688782A1 (fr) * | 1992-03-19 | 1993-09-24 | Essilor Int | Nouveaux chromenes heterocycliques et leur utilisation dans le domaine de l'optique ophtalmique. |
| JPH06123860A (ja) | 1992-10-09 | 1994-05-06 | Tokyo Keikaku:Kk | 酸素透過性ハードコンタクトレンズ |
| US5944853A (en) | 1992-10-26 | 1999-08-31 | Johnson & Johnson Vision Products, Inc. | Method for preparing halotriazine dye- and vinyl sulfone dye-monomer compounds |
| US5350800A (en) * | 1993-01-19 | 1994-09-27 | Medtronic, Inc. | Method for improving the biocompatibility of solid surfaces |
| JPH06329679A (ja) * | 1993-01-20 | 1994-11-29 | Nissan Chem Ind Ltd | 光学活性β−アミノアルコキシボラン錯体 |
| WO1994020118A1 (en) * | 1993-03-12 | 1994-09-15 | Auburn University | Novel polymeric cyclic n-halamine biocidal compounds |
| US6294185B1 (en) | 1993-03-12 | 2001-09-25 | Auburn University | Monomeric and polymeric cyclic amine and N-halamine compounds |
| US5374662A (en) | 1993-03-15 | 1994-12-20 | Bausch & Lomb Incorporated | Fumarate and fumaramide siloxane hydrogel compositions |
| US5340583A (en) | 1993-05-06 | 1994-08-23 | Allergan, Inc. | Antimicrobial lenses and lens care systems |
| US5849311A (en) * | 1996-10-28 | 1998-12-15 | Biopolymerix, Inc. | Contact-killing non-leaching antimicrobial materials |
| US5760100B1 (en) | 1994-09-06 | 2000-11-14 | Ciba Vision Corp | Extended wear ophthalmic lens |
| TW585882B (en) | 1995-04-04 | 2004-05-01 | Novartis Ag | A method of using a contact lens as an extended wear lens and a method of screening an ophthalmic lens for utility as an extended-wear lens |
| AU7502996A (en) | 1995-11-08 | 1997-05-29 | American Ink Jet Corporation | Refilling ink jet cartridges |
| KR100468803B1 (ko) * | 1995-12-07 | 2005-04-19 | 바슈 앤드 롬 인코포레이티드 | 실리콘히드로겔의모듈러스를감소시키는데유용한단량체단위 |
| US5882357A (en) | 1996-09-13 | 1999-03-16 | The Regents Of The University Of California | Durable and regenerable microbiocidal textiles |
| FR2757866B1 (fr) | 1996-12-30 | 2004-12-17 | Catalyse | Polymeres comportant des groupes ammoniums quaternaires, leur utilisation pour la fabrication d'un materiau a propretes antibacteriennes et leurs procedes de preparation |
| NZ509286A (en) | 1997-12-02 | 2001-02-23 | Hoya Healthcare Corp | Haptic portion of soft intraocular lens absorbs compressive forces applied to optic portion of lens |
| 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 |
| US5902818A (en) | 1997-12-09 | 1999-05-11 | Auburn University | Surface active N-halamine compounds |
| 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 |
| JP2000016905A (ja) | 1998-07-01 | 2000-01-18 | Tokuriki Kagaku Kenkyusho:Kk | 抗菌抗かび剤および抗菌抗かび材料 |
| 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 |
| DE60306693T2 (de) | 2007-08-02 |
| 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 |
| 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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