DE60223589T2 - Verfahren zum modifizieren der oberfläche von biomedizinischen gegenständen - Google Patents
Verfahren zum modifizieren der oberfläche von biomedizinischen gegenständen Download PDFInfo
- Publication number
- DE60223589T2 DE60223589T2 DE60223589T DE60223589T DE60223589T2 DE 60223589 T2 DE60223589 T2 DE 60223589T2 DE 60223589 T DE60223589 T DE 60223589T DE 60223589 T DE60223589 T DE 60223589T DE 60223589 T2 DE60223589 T2 DE 60223589T2
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- Prior art keywords
- alkyl
- radical
- alkylene
- substituted
- independently
- Prior art date
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- Expired - Lifetime
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- 238000000034 method Methods 0.000 title claims abstract description 26
- 239000000463 material Substances 0.000 claims abstract description 62
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- 239000013590 bulk material Substances 0.000 claims abstract description 37
- 238000000576 coating method Methods 0.000 claims abstract description 20
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- 239000000178 monomer Substances 0.000 claims abstract description 15
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- 230000008569 process Effects 0.000 claims abstract description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims description 68
- -1 benzylene Chemical group 0.000 claims description 64
- 239000001257 hydrogen Substances 0.000 claims description 60
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 43
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 28
- 125000000217 alkyl group Chemical group 0.000 claims description 25
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- 230000009021 linear effect Effects 0.000 claims description 21
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- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 20
- 229910052757 nitrogen Chemical group 0.000 claims description 20
- RWRIWBAIICGTTQ-UHFFFAOYSA-N difluoromethane Chemical compound FCF RWRIWBAIICGTTQ-UHFFFAOYSA-N 0.000 claims description 17
- 125000002947 alkylene group Chemical group 0.000 claims description 13
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- KIUKXJAPPMFGSW-DNGZLQJQSA-N (2S,3S,4S,5R,6R)-6-[(2S,3R,4R,5S,6R)-3-Acetamido-2-[(2S,3S,4R,5R,6R)-6-[(2R,3R,4R,5S,6R)-3-acetamido-2,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl]oxy-2-carboxy-4,5-dihydroxyoxan-3-yl]oxy-5-hydroxy-6-(hydroxymethyl)oxan-4-yl]oxy-3,4,5-trihydroxyoxane-2-carboxylic acid Chemical compound CC(=O)N[C@H]1[C@H](O)O[C@H](CO)[C@@H](O)[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@H](O[C@H]2[C@@H]([C@@H](O[C@H]3[C@@H]([C@@H](O)[C@H](O)[C@H](O3)C(O)=O)O)[C@H](O)[C@@H](CO)O2)NC(C)=O)[C@@H](C(O)=O)O1 KIUKXJAPPMFGSW-DNGZLQJQSA-N 0.000 claims description 10
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- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 5
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- CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 claims description 4
- HDTRYLNUVZCQOY-UHFFFAOYSA-N α-D-glucopyranosyl-α-D-glucopyranoside Natural products OC1C(O)C(O)C(CO)OC1OC1C(O)C(O)C(O)C(CO)O1 HDTRYLNUVZCQOY-UHFFFAOYSA-N 0.000 claims description 3
- 125000003161 (C1-C6) alkylene group Chemical group 0.000 claims description 3
- PMMYEEVYMWASQN-DMTCNVIQSA-N Hydroxyproline Chemical compound O[C@H]1CN[C@H](C(O)=O)C1 PMMYEEVYMWASQN-DMTCNVIQSA-N 0.000 claims description 3
- HDTRYLNUVZCQOY-WSWWMNSNSA-N Trehalose Natural products O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@@H]1O[C@@H]1[C@H](O)[C@@H](O)[C@@H](O)[C@@H](CO)O1 HDTRYLNUVZCQOY-WSWWMNSNSA-N 0.000 claims description 3
- HDTRYLNUVZCQOY-LIZSDCNHSA-N alpha,alpha-trehalose Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@@H]1O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 HDTRYLNUVZCQOY-LIZSDCNHSA-N 0.000 claims description 3
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- 125000002883 imidazolyl group Chemical group 0.000 claims description 3
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- 125000004642 (C1-C12) alkoxy group Chemical group 0.000 claims description 2
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 2
- ONIBWKKTOPOVIA-BYPYZUCNSA-N L-Proline Chemical compound OC(=O)[C@@H]1CCCN1 ONIBWKKTOPOVIA-BYPYZUCNSA-N 0.000 claims description 2
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- PMMYEEVYMWASQN-UHFFFAOYSA-N dl-hydroxyproline Natural products OC1C[NH2+]C(C([O-])=O)C1 PMMYEEVYMWASQN-UHFFFAOYSA-N 0.000 claims description 2
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- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 claims description 2
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- GBXQPDCOMJJCMJ-UHFFFAOYSA-M trimethyl-[6-(trimethylazaniumyl)hexyl]azanium;bromide Chemical compound [Br-].C[N+](C)(C)CCCCCC[N+](C)(C)C GBXQPDCOMJJCMJ-UHFFFAOYSA-M 0.000 claims description 2
- 125000002962 imidazol-1-yl group Chemical group [*]N1C([H])=NC([H])=C1[H] 0.000 claims 1
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims 1
- SNOOUWRIMMFWNE-UHFFFAOYSA-M sodium;6-[(3,4,5-trimethoxybenzoyl)amino]hexanoate Chemical compound [Na+].COC1=CC(C(=O)NCCCCCC([O-])=O)=CC(OC)=C1OC SNOOUWRIMMFWNE-UHFFFAOYSA-M 0.000 claims 1
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- 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
- A61L2400/00—Materials characterised by their function or physical properties
- A61L2400/18—Modification of implant surfaces in order to improve biocompatibility, cell growth, fixation of biomolecules, e.g. plasma treatment
Landscapes
- Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Transplantation (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Dermatology (AREA)
- General Health & Medical Sciences (AREA)
- Oral & Maxillofacial Surgery (AREA)
- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Optics & Photonics (AREA)
- Macromonomer-Based Addition Polymer (AREA)
- Materials For Medical Uses (AREA)
- Coating Of Shaped Articles Made Of Macromolecular Substances (AREA)
- Application Of Or Painting With Fluid Materials (AREA)
- Eyeglasses (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP01811088 | 2001-11-13 | ||
| EP01811088 | 2001-11-13 | ||
| PCT/EP2002/012658 WO2003042724A1 (en) | 2001-11-13 | 2002-11-12 | Method for modifying the surface of biomedical articles |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE60223589D1 DE60223589D1 (de) | 2007-12-27 |
| DE60223589T2 true DE60223589T2 (de) | 2008-11-20 |
Family
ID=8184238
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE60223589T Expired - Lifetime DE60223589T2 (de) | 2001-11-13 | 2002-11-12 | Verfahren zum modifizieren der oberfläche von biomedizinischen gegenständen |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US6878399B2 (enExample) |
| EP (1) | EP1451615B1 (enExample) |
| JP (1) | JP2005512115A (enExample) |
| AT (1) | ATE378612T1 (enExample) |
| CA (1) | CA2467092A1 (enExample) |
| DE (1) | DE60223589T2 (enExample) |
| TW (1) | TW200407367A (enExample) |
| WO (1) | WO2003042724A1 (enExample) |
Cited By (1)
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|---|---|---|---|---|
| DE102018127812A1 (de) | 2018-11-07 | 2020-05-07 | Fachhochschule Kiel | Kontaktlinse mit einer Oberflächenbeschichtung und Herstellungsverfahren |
Families Citing this family (52)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1245272A1 (en) * | 2001-03-30 | 2002-10-02 | Ucb S.A. | Substrates, preparation and use |
| JP5026956B2 (ja) * | 2004-05-12 | 2012-09-19 | サーモディクス，インコーポレイティド | 医療用具のための天然生分解性多糖コーティング |
| US20060057209A1 (en) * | 2004-09-16 | 2006-03-16 | Predicant Biosciences, Inc. | Methods, compositions and devices, including microfluidic devices, comprising coated hydrophobic surfaces |
| EP1948750A1 (en) * | 2005-11-16 | 2008-07-30 | FUJIFILM Corporation | Surface-hydrophilic structure |
| JP5094081B2 (ja) * | 2005-11-17 | 2012-12-12 | 富士フイルム株式会社 | 親水性部材及びその製造方法 |
| JP2007252699A (ja) * | 2006-03-24 | 2007-10-04 | Mcrotech Kk | ゲル組成物、それを用いた移植用材料及びそれらの製造方法 |
| US20100119833A1 (en) * | 2006-07-25 | 2010-05-13 | Niels Jorgen Madsen | Photo-curing of thermoplastic coatings |
| EP2052045A4 (en) | 2006-08-18 | 2012-09-12 | Commw Scient Ind Res Org | POLYMERIC COATINGS AND METHODS FOR FORMING SAME |
| US8795782B2 (en) | 2006-08-18 | 2014-08-05 | Commonwealth Scientific And Industrial Research Organisation | Polymeric coatings and methods for forming them |
| US8012591B2 (en) * | 2006-09-21 | 2011-09-06 | Fujifilm Corporation | Hydrophilic composition and hydrophilic member |
| JP2008238711A (ja) * | 2007-03-28 | 2008-10-09 | Fujifilm Corp | 親水性部材及び下塗り組成物 |
| US20090029179A1 (en) * | 2007-05-14 | 2009-01-29 | Fujifilm Corporation | Two-liquid composition, hydrophilic composition and hydrophilic member |
| US8460743B2 (en) * | 2008-03-18 | 2013-06-11 | Novartis Ag | Coating process for ophthalmic lenses |
| JP2009227809A (ja) * | 2008-03-21 | 2009-10-08 | Fujifilm Corp | 親水性組成物及び親水性処理部材 |
| JP5449803B2 (ja) * | 2009-03-06 | 2014-03-19 | 日本ゴア株式会社 | フッ素系弾性チューブ |
| HUE049309T2 (hu) * | 2009-11-04 | 2020-09-28 | Alcon Inc | Szilikon hidrogél lencse ojtott hidrofil bevonattal |
| TWI483996B (zh) * | 2009-12-08 | 2015-05-11 | Novartis Ag | 具有共價貼合塗層之聚矽氧水凝膠鏡片 |
| TWI599813B (zh) | 2010-07-30 | 2017-09-21 | 諾華公司 | 水合隱形鏡片 |
| WO2012109239A1 (en) * | 2011-02-07 | 2012-08-16 | The Trustees Of The University Of Pennsylvania | Multifunctional chitosan grafted surfaces and uses thereof |
| SG11201400228WA (en) | 2011-10-12 | 2014-05-29 | Novartis Ag | Method for making uv-absorbing ophthalmic lenses by coating |
| US9505184B2 (en) | 2011-11-15 | 2016-11-29 | Novartis Ag | Silicone hydrogel lens with a crosslinked hydrophilic coating |
| JP5834251B2 (ja) * | 2011-11-22 | 2015-12-16 | パナソニックＩｐマネジメント株式会社 | フレキシブル金属張基材、フレキシブル金属張基材の製造方法、プリント配線板、多層フレキシブルプリント配線板、及びフレックスリジッドプリント配線板 |
| WO2013188274A2 (en) | 2012-06-14 | 2013-12-19 | Novartis Ag | Azetidinium-containing copolymers and uses thereof |
| AU2013338051C1 (en) | 2012-10-29 | 2017-08-10 | Ariste Medical, Llc. | Polymer coating compositions and coated products |
| SG11201504592YA (en) | 2012-12-11 | 2015-07-30 | Novartis Ag | Method for applying a coating onto a silicone hydrogel lens |
| MY172901A (en) | 2012-12-17 | 2019-12-13 | Alcon Inc | Method for making improved uv-absorbing ophthalmic lenses |
| US11052177B2 (en) | 2013-09-06 | 2021-07-06 | The Trustees Of The University Of Pennsylvania | Antimicrobial polymer layers |
| WO2015054484A1 (en) * | 2013-10-09 | 2015-04-16 | The University Of Akron | Integrated zwitterionic conjugated polymers for bioelectronics, biosensing, regenerative medicine, and energy applications |
| US9708087B2 (en) | 2013-12-17 | 2017-07-18 | Novartis Ag | Silicone hydrogel lens with a crosslinked hydrophilic coating |
| AU2015249769A1 (en) | 2014-04-22 | 2016-11-10 | Ariste Medical, Llc. | Methods and processes for application of drug delivery polymeric coatings |
| BR112017003447B1 (pt) | 2014-08-26 | 2021-10-26 | Alcon Inc | Copolímero de poli(oxazolina-co-etilenoimina)-epicloridrina, material polimérico hidrofílico reticulável termicamente e solúvel em água, e métodos para produzir lentes de contato revestidas |
| US11002884B2 (en) | 2014-08-26 | 2021-05-11 | Alcon Inc. | Method for applying stable coating on silicone hydrogel contact lenses |
| US10723842B2 (en) | 2015-03-11 | 2020-07-28 | University Of Florida Research Foundation, Inc. | Mesh size control of lubrication in gemini hydrogels |
| JP6753041B2 (ja) * | 2015-08-27 | 2020-09-09 | 住友ゴム工業株式会社 | 表面改質金属及び金属表面の改質方法 |
| US9810812B2 (en) | 2015-09-04 | 2017-11-07 | Novartis Ag | Method for producing contact lenses with durable lubricious coatings thereon |
| MY186090A (en) | 2015-12-03 | 2021-06-21 | Alcon Inc | Contact lens packaging solutions |
| EP3391101B1 (en) | 2015-12-15 | 2020-07-08 | Alcon Inc. | Method for applying stable coating on silicone hydrogel contact lenses |
| EP3390026A1 (en) | 2015-12-15 | 2018-10-24 | Novartis AG | Method for producing contact lenses with a lubricious surface |
| US10718960B2 (en) | 2016-10-31 | 2020-07-21 | Alcon Inc. | Method for producing contact lenses with wearing comfort |
| EP3542193A1 (en) | 2016-11-18 | 2019-09-25 | Novartis AG | Method for making ophthalmic lenses |
| US10406972B2 (en) | 2017-02-24 | 2019-09-10 | Tesla, Inc. | Vehicle technologies for automated turn signaling |
| AU2018279285B2 (en) | 2017-06-07 | 2020-12-17 | Alcon Inc. | Silicone hydrogel contact lenses |
| EP4481478A3 (en) | 2017-06-07 | 2025-03-26 | Alcon Inc. | Silicone hydrogel contact lenses |
| US10809181B2 (en) | 2017-08-24 | 2020-10-20 | Alcon Inc. | Method and apparatus for determining a coefficient of friction at a test site on a surface of a contact lens |
| KR102735112B1 (ko) | 2017-12-13 | 2024-11-28 | 알콘 인코포레이티드 | 한 주 및 한 달 착용용 워터 그래디언트 콘택트 렌즈 |
| JP7564197B2 (ja) | 2019-11-04 | 2024-10-08 | アルコン インク． | 異なる柔軟性を有する表面を有するコンタクトレンズ |
| EP4369081B1 (en) | 2019-12-16 | 2025-06-25 | Alcon Inc. | Method for producing an ophthalmic product |
| US12358247B2 (en) | 2020-07-28 | 2025-07-15 | Alcon Inc. | Contact lenses with softer lens surfaces |
| WO2022224169A1 (en) | 2021-04-22 | 2022-10-27 | Alcon Inc. | Method for applying a coating onto a non-silicone hydrogel lens |
| US20240092043A1 (en) | 2022-08-17 | 2024-03-21 | Alcon Inc. | Contact lens with a hydrogel coating thereon |
| EP4658491A1 (en) | 2023-02-02 | 2025-12-10 | Alcon Inc. | Water gradient silicone hydrogel contact lenses |
| WO2024220971A1 (en) * | 2023-04-21 | 2024-10-24 | Azul 3D, Inc. | Optical lenses, optical components, and methods of manufacturing optical components |
Family Cites Families (25)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4588624A (en) * | 1982-05-14 | 1986-05-13 | Astra Meditec Ab | Articles exhibiting a biocompatible surface layer |
| US5258041A (en) * | 1982-09-29 | 1993-11-02 | Bio-Metric Systems, Inc. | Method of biomolecule attachment to hydrophobic surfaces |
| US4929685A (en) * | 1986-06-07 | 1990-05-29 | Nippon Oil And Fats Co., Ltd. | Method for modifying the surface of polycarbonate resin |
| US5080924A (en) * | 1989-04-24 | 1992-01-14 | Drexel University | Method of making biocompatible, surface modified materials |
| TW328535B (en) * | 1993-07-02 | 1998-03-21 | Novartis Ag | Functional photoinitiators and their manufacture |
| TW307775B (en) * | 1994-02-15 | 1997-06-11 | Novartis Erfind Verwalt Gmbh | Unsaturated carbohydrate derivatives, polymers thereof and their use |
| TW434456B (en) * | 1994-12-30 | 2001-05-16 | Novartis Ag | A compound as functionalized photoinitiator, its production process, its corresponding oligomers or polymers and its application in coating a substrate |
| ATE173742T1 (de) * | 1994-12-30 | 1998-12-15 | Novartis Ag | Polymere auf der grundlage von blockcopolymeren |
| TW353086B (en) * | 1994-12-30 | 1999-02-21 | Novartis Ag | Method for multistep coating of a surface |
| US6169127B1 (en) * | 1996-08-30 | 2001-01-02 | Novartis Ag | Plasma-induced polymer coatings |
| AR009439A1 (es) * | 1996-12-23 | 2000-04-12 | Novartis Ag | Un articulo que comprende un sustrato con un recubrimiento polimerico primario que porta grupos reactivos predominantemente en su superficie, unmetodo para preparar dicho articulo, un articulo que posee un recubrimiento de tipo hibrido y una lente de contacto |
| US6521358B1 (en) * | 1997-03-04 | 2003-02-18 | Matsushita Electric Industrial Co., Ltd. | Lead frame for semiconductor device and method of producing same |
| US6451871B1 (en) * | 1998-11-25 | 2002-09-17 | Novartis Ag | Methods of modifying surface characteristics |
| PL341346A1 (en) * | 1998-01-09 | 2001-04-09 | Novartis Ag | Polymeric coatings |
| TW473488B (en) * | 1998-04-30 | 2002-01-21 | Novartis Ag | Composite materials, biomedical articles formed thereof and process for their manufacture |
| WO2001002032A1 (en) * | 1999-06-30 | 2001-01-11 | Novartis Ag | Ophthalmic molding |
| EP1095966B1 (en) | 1999-10-27 | 2006-01-11 | Novartis AG | Process for the modification of a material surface |
| JP2001163932A (ja) * | 1999-10-27 | 2001-06-19 | Novartis Ag | 材料表面を改質する方法 |
| JP2001158813A (ja) * | 1999-10-27 | 2001-06-12 | Novartis Ag | 材料表面を被覆する方法 |
| EP1095711B1 (en) * | 1999-10-27 | 2004-01-28 | Novartis AG | Process for coating a material surface |
| MXPA02011857A (es) * | 2000-05-30 | 2003-04-10 | Novartis Ag | Articulos recubiertos. |
| US6589665B2 (en) * | 2000-05-30 | 2003-07-08 | Novartis Ag | Coated articles |
| US6428839B1 (en) * | 2000-06-02 | 2002-08-06 | Bausch & Lomb Incorporated | Surface treatment of medical device |
| JP4948740B2 (ja) * | 2000-08-24 | 2012-06-06 | ノバルティス アーゲー | 基材を表面改質する方法、及びそれから得られる改質された基材 |
| US6835410B2 (en) * | 2001-05-21 | 2004-12-28 | Novartis Ag | Bottle-brush type coatings with entangled hydrophilic polymer |
-
2002
- 2002-11-11 TW TW091133009A patent/TW200407367A/zh unknown
- 2002-11-12 AT AT02779553T patent/ATE378612T1/de not_active IP Right Cessation
- 2002-11-12 JP JP2003544501A patent/JP2005512115A/ja active Pending
- 2002-11-12 WO PCT/EP2002/012658 patent/WO2003042724A1/en not_active Ceased
- 2002-11-12 EP EP02779553A patent/EP1451615B1/en not_active Expired - Lifetime
- 2002-11-12 US US10/292,836 patent/US6878399B2/en not_active Expired - Fee Related
- 2002-11-12 CA CA002467092A patent/CA2467092A1/en not_active Abandoned
- 2002-11-12 DE DE60223589T patent/DE60223589T2/de not_active Expired - Lifetime
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE102018127812A1 (de) | 2018-11-07 | 2020-05-07 | Fachhochschule Kiel | Kontaktlinse mit einer Oberflächenbeschichtung und Herstellungsverfahren |
| WO2020094185A1 (de) | 2018-11-07 | 2020-05-14 | Fachhochschule Kiel | Kontaktlinse mit einer oberflächenbeschichtung und herstellungsverfahren |
| DE102018127812B4 (de) | 2018-11-07 | 2020-06-18 | Fachhochschule Kiel | Kontaktlinse mit einer Oberflächenbeschichtung und Herstellungsverfahren |
Also Published As
| Publication number | Publication date |
|---|---|
| EP1451615B1 (en) | 2007-11-14 |
| ATE378612T1 (de) | 2007-11-15 |
| TW200407367A (en) | 2004-05-16 |
| US20030219533A1 (en) | 2003-11-27 |
| CA2467092A1 (en) | 2003-05-22 |
| WO2003042724A1 (en) | 2003-05-22 |
| JP2005512115A (ja) | 2005-04-28 |
| EP1451615A1 (en) | 2004-09-01 |
| US6878399B2 (en) | 2005-04-12 |
| DE60223589D1 (de) | 2007-12-27 |
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| 8364 | No opposition during term of opposition |