CA2656681C - Biomimetic compounds and synthetic methods therefor - Google Patents
Biomimetic compounds and synthetic methods therefor Download PDFInfo
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- CA2656681C CA2656681C CA2656681A CA2656681A CA2656681C CA 2656681 C CA2656681 C CA 2656681C CA 2656681 A CA2656681 A CA 2656681A CA 2656681 A CA2656681 A CA 2656681A CA 2656681 C CA2656681 C CA 2656681C
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- Prior art keywords
- dhpd
- polymer
- dhpp
- adhesive
- pdma
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- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G69/00—Macromolecular compounds obtained by reactions forming a carboxylic amide link in the main chain of the macromolecule
- C08G69/40—Polyamides containing oxygen in the form of ether groups
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F8/00—Chemical modification by after-treatment
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
- C08G65/32—Polymers modified by chemical after-treatment
- C08G65/329—Polymers modified by chemical after-treatment with organic compounds
- C08G65/333—Polymers modified by chemical after-treatment with organic compounds containing nitrogen
- C08G65/33379—Polymers modified by chemical after-treatment with organic compounds containing nitrogen containing nitro group
- C08G65/33386—Polymers modified by chemical after-treatment with organic compounds containing nitrogen containing nitro group cyclic
- C08G65/33389—Polymers modified by chemical after-treatment with organic compounds containing nitrogen containing nitro group cyclic aromatic
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G71/00—Macromolecular compounds obtained by reactions forming a ureide or urethane link, otherwise, than from isocyanate radicals in the main chain of the macromolecule
- C08G71/04—Polyurethanes
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D5/00—Coating compositions, e.g. paints, varnishes or lacquers, characterised by their physical nature or the effects produced; Filling pastes
- C09D5/16—Antifouling paints; Underwater paints
- C09D5/1606—Antifouling paints; Underwater paints characterised by the anti-fouling agent
- C09D5/1637—Macromolecular compounds
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J171/00—Adhesives based on polyethers obtained by reactions forming an ether link in the main chain; Adhesives based on derivatives of such polymers
- C09J171/02—Polyalkylene oxides
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J175/00—Adhesives based on polyureas or polyurethanes; Adhesives based on derivatives of such polymers
- C09J175/04—Polyurethanes
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J201/00—Adhesives based on unspecified macromolecular compounds
- C09J201/02—Adhesives based on unspecified macromolecular compounds characterised by the presence of specified groups, e.g. terminal or pendant functional groups
- C09J201/06—Adhesives based on unspecified macromolecular compounds characterised by the presence of specified groups, e.g. terminal or pendant functional groups containing oxygen atoms
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| US82145906P | 2006-08-04 | 2006-08-04 | |
| US60/821,459 | 2006-08-04 | ||
| PCT/US2007/075299 WO2008019352A1 (en) | 2006-08-04 | 2007-08-06 | Biomimetic compounds and synthetic methods therefor |
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| CA2656681A1 CA2656681A1 (en) | 2008-02-14 |
| CA2656681C true CA2656681C (en) | 2014-04-22 |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB0100761D0 (en) | 2001-01-11 | 2001-02-21 | Biocompatibles Ltd | Drug delivery from stents |
| US7563454B1 (en) | 2003-05-01 | 2009-07-21 | Advanced Cardiovascular Systems, Inc. | Coatings for implantable medical devices |
| US8791171B2 (en) * | 2003-05-01 | 2014-07-29 | Abbott Cardiovascular Systems Inc. | Biodegradable coatings for implantable medical devices |
| EP2064251B1 (en) * | 2006-08-04 | 2017-10-25 | Kensey Nash Corporation | Biomimetic compounds and synthetic methods therefor |
| WO2008064058A2 (en) * | 2006-11-21 | 2008-05-29 | Abbott Laboratories | Use of a terpolymer of tetrafluoroethylene, hexafluoropropylene, and vinylidene fluoride in drug eluting coatings |
| US7713541B1 (en) | 2006-11-21 | 2010-05-11 | Abbott Cardiovascular Systems Inc. | Zwitterionic terpolymers, method of making and use on medical devices |
| US8951630B2 (en) | 2006-12-01 | 2015-02-10 | Rolex S.A. | Ultra-thin hydrophobic and oleophobic layer, method of manufacture and use in watchmaking as an epilame and in mechanical engineering as a barrier film |
| EP1927648A1 (fr) * | 2006-12-01 | 2008-06-04 | Rolex Sa | Couche ultra-mince hydrophobe et oléophobe, procédé de fabrication et utilisation en horlogerie comme épilame |
| US8383092B2 (en) | 2007-02-16 | 2013-02-26 | Knc Ner Acquisition Sub, Inc. | Bioadhesive constructs |
| US20080286332A1 (en) | 2007-05-14 | 2008-11-20 | Pacetti Stephen D | Implantable medical devices with a topcoat layer of phosphoryl choline acrylate polymer for reduced thrombosis, and improved mechanical properties |
| EP2167044A1 (en) * | 2007-06-11 | 2010-03-31 | BioCure, Inc. | Mucoadhesive vesicles for drug delivery |
| US8293867B2 (en) | 2007-11-09 | 2012-10-23 | Northwestern University | Substrate-independent layer-by-layer assembly using catechol-functionalized polymers |
| US8283384B2 (en) | 2008-01-24 | 2012-10-09 | University Of Utah Research Foundation | Adhesive complex coacervates and methods of making and using thereof |
| CN101978040A (zh) * | 2008-01-24 | 2011-02-16 | 犹他卅大学研究基金会 | 胶粘复合凝聚物及其制备和使用方法 |
| EP2130844A1 (en) * | 2008-06-06 | 2009-12-09 | Université de Liège | Multifunctional coatings |
| EP2334305B1 (en) * | 2008-09-26 | 2015-04-22 | Kensey Nash Corporation | Bioadhesive constructs |
| EP2348835A4 (en) * | 2008-09-28 | 2014-01-22 | Knc Ner Acquisition Sub Inc | MIXES FROM MULTICOLOR CATECHOL COMPOUNDS |
| WO2010042341A1 (en) * | 2008-09-29 | 2010-04-15 | Nerites Corporation | Delivery assembly, delivery tip, and method of using same |
| WO2010091300A1 (en) * | 2009-02-06 | 2010-08-12 | Nerites Corporation | Bioadhesive constructs with polymer blends |
| CA2751573C (en) * | 2009-02-06 | 2014-05-13 | Knc Ner Acquisition Sub, Inc. | Multi-linked star-shaped polymers and synthetic methods therfor |
| WO2010091298A1 (en) | 2009-02-06 | 2010-08-12 | Nerites Corporation | Multibranched bioadhesive compounds and synthetic methods therefor |
| WO2010114601A1 (en) * | 2009-04-02 | 2010-10-07 | Cornell University | Multiamino acid-based poly (ester amide)s |
| EP2453904A4 (en) | 2009-07-15 | 2014-11-26 | Kensey Nash Corp | THIN-LAYER COMPOSITIONS AND METHODS FOR THEIR SYNTHESIS AND USE |
| US8796394B2 (en) * | 2009-08-27 | 2014-08-05 | Northwestern University | Antifouling hydrogels, coatings, and methods of synthesis and use thereof |
| US20110130465A1 (en) * | 2009-12-01 | 2011-06-02 | Nerites Corporation | Coatings for prevention of biofilms |
| WO2011084710A1 (en) * | 2009-12-17 | 2011-07-14 | The University Of Chicago | Methods of making self-healing polymer and gel compositions |
| JP5604154B2 (ja) * | 2010-04-02 | 2014-10-08 | 株式会社メニコン | ポリマー材料、眼用レンズ及びコンタクトレンズ |
| CA2799818A1 (en) | 2010-05-24 | 2011-12-01 | University Of Utah Research Foundation | Reinforced adhesive complex coacervates and methods of making and using thereof |
| US9045651B2 (en) * | 2010-06-22 | 2015-06-02 | University Of Florida Research Foundation, Inc. | Antifouling surfaces, methods of manufacture thereof and articles comprising the same |
| WO2012009664A2 (en) * | 2010-07-16 | 2012-01-19 | Knc Ner Acquisition Sub, Inc. | Bioadhesive compounds and methods of synthesis and use |
| WO2012064821A2 (en) | 2010-11-09 | 2012-05-18 | Knc Ner Acquisition Sub, Inc. | Adhesive compounds and methods use for hernia repair |
| EP2637708A2 (en) | 2010-11-12 | 2013-09-18 | University of Utah Research Foundation | Simple adhesive coacervates and methods of making and using thereof |
| KR101685646B1 (ko) * | 2010-12-29 | 2016-12-13 | 한화케미칼 주식회사 | 홍합 접착단백질 모방을 통한 나노입자를 수계 매질에 분산시키는 생체적합성 분산 안정화제 |
| US8784895B2 (en) | 2011-03-15 | 2014-07-22 | Northwestern University | Multifunctional metal nanoparticles having a polydopamine-based surface and methods of making and using the same |
| EP2798027A4 (en) | 2011-11-28 | 2015-10-07 | Boxin Zhao | METHOD AND APPARATUS FOR COLLAGE ASSEMBLY IN AQUEOUS MEDIUM |
| WO2013142028A1 (en) * | 2012-03-23 | 2013-09-26 | California Institute Of Technology | Rapidly crosslinkable adhesives for biomedical applications |
| US8907045B2 (en) | 2012-04-03 | 2014-12-09 | Empire Technology Development Llc | Biocompatible adhesive polymers |
| WO2014018771A1 (en) * | 2012-07-25 | 2014-01-30 | Knc Ner Acquisition Sub, Inc. | Mono-layer thin film adhesive compounds |
| WO2014123665A1 (en) | 2013-02-06 | 2014-08-14 | Kci Licensing, Inc. | Polymers, preparation and use thereof |
| WO2014152918A1 (en) * | 2013-03-14 | 2014-09-25 | Safewhite Llc | Methods and materials for providing teeth with a white appearance |
| MX363474B (es) | 2013-03-15 | 2019-03-25 | Baxter Int | Inmovilizacion de un agente activo en un sustrato. |
| EP2784101A1 (en) | 2013-03-28 | 2014-10-01 | Nitto Europe N.V | Hydroxyphenyl functionalized poly(ester amide) |
| CN104073114B (zh) * | 2013-03-29 | 2016-04-13 | 中国科学院兰州化学物理研究所 | 一种具有防海洋生物污染功能表面材料的制备方法 |
| WO2014197768A1 (en) | 2013-06-07 | 2014-12-11 | Baxter International Inc. | Immobilization of an active agent on a substrate using compounds including trihydroxyphenyl groups |
| EP3019207A4 (en) * | 2013-07-10 | 2017-03-15 | President and Fellows of Harvard College | Modification of surfaces for fluid and solid repellency |
| US10077378B2 (en) | 2013-11-18 | 2018-09-18 | Clemson University | Self-repairing polyurethane networks |
| US10079387B2 (en) * | 2014-02-26 | 2018-09-18 | The Regents Of The University Of California | Electrical conductive polymer binder for Si alloy materials |
| WO2015129846A1 (ja) * | 2014-02-28 | 2015-09-03 | 独立行政法人科学技術振興機構 | カテコールセグメントを含むブロック共重合体及び該ブロック共重合体で被覆された無機ナノ粒子、並びに、カテコールセグメントを含むブロック共重合体の製造方法及び該ブロック共重合体で被覆された無機ナノ粒子の製造方法 |
| EP3127970B1 (en) * | 2014-03-31 | 2019-08-07 | National Institute for Materials Science | Nano-coating material, method for manufacturing same, coating agent, functional material, and method for manufacturing same |
| WO2015172073A1 (en) * | 2014-05-08 | 2015-11-12 | Cornell University | Bio-adhesive gels and methods of use |
| WO2015175665A1 (en) * | 2014-05-13 | 2015-11-19 | Dsm Ip Assets B.V. | Bioadhesive compounds and methods of synthesis and use |
| KR101791241B1 (ko) * | 2014-06-17 | 2017-10-30 | 한국과학기술원 | 카테콜 아민 기반의 다기능성 필름 및 이의 제조 방법 |
| JP6742297B2 (ja) | 2014-07-14 | 2020-08-19 | ユニヴァーシティ オブ ユタ リサーチ ファンデーション | その場凝固複合コアセルベートならびにその製造および使用方法 |
| EP3171880A4 (en) * | 2014-07-22 | 2017-12-13 | The University of Akron | Degradable amino acid-based poly(ester urea) copolymer adhesives |
| EP3191559B1 (en) | 2014-09-11 | 2018-10-31 | SuSoS AG | Functional polymer |
| SG11201702534VA (en) | 2014-09-30 | 2017-05-30 | Luxembourg Inst Of Science And Technology | Plasma deposition method for catechol/quinone functionalised layers |
| CN107106732A (zh) * | 2014-10-14 | 2017-08-29 | 新加坡科技研究局 | 抗细菌和/或防污聚合物 |
| KR101759998B1 (ko) * | 2014-11-11 | 2017-07-20 | 한국에너지기술연구원 | 카테콜 그룹을 갖는 이온교환고분자, 이의 제조방법 및 응용 |
| DE102014226098A1 (de) * | 2014-12-16 | 2016-06-16 | Fraunhofer-Gesellschaft zur Förderung der angewandten Forschung e.V. | Mehrkomponentenklebstoff zur Herstellung eines Adhäsivhydrogels |
| CN107207696B (zh) * | 2015-01-02 | 2023-05-23 | 耶路撒冷希伯来大学伊森姆研究发展有限公司 | 可生物降解的聚合物 |
| US10611927B2 (en) | 2015-05-26 | 2020-04-07 | Japan Science And Technology Agency | Catechol-containing adhesive hydrogel, composition for preparing adhesive hydrogel, and compositions each including said adhesive hydrogel |
| US10087344B2 (en) | 2015-10-30 | 2018-10-02 | E Ink Corporation | Methods for sealing microcell containers with phenethylamine mixtures |
| TW201716515A (zh) * | 2015-11-04 | 2017-05-16 | 鴻海精密工業股份有限公司 | 著色材料、著色膜及其製備方法、眼用鏡片 |
| CN106674420A (zh) * | 2015-11-05 | 2017-05-17 | 鸿富锦精密工业（深圳）有限公司 | 着色材料、着色膜及其制备方法、眼用镜片 |
| US11478178B2 (en) * | 2015-12-08 | 2022-10-25 | Carnegie Mellon University | Electronic structures on swollen hydrogels |
| WO2018025828A1 (ja) * | 2016-08-05 | 2018-02-08 | 国立研究開発法人科学技術振興機構 | ブロック共重合体、多層構造体、固体高分子膜、燃料電池、多層構造体の製造方法、及び無機ナノ粒子を含む多層構造体の製造方法 |
| US11286231B2 (en) * | 2016-10-26 | 2022-03-29 | Wake Forest University Health Sciences | Hydrogen-bonding compounds, compositions comprising the same, and methods of preparing and using the same |
| RU2745513C2 (ru) * | 2016-12-26 | 2021-03-25 | Акцо Нобель Коатингс Интернэшнл Б.В. | Система кроющей композиции, способ ее получения и ее применение |
| US10912859B2 (en) | 2017-03-08 | 2021-02-09 | Baxter International Inc. | Additive able to provide underwater adhesion |
| US11202848B2 (en) | 2017-03-08 | 2021-12-21 | Baxter International Inc. | Surgical adhesive able to glue in wet conditions |
| JPWO2018221564A1 (ja) * | 2017-05-31 | 2020-04-23 | 日立化成株式会社 | 接着剤及び構造体 |
| WO2019018664A1 (en) * | 2017-07-19 | 2019-01-24 | Dentsply Sirona Inc. | HYDROSOLUBLE HYDROGEL BASED DENTAL COMPOSITION AND METHODS OF MAKING AND USING SAME |
| KR101823054B1 (ko) | 2017-07-27 | 2018-01-30 | 주식회사 메디코젬 | 폴리갈산 중합체를 포함하는 생체접착제용 첨가제 조성물 |
| US11255810B2 (en) * | 2017-09-14 | 2022-02-22 | Siemens Healthcare Diagnostics Inc. | Adhesive-polymer containing membranes for in vitro diagnostic devices |
| US11629329B2 (en) | 2017-10-11 | 2023-04-18 | Wake Forest University Health Sciences | Bioink compositions and methods of preparing and using the same |
| US11130886B2 (en) * | 2017-12-31 | 2021-09-28 | Purdue Research Foundation | Adhesives |
| US11896234B2 (en) | 2018-01-26 | 2024-02-13 | Fluidx Medical Technology, Llc | Apparatus and method of using in situ solidifying complex coacervates for vascular occlusion |
| JP2019183078A (ja) * | 2018-04-17 | 2019-10-24 | 日立化成株式会社 | 粘着剤 |
| CN108484825B (zh) * | 2018-05-08 | 2020-05-26 | 济南大学 | 可逆光控疏水性偶氮苯类含氟共聚物及其膜制备方法 |
| WO2019246123A1 (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 |
| WO2020077282A1 (en) | 2018-10-12 | 2020-04-16 | L'oreal | Responsive coatings for hair fibers |
| WO2020195977A1 (ja) * | 2019-03-22 | 2020-10-01 | 国立研究開発法人物質・材料研究機構 | 複合体、無人航空機、複合体の製造方法、及び、構造体 |
| EP4045002A1 (en) | 2019-10-17 | 2022-08-24 | L'oreal | Compositions, systems and methods for conferring durable shaping of keratinous fibers |
| CN111138580B (zh) * | 2019-12-31 | 2022-04-26 | 江汉大学 | 末端含二硫代酯的pvp化合物、拓扑聚合物及其制备方法 |
| US11753567B2 (en) | 2020-01-08 | 2023-09-12 | Nano And Advanced Materials Institute Limited | Adhesive material with improved bonding performance to a wet substrate and methods for preparing the same |
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| US11643574B2 (en) | 2021-05-28 | 2023-05-09 | Cohesys Inc. | Adhesive devices and uses thereof |
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| CN114796595A (zh) * | 2022-04-13 | 2022-07-29 | 重庆医科大学 | 一种伤口敷料的制备方法、伤口敷料及应用 |
Family Cites Families (118)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2439769A1 (fr) * | 1978-10-26 | 1980-05-23 | Oreal | N-(dihydroxy-2,5 trimethyl-3,4,6) benzyl acrylamide et methacrylamide, leur procede de preparation et leur utilisation pour la realisation de polymeres antioxydants |
| US5225196A (en) | 1983-11-14 | 1993-07-06 | Columbia Laboratories, Inc. | Bioadhesive compositions and methods of treatment therewith |
| US4795436A (en) | 1983-11-14 | 1989-01-03 | Bio-Mimetics, Inc. | Bioadhesive composition and method of treatment therewith |
| US4983392A (en) | 1983-11-14 | 1991-01-08 | Bio-Mimetics, Inc. | Bioadhesive compositions and methods of treatment therewith |
| EP0501523B1 (en) | 1983-11-14 | 1997-04-09 | Columbia Laboratories, Inc. | Bioadhesive compositions |
| US4808702A (en) | 1984-03-07 | 1989-02-28 | Waite J Herbert | Decapeptides produced from bioadhesive polyphenolic proteins |
| US4687740A (en) | 1984-03-07 | 1987-08-18 | University Of Connecticut Research & Development Corp. | Decapeptides produced from bioadhesive polyphenolic proteins |
| US4496397A (en) | 1984-03-07 | 1985-01-29 | University Of Connecticut | Process for purifying and stabilizing catechol-containing proteins and materials obtained thereby |
| US4585585A (en) | 1984-03-07 | 1986-04-29 | University Of Connecticut Research & Development Corporation | Decapeptides produced from bioadhesive polyphenolic proteins |
| US6309669B1 (en) | 1984-03-16 | 2001-10-30 | The United States Of America As Represented By The Secretary Of The Army | Therapeutic treatment and prevention of infections with a bioactive materials encapsulated within a biodegradable-biocompatible polymeric matrix |
| US5202256A (en) | 1984-09-13 | 1993-04-13 | Enzon Labs, Inc. | Bioadhesive precursor protein expression vectors |
| US5202236A (en) | 1984-09-13 | 1993-04-13 | Enzon Labs Inc. | Method of producing bioadhesive protein |
| US5242808A (en) | 1984-09-13 | 1993-09-07 | Enzon, Inc. | Production of bioadhesive precursor protein analogs by genetically engineered organisms |
| US5049504A (en) | 1986-11-24 | 1991-09-17 | Genex Corporation | Bioadhesive coding sequences |
| JPS6323670A (ja) | 1986-04-25 | 1988-01-30 | バイオ−ポリマ−ズ インコ−ポレ−テツド | 接着・被覆組成物とその使用方法 |
| US5108923A (en) | 1986-04-25 | 1992-04-28 | Collaborative Research, Inc. | Bioadhesives for cell and tissue adhesion |
| US5030230A (en) | 1986-05-16 | 1991-07-09 | Great Plains Eye Clinic, Ltd. | Corneal implant |
| US5260194A (en) | 1986-09-05 | 1993-11-09 | Syntex (U.S.A.) Inc. | Immunoseparating strip |
| JPH0665280B2 (ja) | 1987-03-04 | 1994-08-24 | 味の素株式会社 | タンパクゲル化剤及びそれを用いるタンパクのゲル化方法 |
| US4978336A (en) | 1987-09-29 | 1990-12-18 | Hemaedics, Inc. | Biological syringe system |
| US5487739A (en) | 1987-11-17 | 1996-01-30 | Brown University Research Foundation | Implantable therapy systems and methods |
| US5192316A (en) | 1988-02-16 | 1993-03-09 | Allergan, Inc. | Ocular device |
| US5024933A (en) | 1988-05-10 | 1991-06-18 | Enzo Biochem, Inc. | Method and kit for sample adherence to test substrate |
| US4908404A (en) | 1988-08-22 | 1990-03-13 | Biopolymers, Inc. | Synthetic amino acid-and/or peptide-containing graft copolymers |
| US5410023A (en) | 1989-06-27 | 1995-04-25 | Burzio; Luis O. | Peptide useful as adhesive, and process for the preparation thereof |
| US5574134A (en) | 1989-07-11 | 1996-11-12 | University Of Delaware | Polypeptide monomers, linearly extended and/or crosslinked forms thereof, and applications thereof |
| US5098999A (en) | 1989-08-23 | 1992-03-24 | Hitachi Chemical Company | Amino-protected dopa derivative and production thereof |
| US5116315A (en) | 1989-10-03 | 1992-05-26 | Hemaedics, Inc. | Biological syringe system |
| JPH03294292A (ja) * | 1990-04-11 | 1991-12-25 | O Brugio Louis | 接着剤として有用なペプチドおよびその製造方法 |
| US5197973A (en) | 1990-12-14 | 1993-03-30 | Creative Biomolecules, Inc. | Synthetic bioadhesive |
| DK0585368T3 (da) | 1991-04-25 | 1998-03-16 | Univ Brown Res Found | Implanterbart biokompatibelt immunisolatorisk vehikel til afgivelse af udvalgte terapeutiske produkter |
| US5605938A (en) | 1991-05-31 | 1997-02-25 | Gliatech, Inc. | Methods and compositions for inhibition of cell invasion and fibrosis using dextran sulfate |
| US5705178A (en) | 1991-05-31 | 1998-01-06 | Gliatech, Inc. | Methods and compositions based on inhibition of cell invasion and fibrosis by anionic polymers |
| US6235313B1 (en) | 1992-04-24 | 2001-05-22 | Brown University Research Foundation | Bioadhesive microspheres and their use as drug delivery and imaging systems |
| JPH07507682A (ja) | 1992-05-07 | 1995-08-31 | アクティノバ・リミテッド | Ｌプロテインに由来する免疫グロブリン結合性タンパク質およびその用途 |
| DK145092D0 (US08030413-20111004-C00045.png) | 1992-12-03 | 1992-12-03 | Novo Nordisk As | |
| CA2154444A1 (en) | 1993-01-21 | 1994-08-04 | John F. W. Keana | Chemical functionalization of surfaces |
| EP0615745B1 (en) | 1993-02-19 | 1997-05-02 | Howard Green | Compositions containing corneocyte proteins |
| US5549904A (en) | 1993-06-03 | 1996-08-27 | Orthogene, Inc. | Biological adhesive composition and method of promoting adhesion between tissue surfaces |
| US5939385A (en) | 1993-08-13 | 1999-08-17 | Zymogenetics, Inc. | Transglutaminase cross-linkable polypeptides and methods relating thereto |
| US5428014A (en) | 1993-08-13 | 1995-06-27 | Zymogenetics, Inc. | Transglutaminase cross-linkable polypeptides and methods relating thereto |
| US5520727A (en) | 1993-08-16 | 1996-05-28 | The Regents Of University Of California | Aqueous algal-based phenolic type adhesives and glues |
| FR2715309B1 (fr) | 1994-01-24 | 1996-08-02 | Imedex | Composition adhésive, à usage chirurgical, à base de collagène modifié par coupure oxydative et non réticulé. |
| CN1145080A (zh) | 1994-03-04 | 1997-03-12 | 华盛顿大学 | 嵌段和接枝共聚物及与其有关的方法 |
| DE4409217A1 (de) | 1994-03-18 | 1996-02-15 | Zirm Matthias Univ Prof Dr | Künstliche Linse |
| US5582955A (en) | 1994-06-23 | 1996-12-10 | State Of Oregon Acting By And Through The State Board Of Higher Education On Behalf Of The University Of Oregon | Chemical functionalization of surfaces |
| US5935849A (en) | 1994-07-20 | 1999-08-10 | Cytotherapeutics, Inc. | Methods and compositions of growth control for cells encapsulated within bioartificial organs |
| US5840576A (en) | 1994-07-20 | 1998-11-24 | Cytotherapeutics, Inc. | Methods and compositions of growth control for cells encapsulated within bioartificial organs |
| US6322996B1 (en) | 1994-08-23 | 2001-11-27 | Drug Delivery System Institute, Ltd. | Protein modification method |
| US5490980A (en) | 1994-09-28 | 1996-02-13 | Chesebrough-Pond's Usa Co., Division Of Conopco, Inc. | Covalent bonding of active agents to skin, hair or nails |
| US6010871A (en) | 1994-09-29 | 2000-01-04 | Ajinomoto Co., Inc. | Modification of peptide and protein |
| JP3567007B2 (ja) * | 1995-02-08 | 2004-09-15 | 大阪市 | 含フッ素フェノール樹脂組成物 |
| US5817470A (en) | 1995-03-10 | 1998-10-06 | Sociedad Biotecnologica Collico Limitada | Immobilization of antigens to solid support by the mussel adhesive polyphenolic protein and the method for use therein |
| US6129761A (en) | 1995-06-07 | 2000-10-10 | Reprogenesis, Inc. | Injectable hydrogel compositions |
| US5830539A (en) | 1995-11-17 | 1998-11-03 | The State Of Oregon Acting By And Through The State Board Of Higher Education On Behalf Of The University Of Oregon | Methods for functionalizing and coating substrates and devices made according to the methods |
| US6833408B2 (en) | 1995-12-18 | 2004-12-21 | Cohesion Technologies, Inc. | Methods for tissue repair using adhesive materials |
| US5985312A (en) | 1996-01-26 | 1999-11-16 | Brown University Research Foundation | Methods and compositions for enhancing the bioadhesive properties of polymers |
| US6368586B1 (en) | 1996-01-26 | 2002-04-09 | Brown University Research Foundation | Methods and compositions for enhancing the bioadhesive properties of polymers |
| US5834232A (en) | 1996-05-01 | 1998-11-10 | Zymogenetics, Inc. | Cross-linked gelatin gels and methods of making them |
| US5955096A (en) | 1996-06-25 | 1999-09-21 | Brown University Research Foundation | Methods and compositions for enhancing the bioadhesive properties of polymers using organic excipients |
| US6491903B1 (en) | 1996-06-27 | 2002-12-10 | Washington University | Particles comprising amphiphilic copolymers |
| JP3407599B2 (ja) | 1996-07-01 | 2003-05-19 | 味の素株式会社 | 接着用酵素製剤及び接着食品の製造法 |
| US6284267B1 (en) | 1996-08-14 | 2001-09-04 | Nutrimed Biotech | Amphiphilic materials and liposome formulations thereof |
| US7009034B2 (en) | 1996-09-23 | 2006-03-07 | Incept, Llc | Biocompatible crosslinked polymers |
| DE19643007A1 (de) | 1996-10-18 | 1998-04-23 | Martin Dr Schaerfe | Haftvermittler oder Klebstoff mit Aminosäureanteil |
| US6022597A (en) | 1996-11-08 | 2000-02-08 | Yan; Mingdi | Chemical functionalization of surfaces |
| US6126903A (en) | 1996-11-15 | 2000-10-03 | Biochem Immunosystems, Inc. | Blood cell analyzer with tube holder and cap piercer |
| US6039901A (en) | 1997-01-31 | 2000-03-21 | Givaudan Roure Flavors Corporation | Enzymatically protein encapsulating oil particles by complex coacervation |
| WO1998043686A1 (en) | 1997-04-03 | 1998-10-08 | California Institute Of Technology | Enzyme-mediated modification of fibrin for tissue engineering |
| ES2210761T3 (es) | 1997-05-21 | 2004-07-01 | The Board Of Trustees Of The Leland Stanford Junior University | Composicion y procedimiento para mejorar el transporte a traves de las membranas biologicas. |
| US6150461A (en) | 1997-05-27 | 2000-11-21 | Hisamitsu Pharmaceutical Co., Inc. | Carriers targettable to organ |
| JP3981525B2 (ja) | 1998-01-20 | 2007-09-26 | ハワード・グリーン | 組織への物質のトランスグルタミナーゼ連結 |
| JP3936058B2 (ja) | 1998-03-12 | 2007-06-27 | 株式会社メニコン | コンタクトレンズ用液剤 |
| US6506577B1 (en) | 1998-03-19 | 2003-01-14 | The Regents Of The University Of California | Synthesis and crosslinking of catechol containing copolypeptides |
| DK1334116T3 (da) | 1998-09-28 | 2007-09-17 | Bio Polymer Products Of Sweden | En fremgangsmåde til fremstilling af polyphenoliske adhæsive proteiner |
| CA2351734A1 (en) | 1998-11-20 | 2000-06-02 | University Of Connecticut | Generic integrated implantable potentiostat telemetry unit for electrochemical sensors |
| US20030099682A1 (en) | 1998-11-20 | 2003-05-29 | Francis Moussy | Apparatus and method for control of tissue/implant interactions |
| JP2002531217A (ja) | 1998-12-04 | 2002-09-24 | チャンドラシェカー ピー． パサック， | 生体適合性架橋ポリマー |
| US6329485B1 (en) | 1998-12-11 | 2001-12-11 | Bausch & Lomb Incorporated | High refractive index hydrogel compositions for ophthalmic implants |
| JP2000281699A (ja) * | 1999-01-07 | 2000-10-10 | Ueda Seni Kagaku Shinkokai | 生体適合性の良好な接着タンパク質およびそのアミノ酸配列 |
| US6294187B1 (en) | 1999-02-23 | 2001-09-25 | Osteotech, Inc. | Load-bearing osteoimplant, method for its manufacture and method of repairing bone using same |
| US6696073B2 (en) | 1999-02-23 | 2004-02-24 | Osteotech, Inc. | Shaped load-bearing osteoimplant and methods of making same |
| WO2000055181A1 (en) | 1999-03-15 | 2000-09-21 | The General Hospital Corporation | Methods of modulating cell attachment and migration |
| US6663883B1 (en) | 1999-08-26 | 2003-12-16 | Takeda Chemical Industries, Ltd. | Matrix adhering to nasal mucosa |
| US20010049400A1 (en) | 1999-10-25 | 2001-12-06 | Azaam Alli | Method of making an optical polymer |
| DK1589088T3 (da) | 1999-12-17 | 2007-12-03 | Biopolymer Products Of Sweden | Ny bioklæbende sammensætning, som omfatter et bioklæbende polyphenolisk protein, en polymer, der omfatter kulhydratgrupper, og farmaceutisk acceptable tynde filamenter, samt anvendelser deraf |
| WO2001060837A2 (en) | 2000-02-16 | 2001-08-23 | Northwestern University | Polypeptoid pulmonary surfactants |
| JP2001329183A (ja) | 2000-05-22 | 2001-11-27 | Yuichi Mori | ゲル化性組成物 |
| US6565960B2 (en) | 2000-06-01 | 2003-05-20 | Shriners Hospital Of Children | Polymer composite compositions |
| AU2001283492A1 (en) | 2000-07-11 | 2002-01-21 | The Johns Hopkins University School Of Medicine | Methods of patterning protein and cell adhesivity |
| US9387094B2 (en) | 2000-07-19 | 2016-07-12 | Warsaw Orthopedic, Inc. | Osteoimplant and method of making same |
| AR030341A1 (es) | 2000-08-14 | 2003-08-20 | Novartis Ag | Articulos biomedicos moldeados |
| DK1328300T3 (da) | 2000-10-23 | 2005-03-21 | Tissuemed Ltd | Selvklæbende hydratiserbar matrix til topisk terapeutisk anvendelse |
| US6635274B1 (en) | 2000-10-27 | 2003-10-21 | Biochemics, Inc. | Solution-based transdermal drug delivery system |
| US20020132074A1 (en) | 2001-01-30 | 2002-09-19 | Gervasi David J. | Chlorofluoro elastomer compositions for use in electrophotoraphic fusing applications |
| AU2002350088A1 (en) * | 2001-06-22 | 2003-01-08 | Millard Marsden Mershon | Compositions and methods for reducing blood and fluid loss from open wounds |
| US8815793B2 (en) * | 2001-07-20 | 2014-08-26 | Northwestern University | Polymeric compositions and related methods of use |
| WO2003008376A2 (en) * | 2001-07-20 | 2003-01-30 | Northwestern University | Adhesive dopa-containing polymers and related methods of use |
| US7858679B2 (en) * | 2001-07-20 | 2010-12-28 | Northwestern University | Polymeric compositions and related methods of use |
| GB0123232D0 (en) | 2001-09-26 | 2001-11-21 | Smith & Nephew | Polymers |
| AU2003216019A1 (en) | 2002-03-26 | 2003-10-08 | Magnus Qvist | Method for attaching two surfaces to each other using a bioadhesive polyphenolic protein and periodate ions. |
| US7300991B2 (en) * | 2002-03-27 | 2007-11-27 | Hitachi, Ltd. | Cationic conductor, its intermediate, and lithium secondary battery using the conductor |
| US6872439B2 (en) | 2002-05-13 | 2005-03-29 | The Regents Of The University Of California | Adhesive microstructure and method of forming same |
| GB0216780D0 (en) | 2002-07-19 | 2002-08-28 | Bradford Particle Design Ltd | Methods of particle formation |
| US7208171B2 (en) | 2002-10-31 | 2007-04-24 | Northwestern University | Injectable and bioadhesive polymeric hydrogels as well as related methods of enzymatic preparation |
| WO2005033198A1 (en) | 2003-10-07 | 2005-04-14 | Coloplast A/S | A composition useful as an adhesive and use of such a composition |
| EP1697481A2 (en) * | 2003-12-09 | 2006-09-06 | Spherics, Inc. | Bioadhesive polymers with catechol functionality |
| US7033511B2 (en) * | 2004-01-20 | 2006-04-25 | A-Dec, Inc. | Sustained water treatment in dental equipment |
| DE102004004214A1 (de) * | 2004-01-27 | 2005-08-25 | Basf Ag | Polymerdispersionen oder -lösungen mit 3,4 Dihydroxyphenylgruppen |
| EP1735456A4 (en) * | 2004-02-27 | 2011-11-16 | Univ Northwestern | POYLMERIC COMPOSITIONS AND ASSOCIATED METHODS OF USE |
| US8685431B2 (en) | 2004-03-16 | 2014-04-01 | Advanced Cardiovascular Systems, Inc. | Biologically absorbable coatings for implantable devices based on copolymers having ester bonds and methods for fabricating the same |
| WO2007016622A2 (en) | 2005-08-02 | 2007-02-08 | Wright Medical Technolody, Inc. | Gel composition for inhibiting cellular adhesion |
| US7732539B2 (en) | 2006-02-16 | 2010-06-08 | National Science Foundation | Modified acrylic block copolymers for hydrogels and pressure sensitive wet adhesives |
| WO2007127225A2 (en) * | 2006-04-25 | 2007-11-08 | Purdue Research Foundation | Cross-linkable polymeric compositions |
| EP2064251B1 (en) * | 2006-08-04 | 2017-10-25 | Kensey Nash Corporation | Biomimetic compounds and synthetic methods therefor |
| US8673286B2 (en) | 2007-04-09 | 2014-03-18 | Northwestern University | DOPA-functionalized, branched, poly(aklylene oxide) adhesives |
| US7927620B2 (en) | 2007-05-15 | 2011-04-19 | Boston Scientific Scimed, Inc. | Medical devices having antifouling character |
| WO2010091300A1 (en) | 2009-02-06 | 2010-08-12 | Nerites Corporation | Bioadhesive constructs with polymer blends |
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2007
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- 2007-08-06 JP JP2009523083A patent/JP5597836B2/ja not_active Expired - Fee Related
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| EP2064251A1 (en) | 2009-06-03 |
| WO2008019352A1 (en) | 2008-02-14 |
| US7622533B2 (en) | 2009-11-24 |
| US8575276B2 (en) | 2013-11-05 |
| JP5597836B2 (ja) | 2014-10-01 |
| AU2007283772A1 (en) | 2008-02-14 |
| US20100197868A1 (en) | 2010-08-05 |
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