ZA200406448B - Polymer coating for medical devices - Google Patents
Polymer coating for medical devices Download PDFInfo
- Publication number
- ZA200406448B ZA200406448B ZA200406448A ZA200406448A ZA200406448B ZA 200406448 B ZA200406448 B ZA 200406448B ZA 200406448 A ZA200406448 A ZA 200406448A ZA 200406448 A ZA200406448 A ZA 200406448A ZA 200406448 B ZA200406448 B ZA 200406448B
- Authority
- ZA
- South Africa
- Prior art keywords
- poly
- lactide
- polymer
- coating
- layer
- Prior art date
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- 229920000642 polymer Polymers 0.000 title claims description 316
- 238000000576 coating method Methods 0.000 title claims description 102
- 239000011248 coating agent Substances 0.000 title claims description 87
- 239000013543 active substance Substances 0.000 claims description 184
- -1 poly(L-lactide) Polymers 0.000 claims description 142
- 229910052751 metal Inorganic materials 0.000 claims description 120
- 239000002184 metal Substances 0.000 claims description 119
- 150000002596 lactones Chemical class 0.000 claims description 106
- 238000000034 method Methods 0.000 claims description 77
- 239000002904 solvent Substances 0.000 claims description 65
- 229920001432 poly(L-lactide) Polymers 0.000 claims description 58
- 229920001244 Poly(D,L-lactide) Polymers 0.000 claims description 52
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 claims description 48
- 229910000077 silane Inorganic materials 0.000 claims description 46
- 229920001577 copolymer Polymers 0.000 claims description 39
- 125000001072 heteroaryl group Chemical group 0.000 claims description 36
- 230000003213 activating effect Effects 0.000 claims description 35
- 125000000524 functional group Chemical group 0.000 claims description 32
- 125000001424 substituent group Chemical group 0.000 claims description 32
- 150000001875 compounds Chemical class 0.000 claims description 31
- 239000003054 catalyst Substances 0.000 claims description 27
- 229920001400 block copolymer Polymers 0.000 claims description 24
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 22
- 239000000178 monomer Substances 0.000 claims description 22
- 125000003277 amino group Chemical group 0.000 claims description 21
- 238000011065 in-situ storage Methods 0.000 claims description 21
- 150000004756 silanes Chemical class 0.000 claims description 21
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- 229920000728 polyester Polymers 0.000 claims description 18
- 239000003153 chemical reaction reagent Substances 0.000 claims description 16
- 238000000151 deposition Methods 0.000 claims description 16
- 229920001519 homopolymer Polymers 0.000 claims description 16
- 238000007151 ring opening polymerisation reaction Methods 0.000 claims description 14
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 14
- AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Polymers OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 claims description 12
- UREBDLICKHMUKA-CXSFZGCWSA-N dexamethasone Chemical compound C1CC2=CC(=O)C=C[C@]2(C)[C@]2(F)[C@@H]1[C@@H]1C[C@@H](C)[C@@](C(=O)CO)(O)[C@@]1(C)C[C@@H]2O UREBDLICKHMUKA-CXSFZGCWSA-N 0.000 claims description 12
- 229960003957 dexamethasone Drugs 0.000 claims description 12
- 229920006301 statistical copolymer Polymers 0.000 claims description 12
- 229920000954 Polyglycolide Polymers 0.000 claims description 11
- 229920001434 poly(D-lactide) Polymers 0.000 claims description 11
- 125000004104 aryloxy group Chemical group 0.000 claims description 10
- 229920001306 poly(lactide-co-caprolactone) Polymers 0.000 claims description 10
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 10
- 102000000578 Cyclin-Dependent Kinase Inhibitor p21 Human genes 0.000 claims description 9
- 108010016788 Cyclin-Dependent Kinase Inhibitor p21 Proteins 0.000 claims description 9
- 229920002463 poly(p-dioxanone) polymer Polymers 0.000 claims description 9
- 230000001028 anti-proliverative effect Effects 0.000 claims description 8
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- 210000001124 body fluid Anatomy 0.000 claims description 6
- 239000010839 body fluid Substances 0.000 claims description 6
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims description 6
- 238000005507 spraying Methods 0.000 claims description 6
- 125000005415 substituted alkoxy group Chemical group 0.000 claims description 6
- 125000005017 substituted alkenyl group Chemical group 0.000 claims description 5
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- 229920000058 polyacrylate Polymers 0.000 claims description 3
- 229920000193 polymethacrylate Polymers 0.000 claims description 3
- 125000004469 siloxy group Chemical group [SiH3]O* 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 241000124008 Mammalia Species 0.000 claims 3
- 125000001475 halogen functional group Chemical group 0.000 claims 1
- 229920000233 poly(alkylene oxides) Polymers 0.000 claims 1
- 239000010410 layer Substances 0.000 description 343
- 239000000243 solution Substances 0.000 description 115
- 239000000203 mixture Substances 0.000 description 82
- 239000011159 matrix material Substances 0.000 description 57
- 238000006116 polymerization reaction Methods 0.000 description 53
- 239000003795 chemical substances by application Substances 0.000 description 51
- 125000000217 alkyl group Chemical group 0.000 description 50
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 43
- 238000006243 chemical reaction Methods 0.000 description 43
- 125000003118 aryl group Chemical group 0.000 description 41
- NQVIIUBWMBHLOZ-UHFFFAOYSA-N 2-[2-hydroxyethyl-[6-[(4-methoxyphenyl)methylamino]-9-propan-2-ylpurin-2-yl]amino]ethanol Chemical compound C1=CC(OC)=CC=C1CNC1=NC(N(CCO)CCO)=NC2=C1N=CN2C(C)C NQVIIUBWMBHLOZ-UHFFFAOYSA-N 0.000 description 34
- 229920000747 poly(lactic acid) Polymers 0.000 description 33
- JJTUDXZGHPGLLC-IMJSIDKUSA-N 4511-42-6 Chemical compound C[C@@H]1OC(=O)[C@H](C)OC1=O JJTUDXZGHPGLLC-IMJSIDKUSA-N 0.000 description 30
- 239000012071 phase Substances 0.000 description 27
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- 229910052757 nitrogen Inorganic materials 0.000 description 24
- 229910001220 stainless steel Inorganic materials 0.000 description 23
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- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 21
- 125000003342 alkenyl group Chemical group 0.000 description 21
- 239000011521 glass Substances 0.000 description 21
- 239000003814 drug Substances 0.000 description 20
- JJTUDXZGHPGLLC-UHFFFAOYSA-N lactide Chemical compound CC1OC(=O)C(C)OC1=O JJTUDXZGHPGLLC-UHFFFAOYSA-N 0.000 description 20
- 125000000304 alkynyl group Chemical group 0.000 description 19
- 229940079593 drug Drugs 0.000 description 19
- 238000011068 loading method Methods 0.000 description 19
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 18
- 125000003545 alkoxy group Chemical group 0.000 description 18
- 125000000623 heterocyclic group Chemical group 0.000 description 18
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 17
- 230000000977 initiatory effect Effects 0.000 description 16
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- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 13
- 230000008021 deposition Effects 0.000 description 13
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical group [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 description 13
- 229920000578 graft copolymer Polymers 0.000 description 13
- 239000011135 tin Substances 0.000 description 13
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 13
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- 125000004432 carbon atom Chemical group C* 0.000 description 12
- 239000011247 coating layer Substances 0.000 description 12
- 238000009792 diffusion process Methods 0.000 description 12
- 238000002474 experimental method Methods 0.000 description 12
- 125000000392 cycloalkenyl group Chemical group 0.000 description 11
- 238000001704 evaporation Methods 0.000 description 11
- 229910052718 tin Inorganic materials 0.000 description 11
- 238000004833 X-ray photoelectron spectroscopy Methods 0.000 description 10
- 125000002947 alkylene group Chemical group 0.000 description 10
- 125000000753 cycloalkyl group Chemical group 0.000 description 10
- 125000005843 halogen group Chemical group 0.000 description 10
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 10
- 229920006254 polymer film Polymers 0.000 description 10
- 238000012694 Lactone Polymerization Methods 0.000 description 9
- 150000001412 amines Chemical class 0.000 description 9
- 238000013459 approach Methods 0.000 description 9
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- 241000894007 species Species 0.000 description 8
- 230000004913 activation Effects 0.000 description 7
- 125000002252 acyl group Chemical group 0.000 description 7
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Classifications
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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
- A61L31/00—Materials for other surgical articles, e.g. stents, stent-grafts, shunts, surgical drapes, guide wires, materials for adhesion prevention, occluding devices, surgical gloves, tissue fixation devices
- A61L31/04—Macromolecular materials
- A61L31/06—Macromolecular materials obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
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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
- A61L31/00—Materials for other surgical articles, e.g. stents, stent-grafts, shunts, surgical drapes, guide wires, materials for adhesion prevention, occluding devices, surgical gloves, tissue fixation devices
- A61L31/08—Materials for coatings
- A61L31/10—Macromolecular materials
-
- 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
- A61L31/00—Materials for other surgical articles, e.g. stents, stent-grafts, shunts, surgical drapes, guide wires, materials for adhesion prevention, occluding devices, surgical gloves, tissue fixation devices
- A61L31/14—Materials characterised by their function or physical properties, e.g. injectable or lubricating compositions, shape-memory materials, surface modified materials
- A61L31/16—Biologically active materials, e.g. therapeutic substances
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- A—HUMAN NECESSITIES
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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
- A61L33/00—Antithrombogenic treatment of surgical articles, e.g. sutures, catheters, prostheses, or of articles for the manipulation or conditioning of blood; Materials for such treatment
- A61L33/0076—Chemical modification of the substrate
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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
- A61L2300/60—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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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/13—Hollow or container type article [e.g., tube, vase, etc.]
- Y10T428/1352—Polymer or resin containing [i.e., natural or synthetic]
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/13—Hollow or container type article [e.g., tube, vase, etc.]
- Y10T428/1352—Polymer or resin containing [i.e., natural or synthetic]
- Y10T428/139—Open-ended, self-supporting conduit, cylinder, or tube-type article
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/13—Hollow or container type article [e.g., tube, vase, etc.]
- Y10T428/1352—Polymer or resin containing [i.e., natural or synthetic]
- Y10T428/139—Open-ended, self-supporting conduit, cylinder, or tube-type article
- Y10T428/1393—Multilayer [continuous layer]
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/31504—Composite [nonstructural laminate]
- Y10T428/31652—Of asbestos
- Y10T428/31663—As siloxane, silicone or silane
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/31504—Composite [nonstructural laminate]
- Y10T428/31786—Of polyester [e.g., alkyd, etc.]
Landscapes
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Epidemiology (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- Surgery (AREA)
- Heart & Thoracic Surgery (AREA)
- Vascular Medicine (AREA)
- Chemical & Material Sciences (AREA)
- Molecular Biology (AREA)
- Engineering & Computer Science (AREA)
- Medicinal Chemistry (AREA)
- Biomedical Technology (AREA)
- Hematology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Materials For Medical Uses (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US35757302P | 2002-02-15 | 2002-02-15 |
Publications (1)
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| ZA200406448B true ZA200406448B (en) | 2006-05-31 |
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ZA200406448A ZA200406448B (en) | 2002-02-15 | 2004-08-13 | Polymer coating for medical devices |
Country Status (24)
| Country | Link |
|---|---|
| US (4) | US7160592B2 (fr) |
| EP (2) | EP1764118B1 (fr) |
| JP (1) | JP4472348B2 (fr) |
| KR (1) | KR20040097126A (fr) |
| CN (2) | CN1911460A (fr) |
| AT (2) | ATE348643T1 (fr) |
| AU (2) | AU2003215495B2 (fr) |
| CA (1) | CA2476431A1 (fr) |
| CY (1) | CY1107549T1 (fr) |
| DE (2) | DE60333955D1 (fr) |
| DK (2) | DK1764118T3 (fr) |
| ES (2) | ES2276084T3 (fr) |
| HK (2) | HK1072205A1 (fr) |
| HU (1) | HUP0402591A2 (fr) |
| IL (1) | IL163535A0 (fr) |
| MX (1) | MXPA04007898A (fr) |
| NO (1) | NO20043843L (fr) |
| NZ (1) | NZ534682A (fr) |
| PL (1) | PL371517A1 (fr) |
| PT (2) | PT1764118E (fr) |
| RU (1) | RU2308976C2 (fr) |
| SI (2) | SI1492581T1 (fr) |
| WO (1) | WO2003068289A1 (fr) |
| ZA (1) | ZA200406448B (fr) |
Families Citing this family (225)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA2178541C (fr) * | 1995-06-07 | 2009-11-24 | Neal E. Fearnot | Dispositif medical implantable |
| US7713297B2 (en) | 1998-04-11 | 2010-05-11 | Boston Scientific Scimed, Inc. | Drug-releasing stent with ceramic-containing layer |
| US7220276B1 (en) * | 2000-03-06 | 2007-05-22 | Surmodics, Inc. | Endovascular graft coatings |
| US6512072B1 (en) | 2000-06-12 | 2003-01-28 | Dow Corning Corporation | Fast cure film forming formulation |
| US8038708B2 (en) * | 2001-02-05 | 2011-10-18 | Cook Medical Technologies Llc | Implantable device with remodelable material and covering material |
| US20070027535A1 (en) * | 2005-07-28 | 2007-02-01 | Cook Incorporated | Implantable thromboresistant valve |
| WO2003002243A2 (fr) | 2001-06-27 | 2003-01-09 | Remon Medical Technologies Ltd. | Procede et dispositif pour la formation electrochimique d'especes therapeutiques in vivo |
| US8741378B1 (en) * | 2001-06-27 | 2014-06-03 | Advanced Cardiovascular Systems, Inc. | Methods of coating an implantable device |
| US20060093771A1 (en) * | 2002-02-15 | 2006-05-04 | Frantisek Rypacek | Polymer coating for medical devices |
| JP2006500996A (ja) * | 2002-09-26 | 2006-01-12 | エンドバスキュラー デバイセス インコーポレイテッド | 溶出性生体適合性移植可能医療器具を介してマイトマイシンを送達するための装置および方法 |
| CN1767798A (zh) * | 2003-03-31 | 2006-05-03 | 皇家飞利浦电子股份有限公司 | 带涂层的医疗设备 |
| US20040236399A1 (en) * | 2003-04-22 | 2004-11-25 | Medtronic Vascular, Inc. | Stent with improved surface adhesion |
| US7067169B2 (en) * | 2003-06-04 | 2006-06-27 | Chemat Technology Inc. | Coated implants and methods of coating |
| WO2005056354A2 (fr) * | 2003-12-03 | 2005-06-23 | Gedeon Anthony A | Procede de resistance a l'accumulation d'agents contaminants et a l'oxydation de surfaces de vehicule et d'autres surfaces |
| WO2005069785A2 (fr) * | 2003-12-16 | 2005-08-04 | Gedeon Anthony A | Procede permettant de traiter des surfaces en vue d'une autosterilisation et d'une resistance a la proliferation microbienne |
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