WO2001036008A2 - Medical devices coated with elastic polymeric material - Google Patents
Medical devices coated with elastic polymeric material Download PDFInfo
- Publication number
- WO2001036008A2 WO2001036008A2 PCT/US2000/031314 US0031314W WO0136008A2 WO 2001036008 A2 WO2001036008 A2 WO 2001036008A2 US 0031314 W US0031314 W US 0031314W WO 0136008 A2 WO0136008 A2 WO 0136008A2
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- coating
- covering
- cyclohexanone
- group
- ethanol
- Prior art date
Links
- 239000000463 material Substances 0.000 title claims description 7
- 238000000576 coating method Methods 0.000 claims abstract description 75
- 239000011248 coating agent Substances 0.000 claims abstract description 69
- 230000001464 adherent effect Effects 0.000 claims abstract description 9
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 claims description 48
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 38
- 239000000758 substrate Substances 0.000 claims description 33
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 32
- -1 poly(L-lactic acid) Polymers 0.000 claims description 24
- DKPFZGUDAPQIHT-UHFFFAOYSA-N butyl acetate Chemical compound CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 claims description 22
- 229920002635 polyurethane Polymers 0.000 claims description 22
- 239000004814 polyurethane Substances 0.000 claims description 22
- 239000000203 mixture Substances 0.000 claims description 21
- 235000019441 ethanol Nutrition 0.000 claims description 19
- 239000000017 hydrogel Substances 0.000 claims description 19
- 229920000647 polyepoxide Polymers 0.000 claims description 17
- 150000001875 compounds Chemical class 0.000 claims description 16
- 239000003822 epoxy resin Substances 0.000 claims description 16
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 16
- 229920000178 Acrylic resin Polymers 0.000 claims description 15
- 239000004925 Acrylic resin Substances 0.000 claims description 15
- WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 claims description 13
- 239000003795 chemical substances by application Substances 0.000 claims description 11
- 229920000058 polyacrylate Polymers 0.000 claims description 10
- 229910001220 stainless steel Inorganic materials 0.000 claims description 10
- 239000010935 stainless steel Substances 0.000 claims description 10
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 9
- 229910052751 metal Inorganic materials 0.000 claims description 9
- 239000002184 metal Substances 0.000 claims description 9
- 238000000034 method Methods 0.000 claims description 9
- 239000008096 xylene Substances 0.000 claims description 9
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims description 8
- 229920001228 polyisocyanate Polymers 0.000 claims description 7
- 239000005056 polyisocyanate Substances 0.000 claims description 7
- 229920000036 polyvinylpyrrolidone Polymers 0.000 claims description 7
- 239000001267 polyvinylpyrrolidone Substances 0.000 claims description 7
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 claims description 7
- 125000001931 aliphatic group Chemical group 0.000 claims description 6
- 229920002678 cellulose Polymers 0.000 claims description 6
- HTTJABKRGRZYRN-UHFFFAOYSA-N Heparin Chemical compound OC1C(NC(=O)C)C(O)OC(COS(O)(=O)=O)C1OC1C(OS(O)(=O)=O)C(O)C(OC2C(C(OS(O)(=O)=O)C(OC3C(C(O)C(O)C(O3)C(O)=O)OS(O)(=O)=O)C(CO)O2)NS(O)(=O)=O)C(C(O)=O)O1 HTTJABKRGRZYRN-UHFFFAOYSA-N 0.000 claims description 5
- 230000002491 angiogenic effect Effects 0.000 claims description 5
- 229960001716 benzalkonium Drugs 0.000 claims description 5
- CYDRXTMLKJDRQH-UHFFFAOYSA-N benzododecinium Chemical compound CCCCCCCCCCCC[N+](C)(C)CC1=CC=CC=C1 CYDRXTMLKJDRQH-UHFFFAOYSA-N 0.000 claims description 5
- 229920000669 heparin Polymers 0.000 claims description 5
- YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 claims description 5
- 229960004319 trichloroacetic acid Drugs 0.000 claims description 5
- 229910000990 Ni alloy Inorganic materials 0.000 claims description 4
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims description 4
- 229920005749 polyurethane resin Polymers 0.000 claims description 4
- 229910000838 Al alloy Inorganic materials 0.000 claims description 3
- 229930012538 Paclitaxel Natural products 0.000 claims description 3
- 239000003146 anticoagulant agent Substances 0.000 claims description 3
- 229940127219 anticoagulant drug Drugs 0.000 claims description 3
- 229940034982 antineoplastic agent Drugs 0.000 claims description 3
- 239000002246 antineoplastic agent Substances 0.000 claims description 3
- 229940127218 antiplatelet drug Drugs 0.000 claims description 3
- 150000002739 metals Chemical class 0.000 claims description 3
- 229960001592 paclitaxel Drugs 0.000 claims description 3
- 239000000106 platelet aggregation inhibitor Substances 0.000 claims description 3
- 229920002959 polymer blend Polymers 0.000 claims description 3
- 229920001296 polysiloxane Polymers 0.000 claims description 3
- RCINICONZNJXQF-MZXODVADSA-N taxol Chemical compound O([C@@H]1[C@@]2(C[C@@H](C(C)=C(C2(C)C)[C@H](C([C@]2(C)[C@@H](O)C[C@H]3OC[C@]3([C@H]21)OC(C)=O)=O)OC(=O)C)OC(=O)[C@H](O)[C@@H](NC(=O)C=1C=CC=CC=1)C=1C=CC=CC=1)O)C(=O)C1=CC=CC=C1 RCINICONZNJXQF-MZXODVADSA-N 0.000 claims description 3
- 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 2
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 claims description 2
- 102000008186 Collagen Human genes 0.000 claims description 2
- 108010035532 Collagen Proteins 0.000 claims description 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 2
- 229910000881 Cu alloy Inorganic materials 0.000 claims description 2
- 229920001651 Cyanoacrylate Polymers 0.000 claims description 2
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 claims description 2
- 102000009123 Fibrin Human genes 0.000 claims description 2
- 108010073385 Fibrin Proteins 0.000 claims description 2
- BWGVNKXGVNDBDI-UHFFFAOYSA-N Fibrin monomer Chemical compound CNC(=O)CNC(=O)CN BWGVNKXGVNDBDI-UHFFFAOYSA-N 0.000 claims description 2
- 102000008946 Fibrinogen Human genes 0.000 claims description 2
- 108010049003 Fibrinogen Proteins 0.000 claims description 2
- 239000004952 Polyamide Substances 0.000 claims description 2
- 229920002732 Polyanhydride Polymers 0.000 claims description 2
- 229920000954 Polyglycolide Polymers 0.000 claims description 2
- 229920000331 Polyhydroxybutyrate Polymers 0.000 claims description 2
- 239000004642 Polyimide Substances 0.000 claims description 2
- 229920001710 Polyorthoester Polymers 0.000 claims description 2
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 claims description 2
- 229920002472 Starch Polymers 0.000 claims description 2
- 229910001069 Ti alloy Inorganic materials 0.000 claims description 2
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 claims description 2
- 229910001297 Zn alloy Inorganic materials 0.000 claims description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims description 2
- 239000004037 angiogenesis inhibitor Substances 0.000 claims description 2
- 239000001913 cellulose Substances 0.000 claims description 2
- 239000011651 chromium Substances 0.000 claims description 2
- 229920001436 collagen Polymers 0.000 claims description 2
- 239000010949 copper Substances 0.000 claims description 2
- NLCKLZIHJQEMCU-UHFFFAOYSA-N cyano prop-2-enoate Chemical class C=CC(=O)OC#N NLCKLZIHJQEMCU-UHFFFAOYSA-N 0.000 claims description 2
- 229950003499 fibrin Drugs 0.000 claims description 2
- 229940012952 fibrinogen Drugs 0.000 claims description 2
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 claims description 2
- 239000010931 gold Substances 0.000 claims description 2
- 229920002674 hyaluronan Polymers 0.000 claims description 2
- 229960003160 hyaluronic acid Drugs 0.000 claims description 2
- 239000002831 pharmacologic agent Substances 0.000 claims description 2
- 229920006211 poly(glycolic acid-co-trimethylene carbonate) Polymers 0.000 claims description 2
- 239000005015 poly(hydroxybutyrate) Substances 0.000 claims description 2
- 229920001849 poly(hydroxybutyrate-co-valerate) Polymers 0.000 claims description 2
- 229920001606 poly(lactic acid-co-glycolic acid) Polymers 0.000 claims description 2
- 239000002745 poly(ortho ester) Substances 0.000 claims description 2
- 229920002463 poly(p-dioxanone) polymer Polymers 0.000 claims description 2
- 229920002627 poly(phosphazenes) Polymers 0.000 claims description 2
- 229920001281 polyalkylene Polymers 0.000 claims description 2
- 229920002647 polyamide Polymers 0.000 claims description 2
- 229920001610 polycaprolactone Polymers 0.000 claims description 2
- 239000004632 polycaprolactone Substances 0.000 claims description 2
- 239000000622 polydioxanone Substances 0.000 claims description 2
- 229920000728 polyester Polymers 0.000 claims description 2
- 229920001721 polyimide Polymers 0.000 claims description 2
- 239000012781 shape memory material Substances 0.000 claims description 2
- 239000004332 silver Substances 0.000 claims description 2
- 239000008107 starch Substances 0.000 claims description 2
- 235000019698 starch Nutrition 0.000 claims description 2
- GUVRBAGPIYLISA-UHFFFAOYSA-N tantalum atom Chemical compound [Ta] GUVRBAGPIYLISA-UHFFFAOYSA-N 0.000 claims description 2
- 230000002885 thrombogenetic effect Effects 0.000 claims description 2
- 229910052719 titanium Inorganic materials 0.000 claims description 2
- 239000010936 titanium Substances 0.000 claims description 2
- 229910001316 Ag alloy Inorganic materials 0.000 claims 1
- 229910001020 Au alloy Inorganic materials 0.000 claims 1
- 229910000599 Cr alloy Inorganic materials 0.000 claims 1
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 claims 1
- 239000004698 Polyethylene Substances 0.000 claims 1
- 239000004743 Polypropylene Substances 0.000 claims 1
- 229910001260 Pt alloy Inorganic materials 0.000 claims 1
- 229910001362 Ta alloys Inorganic materials 0.000 claims 1
- 150000001413 amino acids Chemical class 0.000 claims 1
- 230000001772 anti-angiogenic effect Effects 0.000 claims 1
- 230000002924 anti-infective effect Effects 0.000 claims 1
- 230000000118 anti-neoplastic effect Effects 0.000 claims 1
- 230000002965 anti-thrombogenic effect Effects 0.000 claims 1
- 239000004599 antimicrobial Substances 0.000 claims 1
- 239000003102 growth factor Substances 0.000 claims 1
- 239000004310 lactic acid Substances 0.000 claims 1
- 230000000144 pharmacologic effect Effects 0.000 claims 1
- 229920000573 polyethylene Polymers 0.000 claims 1
- 229920001155 polypropylene Polymers 0.000 claims 1
- 229920002689 polyvinyl acetate Polymers 0.000 claims 1
- 239000011118 polyvinyl acetate Substances 0.000 claims 1
- 229920000915 polyvinyl chloride Polymers 0.000 claims 1
- 239000004800 polyvinyl chloride Substances 0.000 claims 1
- 229940079593 drug Drugs 0.000 abstract description 12
- 239000003814 drug Substances 0.000 abstract description 12
- 239000010410 layer Substances 0.000 description 21
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 18
- 229920000642 polymer Polymers 0.000 description 10
- 238000012360 testing method Methods 0.000 description 9
- 229920003332 Epotuf® Polymers 0.000 description 7
- 235000019445 benzyl alcohol Nutrition 0.000 description 6
- 230000002792 vascular Effects 0.000 description 5
- 238000005336 cracking Methods 0.000 description 4
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 3
- 229920001577 copolymer Polymers 0.000 description 3
- 229920006242 ethylene acrylic acid copolymer Polymers 0.000 description 3
- 238000001125 extrusion Methods 0.000 description 3
- UPMLOUAZCHDJJD-UHFFFAOYSA-N 4,4'-Diphenylmethane Diisocyanate Chemical compound C1=CC(N=C=O)=CC=C1CC1=CC=C(N=C=O)C=C1 UPMLOUAZCHDJJD-UHFFFAOYSA-N 0.000 description 2
- 108700009938 HBAC Proteins 0.000 description 2
- 239000004809 Teflon Substances 0.000 description 2
- 229920006362 Teflon® Polymers 0.000 description 2
- 239000013543 active substance Substances 0.000 description 2
- 239000003242 anti bacterial agent Substances 0.000 description 2
- 229940088710 antibiotic agent Drugs 0.000 description 2
- 239000001045 blue dye Substances 0.000 description 2
- 229920003086 cellulose ether Polymers 0.000 description 2
- 238000004140 cleaning Methods 0.000 description 2
- 239000011247 coating layer Substances 0.000 description 2
- 229920002457 flexible plastic Polymers 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 238000003780 insertion Methods 0.000 description 2
- 230000037431 insertion Effects 0.000 description 2
- 229920000515 polycarbonate Polymers 0.000 description 2
- 239000004417 polycarbonate Substances 0.000 description 2
- BFKJFAAPBSQJPD-UHFFFAOYSA-N tetrafluoroethene Chemical compound FC(F)=C(F)F BFKJFAAPBSQJPD-UHFFFAOYSA-N 0.000 description 2
- 229920002554 vinyl polymer Polymers 0.000 description 2
- 239000004593 Epoxy Substances 0.000 description 1
- 229920000877 Melamine resin Polymers 0.000 description 1
- 229920001244 Poly(D,L-lactide) Polymers 0.000 description 1
- 208000007536 Thrombosis Diseases 0.000 description 1
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 1
- 208000027418 Wounds and injury Diseases 0.000 description 1
- 150000001241 acetals Chemical class 0.000 description 1
- 239000002390 adhesive tape Substances 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 238000005452 bending Methods 0.000 description 1
- 229920002988 biodegradable polymer Polymers 0.000 description 1
- 239000004621 biodegradable polymer Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 210000001124 body fluid Anatomy 0.000 description 1
- 229910052804 chromium Inorganic materials 0.000 description 1
- 239000003431 cross linking reagent Substances 0.000 description 1
- 230000006378 damage Effects 0.000 description 1
- 230000032798 delamination Effects 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- 150000002009 diols Chemical class 0.000 description 1
- 238000003618 dip coating Methods 0.000 description 1
- 238000007598 dipping method Methods 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 229920001971 elastomer Polymers 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 125000003700 epoxy group Chemical group 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 210000005224 forefinger Anatomy 0.000 description 1
- 230000006870 function Effects 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 230000002209 hydrophobic effect Effects 0.000 description 1
- 208000015181 infectious disease Diseases 0.000 description 1
- 208000014674 injury Diseases 0.000 description 1
- 239000012948 isocyanate Substances 0.000 description 1
- 150000002513 isocyanates Chemical class 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 150000003891 oxalate salts Chemical class 0.000 description 1
- 239000006223 plastic coating Substances 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 229920001308 poly(aminoacid) Polymers 0.000 description 1
- 229920001084 poly(chloroprene) Polymers 0.000 description 1
- 229920000747 poly(lactic acid) Polymers 0.000 description 1
- 239000013047 polymeric layer Substances 0.000 description 1
- 235000013824 polyphenols Nutrition 0.000 description 1
- 229920000166 polytrimethylene carbonate Polymers 0.000 description 1
- 238000003825 pressing Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 208000037803 restenosis Diseases 0.000 description 1
- 239000005060 rubber Substances 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 229910052715 tantalum Inorganic materials 0.000 description 1
- 239000008399 tap water Substances 0.000 description 1
- 235000020679 tap water Nutrition 0.000 description 1
- 210000003813 thumb Anatomy 0.000 description 1
- 238000011179 visual inspection Methods 0.000 description 1
Classifications
-
- 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
- A61L29/00—Materials for catheters, medical tubing, cannulae, or endoscopes or for coating catheters
- A61L29/14—Materials characterised by their function or physical properties, e.g. lubricating compositions
- A61L29/16—Biologically active materials, e.g. therapeutic substances
-
- 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
- A61L29/00—Materials for catheters, medical tubing, cannulae, or endoscopes or for coating catheters
- A61L29/08—Materials for coatings
-
- 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
- A61L29/00—Materials for catheters, medical tubing, cannulae, or endoscopes or for coating catheters
- A61L29/08—Materials for coatings
- A61L29/085—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
- A61L31/08—Materials for coatings
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61F—FILTERS IMPLANTABLE INTO BLOOD VESSELS; PROSTHESES; DEVICES PROVIDING PATENCY TO, OR PREVENTING COLLAPSING OF, TUBULAR STRUCTURES OF THE BODY, e.g. STENTS; ORTHOPAEDIC, NURSING OR CONTRACEPTIVE DEVICES; FOMENTATION; TREATMENT OR PROTECTION OF EYES OR EARS; BANDAGES, DRESSINGS OR ABSORBENT PADS; FIRST-AID KITS
- A61F2/00—Filters implantable into blood vessels; Prostheses, i.e. artificial substitutes or replacements for parts of the body; Appliances for connecting them with the body; Devices providing patency to, or preventing collapsing of, tubular structures of the body, e.g. stents
- A61F2/02—Prostheses implantable into the body
- A61F2/04—Hollow or tubular parts of organs, e.g. bladders, tracheae, bronchi or bile ducts
- A61F2/06—Blood vessels
- A61F2/07—Stent-grafts
- A61F2002/072—Encapsulated stents, e.g. wire or whole stent embedded in lining
-
- 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
Definitions
- the present invention relates to insertable medical devices with modified surface
- vascular and other stents are also examples of insertable medical devices.
- the typical vascular stent configuration includes metal screen-like scaffolds which are inserted in a
- U.S. Patent No. 5,383,928 issued to Scott et al. describes a stent which is at least partially covered with a sleeve which contains one or more drugs, and which removably
- Thin coatings of TEFLON ® also have been used on coil guide wires. Although such
- coatings can be flexible, they require baking at very high temperatures ( ⁇ 370°C), and adhering
- the present invention comprises a medical device comprising an insertable substrate, an elastic polymeric covering adherent to the substrate, and a polymeric coating adherent to
- the covering such that the coating and covering possess desirable surface characteristics
- devices include but are not limited to guide wires, forceps, trochars, stents and catheters.
- polymeric covering and coating is designed to be sufficiently flexible to allow the substrate
- the substrate may be a relatively rigid structure such as a vascular stent, in which case the flexible polymeric covering and coating is designed to be capable of
- the covering and coating are designed to provide a lubricious surface.
- Other devices require non-lubricious surfaces in order to ensure that they remain in place once inserted.
- the coating is designed to provide such a non -lubricious surface.
- invention contemplates a stent design which has a flexible elastic plastic coating permanently
- the coating expands with the stent and retains its integrity
- the substrate can be composed of a variety
- suitable coatings preferably include a variety of
- hydrogels comprising one or more components selected from the group consisting of polyvinylpyrrolidone, epoxy resin, acrylic polymer, acrylic resin, and aliphatic polyisocyanate.
- a binding layer or precoat can be applied to the substrate to enhance the binding
- Such precoats can contain polymers including but not limited
- these coatings can be any coatings which enhance adhesion onto substrates.
- these coatings can be any coatings which enhance adhesion onto substrates.
- these coatings can be any coatings which enhance adhesion onto substrates.
- crosslinking agents including but not limited to melamine resins, isocyanates,
- agents such as antibiotics, anticoagulants, antiplatelet agents, antineoplastic agents, anti-oxidants
- angiogenic agents and angiogenic agents are incorporated into the coating.
- angiogenic agents and angiogenic agents are incorporated into the coating.
- the coating may contain one or more drugs to, for example, prevent thrombus formation
- the present invention also includes a method of modifying the surface properties of
- the invention also incorporates physiologically or
- insertable medical devices is dependent to varying degrees on the surface properties of the
- a surface that is lubricious can permit the easier, safer and less uncomfortable
- a device that has a non-lubricious surface can be more securely fixed in a desired location, providing added safety and ease of use, and the inclusion
- Such modifications include, but are not limited to, stylets, guide wires, flexible forceps used
- the present invention provides a surface to such medical devices such that improved
- the medical devices can be provided to such medical devices.
- the medical devices are configured to provide surface characteristics to such medical devices.
- contemplated in this invention comprise a substrate, a covering and a coating.
- the substrate is a substrate, a covering and a coating.
- the substrate is
- Such a substrate often has physical
- the polymeric covering is
- adherent to the substrate surface is flexible, such that it can be bent and flexed repeatedly
- the covering preferably is elastic, and able to
- the covering preferably is elastic and flexible when applied to devices such as endoscopic forceps or guide wires.
- the covering can be applied in one or
- Covering the polymeric covering is a polymeric coating, which provides the desired
- the coating can be of the same composition as
- the covering or can be of a different composition.
- the coating also has the properties of flexibility and elasticity, and optionally can be hydrophobic, hydrophilic or of intermediate
- the coating can be applied with one or more layers which may have the same or different composition, is one layer thick or optionally can be several layers thick. Together,
- the covering and the coating are preferably less than 100 ⁇ m thick, and more preferably less
- the polymeric covering and coating preferably are sufficiently flexible so
- the flexible polymeric layer(s) preferably also are
- the coating and covering preferably are applied to the substrate optionally by
- Coating preferably is performed optionally by spraying or by
- the stent comprises a rigid but expandable framework.
- coating and covering of the present invention preferably is sufficiently adherent, flexible and elastic such that when the stent is expanded, the coating and covering forms an adherent sheath that is attached to the struts of the stent and stretches between them, providing a greatly
- coating is non-lubricious, aiding in maintaining the stent in a desired location once the stent
- agents include, but are not
- antibiotics include antibiotics, anticoagulants, anti-platelet agents, antineoplastic agents, thrombogenic
- one or more bonding layers can be used as a primer for the substrate
- the bonding layers preferably are less than
- the substrate of the device can be composed of a variety of materials. Examples include, but are not limited to, metals such as titanium, silver, gold, platinum, aluminum,
- chromium chromium, stainless steel or tantalum, and shape memory materials, including but not limited
- nickel/titanium alloys copper/zinc alloys, and nickel/aluminum alloys.
- Other examples are possible.
- polymeric materials including but not limited to biodegradable materials such as
- polyurethanes silicones, polyamides, polyimides, cellulose esters, cellulose ethers,
- Examples of compounds that are used for the covering include but are not limited to
- polyurethane polyvinyl acetals, acrylate polymers and copolymers, vinyl acetate polymers and
- the covering is comprised of a hybrid polymer mixture, an example of which includes, but is not limited to, polyurethane
- the covering is applied by dipping the covering
- the concentration of the polyurethane polymer is from about 10% to about 30% w/w.
- covering preferably is oven cured such as at about 85°C for from about 30 minutes to about
- a bonding layer can be applied to the substrate as a precoat before the
- a prefe ⁇ ed layer that can be used comprises a composition comprising
- cyclohexanone from about 3% to about 4% w/w polyurethane resin, from about 2.5 % to
- the coating layer of the present invention is preferably a hydrogel.
- used to form the hydrogel preferably comprise a mixture of at least one and more preferably
- At least two, components selected from the group consisting of ethanol, polyvinylpyrrolidone, benzyl alcohol, cyclohexanone, tetrahydrofuran, xylene, epoxy resin, acrylic resin or polymer,
- a prefe ⁇ ed hydrogel composition comprises from about 10% to about
- Another prefe ⁇ ed composition comprises from about 10%> to about 20%> w/w ethanol, from
- tetrahydroafuran from about 2% to about 3% w/w xylene, from about 0.5% to about 1.5%>
- hydrogel composition comprises from about 35%> to about 45%> w/w ethanol, from about 20%
- One embodiment of the present invention incorporates physiologic and/or
- the coating comprises an outer layer comprised of a composition comprised of
- tetrahydrofuran from about 12% to about 20% w/w cyclohexanone, from about 10% to about
- the present invention includes a method of providing desirable surface properties to
- the method comprises applying one or more layers of the
- compositions disclosed herein to the substrate surface in order to provide the appropriate surface for the function of the medical device.
- Epotuf 38-505 (Reichold, Research Triangle Park, NC) is an epoxy resin.
- Paraloid ® AT-63 (Rohm and Haas, Co., Philadelphia, PA) is a crosslinkable acrylic polymer
- the sample was tested for adhesion under both wet and dry conditions.
- the sample was dipped in Genti an Violet, Huckers Gram Stain Solution [(CH 3 ) 2 NC 6 H 4 ] 2 C:C 6 H 4 :N(CH 3 ) 2 C1; VWR, West Chester, PA , Cat No. VW3567-1] for 5 - 10
- the tape was easy to see visually because it was stained with the blue dye.
- the tape was
- the coating passed the wet and dry adhesion tests.
- the sample was lubricious when wet.
- the coated sample was oven dried at 85°C for about 60 minutes, and tested as
- Example 1 The sample was very flexible and the coating passed the wet and dry adhesion tests. The sample was lubricious when wet.
- the coated sample was oven cured for about one hour at 75 °C.
- the sample then was
- Example 4 tested as described n Example 1. The sample and passed the wet and dry adhesion tests. The sample was moderately lubricious when wet. Example 4
- a stainless steel mandril was dipped in the precoat solution below for 20 seconds.
- coated sample was dried for about 45 minutes at 75°C.
- Paraloid ® AT-746 (Rohm and Haas, Co., Philadelphia, PA) is a crosslinkable acrylic polymer
- Example 3 was coated over the polyurethane layers as described in Example 1. The sample
- Example 5 was tested as described in Example 1 , and exhibited good flexibility and good wet and dry adhesion, and showed moderate wet lubricity.
- Example 3 The sample was cured at 65 °C for 20 minutes after each coating
- Example 2 The sample was dipped in the following hydrogel solution using the method of Example 1 :
- Paclitaxel 1.0 %(w/w)
- HBAC Benzalkonium heparinate
- the sample was oven dried for one hour at 75°C.
- the sample passed the wet and dry
- Example 4 As in Example 4, The sample was oven dried for 20 minutes at 60°C after each coating
- the sample was oven dried for one hour at 75 °C.
- the sample was tested for adhesion
- a stainless steel madril was dipped in a Precoat having the following composition for 20 seconds and then withdrawn at 30 mm/second.
- Example 6 solution of Example 6 was coated over the polyurethane layers as described in Example 6.
- Example 2 The sample was tested as described in Example 1 and was flexible and had good wet and dry adhesion. The sample was moderately lubricious when wet.
Abstract
Description
Claims
Priority Applications (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP00978657A EP1233724A4 (en) | 1999-11-18 | 2000-11-15 | Flexible sealed coil-like devices |
AU16097/01A AU1609701A (en) | 1999-11-18 | 2000-11-15 | Flexible sealed coil-like devices |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US44289199A | 1999-11-18 | 1999-11-18 | |
US09/442,891 | 1999-11-18 |
Publications (2)
Publication Number | Publication Date |
---|---|
WO2001036008A2 true WO2001036008A2 (en) | 2001-05-25 |
WO2001036008A3 WO2001036008A3 (en) | 2001-12-13 |
Family
ID=23758557
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/US2000/031314 WO2001036008A2 (en) | 1999-11-18 | 2000-11-15 | Medical devices coated with elastic polymeric material |
Country Status (3)
Country | Link |
---|---|
EP (1) | EP1233724A4 (en) |
AU (1) | AU1609701A (en) |
WO (1) | WO2001036008A2 (en) |
Cited By (12)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE10202467A1 (en) * | 2002-01-23 | 2003-07-24 | Polyzenix Gmbh | Device, useful as an artificial implant, comprises a substrate based on nitinol having at least a partial coating of a phosphazene polymer. |
WO2004052420A2 (en) * | 2002-12-06 | 2004-06-24 | Surmodics, Inc. | Barriers for bioactive agent-containing polymeric coatings |
US7265199B2 (en) | 2000-04-11 | 2007-09-04 | Celonova Biosciences Germany Gmbh | Poly-tri-fluoro-ethoxypolyphosphazene coverings and films |
US7771468B2 (en) | 2001-03-16 | 2010-08-10 | Angiotech Biocoatings Corp. | Medicated stent having multi-layer polymer coating |
US7922764B2 (en) | 2006-10-10 | 2011-04-12 | Celonova Bioscience, Inc. | Bioprosthetic heart valve with polyphosphazene |
US8101275B2 (en) | 2001-08-17 | 2012-01-24 | Celonova Biosciences, Inc. | Device based on nitinol, a process for its production, and its use |
US9080146B2 (en) | 2001-01-11 | 2015-07-14 | Celonova Biosciences, Inc. | Substrates containing polyphosphazene as matrices and substrates containing polyphosphazene with a micro-structured surface |
US9107850B2 (en) | 2004-10-25 | 2015-08-18 | Celonova Biosciences, Inc. | Color-coded and sized loadable polymeric particles for therapeutic and/or diagnostic applications and methods of preparing and using the same |
US9114162B2 (en) | 2004-10-25 | 2015-08-25 | Celonova Biosciences, Inc. | Loadable polymeric particles for enhanced imaging in clinical applications and methods of preparing and using the same |
CN110180038A (en) * | 2019-06-21 | 2019-08-30 | 西南大学 | Has the kirsite vascular stent material of drug slow release function superhigh-flexibility coating |
US10973770B2 (en) | 2004-10-25 | 2021-04-13 | Varian Medical Systems, Inc. | Color-coded and sized loadable polymeric particles for therapeutic and/or diagnostic applications and methods of preparing and using the same |
US11167064B2 (en) | 2016-07-14 | 2021-11-09 | Hollister Incorporated | Hygienic medical devices having hydrophilic coating |
Families Citing this family (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN110694118A (en) * | 2019-09-23 | 2020-01-17 | 江苏理工学院 | Antibacterial and anticoagulant ventricles and abdominocentesis shunt tube silica gel tube body and preparation method and application thereof |
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US5804318A (en) * | 1995-10-26 | 1998-09-08 | Corvita Corporation | Lubricious hydrogel surface modification |
US5837008A (en) * | 1993-04-26 | 1998-11-17 | Medtronic, Inc. | Intravascular stent and method |
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US5091205A (en) * | 1989-01-17 | 1992-02-25 | Union Carbide Chemicals & Plastics Technology Corporation | Hydrophilic lubricious coatings |
CA2007743A1 (en) * | 1989-01-26 | 1990-07-26 | Sachiko Hattori | Vascular catheter with durable lubricious coating |
US5503631A (en) * | 1992-10-09 | 1996-04-02 | Terumo Kabushiki Kaisha | Lubricious catheter balloon for vasodilation |
US5772609A (en) * | 1993-05-11 | 1998-06-30 | Target Therapeutics, Inc. | Guidewire with variable flexibility due to polymeric coatings |
DE19713214A1 (en) * | 1997-03-28 | 1998-12-10 | Ruebben Alexander Dr Med | Covered stent, e.g. for treating vascular stenosis or aneurysms |
-
2000
- 2000-11-15 EP EP00978657A patent/EP1233724A4/en not_active Withdrawn
- 2000-11-15 WO PCT/US2000/031314 patent/WO2001036008A2/en not_active Application Discontinuation
- 2000-11-15 AU AU16097/01A patent/AU1609701A/en not_active Abandoned
Patent Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
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US5837008A (en) * | 1993-04-26 | 1998-11-17 | Medtronic, Inc. | Intravascular stent and method |
US5804318A (en) * | 1995-10-26 | 1998-09-08 | Corvita Corporation | Lubricious hydrogel surface modification |
Non-Patent Citations (1)
Title |
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See also references of EP1233724A2 * |
Cited By (15)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US7265199B2 (en) | 2000-04-11 | 2007-09-04 | Celonova Biosciences Germany Gmbh | Poly-tri-fluoro-ethoxypolyphosphazene coverings and films |
US9080146B2 (en) | 2001-01-11 | 2015-07-14 | Celonova Biosciences, Inc. | Substrates containing polyphosphazene as matrices and substrates containing polyphosphazene with a micro-structured surface |
US7771468B2 (en) | 2001-03-16 | 2010-08-10 | Angiotech Biocoatings Corp. | Medicated stent having multi-layer polymer coating |
US8287590B2 (en) | 2001-03-16 | 2012-10-16 | Angiotech Biocoatings Corp. | Medicated stent having multi-layer polymer coating |
US8101275B2 (en) | 2001-08-17 | 2012-01-24 | Celonova Biosciences, Inc. | Device based on nitinol, a process for its production, and its use |
DE10202467A1 (en) * | 2002-01-23 | 2003-07-24 | Polyzenix Gmbh | Device, useful as an artificial implant, comprises a substrate based on nitinol having at least a partial coating of a phosphazene polymer. |
WO2004052420A3 (en) * | 2002-12-06 | 2004-07-22 | Surmodics Inc | Barriers for bioactive agent-containing polymeric coatings |
WO2004052420A2 (en) * | 2002-12-06 | 2004-06-24 | Surmodics, Inc. | Barriers for bioactive agent-containing polymeric coatings |
US9107850B2 (en) | 2004-10-25 | 2015-08-18 | Celonova Biosciences, Inc. | Color-coded and sized loadable polymeric particles for therapeutic and/or diagnostic applications and methods of preparing and using the same |
US9114162B2 (en) | 2004-10-25 | 2015-08-25 | Celonova Biosciences, Inc. | Loadable polymeric particles for enhanced imaging in clinical applications and methods of preparing and using the same |
US9597419B2 (en) | 2004-10-25 | 2017-03-21 | Boston Scientific Limited | Loadable polymeric particles for enhanced imaging in clinical applications and methods of preparing and using the same |
US10973770B2 (en) | 2004-10-25 | 2021-04-13 | Varian Medical Systems, Inc. | Color-coded and sized loadable polymeric particles for therapeutic and/or diagnostic applications and methods of preparing and using the same |
US7922764B2 (en) | 2006-10-10 | 2011-04-12 | Celonova Bioscience, Inc. | Bioprosthetic heart valve with polyphosphazene |
US11167064B2 (en) | 2016-07-14 | 2021-11-09 | Hollister Incorporated | Hygienic medical devices having hydrophilic coating |
CN110180038A (en) * | 2019-06-21 | 2019-08-30 | 西南大学 | Has the kirsite vascular stent material of drug slow release function superhigh-flexibility coating |
Also Published As
Publication number | Publication date |
---|---|
WO2001036008A3 (en) | 2001-12-13 |
AU1609701A (en) | 2001-05-30 |
EP1233724A4 (en) | 2004-03-10 |
EP1233724A2 (en) | 2002-08-28 |
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