WO2008031596A1 - Coating formulation for medical coating - Google Patents
Coating formulation for medical coating Download PDFInfo
- Publication number
- WO2008031596A1 WO2008031596A1 PCT/EP2007/007985 EP2007007985W WO2008031596A1 WO 2008031596 A1 WO2008031596 A1 WO 2008031596A1 EP 2007007985 W EP2007007985 W EP 2007007985W WO 2008031596 A1 WO2008031596 A1 WO 2008031596A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- coating
- medical
- coating formulation
- poly
- hydrophilic
- Prior art date
Links
- 238000000576 coating method Methods 0.000 title claims abstract description 157
- 239000011248 coating agent Substances 0.000 title claims abstract description 133
- 239000008199 coating composition Substances 0.000 title claims abstract description 87
- 150000001875 compounds Chemical class 0.000 claims abstract description 66
- 239000003999 initiator Substances 0.000 claims abstract description 24
- 239000001257 hydrogen Substances 0.000 claims abstract description 15
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 15
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 11
- 125000005842 heteroatom Chemical group 0.000 claims abstract description 7
- 229930195733 hydrocarbon Natural products 0.000 claims abstract description 7
- 125000000524 functional group Chemical group 0.000 claims abstract description 5
- 150000002430 hydrocarbons Chemical class 0.000 claims abstract description 4
- 239000000203 mixture Substances 0.000 claims description 46
- 229920001223 polyethylene glycol Polymers 0.000 claims description 34
- 229920000642 polymer Polymers 0.000 claims description 31
- 229920000867 polyelectrolyte Polymers 0.000 claims description 26
- 238000009472 formulation Methods 0.000 claims description 25
- -1 polyoxazolidones Polymers 0.000 claims description 24
- 238000009736 wetting Methods 0.000 claims description 19
- 239000000758 substrate Substances 0.000 claims description 18
- 229920001477 hydrophilic polymer Polymers 0.000 claims description 17
- 229920001002 functional polymer Polymers 0.000 claims description 16
- 239000004094 surface-active agent Substances 0.000 claims description 14
- 239000012530 fluid Substances 0.000 claims description 13
- 238000000034 method Methods 0.000 claims description 12
- 229920001577 copolymer Polymers 0.000 claims description 11
- 150000008040 ionic compounds Chemical class 0.000 claims description 11
- 102000004196 processed proteins & peptides Human genes 0.000 claims description 11
- 108090000765 processed proteins & peptides Proteins 0.000 claims description 11
- 150000003839 salts Chemical class 0.000 claims description 11
- 229920001184 polypeptide Polymers 0.000 claims description 9
- 229920000728 polyester Polymers 0.000 claims description 8
- 229920002873 Polyethylenimine Polymers 0.000 claims description 7
- 229920000570 polyether Polymers 0.000 claims description 7
- 239000004952 Polyamide Substances 0.000 claims description 6
- 239000002798 polar solvent Substances 0.000 claims description 6
- 229920002647 polyamide Polymers 0.000 claims description 6
- 229920002635 polyurethane Polymers 0.000 claims description 6
- 239000004814 polyurethane Substances 0.000 claims description 6
- 239000002202 Polyethylene glycol Substances 0.000 claims description 5
- 239000012528 membrane Substances 0.000 claims description 5
- 229920002451 polyvinyl alcohol Polymers 0.000 claims description 5
- 235000019422 polyvinyl alcohol Nutrition 0.000 claims description 5
- 102000008186 Collagen Human genes 0.000 claims description 4
- 108010035532 Collagen Proteins 0.000 claims description 4
- 150000003926 acrylamides Chemical class 0.000 claims description 4
- 229920001436 collagen Polymers 0.000 claims description 4
- 230000005670 electromagnetic radiation Effects 0.000 claims description 4
- 150000004676 glycans Chemical class 0.000 claims description 4
- 229920001282 polysaccharide Polymers 0.000 claims description 4
- 239000005017 polysaccharide Substances 0.000 claims description 4
- 159000000000 sodium salts Chemical class 0.000 claims description 4
- 125000003837 (C1-C20) alkyl group Chemical group 0.000 claims description 3
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims description 3
- 239000004215 Carbon black (E152) Substances 0.000 claims description 3
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims description 3
- 229910019142 PO4 Inorganic materials 0.000 claims description 3
- 229920002472 Starch Polymers 0.000 claims description 3
- 229920006397 acrylic thermoplastic Polymers 0.000 claims description 3
- 239000001913 cellulose Substances 0.000 claims description 3
- 229920002678 cellulose Polymers 0.000 claims description 3
- 229920000371 poly(diallyldimethylammonium chloride) polymer Polymers 0.000 claims description 3
- 229920003229 poly(methyl methacrylate) Polymers 0.000 claims description 3
- 229920000647 polyepoxide Polymers 0.000 claims description 3
- 229920001451 polypropylene glycol Polymers 0.000 claims description 3
- 102000004169 proteins and genes Human genes 0.000 claims description 3
- 108090000623 proteins and genes Proteins 0.000 claims description 3
- 239000008107 starch Substances 0.000 claims description 3
- 235000019698 starch Nutrition 0.000 claims description 3
- ISXSCDLOGDJUNJ-UHFFFAOYSA-N tert-butyl prop-2-enoate Chemical compound CC(C)(C)OC(=O)C=C ISXSCDLOGDJUNJ-UHFFFAOYSA-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
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 2
- 102000009027 Albumins Human genes 0.000 claims description 2
- 108010088751 Albumins Proteins 0.000 claims description 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 claims description 2
- 229920002134 Carboxymethyl cellulose Polymers 0.000 claims description 2
- 229920002101 Chitin Polymers 0.000 claims description 2
- 229920001661 Chitosan Polymers 0.000 claims description 2
- 229920002307 Dextran Polymers 0.000 claims description 2
- 102000016942 Elastin Human genes 0.000 claims description 2
- 108010014258 Elastin Proteins 0.000 claims description 2
- 102000009123 Fibrin Human genes 0.000 claims description 2
- 108010073385 Fibrin Proteins 0.000 claims description 2
- 108010010803 Gelatin Proteins 0.000 claims description 2
- 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 2
- 229920002153 Hydroxypropyl cellulose Polymers 0.000 claims description 2
- 108091034117 Oligonucleotide Proteins 0.000 claims description 2
- 102000015636 Oligopeptides Human genes 0.000 claims description 2
- 108010038807 Oligopeptides Proteins 0.000 claims description 2
- 229920003171 Poly (ethylene oxide) Polymers 0.000 claims description 2
- 229920002845 Poly(methacrylic acid) Polymers 0.000 claims description 2
- 229920000691 Poly[bis(2-chloroethyl) ether-alt-1,3-bis[3-(dimethylamino)propyl]urea] Polymers 0.000 claims description 2
- 229920002732 Polyanhydride Polymers 0.000 claims description 2
- 229920000954 Polyglycolide Polymers 0.000 claims description 2
- 239000004372 Polyvinyl alcohol Substances 0.000 claims description 2
- 229920002125 Sokalan® Polymers 0.000 claims description 2
- JLCPHMBAVCMARE-UHFFFAOYSA-N [3-[[3-[[3-[[3-[[3-[[3-[[3-[[3-[[3-[[3-[[3-[[5-(2-amino-6-oxo-1H-purin-9-yl)-3-[[3-[[3-[[3-[[3-[[3-[[5-(2-amino-6-oxo-1H-purin-9-yl)-3-[[5-(2-amino-6-oxo-1H-purin-9-yl)-3-hydroxyoxolan-2-yl]methoxy-hydroxyphosphoryl]oxyoxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(6-aminopurin-9-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(6-aminopurin-9-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(6-aminopurin-9-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(6-aminopurin-9-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxyoxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(4-amino-2-oxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(6-aminopurin-9-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(6-aminopurin-9-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(4-amino-2-oxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(4-amino-2-oxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(4-amino-2-oxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(6-aminopurin-9-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(4-amino-2-oxopyrimidin-1-yl)oxolan-2-yl]methyl [5-(6-aminopurin-9-yl)-2-(hydroxymethyl)oxolan-3-yl] hydrogen phosphate Polymers Cc1cn(C2CC(OP(O)(=O)OCC3OC(CC3OP(O)(=O)OCC3OC(CC3O)n3cnc4c3nc(N)[nH]c4=O)n3cnc4c3nc(N)[nH]c4=O)C(COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3CO)n3cnc4c(N)ncnc34)n3ccc(N)nc3=O)n3cnc4c(N)ncnc34)n3ccc(N)nc3=O)n3ccc(N)nc3=O)n3ccc(N)nc3=O)n3cnc4c(N)ncnc34)n3cnc4c(N)ncnc34)n3cc(C)c(=O)[nH]c3=O)n3cc(C)c(=O)[nH]c3=O)n3ccc(N)nc3=O)n3cc(C)c(=O)[nH]c3=O)n3cnc4c3nc(N)[nH]c4=O)n3cnc4c(N)ncnc34)n3cnc4c(N)ncnc34)n3cnc4c(N)ncnc34)n3cnc4c(N)ncnc34)O2)c(=O)[nH]c1=O JLCPHMBAVCMARE-UHFFFAOYSA-N 0.000 claims description 2
- 239000002253 acid Substances 0.000 claims description 2
- 150000007513 acids Chemical class 0.000 claims description 2
- 230000003213 activating effect Effects 0.000 claims description 2
- 229920000615 alginic acid Polymers 0.000 claims description 2
- 235000010443 alginic acid Nutrition 0.000 claims description 2
- 235000019270 ammonium chloride Nutrition 0.000 claims description 2
- 239000001768 carboxy methyl cellulose Substances 0.000 claims description 2
- 235000010948 carboxy methyl cellulose Nutrition 0.000 claims description 2
- 239000008112 carboxymethyl-cellulose Substances 0.000 claims description 2
- 229920002549 elastin Polymers 0.000 claims description 2
- UYMKPFRHYYNDTL-UHFFFAOYSA-N ethenamine Chemical class NC=C UYMKPFRHYYNDTL-UHFFFAOYSA-N 0.000 claims description 2
- 229920000159 gelatin Polymers 0.000 claims description 2
- 239000008273 gelatin Substances 0.000 claims description 2
- 235000019322 gelatine Nutrition 0.000 claims description 2
- 235000011852 gelatine desserts Nutrition 0.000 claims description 2
- 229920000669 heparin Polymers 0.000 claims description 2
- 229960002897 heparin Drugs 0.000 claims description 2
- 229920002674 hyaluronan Polymers 0.000 claims description 2
- 229960003160 hyaluronic acid Drugs 0.000 claims description 2
- 229920003063 hydroxymethyl cellulose Polymers 0.000 claims description 2
- 229940031574 hydroxymethyl cellulose Drugs 0.000 claims description 2
- 239000001863 hydroxypropyl cellulose Substances 0.000 claims description 2
- 235000010977 hydroxypropyl cellulose Nutrition 0.000 claims description 2
- 229910052740 iodine Inorganic materials 0.000 claims description 2
- 239000011630 iodine Substances 0.000 claims description 2
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 claims description 2
- 229920000609 methyl cellulose Polymers 0.000 claims description 2
- 239000001923 methylcellulose Substances 0.000 claims description 2
- 235000010981 methylcellulose Nutrition 0.000 claims description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims description 2
- 239000010452 phosphate Substances 0.000 claims description 2
- 229920000747 poly(lactic acid) Polymers 0.000 claims description 2
- 229920002627 poly(phosphazenes) Polymers 0.000 claims description 2
- 229920001464 poly(sodium 4-styrenesulfonate) Polymers 0.000 claims description 2
- 239000004584 polyacrylic acid Substances 0.000 claims description 2
- 229920001610 polycaprolactone Polymers 0.000 claims description 2
- 229920000656 polylysine Polymers 0.000 claims description 2
- 229920001289 polyvinyl ether Polymers 0.000 claims description 2
- 150000003222 pyridines Chemical class 0.000 claims description 2
- 229920002554 vinyl polymer Polymers 0.000 claims description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 30
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 24
- 238000002474 experimental method Methods 0.000 description 20
- 238000012360 testing method Methods 0.000 description 20
- 230000000052 comparative effect Effects 0.000 description 19
- 239000002987 primer (paints) Substances 0.000 description 19
- WTFAGPBUAGFMQX-UHFFFAOYSA-N 1-[2-[2-(2-aminopropoxy)propoxy]propoxy]propan-2-amine Chemical compound CC(N)COCC(C)OCC(C)OCC(C)N WTFAGPBUAGFMQX-UHFFFAOYSA-N 0.000 description 18
- 230000015572 biosynthetic process Effects 0.000 description 18
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 14
- 239000007788 liquid Substances 0.000 description 13
- 238000006243 chemical reaction Methods 0.000 description 12
- 238000001723 curing Methods 0.000 description 12
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 11
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 11
- 238000003786 synthesis reaction Methods 0.000 description 11
- 239000010410 layer Substances 0.000 description 10
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- 238000005481 NMR spectroscopy Methods 0.000 description 8
- 239000002609 medium Substances 0.000 description 8
- 239000000243 solution Substances 0.000 description 8
- 239000000126 substance Substances 0.000 description 8
- 239000003814 drug Substances 0.000 description 7
- 238000003384 imaging method Methods 0.000 description 7
- 241000894007 species Species 0.000 description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- HFBMWMNUJJDEQZ-UHFFFAOYSA-N acryloyl chloride Chemical compound ClC(=O)C=C HFBMWMNUJJDEQZ-UHFFFAOYSA-N 0.000 description 6
- 150000004985 diamines Chemical class 0.000 description 6
- 229910021645 metal ion Inorganic materials 0.000 description 6
- 239000011541 reaction mixture Substances 0.000 description 6
- 230000008093 supporting effect Effects 0.000 description 6
- QAEDZJGFFMLHHQ-UHFFFAOYSA-N trifluoroacetic anhydride Chemical compound FC(F)(F)C(=O)OC(=O)C(F)(F)F QAEDZJGFFMLHHQ-UHFFFAOYSA-N 0.000 description 6
- 239000000463 material Substances 0.000 description 5
- 210000001519 tissue Anatomy 0.000 description 5
- 229940086542 triethylamine Drugs 0.000 description 5
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 4
- 238000004113 cell culture Methods 0.000 description 4
- 229940079593 drug Drugs 0.000 description 4
- 238000005259 measurement Methods 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 150000003254 radicals Chemical class 0.000 description 4
- FVEFRICMTUKAML-UHFFFAOYSA-M sodium tetradecyl sulfate Chemical compound [Na+].CCCCC(CC)CCC(CC(C)C)OS([O-])(=O)=O FVEFRICMTUKAML-UHFFFAOYSA-M 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 238000005160 1H NMR spectroscopy Methods 0.000 description 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- XMLYCEVDHLAQEL-UHFFFAOYSA-N 2-hydroxy-2-methyl-1-phenylpropan-1-one Chemical compound CC(C)(O)C(=O)C1=CC=CC=C1 XMLYCEVDHLAQEL-UHFFFAOYSA-N 0.000 description 3
- VVBLNCFGVYUYGU-UHFFFAOYSA-N 4,4'-Bis(dimethylamino)benzophenone Chemical compound C1=CC(N(C)C)=CC=C1C(=O)C1=CC=C(N(C)C)C=C1 VVBLNCFGVYUYGU-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 238000010546 Norrish type I reaction Methods 0.000 description 3
- 239000004721 Polyphenylene oxide Substances 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 3
- 239000004599 antimicrobial Substances 0.000 description 3
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 3
- 239000012965 benzophenone Substances 0.000 description 3
- 210000004027 cell Anatomy 0.000 description 3
- UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 3
- 238000003618 dip coating Methods 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 239000012632 extractable Substances 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 239000007943 implant Substances 0.000 description 3
- 230000001976 improved effect Effects 0.000 description 3
- 238000011534 incubation Methods 0.000 description 3
- 238000003780 insertion Methods 0.000 description 3
- 230000037431 insertion Effects 0.000 description 3
- 229920000831 ionic polymer Polymers 0.000 description 3
- 239000012633 leachable Substances 0.000 description 3
- 229920002521 macromolecule Polymers 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 239000012299 nitrogen atmosphere Substances 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- 230000000399 orthopedic effect Effects 0.000 description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
- 229920003023 plastic Polymers 0.000 description 3
- 239000004033 plastic Substances 0.000 description 3
- UFUASNAHBMBJIX-UHFFFAOYSA-N propan-1-one Chemical compound CC[C]=O UFUASNAHBMBJIX-UHFFFAOYSA-N 0.000 description 3
- 238000000926 separation method Methods 0.000 description 3
- 238000013112 stability test Methods 0.000 description 3
- 0 *C(C(N(*)C=I)=O)=C Chemical compound *C(C(N(*)C=I)=O)=C 0.000 description 2
- KWVGIHKZDCUPEU-UHFFFAOYSA-N 2,2-dimethoxy-2-phenylacetophenone Chemical compound C=1C=CC=CC=1C(OC)(OC)C(=O)C1=CC=CC=C1 KWVGIHKZDCUPEU-UHFFFAOYSA-N 0.000 description 2
- VFBJXXJYHWLXRM-UHFFFAOYSA-N 2-[2-[3-(3,5-ditert-butyl-4-hydroxyphenyl)propanoyloxy]ethylsulfanyl]ethyl 3-(3,5-ditert-butyl-4-hydroxyphenyl)propanoate Chemical compound CC(C)(C)C1=C(O)C(C(C)(C)C)=CC(CCC(=O)OCCSCCOC(=O)CCC=2C=C(C(O)=C(C=2)C(C)(C)C)C(C)(C)C)=C1 VFBJXXJYHWLXRM-UHFFFAOYSA-N 0.000 description 2
- LZZYPRNAOMGNLH-UHFFFAOYSA-M Cetrimonium bromide Chemical compound [Br-].CCCCCCCCCCCCCCCC[N+](C)(C)C LZZYPRNAOMGNLH-UHFFFAOYSA-M 0.000 description 2
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical group C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- 208000012902 Nervous system disease Diseases 0.000 description 2
- 208000025966 Neurological disease Diseases 0.000 description 2
- DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 2
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 239000013543 active substance Substances 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 230000000845 anti-microbial effect Effects 0.000 description 2
- 230000002965 anti-thrombogenic effect Effects 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 238000000149 argon plasma sintering Methods 0.000 description 2
- 239000012298 atmosphere Substances 0.000 description 2
- 150000008366 benzophenones Chemical class 0.000 description 2
- 208000014117 bile duct papillary neoplasm Diseases 0.000 description 2
- 230000015556 catabolic process Effects 0.000 description 2
- 238000012512 characterization method Methods 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 239000003086 colorant Substances 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- 238000006731 degradation reaction Methods 0.000 description 2
- KXGVEGMKQFWNSR-LLQZFEROSA-N deoxycholic acid Chemical compound C([C@H]1CC2)[C@H](O)CC[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CC[C@H]([C@@H](CCC(O)=O)C)[C@@]2(C)[C@@H](O)C1 KXGVEGMKQFWNSR-LLQZFEROSA-N 0.000 description 2
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 2
- VFHVQBAGLAREND-UHFFFAOYSA-N diphenylphosphoryl-(2,4,6-trimethylphenyl)methanone Chemical compound CC1=CC(C)=CC(C)=C1C(=O)P(=O)(C=1C=CC=CC=1)C1=CC=CC=C1 VFHVQBAGLAREND-UHFFFAOYSA-N 0.000 description 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 2
- SYELZBGXAIXKHU-UHFFFAOYSA-N dodecyldimethylamine N-oxide Chemical compound CCCCCCCCCCCC[N+](C)(C)[O-] SYELZBGXAIXKHU-UHFFFAOYSA-N 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 230000002526 effect on cardiovascular system Effects 0.000 description 2
- 239000000839 emulsion Substances 0.000 description 2
- 230000002349 favourable effect Effects 0.000 description 2
- 239000012949 free radical photoinitiator Substances 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 230000010354 integration Effects 0.000 description 2
- 239000002563 ionic surfactant Substances 0.000 description 2
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 2
- 239000000314 lubricant Substances 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 239000000178 monomer Substances 0.000 description 2
- 239000002736 nonionic surfactant Substances 0.000 description 2
- 229920002113 octoxynol Polymers 0.000 description 2
- 235000021317 phosphate Nutrition 0.000 description 2
- 239000000049 pigment Substances 0.000 description 2
- 229920000671 polyethylene glycol diacrylate Polymers 0.000 description 2
- IOLCXVTUBQKXJR-UHFFFAOYSA-M potassium bromide Chemical compound [K+].[Br-] IOLCXVTUBQKXJR-UHFFFAOYSA-M 0.000 description 2
- 230000008569 process Effects 0.000 description 2
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 2
- 230000005855 radiation Effects 0.000 description 2
- 238000011160 research Methods 0.000 description 2
- 238000001223 reverse osmosis Methods 0.000 description 2
- 150000003333 secondary alcohols Chemical class 0.000 description 2
- 229920005573 silicon-containing polymer Polymers 0.000 description 2
- 229940083575 sodium dodecyl sulfate Drugs 0.000 description 2
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 238000001228 spectrum Methods 0.000 description 2
- 239000003381 stabilizer Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 238000001356 surgical procedure Methods 0.000 description 2
- 238000004448 titration Methods 0.000 description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- GPRLSGONYQIRFK-MNYXATJNSA-N triton Chemical compound [3H+] GPRLSGONYQIRFK-MNYXATJNSA-N 0.000 description 2
- 230000002485 urinary effect Effects 0.000 description 2
- 230000002792 vascular Effects 0.000 description 2
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 2
- JNELGWHKGNBSMD-UHFFFAOYSA-N xanthone Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3OC2=C1 JNELGWHKGNBSMD-UHFFFAOYSA-N 0.000 description 2
- GRDGBWVSVMLKBV-UHFFFAOYSA-N (2-amino-5-nitrophenyl)-(2-chlorophenyl)methanone Chemical compound NC1=CC=C([N+]([O-])=O)C=C1C(=O)C1=CC=CC=C1Cl GRDGBWVSVMLKBV-UHFFFAOYSA-N 0.000 description 1
- CKGKXGQVRVAKEA-UHFFFAOYSA-N (2-methylphenyl)-phenylmethanone Chemical class CC1=CC=CC=C1C(=O)C1=CC=CC=C1 CKGKXGQVRVAKEA-UHFFFAOYSA-N 0.000 description 1
- WXPWZZHELZEVPO-UHFFFAOYSA-N (4-methylphenyl)-phenylmethanone Chemical compound C1=CC(C)=CC=C1C(=O)C1=CC=CC=C1 WXPWZZHELZEVPO-UHFFFAOYSA-N 0.000 description 1
- JDPDLMITLVAWKZ-UHFFFAOYSA-N 1,3-dioxolan-4-yl(phenyl)methanone Chemical class C=1C=CC=CC=1C(=O)C1COCO1 JDPDLMITLVAWKZ-UHFFFAOYSA-N 0.000 description 1
- ILBBNQMSDGAAPF-UHFFFAOYSA-N 1-(6-hydroxy-6-methylcyclohexa-2,4-dien-1-yl)propan-1-one Chemical compound CCC(=O)C1C=CC=CC1(C)O ILBBNQMSDGAAPF-UHFFFAOYSA-N 0.000 description 1
- 239000012956 1-hydroxycyclohexylphenyl-ketone Substances 0.000 description 1
- YIKSHDNOAYSSPX-UHFFFAOYSA-N 1-propan-2-ylthioxanthen-9-one Chemical compound S1C2=CC=CC=C2C(=O)C2=C1C=CC=C2C(C)C YIKSHDNOAYSSPX-UHFFFAOYSA-N 0.000 description 1
- OBETXYAYXDNJHR-UHFFFAOYSA-N 2-Ethylhexanoic acid Chemical compound CCCCC(CC)C(O)=O OBETXYAYXDNJHR-UHFFFAOYSA-N 0.000 description 1
- GJKGAPPUXSSCFI-UHFFFAOYSA-N 2-Hydroxy-4'-(2-hydroxyethoxy)-2-methylpropiophenone Chemical compound CC(C)(O)C(=O)C1=CC=C(OCCO)C=C1 GJKGAPPUXSSCFI-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- UHFFVFAKEGKNAQ-UHFFFAOYSA-N 2-benzyl-2-(dimethylamino)-1-(4-morpholin-4-ylphenyl)butan-1-one Chemical compound C=1C=C(N2CCOCC2)C=CC=1C(=O)C(CC)(N(C)C)CC1=CC=CC=C1 UHFFVFAKEGKNAQ-UHFFFAOYSA-N 0.000 description 1
- SJEBAWHUJDUKQK-UHFFFAOYSA-N 2-ethylanthraquinone Chemical compound C1=CC=C2C(=O)C3=CC(CC)=CC=C3C(=O)C2=C1 SJEBAWHUJDUKQK-UHFFFAOYSA-N 0.000 description 1
- MEYARNKYUHUVBB-UHFFFAOYSA-N 2-hydroxy-1-[2-(hydroxymethyl)phenyl]-2-phenylethanone Chemical compound OCC1=CC=CC=C1C(=O)C(O)C1=CC=CC=C1 MEYARNKYUHUVBB-UHFFFAOYSA-N 0.000 description 1
- OMIGHNLMNHATMP-UHFFFAOYSA-N 2-hydroxyethyl prop-2-enoate Chemical compound OCCOC(=O)C=C OMIGHNLMNHATMP-UHFFFAOYSA-N 0.000 description 1
- LWRBVKNFOYUCNP-UHFFFAOYSA-N 2-methyl-1-(4-methylsulfanylphenyl)-2-morpholin-4-ylpropan-1-one Chemical compound C1=CC(SC)=CC=C1C(=O)C(C)(C)N1CCOCC1 LWRBVKNFOYUCNP-UHFFFAOYSA-N 0.000 description 1
- RIWRBSMFKVOJMN-UHFFFAOYSA-N 2-methyl-1-phenylpropan-2-ol Chemical compound CC(C)(O)CC1=CC=CC=C1 RIWRBSMFKVOJMN-UHFFFAOYSA-N 0.000 description 1
- KTALPKYXQZGAEG-UHFFFAOYSA-N 2-propan-2-ylthioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC(C(C)C)=CC=C3SC2=C1 KTALPKYXQZGAEG-UHFFFAOYSA-N 0.000 description 1
- GOLORTLGFDVFDW-UHFFFAOYSA-N 3-(1h-benzimidazol-2-yl)-7-(diethylamino)chromen-2-one Chemical compound C1=CC=C2NC(C3=CC4=CC=C(C=C4OC3=O)N(CC)CC)=NC2=C1 GOLORTLGFDVFDW-UHFFFAOYSA-N 0.000 description 1
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 1
- SAIKULLUBZKPDA-UHFFFAOYSA-N Bis(2-ethylhexyl) amine Chemical compound CCCCC(CC)CNCC(CC)CCCC SAIKULLUBZKPDA-UHFFFAOYSA-N 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- 229920002799 BoPET Polymers 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 239000009261 D 400 Substances 0.000 description 1
- 206010019280 Heart failures Diseases 0.000 description 1
- 238000012565 NMR experiment Methods 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical group [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- 229920001213 Polysorbate 20 Polymers 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 1
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 1
- 229920013806 TRITON CG-110 Polymers 0.000 description 1
- 229920013814 TRITON N-57 Polymers 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- 238000005411 Van der Waals force Methods 0.000 description 1
- LFOXEOLGJPJZAA-UHFFFAOYSA-N [(2,6-dimethoxybenzoyl)-(2,4,4-trimethylpentyl)phosphoryl]-(2,6-dimethoxyphenyl)methanone Chemical compound COC1=CC=CC(OC)=C1C(=O)P(=O)(CC(C)CC(C)(C)C)C(=O)C1=C(OC)C=CC=C1OC LFOXEOLGJPJZAA-UHFFFAOYSA-N 0.000 description 1
- GUCYFKSBFREPBC-UHFFFAOYSA-N [phenyl-(2,4,6-trimethylbenzoyl)phosphoryl]-(2,4,6-trimethylphenyl)methanone Chemical compound CC1=CC(C)=CC(C)=C1C(=O)P(=O)(C=1C=CC=CC=1)C(=O)C1=C(C)C=C(C)C=C1C GUCYFKSBFREPBC-UHFFFAOYSA-N 0.000 description 1
- 238000005299 abrasion Methods 0.000 description 1
- 239000006096 absorbing agent Substances 0.000 description 1
- 230000001133 acceleration Effects 0.000 description 1
- 150000008062 acetophenones Chemical class 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 229910001413 alkali metal ion Inorganic materials 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O ammonium group Chemical group [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- 238000002399 angioplasty Methods 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 239000003945 anionic surfactant Substances 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 238000000137 annealing Methods 0.000 description 1
- 150000004056 anthraquinones Chemical class 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- 150000008365 aromatic ketones Chemical class 0.000 description 1
- 238000003556 assay Methods 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- WURBFLDFSFBTLW-UHFFFAOYSA-N benzil Chemical compound C=1C=CC=CC=1C(=O)C(=O)C1=CC=CC=C1 WURBFLDFSFBTLW-UHFFFAOYSA-N 0.000 description 1
- ISAOCJYIOMOJEB-UHFFFAOYSA-N benzoin Chemical class C=1C=CC=CC=1C(O)C(=O)C1=CC=CC=C1 ISAOCJYIOMOJEB-UHFFFAOYSA-N 0.000 description 1
- 230000000975 bioactive effect Effects 0.000 description 1
- 230000008512 biological response Effects 0.000 description 1
- MQDJYUACMFCOFT-UHFFFAOYSA-N bis[2-(1-hydroxycyclohexyl)phenyl]methanone Chemical compound C=1C=CC=C(C(=O)C=2C(=CC=CC=2)C2(O)CCCCC2)C=1C1(O)CCCCC1 MQDJYUACMFCOFT-UHFFFAOYSA-N 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 210000001124 body fluid Anatomy 0.000 description 1
- 239000010839 body fluid Substances 0.000 description 1
- 238000010504 bond cleavage reaction Methods 0.000 description 1
- 210000000988 bone and bone Anatomy 0.000 description 1
- 239000000872 buffer Substances 0.000 description 1
- SHZIWNPUGXLXDT-UHFFFAOYSA-N caproic acid ethyl ester Natural products CCCCCC(=O)OCC SHZIWNPUGXLXDT-UHFFFAOYSA-N 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 150000007942 carboxylates Chemical group 0.000 description 1
- 210000000845 cartilage Anatomy 0.000 description 1
- 239000003093 cationic surfactant Substances 0.000 description 1
- 239000000919 ceramic Substances 0.000 description 1
- 210000001175 cerebrospinal fluid Anatomy 0.000 description 1
- PBAYDYUZOSNJGU-UHFFFAOYSA-N chelidonic acid Natural products OC(=O)C1=CC(=O)C=C(C(O)=O)O1 PBAYDYUZOSNJGU-UHFFFAOYSA-N 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 239000002131 composite material Substances 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000003851 corona treatment Methods 0.000 description 1
- 239000007822 coupling agent Substances 0.000 description 1
- 229920006037 cross link polymer Polymers 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 230000006378 damage Effects 0.000 description 1
- 238000006356 dehydrogenation reaction Methods 0.000 description 1
- 229940009976 deoxycholate Drugs 0.000 description 1
- 229960003964 deoxycholic acid Drugs 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- 206010012601 diabetes mellitus Diseases 0.000 description 1
- 238000000502 dialysis Methods 0.000 description 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
- 229940043279 diisopropylamine Drugs 0.000 description 1
- PODOEQVNFJSWIK-UHFFFAOYSA-N diphenylphosphoryl-(2,4,6-trimethoxyphenyl)methanone Chemical compound COC1=CC(OC)=CC(OC)=C1C(=O)P(=O)(C=1C=CC=CC=1)C1=CC=CC=C1 PODOEQVNFJSWIK-UHFFFAOYSA-N 0.000 description 1
- 238000007598 dipping method Methods 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000035475 disorder Diseases 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 238000010494 dissociation reaction Methods 0.000 description 1
- 230000005593 dissociations Effects 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 238000010894 electron beam technology Methods 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
- 230000002708 enhancing effect Effects 0.000 description 1
- 235000019439 ethyl acetate Nutrition 0.000 description 1
- 230000005281 excited state Effects 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000011888 foil Substances 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 210000003709 heart valve Anatomy 0.000 description 1
- 238000013007 heat curing Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 230000036571 hydration Effects 0.000 description 1
- 238000006703 hydration reaction Methods 0.000 description 1
- 239000000017 hydrogel Substances 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 230000005660 hydrophilic surface Effects 0.000 description 1
- 230000002209 hydrophobic effect Effects 0.000 description 1
- 230000005661 hydrophobic surface Effects 0.000 description 1
- BJRNKVDFDLYUGJ-RMPHRYRLSA-N hydroquinone O-beta-D-glucopyranoside Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1OC1=CC=C(O)C=C1 BJRNKVDFDLYUGJ-RMPHRYRLSA-N 0.000 description 1
- CBOIHMRHGLHBPB-UHFFFAOYSA-N hydroxymethyl Chemical compound O[CH2] CBOIHMRHGLHBPB-UHFFFAOYSA-N 0.000 description 1
- 210000001822 immobilized cell Anatomy 0.000 description 1
- 230000001900 immune effect Effects 0.000 description 1
- 230000028993 immune response Effects 0.000 description 1
- 238000002513 implantation Methods 0.000 description 1
- 238000000099 in vitro assay Methods 0.000 description 1
- 238000001727 in vivo Methods 0.000 description 1
- 208000015181 infectious disease Diseases 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 238000001802 infusion Methods 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 230000000977 initiatory effect Effects 0.000 description 1
- 229940030980 inova Drugs 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 125000003010 ionic group Chemical group 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 230000001788 irregular Effects 0.000 description 1
- 210000001503 joint Anatomy 0.000 description 1
- 239000002346 layers by function Substances 0.000 description 1
- 238000002386 leaching Methods 0.000 description 1
- 239000004611 light stabiliser Substances 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 238000005461 lubrication Methods 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 238000013160 medical therapy Methods 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- FQPSGWSUVKBHSU-UHFFFAOYSA-N methacrylamide Chemical compound CC(=C)C(N)=O FQPSGWSUVKBHSU-UHFFFAOYSA-N 0.000 description 1
- VHRYZQNGTZXDNX-UHFFFAOYSA-N methacryloyl chloride Chemical compound CC(=C)C(Cl)=O VHRYZQNGTZXDNX-UHFFFAOYSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- SNVLJLYUUXKWOJ-UHFFFAOYSA-N methylidenecarbene Chemical compound C=[C] SNVLJLYUUXKWOJ-UHFFFAOYSA-N 0.000 description 1
- 238000002324 minimally invasive surgery Methods 0.000 description 1
- CHDKQNHKDMEASZ-UHFFFAOYSA-N n-prop-2-enoylprop-2-enamide Chemical compound C=CC(=O)NC(=O)C=C CHDKQNHKDMEASZ-UHFFFAOYSA-N 0.000 description 1
- DYUWTXWIYMHBQS-UHFFFAOYSA-N n-prop-2-enylprop-2-en-1-amine Chemical compound C=CCNCC=C DYUWTXWIYMHBQS-UHFFFAOYSA-N 0.000 description 1
- 150000002823 nitrates Chemical class 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 229920000847 nonoxynol Polymers 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- BJRNKVDFDLYUGJ-UHFFFAOYSA-N p-hydroxyphenyl beta-D-alloside Natural products OC1C(O)C(O)C(CO)OC1OC1=CC=C(O)C=C1 BJRNKVDFDLYUGJ-UHFFFAOYSA-N 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 230000037361 pathway Effects 0.000 description 1
- 239000008188 pellet Substances 0.000 description 1
- 230000035699 permeability Effects 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 239000008363 phosphate buffer Substances 0.000 description 1
- 125000002467 phosphate group Chemical group [H]OP(=O)(O[H])O[*] 0.000 description 1
- 125000005496 phosphonium group Chemical group 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 238000004375 physisorption Methods 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- 238000009832 plasma treatment Methods 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229920000058 polyacrylate Polymers 0.000 description 1
- 229920006393 polyether sulfone Polymers 0.000 description 1
- 229920000139 polyethylene terephthalate Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 229920000098 polyolefin Polymers 0.000 description 1
- 239000000256 polyoxyethylene sorbitan monolaurate Substances 0.000 description 1
- 235000010486 polyoxyethylene sorbitan monolaurate Nutrition 0.000 description 1
- 235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 description 1
- 229920000053 polysorbate 80 Polymers 0.000 description 1
- 229920006295 polythiol Polymers 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical group CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 125000001453 quaternary ammonium group Chemical group 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- 238000003847 radiation curing Methods 0.000 description 1
- 230000027756 respiratory electron transport chain Effects 0.000 description 1
- 230000033764 rhythmic process Effects 0.000 description 1
- 230000011664 signaling Effects 0.000 description 1
- 229910000077 silane Inorganic materials 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 150000003384 small molecules Chemical class 0.000 description 1
- 238000002791 soaking Methods 0.000 description 1
- NRHMKIHPTBHXPF-TUJRSCDTSA-M sodium cholate Chemical compound [Na+].C([C@H]1C[C@H]2O)[C@H](O)CC[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CC[C@H]([C@@H](CCC([O-])=O)C)[C@@]2(C)[C@@H](O)C1 NRHMKIHPTBHXPF-TUJRSCDTSA-M 0.000 description 1
- APSBXTVYXVQYAB-UHFFFAOYSA-M sodium docusate Chemical compound [Na+].CCCCC(CC)COC(=O)CC(S([O-])(=O)=O)C(=O)OCC(CC)CCCC APSBXTVYXVQYAB-UHFFFAOYSA-M 0.000 description 1
- ADWNFGORSPBALY-UHFFFAOYSA-M sodium;2-[dodecyl(methyl)amino]acetate Chemical compound [Na+].CCCCCCCCCCCCN(C)CC([O-])=O ADWNFGORSPBALY-UHFFFAOYSA-M 0.000 description 1
- 210000004872 soft tissue Anatomy 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 230000001954 sterilising effect Effects 0.000 description 1
- 238000004659 sterilization and disinfection Methods 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L sulfate group Chemical group S(=O)(=O)([O-])[O-] QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- RWSOTUBLDIXVET-UHFFFAOYSA-O sulfonium group Chemical group [SH3+] RWSOTUBLDIXVET-UHFFFAOYSA-O 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 238000004381 surface treatment Methods 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 150000003568 thioethers Chemical class 0.000 description 1
- YRHRIQCWCFGUEQ-UHFFFAOYSA-N thioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3SC2=C1 YRHRIQCWCFGUEQ-UHFFFAOYSA-N 0.000 description 1
- 230000000451 tissue damage Effects 0.000 description 1
- 231100000827 tissue damage Toxicity 0.000 description 1
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 238000007740 vapor deposition Methods 0.000 description 1
- 208000019553 vascular disease Diseases 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 150000007964 xanthones Chemical class 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
- 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
- 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
- A61L29/00—Materials for catheters, medical tubing, cannulae, or endoscopes or for coating catheters
- A61L29/08—Materials for coatings
- A61L29/10—Inorganic 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
- 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
-
- 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
-
- 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
- C08G65/331—Polymers modified by chemical after-treatment with organic compounds containing oxygen
- C08G65/332—Polymers modified by chemical after-treatment with organic compounds containing oxygen containing carboxyl groups, or halides, or esters thereof
- C08G65/3322—Polymers modified by chemical after-treatment with organic compounds containing oxygen containing carboxyl groups, or halides, or esters thereof acyclic
-
- 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
- C08G65/3332—Polymers modified by chemical after-treatment with organic compounds containing nitrogen containing carboxamide group
- C08G65/33324—Polymers modified by chemical after-treatment with organic compounds containing nitrogen containing carboxamide group acyclic
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L33/00—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides or nitriles thereof; Compositions of derivatives of such polymers
- C08L33/24—Homopolymers or copolymers of amides or imides
- C08L33/26—Homopolymers or copolymers of acrylamide or methacrylamide
-
- 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
- C09D135/00—Coating compositions based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a carboxyl radical, and containing at least another carboxyl radical in the molecule, or of salts, anhydrides, esters, amides, imides or nitriles thereof; Coating compositions based on derivatives of such polymers
-
- 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
- C09D135/00—Coating compositions based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a carboxyl radical, and containing at least another carboxyl radical in the molecule, or of salts, anhydrides, esters, amides, imides or nitriles thereof; Coating compositions based on derivatives of such polymers
- C09D135/02—Homopolymers or copolymers of esters
-
- 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
- C09D4/00—Coating compositions, e.g. paints, varnishes or lacquers, based on organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond ; Coating compositions, based on monomers of macromolecular compounds of groups C09D183/00 - C09D183/16
- C09D4/06—Organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond in combination with a macromolecular compound other than an unsaturated polymer of groups C09D159/00 - C09D187/00
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C23—COATING METALLIC MATERIAL; COATING MATERIAL WITH METALLIC MATERIAL; CHEMICAL SURFACE TREATMENT; DIFFUSION TREATMENT OF METALLIC MATERIAL; COATING BY VACUUM EVAPORATION, BY SPUTTERING, BY ION IMPLANTATION OR BY CHEMICAL VAPOUR DEPOSITION, IN GENERAL; INHIBITING CORROSION OF METALLIC MATERIAL OR INCRUSTATION IN GENERAL
- C23C—COATING METALLIC MATERIAL; COATING MATERIAL WITH METALLIC MATERIAL; SURFACE TREATMENT OF METALLIC MATERIAL BY DIFFUSION INTO THE SURFACE, BY CHEMICAL CONVERSION OR SUBSTITUTION; COATING BY VACUUM EVAPORATION, BY SPUTTERING, BY ION IMPLANTATION OR BY CHEMICAL VAPOUR DEPOSITION, IN GENERAL
- C23C14/00—Coating by vacuum evaporation, by sputtering or by ion implantation of the coating forming material
- C23C14/22—Coating by vacuum evaporation, by sputtering or by ion implantation of the coating forming material characterised by the process of coating
-
- 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
- A61L2420/00—Materials or methods for coatings medical devices
- A61L2420/02—Methods for coating medical devices
-
- 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
- A61L2420/00—Materials or methods for coatings medical devices
- A61L2420/06—Coatings containing a mixture of two or more compounds
-
- 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
- C08G2650/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G2650/28—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule characterised by the polymer type
- C08G2650/50—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule characterised by the polymer type containing nitrogen, e.g. polyetheramines or Jeffamines(r)
-
- C—CHEMISTRY; METALLURGY
- C23—COATING METALLIC MATERIAL; COATING MATERIAL WITH METALLIC MATERIAL; CHEMICAL SURFACE TREATMENT; DIFFUSION TREATMENT OF METALLIC MATERIAL; COATING BY VACUUM EVAPORATION, BY SPUTTERING, BY ION IMPLANTATION OR BY CHEMICAL VAPOUR DEPOSITION, IN GENERAL; INHIBITING CORROSION OF METALLIC MATERIAL OR INCRUSTATION IN GENERAL
- C23C—COATING METALLIC MATERIAL; COATING MATERIAL WITH METALLIC MATERIAL; SURFACE TREATMENT OF METALLIC MATERIAL BY DIFFUSION INTO THE SURFACE, BY CHEMICAL CONVERSION OR SUBSTITUTION; COATING BY VACUUM EVAPORATION, BY SPUTTERING, BY ION IMPLANTATION OR BY CHEMICAL VAPOUR DEPOSITION, IN GENERAL
- C23C14/00—Coating by vacuum evaporation, by sputtering or by ion implantation of the coating forming material
- C23C14/06—Coating by vacuum evaporation, by sputtering or by ion implantation of the coating forming material characterised by the coating material
-
- 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]
-
- 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
- Y10T428/24—Structurally defined web or sheet [e.g., overall dimension, etc.]
- Y10T428/24942—Structurally defined web or sheet [e.g., overall dimension, etc.] including components having same physical characteristic in differing degree
- Y10T428/2495—Thickness [relative or absolute]
- Y10T428/24967—Absolute thicknesses specified
- Y10T428/24975—No layer or component greater than 5 mils thick
-
- 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]
-
- 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]
- Y10T428/31551—Of polyamidoester [polyurethane, polyisocyanate, polycarbamate, etc.]
- Y10T428/31562—Next to polyamide [nylon, etc.]
-
- 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]
- Y10T428/31725—Of polyamide
-
- 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]
- Y10T428/31855—Of addition polymer from unsaturated monomers
- Y10T428/31935—Ester, halide or nitrile of addition polymer
Definitions
- the invention relates to a coating formulation for preparing a medical coating, a medical coating obtainable by curing said coating formulation, a hydrophilic coating, a lubricious coating obtainable by wetting said hydrophilic coating, a coating system, use of a multifunctional polymerizable compound in a medical coating, an article comprising at least one medical, hydrophilic or lubricious coating and a method of forming on a substrate a medical, hydrophilic or lubricious coating.
- a hydrophobic surface may be made hydrophilic by applying a hydrophilic coating to it.
- Anti-microbial properties may be provided by including active substances, for example metal ions and/or other anti-microbial agents in the coating.
- drug-eluting coatings and imaging coatings may be obtained by including drugs and imaging materials in the coating, respectively.
- multifunctional polymerizable compounds are frequently applied in the coating formulation, which are polymerized upon curing in the presence of an initiator.
- the use of a multifunctional polymerizable compound may offer a controllable network which will allow tuned release of active substances, for example metal ions, other anti-microbial agents and drugs.
- good results have been achieved by physically or covalently entrapping functional components, e.g. functional polymers, into a network of a multifunctional polymerizable compound that provides the necessary adherence to the surface. In that way the functional, e.g.
- IPNs interpenetrating networks
- the inventors have found that many coatings comprising a multifunctional polymerizable compound show inferior coating performance. Typically such coatings tend to degrade within a given time, particularly in a hydrated environment causing increase in extractables or leachables.
- Such extractables or leachables may comprise low molecular and/or polymeric compounds and/or particles which may be vital to the function of the coating.
- the extractables or leachables may have for example an antimicrobial, anti-thrombogenic, imaging, bioactive, and/or signalling function.
- Degradation of said coatings typically results in loss of properties such as ability to hydrate and maintain hydration, loss of lubricious properties, loss of patient comfort, loss of imaging properties, increased risk of infection due to the residue being left on the tissue surface, uncontrolled release and co-elution problems for biologically active components, and/or lack of mechanical robustness, as demonstrated by the fact that parts of the coating are easily removed from the coated article upon rubbing.
- the problem to be solved is therefore to provide a coating formulation which comprises a multifunctional polymerizable compound and an initiator, and which results in robust and consistent coatings.
- G is a residue of a polyfunctional compound having at least n functional groups, wherein each R 1 and each R 2 independently represent hydrogen or a group selected from substituted and unsubstituted hydrocarbons which optionally contain one or more heteroatoms, preferably hydrogen or a C1-C20 hydrocarbon, more preferably hydrogen or a C1-C20 alkyl; and wherein n is an integer having a value of at least 2, preferably 2-100, more preferably 2-8, in particular 2 or 3.
- the invention thus relates to a coating formulation for preparing a medical coating, which coating formulation comprises:
- G is a residue of a polyfunctional compound having at least n functional groups, wherein each R 1 and each R 2 independently represent hydrogen or a group selected from substituted and unsubstituted hydrocarbons which optionally contain one or more heteroatoms, preferably hydrogen or a C1-C20 hydrocarbon, more preferably hydrogen or a C1-C20 alkyl; and wherein n is an integer having a value of at least 2, preferably 2-100, more preferably 2-8, in particular 2 or 3; and (b) at least one initiator.
- the coating formulation according to the invention results in better coating performance compared to conventional coating formulations.
- the multifunctional polymerizable compound (a) may be used in more than 0 %, based on the total weight of the dry coating, for example more than 1 %, or more than 2%.
- the multifunctional polymerizable compound can be present in the coating formulation up to 100%, 90 %, 80 %, 70 %, 60 % or 50, based on the total weight of the dry coating.
- the skilled person can vary the amount of multifunctional polymerizable compound within the above ranges to obtain the desired properties for his application.
- multifunctional polymerizable compound (a) has a number average molecular weight (Mn) of 500 g/mol or more, preferably 750 g/mol or more, more preferably 1000 g/mol or more.
- Mn number average molecular weight
- Generally multifunctional polymerizable compound (a) has a number average molecular weight (Mn) of 100,000 g/mol or less, - A -
- Multifunctional polymerizable compounds with an Mn within the preferred ranges show a favorable cross-link density, i.e. open enough to give room to functional components and dense enough to provide sufficient mechanical robustness.
- the average number of reactive moieties per molecule according to formula (1 ) is preferably in the range of about 1.2 to about 64, more preferably in the range of about 1.2 to about 16, most preferably in the range of about 1.2 to about 8.
- multifunctional polymerizable compound (a) is soluble in a polar solvent.
- a polar solvent within the context of the invention this means that according to this embodiment at least 1 g, preferably at least 3 g, more preferably at least 5 g, in particular at least 10 g of multifunctional polymerizable compound (a) can be dissolved in 100 g of the polar solvent at 25 0 C.
- suitable polar solvents include water and C1-C6 alcohols, in particular methanol, ethanol, propanol, isopropanol, butanol, isobutanol and t-butanol.
- multifunctional polymerizable compound (a) comprises at least one moiety containing a heteroatom.
- a heteroatom is understood to be a non-carbon, non-hydrogen atom.
- suitable hereoatoms include oxygen atoms (O), nitrogen atoms (N), sulfur atoms (S) and phosphor atoms (P).
- G is a residue of a hydrophilic polyfunctional compound, preferably chosen from the group consisting of polyethers, polyesters, polyurethanes, polyepoxides, polyamides, poly(meth)acrylamides, poly(meth)acrylics, polyoxazolidones, polyvinyl alcohols, polyethylene imines, polypeptides and polysaccharides, such as cellulose or starch or any combination of the above, more preferably a polymer comprising at least one polyethylene glycol or polypropylene glycol block.
- a hydrophilic polyfuctional compound is particularly advantageous if the coating needs to have hydrophilic and/or lubricious properties.
- R 1 preferably represents hydrogen, CH 3 or CH 2 OH. Particularly suitable are multifunctional polymerizable compounds wherein R 1 and R 2 both represent hydrogen or wherein R 1 represents CH 3 and R 2 represents hydrogen.
- suitable multifunctional polymerizable compounds are polyether based (meth)acrylamides, for example polyethylene glycol diacrylamide and polyethylene glycol dimethacrylamide.
- the coating formulation according to the invention can be cured in the presence of initiator (b).
- the term "to cure” includes any way of treating the formulation such that it forms a firm or solid coating.
- curing is understood to refer to physical or chemical hardening or solidifying by any method, for example heating, cooling, drying, crystallization or curing as a result of a chemical reaction, such as radiation-curing or heat-curing.
- all or part of the components in the coating formulation may be cross-linked forming covalent linkages between all or part of the components, for example by using UV or electron beam radiation.
- all or part of the components may also be ionically bonded, bonded by dipole-dipole type interactions, via Van der Waals forces or hydrogen bonds.
- the coating formulation according to the invention can for example be cured using electromagnetic radiation, for example visible or UV light, electro-beam, plasma, gamma or IR radiation, in the presence of an initiator, for example a photo- initiator or thermal initiator, to form the medical coating.
- electromagnetic radiation for example visible or UV light, electro-beam, plasma, gamma or IR radiation
- an initiator for example a photo- initiator or thermal initiator
- photo-initiators that can be used in the medical coating are free-radical photo-initiators, which are generally divided into two classes according to the process by which the initiating radicals are formed. Compounds that undergo unimolecular bond cleavage upon irradiation are termed Norrish Type I or homolytic photo-initiators.
- a Norrish Type Il photo-initiator interacts with a second molecule, i.e.
- a synergist which may be a low molecular weight compound of a polymer, in the excited state to generate radicals in a bimolecular reaction.
- the two main reaction pathways for Norrish Type Il photo-initiators are hydrogen abstraction by the excited initiator or photo-induced electron transfer. The mechanisms are further explained in WO06/056482.
- Suitable Norrish Type I or free-radical photo-initiators are benzoin derivatives, methylolbenzoin and 4-benzoyl-1 ,3-dioxolane derivatives, benzilketals, ⁇ , ⁇ -dialkoxyacetophenones, ⁇ -hydroxy alkylphenones, ⁇ - aminoalkylphenones, acylphosphine oxides, bisacylphosphine oxides, acylphosphine sulphides, halogenated acetophenone derivatives, and the like.
- Norrish Type I photoinitiators are lrgacure 2959 (2-hydroxy-4'-(2- hydroxyethoxy)-2-methyl propiophenone), lrgacure 651 (benzildimethyl ketal or 2,2- dimethoxy-1 ,2-diphenylethanone, Ciba-Geigy), lrgacure 184 (1-hydroxy-cyclohexyl- phenyl ketone as the active component, Ciba-Geigy), Darocur 1173 (2-hydroxy-2- methyl-1-phenylpropan-1-one as the active component, Ciba-Geigy), lrgacure 907 (2- methyl-1-[4-(methylthio)phenyl]-2-morpholino propan-1-one, Ciba-Geigy), lrgacure 369 (2-benzyl-2-dimethylamino-1-(4-morpholinophenyl)-
- Norrish Type Il photo-initiators that can be used in the medical coating formulation according to the invention include aromatic ketones such as benzophenone, xanthone, derivatives of benzophenone (e.g. chlorobenzophenone), blends of benzophenone and benzophenone derivatives (e.g. Photocure 81 , a 50/50 blend of 4-methyl-benzophenone and benzophenone), Michler's Ketone, Ethyl Michler's Ketone, thioxanthone and other xanthone derivatives like Quantacure ITX (isopropyl thioxanthone), benzil, anthraquinones (e.g. 2-ethyl anthraquinone), coumarin, or chemical derivatives or combinations of these photoinitiators.
- aromatic ketones such as benzophenone, xanthone, derivatives of benzophenone (e.g. chlorobenzophenone), blends of benzophenone and benzo
- Polymeric photo-initiators may also be used.
- the coating formulation further comprises a functional species (c), which is capable of providing a function to a coating.
- a functional species include functional polymers, e.g. hydrophilic polymers, imaging materials, drugs, and anti-thrombogenic materials.
- the functional species is a functional polymer it may be synthetic or bio-derived and can be a blend or a copolymer.
- polymer is used for a molecule comprising two or more repeating units. In particular it may be composed of two or more monomers which may be the same or different. As used herein, the term includes oligomers and prepolymers.
- polymers have a number average weight (Mn) of about 500 g/mol or more, in particular of about 1000 g/mol or more, although the Mn may be lower in case the polymer is composed of relatively small monomeric units.
- Mn number average weight
- the Mn is defined as the Mn as determined by light scattering.
- the functional species (c) is a hydrophilic polymer, which is capable of providing hydrophilicity to a coating and may be synthetic or bio-derived and can be a blend or a copolymer.
- a hydrophilic polymer in principle any polymer may be used that is suitable to provide a hydrophilic coating.
- suitable is such a polymer that is polymerisable, graftable and/or cross-linkable in the presence of an initiator.
- hydrophilic polymer is particularly useful in case a coating is required that is hydrophilic and, upon wetting with a wetting fluid, lubricious.
- a coating preferably acts as a lubricant to facilitate insertion of the device into and removal from the body and/or to facilitate drainage of fluids from the body.
- Lubricious properties are also required so as to minimize soft tissue damage upon insertion or removal.
- such medical devices may have a hydrophilic surface coating or layer which becomes lubricious and attains low-friction properties upon wetting, i.e. applying a wetting fluid for a certain time period prior to insertion of the device into the body of a patient.
- lubricious is defined as having a slippery surface.
- a coating on the outer or inner surface of a medical device, such as a catheter, is considered lubricious if (when wetted) it can be inserted into the intended body part without leading to injuries and/or causing unacceptable levels of discomfort to the subject.
- a coating is considered lubricious if it has a friction as measured on a Harland FTS5000 Friction Tester (HFT) of 20 g or less, preferably of 15 g or less, at a clamp-force of 300 g, a pull speed of 1 cm/s, and a temperature of 22 C C.
- HFT Harland FTS5000 Friction Tester
- a wetted coating contains at least 10 wt% of water, based on the dry weight of the coating, preferably at least 50 wt%, based on the dry weight of the coating, more preferably at least 100 wt% based on the dry weight of the coating.
- a water uptake of about 300- 500 wt% water is feasible.
- wetting fluids are treated or untreated water, water-containing mixtures with for example organic solvents or aqueous solutions comprising for example salts, proteins or polysaccharides.
- a wetting fluid can be a body fluid.
- the functional, in particular hydrophilic polymer has a number average molecular weight (Mn) in the range of about 8,000 to about 5,000,000 g/mol, and preferably is a polymer with a Mn in the range of about 20,000 to about 3,000,000 g/mol and more preferably in the range of about 200,000 to about 2,000,000 g/mol.
- Mn is the value as determined by light scattering.
- the functional polymer may for instance be a prepolymer, i.e. a polymer comprising one or more polymerisable groups, in particular one or more radically polymerisable groups such as one or more vinyl groups.
- a functional polymer which is free of such polymerisable groups may be cured in the presence of an initiator, in particular by the formation of grafts when the formulation is exposed to light.
- the functional, in particular hydrophilic, polymer may be non-ionic or ionic or a mixture of non-ionic and ionic polymers.
- Non-ionic polymers include but are not limited to poly(lactams), for example polyvinylpyrollidone (PVP), polyurethanes, homo- and copolymers of acrylic and methacrylic acid, polyvinyl alcohol, polyvinylethers, maleic anhydride based copolymers, polyesters, vinylamines, polyethylene imines, polyethylene oxides, poly(carboxylic acids), polyamides, polyanhydrides, polyphosphazenes, cellulosics, for example methyl cellulose, carboxymethyl cellulose, hydroxymethyl cellulose, and hydroxypropyl cellulose, heparin, dextran, polypeptides, for example collagens, fibrins, and elastin, polysacharrides, for example chitosan, hyaluronic acid, alginates, gelatin, and chitin, polyesters, for example polylactides, polyglycolides, and polycaprolactones, polypeptides, for example collagen,
- a polymer having a molecular weight corresponding to at least K15, more in particular K30, even more in particular K80 is preferred.
- Particular good results have been achieved with a polymer having a molecular weight corresponding to at least K90.
- a K120 or less, in particular a K100 is preferred.
- the K-value is the value as determinable by the Method W1307, Revision 5/2001 of the Viscotek Y501 automated relative viscometer. This manual may be found at www.ispcorp.com/products/hairscin/index 3.html.
- an ionic polymer may be a polyelectrolyte chosen from the group as defined below for component (d).
- a functional, in particular hydrophilic polymer (c) is present, it may be used in more than 0 wt% of the coating formulation, for example more than 1 wt%, more than 2 wt%, or more than 10 weight %, based on the total weight of the dry coating.
- the functional polymer can be present in the coating formulation up to 99 wt%, however, more often the functional polymer will be used up to 50, 60, 70, 80 or 90 wt%, based on the total weight of the dry coating.
- the coating formulation according to the invention may comprise an ionic compound (d), such as a low molecular weight salt or a polyelectrolyte, preferably a polyelectrolyte, in order to further improve the dry- out time of a hydrophilic coating.
- ionic may also refer to "ionizable”, as long as at least part of the ionizable groups is in the ionized form in the hydrophilic coating.
- such groups are named after their ionized form.
- polyelectrolytes are defined as a high molecular weight linear, branched or cross-linked polymers composed of macromolecules comprising constitutional units, in which between 5 and 100 % of the constitutional units are in the ionized form in the hydrophilic coating.
- a constitutional unit is understood to be for example a repeating unit, for example a monomer.
- a polyelectrolyte herein may refer to one type of polyelectrolyte composed of one type of macromolecules, but it may also refer to two or more different types of polyelectrolytes composed of different types of macromolecules.
- Polyelectrolytes can for example be used to improve the dry-out time of a lubricious coating.
- a suitable polyelectrolyte are its solubility and viscosity in aqueous media, its molecular weight, its charge density, its affinity with the supporting network of the coating and its biocompatibility.
- biocompatibility means biological compatibility by not producing a toxic, injurous or immunological response in living mammalian tissue.
- the polyelectrolytes have a number average molecular weight (Mn) of between 1 ,000 to 1 ,000,000 g/mol.
- ionic groups that may be present in the polyelectrolyte are ammonium groups, phosphonium groups, sulfonium groups, carboxylate groups, sulfate groups, sulfinic groups, sulfonic groups, phosphate groups, and phosphonic groups. Such groups are very effective in binding water.
- the polyelectrolyte also comprises metal ions. Metal ions, when dissolved in water, are complexed with water molecules to form aqua ions [M(H 2 O)J 0+ , wherein x is the coordination number and n the charge of the metal ion, and are therefore particularly effective in binding water.
- Metal ions that may be present in the polyelectrolyte are for example alkali metal ions, such as Na + or K + .
- alkali metal ions such as Na + or K + .
- anions such as halogenides, for example Cl “ , Br “ , I ' and F " , and also sulphates, nitrates, carbonates and phosphates may be present.
- Suitable polyelectrolytes are for example salts of homo- and copolymers of acrylic acid, methacrylic acid, maleic acid, fumaric acid, and sulfonic acid, and quaternary ammonium salts and mixtures and/or derivatives thereof.
- polyelectrolytes are polyacrylamide-co-acrylic acid sodium salt, polyacrylic acid sodium salt, polymethacrylic acid sodium salt, polyacrylamido-2-methyl-1- propanesulfonic acid sodium salt, poly(4-styrene sulfonic acid) sodium salt, poly(acrylamide-co-dialkyl ammonium chloride), quatemized poly[bis-(2- chloroethyl)ether-alt-1,3-bis[3-(dimethylamino)propyl]urea], polyallylammonium phosphate, poly(diallyldimethylammonium chloride), poly(sodium trimethyleneoxyethylene sulfonate), poly(dimethyldodecyl(2-acrylamidoethyl) ammonium bromide), poly(2-N methylpyridiniumethylene iodine), polyvinylsulfonic acids, and salts of poly(vinyl)pyridines, polyethyleneimines, and polylysines, and
- the ionic compound may also be a low molecular weight salt.
- any salt can be used as long as it does not negatively affect the performance of the coating composition or the coating.
- the coating formulation according to the invention may comprise 0- 90 wt%, 1-80 wt%, 5-50 wt%, or 10-30 wt% of an ionic compound based on the total weight of the dry coating.
- the coating formulation comprises both a functional polymer (c), being a hydrophilic polymer, and an ionic compound (d).
- the weight to weight ratio of the ionic compound (d) to the hydrophilic polymer (c) is preferably in the range of 1 :9 to 9:1 , more preferably 1 :30 to 1 :1 , even more preferably 1 :10 to 1 :5.
- coatings comprising an ionic compound, in particular a polyelectrolyte, are particularly vulnerable to inferior coating performance. Therefore it is surprising that the coating according to the invention show better properties even in the presence of an ionic compound (d).
- the invention relates to a coating formulation for preparing a hydrophilic coating.
- coating formulation refers to a liquid coating formulation, e.g. a solution or a dispersion comprising a liquid medium.
- a liquid coating formulation e.g. a solution or a dispersion comprising a liquid medium.
- the coating formulation thus further comprises a liquid medium in a sufficient amount to disperse or dissolve the other components of the formulation.
- the concentration of the liquid medium is usually at least 25 wt. %, preferably at least 40 wt. %, more preferably at least 68 wt.%, 75 wt. %, 80 wt. %, or 85 wt. % of the total weight of the liquid coating formulation.
- the amount of liquid medium in the composition is preferably relatively high. For that reason the total solids content is preferably 20 wt% or less.
- the liquid medium may be a single liquid medium or a mixture. It is chosen such that the components can be dissolved or at least dispersed therein. In particular for dissolving or dispersing the functional polymer, if present, it is preferred that the liquid medium comprises a polar solvent.
- a liquid is considered polar if it is soluble in water.
- it comprises water and/or an organic solvent soluble in water, for example an alcohol, acetone, methylethyl ketone, tetrahydrofuran, dichloromethane, and aqueous mixtures or emulsions thereof, preferably an alcohol, more preferably a C1-C4 alcohol, in particular methanol and/or ethanol.
- the ratio water to organic solvent, in particular one or more alcohols may be in the range of about 25:75 to 75:25, in particular 40:60 to 60:40, more in particular 45:55 to 55:45.
- the invention also relates to a medical coating obtainable by applying coating formulation according to the invention to a substrate and curing it.
- the invention further relates to a hydrophilic coating and to a lubricious coating obtainable by wetting said hydrophilic coating applying a wetting fluid, and to the use of a multifunctional polymerizable compound according to formula (1 ) in a medical coating.
- the invention relates to a medical, hydrophilic or lubricious coating comprising a polymer network comprising multifunctional polymerizable compound (a).
- multifunctional polymerizable compound (a) is present in its polymerized form, i.e. at least part of the vinyl groups have reacted.
- multifunctional polymerizable compound (a) also refers to the reacted (i.e. polymerized) multifunctional polymerizable compound.
- the invention relates to an article, in particular a medical device or a medical device component comprising at least one medical, hydrophilic or lubricious coating according to the invention and to a method of forming on a substrate the medical, hydrophilic or lubricious coating according to the invention, wherein the coating formulation according to the invention is applied to at least one surface of the substrate, wherein the coating formulation is allowed to cure by exposing the formulation the electromagnetic radiation or heat thereby activating the initiator, and wherein, in case of a lubricious coating, the coating is subsequently wetted in a wetting fluid.
- the medical coating comprises a multifunctional polymerizable compound (a) and at least one functional polymer (c).
- the weight ratio of functional polymer (c) to multifunctional polymerizable compound (a) may for example vary between 5:95 and 95:5.
- the multifunctional polymerizable compound and the polyelectrolyte(s) are covalently linked and/or physically bound to each other to form a polymer network after curing.
- the functional coating comprises a multifunctional polymerizable compound (a), a functional (e.g. non-ionic hydrophilic) polymer (c) and a polyelectrolyte (d).
- the weight ratio of the sum of polyelectrolyte and non- ionic hydrophilic polymer to multifunctional polymerizable compound may for example vary between 5:95 and 95:5.
- the multifunctional polymerizable compound, the non-ionic hydrophilic polymer, and the polyelectrolyte are covalently linked and/or physically bound to each other to form a polymer network after curing.
- the invention also relates to a coating system for preparing a lubricious coating, said coating system comprising a coating formulation according to the invention and a wetting fluid comprising an ionic compound, preferably a polyelectrolyte or a low molecular weight salt.
- the invention also relates to a medical, hydrophilic or lubricious coating comprising a multifunctional polymerizable compound comprising a polymer network comprising multifunctional polymerizable compound (a).
- Said coating may further comprise a functional species (c), e.g. a functional polymer and an ionic species (d), which may originate from the coating formulation or from a wetting fluid.
- the coating formulation according to the invention further comprises at least one surfactant, which can improve the surface properties of the coating.
- Surfactants constitute the most important group of detergent components. Generally, these are water-soluble surface-active agents comprised of a hydrophobic portion, usually a long alkyl chain, attached to hydrophilic or water solubility enhancing functional groups. Surfactants can be categorized according to the charge present in the hydrophilic portion of the molecule (after dissociation in aqueous solution): ionic surfactants, for example anionic or cationic surfactants, and non-ionic surfactants.
- ionic surfactants include Sodium dodecylsulfate (SDS), Sodium cholate, Bis(2-ethylhexyl)sulfosuccinate Sodium salt, Cetyltrimethylammoniumbromide (CTAB), Lauryldimethylamine-oxide (LDAO), N- Laurylsarcosine Sodium salt and Sodium deoxycholate (DOC).
- CTAB Cetyltrimethylammoniumbromide
- LDAO Lauryldimethylamine-oxide
- DOC N- Laurylsarcosine Sodium salt
- non-ionic surfactants include Alkyl Polyglucosides such as TRITONTM BG-10 Surfactant and TRITON CG-110 Surfactant, Branched Secondary Alcohol Ethoxylates such as
- surfactant preferably 0.05- 0.5 wt%, based on the total weight of the dry coating.
- One or more other additives which may be present in the coating formulation according to the invention are for example amine compounds, for example diallylamine, diisopropylamine, diethylamine, and diethylhexylamine; antioxidants; water-soluble radical stabilizers; UV absorbers; light stabilizers; (silane) coupling agents; coating surface improvers; heat polymerization inhibitors; leveling agents; surfactants; colorants, for example a pigment or a dye; discolorants; preservatives; dispersing agents; plasticizers; lubricants; solvents; fillers; wettability improvers; urea; and chain transfer agents.
- the colorant can be a pigment or dye.
- the medical coating according to the invention can be coated on an article.
- the medical coating can be coated on a substrate which may be selected from a range of geometries and materials.
- the substrate may have a texture, such as porous, non-porous, smooth, rough, even or uneven.
- the substrate supports the medical coating on its surface.
- the medical coating can be on all areas of the substrate or on selected areas.
- the medical coating can be applied to a variety of physical forms, including films, sheets, rods, tubes, molded parts (regular or irregular shape), fibers, fabrics, and particulates.
- Suitable surfaces for use in the invention are surfaces that provide the desired properties such as porosity, hydrophobicity, hydrophilicity, colorisability, strength, flexibility, permeability, elongation abrasion resistance and tear resistance.
- suitable surfaces are for instance surfaces that consist of or comprise metals, plastics, ceramics, glass and/or composites.
- the medical coating may be applied directly to the said surfaces or may be applied to a pretreated or coated surface where the pretreatment or coating is designed to aid adhesion of the medical coating to the substrate.
- the medical coating according to the invention is coated on a biomedical substrate.
- a biomedical substrate refers, in part, to the fields of medicine, and the study of living cells and systems. These fields include diagnostic, therapeutic, and experimental human medicine, veterinary medicine, and agriculture. Examples of medical fields include ophthalmology, orthopedics, and prosthetics, immunology, dermatology, pharmacology, and surgery; nonlimiting examples of research fields include cell biology, microbiology, and chemistry.
- biomedical also relates to chemicals and compositions of chemicals, regardless of their source, that (i) mediate a biological response in vivo, (ii) are active in an in vitro assay or other model, e.g., an immunological or pharmacological assay, or (iii) can be found within a cell or organism.
- biomedical also refers to the separation sciences, such as those involving processes of chromatography, osmosis, reverse osmosis, and filtration. Examples of biomedical articles include research tools, industrial, and consumer applications. Biomedical articles include separation articles, implantable articles, and ophthalmic articles.
- Ophthalmic articles include soft and hard contact lenses, intraocular lenses, and forceps, retractors, or other surgical tools that contact the eye or surrounding tissue.
- a preferred biomedical article is a soft contact lens made of a silicon-containing hydrogel polymer that is highly permeable to oxygen.
- Separation articles include filters, osmosis and reverse osmosis membranes, and dialysis membranes, as well as bio-surfaces such as artificial skins or other membranes.
- Implantable articles include catheters, and segments of artificial bone, joints, or cartilage.
- An article may be in more than one category, for example, an artificial skin is a porous, biomedical article.
- Examples of cell culture articles are glass beakers, plastic petri dishes, and other implements used in tissue cell culture or cell culture processes.
- a preferred example of a cell culture article is a bioreactor micro-carrier, a silicone polymer matrix used in immobilized cell bioreactors, where the geometry, porosity, and density of the particulate micro-carrier may be controlled to optimize performance.
- the micro-carrier is resistant to chemical or biological degradation, to high impact stress, to mechanical stress (stirring), and to repeated steam or chemical sterilization.
- silicone polymers other materials may also be suitable.
- This invention may also be applied in the food industry, the paper printing industry, hospital supplies, diapers and other liners, and other areas where hydrophilic, wettable, or wicking articles are desired.
- the medical device can be an implantable device or an extracorporeal device.
- the devices can be of short-term temporary use or of long-term permanent implantation.
- suitable devices are those that are typically used to provide for medical therapy and/or diagnostics in heart rhythm disorders, heart failure, valve disease, vascular disease, diabetes, neurological diseases and disorders, orthopedics, neurosurgery, oncology, ophthalmology, and ENT surgery.
- Suitable examples of medical devices include, but are not limited to, a stent, stent graft, anastomotic connector, synthetic patch, lead, electrode, needle, guide wire, catheter, sensor, surgical instrument, angioplasty balloon, wound drain, shunt, tubing, infusion sleeve, urethral insert, pellet, implant, blood oxygenator, pump, vascular graft, vascular access port, heart valve, annuloplasty ring, suture, surgical clip, surgical staple, pacemaker, implantable defibrillator, neurostimulator, orthopedic device, cerebrospinal fluid shunt, implantable drug pump, spinal cage, artificial disc, replacement device for nucleus pulposus, ear tube, intraocular lens and any tubing used in minimally invasive surgery.
- Articles that are particularly suited to be used in the present invention include medical devices or components such as catheters, guidewires, stents, syringes, metal and plastic implants, contact lenses, medical tubing, and extracorporeal devices.
- the coating formulation can be applied to the substrate by for example dip-coating. Other methods of application include spray, wash, vapor deposition, brush, roller, curtain, spin coating and other methods known in the art.
- the thickness of the medical coating according to the invention may be controlled by altering soaking time, drawing speed, viscosity of the coating formulation and the number of coating steps.
- the thickness of a medical coating on a substrate ranges from 0.05-300 ⁇ m, preferably 0.1-200 ⁇ m.
- a primer coating may be used in order to provide a binding between the medical coating and the substrate.
- the primer coating is often referred to as the primary coating, base coat or tie coat.
- Said primer coating is a coating that facilitates adhesion of the medical coating to a given substrate, as is described in for example WO02/10059.
- the binding between the primer coating and the medical coating may occur due to covalent or ionic links, hydrogen bonding, physisorption or polymer entanglements.
- These primer coatings may be solvent based, water based (latexes or emulsions) or solvent free and may comprise linear, branched and/or cross-linked components.
- Typical primer coatings that could be used comprise for example polyether sulfones, polyurethanes, polyesters, including polyacrylates, as described in for example US6,287,285, polyamides, polyethers, polyolefins and copolymers of the mentioned polymers.
- the primer coating comprises a supporting polymer network, the supporting network optionally comprising a functional, for example hydrophilic, polymer entangled in the supporting polymer network as described in WO2006/056482 A1.
- a functional, for example hydrophilic, polymer entangled in the supporting polymer network as described in WO2006/056482 A1.
- the information with respect to the formulation of the primer coating is herewith incorporated by reference.
- a primer layer as described in WO2006/056482 A1 is in particular useful for improving adherence of a coating comprising a hydrophilic polymer such as a polylactam, in particular PVP and/or another of the above identified hydrophilic polymers, on a surface having about the same or a lower hydrophilicity.
- a hydrophilic polymer such as a polylactam, in particular PVP and/or another of the above identified hydrophilic polymers
- One embodiment of the invention relates to an article - in particular a medical device, more in particular a catheter - comprising a coating, which coating comprises at least two layers: an inner and an outer layer, of which the inner layer (i.e. a layer between the outer layer and the surface) is a primer layer, comprising a supporting polymer network which is composed of a supporting polymer selected from the group consisting of polyethers, polyesters, polyurethanes, polyepoxides, polyamides, poly(meth)acrylamides, poly(meth)acrylics, polyoxazolidones, polyvinyl alcohols, polyethylene imines, polypeptides and polysaccharides, such as cellulose or starch or any combination of the above, more preferably a polymer comprising at least one polyethylene glycol or polypropylene glycol block, including copolymers comprising a polyether and/or polythioether moiety, and the outer layer is a functional layer comprising a multifunctional polymerizable compound (a
- the surface of the article is subjected to oxidative, photo-oxidative and/or polarizing surface treatment, for example plasma and/or corona treatment in order to improve the adherence of the coating which is to be provided.
- oxidative, photo-oxidative and/or polarizing surface treatment for example plasma and/or corona treatment in order to improve the adherence of the coating which is to be provided.
- Suitable conditions are known in the art.
- Curing conditions can be determined, based on known curing conditions for the photo-initiator and polymer or routinely be determined. In general, curing may be carried out at any suitable temperature depending on the substrate, as long as the mechanical properties or another property of the article are not adversely affected to an unacceptable extent.
- Intensity and wavelength of the electromagnetic radiation can routinely be chosen based on the photo-initiator of choice.
- a suitable wavelength in the UV, visible or IR part of the spectrum may be used.
- PEG 150 g, 75 mmol OH, Biochemika Ultra from Fluka [95904], #427345/1 , OH-value: 28.02 mg KOH/g, 499.5 meq/kg, Mn: 4004 mol/g
- lrgacure 1035 0.2 g ⁇ 0.15 w%, Ciba Specialy Chemical
- the PEG/toluene solution was distilled azeotropically overnight (50 0 C / 70 mbar) leading the condensing toluene over 4A mol sieves. It is important to determine accurately the hydroxyl value for each batch of PEG by OH titration (see analysis) to calculate the amount of acryloyl chloride (Merck, for synthesis, stored at 5°C and used as received) to be added and to determine the conversion during the reaction.
- Triethylamine (9.10 grams, 90 mmol, Aldrich, 99.5%, kept under nitrogen atmosphere and is used as received) was added to the reaction mixture, followed by the drop wise addition over 1 h of acryloyl chloride (8.15 grams, 90 mmol, (Merck, for synthesis, is stored at 5°C and used as received) dissolved in 50 ml_ of dry toluene.
- the Acryloyl chloride and triethyl amine used should be colorless liquids.
- the reaction mixture was stirred for 2 to 4 hours at 45°C under nitrogen atmosphere. During the reaction the temperature was kept at 45°C to prevent crystallization of PEG.
- TFAA trifluoro acetic anhydride
- the NMR pattern confirmed the formation of PEG 4000 DA.
- the IR pattern confirmed the formation of PEG 4000 DA.
- the synthesis and characterization of PEG 2000 DA was similar to synthesis and characterization of PEG 4000 DA. Instead of PEG 4000 (M r 3500-4500; Biochemika Ultra from Fluka), PEG 2000 (M r 1900-2200; Biochemika Ultra from Fluka) was used.
- the solution was cooled in an ice bath to precipitate NEt 3 -HCI salts and was then filtrated. After adding 1% (w/w) Irganox 1035, the filtrate was concentrated under vacuum. The concentrate was redissolved in 75 mL of dichloromethane, followed by precipitation in 1.5 L ice cold diethyl ether. The product was collected by filtration and subsequent washing with diethyl ether.
- the NMR spectrum confirmed the formation of PEG(AM) 2 . From the integration of the NMR peaks at 6.2 and 6.1 ppm, respectively 1.8 ppm, about 99% of the PEG-diamine was estimated to be converted into PEG(AM) 2 .
- methacryloyl chloride (Acros) was used instead of acryloyl chloride.
- the NMR pattern confirmed the formation of PEG(MAM) 2 . From the integration of the NMR peaks at 5.7 and 5.3 ppm, respectively 1.8 ppm, about 90% of the PEG-diamine was estimated to be converted into PEG(MAM) 2 . The IR pattern confirmed the formation of PEG(MAM) 2 .
- toluene diisocyanate (TDI or T, Aldrich, 95 % purity, 87.1 g, 0.5 mol), Irganox 1035 (Ciba Specialty Chemicals, 0.58 g, 1 wt% relative to hydroxy ethyl acrylate (HEA or H)) and tin(ll) 2-ethyl hexanoate (Sigma, 95 % purity, 0.2 g, 0.5 mol) were placed in a 1 liter flask and stirred for 30 minutes. The reaction mixture was cooled to 0 0 C using an ice bath.
- HEA Aldrich, 96 % purity, 58.1 g, 0.5 mol
- PTGL Poly(2-methyl-1 ,4-butanediol)-alt-poly(tetramethyleneglycol)
- reaction mixture was heated to 60 °C and stirred for 18 h, upon which the reaction was complete as indicated by GPC (showing complete consumption of HEA), IR (displayed no NCO related bands) and NCO titration (NCO content below 0.02 wt%).
- Coating formulation Example 2 and Comparative Experiment B Table 5.
- Coating formulation Examples 3 and 4 and Comparative Experiment C For the primer formulations as well as for the coating formulations the compounds were dissolved in the solvent under stirring at room temperature. To obtain the coating formulation, a formulation containing all of the compounds indicated above except the multifunctional polymerizable compound was prepared the day before the start of the experiment. The experiment was started with the dissolution of the multifunctional polymerizable compound in this formulation (within one hour the multifunctional polymerizable compound was dissolved).
- NMR Nuclear magnetic resonance
- FTIR Fourier transformed infrared
- the primer coating formulation according to Table 1 was coated on 120 ⁇ m PET foil using Meyenbar # 12 resulting in a dry film thickness of approximately 550 nm.
- the primer coating formulation was cured with 1.10 J/cm 2 using a D-lamp in air.
- the coating formulations of Table 3 were coated on the primer.
- the coatings were left for 1 min to dry at 25 0 C and were exposed to a single UV pass with 1.10 J/cm 2 using a D-lamp in air.
- the resulting coating thickness was 2 ⁇ m.
- Harland PCX coater Dip-coating was performed with a Harland PCX coater.
- the intensity of the lamps was measured by means of a Harland UVR 335 (also known as IL 1400) equipped with an International Light detector SED 005#989.
- Input optic W#11521 , filter wbs320#27794.
- the tubing was dipped in the primer formulation for 10 seconds, moved up with a speed of 0.3 cm/s and cured for 15 seconds with a total dose of 0.9 J/cm 2 .
- the tubing was then dipped in the topcoat formulation for 10 seconds, moved up with a speed of 1.5 cm/s and cured for 360 seconds with a total dose of 21.6 J/cm 2 . After drying for a night at room temperature, the lubricity, wear resistance and dry-out time of the coatings were determined.
- a guide wire was inserted in the tubing to fix the tubing and to attach it in the holder of the friction tester. If the test was to be run wet, the clamp was positioned over the container such that the clamp pads were submerged. The holder was moved down such that the (coated) tubing was also immersed in the water. After immersing for one minute the clamp was closed and fixed the tubing with a clamp force of 300 g. The holder moved up for 10 cm and the friction force was measured during the moving-up. The following parameters were applied: 25 testing cycles, pulling speed 1.0 cm/s, acceleration time 2.0 s. When compounds were leaching out of the coating, the clamp pads of the friction tester were cleaned before each testing cycle.
- the dry-out time can be determined by measuring the lubricity (as friction in g) as a function of time. In the test to measure the dry-out time 5 testing cycles were applied with a time interval of 300 s. All other parameters are the same as in the lubricity test. 3.6. Stability tests (Example 1 and Comparative Experiment A): effect of multifunctional polvmerizable compound on rub resistance
- Example 1 In order to test the stability of the coating formulations of Example 1 and Comparative Example A the following test was performed.
- the films prepared according to 3.3. were incubated in standard phosphate buffer solutions ("PBS buffers") for 110 hours at 45 0 C.
- PBS buffers standard phosphate buffer solutions
- the rub resistance was immediately checked after annealing using a single index finger tip using 5 drops of water. The results are shown in Table 6.
- the tubings coated with the coating formulation comprising PEGDA were tested twice in a series (catheter still immersed in water). After the 25 cycles of the first test the coated tubing was kept in the water for 10 minutes before starting the second test consisting of 25 cycles. The results are given in Figure 1.
- Table 6 shows that the coating according to Example 1 , prepared form a coating formulation containing PEG(AM) 2 , lrgacure 2959 and ethanol is much more stable against rubbing than an equivalent coating containing PEGDA instead of PEG(AM) 2
- Example 2 Stability of PEG(AM) 2 expressed in wt% of PEG(AM) 2 in formulation.
- Figure 1 shows that the lubricity, expressed as the friction force (the higher the friction force, the lower the lubricity), is significantly reduced after incubating the coating formulations comprising PEGDA used for preparing the lubricious coatings for 2 days at 50 0 C (closed triangles): friction forces in the range 40-80 g were measured.
- the coatings prepared from a PEGDA containing coating formulation parts of the coating were removed by the clamp pads of the friction tester during the first cycles of the first test series. As a result, the coatings were damaged.
- the second test of the test series after 2 days of incubation therefore resulted in even higher friction forces (open triangles) in the range 70-140 g. This was not observed for the coatings prepared from the fresh coating formulation (0 days incubation) (closed and open squares): friction forces of approximately 10 g were measured in both test series.
- Figure 2 shows much more favorable results for the lubricious coatings prepared from the formulation containing PEG(AM) 2 . Even the coatings prepared from coating compositions incubated at 2 or 7 days still feature a high lubricity (low friction force): in all measurements the friction force was below 10 g. All coatings stayed intact during the friction test. The incubation of the formulation had no influence on the wear resistance of the resulting coating.
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Organic Chemistry (AREA)
- Veterinary Medicine (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Epidemiology (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Wood Science & Technology (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Surgery (AREA)
- Vascular Medicine (AREA)
- Heart & Thoracic Surgery (AREA)
- General Chemical & Material Sciences (AREA)
- Inorganic Chemistry (AREA)
- Metallurgy (AREA)
- Mechanical Engineering (AREA)
- Materials For Medical Uses (AREA)
- Paints Or Removers (AREA)
- Medicinal Preparation (AREA)
- Polyethers (AREA)
- Macromonomer-Based Addition Polymer (AREA)
Abstract
Description
Claims
Priority Applications (4)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2009527743A JP5499321B2 (en) | 2006-09-13 | 2007-09-13 | Coating formulations for medical coatings |
EP07818144.3A EP2059272B1 (en) | 2006-09-13 | 2007-09-13 | Coating formulation for medical coating |
US12/440,775 US20100076546A1 (en) | 2006-09-13 | 2007-09-13 | Coating formulation for medical coating |
US15/009,747 US20160310643A1 (en) | 2006-09-13 | 2016-01-28 | Coating formulation for medical coating |
Applications Claiming Priority (6)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP06019148 | 2006-09-13 | ||
EP06019148.3 | 2006-09-13 | ||
EP07009703.5 | 2007-05-15 | ||
EP07009702 | 2007-05-15 | ||
EP07009703 | 2007-05-15 | ||
EP07009702.7 | 2007-05-15 |
Related Child Applications (2)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US12/440,775 A-371-Of-International US20100076546A1 (en) | 2006-09-13 | 2007-09-13 | Coating formulation for medical coating |
US15/009,747 Division US20160310643A1 (en) | 2006-09-13 | 2016-01-28 | Coating formulation for medical coating |
Publications (1)
Publication Number | Publication Date |
---|---|
WO2008031596A1 true WO2008031596A1 (en) | 2008-03-20 |
Family
ID=38739926
Family Applications (2)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/EP2007/007985 WO2008031596A1 (en) | 2006-09-13 | 2007-09-13 | Coating formulation for medical coating |
PCT/EP2007/007984 WO2008031595A2 (en) | 2006-09-13 | 2007-09-13 | Coated medical device |
Family Applications After (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/EP2007/007984 WO2008031595A2 (en) | 2006-09-13 | 2007-09-13 | Coated medical device |
Country Status (4)
Country | Link |
---|---|
US (4) | US8828546B2 (en) |
EP (2) | EP2059272B1 (en) |
JP (2) | JP5499321B2 (en) |
WO (2) | WO2008031596A1 (en) |
Cited By (24)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2009112548A1 (en) * | 2008-03-12 | 2009-09-17 | Dsm Ip Assets B.V. | Hydrophilic coating |
EP2183105A2 (en) * | 2007-08-27 | 2010-05-12 | 3M Innovative Properties Company | Polymer gel structure and method for producing same |
JP2012502690A (en) * | 2008-09-15 | 2012-02-02 | シーヴィー インジェニュイティ コーポレイション | Local delivery of water-soluble or water-insoluble therapeutic agents to the body lumen surface |
JP2013520277A (en) * | 2010-02-24 | 2013-06-06 | シーヴィー インジェニュイティ コーポレイション | Local delivery of water-soluble or water-insoluble therapeutic agents to the body lumen surface |
WO2013110566A1 (en) | 2012-01-27 | 2013-08-01 | Basf Se | Radiation-curable anti-microbial coating compound |
WO2013110504A1 (en) | 2012-01-27 | 2013-08-01 | Basf Se | Radiation-curable antimicrobial coatings |
US8513320B2 (en) | 2007-02-28 | 2013-08-20 | Dsm Ip Assets B.V. | Hydrophilic coating |
US8512795B2 (en) | 2005-12-09 | 2013-08-20 | Dsm Ip Assets B.V. | Hydrophilic coating comprising a polyelectrolyte |
US8728455B2 (en) | 2012-01-27 | 2014-05-20 | Basf Se | Radiation-curable antimicrobial coatings |
AU2010226929B2 (en) * | 2009-10-16 | 2014-07-24 | Confluent Surgical, Inc. | Prevention of premature gelling of delivery devices for pH dependent forming materials |
US8809411B2 (en) | 2007-02-28 | 2014-08-19 | Dsm Ip Assets B.V. | Hydrophilic coating |
US8828546B2 (en) | 2006-09-13 | 2014-09-09 | Dsm Ip Assets B.V. | Coated medical device |
US8957125B2 (en) | 2010-06-16 | 2015-02-17 | Dsm Ip Assets B.V. | Coating formulation for preparing a hydrophilic coating |
US9034362B2 (en) | 2008-09-15 | 2015-05-19 | The Spectranetics Corporation | Local delivery of water-soluble or water-insoluble therapeutic agents to the surface of body lumens |
US9132211B2 (en) | 2008-09-15 | 2015-09-15 | The Spectranetics Corporation | Local delivery of water-soluble or water-insoluble therapeutic agents to the surface of body lumens |
US9238715B2 (en) | 2010-05-27 | 2016-01-19 | Nanyang Technological University | Polymerizable composition for ophthalmic and medical use and antimicrobial composition obtained by polymerizing the polymerizable composition |
WO2016200337A1 (en) | 2015-06-08 | 2016-12-15 | Jmedtech Pte Ltd | Coating compositions comprising adhesion promoting base layer |
EP3037454A4 (en) * | 2013-08-20 | 2017-05-24 | Boe Technology Group Co. Ltd. | Polyether compound, preparation method and photoresist composition thereof |
US9737637B2 (en) | 2004-11-29 | 2017-08-22 | Dsm Ip Assets B.V. | Method for reducing the amount of migrateables of polymer coatings |
US9901663B2 (en) | 2013-05-06 | 2018-02-27 | Abbott Cardiovascular Systems Inc. | Hollow stent filled with a therapeutic agent formulation |
US9956385B2 (en) | 2012-06-28 | 2018-05-01 | The Spectranetics Corporation | Post-processing of a medical device to control morphology and mechanical properties |
US10525171B2 (en) | 2014-01-24 | 2020-01-07 | The Spectranetics Corporation | Coatings for medical devices |
US10978277B2 (en) | 2015-05-11 | 2021-04-13 | Nova Plasma Ltd. | Apparatus and method for handling an implant |
WO2021233743A1 (en) | 2020-05-18 | 2021-11-25 | Dsm Ip Assets B.V. | Coating composition, method of making a hydrophilic coating on a substrate, and medical device comprising such coating |
Families Citing this family (29)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US20120077049A1 (en) * | 2007-08-06 | 2012-03-29 | Abbott Cardiovascular Systems, Inc. | Medical devices having a lubricious coating with a hydrophilic compound in an interlocking network |
JP5451112B2 (en) * | 2009-03-04 | 2014-03-26 | テルモ株式会社 | Guide wire |
ES2474121T3 (en) | 2012-02-01 | 2014-07-08 | Bioenergy Capital Ag | Matrix for cell colonization |
PL2623133T3 (en) | 2012-02-01 | 2014-09-30 | Bioenergy Capital Ag | Implant matrix from a polymer mixture |
US9395468B2 (en) | 2012-08-27 | 2016-07-19 | Ocular Dynamics, Llc | Contact lens with a hydrophilic layer |
AU2013332203B2 (en) | 2012-10-19 | 2017-08-24 | Saltworks Technologies Inc. | Acrylamide-based crosslinking monomers, their preparation, and uses thereof |
JP6383732B2 (en) | 2013-01-04 | 2018-08-29 | サーモディクス,インコーポレイティド | Low particle lubricity coating with a layer containing vinylpyrrolidone polymer and acidic polymer |
WO2014109824A1 (en) * | 2013-01-08 | 2014-07-17 | Abbott Cardiovascular Systems Inc. | Medical device having a lubricious coating with hydrophilic compounds in an interlocking network |
US10647829B2 (en) | 2013-06-20 | 2020-05-12 | Sumitomo Rubber Industries, Ltd. | Surface modification method and surface modification body |
EP3988992A1 (en) | 2013-11-15 | 2022-04-27 | Tangible Science, Inc. | Contact lens with a hydrophilic layer |
AU2014363936B2 (en) * | 2013-12-12 | 2018-07-26 | Hollister Incorporated | Water disintegrable flushable catheter with a hydrophilic coating |
EP2896635B1 (en) | 2014-01-17 | 2018-05-23 | Fujifilm Corporation | Flexible tube, endoscopic medical apparatus, and resin composition for top coat layer |
JP6371165B2 (en) * | 2014-09-02 | 2018-08-08 | 住友ゴム工業株式会社 | Metal medical tools |
CN107206119B (en) | 2014-12-09 | 2021-01-29 | 实体科学公司 | Medical device coating with biocompatible layer |
JP2015077452A (en) * | 2014-12-25 | 2015-04-23 | ナンヤン テクノロジカル ユニヴァーシティー | Polymerizable composition for eye and medical treatment, and antimicrobial composition obtained by polymerizing the same |
CN107949403A (en) | 2015-04-16 | 2018-04-20 | 好利司泰公司 | Hydrophilic coating and forming method thereof |
JP6670325B2 (en) * | 2015-05-08 | 2020-03-18 | コーニンクレッカ フィリップス エヌ ヴェKoninklijke Philips N.V. | Hydrophilic coating for intra-conduit devices |
JP6613692B2 (en) | 2015-08-03 | 2019-12-04 | 住友ゴム工業株式会社 | Surface modification method and surface modified elastic body |
CN109195643A (en) | 2016-03-31 | 2019-01-11 | 舒尔默迪克斯公司 | Lubricant coating for medical device |
WO2018039582A1 (en) * | 2016-08-25 | 2018-03-01 | University Of Florida Research Foundation, Inc. | Lubricious structures, methods of making them, and methods of use |
WO2018112196A1 (en) | 2016-12-16 | 2018-06-21 | Surmodics, Inc. | Hydrophobic active agent particle coatings and methods for treatment |
JP6338715B2 (en) * | 2017-02-06 | 2018-06-06 | ナンヤン テクノロジカル ユニヴァーシティー | Ophthalmic and medical polymerizable compositions and antimicrobial compositions obtained by polymerizing the same |
CN113117154B (en) * | 2019-12-31 | 2022-10-21 | 东莞市先健医疗有限公司 | Hydrophilic coating solution, method for preparing the same, and medical device coated with the same |
KR102222519B1 (en) * | 2019-12-31 | 2021-03-04 | 주식회사 이노테라피 | Self-Sealing Injection Needle for Inhibiting Generation of Fistula of Eyeball and Method of Preparing the Same |
CN115297908B (en) | 2020-01-17 | 2024-04-19 | 韦恩视野有限责任公司 | Antibacterial silicone |
CN111603618B (en) * | 2020-06-03 | 2021-04-20 | 江门市泰乐医疗科技有限公司 | Guide wire coating composition, guide wire coating and preparation method of guide wire coating |
CN111840660B (en) * | 2020-07-30 | 2021-12-14 | 齐鲁工业大学 | Hydrophilic polypeptide monolayer film, preparation method and application |
WO2022241252A1 (en) * | 2021-05-13 | 2022-11-17 | Regents Of The University Of Minnesota | Descemet membrane endothelial keratoplasty (dmek) assemblies and injectors with friction-reducing coatings |
CN115537030A (en) * | 2022-09-27 | 2022-12-30 | 张大庆 | Preparation of hydrophilic chitosan compound solution and application of hydrophilic chitosan compound solution in liquid mulching film |
Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0405464A2 (en) * | 1989-06-28 | 1991-01-02 | Ajinomoto Co., Inc. | Polyether acrylamide derivatives and active energy ray curable resin composition |
WO1997014448A1 (en) * | 1995-10-17 | 1997-04-24 | Ajay Kumar Luthra | Biocompatible lubricious hydrophilic materials for medical devices |
WO2001092584A1 (en) * | 2000-06-02 | 2001-12-06 | Eidgenossische Technische Hochschule Zurich | Conjugate addition reactions for the controlled delivery of pharmaceutically active compounds |
WO2006056482A1 (en) * | 2004-11-29 | 2006-06-01 | Dsm Ip Assets B.V. | Method for reducing the amount of migrateables of polymer coatings |
Family Cites Families (86)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
AU494547B2 (en) | 1972-07-10 | 1977-10-20 | Johnson & Johnson | Hydrophilic random interpolymer compositions and method for making same |
DE2545290A1 (en) | 1975-10-09 | 1977-04-21 | Roehm Gmbh | METHOD OF POLYMERIZATION BY USING UV LIGHT |
CA1104782A (en) | 1976-06-07 | 1981-07-14 | Robert E. Erickson | Absorbent films and laminates |
US4272620A (en) | 1978-08-09 | 1981-06-09 | Agency Of Industrial Science And Technology | Polyvinyl alcohol-styrylpyridinium photosensitive resins and method for manufacture thereof |
CA1268732C (en) | 1984-12-27 | 1990-05-08 | Radiation-polymerizing water-soluble cast vinyl monomer layer and forming particles | |
DE3601518A1 (en) * | 1985-01-18 | 1986-07-24 | Toagosei Chemical Industrial Co., Ltd., Tokio/Tokyo | PRIMER |
DE3814135A1 (en) | 1987-05-06 | 1988-11-24 | Wilkinson Sword Gmbh | METHOD FOR PRODUCING A HYDROPHILIC COATING ON A MOLDED PART AND USING THE METHOD OF A SHAVER |
US4874822A (en) * | 1988-04-07 | 1989-10-17 | Minnesota Mining And Manufacturing Company | Process for the acrylamidoacylation of alcohols |
US5091205A (en) | 1989-01-17 | 1992-02-25 | Union Carbide Chemicals & Plastics Technology Corporation | Hydrophilic lubricious coatings |
US5008301A (en) * | 1989-02-21 | 1991-04-16 | Dow Corning Corporation | Ultraviolet curing conformal coating with dual shadow cure |
JPH03250013A (en) * | 1989-06-28 | 1991-11-07 | Ajinomoto Co Inc | Polyether acrylamide derivative and actinic radiation-curing resin composition containing the same |
JP3162696B2 (en) | 1989-09-06 | 2001-05-08 | ライオン株式会社 | Water-soluble, salt-sensitive polymer |
US5135516A (en) * | 1989-12-15 | 1992-08-04 | Boston Scientific Corporation | Lubricious antithrombogenic catheters, guidewires and coatings |
US5084315A (en) | 1990-02-01 | 1992-01-28 | Becton, Dickinson And Company | Lubricious coatings, medical articles containing same and method for their preparation |
US5077352A (en) | 1990-04-23 | 1991-12-31 | C. R. Bard, Inc. | Flexible lubricious organic coatings |
DK146790D0 (en) | 1990-06-15 | 1990-06-15 | Meadox Surgimed As | PROCEDURE FOR THE PREPARATION OF A FERTILIZER COATING COATING AND MEDICAL INSTRUMENT WITH COATING COATING |
JPH0783761B2 (en) | 1990-10-04 | 1995-09-13 | テルモ株式会社 | Medical equipment |
JP3250013B2 (en) | 1992-02-27 | 2002-01-28 | キョーラク株式会社 | Blow molding hollow body fixing structure |
JP3227618B2 (en) | 1992-07-24 | 2001-11-12 | 昭和電工株式会社 | Manufacturing method of pre-coated fin material for heat exchanger |
US5531715A (en) | 1993-05-12 | 1996-07-02 | Target Therapeutics, Inc. | Lubricious catheters |
US5670557A (en) | 1994-01-28 | 1997-09-23 | Minnesota Mining And Manufacturing Company | Polymerized microemulsion pressure sensitive adhesive compositions and methods of preparing and using same |
US5700559A (en) | 1994-12-16 | 1997-12-23 | Advanced Surface Technology | Durable hydrophilic surface coatings |
US5919570A (en) | 1995-02-01 | 1999-07-06 | Schneider Inc. | Slippery, tenaciously adhering hydrogel coatings containing a polyurethane-urea polymer hydrogel commingled with a poly(N-vinylpyrrolidone) polymer hydrogel, coated polymer and metal substrate materials, and coated medical devices |
US6558798B2 (en) | 1995-02-22 | 2003-05-06 | Scimed Life Systems, Inc. | Hydrophilic coating and substrates coated therewith having enhanced durability and lubricity |
US5702754A (en) | 1995-02-22 | 1997-12-30 | Meadox Medicals, Inc. | Method of providing a substrate with a hydrophilic coating and substrates, particularly medical devices, provided with such coatings |
GB9504996D0 (en) | 1995-03-11 | 1995-04-26 | Zeneca Ltd | Compositions |
US7767631B2 (en) | 1995-06-07 | 2010-08-03 | Lee County Mosquito Control District | Lubricant compositions and methods |
US5804318A (en) | 1995-10-26 | 1998-09-08 | Corvita Corporation | Lubricious hydrogel surface modification |
GB9522683D0 (en) | 1995-11-06 | 1996-01-10 | Coates Brothers Plc | Photoinitiator |
US5985990A (en) | 1995-12-29 | 1999-11-16 | 3M Innovative Properties Company | Use of pendant free-radically polymerizable moieties with polar polymers to prepare hydrophilic pressure sensitive adhesive compositions |
JP2000507997A (en) | 1996-02-09 | 2000-06-27 | サーフェス ソルーションズ ラボラトリーズ インコーポレイテッド | Aqueous hydrophilic coating composition and articles made therefrom |
FR2755693B1 (en) | 1996-11-14 | 1998-12-18 | Atochem Elf Sa | PROCESS FOR OBTAINING HYDROPHILIC POLYMERS WITH HIGH SPEED OF DISSOLUTION OR SWELLING IN WATER |
JPH10211273A (en) | 1997-01-29 | 1998-08-11 | Sumitomo Bakelite Co Ltd | Medical tool |
JPH10277144A (en) | 1997-04-02 | 1998-10-20 | Nippon Zeon Co Ltd | Surface lubricated medical tool |
US5877243A (en) | 1997-05-05 | 1999-03-02 | Icet, Inc. | Encrustation and bacterial resistant coatings for medical applications |
WO1998058989A1 (en) | 1997-06-20 | 1998-12-30 | Coloplast A/S | A hydrophilic coating and a method for the preparation thereof |
JPH11172149A (en) | 1997-10-09 | 1999-06-29 | Kuraray Co Ltd | Polymer molding product with hydrophilic surface and its production |
US6310116B1 (en) | 1997-10-09 | 2001-10-30 | Kuraray Co., Ltd. | Molded polymer article having a hydrophilic surface and process for producing the same |
US6221425B1 (en) * | 1998-01-30 | 2001-04-24 | Advanced Cardiovascular Systems, Inc. | Lubricious hydrophilic coating for an intracorporeal medical device |
US6896874B2 (en) | 1998-05-26 | 2005-05-24 | Wisconsin Alumni Research Foundation | MR-signal emitting coatings |
US6110451A (en) | 1998-12-18 | 2000-08-29 | Calgon Corporation | Synergistic combination of cationic and ampholytic polymers for cleansing and/or conditioning keratin based substrates |
US6835783B1 (en) | 1999-02-24 | 2004-12-28 | Dow Global Technologies Inc. | Manufacture of superabsorbents in high internal phase emulsions |
US6565981B1 (en) | 1999-03-30 | 2003-05-20 | Stockhausen Gmbh & Co. Kg | Polymers that are cross-linkable to form superabsorbent polymers |
US6673053B2 (en) | 1999-05-07 | 2004-01-06 | Scimed Life Systems, Inc. | Hydrophilic lubricity coating for medical devices comprising an antiblock agent |
US6610035B2 (en) | 1999-05-21 | 2003-08-26 | Scimed Life Systems, Inc. | Hydrophilic lubricity coating for medical devices comprising a hybrid top coat |
JP3512355B2 (en) | 1999-06-17 | 2004-03-29 | クリエートメディック株式会社 | Medical device with lubricity |
EP1065738A1 (en) | 1999-06-28 | 2001-01-03 | Samhwa Paints Ind. Co., Ltd. | Coating material for shielding electromagnetic waves |
WO2001051103A1 (en) | 2000-01-12 | 2001-07-19 | Alcon Universal Ltd. | Coating of implantable ophthalmic lenses to reduce edge glare |
US6589665B2 (en) | 2000-05-30 | 2003-07-08 | Novartis Ag | Coated articles |
DE10043151A1 (en) | 2000-08-31 | 2002-03-28 | Peter Steinruecke | Bone cement with antimicrobial effectiveness |
EP1381447B1 (en) | 2001-04-27 | 2007-01-24 | Millipore Corporation | Coated membranes |
US6673453B2 (en) | 2001-06-12 | 2004-01-06 | Biocoat Incorporated | Coatings appropriate for medical devices |
DE10146050B4 (en) | 2001-09-18 | 2007-11-29 | Bio-Gate Ag | Process for the preparation of an antimicrobial adhesive and coating material |
WO2003035278A1 (en) | 2001-10-25 | 2003-05-01 | Massachusetts Institute Of Technology | Method of depositing polyelectrolyte multilayers and articles coated thereby |
US20030100830A1 (en) | 2001-11-27 | 2003-05-29 | Sheng-Ping Zhong | Implantable or insertable medical devices visible under magnetic resonance imaging |
US20040143180A1 (en) | 2001-11-27 | 2004-07-22 | Sheng-Ping Zhong | Medical devices visible under magnetic resonance imaging |
TWI239340B (en) | 2001-12-06 | 2005-09-11 | Nippon Catalytic Chem Ind | Process for production of water-soluble (meth)acrylic polymers, water-soluble (meth)acrylic polymers, and use thereof |
JP2005526972A (en) | 2002-05-02 | 2005-09-08 | シファーゲン バイオシステムズ, インコーポレイテッド | Biochip with surface coated with polysaccharide hydrogel |
US6887961B2 (en) | 2002-07-26 | 2005-05-03 | Kimberly-Clark Worldwide, Inc. | Absorbent binder composition and method of making it |
US7115321B2 (en) | 2002-07-26 | 2006-10-03 | Kimberly-Clark Worldwide, Inc. | Absorbent binder coating |
US6737491B2 (en) | 2002-07-26 | 2004-05-18 | Kimberly-Clark Worldwide, Inc. | Absorbent binder composition and method of making same |
US6720130B1 (en) * | 2002-10-08 | 2004-04-13 | Kodak Polychrome Graphics Llc | Radiation sensitive lithographic printing plate precursors having ablation-free imageable composition and method |
US7288578B2 (en) | 2002-11-01 | 2007-10-30 | Novartis Ag | Biocompatible inks, preparation, and uses thereof |
US8172395B2 (en) | 2002-12-03 | 2012-05-08 | Novartis Ag | Medical devices having antimicrobial coatings thereon |
US20040161444A1 (en) * | 2002-12-18 | 2004-08-19 | The Regents Of The University Of California | Biocompatible hydrogel bone-like composites |
US7264859B2 (en) | 2002-12-19 | 2007-09-04 | Kimberly-Clark Worldwide, Inc. | Lubricious coating for medical devices |
JP2006510756A (en) | 2002-12-20 | 2006-03-30 | コロプラスト アクティーゼルスカブ | Hydrophilic coatings and methods for preparing them |
IES20030294A2 (en) | 2003-04-17 | 2004-10-20 | Medtronic Vascular Connaught | Coating for biomedical devices |
US7544381B2 (en) | 2003-09-09 | 2009-06-09 | Boston Scientific Scimed, Inc. | Lubricious coatings for medical device |
US20050054774A1 (en) * | 2003-09-09 | 2005-03-10 | Scimed Life Systems, Inc. | Lubricious coating |
WO2005037338A1 (en) | 2003-10-14 | 2005-04-28 | Cook Incorporated | Hydrophilic coated medical device |
SE0303525D0 (en) * | 2003-12-22 | 2003-12-22 | Astra Tech Ab | Catheter assembly with osmolality-increasing |
US7534495B2 (en) | 2004-01-29 | 2009-05-19 | Boston Scientific Scimed, Inc. | Lubricious composition |
DE102004050868A1 (en) | 2004-10-18 | 2006-04-20 | Dreve Otoplastik Gmbh | Low-viscosity, radiation-curable formulation for the production of ear molds |
US7335690B2 (en) * | 2005-01-25 | 2008-02-26 | 3M Innovative Properties Company | Crosslinkable hydrophilic materials from polymers having pendent Michael donor groups |
US20060240060A1 (en) | 2005-04-22 | 2006-10-26 | Cardiac Pacemakers, Inc. | Lubricious compound and medical device made of the same |
DE102005050186A1 (en) | 2005-10-18 | 2007-04-19 | Dreve Otoplastik Gmbh | Low viscosity, radiation-hardenable composition for antimicrobial medical products, especially adaptive ear pieces, is based on e.g. (meth)acrylates, glass or silver antimicrobials and photoinitiators |
WO2007065722A1 (en) | 2005-12-09 | 2007-06-14 | Dsm Ip Assets B.V. | Hydrophilic coating comprising a polyelectrolyte |
EP2389960B1 (en) * | 2006-06-15 | 2018-02-28 | MicroVention, Inc. | Environmentally responsive hydrogel |
EP2679254A1 (en) | 2006-07-25 | 2014-01-01 | Coloplast A/S | Photo-curing of thermoplastic coatings |
US20100113871A1 (en) | 2006-09-13 | 2010-05-06 | Aylvin Jorge Angelo Athanasius Dias | Antimicrobial coating |
EP2059272B1 (en) | 2006-09-13 | 2018-02-28 | DSM IP Assets B.V. | Coating formulation for medical coating |
EP2104523B1 (en) | 2006-12-15 | 2015-08-26 | Coloplast A/S | Coatings prepared from poly(ethylene oxide) and photo-initator-containing scaffolds |
EP2125061A2 (en) | 2007-02-28 | 2009-12-02 | DSM IP Assets B.V. | Hydrophilic coating |
JP5587611B2 (en) | 2007-02-28 | 2014-09-10 | ディーエスエム アイピー アセッツ ビー.ブイ. | Hydrophilic coating |
DK2252661T3 (en) | 2008-03-12 | 2017-01-16 | Dsm Ip Assets Bv | HYDROPHIL COATING |
-
2007
- 2007-09-13 EP EP07818144.3A patent/EP2059272B1/en active Active
- 2007-09-13 EP EP07802301.7A patent/EP2061526B1/en active Active
- 2007-09-13 JP JP2009527743A patent/JP5499321B2/en active Active
- 2007-09-13 WO PCT/EP2007/007985 patent/WO2008031596A1/en active Application Filing
- 2007-09-13 WO PCT/EP2007/007984 patent/WO2008031595A2/en active Application Filing
- 2007-09-13 JP JP2009527742A patent/JP5552690B2/en active Active
- 2007-09-13 US US12/440,532 patent/US8828546B2/en active Active
- 2007-09-13 US US12/440,775 patent/US20100076546A1/en not_active Abandoned
-
2013
- 2013-12-13 US US14/106,425 patent/US20140180221A1/en not_active Abandoned
-
2016
- 2016-01-28 US US15/009,747 patent/US20160310643A1/en not_active Abandoned
Patent Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0405464A2 (en) * | 1989-06-28 | 1991-01-02 | Ajinomoto Co., Inc. | Polyether acrylamide derivatives and active energy ray curable resin composition |
WO1997014448A1 (en) * | 1995-10-17 | 1997-04-24 | Ajay Kumar Luthra | Biocompatible lubricious hydrophilic materials for medical devices |
WO2001092584A1 (en) * | 2000-06-02 | 2001-12-06 | Eidgenossische Technische Hochschule Zurich | Conjugate addition reactions for the controlled delivery of pharmaceutically active compounds |
WO2006056482A1 (en) * | 2004-11-29 | 2006-06-01 | Dsm Ip Assets B.V. | Method for reducing the amount of migrateables of polymer coatings |
Non-Patent Citations (1)
Title |
---|
ZIMMERMAN J ET AL: "Novel hydrogels as supports for in vitro growth: (meth)acrylamidopeptide macromers", BIOMATERIALS, vol. 23, no. 10, May 2002 (2002-05-01), barking, GB, pages 2127 - 2134, XP004348208 * |
Cited By (34)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US9737637B2 (en) | 2004-11-29 | 2017-08-22 | Dsm Ip Assets B.V. | Method for reducing the amount of migrateables of polymer coatings |
US8871869B2 (en) | 2005-12-09 | 2014-10-28 | Dsm Ip Assets B.V. | Hydrophilic coating |
US8512795B2 (en) | 2005-12-09 | 2013-08-20 | Dsm Ip Assets B.V. | Hydrophilic coating comprising a polyelectrolyte |
US8828546B2 (en) | 2006-09-13 | 2014-09-09 | Dsm Ip Assets B.V. | Coated medical device |
US8809411B2 (en) | 2007-02-28 | 2014-08-19 | Dsm Ip Assets B.V. | Hydrophilic coating |
US8513320B2 (en) | 2007-02-28 | 2013-08-20 | Dsm Ip Assets B.V. | Hydrophilic coating |
EP2183105A2 (en) * | 2007-08-27 | 2010-05-12 | 3M Innovative Properties Company | Polymer gel structure and method for producing same |
EP2183105A4 (en) * | 2007-08-27 | 2011-05-18 | 3M Innovative Properties Co | Polymer gel structure and method for producing same |
WO2009112548A1 (en) * | 2008-03-12 | 2009-09-17 | Dsm Ip Assets B.V. | Hydrophilic coating |
US9132211B2 (en) | 2008-09-15 | 2015-09-15 | The Spectranetics Corporation | Local delivery of water-soluble or water-insoluble therapeutic agents to the surface of body lumens |
US9603973B2 (en) | 2008-09-15 | 2017-03-28 | The Spectranetics Corporation | Local delivery of water-soluble or water-insoluble therapeutic agents to the surface of body lumens |
US10987452B2 (en) | 2008-09-15 | 2021-04-27 | The Spectranetics Corporation | Local delivery of water-soluble or water-insoluble therapeutic agents to the surface of body lumens |
US10314948B2 (en) | 2008-09-15 | 2019-06-11 | The Spectranetics Coporation | Local delivery of water-soluble or water-insoluble therapeutic agents to the surface of body lumens |
US10117970B2 (en) | 2008-09-15 | 2018-11-06 | The Spectranetics Corporation | Local delivery of water-soluble or water-insoluble therapeutic agents to the surface of body lumens |
US10046093B2 (en) | 2008-09-15 | 2018-08-14 | The Spectranetics Corporation | Local delivery of water-soluble or water-insoluble therapeutic agents to the surface of body lumens |
US9034362B2 (en) | 2008-09-15 | 2015-05-19 | The Spectranetics Corporation | Local delivery of water-soluble or water-insoluble therapeutic agents to the surface of body lumens |
US9198968B2 (en) | 2008-09-15 | 2015-12-01 | The Spectranetics Corporation | Local delivery of water-soluble or water-insoluble therapeutic agents to the surface of body lumens |
JP2012502690A (en) * | 2008-09-15 | 2012-02-02 | シーヴィー インジェニュイティ コーポレイション | Local delivery of water-soluble or water-insoluble therapeutic agents to the body lumen surface |
AU2010226929B2 (en) * | 2009-10-16 | 2014-07-24 | Confluent Surgical, Inc. | Prevention of premature gelling of delivery devices for pH dependent forming materials |
JP2013520277A (en) * | 2010-02-24 | 2013-06-06 | シーヴィー インジェニュイティ コーポレイション | Local delivery of water-soluble or water-insoluble therapeutic agents to the body lumen surface |
US9238715B2 (en) | 2010-05-27 | 2016-01-19 | Nanyang Technological University | Polymerizable composition for ophthalmic and medical use and antimicrobial composition obtained by polymerizing the polymerizable composition |
US8957125B2 (en) | 2010-06-16 | 2015-02-17 | Dsm Ip Assets B.V. | Coating formulation for preparing a hydrophilic coating |
WO2013110566A1 (en) | 2012-01-27 | 2013-08-01 | Basf Se | Radiation-curable anti-microbial coating compound |
US8728455B2 (en) | 2012-01-27 | 2014-05-20 | Basf Se | Radiation-curable antimicrobial coatings |
WO2013110504A1 (en) | 2012-01-27 | 2013-08-01 | Basf Se | Radiation-curable antimicrobial coatings |
US9956385B2 (en) | 2012-06-28 | 2018-05-01 | The Spectranetics Corporation | Post-processing of a medical device to control morphology and mechanical properties |
US9901663B2 (en) | 2013-05-06 | 2018-02-27 | Abbott Cardiovascular Systems Inc. | Hollow stent filled with a therapeutic agent formulation |
EP3037454A4 (en) * | 2013-08-20 | 2017-05-24 | Boe Technology Group Co. Ltd. | Polyether compound, preparation method and photoresist composition thereof |
US10525171B2 (en) | 2014-01-24 | 2020-01-07 | The Spectranetics Corporation | Coatings for medical devices |
US10978277B2 (en) | 2015-05-11 | 2021-04-13 | Nova Plasma Ltd. | Apparatus and method for handling an implant |
EP3294351B1 (en) * | 2015-05-11 | 2022-03-23 | Nova Plasma Ltd | Method for preparing a silicone implant using plasma processing |
US11955321B2 (en) | 2015-05-11 | 2024-04-09 | Nova Plasma Ltd. | Method for handling an implant |
WO2016200337A1 (en) | 2015-06-08 | 2016-12-15 | Jmedtech Pte Ltd | Coating compositions comprising adhesion promoting base layer |
WO2021233743A1 (en) | 2020-05-18 | 2021-11-25 | Dsm Ip Assets B.V. | Coating composition, method of making a hydrophilic coating on a substrate, and medical device comprising such coating |
Also Published As
Publication number | Publication date |
---|---|
JP5552690B2 (en) | 2014-07-16 |
JP5499321B2 (en) | 2014-05-21 |
US20100114042A1 (en) | 2010-05-06 |
US20140180221A1 (en) | 2014-06-26 |
US8828546B2 (en) | 2014-09-09 |
EP2061526B1 (en) | 2015-07-29 |
US20100076546A1 (en) | 2010-03-25 |
JP2010503436A (en) | 2010-02-04 |
JP2010506828A (en) | 2010-03-04 |
EP2061526A2 (en) | 2009-05-27 |
WO2008031595A3 (en) | 2008-06-05 |
US20160310643A1 (en) | 2016-10-27 |
EP2059272B1 (en) | 2018-02-28 |
EP2059272A1 (en) | 2009-05-20 |
WO2008031595A2 (en) | 2008-03-20 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
EP2059272B1 (en) | Coating formulation for medical coating | |
US8809411B2 (en) | Hydrophilic coating | |
JP5521237B2 (en) | Hydrophilic coating | |
US8513320B2 (en) | Hydrophilic coating | |
US8871869B2 (en) | Hydrophilic coating | |
EP2252661B1 (en) | Hydrophilic coating | |
MX2008007380A (en) | Hydrophilic coating comprising a polyelectrolyte |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
121 | Ep: the epo has been informed by wipo that ep was designated in this application |
Ref document number: 07818144 Country of ref document: EP Kind code of ref document: A1 |
|
ENP | Entry into the national phase |
Ref document number: 2009527743 Country of ref document: JP Kind code of ref document: A |
|
NENP | Non-entry into the national phase |
Ref country code: DE |
|
WWE | Wipo information: entry into national phase |
Ref document number: 2007818144 Country of ref document: EP |
|
WWE | Wipo information: entry into national phase |
Ref document number: 12440775 Country of ref document: US |