DE60314131T2 - Silan-beschichtungszusammensetzung - Google Patents
Silan-beschichtungszusammensetzung Download PDFInfo
- Publication number
- DE60314131T2 DE60314131T2 DE2003614131 DE60314131T DE60314131T2 DE 60314131 T2 DE60314131 T2 DE 60314131T2 DE 2003614131 DE2003614131 DE 2003614131 DE 60314131 T DE60314131 T DE 60314131T DE 60314131 T2 DE60314131 T2 DE 60314131T2
- Authority
- DE
- Germany
- Prior art keywords
- article
- coating layer
- salt
- hydrophilic polymer
- bis
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- 229910000077 silane Inorganic materials 0.000 title claims description 66
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 title description 17
- 239000008199 coating composition Substances 0.000 title description 4
- 239000011247 coating layer Substances 0.000 claims description 156
- 239000004971 Cross linker Substances 0.000 claims description 87
- -1 silane compound Chemical class 0.000 claims description 84
- 229920001477 hydrophilic polymer Polymers 0.000 claims description 61
- 229910052751 metal Inorganic materials 0.000 claims description 59
- 239000002184 metal Substances 0.000 claims description 59
- 239000000758 substrate Substances 0.000 claims description 46
- 239000010410 layer Substances 0.000 claims description 43
- 239000000178 monomer Substances 0.000 claims description 43
- 239000007795 chemical reaction product Substances 0.000 claims description 36
- 239000000203 mixture Substances 0.000 claims description 31
- WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 claims description 27
- 150000003839 salts Chemical class 0.000 claims description 23
- 238000006460 hydrolysis reaction Methods 0.000 claims description 22
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims description 20
- 229920000642 polymer Polymers 0.000 claims description 18
- 150000001875 compounds Chemical class 0.000 claims description 14
- 238000000034 method Methods 0.000 claims description 11
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical group [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 claims description 11
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 claims description 10
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 claims description 10
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 10
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 claims description 10
- 229910052737 gold Inorganic materials 0.000 claims description 10
- 239000010931 gold Substances 0.000 claims description 10
- 229910052741 iridium Inorganic materials 0.000 claims description 10
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 claims description 10
- 229910052697 platinum Inorganic materials 0.000 claims description 10
- 239000010935 stainless steel Substances 0.000 claims description 10
- 229910001220 stainless steel Inorganic materials 0.000 claims description 10
- IJBXHSUZEBBJJG-UHFFFAOYSA-N (4-benzoylphenyl)methyl-[2-[(4-benzoylphenyl)methyl-dimethylazaniumyl]ethyl]-dimethylazanium Chemical class C=1C=C(C(=O)C=2C=CC=CC=2)C=CC=1C[N+](C)(C)CC[N+](C)(C)CC(C=C1)=CC=C1C(=O)C1=CC=CC=C1 IJBXHSUZEBBJJG-UHFFFAOYSA-N 0.000 claims description 9
- XNOMWKDAQZCFGK-UHFFFAOYSA-N [4-[(4-benzoylphenyl)methoxymethyl]phenyl]-phenylmethanone Chemical compound C=1C=C(COCC=2C=CC(=CC=2)C(=O)C=2C=CC=CC=2)C=CC=1C(=O)C1=CC=CC=C1 XNOMWKDAQZCFGK-UHFFFAOYSA-N 0.000 claims description 9
- 125000003118 aryl group Chemical group 0.000 claims description 9
- 125000000468 ketone group Chemical group 0.000 claims description 9
- FQPSGWSUVKBHSU-UHFFFAOYSA-N methacrylamide Chemical compound CC(=C)C(N)=O FQPSGWSUVKBHSU-UHFFFAOYSA-N 0.000 claims description 9
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 claims description 9
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 8
- 125000005370 alkoxysilyl group Chemical group 0.000 claims description 8
- WRUAHXANJKHFIL-UHFFFAOYSA-N benzene-1,3-disulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC(S(O)(=O)=O)=C1 WRUAHXANJKHFIL-UHFFFAOYSA-N 0.000 claims description 8
- 239000002253 acid Substances 0.000 claims description 7
- 150000008040 ionic compounds Chemical class 0.000 claims description 7
- 125000000101 thioether group Chemical group 0.000 claims description 7
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 6
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 6
- 229920002554 vinyl polymer Polymers 0.000 claims description 6
- 229910045601 alloy Inorganic materials 0.000 claims description 5
- 239000000956 alloy Substances 0.000 claims description 5
- 125000006850 spacer group Chemical group 0.000 claims description 5
- MAFQBSQRZKWGGE-UHFFFAOYSA-N trimethoxy-[2-[4-(2-trimethoxysilylethyl)phenyl]ethyl]silane Chemical compound CO[Si](OC)(OC)CCC1=CC=C(CC[Si](OC)(OC)OC)C=C1 MAFQBSQRZKWGGE-UHFFFAOYSA-N 0.000 claims description 5
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 4
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims description 4
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 4
- 229920000615 alginic acid Polymers 0.000 claims description 4
- 235000010443 alginic acid Nutrition 0.000 claims description 4
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims description 3
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 claims description 3
- 230000000747 cardiac effect Effects 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 239000010936 titanium Substances 0.000 claims description 3
- 230000002792 vascular Effects 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
- WCDDVEOXEIYWFB-VXORFPGASA-N (2s,3s,4r,5r,6r)-3-[(2s,3r,5s,6r)-3-acetamido-5-hydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4,5,6-trihydroxyoxane-2-carboxylic acid Chemical compound CC(=O)N[C@@H]1C[C@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](C(O)=O)O[C@@H](O)[C@H](O)[C@H]1O WCDDVEOXEIYWFB-VXORFPGASA-N 0.000 claims description 2
- PGOQAHNIFXPYQR-UHFFFAOYSA-N (4-benzoylphenyl)methyl-[6-[(4-benzoylphenyl)methyl-dimethylazaniumyl]hexyl]-dimethylazanium Chemical class C=1C=C(C(=O)C=2C=CC=CC=2)C=CC=1C[N+](C)(C)CCCCCC[N+](C)(C)CC(C=C1)=CC=C1C(=O)C1=CC=CC=C1 PGOQAHNIFXPYQR-UHFFFAOYSA-N 0.000 claims description 2
- JMVZUADCGPOVDM-UHFFFAOYSA-N 2-[2-(4-benzoylphenyl)ethyl-[2-[(4-benzoylphenyl)methyl-dimethylazaniumyl]ethyl]amino]ethyl-[(4-benzoylphenyl)methyl]-dimethylazanium Chemical class C=1C=C(C(=O)C=2C=CC=CC=2)C=CC=1C[N+](C)(C)CCN(CC[N+](C)(C)CC=1C=CC(=CC=1)C(=O)C=1C=CC=CC=1)CCC(C=C1)=CC=C1C(=O)C1=CC=CC=C1 JMVZUADCGPOVDM-UHFFFAOYSA-N 0.000 claims description 2
- RWDSKJNFYUOSRD-UHFFFAOYSA-N 2-[2-(4-benzoylphenyl)ethyl-[2-[2-(4-benzoylphenyl)ethyl-[2-[(4-benzoylphenyl)methyl-dimethylazaniumyl]ethyl]amino]ethyl]amino]ethyl-[(4-benzoylphenyl)methyl]-dimethylazanium Chemical class C=1C=C(C(=O)C=2C=CC=CC=2)C=CC=1C[N+](C)(C)CCN(CCC=1C=CC(=CC=1)C(=O)C=1C=CC=CC=1)CCN(CC[N+](C)(C)CC=1C=CC(=CC=1)C(=O)C=1C=CC=CC=1)CCC(C=C1)=CC=C1C(=O)C1=CC=CC=C1 RWDSKJNFYUOSRD-UHFFFAOYSA-N 0.000 claims description 2
- NRTABCXMDFHEGK-UHFFFAOYSA-N 2-[bis[2-[(4-benzoylphenyl)methoxy]ethyl]amino]ethanesulfonic acid Chemical compound C=1C=C(C(=O)C=2C=CC=CC=2)C=CC=1COCCN(CCS(=O)(=O)O)CCOCC(C=C1)=CC=C1C(=O)C1=CC=CC=C1 NRTABCXMDFHEGK-UHFFFAOYSA-N 0.000 claims description 2
- FHVDTGUDJYJELY-UHFFFAOYSA-N 6-{[2-carboxy-4,5-dihydroxy-6-(phosphanyloxy)oxan-3-yl]oxy}-4,5-dihydroxy-3-phosphanyloxane-2-carboxylic acid Chemical compound O1C(C(O)=O)C(P)C(O)C(O)C1OC1C(C(O)=O)OC(OP)C(O)C1O FHVDTGUDJYJELY-UHFFFAOYSA-N 0.000 claims description 2
- 206010002329 Aneurysm Diseases 0.000 claims description 2
- 229920001661 Chitosan Polymers 0.000 claims description 2
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 claims description 2
- 102000008186 Collagen Human genes 0.000 claims description 2
- 108010035532 Collagen Proteins 0.000 claims description 2
- 229920002307 Dextran Polymers 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
- 108010039918 Polylysine Proteins 0.000 claims description 2
- FJZHZZPMKUROCW-UHFFFAOYSA-N [4-[[4-[(4-benzoylphenyl)methyl]morpholin-4-ium-4-yl]methyl]phenyl]-phenylmethanone Chemical class C=1C=C(C[N+]2(CC=3C=CC(=CC=3)C(=O)C=3C=CC=CC=3)CCOCC2)C=CC=1C(=O)C1=CC=CC=C1 FJZHZZPMKUROCW-UHFFFAOYSA-N 0.000 claims description 2
- 229940072056 alginate Drugs 0.000 claims description 2
- 239000000783 alginic acid Substances 0.000 claims description 2
- 229960001126 alginic acid Drugs 0.000 claims description 2
- 150000004781 alginic acids Chemical class 0.000 claims description 2
- OATNQHYJXLHTEW-UHFFFAOYSA-N benzene-1,4-disulfonic acid Chemical compound OS(=O)(=O)C1=CC=C(S(O)(=O)=O)C=C1 OATNQHYJXLHTEW-UHFFFAOYSA-N 0.000 claims description 2
- SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 claims description 2
- 239000001913 cellulose Substances 0.000 claims description 2
- 229920002678 cellulose Polymers 0.000 claims description 2
- 229910010293 ceramic material Inorganic materials 0.000 claims description 2
- 229910052804 chromium Inorganic materials 0.000 claims description 2
- 239000011651 chromium Substances 0.000 claims description 2
- 229910017052 cobalt Inorganic materials 0.000 claims description 2
- 239000010941 cobalt Substances 0.000 claims description 2
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 claims description 2
- 229920001436 collagen Polymers 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
- 239000011521 glass Substances 0.000 claims description 2
- 208000025339 heart septal defect Diseases 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
- 229940014041 hyaluronate Drugs 0.000 claims description 2
- 229960003160 hyaluronic acid Drugs 0.000 claims description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 claims description 2
- 229910052742 iron Inorganic materials 0.000 claims description 2
- 239000011707 mineral Substances 0.000 claims description 2
- 229910052759 nickel Inorganic materials 0.000 claims description 2
- 229910001000 nickel titanium Inorganic materials 0.000 claims description 2
- HLXZNVUGXRDIFK-UHFFFAOYSA-N nickel titanium Chemical compound [Ti].[Ti].[Ti].[Ti].[Ti].[Ti].[Ti].[Ti].[Ti].[Ti].[Ti].[Ni].[Ni].[Ni].[Ni].[Ni].[Ni].[Ni].[Ni].[Ni].[Ni].[Ni].[Ni].[Ni].[Ni] HLXZNVUGXRDIFK-UHFFFAOYSA-N 0.000 claims description 2
- 230000000399 orthopedic effect Effects 0.000 claims description 2
- 229910052763 palladium Inorganic materials 0.000 claims description 2
- 229920003023 plastic Polymers 0.000 claims description 2
- 239000004033 plastic Substances 0.000 claims description 2
- 229920000656 polylysine Polymers 0.000 claims description 2
- 150000003460 sulfonic acids Chemical class 0.000 claims description 2
- RWSOTUBLDIXVET-UHFFFAOYSA-O sulfonium Chemical compound [SH3+] RWSOTUBLDIXVET-UHFFFAOYSA-O 0.000 claims description 2
- 229910052715 tantalum Inorganic materials 0.000 claims description 2
- GUVRBAGPIYLISA-UHFFFAOYSA-N tantalum atom Chemical compound [Ta] GUVRBAGPIYLISA-UHFFFAOYSA-N 0.000 claims description 2
- 229910052719 titanium Inorganic materials 0.000 claims description 2
- JBYXACURRYATNJ-UHFFFAOYSA-N trimethoxy(1-trimethoxysilylhexyl)silane Chemical compound CCCCCC([Si](OC)(OC)OC)[Si](OC)(OC)OC JBYXACURRYATNJ-UHFFFAOYSA-N 0.000 claims description 2
- JCGDCINCKDQXDX-UHFFFAOYSA-N trimethoxy(2-trimethoxysilylethyl)silane Chemical compound CO[Si](OC)(OC)CC[Si](OC)(OC)OC JCGDCINCKDQXDX-UHFFFAOYSA-N 0.000 claims description 2
- ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical compound OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 claims 1
- 229910052782 aluminium Inorganic materials 0.000 claims 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims 1
- 239000003431 cross linking reagent Substances 0.000 claims 1
- 125000005496 phosphonium group Chemical group 0.000 claims 1
- 238000000576 coating method Methods 0.000 description 69
- 239000011248 coating agent Substances 0.000 description 64
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 34
- 239000000243 solution Substances 0.000 description 30
- 230000000052 comparative effect Effects 0.000 description 22
- 239000008399 tap water Substances 0.000 description 15
- 235000020679 tap water Nutrition 0.000 description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical group O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 13
- HFHIDKQMGIGARX-UHFFFAOYSA-N 3,3'-(biphenyl-4,4'-diyldidiazene-2,1-diyl)bis(4-aminonaphthalene-1-sulfonic acid) Chemical compound C1=CC=CC2=C(N)C(N=NC3=CC=C(C=C3)C3=CC=C(C=C3)N=NC3=C(C4=CC=CC=C4C(=C3)S(O)(=O)=O)N)=CC(S(O)(=O)=O)=C21 HFHIDKQMGIGARX-UHFFFAOYSA-N 0.000 description 12
- 239000007864 aqueous solution Substances 0.000 description 12
- 210000005224 forefinger Anatomy 0.000 description 12
- 238000010186 staining Methods 0.000 description 12
- 210000003813 thumb Anatomy 0.000 description 12
- 238000005406 washing Methods 0.000 description 12
- 229920001577 copolymer Polymers 0.000 description 8
- 239000010970 precious metal Substances 0.000 description 8
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 6
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- 239000002585 base Substances 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 5
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 4
- 125000000129 anionic group Chemical group 0.000 description 4
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 4
- 239000008367 deionised water Substances 0.000 description 4
- 229910021641 deionized water Inorganic materials 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 238000003491 array Methods 0.000 description 3
- 239000012965 benzophenone Substances 0.000 description 3
- 125000002091 cationic group Chemical group 0.000 description 3
- 125000000623 heterocyclic group Chemical group 0.000 description 3
- 229920001519 homopolymer Polymers 0.000 description 3
- GUAQVFRUPZBRJQ-UHFFFAOYSA-N n-(3-aminopropyl)-2-methylprop-2-enamide Chemical compound CC(=C)C(=O)NCCCN GUAQVFRUPZBRJQ-UHFFFAOYSA-N 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- 229920002818 (Hydroxyethyl)methacrylate Polymers 0.000 description 2
- QRIMLDXJAPZHJE-UHFFFAOYSA-N 2,3-dihydroxypropyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCC(O)CO QRIMLDXJAPZHJE-UHFFFAOYSA-N 0.000 description 2
- OWPUOLBODXJOKH-UHFFFAOYSA-N 2,3-dihydroxypropyl prop-2-enoate Chemical compound OCC(O)COC(=O)C=C OWPUOLBODXJOKH-UHFFFAOYSA-N 0.000 description 2
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 2
- OMIGHNLMNHATMP-UHFFFAOYSA-N 2-hydroxyethyl prop-2-enoate Chemical compound OCCOC(=O)C=C OMIGHNLMNHATMP-UHFFFAOYSA-N 0.000 description 2
- OZCULFZQSHFJNI-UHFFFAOYSA-N 4-benzoylbenzoyl chloride Chemical compound C1=CC(C(=O)Cl)=CC=C1C(=O)C1=CC=CC=C1 OZCULFZQSHFJNI-UHFFFAOYSA-N 0.000 description 2
- 101000623895 Bos taurus Mucin-15 Proteins 0.000 description 2
- IMROMDMJAWUWLK-UHFFFAOYSA-N Ethenol Chemical compound OC=C IMROMDMJAWUWLK-UHFFFAOYSA-N 0.000 description 2
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- WOBHKFSMXKNTIM-UHFFFAOYSA-N Hydroxyethyl methacrylate Chemical compound CC(=C)C(=O)OCCO WOBHKFSMXKNTIM-UHFFFAOYSA-N 0.000 description 2
- 241000124008 Mammalia Species 0.000 description 2
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 2
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 2
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 2
- 238000003436 Schotten-Baumann reaction Methods 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 2
- 230000004913 activation Effects 0.000 description 2
- 150000001263 acyl chlorides Chemical class 0.000 description 2
- 125000004429 atom Chemical group 0.000 description 2
- 230000000975 bioactive effect Effects 0.000 description 2
- 230000001680 brushing effect Effects 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 150000007942 carboxylates Chemical class 0.000 description 2
- 239000000969 carrier Substances 0.000 description 2
- 238000007334 copolymerization reaction Methods 0.000 description 2
- 230000001419 dependent effect Effects 0.000 description 2
- 150000004845 diazirines Chemical class 0.000 description 2
- 150000008049 diazo compounds Chemical class 0.000 description 2
- OBTFKRQJZSUBCQ-UHFFFAOYSA-L dipotassium;benzene-1,3-disulfonate Chemical compound [K+].[K+].[O-]S(=O)(=O)C1=CC=CC(S([O-])(=O)=O)=C1 OBTFKRQJZSUBCQ-UHFFFAOYSA-L 0.000 description 2
- 238000007598 dipping method Methods 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 230000005283 ground state Effects 0.000 description 2
- 150000004820 halides Chemical class 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- 230000002209 hydrophobic effect Effects 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- CPGRMGOILBSUQC-UHFFFAOYSA-N phosphoryl azide Chemical class [N-]=[N+]=NP(=O)(N=[N+]=[N-])N=[N+]=[N-] CPGRMGOILBSUQC-UHFFFAOYSA-N 0.000 description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
- 108090000623 proteins and genes Proteins 0.000 description 2
- 125000004151 quinonyl group Chemical group 0.000 description 2
- 230000005855 radiation Effects 0.000 description 2
- 238000005096 rolling process Methods 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000000527 sonication Methods 0.000 description 2
- 238000005507 spraying Methods 0.000 description 2
- 238000003860 storage Methods 0.000 description 2
- 125000001273 sulfonato group Chemical group [O-]S(*)(=O)=O 0.000 description 2
- 238000002604 ultrasonography Methods 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
- 229910052727 yttrium Inorganic materials 0.000 description 2
- DKBZZUNCOFCQFT-UHFFFAOYSA-L (4-benzoylphenyl)methyl-[2-[(4-benzoylphenyl)methyl-dimethylazaniumyl]ethyl]-dimethylazanium;dibromide Chemical compound [Br-].[Br-].C=1C=C(C(=O)C=2C=CC=CC=2)C=CC=1C[N+](C)(C)CC[N+](C)(C)CC(C=C1)=CC=C1C(=O)C1=CC=CC=C1 DKBZZUNCOFCQFT-UHFFFAOYSA-L 0.000 description 1
- UUORGSXWPOMXJJ-UHFFFAOYSA-N 1-[azido(ethyl)phosphoryl]ethane Chemical compound CCP(=O)(CC)N=[N+]=[N-] UUORGSXWPOMXJJ-UHFFFAOYSA-N 0.000 description 1
- 229920000536 2-Acrylamido-2-methylpropane sulfonic acid Polymers 0.000 description 1
- XHZPRMZZQOIPDS-UHFFFAOYSA-N 2-Methyl-2-[(1-oxo-2-propenyl)amino]-1-propanesulfonic acid Chemical compound OS(=O)(=O)CC(C)(C)NC(=O)C=C XHZPRMZZQOIPDS-UHFFFAOYSA-N 0.000 description 1
- HQNSWBRZIOYGAW-UHFFFAOYSA-N 2-chloro-n,n-dimethylpyridin-4-amine Chemical compound CN(C)C1=CC=NC(Cl)=C1 HQNSWBRZIOYGAW-UHFFFAOYSA-N 0.000 description 1
- QFYSZYAVKZUZCM-UHFFFAOYSA-N 2-diazonio-1,1,1-trifluorohex-2-en-3-olate Chemical compound CCCC(=O)C(=[N+]=[N-])C(F)(F)F QFYSZYAVKZUZCM-UHFFFAOYSA-N 0.000 description 1
- JBVSBLLOZVDAAZ-UHFFFAOYSA-N 2-diazonio-1-[(2-methylpropan-2-yl)oxy]ethenolate Chemical compound CC(C)(C)OC([O-])=C[N+]#N JBVSBLLOZVDAAZ-UHFFFAOYSA-N 0.000 description 1
- UWBALSPTLHOGFE-UHFFFAOYSA-N 2-diazonio-1-phenoxyethenolate Chemical compound [N-]=[N+]=CC(=O)OC1=CC=CC=C1 UWBALSPTLHOGFE-UHFFFAOYSA-N 0.000 description 1
- ZSTBZBURMWJKSQ-UHFFFAOYSA-N 2-diazonio-1-phenylethenolate Chemical compound N#[N+]C=C([O-])C1=CC=CC=C1 ZSTBZBURMWJKSQ-UHFFFAOYSA-N 0.000 description 1
- IXEVBKYJNFWMPR-UHFFFAOYSA-N 3-phenyl-3-(trifluoromethyl)diazirine Chemical compound C=1C=CC=CC=1C1(C(F)(F)F)N=N1 IXEVBKYJNFWMPR-UHFFFAOYSA-N 0.000 description 1
- VCTBSHQJICJJFV-UHFFFAOYSA-N 4-azido-1-fluoro-2-nitrobenzene Chemical compound [O-][N+](=O)C1=CC(N=[N+]=[N-])=CC=C1F VCTBSHQJICJJFV-UHFFFAOYSA-N 0.000 description 1
- RTUYNYSPUHQITK-UHFFFAOYSA-N 4-methylbenzoyl azide Chemical compound CC1=CC=C(C(=O)N=[N+]=[N-])C=C1 RTUYNYSPUHQITK-UHFFFAOYSA-N 0.000 description 1
- GDALETGZDYOOGB-UHFFFAOYSA-N Acridone Natural products C1=C(O)C=C2N(C)C3=CC=CC=C3C(=O)C2=C1O GDALETGZDYOOGB-UHFFFAOYSA-N 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 238000000018 DNA microarray Methods 0.000 description 1
- YXHKONLOYHBTNS-UHFFFAOYSA-N Diazomethane Chemical compound C=[N+]=[N-] YXHKONLOYHBTNS-UHFFFAOYSA-N 0.000 description 1
- 208000010412 Glaucoma Diseases 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 1
- 229910000990 Ni alloy Inorganic materials 0.000 description 1
- BXEFQPCKQSTMKA-UHFFFAOYSA-N OC(=O)C=[N+]=[N-] Chemical class OC(=O)C=[N+]=[N-] BXEFQPCKQSTMKA-UHFFFAOYSA-N 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 229910052581 Si3N4 Inorganic materials 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 229910001069 Ti alloy Inorganic materials 0.000 description 1
- QYKIQEUNHZKYBP-UHFFFAOYSA-N Vinyl ether Chemical compound C=COC=C QYKIQEUNHZKYBP-UHFFFAOYSA-N 0.000 description 1
- QCWXUUIWCKQGHC-UHFFFAOYSA-N Zirconium Chemical compound [Zr] QCWXUUIWCKQGHC-UHFFFAOYSA-N 0.000 description 1
- RGJCUEFHZJHTMV-UHFFFAOYSA-N [Br-].[Br-].C(C1=CC=CC=C1)(=O)C1=CC=C(C[NH+](C)C)C=C1.C=C.C(C1=CC=CC=C1)(=O)C1=CC=C(C[NH+](C)C)C=C1 Chemical compound [Br-].[Br-].C(C1=CC=CC=C1)(=O)C1=CC=C(C[NH+](C)C)C=C1.C=C.C(C1=CC=CC=C1)(=O)C1=CC=C(C[NH+](C)C)C=C1 RGJCUEFHZJHTMV-UHFFFAOYSA-N 0.000 description 1
- ITLHXEGAYQFOHJ-UHFFFAOYSA-N [diazo(phenyl)methyl]benzene Chemical compound C=1C=CC=CC=1C(=[N+]=[N-])C1=CC=CC=C1 ITLHXEGAYQFOHJ-UHFFFAOYSA-N 0.000 description 1
- 238000005299 abrasion Methods 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- FZEYVTFCMJSGMP-UHFFFAOYSA-N acridone Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3NC2=C1 FZEYVTFCMJSGMP-UHFFFAOYSA-N 0.000 description 1
- 230000001464 adherent effect Effects 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 239000000908 ammonium hydroxide Substances 0.000 description 1
- PYKYMHQGRFAEBM-UHFFFAOYSA-N anthraquinone Natural products CCC(=O)c1c(O)c2C(=O)C3C(C=CC=C3O)C(=O)c2cc1CC(=O)OC PYKYMHQGRFAEBM-UHFFFAOYSA-N 0.000 description 1
- 150000004056 anthraquinones Chemical class 0.000 description 1
- RJGDLRCDCYRQOQ-UHFFFAOYSA-N anthrone Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3CC2=C1 RJGDLRCDCYRQOQ-UHFFFAOYSA-N 0.000 description 1
- IVRMZWNICZWHMI-UHFFFAOYSA-N azide group Chemical group [N-]=[N+]=[N-] IVRMZWNICZWHMI-UHFFFAOYSA-N 0.000 description 1
- 150000001540 azides Chemical class 0.000 description 1
- 238000005452 bending Methods 0.000 description 1
- PJHUABJTDFXYRQ-UHFFFAOYSA-N benzoyl azide Chemical compound [N-]=[N+]=NC(=O)C1=CC=CC=C1 PJHUABJTDFXYRQ-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 210000000481 breast Anatomy 0.000 description 1
- 150000001721 carbon Chemical group 0.000 description 1
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 1
- JRZBPELLUMBLQU-UHFFFAOYSA-N carbonazidic acid Chemical class OC(=O)N=[N+]=[N-] JRZBPELLUMBLQU-UHFFFAOYSA-N 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 238000004113 cell culture Methods 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 238000012512 characterization method Methods 0.000 description 1
- 150000005829 chemical entities Chemical class 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 239000002299 complementary DNA Substances 0.000 description 1
- 238000004132 cross linking Methods 0.000 description 1
- 230000009849 deactivation Effects 0.000 description 1
- 239000004053 dental implant Substances 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- HLXCYTXLQJWQFG-UHFFFAOYSA-N diphenyl(2-triethoxysilylethyl)phosphane Chemical compound C=1C=CC=CC=1P(CC[Si](OCC)(OCC)OCC)C1=CC=CC=C1 HLXCYTXLQJWQFG-UHFFFAOYSA-N 0.000 description 1
- ZWJPCOALBPMBIC-UHFFFAOYSA-N diphenylketene Chemical compound C=1C=CC=CC=1C(=C=O)C1=CC=CC=C1 ZWJPCOALBPMBIC-UHFFFAOYSA-N 0.000 description 1
- MKRTXPORKIRPDG-UHFFFAOYSA-N diphenylphosphoryl azide Chemical compound C=1C=CC=CC=1P(=O)(N=[N+]=[N-])C1=CC=CC=C1 MKRTXPORKIRPDG-UHFFFAOYSA-N 0.000 description 1
- XWPWZOJBTOJEGW-UHFFFAOYSA-L disodium;benzene-1,3-disulfonate Chemical compound [Na+].[Na+].[O-]S(=O)(=O)C1=CC=CC(S([O-])(=O)=O)=C1 XWPWZOJBTOJEGW-UHFFFAOYSA-L 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 230000009189 diving Effects 0.000 description 1
- CCGKOQOJPYTBIH-UHFFFAOYSA-N ethenone Chemical compound C=C=O CCGKOQOJPYTBIH-UHFFFAOYSA-N 0.000 description 1
- HZAHPOBLARATTK-UHFFFAOYSA-N ethyl n-diazocarbamate Chemical compound CCOC(=O)N=[N+]=[N-] HZAHPOBLARATTK-UHFFFAOYSA-N 0.000 description 1
- 230000005284 excitation Effects 0.000 description 1
- 230000005281 excited state Effects 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 229910052588 hydroxylapatite Inorganic materials 0.000 description 1
- 238000005286 illumination Methods 0.000 description 1
- 238000007901 in situ hybridization Methods 0.000 description 1
- 229910010272 inorganic material Inorganic materials 0.000 description 1
- 239000011147 inorganic material Substances 0.000 description 1
- 150000002561 ketenes Chemical class 0.000 description 1
- 210000003734 kidney Anatomy 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
- 238000002493 microarray Methods 0.000 description 1
- 229920005615 natural polymer Polymers 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 238000002966 oligonucleotide array Methods 0.000 description 1
- 210000000056 organ Anatomy 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 210000003899 penis Anatomy 0.000 description 1
- XYJRXVWERLGGKC-UHFFFAOYSA-D pentacalcium;hydroxide;triphosphate Chemical compound [OH-].[Ca+2].[Ca+2].[Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O XYJRXVWERLGGKC-UHFFFAOYSA-D 0.000 description 1
- CTRLRINCMYICJO-UHFFFAOYSA-N phenyl azide Chemical compound [N-]=[N+]=NC1=CC=CC=C1 CTRLRINCMYICJO-UHFFFAOYSA-N 0.000 description 1
- UFJCUIGMJOFBRX-UHFFFAOYSA-N phenyl n-diazocarbamate Chemical compound [N-]=[N+]=NC(=O)OC1=CC=CC=C1 UFJCUIGMJOFBRX-UHFFFAOYSA-N 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 150000003009 phosphonic acids Chemical class 0.000 description 1
- XYFCBTPGUUZFHI-UHFFFAOYSA-O phosphonium Chemical compound [PH4+] XYFCBTPGUUZFHI-UHFFFAOYSA-O 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 229920002401 polyacrylamide Polymers 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 150000004053 quinones Chemical class 0.000 description 1
- 230000007420 reactivation Effects 0.000 description 1
- 230000002441 reversible effect Effects 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 150000004756 silanes Chemical class 0.000 description 1
- HBMJWWWQQXIZIP-UHFFFAOYSA-N silicon carbide Chemical compound [Si+]#[C-] HBMJWWWQQXIZIP-UHFFFAOYSA-N 0.000 description 1
- 229910010271 silicon carbide Inorganic materials 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- HQVNEWCFYHHQES-UHFFFAOYSA-N silicon nitride Chemical compound N12[Si]34N5[Si]62N3[Si]51N64 HQVNEWCFYHHQES-UHFFFAOYSA-N 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 210000005070 sphincter Anatomy 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- HSVFKFNNMLUVEY-UHFFFAOYSA-N sulfuryl diazide Chemical class [N-]=[N+]=NS(=O)(=O)N=[N+]=[N-] HSVFKFNNMLUVEY-UHFFFAOYSA-N 0.000 description 1
- 229920001059 synthetic polymer Polymers 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
- 230000007704 transition Effects 0.000 description 1
- VTHOKNTVYKTUPI-UHFFFAOYSA-N triethoxy-[3-(3-triethoxysilylpropyltetrasulfanyl)propyl]silane Chemical compound CCO[Si](OCC)(OCC)CCCSSSSCCC[Si](OCC)(OCC)OCC VTHOKNTVYKTUPI-UHFFFAOYSA-N 0.000 description 1
- PZJJKWKADRNWSW-UHFFFAOYSA-N trimethoxysilicon Chemical group CO[Si](OC)OC PZJJKWKADRNWSW-UHFFFAOYSA-N 0.000 description 1
- 229910052726 zirconium Inorganic materials 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
- A61L27/00—Materials for grafts or prostheses or for coating grafts or prostheses
- A61L27/28—Materials for coating prostheses
- A61L27/34—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
- A61L2420/00—Materials or methods for coatings medical devices
- A61L2420/08—Coatings comprising two or more layers
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/31504—Composite [nonstructural laminate]
- Y10T428/31652—Of asbestos
- Y10T428/31663—As siloxane, silicone or silane
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/31504—Composite [nonstructural laminate]
- Y10T428/31652—Of asbestos
- Y10T428/31667—Next to addition polymer from unsaturated monomers, or aldehyde or ketone condensation product
Landscapes
- Health & Medical Sciences (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Dermatology (AREA)
- Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Oral & Maxillofacial Surgery (AREA)
- Transplantation (AREA)
- Heart & Thoracic Surgery (AREA)
- Surgery (AREA)
- Vascular Medicine (AREA)
- Materials For Medical Uses (AREA)
- Paints Or Removers (AREA)
- Laminated Bodies (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US10/147,098 US6706408B2 (en) | 2002-05-16 | 2002-05-16 | Silane coating composition |
| US147098 | 2002-05-16 | ||
| PCT/US2003/009897 WO2003097117A1 (en) | 2002-05-16 | 2003-04-01 | Silane coating composition |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE60314131D1 DE60314131D1 (de) | 2007-07-12 |
| DE60314131T2 true DE60314131T2 (de) | 2008-01-31 |
Family
ID=29418953
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2003614131 Expired - Lifetime DE60314131T2 (de) | 2002-05-16 | 2003-04-01 | Silan-beschichtungszusammensetzung |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US6706408B2 (enExample) |
| EP (1) | EP1503813B1 (enExample) |
| JP (1) | JP4523405B2 (enExample) |
| AU (1) | AU2003226170A1 (enExample) |
| CA (1) | CA2486003C (enExample) |
| DE (1) | DE60314131T2 (enExample) |
| WO (1) | WO2003097117A1 (enExample) |
Families Citing this family (90)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7220276B1 (en) * | 2000-03-06 | 2007-05-22 | Surmodics, Inc. | Endovascular graft coatings |
| US7297553B2 (en) | 2002-05-28 | 2007-11-20 | Nanosphere, Inc. | Method for attachment of silylated molecules to glass surfaces |
| AU2002322458A1 (en) * | 2001-07-13 | 2003-01-29 | Nanosphere, Inc. | Method for immobilizing molecules onto surfaces |
| US7348055B2 (en) * | 2001-12-21 | 2008-03-25 | Surmodics, Inc. | Reagent and method for providing coatings on surfaces |
| DE10223310A1 (de) * | 2002-05-24 | 2003-12-11 | Biotronik Mess & Therapieg | Verfahren zum Beschichten von Implantaten mit einer Polysaccharid-Lage |
| US7163321B2 (en) * | 2002-07-25 | 2007-01-16 | Steven Contarino | Emergency vehicle grille |
| US7285363B2 (en) * | 2002-11-08 | 2007-10-23 | The University Of Connecticut | Photoactivators, methods of use, and the articles derived therefrom |
| US7063884B2 (en) * | 2003-02-26 | 2006-06-20 | Advanced Cardiovascular Systems, Inc. | Stent coating |
| US6926919B1 (en) * | 2003-02-26 | 2005-08-09 | Advanced Cardiovascular Systems, Inc. | Method for fabricating a coating for a medical device |
| US7563483B2 (en) * | 2003-02-26 | 2009-07-21 | Advanced Cardiovascular Systems Inc. | Methods for fabricating a coating for implantable medical devices |
| IES20030294A2 (en) * | 2003-04-17 | 2004-10-20 | Medtronic Vascular Connaught | Coating for biomedical devices |
| WO2005037338A1 (en) * | 2003-10-14 | 2005-04-28 | Cook Incorporated | Hydrophilic coated medical device |
| JP4401153B2 (ja) * | 2003-12-05 | 2010-01-20 | 大日本印刷株式会社 | パターニング用基板および細胞培養基板 |
| EP1735024A1 (en) * | 2004-03-26 | 2006-12-27 | SurModics, Inc. | Process and systems for biocompatible surfaces |
| WO2005115490A2 (en) * | 2004-05-25 | 2005-12-08 | Surmodics, Inc. | Natural biodegradable polysaccharide coatings for meical articles |
| CA2585215A1 (en) * | 2004-10-28 | 2006-05-11 | Surmodics, Inc. | Pro-fibrotic coatings comprising collagen for medical implants |
| US20060093647A1 (en) * | 2004-10-29 | 2006-05-04 | Villafana Manuel A | Multiple layer coating composition |
| JP2008522670A (ja) * | 2004-12-06 | 2008-07-03 | サーモディクス，インコーポレイティド | 多機能医療物品 |
| US20060147847A1 (en) * | 2004-12-30 | 2006-07-06 | Guire Patrick E | Antimicrobial compositions and methods |
| JP5155146B2 (ja) * | 2005-03-15 | 2013-02-27 | サーモディクス，インコーポレイティド | 挿入可能な医療器具用の柔軟性ポリマー被膜 |
| US8002730B2 (en) | 2005-04-29 | 2011-08-23 | Medtronic, Inc. | Anti-thrombogenic venous shunt system and method |
| WO2006130776A2 (en) * | 2005-06-02 | 2006-12-07 | Surmodics, Inc. | Hydrophilic polymeric coatings for medical articles |
| US7772393B2 (en) * | 2005-06-13 | 2010-08-10 | Innovative Surface Technologies, Inc. | Photochemical crosslinkers for polymer coatings and substrate tie-layer |
| JP4992070B2 (ja) * | 2005-07-29 | 2012-08-08 | 国立大学法人 岡山大学 | 生理活性物質固定化チタン材及びその製造方法 |
| US20070141365A1 (en) * | 2005-08-26 | 2007-06-21 | Jelle Bruce M | Silane Coating Compositions, Coating Systems, and Methods |
| US20070054127A1 (en) * | 2005-08-26 | 2007-03-08 | Hergenrother Robert W | Silane coating compositions, coating systems, and methods |
| US20070160743A1 (en) * | 2006-01-09 | 2007-07-12 | Babitt John L | Method for coating biocompatible material on a substrate |
| US20080082036A1 (en) | 2006-04-25 | 2008-04-03 | Medtronic, Inc. | Cerebrospinal fluid shunt having long term anti-occlusion agent delivery |
| EP2020007A4 (en) * | 2006-04-27 | 2011-01-26 | St Jude Medical | COATED PIPES AND MANUFACTURING METHOD THEREFOR |
| EP2160484A2 (en) | 2007-06-22 | 2010-03-10 | Innovative Surface Technologies, Inc. | Nanofibers containing latent reactive groups |
| EP2171135A2 (en) | 2007-06-22 | 2010-04-07 | Innovative Surface Technologies, Inc. | Stimuli responsive nanofibers |
| US20100272693A1 (en) * | 2007-11-30 | 2010-10-28 | Eunah Lee | Bone scaffolds, injectable bone repair materials and methods for bone repair |
| EP2242520A2 (en) * | 2008-01-14 | 2010-10-27 | SurModics, Inc. | Devices and methods for elution of nucleic acid delivery complexes |
| FR2928084A1 (fr) * | 2008-02-28 | 2009-09-04 | Cie Euro Etude Rech Paroscopie | Dispositif implantable et procede de fabrication correspondant |
| US8883710B2 (en) * | 2008-05-16 | 2014-11-11 | The Procter & Gamble Company | Compositions and methods incorporating photocatalysts |
| US11786036B2 (en) | 2008-06-27 | 2023-10-17 | Ssw Advanced Technologies, Llc | Spill containing refrigerator shelf assembly |
| US8286561B2 (en) | 2008-06-27 | 2012-10-16 | Ssw Holding Company, Inc. | Spill containing refrigerator shelf assembly |
| CA2734410A1 (en) * | 2008-09-05 | 2010-03-11 | Innovative Surface Technologies, Inc. | Photoactivatable crosslinker compositions for surface modification |
| US8049061B2 (en) | 2008-09-25 | 2011-11-01 | Abbott Cardiovascular Systems, Inc. | Expandable member formed of a fibrous matrix having hydrogel polymer for intraluminal drug delivery |
| US8226603B2 (en) * | 2008-09-25 | 2012-07-24 | Abbott Cardiovascular Systems Inc. | Expandable member having a covering formed of a fibrous matrix for intraluminal drug delivery |
| US8076529B2 (en) * | 2008-09-26 | 2011-12-13 | Abbott Cardiovascular Systems, Inc. | Expandable member formed of a fibrous matrix for intraluminal drug delivery |
| CA2739903C (en) | 2008-10-07 | 2016-12-06 | Ross Technology Corporation | Highly durable superhydrophobic, oleophobic and anti-icing coatings and methods and compositions for their preparation |
| TW201023220A (en) | 2008-12-01 | 2010-06-16 | Sanyo Electric Co | Method of manufacturing solid electrolytic capacitor |
| US8691983B2 (en) * | 2009-03-03 | 2014-04-08 | Innovative Surface Technologies, Inc. | Brush polymer coating by in situ polymerization from photoreactive surface |
| US8163357B2 (en) * | 2009-03-26 | 2012-04-24 | Signet Armorlite, Inc. | Scratch-resistant coatings with improved adhesion to inorganic thin film coatings |
| DE102009002153A1 (de) * | 2009-04-02 | 2010-10-21 | Biotronik Vi Patent Ag | Implantat aus einem biokorrodierbaren metallischen Werkstoff mit einer nanopartikel-haltigen Silanbeschichtung und dazugehöriges Herstellungsverfahren |
| JP2012525479A (ja) * | 2009-05-01 | 2012-10-22 | ザ プロクター アンド ギャンブル カンパニー | 光触媒導入組成物及び光触媒導入方法 |
| US20100285085A1 (en) * | 2009-05-07 | 2010-11-11 | Abbott Cardiovascular Systems Inc. | Balloon coating with drug transfer control via coating thickness |
| US8802121B2 (en) * | 2009-06-02 | 2014-08-12 | Surmodics, Inc. | Silane-functionalized hydrophobic α(1→4)glucopyranose polymers and polymeric matrices for implantation or injection |
| WO2011041517A1 (en) * | 2009-09-30 | 2011-04-07 | Surmodics, Inc. | Hydrophobic polysaccharides with silyl ether linkages having enhanced degradation and medical articles made therefrom |
| WO2011056742A1 (en) | 2009-11-04 | 2011-05-12 | Ssw Holding Company, Inc. | Cooking appliance surfaces having spill containment pattern and methods of making the same |
| US8287890B2 (en) * | 2009-12-15 | 2012-10-16 | C.R. Bard, Inc. | Hydrophilic coating |
| US8568760B2 (en) * | 2009-12-30 | 2013-10-29 | Surmodics, Inc. | Hydrophobic polysaccharides with pendent groups having terminal reactive functionalities and medical uses thereof |
| US8475843B2 (en) * | 2009-12-31 | 2013-07-02 | Surmodics, Inc. | Silyl ether-modified hydrophilic polymers and uses for medical articles |
| JP5858441B2 (ja) | 2010-03-15 | 2016-02-10 | ロス テクノロジー コーポレーション．Ｒｏｓｓ Ｔｅｃｈｎｏｌｏｇｙ Ｃｏｒｐｏｒａｔｉｏｎ | プランジャーおよび疎水性表面を得るための方法 |
| WO2011119536A1 (en) | 2010-03-22 | 2011-09-29 | Abbott Cardiovascular Systems Inc. | Stent delivery system having a fibrous matrix covering with improved stent retention |
| EP2552927B1 (en) | 2010-03-30 | 2019-03-13 | SurModics, Inc. | Degradable photo-crosslinkers |
| JP5907957B2 (ja) * | 2010-06-16 | 2016-04-26 | ディーエスエム アイピー アセッツ ビー．ブイ． | 親水性コーティングを製造するためのコーティング配合物 |
| US20110311601A1 (en) * | 2010-06-22 | 2011-12-22 | Michael Kleine | Antimicrobial medical devices |
| CA2802229C (en) | 2010-06-29 | 2019-01-29 | Surmodics, Inc. | Fluorinated polymers and lubricious coatings |
| JP5544600B2 (ja) * | 2010-06-30 | 2014-07-09 | 独立行政法人科学技術振興機構 | 生体適合性ポリマー基板 |
| US10315987B2 (en) | 2010-12-13 | 2019-06-11 | Surmodics, Inc. | Photo-crosslinker |
| US8901092B2 (en) | 2010-12-29 | 2014-12-02 | Surmodics, Inc. | Functionalized polysaccharides for active agent delivery |
| CN103476898A (zh) | 2011-02-21 | 2013-12-25 | 罗斯科技公司 | 具有低voc粘合剂体系的超疏水性和疏油性涂层 |
| DE102011085428A1 (de) | 2011-10-28 | 2013-05-02 | Schott Ag | Einlegeboden |
| US9681939B2 (en) * | 2011-11-18 | 2017-06-20 | Cook Medical Technologies Llc | Silane bonded medical devices and method of making same |
| EP2791255B1 (en) | 2011-12-15 | 2017-11-01 | Ross Technology Corporation | Composition and coating for superhydrophobic performance |
| US8956682B2 (en) | 2012-04-02 | 2015-02-17 | Surmodics, Inc. | Hydrophilic polymeric coatings for medical articles with visualization moiety |
| AU2013281220B2 (en) | 2012-06-25 | 2017-03-16 | Ross Technology Corporation | Elastomeric coatings having hydrophobic and/or oleophobic properties |
| CN105102677B (zh) * | 2013-10-18 | 2018-09-28 | 住友橡胶工业株式会社 | 表面改性金属及用于对金属表面进行改性的方法 |
| JP6157429B2 (ja) * | 2013-10-21 | 2017-07-05 | 住友ゴム工業株式会社 | 潤滑性、低タンパク質吸着性および／または低細胞吸着性を有する金属医療用具及びその製造方法 |
| JP6154370B2 (ja) * | 2014-12-26 | 2017-06-28 | 住友ゴム工業株式会社 | 表面改質金属及び金属表面の改質方法 |
| JP6554984B2 (ja) * | 2015-08-03 | 2019-08-07 | 住友ゴム工業株式会社 | 表面改質金属及び金属表面の改質方法 |
| JP6753041B2 (ja) | 2015-08-27 | 2020-09-09 | 住友ゴム工業株式会社 | 表面改質金属及び金属表面の改質方法 |
| JP6610200B2 (ja) * | 2015-11-26 | 2019-11-27 | 住友ゴム工業株式会社 | 金属医療用具及びその製造方法 |
| CA3046087A1 (en) | 2016-12-09 | 2018-06-14 | Zenflow, Inc. | Systems, devices, and methods for the accurate deployment of an implant in the prostatic urethra |
| JP2018153441A (ja) * | 2017-03-17 | 2018-10-04 | 株式会社日本触媒 | 人工関節用材料 |
| US11709156B2 (en) | 2017-09-18 | 2023-07-25 | Waters Technologies Corporation | Use of vapor deposition coated flow paths for improved analytical analysis |
| US12180581B2 (en) | 2017-09-18 | 2024-12-31 | Waters Technologies Corporation | Use of vapor deposition coated flow paths for improved chromatography of metal interacting analytes |
| US12181452B2 (en) | 2017-09-18 | 2024-12-31 | Waters Technologies Corporation | Use of vapor deposition coated flow paths for improved chromatography of metal interacting analytes |
| US11709155B2 (en) | 2017-09-18 | 2023-07-25 | Waters Technologies Corporation | Use of vapor deposition coated flow paths for improved chromatography of metal interacting analytes |
| CN112789323B (zh) * | 2018-10-02 | 2024-02-02 | 株式会社力森诺科 | 树脂组合物、固化物及半导体器件 |
| US12121829B2 (en) | 2019-02-27 | 2024-10-22 | Waters Technologies Corporation | Chromatographic seal and coated flow paths for minimizing analyte adsorption |
| JP7767265B2 (ja) | 2019-07-26 | 2025-11-11 | マイクロベンション インコーポレイテッド | コーティング |
| AU2020387396B2 (en) | 2019-11-19 | 2025-10-30 | Zenflow, Inc. | Systems, devices, and methods for the accurate deployment and imaging of an implant in the prostatic urethra |
| US11918936B2 (en) | 2020-01-17 | 2024-03-05 | Waters Technologies Corporation | Performance and dynamic range for oligonucleotide bioanalysis through reduction of non specific binding |
| US11827862B2 (en) * | 2020-08-07 | 2023-11-28 | Microvention, Inc. | Durable surface coatings |
| US12352734B2 (en) | 2020-09-24 | 2025-07-08 | Waters Technologies Corporation | Chromatographic hardware improvements for separation of reactive molecules |
| US12496612B2 (en) | 2021-01-08 | 2025-12-16 | Surmodics, Inc. | Coating application system and methods for coating rotatable medical devices |
| US20240279564A1 (en) * | 2023-02-14 | 2024-08-22 | Actnano, Inc. | Compositions for reducing friction or stiction of a surface, methods and articles comprising the same |
Family Cites Families (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5295978A (en) * | 1990-12-28 | 1994-03-22 | Union Carbide Chemicals & Plastics Technology Corporation | Biocompatible hydrophilic complexes and process for preparation and use |
| US5414075A (en) | 1992-11-06 | 1995-05-09 | Bsi Corporation | Restrained multifunctional reagent for surface modification |
| DK0604103T3 (da) * | 1992-12-15 | 1999-09-27 | Johnson & Johnson Consumer | Hydrogellaminat, forbindinger og materialer samt fremgangsmåder til fremstilling deraf |
| US5749837A (en) | 1993-05-11 | 1998-05-12 | Target Therapeutics, Inc. | Enhanced lubricity guidewire |
| US5443455A (en) * | 1993-07-27 | 1995-08-22 | Target Therapeutics, Inc. | Guidewire and method of pretreating metal surfaces for subsequent polymer coating |
| US5714360A (en) | 1995-11-03 | 1998-02-03 | Bsi Corporation | Photoactivatable water soluble cross-linking agents containing an onium group |
| US5962161A (en) * | 1997-01-14 | 1999-10-05 | Daramic, Inc. | Recombinant battery separator |
| AU3360897A (en) | 1997-07-04 | 1999-01-25 | Universiteit Utrecht | A metal particle, its preparation and use, and a material or device comprising the metal particle |
| US6121027A (en) | 1997-08-15 | 2000-09-19 | Surmodics, Inc. | Polybifunctional reagent having a polymeric backbone and photoreactive moieties and bioactive groups |
| US6254634B1 (en) | 1998-06-10 | 2001-07-03 | Surmodics, Inc. | Coating compositions |
| US6372813B1 (en) | 1999-06-25 | 2002-04-16 | Motorola | Methods and compositions for attachment of biomolecules to solid supports, hydrogels, and hydrogel arrays |
| US6278018B1 (en) | 1999-12-14 | 2001-08-21 | Surmodics, Inc. | Surface coating agents |
| EP1309360B1 (en) | 2000-08-15 | 2006-04-19 | SurModics, Inc. | Medicament incorporation matrix |
-
2002
- 2002-05-16 US US10/147,098 patent/US6706408B2/en not_active Expired - Lifetime
-
2003
- 2003-04-01 AU AU2003226170A patent/AU2003226170A1/en not_active Abandoned
- 2003-04-01 WO PCT/US2003/009897 patent/WO2003097117A1/en not_active Ceased
- 2003-04-01 CA CA 2486003 patent/CA2486003C/en not_active Expired - Lifetime
- 2003-04-01 JP JP2004505112A patent/JP4523405B2/ja not_active Expired - Lifetime
- 2003-04-01 EP EP20030752984 patent/EP1503813B1/en not_active Expired - Lifetime
- 2003-04-01 DE DE2003614131 patent/DE60314131T2/de not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| CA2486003C (en) | 2013-01-22 |
| US20030215649A1 (en) | 2003-11-20 |
| JP2005528253A (ja) | 2005-09-22 |
| WO2003097117A1 (en) | 2003-11-27 |
| JP4523405B2 (ja) | 2010-08-11 |
| EP1503813B1 (en) | 2007-05-30 |
| DE60314131D1 (de) | 2007-07-12 |
| CA2486003A1 (en) | 2003-11-27 |
| US6706408B2 (en) | 2004-03-16 |
| AU2003226170A1 (en) | 2003-12-02 |
| EP1503813A1 (en) | 2005-02-09 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE60314131T2 (de) | Silan-beschichtungszusammensetzung | |
| US10266620B2 (en) | Coating agents and coated articles | |
| JP6408056B2 (ja) | 微粒子が少ない、医療装置用潤滑性コーティング | |
| JP7224409B2 (ja) | 医療デバイス用潤滑コーティング | |
| EP1858438B1 (en) | Compliant polymeric coatings for insertable medical articles | |
| US20030165613A1 (en) | Reagent and method for providing coatings on surfaces | |
| EP3397296B1 (en) | Lubricious coatings with surface salt groups |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8364 | No opposition during term of opposition |