JP2020515699A5 - - Google Patents
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- JP2020515699A5 JP2020515699A5 JP2019554393A JP2019554393A JP2020515699A5 JP 2020515699 A5 JP2020515699 A5 JP 2020515699A5 JP 2019554393 A JP2019554393 A JP 2019554393A JP 2019554393 A JP2019554393 A JP 2019554393A JP 2020515699 A5 JP2020515699 A5 JP 2020515699A5
- Authority
- JP
- Japan
- Prior art keywords
- silver
- coating
- acid
- optionally
- group
- 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.)
- Pending
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- 239000011248 coating agent Substances 0.000 claims description 77
- 238000000576 coating method Methods 0.000 claims description 77
- 238000000034 method Methods 0.000 claims description 65
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 64
- 239000000178 monomer Substances 0.000 claims description 63
- 230000007935 neutral effect Effects 0.000 claims description 35
- 229920000642 polymer Polymers 0.000 claims description 34
- -1 aminoglycoside Substances 0.000 claims description 22
- 239000008199 coating composition Substances 0.000 claims description 20
- 239000000203 mixture Substances 0.000 claims description 18
- 239000003242 anti bacterial agent Substances 0.000 claims description 17
- 239000004332 silver Substances 0.000 claims description 15
- 229910052709 silver Inorganic materials 0.000 claims description 15
- 239000000243 solution Substances 0.000 claims description 14
- 230000009477 glass transition Effects 0.000 claims description 13
- 238000006116 polymerization reaction Methods 0.000 claims description 12
- 239000003929 acidic solution Substances 0.000 claims description 10
- 239000003637 basic solution Substances 0.000 claims description 9
- 229920001519 homopolymer Polymers 0.000 claims description 9
- JKFYKCYQEWQPTM-UHFFFAOYSA-N 2-azaniumyl-2-(4-fluorophenyl)acetate Chemical compound OC(=O)C(N)C1=CC=C(F)C=C1 JKFYKCYQEWQPTM-UHFFFAOYSA-N 0.000 claims description 8
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 claims description 8
- 229910021612 Silver iodide Inorganic materials 0.000 claims description 8
- 229940045105 silver iodide Drugs 0.000 claims description 8
- SQGYOTSLMSWVJD-UHFFFAOYSA-N silver(1+) nitrate Chemical compound [Ag+].[O-]N(=O)=O SQGYOTSLMSWVJD-UHFFFAOYSA-N 0.000 claims description 8
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 claims description 7
- 230000000844 anti-bacterial effect Effects 0.000 claims description 7
- 230000002785 anti-thrombosis Effects 0.000 claims description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 6
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 claims description 6
- 229920001577 copolymer Polymers 0.000 claims description 6
- 239000003999 initiator Substances 0.000 claims description 6
- 239000002253 acid Substances 0.000 claims description 5
- ZXSQEZNORDWBGZ-UHFFFAOYSA-N 1,3-dihydropyrrolo[2,3-b]pyridin-2-one Chemical compound C1=CN=C2NC(=O)CC2=C1 ZXSQEZNORDWBGZ-UHFFFAOYSA-N 0.000 claims description 4
- VAZJLPXFVQHDFB-UHFFFAOYSA-N 1-(diaminomethylidene)-2-hexylguanidine Polymers CCCCCCN=C(N)N=C(N)N VAZJLPXFVQHDFB-UHFFFAOYSA-N 0.000 claims description 4
- JAHNSTQSQJOJLO-UHFFFAOYSA-N 2-(3-fluorophenyl)-1h-imidazole Chemical compound FC1=CC=CC(C=2NC=CN=2)=C1 JAHNSTQSQJOJLO-UHFFFAOYSA-N 0.000 claims description 4
- NOOYFQLPKUQDNE-UHFFFAOYSA-N 2-(bromomethyl)prop-2-enoic acid Chemical compound OC(=O)C(=C)CBr NOOYFQLPKUQDNE-UHFFFAOYSA-N 0.000 claims description 4
- VLSRKCIBHNJFHA-UHFFFAOYSA-N 2-(trifluoromethyl)prop-2-enoic acid Chemical compound OC(=O)C(=C)C(F)(F)F VLSRKCIBHNJFHA-UHFFFAOYSA-N 0.000 claims description 4
- HMENQNSSJFLQOP-UHFFFAOYSA-N 2-bromoprop-2-enoic acid Chemical compound OC(=O)C(Br)=C HMENQNSSJFLQOP-UHFFFAOYSA-N 0.000 claims description 4
- WROUWQQRXUBECT-UHFFFAOYSA-N 2-ethylacrylic acid Chemical compound CCC(=C)C(O)=O WROUWQQRXUBECT-UHFFFAOYSA-N 0.000 claims description 4
- HEBDGRTWECSNNT-UHFFFAOYSA-N 2-methylidenepentanoic acid Chemical compound CCCC(=C)C(O)=O HEBDGRTWECSNNT-UHFFFAOYSA-N 0.000 claims description 4
- CYUZOYPRAQASLN-UHFFFAOYSA-N 3-prop-2-enoyloxypropanoic acid Chemical compound OC(=O)CCOC(=O)C=C CYUZOYPRAQASLN-UHFFFAOYSA-N 0.000 claims description 4
- IRQWEODKXLDORP-UHFFFAOYSA-N 4-ethenylbenzoic acid Chemical compound OC(=O)C1=CC=C(C=C)C=C1 IRQWEODKXLDORP-UHFFFAOYSA-N 0.000 claims description 4
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 claims description 4
- GHXZTYHSJHQHIJ-UHFFFAOYSA-N Chlorhexidine Chemical compound C=1C=C(Cl)C=CC=1NC(N)=NC(N)=NCCCCCCN=C(N)N=C(N)NC1=CC=C(Cl)C=C1 GHXZTYHSJHQHIJ-UHFFFAOYSA-N 0.000 claims description 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 4
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 4
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 claims description 4
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims description 4
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 claims description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 4
- 229920002413 Polyhexanide Polymers 0.000 claims description 4
- 229910021607 Silver chloride Inorganic materials 0.000 claims description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims description 4
- 239000004098 Tetracycline Substances 0.000 claims description 4
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 4
- NIXOWILDQLNWCW-UHFFFAOYSA-M acrylate group Chemical group C(C=C)(=O)[O-] NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 4
- 229940126575 aminoglycoside Drugs 0.000 claims description 4
- 239000003146 anticoagulant agent Substances 0.000 claims description 4
- 229960000686 benzalkonium chloride Drugs 0.000 claims description 4
- 229960001950 benzethonium chloride Drugs 0.000 claims description 4
- UREZNYTWGJKWBI-UHFFFAOYSA-M benzethonium chloride Chemical compound [Cl-].C1=CC(C(C)(C)CC(C)(C)C)=CC=C1OCCOCC[N+](C)(C)CC1=CC=CC=C1 UREZNYTWGJKWBI-UHFFFAOYSA-M 0.000 claims description 4
- CADWTSSKOVRVJC-UHFFFAOYSA-N benzyl(dimethyl)azanium;chloride Chemical compound [Cl-].C[NH+](C)CC1=CC=CC=C1 CADWTSSKOVRVJC-UHFFFAOYSA-N 0.000 claims description 4
- 229960003260 chlorhexidine Drugs 0.000 claims description 4
- 239000000460 chlorine Substances 0.000 claims description 4
- 229910052801 chlorine Inorganic materials 0.000 claims description 4
- 239000010949 copper Substances 0.000 claims description 4
- 229910052802 copper Inorganic materials 0.000 claims description 4
- 229940124307 fluoroquinolone Drugs 0.000 claims description 4
- 239000003120 macrolide antibiotic agent Substances 0.000 claims description 4
- FQPSGWSUVKBHSU-UHFFFAOYSA-N methacrylamide Chemical compound CC(=C)C(N)=O FQPSGWSUVKBHSU-UHFFFAOYSA-N 0.000 claims description 4
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims description 4
- LVHBHZANLOWSRM-UHFFFAOYSA-N methylenebutanedioic acid Natural products OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 claims description 4
- ZVXNYZWXUADSRV-UHFFFAOYSA-N octenidine Chemical compound C1=CC(=NCCCCCCCC)C=CN1CCCCCCCCCCN1C=CC(=NCCCCCCCC)C=C1 ZVXNYZWXUADSRV-UHFFFAOYSA-N 0.000 claims description 4
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 claims description 4
- CQLFBEKRDQMJLZ-UHFFFAOYSA-M silver acetate Chemical compound [Ag+].CC([O-])=O CQLFBEKRDQMJLZ-UHFFFAOYSA-M 0.000 claims description 4
- 229940071536 silver acetate Drugs 0.000 claims description 4
- 229910001958 silver carbonate Inorganic materials 0.000 claims description 4
- LKZMBDSASOBTPN-UHFFFAOYSA-L silver carbonate Substances [Ag].[O-]C([O-])=O LKZMBDSASOBTPN-UHFFFAOYSA-L 0.000 claims description 4
- 229940071575 silver citrate Drugs 0.000 claims description 4
- HKZLPVFGJNLROG-UHFFFAOYSA-M silver monochloride Chemical compound [Cl-].[Ag+] HKZLPVFGJNLROG-UHFFFAOYSA-M 0.000 claims description 4
- 229910001961 silver nitrate Inorganic materials 0.000 claims description 4
- 229960001516 silver nitrate Drugs 0.000 claims description 4
- FJOLTQXXWSRAIX-UHFFFAOYSA-K silver phosphate Chemical group [Ag+].[Ag+].[Ag+].[O-]P([O-])([O-])=O FJOLTQXXWSRAIX-UHFFFAOYSA-K 0.000 claims description 4
- 229940019931 silver phosphate Drugs 0.000 claims description 4
- 229910000161 silver phosphate Inorganic materials 0.000 claims description 4
- LMEWRZSPCQHBOB-UHFFFAOYSA-M silver;2-hydroxypropanoate Chemical compound [Ag+].CC(O)C([O-])=O LMEWRZSPCQHBOB-UHFFFAOYSA-M 0.000 claims description 4
- CLDWGXZGFUNWKB-UHFFFAOYSA-M silver;benzoate Chemical compound [Ag+].[O-]C(=O)C1=CC=CC=C1 CLDWGXZGFUNWKB-UHFFFAOYSA-M 0.000 claims description 4
- MNMYRUHURLPFQW-UHFFFAOYSA-M silver;dodecanoate Chemical compound [Ag+].CCCCCCCCCCCC([O-])=O MNMYRUHURLPFQW-UHFFFAOYSA-M 0.000 claims description 4
- LTYHQUJGIQUHMS-UHFFFAOYSA-M silver;hexadecanoate Chemical compound [Ag+].CCCCCCCCCCCCCCCC([O-])=O LTYHQUJGIQUHMS-UHFFFAOYSA-M 0.000 claims description 4
- 235000011121 sodium hydroxide Nutrition 0.000 claims description 4
- SONHXMAHPHADTF-UHFFFAOYSA-M sodium;2-methylprop-2-enoate Chemical compound [Na+].CC(=C)C([O-])=O SONHXMAHPHADTF-UHFFFAOYSA-M 0.000 claims description 4
- GGCZERPQGJTIQP-UHFFFAOYSA-N sodium;9,10-dioxoanthracene-2-sulfonic acid Chemical compound [Na+].C1=CC=C2C(=O)C3=CC(S(=O)(=O)O)=CC=C3C(=O)C2=C1 GGCZERPQGJTIQP-UHFFFAOYSA-N 0.000 claims description 4
- 229960002180 tetracycline Drugs 0.000 claims description 4
- 229930101283 tetracycline Natural products 0.000 claims description 4
- 235000019364 tetracycline Nutrition 0.000 claims description 4
- 150000003522 tetracyclines Chemical class 0.000 claims description 4
- QUTYHQJYVDNJJA-UHFFFAOYSA-K trisilver;2-hydroxypropane-1,2,3-tricarboxylate Chemical compound [Ag+].[Ag+].[Ag+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O QUTYHQJYVDNJJA-UHFFFAOYSA-K 0.000 claims description 4
- 239000011701 zinc Substances 0.000 claims description 4
- 229910052725 zinc Inorganic materials 0.000 claims description 4
- 239000004952 Polyamide Substances 0.000 claims description 3
- 229920002396 Polyurea Polymers 0.000 claims description 3
- 230000004071 biological effect Effects 0.000 claims description 3
- 230000032798 delamination Effects 0.000 claims description 3
- 239000004053 dental implant Substances 0.000 claims description 3
- 210000003709 heart valve Anatomy 0.000 claims description 3
- 239000007943 implant Substances 0.000 claims description 3
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical class CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 claims description 3
- 238000012423 maintenance Methods 0.000 claims description 3
- 239000000463 material Substances 0.000 claims description 3
- 244000005700 microbiome Species 0.000 claims description 3
- 229920002492 poly(sulfone) Polymers 0.000 claims description 3
- 229920002647 polyamide Polymers 0.000 claims description 3
- 229920000515 polycarbonate Polymers 0.000 claims description 3
- 239000004417 polycarbonate Substances 0.000 claims description 3
- 229920000728 polyester Polymers 0.000 claims description 3
- 229920000570 polyether Polymers 0.000 claims description 3
- 229920001296 polysiloxane Polymers 0.000 claims description 3
- 229920001343 polytetrafluoroethylene Polymers 0.000 claims description 3
- 229920002635 polyurethane Polymers 0.000 claims description 3
- 239000004814 polyurethane Substances 0.000 claims description 3
- 238000001356 surgical procedure Methods 0.000 claims description 3
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 3
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 claims description 2
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 claims description 2
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims description 2
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 claims description 2
- 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 claims description 2
- 239000004721 Polyphenylene oxide Substances 0.000 claims description 2
- 235000000126 Styrax benzoin Nutrition 0.000 claims description 2
- 244000028419 Styrax benzoin Species 0.000 claims description 2
- LSNNMFCWUKXFEE-UHFFFAOYSA-N Sulfurous acid Chemical compound OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 claims description 2
- 235000008411 Sumatra benzointree Nutrition 0.000 claims description 2
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 claims description 2
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims description 2
- 239000000908 ammonium hydroxide Substances 0.000 claims description 2
- 239000007864 aqueous solution Substances 0.000 claims description 2
- 239000002585 base Substances 0.000 claims description 2
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 claims description 2
- 239000012965 benzophenone Substances 0.000 claims description 2
- 229910021538 borax Inorganic materials 0.000 claims description 2
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 claims description 2
- 239000000920 calcium hydroxide Substances 0.000 claims description 2
- 229910001861 calcium hydroxide Inorganic materials 0.000 claims description 2
- 235000015165 citric acid Nutrition 0.000 claims description 2
- AJFXNBUVIBKWBT-UHFFFAOYSA-N disodium;boric acid;hydrogen borate Chemical compound [Na+].[Na+].OB(O)O.OB(O)O.OB(O)O.OB([O-])[O-] AJFXNBUVIBKWBT-UHFFFAOYSA-N 0.000 claims description 2
- 235000019253 formic acid Nutrition 0.000 claims description 2
- 235000019382 gum benzoic Nutrition 0.000 claims description 2
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 claims description 2
- 150000004679 hydroxides Chemical class 0.000 claims description 2
- QWPPOHNGKGFGJK-UHFFFAOYSA-N hypochlorous acid Chemical compound ClO QWPPOHNGKGFGJK-UHFFFAOYSA-N 0.000 claims description 2
- 235000014655 lactic acid Nutrition 0.000 claims description 2
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 claims description 2
- 150000002976 peresters Chemical class 0.000 claims description 2
- OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical compound OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 claims description 2
- 239000004810 polytetrafluoroethylene Substances 0.000 claims description 2
- 229960004889 salicylic acid Drugs 0.000 claims description 2
- 239000011734 sodium Substances 0.000 claims description 2
- 229910052708 sodium Inorganic materials 0.000 claims description 2
- WBHQBSYUUJJSRZ-UHFFFAOYSA-M sodium bisulfate Chemical compound [Na+].OS([O-])(=O)=O WBHQBSYUUJJSRZ-UHFFFAOYSA-M 0.000 claims description 2
- 229910000342 sodium bisulfate Inorganic materials 0.000 claims description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 claims description 2
- 235000017550 sodium carbonate Nutrition 0.000 claims description 2
- 235000010339 sodium tetraborate Nutrition 0.000 claims description 2
- 239000011975 tartaric acid Substances 0.000 claims description 2
- 235000002906 tartaric acid Nutrition 0.000 claims description 2
- GJBRNHKUVLOCEB-UHFFFAOYSA-N tert-butyl benzenecarboperoxoate Chemical compound CC(C)(C)OOC(=O)C1=CC=CC=C1 GJBRNHKUVLOCEB-UHFFFAOYSA-N 0.000 claims description 2
- YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 claims description 2
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 claims description 2
- 150000007513 acids Chemical class 0.000 claims 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 1
- 229910000043 hydrogen iodide Inorganic materials 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 239000011859 microparticle Substances 0.000 claims 1
- 150000002826 nitrites Chemical class 0.000 claims 1
- 229960003600 silver sulfadiazine Drugs 0.000 claims 1
- UEJSSZHHYBHCEL-UHFFFAOYSA-N silver(1+) sulfadiazinate Chemical compound [Ag+].C1=CC(N)=CC=C1S(=O)(=O)[N-]C1=NC=CC=N1 UEJSSZHHYBHCEL-UHFFFAOYSA-N 0.000 claims 1
- 125000003118 aryl group Chemical group 0.000 description 12
- 125000002837 carbocyclic group Chemical group 0.000 description 12
- 125000001072 heteroaryl group Chemical group 0.000 description 12
- 125000005842 heteroatom Chemical group 0.000 description 12
- 125000000623 heterocyclic group Chemical group 0.000 description 12
- 125000001183 hydrocarbyl group Chemical group 0.000 description 12
- 150000001875 compounds Chemical class 0.000 description 6
- 150000004820 halides Chemical class 0.000 description 6
- 150000004677 hydrates Chemical class 0.000 description 6
- 230000003287 optical effect Effects 0.000 description 6
- 239000012453 solvate Substances 0.000 description 6
- 239000000126 substance Substances 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- ODHCTXKNWHHXJC-VKHMYHEASA-N 5-oxo-L-proline Chemical compound OC(=O)[C@@H]1CCC(=O)N1 ODHCTXKNWHHXJC-VKHMYHEASA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 2
- 230000001678 irradiating effect Effects 0.000 description 2
- 239000004611 light stabiliser Substances 0.000 description 2
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 2
- 229940079889 pyrrolidonecarboxylic acid Drugs 0.000 description 2
- 239000001632 sodium acetate Substances 0.000 description 2
- 235000017281 sodium acetate Nutrition 0.000 description 2
- IOVCWXUNBOPUCH-UHFFFAOYSA-M Nitrite anion Chemical compound [O-]N=O IOVCWXUNBOPUCH-UHFFFAOYSA-M 0.000 description 1
- 238000007605 air drying Methods 0.000 description 1
- 230000005587 bubbling Effects 0.000 description 1
- 239000008367 deionised water Substances 0.000 description 1
- 229910021641 deionized water Inorganic materials 0.000 description 1
- 230000009975 flexible effect Effects 0.000 description 1
- 229940071870 hydroiodic acid Drugs 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 229920000058 polyacrylate Polymers 0.000 description 1
- 230000001954 sterilising effect Effects 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201762478187P | 2017-03-29 | 2017-03-29 | |
| US62/478,187 | 2017-03-29 | ||
| PCT/CA2018/050376 WO2018176138A1 (en) | 2017-03-29 | 2018-03-28 | Coating compositions, polymeric coatings, and methods |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2020515699A JP2020515699A (ja) | 2020-05-28 |
| JP2020515699A5 true JP2020515699A5 (https=) | 2021-05-06 |
Family
ID=63673906
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2019554393A Pending JP2020515699A (ja) | 2017-03-29 | 2018-03-28 | コーティング組成物、ポリマーコーティング、および方法 |
Country Status (9)
| Country | Link |
|---|---|
| US (2) | US12042580B2 (https=) |
| EP (1) | EP3601443B1 (https=) |
| JP (1) | JP2020515699A (https=) |
| CN (1) | CN110678521A (https=) |
| AU (2) | AU2018241528A1 (https=) |
| CA (1) | CA3057863C (https=) |
| ES (1) | ES3057442T3 (https=) |
| MX (1) | MX2019011571A (https=) |
| WO (1) | WO2018176138A1 (https=) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US11439797B2 (en) * | 2017-02-10 | 2022-09-13 | Medtronic Advanced Energy Llc. | Surgical drain system and container |
| EP3643758A1 (de) * | 2018-10-25 | 2020-04-29 | BIOTRONIK SE & Co. KG | Silikonwerkstoff mit modifizierter oberfläche zur verbesserung der gleit- und reibeigenschaften |
| EP3983141A4 (en) | 2019-06-14 | 2023-07-19 | Covalon Technologies Inc. | COATED DEVICES AND RELATED PROCESSES |
| CN110237309A (zh) * | 2019-06-24 | 2019-09-17 | 山东吉威医疗制品有限公司 | 一种用于球囊导管的亲水涂层溶液及制备和使用方法 |
| CN115066292B (zh) | 2019-12-17 | 2025-09-26 | 科发龙技术公司 | 涂覆器件的反应器以及相关系统和方法 |
| US12090298B2 (en) * | 2020-02-07 | 2024-09-17 | Carefusion 303, Inc. | Antimicrobial coating extending performance of needleless connector |
| US11905435B2 (en) | 2020-03-09 | 2024-02-20 | Pegasus Environmental Research And Investment Group Llc | Antimicrobial additive compositions for coatings |
| EP4101893B1 (en) * | 2021-06-08 | 2025-07-09 | SHPP Global Technologies B.V. | Thermoplastic compositions and shaped articles thereof |
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| US4479795A (en) * | 1979-06-29 | 1984-10-30 | The Procter & Gamble Company | Antimicrobial polymer compositions |
| US5100689A (en) * | 1987-04-10 | 1992-03-31 | University Of Florida | Surface modified surgical instruments, devices, implants, contact lenses and the like |
| KR910003714B1 (ko) * | 1987-11-12 | 1991-06-08 | 재단법인 한국화학연구소 | 무적성 고분자 물질 및 그의 제조방법 |
| WO1991003938A1 (en) * | 1989-09-20 | 1991-04-04 | Ecolab Incorporated | Antimicrobial polymeric coating |
| JPH03205759A (ja) * | 1990-06-15 | 1991-09-09 | Res Dev Corp Of Japan | アルカリ電池 |
| US5278200A (en) | 1992-10-30 | 1994-01-11 | Medtronic, Inc. | Thromboresistant material and articles |
| US5380790A (en) * | 1993-09-09 | 1995-01-10 | Eastman Chemical Company | Process for the preparation of acrylic polymers for pharmaceutical coatings |
| US6468649B1 (en) | 1995-02-22 | 2002-10-22 | Scimed Life Systems, Inc. | Antimicrobial adhesion surface |
| US5534562A (en) * | 1995-04-07 | 1996-07-09 | Ultradent Products, Inc. | Compositions and methods for priming and sealing dental and biological substrates |
| US5811151A (en) * | 1996-05-31 | 1998-09-22 | Medtronic, Inc. | Method of modifying the surface of a medical device |
| JP3139410B2 (ja) * | 1997-04-15 | 2001-02-26 | 富士ゼロックス株式会社 | グラフト重合方法 |
| US5968539A (en) * | 1997-06-04 | 1999-10-19 | Procter & Gamble Company | Mild, rinse-off antimicrobial liquid cleansing compositions which provide residual benefit versus gram negative bacteria |
| WO1998055098A1 (en) * | 1997-06-04 | 1998-12-10 | The Procter & Gamble Company | Mild, rinse-off antimicrobial liquid cleansing compositions containing acidic surfactants |
| US6403113B1 (en) | 1997-07-17 | 2002-06-11 | The Procter & Gamble Company | Anti-microbic agent |
| US6087415A (en) | 1998-06-11 | 2000-07-11 | Johnson & Johnson Vision Care, Inc. | Biomedical devices with hydrophilic coatings |
| US6358557B1 (en) * | 1999-09-10 | 2002-03-19 | Sts Biopolymers, Inc. | Graft polymerization of substrate surfaces |
| CA2392227C (en) * | 1999-11-22 | 2010-02-16 | Kuraray Co., Ltd. | Three component-containing acrylic adhesive composition |
| AU2002235694B2 (en) | 2001-02-28 | 2007-06-14 | Covalon Technologies Inc. | Method of making anti-microbial polymeric surfaces |
| EP1830638A2 (en) * | 2004-12-09 | 2007-09-12 | The Dial Corporation | Compositions having a high antiviral and antibacterial efficacy |
| CA2588833A1 (en) * | 2004-12-09 | 2007-04-19 | The Dial Corporation | Compositions having a high antiviral and antibacterial efficacy |
| US20070104925A1 (en) * | 2005-11-08 | 2007-05-10 | Hans-Jurgen Huber | Soft-hard moulded articles |
| WO2009015476A1 (en) * | 2007-08-02 | 2009-02-05 | Covalon Technologies Ltd. | Antimicrobial photo-stable coating composition |
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| EP2036930A1 (en) | 2007-09-12 | 2009-03-18 | Institut National De La Recherche Agronomique (Inra) | Copolymer-grafted polyolefin substrate having antimicrobial properties and method for grafting |
| JP5346194B2 (ja) * | 2007-09-29 | 2013-11-20 | 積水化学工業株式会社 | プロトン伝導性材料、膜―電極接合剤、プロトン伝導性膜、接合層付プロトン伝導性膜、膜−電極接合体及び固体高分子形燃料電池 |
| US8420069B2 (en) | 2008-09-26 | 2013-04-16 | 3M Innovative Properties Company | Antimicrobial and antifouling polymeric materials |
| JP5379563B2 (ja) * | 2009-06-01 | 2013-12-25 | 株式会社トクヤマデンタル | 歯のコーティング用キット |
| US8967077B2 (en) * | 2009-09-29 | 2015-03-03 | Covalon Technologies, Inc. | System and method for coating medical devices |
| MX2013008941A (es) * | 2011-02-07 | 2013-09-06 | Evonik Roehm Gmbh | Metodo para fabricar materiales acrilicos antimicrobianos. |
| WO2013006947A1 (en) * | 2011-07-08 | 2013-01-17 | Covalon Technologies Inc. | Method for treating a surface with a coating comprising a therapeutic agent and device with treated surface |
| US9422463B2 (en) * | 2012-02-29 | 2016-08-23 | Hollister, Inc. | Buffered adhesive compositions for skin-adhering medical products |
| AU2014211351B2 (en) * | 2013-02-04 | 2017-04-13 | W. L. Gore & Associates, Inc. | Coating for substrate |
| US9789228B2 (en) * | 2014-12-11 | 2017-10-17 | Covidien Lp | Antimicrobial coatings for medical devices and processes for preparing such coatings |
-
2018
- 2018-03-28 AU AU2018241528A patent/AU2018241528A1/en not_active Abandoned
- 2018-03-28 EP EP18776812.2A patent/EP3601443B1/en active Active
- 2018-03-28 JP JP2019554393A patent/JP2020515699A/ja active Pending
- 2018-03-28 US US15/938,537 patent/US12042580B2/en active Active
- 2018-03-28 CN CN201880034082.8A patent/CN110678521A/zh active Pending
- 2018-03-28 ES ES18776812T patent/ES3057442T3/es active Active
- 2018-03-28 MX MX2019011571A patent/MX2019011571A/es unknown
- 2018-03-28 CA CA3057863A patent/CA3057863C/en active Active
- 2018-03-28 WO PCT/CA2018/050376 patent/WO2018176138A1/en not_active Ceased
-
2023
- 2023-11-09 AU AU2023263512A patent/AU2023263512A1/en active Pending
-
2024
- 2024-07-19 US US18/778,274 patent/US20240374794A1/en active Pending
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