WO2010002524A2 - Methods for making antimicrobial coatings - Google Patents
Methods for making antimicrobial coatings Download PDFInfo
- Publication number
- WO2010002524A2 WO2010002524A2 PCT/US2009/045278 US2009045278W WO2010002524A2 WO 2010002524 A2 WO2010002524 A2 WO 2010002524A2 US 2009045278 W US2009045278 W US 2009045278W WO 2010002524 A2 WO2010002524 A2 WO 2010002524A2
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- metal
- substrate surface
- rubbers
- mixture
- mixtures
- Prior art date
Links
- 238000000576 coating method Methods 0.000 title claims abstract description 62
- 238000000034 method Methods 0.000 title claims abstract description 59
- 230000000845 anti-microbial effect Effects 0.000 title claims abstract description 32
- 239000000203 mixture Substances 0.000 claims abstract description 70
- 229910052751 metal Inorganic materials 0.000 claims abstract description 62
- 239000002184 metal Substances 0.000 claims abstract description 62
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- -1 biguanide compound Chemical class 0.000 claims abstract description 53
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- 239000004332 silver Substances 0.000 claims description 26
- 229910052723 transition metal Inorganic materials 0.000 claims description 22
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- 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 12
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- ZAQJHHRNXZUBTE-UHFFFAOYSA-N D-threo-2-Pentulose Natural products OCC(O)C(O)C(=O)CO ZAQJHHRNXZUBTE-UHFFFAOYSA-N 0.000 description 1
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- 229930091371 Fructose Natural products 0.000 description 1
- RFSUNEUAIZKAJO-ARQDHWQXSA-N Fructose Chemical compound OC[C@H]1O[C@](O)(CO)[C@@H](O)[C@@H]1O RFSUNEUAIZKAJO-ARQDHWQXSA-N 0.000 description 1
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- 208000007976 Ketosis Diseases 0.000 description 1
- LKDRXBCSQODPBY-AMVSKUEXSA-N L-(-)-Sorbose Chemical compound OCC1(O)OC[C@H](O)[C@@H](O)[C@@H]1O LKDRXBCSQODPBY-AMVSKUEXSA-N 0.000 description 1
- WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 description 1
- ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical class OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 description 1
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- 240000004808 Saccharomyces cerevisiae Species 0.000 description 1
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 1
- FOIXSVOLVBLSDH-UHFFFAOYSA-N Silver ion Chemical compound [Ag+] FOIXSVOLVBLSDH-UHFFFAOYSA-N 0.000 description 1
- 241000191967 Staphylococcus aureus Species 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 241000700605 Viruses Species 0.000 description 1
- JKNZUZCGFROMAZ-UHFFFAOYSA-L [Ag+2].[O-]S([O-])(=O)=O Chemical class [Ag+2].[O-]S([O-])(=O)=O JKNZUZCGFROMAZ-UHFFFAOYSA-L 0.000 description 1
- 230000003187 abdominal effect Effects 0.000 description 1
- 239000002250 absorbent Substances 0.000 description 1
- 230000002745 absorbent Effects 0.000 description 1
- GZCGUPFRVQAUEE-SLPGGIOYSA-N aldehydo-D-glucose Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C=O GZCGUPFRVQAUEE-SLPGGIOYSA-N 0.000 description 1
- 229940072056 alginate Drugs 0.000 description 1
- 235000010443 alginic acid Nutrition 0.000 description 1
- 229920000615 alginic acid Polymers 0.000 description 1
- JAZBEHYOTPTENJ-JLNKQSITSA-M all-cis-5,8,11,14,17-icosapentaenoate Chemical compound CC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CCCC([O-])=O JAZBEHYOTPTENJ-JLNKQSITSA-M 0.000 description 1
- MBMBGCFOFBJSGT-KUBAVDMBSA-N all-cis-docosa-4,7,10,13,16,19-hexaenoic acid Chemical compound CC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CCC(O)=O MBMBGCFOFBJSGT-KUBAVDMBSA-N 0.000 description 1
- 239000003945 anionic surfactant Substances 0.000 description 1
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- 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 description 1
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- 230000001332 colony forming effect Effects 0.000 description 1
- XLJMAIOERFSOGZ-UHFFFAOYSA-M cyanate Chemical compound [O-]C#N XLJMAIOERFSOGZ-UHFFFAOYSA-M 0.000 description 1
- GHVNFZFCNZKVNT-UHFFFAOYSA-N decanoic acid Chemical compound CCCCCCCCCC(O)=O GHVNFZFCNZKVNT-UHFFFAOYSA-N 0.000 description 1
- KXGVEGMKQFWNSR-LLQZFEROSA-M deoxycholate 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-M 0.000 description 1
- 229940009976 deoxycholate Drugs 0.000 description 1
- 230000005595 deprotonation Effects 0.000 description 1
- 238000010537 deprotonation reaction Methods 0.000 description 1
- 238000003745 diagnosis Methods 0.000 description 1
- HOBAELRKJCKHQD-QNEBEIHSSA-N dihomo-γ-linolenic acid Chemical compound CCCCC\C=C/C\C=C/C\C=C/CCCCCCC(O)=O HOBAELRKJCKHQD-QNEBEIHSSA-N 0.000 description 1
- 229940120503 dihydroxyacetone Drugs 0.000 description 1
- 230000003292 diminished effect Effects 0.000 description 1
- 235000019329 dioctyl sodium sulphosuccinate Nutrition 0.000 description 1
- 235000011180 diphosphates Nutrition 0.000 description 1
- 230000006806 disease prevention Effects 0.000 description 1
- YHAIUSTWZPMYGG-UHFFFAOYSA-L disodium;2,2-dioctyl-3-sulfobutanedioate Chemical compound [Na+].[Na+].CCCCCCCCC(C([O-])=O)(C(C([O-])=O)S(O)(=O)=O)CCCCCCCC YHAIUSTWZPMYGG-UHFFFAOYSA-L 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 229940000640 docosahexaenoate Drugs 0.000 description 1
- POULHZVOKOAJMA-UHFFFAOYSA-M dodecanoate Chemical compound CCCCCCCCCCCC([O-])=O POULHZVOKOAJMA-UHFFFAOYSA-M 0.000 description 1
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- 238000005516 engineering process Methods 0.000 description 1
- UQPHVQVXLPRNCX-UHFFFAOYSA-N erythrulose Chemical compound OCC(O)C(=O)CO UQPHVQVXLPRNCX-UHFFFAOYSA-N 0.000 description 1
- 239000010408 film Substances 0.000 description 1
- 238000009501 film coating Methods 0.000 description 1
- 230000002538 fungal effect Effects 0.000 description 1
- 229940066963 gamma-linolenate Drugs 0.000 description 1
- VZCCETWTMQHEPK-QNEBEIHSSA-N gamma-linolenic acid Chemical compound CCCCC\C=C/C\C=C/C\C=C/CCCCC(O)=O VZCCETWTMQHEPK-QNEBEIHSSA-N 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- 229960001031 glucose Drugs 0.000 description 1
- IPCSVZSSVZVIGE-UHFFFAOYSA-M hexadecanoate Chemical compound CCCCCCCCCCCCCCCC([O-])=O IPCSVZSSVZVIGE-UHFFFAOYSA-M 0.000 description 1
- FQKWHGOHXVHGMR-UHFFFAOYSA-N hexadecoxybenzene Chemical compound CCCCCCCCCCCCCCCCOC1=CC=CC=C1 FQKWHGOHXVHGMR-UHFFFAOYSA-N 0.000 description 1
- 229920001903 high density polyethylene Polymers 0.000 description 1
- VKOBVWXKNCXXDE-UHFFFAOYSA-M icosanoate Chemical compound CCCCCCCCCCCCCCCCCCCC([O-])=O VKOBVWXKNCXXDE-UHFFFAOYSA-M 0.000 description 1
- 150000002460 imidazoles Chemical group 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 230000002779 inactivation Effects 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
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- 229910001412 inorganic anion Inorganic materials 0.000 description 1
- 238000003780 insertion Methods 0.000 description 1
- 230000037431 insertion Effects 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-M iodide Chemical compound [I-] XMBWDFGMSWQBCA-UHFFFAOYSA-M 0.000 description 1
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 1
- BJHIKXHVCXFQLS-PQLUHFTBSA-N keto-D-tagatose Chemical compound OC[C@@H](O)[C@H](O)[C@H](O)C(=O)CO BJHIKXHVCXFQLS-PQLUHFTBSA-N 0.000 description 1
- 150000002584 ketoses Chemical class 0.000 description 1
- 229940070765 laurate Drugs 0.000 description 1
- 229940049918 linoleate Drugs 0.000 description 1
- DTOSIQBPPRVQHS-PDBXOOCHSA-M linolenate Chemical compound CC\C=C/C\C=C/C\C=C/CCCCCCCC([O-])=O DTOSIQBPPRVQHS-PDBXOOCHSA-M 0.000 description 1
- 150000002632 lipids Chemical class 0.000 description 1
- 229920001684 low density polyethylene Polymers 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000002923 metal particle Substances 0.000 description 1
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 1
- 239000011859 microparticle Substances 0.000 description 1
- 230000000116 mitigating effect Effects 0.000 description 1
- 229940105132 myristate Drugs 0.000 description 1
- 239000002736 nonionic surfactant Substances 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- 229940049964 oleate Drugs 0.000 description 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-M oleate Chemical compound CCCCCCCC\C=C/CCCCCCCC([O-])=O ZQPPMHVWECSIRJ-KTKRTIGZSA-M 0.000 description 1
- 150000002891 organic anions Chemical class 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 244000052769 pathogen Species 0.000 description 1
- WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 description 1
- 150000003904 phospholipids Chemical class 0.000 description 1
- 229920001983 poloxamer Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229920000136 polysorbate Polymers 0.000 description 1
- 229940068965 polysorbates Drugs 0.000 description 1
- 229920000915 polyvinyl chloride Polymers 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229940114930 potassium stearate Drugs 0.000 description 1
- ANBFRLKBEIFNQU-UHFFFAOYSA-M potassium;octadecanoate Chemical compound [K+].CCCCCCCCCCCCCCCCCC([O-])=O ANBFRLKBEIFNQU-UHFFFAOYSA-M 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000003672 processing method Methods 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 230000005588 protonation Effects 0.000 description 1
- 150000003856 quaternary ammonium compounds Chemical class 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 229910000077 silane Inorganic materials 0.000 description 1
- CQLFBEKRDQMJLZ-UHFFFAOYSA-M silver acetate Chemical class [Ag+].CC([O-])=O CQLFBEKRDQMJLZ-UHFFFAOYSA-M 0.000 description 1
- XQLMNMQWVCXIKR-UHFFFAOYSA-M silver bromate Chemical class [Ag+].[O-]Br(=O)=O XQLMNMQWVCXIKR-UHFFFAOYSA-M 0.000 description 1
- SDLBJIZEEMKQKY-UHFFFAOYSA-M silver chlorate Chemical class [Ag+].[O-]Cl(=O)=O SDLBJIZEEMKQKY-UHFFFAOYSA-M 0.000 description 1
- YSVXTGDPTJIEIX-UHFFFAOYSA-M silver iodate Chemical class [Ag+].[O-]I(=O)=O YSVXTGDPTJIEIX-UHFFFAOYSA-M 0.000 description 1
- 229960003600 silver sulfadiazine Drugs 0.000 description 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 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 229940114926 stearate Drugs 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
- 229960004306 sulfadiazine Drugs 0.000 description 1
- 150000003871 sulfonates Chemical class 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 239000013589 supplement Substances 0.000 description 1
- 230000002195 synergetic effect Effects 0.000 description 1
- 239000003760 tallow Substances 0.000 description 1
- QZZGJDVWLFXDLK-UHFFFAOYSA-M tetracosanoate Chemical compound CCCCCCCCCCCCCCCCCCCCCCCC([O-])=O QZZGJDVWLFXDLK-UHFFFAOYSA-M 0.000 description 1
- TUNFSRHWOTWDNC-UHFFFAOYSA-N tetradecanoic acid Chemical compound CCCCCCCCCCCCCC(O)=O TUNFSRHWOTWDNC-UHFFFAOYSA-N 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 150000003573 thiols Chemical group 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 239000001974 tryptic soy broth Substances 0.000 description 1
- 239000006150 trypticase soy agar Substances 0.000 description 1
- 108010050327 trypticase-soy broth Proteins 0.000 description 1
- 230000002485 urinary effect Effects 0.000 description 1
- 230000003612 virological effect Effects 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000002888 zwitterionic surfactant Substances 0.000 description 1
Classifications
-
- 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
- C23C18/00—Chemical coating by decomposition of either liquid compounds or solutions of the coating forming compounds, without leaving reaction products of surface material in the coating; Contact plating
- C23C18/16—Chemical coating by decomposition of either liquid compounds or solutions of the coating forming compounds, without leaving reaction products of surface material in the coating; Contact plating by reduction or substitution, e.g. electroless plating
- C23C18/1601—Process or apparatus
- C23C18/1633—Process of electroless plating
- C23C18/1689—After-treatment
-
- 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
- A61L29/14—Materials characterised by their function or physical properties, e.g. lubricating compositions
-
- 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
- C23C18/00—Chemical coating by decomposition of either liquid compounds or solutions of the coating forming compounds, without leaving reaction products of surface material in the coating; Contact plating
- C23C18/16—Chemical coating by decomposition of either liquid compounds or solutions of the coating forming compounds, without leaving reaction products of surface material in the coating; Contact plating by reduction or substitution, e.g. electroless plating
- C23C18/1601—Process or apparatus
- C23C18/1633—Process of electroless plating
- C23C18/1655—Process features
- C23C18/1662—Use of incorporated material in the solution or dispersion, e.g. particles, whiskers, wires
-
- 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
- C23C18/00—Chemical coating by decomposition of either liquid compounds or solutions of the coating forming compounds, without leaving reaction products of surface material in the coating; Contact plating
- C23C18/16—Chemical coating by decomposition of either liquid compounds or solutions of the coating forming compounds, without leaving reaction products of surface material in the coating; Contact plating by reduction or substitution, e.g. electroless plating
- C23C18/1601—Process or apparatus
- C23C18/1633—Process of electroless plating
- C23C18/1675—Process conditions
- C23C18/1676—Heating of the solution
-
- 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
- C23C18/00—Chemical coating by decomposition of either liquid compounds or solutions of the coating forming compounds, without leaving reaction products of surface material in the coating; Contact plating
- C23C18/16—Chemical coating by decomposition of either liquid compounds or solutions of the coating forming compounds, without leaving reaction products of surface material in the coating; Contact plating by reduction or substitution, e.g. electroless plating
- C23C18/31—Coating with metals
-
- 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
- C23C18/00—Chemical coating by decomposition of either liquid compounds or solutions of the coating forming compounds, without leaving reaction products of surface material in the coating; Contact plating
- C23C18/16—Chemical coating by decomposition of either liquid compounds or solutions of the coating forming compounds, without leaving reaction products of surface material in the coating; Contact plating by reduction or substitution, e.g. electroless plating
- C23C18/31—Coating with metals
- C23C18/42—Coating with noble metals
- C23C18/44—Coating with noble metals using reducing agents
Definitions
- the disclosure relates generally to antimicrobial coating compositions and methods for making and processing such coatings. More particularly, the disclosure is directed to methods of making antimicrobial coating compositions comprising transition metals, methods for forming such coatings on substrates, such as medical devices, and methods for processing such coatings.
- Silver and salts thereof are commonly used because of their demonstrated broad spectrum antimicrobial activity against various bacteria, viruses, yeast, fungi, and protozoa. It is theorized that the observed antimicrobial activity is primarily due to the ability of silver ions to tightly bind nucleophilic functional groups containing sulfur, oxygen or nitrogen. Many nucleophilic functional groups such as thiols, carboxylates, phosphates, alcohols, amines, imidazoles, and indoles are prevalent in biomolecules. Upon binding of ionized silver to these various nucleophilic functional groups, it is believed that widespread disruption and inactivation of microbial biomolecules (and thus antimicrobial activity) occurs.
- Silver and salts thereof have therefore been used as antimicrobial agents in a wide variety of applications; for example, they have been incorporated in the absorbent materials of wound care products such as dressings, gels, and bandages, and also in compositions for providing antimicrobial coatings on medical devices.
- Polymeric binders frequently are added to such silver- or silver salt-containing compositions in order to facilitate manufacturing and/or deposition.
- One disadvantage frequently observed with such antimicrobial compositions involves relatively poor silver ion elution.
- Many polymer binder- containing silver or silver salt compositions also can exhibit unsatisfactory antimicrobial efficacy profiles. Various factors can contribute to undesirable efficacy profiles, such as nonuniform thickness of the coating.
- One disadvantage of some metallic silver-containing antimicrobial coatings is their color/opaqueness, which prevents a healthcare provider from being able to see through the medical device substrate.
- Thin film coatings comprising silver for example, can be brown in color. Thus, when such colored silver films are applied to transparent surfaces, the coated surfaces typically have a brown color and significantly diminished transparency.
- coatings comprising silver salts are transparent or translucent, and/or lack a colored appearance.
- the coated surfaces typically have little color and are highly transparent. While coatings comprising silver salts are often translucent, it is extremely difficult to solubilize such compounds and thus to directly deposit coatings comprising silver salts.
- the present disclosure is directed to methods for forming an antimicrobial coating on a substrate surface.
- the methods include providing a mixture comprising a transition metal, a biguanide compound, and a reducing agent; and depositing the mixture onto a substrate surface, thereby forming a coated substrate surface.
- the mixture is free of polymeric binders.
- the substrate surfaces can comprise plastic, glass, metal, or mixtures or laminates thereof.
- the substrate surfaces can comprise surfaces of medical devices or medical device components. Preferred examples of substrate surfaces include polycarbonate medical devices.
- the substrate surface also can comprise surfaces of medical fluid containers or medical fluid flow systems. Preferred examples of medical fluid flow systems include LV. sets and components thereof, such as luer access devices.
- the transition metals can comprise various metals or mixtures of metals.
- Preferred metals include silver, copper, gold, zinc, cerium, platinum, palladium, and tin.
- a coating composition comprising an aqueous solution containing a reducing agent and a complex comprising ionic silver and chlorhexidine, wherein the solution is free of polymeric binders.
- the present disclosure is directed to methods for forming an antimicrobial coating on a substrate surface.
- the methods according to the disclosure involve providing a mixture comprising a transition metal, a biguanide compound, and a reducing agent; and depositing the mixture onto a substrate surface, thereby forming a coated substrate surface.
- the mixture is free of polymeric binders.
- the substrate surfaces of the present disclosure can comprise various materials including, for example, glasses, metals, plastics, ceramics, and elastomers, as well as mixtures and/or laminates thereof.
- plastics include acrylonitrile butadiene styrenes, polyacrylonitriles, polyamides, polycarbonates, polyesters, polyetheretherketones, polyetherimides, polyethylenes such as high density polyethylenes and low density polyethylenes, polyethylene terephthalates, polylactic acids, polymethyl methyacrylates, polypropylenes, polystyrenes, polyurethanes, polyvinyl chlorides), polyvinylidene chlorides, polyethers, polysulfones, silicones, and blends and copolymers thereof.
- Suitable elastomers include, but are not limited to,natural rubbers, and synthetic rubbers, such as styrene butadiene rubbers, ethylene propylene diene monomer rubbers (EPDM), polychloroprene rubbers (CR), acrylonitrile butadiene rubbers (NBR), chlorosuphonated polyethylene rubbers (CSM), polyisoprene rubbers, isobutylene-isoprene copolymeric rubbers, chlorinated isobutylene-isoprene copolymeric rubbers, brominated isobutylene-isoprene copolymeric rubbers, and blends and copolymers thereof.
- synthetic rubbers such as styrene butadiene rubbers, ethylene propylene diene monomer rubbers (EPDM), polychloroprene rubbers (CR), acrylonitrile butadiene rubbers (NBR), chlorosuphonated polyethylene rubbers (CSM), polyis
- the antimicrobial coating is formed on (or applied to) a surface of a medical device or medical device component.
- Medical devices and medical device components which can benefit from the methods according to the disclosure, include, but are not limited to, instruments, apparatuses, implements, machines, contrivances, implants, and components and accessories thereof, intended for use in the diagnosis, cure, mitigation, treatment, or prevention of disease or other condition in humans or other animals, or intended to affect the structure or any function of the body of humans or other animals.
- Such medical devices are described, for example, in the official National Formulary, the United States Pharmacopoeia, and any supplements thereto.
- Representative medical devices include, but are not limited to: catheters, such as venous catheters, urinary catheters, Foley catheters, and pain management catheters; stents; abdominal plugs; feeding tubes; cotton gauzes; wound dressings; contact lenses; lens cases; bandages; sutures; hernia meshes; mesh-based wound coverings, implants, metal screws, and metal plates.
- Additional exemplary medical devices include, but are not limited to, medical fluid containers, medical fluid flow systems, and medical devices such as stethoscopes which regularly come into contact with a patient.
- a medical fluid flow system is an intravenous fluid administration set, also known as an LV. set, used for the intravenous administration of fluids to a patient.
- a typical LV is an intravenous fluid administration set
- LV. sets optionally include one or more access devices providing access to the fluid flow path to allow fluid to be added to or withdrawn from the IV tubing. Access devices advantageously eliminate the need to repeatedly phlebotomize the subject and allow for immediate administration of medication or other fluids to the subject, as is well known. Access devices can be designed for use with connecting apparatus employing standard luers, and such devices are commonly referred to as "luer access devices,” “luer- activated devices,” or “LADs.” LADs can be modified with one or more features such as antiseptic indicating devices. Various LADs are illustrated in U.S. Pat.
- LV. sets can incorporate additional optional components including, for example, septa, stoppers, stopcocks, connectors, adaptors, clamps, extension sets, filters, and the like.
- suitable medical devices and medical device components which may be processed in accordance with the methods of the present disclosure include, but are not limited to: LV. tubing, LV. fluid bags, LV. set access devices, septa, stopcocks, LV. set connectors, LV. set adaptors, clamps, LV. filters, catheters, needles, stethoscopes, and cannulae.
- Representative access devices include, but are not limited to: luer access devices and needleless luer access devices.
- the surface of the medical device or medical device component can be fully or partially coated with the antimicrobial coating.
- the coating can be formed on (or applied to) an exterior surface of the device (i.e., a surface which is intended to come into contact with a patient or healthcare provider), an interior surface of the device (i.e. a surface which is not intended to come into contact with a patient or healthcare provider, but which can come into contact with the patient's blood or other fluids), or both.
- Suitable medical devices and medical device components are illustrated in U.S. Pat. Nos.
- the coatings of the present disclosure can comprise transition metals or mixtures of transition metals.
- the transition metals are typically selected to have antimicrobial properties.
- Suitable metals for use in the compositions include, but are not limited to: silver, copper, gold, zinc, cerium, platinum, palladium, and tin. Coatings comprising a combination of two or more of the foregoing metals can also be used.
- the transition metal is provided as a water-soluble metal salt.
- Suitable water-soluble metal salts have a solubility product (K, p ) greater than about 10 "8 , for example, greater than about I O 6 , greater than about 10 4 , and/or greater than about 10 "2 .
- Suitable metal salts include, but are not limited to: metal sulfadiazines, metal acetates, metal sulfates, metal nitrates, metal chlorates, metal bromates, metal iodates, and mixtures of the foregoing.
- Exemplary metal salts include, but are not limited to, silver salts, such as silver sulfadiazine, silver acetates, silver sulfates, silver nitrates, silver chlorates, silver bromates, silver iodates, and mixtures of the foregoing.
- the transition metal is provided as a metal biguanide complex.
- suitable metal biguanide complexes include, but are not limited to: metal chlorhexidine complexes, metal carbamimidoyl guanidine complexes, metal metformin complexes, metal buformin complexes, metal phenformin complexes, and mixtures and derivatives thereof.
- Exemplary metal biguanide complexes include, but are not limited to: silver chlorhexidine complexes, silver carbamimidoyl guanidine complexes, silver metformin complexes, silver buformin complexes, silver phenformin complexes, and mixtures and derivatives thereof.
- the transition metals in accordance with the present disclosure can comprise particles, such as microparticles or nanoparticles.
- the metal particles typically have a diameter in the range of about 1 nanometer to about 50 micrometers, for example, from about 10 nanometers to about 25 micrometers, from about 50 nanometers to about 10 micrometers, and/or from about 100 nm to about 1 micrometer.
- the coatings comprise a biguanide compound.
- suitable biguanide compounds include, but are not limited to chlorhexidine, chlorhexidine salts, carbamimidoyl guanidines, metformin, buformin, phenformin, and mixtures and derivatives thereof.
- Exemplary chlorhexidine salts include chlorhexidine acetates, chlorhexidine gluconates, chlorhexidine hydrochlorides, chlorhexidine sulfates, and mixtures of the foregoing.
- the transition metal and the biguanide compound can be selected to have a synergistic effect.
- One preferred combination comprises silver and chlorhexidine.
- the coatings comprise a reducing agent. It is theorized that the reducing agent facilitates deposition of the coating on the substrate surface by reducing the transition metal, while the reducing agent itself becomes oxidized.
- the methods disclosed herein further comprise partially reducing the transition metal. Partial reduction of the metal can be carried out by preventing the reduction reaction from reaching completion, for example, by removing the substrate from the reaction mixture after a period of time shorter than the period of time necessary for the reaction to reach completion or by providing a sub-stoichiometric amount of the reducing agent relative to the metal.
- Partial reduction of the metal can be beneficial, as this allows the coating surface to comprise a mixture of metals having different oxidation states, including both fully reduced and non-reduced metals.
- Silver coatings for example, can comprise a mixture of Ag(O) and Ag(I). Metals having different oxidation states may have different efficacies against different pathogens, and/or different elution profiles. Further, by only conducting partial reduction, a certain amount of the transition metal remains in the bulk composition whereas a majority of the metal, when fully reduced, is deposited at the surface of the coating. Such coatings comprising less fully reduced metal at the surface of the coating can display improved elution profiles and/or increased efficacy.
- Suitable reducing agents can be used provided the reducing agent has a sufficient reduction potential to partially reduce the metal of the coating.
- Suitable reducing agents for use in the disclosed methods include, but are not limited to, aldehydes and alcohols such as, acyclic aliphatic aldehydes, cyclic aliphatic aldehydes, aryl aldehydes, aldoses, acyclic aliphatic alcohols, cyclic aliphatic alcohols, aryl alcohols, ketoses, and mixtures of the foregoing.
- Exemplary aldehydes include glyceraldehyde, erythrose, threose, ribose, arabinose, xylose, lyxose, allose, altrose, glucose, mannose, gulose, idose, galactose, talose, formaldehyde, and mixtures of the foregoing.
- Exemplary alcohols include dihydroxyacetone, erythrulose, ribulose, xylulose, fructose, psicose, sorbose, tagatose, methanol, ethanol, benzyl alcohol, and mixtures of the foregoing.
- the antimicrobial coatings in accordance with the present disclosure are free of polymeric binders.
- the antimicrobial coating formulations can comprise one or more additives.
- Suitable additives include, but are not limited to: adhesion promoters, such as silane adhesion promoters and N-vinyl pyrrolidone; and cationic, anionic, non-ionic, and zwitterionic surfactants, such as lipids, fatty acid salts (e.g., sodium laureate, potassium linoleate, potassium stearate), quaternary ammonium compounds (e.g., hexadecyl trimethyl ammonium bromide), polyethoxylated tallow amines, benzethonium chloride, polysorbates, PLURONIC® copolymers, and sulfates (e.g., potassium hexadecyl phenyl ether sulfonate, potassium resorcinol dio
- the antimicrobial coatings of the present disclosure are formed by providing a mixture comprising one or more transition metals, one or more biguanide compounds, and one or more reducing agents; and depositing the mixture onto a substrate surface, thereby forming a coated substrate surface.
- Depositing the mixture onto the substrate surface can be carried out by various means, for example, soaking, dipping, and/or swabbing.
- depositing the mixture onto the substrate surface comprises heating the mixture, for example, to a temperature of about 40 0 C to about 80 0 C.
- the disclosure also is directed to a coating composition
- a coating composition comprising an aqueous solution containing a reducing agent and a complex comprising ionic silver and chlorhexidine.
- the antimicrobial coatings of the present disclosure can be further processed by exposing the previously formed coating to a mixture comprising an oxidizing agent and an anion.
- a mixture comprising an oxidizing agent and an anion As previously discussed, many metallic coatings are opaque, or exhibit a colored appearance. Some silver coatings, for example, are brown in color, and thus substrates carrying such coatings typically have a brown color and exhibit poor transparency.
- Exposing such substrate surfaces to a mixture of an oxidizing agent and an anion according to the methods disclosed herein can advantageously increase the transparency of the metal coating, thereby providing, for example, an efficient method for obtaining medical devices comprising a more transparent antimicrobial coating. Accordingly, the disclosed methods can advantageously increase the transparency of such coatings and hence the transparency of substrate surfaces carrying such coatings.
- coatings comprising metal salts are transparent or translucent, and/or lack a colored appearance.
- substrates carrying such coatings typically are clear or have a light color, and can be highly transparent.
- Exposing substrate surfaces carrying metal coatings to a mixture of an oxidizing agent and an anion according to the methods disclosed herein is envisioned to form metal salts comprising an oxidized form of the metal complexed with the anion as a counterion. Accordingly, it is believed the disclosed methods can advantageously form metal salts in the coatings, thereby increasing the transparency of such coatings and hence the transparency of substrate surfaces carrying such coatings.
- the antimicrobial activity and the optical properties of coatings processed according to the methods disclosed herein can be affected by various chemical properties of the coatings, such as the incorporation of the anion in the coatings, the formation of metal salts comprising an oxidized form of the metal complexed with the anion as a counterion, and other factors.
- Exposing a substrate surface carrying a coating comprising a metal to a mixture of an oxidizing agent and an anion according to the methods disclosed herein can alter the chemical properties of the coating, for example, by causing formation of metal salts, thereby providing nanoparticle coatings having increased antimicrobial efficacy and/or improved optical properties.
- the oxidizing agents of the present disclosure include a wide variety of known agents for oxidizing metals. Suitable oxidizing agents include metal ions and metal- containing compounds, such as Fe + , Fe 2+ , Cu 2+ , Cu + , MnO 4 " , and Ce 4+ ; halogens and halogen-containing compounds, such as 1O 3 , I 3 " , I 2 , BrO 3 , Br 2 , Br 3 " , ClO 3 " and Cl 2 ; inorganic and organic compounds of oxygen, such as NO 3 " , O 2 , S 2 O 8 2" , H 2 O 2 , quinones, and fumarate; and methylene blue. Mixtures of oxidizing agents also are included.
- any known oxidizing agent could be used provided it has a sufficient oxidation potential to at least partially oxidize the metal included in the coating.
- concentrations of the oxidizing agent can be used, and these oxidizing agent concentrations can be readily determined by one of ordinary skill. Typical amounts of oxidizing agent can range from about 0.0001 M to about 5 M, for example, about 0.001 M to about 5 M, about 0.01 M to about 2.5 M, about 0.05 M to about 1 M, and/or about 0.1 M to about 0.5 M, but higher and lower concentrations of oxidizing agents also can be used.
- the anions of the present disclosure include a wide variety of known anions, including organic and inorganic anions.
- Suitable anions include carboxylates, such as acetate, citrate, deoxycholate, fatty acid anions (e.g., decanoate, laurate, myristate, palmitate, stearate, eicosanoate, docsanoate, tetracosanoate, ⁇ -linolenate, stearidonate, eicosapentaenoate, docosahexaenoate, linoleate, ⁇ -linolenate, dihomo- ⁇ -linolenate, arachidonate, oleate, erucate, and nervonate), succinate, anionic carboxymethylcellulose, and alginate; halides, such as, fluoride, chloride, bromide, and iodide; halogen-containing anionic compounds, such as chlorate
- Anions may also be used.
- concentrations of the anion can be used, and these anion concentration can be readily determined by one of ordinary skill.
- Typical amounts of anion can range from about 0.0001 M to about 10 M, for example, about 0.001 M to about 7 M, about 0.01 M to about 5 M, about 0.05 M to about 2.5 M, and/or about 0.1 M to about 1 M, but higher and lower concentrations of anions also can be used.
- the oxidizing agent and the anion of the present disclosure can be the same.
- “dual oxidizing agents/anions” include chlorate (ClO 3 " ), bromate (BrO 3 " ), and iodate (1O 3 " ).
- the oxidizing agent and/or the anion also can be generated in situ, for example, by dissolution of a salt in a solution, by protonation or deprotonation, or by a reaction that produces the oxidizing agent and/or anion.
- FeCl 3 can dissolve in aqueous solution to form Fe 3+ as an oxidizing agent and Cl " as an anion, or I 2 can react in aqueous solution to form H 2 OI + and iodide (T) as an anion.
- An equilibrium reaction also can generate the oxidizing agent and/or the anion.
- the exposing to the mixture comprising an oxidizing agent and an anion comprises exposing the substrate surface to povidone iodine.
- Povidone iodine comprises a complex of molecular iodine (I 2 ) with polyvinyl pyrrolidone (PVP).
- PVP polyvinyl pyrrolidone
- Molecular iodine is a known oxidizing agent, and as discussed above, the iodide anion can be obtained in aqueous solution, for example, from ⁇ .
- the substrate surfaces of the present disclosure can be exposed to the mixture comprising the oxidizing agent and anion by various known methods. Typical methods for exposing the substrate surface to the mixture comprising the oxidizing agent and anion include dipping, immersing, soaking, submerging, swabbing, spraying, washing, or otherwise contacting the substrate surface with the mixture comprising the oxidizing agent and the anion.
- the substrate surfaces can be exposed to the mixture comprising the oxidizing agent and anion for various periods of time. The length of desired exposure can be readily determined by one of ordinary skill, and can vary depending on the reactivity of the mixture comprising the oxidizing agent and the anion and/or the desired properties of the final coating composition.
- the substrate surface is exposed for about 0.1 seconds to about 24 hours, but shorter and longer exposure periods can be used.
- the substrate surface is exposed to the mixture of the oxidizing agent and anion for about 0.1 seconds to about 2 hours, about 0.5 seconds to about 1 hour, about 1 second to about 30 minutes, and/or about 1 minute to about 10 minutes.
- the substrate surfaces also can be sequentially exposed to more than one mixture comprising an oxidizing agent and an anion, the second mixture of which may be the same as or different from the first mixture.
- Example 1 The antimicrobial activity of coated surface prepared according to the procedure in Example 1 was tested against Staphylococcus aureus (S. aureus).
- a suspension of S. aureus was grown in tryptic soy broth for 18-24 hours.
- the suspension was then diluted in saline to 2.63 x 10 colony-forming units per mL (cfu/mL). Tubes containing 5 mL saline were inoculated with 0.1 mL (2.63 x 10 4 cfu) of the suspension.
- the coated surfaces were aseptically added to the tubes, which were incubated at 23 0 C for 48 hours.
- the samples then were plated in tryptic soy agar in triplicate and incubated at 23 0 C for 48 hours. After this time, growth of S. aureus was measured, as shown in Table 1.
- Table 1 Table 1
- the coating comprising silver and chlorhexidine demonstrated antimicrobial activity against 5. aureus, as determined by a comparison of S. aureus recovery from a coated substrate to 5. aureus recovery from a substrate lacking a silver/chlorhexidine coating.
- the silver coatings prepared accorded to the disclosed methods showed greater than a 300-fold reduction in S. aureus growth compared to an uncoated surface.
Abstract
Description
Claims
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US12/164,414 US20090324738A1 (en) | 2008-06-30 | 2008-06-30 | Methods for making antimicrobial coatings |
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WO2010002524A3 (en) | 2010-05-14 |
EP2304077B1 (en) | 2012-05-16 |
AU2009265079A1 (en) | 2010-01-07 |
CA2724698A1 (en) | 2010-01-07 |
AU2009265079B2 (en) | 2013-07-04 |
EP2304077A2 (en) | 2011-04-06 |
US20090324738A1 (en) | 2009-12-31 |
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