OA16743A - Antimicrobial ionomer composition and uses thereof. - Google Patents
Antimicrobial ionomer composition and uses thereof. Download PDFInfo
- Publication number
- OA16743A OA16743A OA1201400074 OA16743A OA 16743 A OA16743 A OA 16743A OA 1201400074 OA1201400074 OA 1201400074 OA 16743 A OA16743 A OA 16743A
- Authority
- OA
- OAPI
- Prior art keywords
- silver
- antimicrobial
- composition according
- ionomer composition
- halide
- Prior art date
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 247
- 229920000554 ionomer Polymers 0.000 title claims abstract description 135
- 230000000845 anti-microbial Effects 0.000 title claims abstract description 116
- 239000004332 silver Substances 0.000 claims abstract description 99
- 229910052709 silver Inorganic materials 0.000 claims abstract description 99
- 150000001412 amines Chemical class 0.000 claims abstract description 46
- -1 silver halide Chemical class 0.000 claims abstract description 46
- 239000000463 material Substances 0.000 claims abstract description 35
- 229920001002 functional polymer Polymers 0.000 claims abstract description 34
- 239000003381 stabilizer Substances 0.000 claims abstract description 30
- 239000000126 substance Substances 0.000 claims abstract description 30
- 150000001875 compounds Chemical class 0.000 claims abstract description 27
- 239000004599 antimicrobial Substances 0.000 claims abstract description 26
- 239000000654 additive Substances 0.000 claims abstract description 22
- 239000011248 coating agent Substances 0.000 claims abstract description 21
- 238000000576 coating method Methods 0.000 claims abstract description 19
- 230000000996 additive Effects 0.000 claims abstract description 17
- 229910000039 hydrogen halide Inorganic materials 0.000 claims abstract description 13
- 239000012433 hydrogen halide Substances 0.000 claims abstract description 13
- 230000000087 stabilizing Effects 0.000 claims abstract description 5
- BQCADISMDOOEFD-UHFFFAOYSA-N silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 claims description 78
- 229920002873 Polyethylenimine Polymers 0.000 claims description 40
- 239000000835 fiber Substances 0.000 claims description 38
- 239000002904 solvent Substances 0.000 claims description 37
- 239000011159 matrix material Substances 0.000 claims description 31
- 229920000642 polymer Polymers 0.000 claims description 30
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 27
- CVHZOJJKTDOEJC-UHFFFAOYSA-N Saccharin Chemical compound C1=CC=C2C(=O)NS(=O)(=O)C2=C1 CVHZOJJKTDOEJC-UHFFFAOYSA-N 0.000 claims description 26
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 26
- 235000019441 ethanol Nutrition 0.000 claims description 24
- 229940081974 Saccharin Drugs 0.000 claims description 22
- 239000004744 fabric Substances 0.000 claims description 22
- 235000019204 saccharin Nutrition 0.000 claims description 22
- 239000000901 saccharin and its Na,K and Ca salt Substances 0.000 claims description 22
- 239000000047 product Substances 0.000 claims description 21
- HKZLPVFGJNLROG-UHFFFAOYSA-M Silver chloride Chemical group [Cl-].[Ag+] HKZLPVFGJNLROG-UHFFFAOYSA-M 0.000 claims description 16
- 239000003431 cross linking reagent Substances 0.000 claims description 14
- 150000004820 halides Chemical class 0.000 claims description 14
- 239000003795 chemical substances by application Substances 0.000 claims description 13
- 150000003379 silver compounds Chemical class 0.000 claims description 13
- VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 9
- 230000000249 desinfective Effects 0.000 claims description 9
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 claims description 8
- 125000002091 cationic group Chemical group 0.000 claims description 8
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 8
- 238000004659 sterilization and disinfection Methods 0.000 claims description 8
- 235000019270 ammonium chloride Nutrition 0.000 claims description 7
- 239000012263 liquid product Substances 0.000 claims description 7
- QDHHCQZDFGDHMP-UHFFFAOYSA-N monochloramine Chemical compound ClN QDHHCQZDFGDHMP-UHFFFAOYSA-N 0.000 claims description 7
- 239000000123 paper Substances 0.000 claims description 7
- 229920000297 Rayon Polymers 0.000 claims description 6
- 229920000742 Cotton Polymers 0.000 claims description 5
- 150000001298 alcohols Chemical class 0.000 claims description 5
- 239000003513 alkali Substances 0.000 claims description 5
- 229920001577 copolymer Polymers 0.000 claims description 5
- 239000002023 wood Substances 0.000 claims description 5
- 150000001450 anions Chemical class 0.000 claims description 4
- 230000001877 deodorizing Effects 0.000 claims description 4
- 229920000578 graft polymer Polymers 0.000 claims description 4
- XEEYBQQBJWHFJM-UHFFFAOYSA-N iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 4
- 229920000728 polyester Polymers 0.000 claims description 4
- 239000004952 Polyamide Substances 0.000 claims description 3
- NOWKCMXCCJGMRR-UHFFFAOYSA-N aziridine Chemical compound C1CN1 NOWKCMXCCJGMRR-UHFFFAOYSA-N 0.000 claims description 3
- 230000027455 binding Effects 0.000 claims description 3
- 229910000041 hydrogen chloride Inorganic materials 0.000 claims description 3
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 claims description 3
- 239000003446 ligand Substances 0.000 claims description 3
- 229920002647 polyamide Polymers 0.000 claims description 3
- 239000002759 woven fabric Substances 0.000 claims description 3
- HCAJEUSONLESMK-UHFFFAOYSA-N Cyclamic acid Chemical compound OS(=O)(=O)NC1CCCCC1 HCAJEUSONLESMK-UHFFFAOYSA-N 0.000 claims description 2
- 210000003491 Skin Anatomy 0.000 claims description 2
- 229920002678 cellulose Polymers 0.000 claims description 2
- 239000001913 cellulose Substances 0.000 claims description 2
- 239000000460 chlorine Substances 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 2
- 239000000625 cyclamic acid and its Na and Ca salt Substances 0.000 claims description 2
- UYMKPFRHYYNDTL-UHFFFAOYSA-N ethenamine Chemical compound NC=C UYMKPFRHYYNDTL-UHFFFAOYSA-N 0.000 claims description 2
- 229910052742 iron Inorganic materials 0.000 claims description 2
- 239000004745 nonwoven fabric Substances 0.000 claims description 2
- 239000000049 pigment Substances 0.000 claims description 2
- 229920002717 polyvinylpyridine Polymers 0.000 claims description 2
- 108090000623 proteins and genes Proteins 0.000 claims description 2
- 102000004169 proteins and genes Human genes 0.000 claims description 2
- 150000004760 silicates Chemical class 0.000 claims description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 2
- 239000011780 sodium chloride Substances 0.000 claims description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 2
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 claims 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 claims 2
- 229960005164 ACESULFAME Drugs 0.000 claims 1
- YGCFIWIQZPHFLU-UHFFFAOYSA-N acesulfame Chemical compound CC1=CC(=O)NS(=O)(=O)O1 YGCFIWIQZPHFLU-UHFFFAOYSA-N 0.000 claims 1
- 150000003863 ammonium salts Chemical class 0.000 claims 1
- 150000001805 chlorine compounds Chemical class 0.000 claims 1
- 229920000962 poly(amidoamine) Polymers 0.000 claims 1
- 239000001103 potassium chloride Substances 0.000 claims 1
- 235000011164 potassium chloride Nutrition 0.000 claims 1
- SEEPANYCNGTZFQ-UHFFFAOYSA-N sulfadiazine Chemical compound C1=CC(N)=CC=C1S(=O)(=O)NC1=NC=CC=N1 SEEPANYCNGTZFQ-UHFFFAOYSA-N 0.000 claims 1
- 229960004306 sulfadiazine Drugs 0.000 claims 1
- 229960001663 sulfanilamide Drugs 0.000 claims 1
- 229920000768 polyamine Polymers 0.000 abstract description 6
- 230000015572 biosynthetic process Effects 0.000 abstract description 5
- 238000005755 formation reaction Methods 0.000 abstract description 5
- 125000000565 sulfonamide group Chemical group 0.000 abstract description 2
- GGCZERPQGJTIQP-UHFFFAOYSA-M Sodium 2-anthraquinonesulfonate Chemical compound [Na+].C1=CC=C2C(=O)C3=CC(S(=O)(=O)[O-])=CC=C3C(=O)C2=C1 GGCZERPQGJTIQP-UHFFFAOYSA-M 0.000 abstract 1
- 229910001507 metal halide Inorganic materials 0.000 abstract 1
- OGFYIDCVDSATDC-UHFFFAOYSA-N silver silver Chemical compound [Ag].[Ag] OGFYIDCVDSATDC-UHFFFAOYSA-N 0.000 abstract 1
- 239000000243 solution Substances 0.000 description 60
- 238000002156 mixing Methods 0.000 description 23
- 230000000844 anti-bacterial Effects 0.000 description 16
- 238000000034 method Methods 0.000 description 16
- 229920001601 polyetherimide Polymers 0.000 description 13
- 239000000725 suspension Substances 0.000 description 12
- 125000003277 amino group Chemical group 0.000 description 11
- KFZMGEQAYNKOFK-UHFFFAOYSA-N iso-propanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 9
- 239000007788 liquid Substances 0.000 description 8
- 239000000758 substrate Substances 0.000 description 8
- 229920001730 Moisture cure polyurethane Polymers 0.000 description 6
- 239000004743 Polypropylene Substances 0.000 description 6
- SQGYOTSLMSWVJD-UHFFFAOYSA-N Silver nitrate Chemical compound [Ag+].[O-]N(=O)=O SQGYOTSLMSWVJD-UHFFFAOYSA-N 0.000 description 6
- 239000010408 film Substances 0.000 description 6
- 239000003973 paint Substances 0.000 description 6
- 239000004753 textile Substances 0.000 description 6
- 125000000129 anionic group Chemical group 0.000 description 5
- 239000000969 carrier Substances 0.000 description 5
- 239000010410 layer Substances 0.000 description 5
- 239000002245 particle Substances 0.000 description 5
- FYGDTMLNYKFZSV-CSHPIKHBSA-N β-cellotriose Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@@H](O[C@@H]2[C@H](O[C@@H](O)[C@H](O)[C@H]2O)CO)[C@H](O)[C@H]1O FYGDTMLNYKFZSV-CSHPIKHBSA-N 0.000 description 5
- 235000019749 Dry matter Nutrition 0.000 description 4
- 239000000853 adhesive Substances 0.000 description 4
- 230000001070 adhesive Effects 0.000 description 4
- 239000007864 aqueous solution Substances 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-M chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 4
- 238000010790 dilution Methods 0.000 description 4
- 201000009910 diseases by infectious agent Diseases 0.000 description 4
- 230000003993 interaction Effects 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- FOIXSVOLVBLSDH-UHFFFAOYSA-N silver ion Chemical compound [Ag+] FOIXSVOLVBLSDH-UHFFFAOYSA-N 0.000 description 4
- 239000010457 zeolite Substances 0.000 description 4
- OEBRKCOSUFCWJD-UHFFFAOYSA-N Dichlorvos Chemical compound COP(=O)(OC)OC=C(Cl)Cl OEBRKCOSUFCWJD-UHFFFAOYSA-N 0.000 description 3
- 239000004593 Epoxy Substances 0.000 description 3
- 241000191967 Staphylococcus aureus Species 0.000 description 3
- 229940076185 Staphylococcus aureus Drugs 0.000 description 3
- 230000001476 alcoholic Effects 0.000 description 3
- 230000000875 corresponding Effects 0.000 description 3
- 239000002537 cosmetic Substances 0.000 description 3
- 239000006185 dispersion Substances 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 125000003700 epoxy group Chemical group 0.000 description 3
- 230000001747 exhibiting Effects 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 230000003287 optical Effects 0.000 description 3
- 229920000915 polyvinyl chloride Polymers 0.000 description 3
- 229910001961 silver nitrate Inorganic materials 0.000 description 3
- RZTYEUCBTNJJIW-UHFFFAOYSA-K silver;zirconium(4+);phosphate Chemical compound [Zr+4].[Ag+].[O-]P([O-])([O-])=O RZTYEUCBTNJJIW-UHFFFAOYSA-K 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 239000004094 surface-active agent Substances 0.000 description 3
- 206010053317 Hydrophobia Diseases 0.000 description 2
- QEEAPRPFLLJWCF-UHFFFAOYSA-K Potassium citrate Chemical compound [K+].[K+].[K+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O QEEAPRPFLLJWCF-UHFFFAOYSA-K 0.000 description 2
- 229940054334 SILVER CATION Drugs 0.000 description 2
- NDVLTYZPCACLMA-UHFFFAOYSA-N Silver oxide Chemical compound [O-2].[Ag+].[Ag+] NDVLTYZPCACLMA-UHFFFAOYSA-N 0.000 description 2
- IQPQWNKOIGAROB-UHFFFAOYSA-N [N-]=C=O Chemical compound [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 230000002378 acidificating Effects 0.000 description 2
- 229940027985 antiseptics and disinfectants Silver compounds Drugs 0.000 description 2
- 230000003115 biocidal Effects 0.000 description 2
- 150000001735 carboxylic acids Chemical class 0.000 description 2
- 150000001768 cations Chemical class 0.000 description 2
- 239000012141 concentrate Substances 0.000 description 2
- 230000003750 conditioning Effects 0.000 description 2
- 238000007865 diluting Methods 0.000 description 2
- 238000002845 discoloration Methods 0.000 description 2
- 125000000524 functional group Chemical group 0.000 description 2
- 239000000499 gel Substances 0.000 description 2
- 229910001504 inorganic chloride Inorganic materials 0.000 description 2
- 239000000314 lubricant Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 150000002894 organic compounds Chemical class 0.000 description 2
- 238000005498 polishing Methods 0.000 description 2
- 239000001508 potassium citrate Substances 0.000 description 2
- 229960002635 potassium citrate Drugs 0.000 description 2
- 238000003825 pressing Methods 0.000 description 2
- 238000011012 sanitization Methods 0.000 description 2
- 150000003378 silver Chemical class 0.000 description 2
- 229940100890 silver compounds Drugs 0.000 description 2
- AYGJDUHQRFKLBG-UHFFFAOYSA-M sodium;1,1-dioxo-1,2-benzothiazol-3-olate;dihydrate Chemical compound O.O.[Na+].C1=CC=C2C(=O)[N-]S(=O)(=O)C2=C1 AYGJDUHQRFKLBG-UHFFFAOYSA-M 0.000 description 2
- 238000004381 surface treatment Methods 0.000 description 2
- 210000001519 tissues Anatomy 0.000 description 2
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
- 239000011791 tripotassium citrate Substances 0.000 description 2
- 235000015870 tripotassium citrate Nutrition 0.000 description 2
- IWDUDCDZGOLTTJ-UHFFFAOYSA-N 1H-imidazole;silver Chemical compound [Ag].C1=CNC=N1 IWDUDCDZGOLTTJ-UHFFFAOYSA-N 0.000 description 1
- KRKNYBCHXYNGOX-UHFFFAOYSA-K 2qpq Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 description 1
- 235000002723 Dioscorea alata Nutrition 0.000 description 1
- 235000007056 Dioscorea composita Nutrition 0.000 description 1
- 235000009723 Dioscorea convolvulacea Nutrition 0.000 description 1
- 235000005362 Dioscorea floribunda Nutrition 0.000 description 1
- 235000004868 Dioscorea macrostachya Nutrition 0.000 description 1
- 235000005361 Dioscorea nummularia Nutrition 0.000 description 1
- 235000005360 Dioscorea spiculiflora Nutrition 0.000 description 1
- 240000005760 Dioscorea villosa Species 0.000 description 1
- SZXQTJUDPRGNJN-UHFFFAOYSA-N Dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- RJQXTJLFIWVMTO-TYNCELHUSA-N Methicillin Chemical compound COC1=CC=CC(OC)=C1C(=O)N[C@@H]1C(=O)N2[C@@H](C(O)=O)C(C)(C)S[C@@H]21 RJQXTJLFIWVMTO-TYNCELHUSA-N 0.000 description 1
- 239000004677 Nylon Substances 0.000 description 1
- 229920001228 Polyisocyanate Polymers 0.000 description 1
- CQLFBEKRDQMJLZ-UHFFFAOYSA-M Silver acetate Chemical compound [Ag+].CC([O-])=O CQLFBEKRDQMJLZ-UHFFFAOYSA-M 0.000 description 1
- UEJSSZHHYBHCEL-UHFFFAOYSA-N Silver sulfadiazine Chemical compound [Ag+].C1=CC(N)=CC=C1S(=O)(=O)[N-]C1=NC=CC=N1 UEJSSZHHYBHCEL-UHFFFAOYSA-N 0.000 description 1
- 229910000831 Steel Inorganic materials 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- 150000001413 amino acids Chemical class 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- 150000003868 ammonium compounds Chemical class 0.000 description 1
- 239000003242 anti bacterial agent Substances 0.000 description 1
- 235000006350 apichu Nutrition 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 239000008122 artificial sweetener Substances 0.000 description 1
- 230000001580 bacterial Effects 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 230000000975 bioactive Effects 0.000 description 1
- 239000003139 biocide Substances 0.000 description 1
- 101710023077 blaNDM-1 Proteins 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 238000004364 calculation method Methods 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 125000004432 carbon atoms Chemical group C* 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000012459 cleaning agent Substances 0.000 description 1
- 239000011247 coating layer Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 230000000295 complement Effects 0.000 description 1
- 230000001276 controlling effect Effects 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 239000008367 deionised water Substances 0.000 description 1
- 239000000645 desinfectant Substances 0.000 description 1
- 150000004683 dihydrates Chemical class 0.000 description 1
- 235000004879 dioscorea Nutrition 0.000 description 1
- 238000003618 dip coating Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 239000003822 epoxy resin Substances 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 239000003063 flame retardant Substances 0.000 description 1
- 238000005187 foaming Methods 0.000 description 1
- 150000002430 hydrocarbons Chemical group 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 230000001939 inductive effect Effects 0.000 description 1
- 229920000831 ionic polymer Polymers 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-M methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 1
- 229960003085 meticillin Drugs 0.000 description 1
- 230000003641 microbiacidal Effects 0.000 description 1
- 230000002906 microbiologic Effects 0.000 description 1
- 230000005012 migration Effects 0.000 description 1
- 239000003607 modifier Substances 0.000 description 1
- 239000002105 nanoparticle Substances 0.000 description 1
- 239000010956 nickel silver Substances 0.000 description 1
- 125000004433 nitrogen atoms Chemical group N* 0.000 description 1
- 239000002736 nonionic surfactant Substances 0.000 description 1
- 229920001778 nylon Polymers 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 150000002898 organic sulfur compounds Chemical class 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 230000001590 oxidative Effects 0.000 description 1
- 238000010422 painting Methods 0.000 description 1
- 235000021317 phosphate Nutrition 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 229920002239 polyacrylonitrile Polymers 0.000 description 1
- 239000011528 polyamide (building material) Substances 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- 239000005056 polyisocyanate Substances 0.000 description 1
- 229920000098 polyolefin Polymers 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- WBZFUFAFFUEMEI-UHFFFAOYSA-M potassium;6-methyl-2,2-dioxooxathiazin-4-olate Chemical compound [K+].CC1=CC(=O)[N-]S(=O)(=O)O1 WBZFUFAFFUEMEI-UHFFFAOYSA-M 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 230000001737 promoting Effects 0.000 description 1
- DNIAPMSPPWPWGF-UHFFFAOYSA-N propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 1
- 238000004445 quantitative analysis Methods 0.000 description 1
- 239000002964 rayon Substances 0.000 description 1
- 238000006479 redox reaction Methods 0.000 description 1
- 230000001105 regulatory Effects 0.000 description 1
- 230000002940 repellent Effects 0.000 description 1
- 239000005871 repellent Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000004826 seaming Methods 0.000 description 1
- 239000002453 shampoo Substances 0.000 description 1
- BLRPTPMANUNPDV-UHFFFAOYSA-N silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 1
- 229910000077 silane Inorganic materials 0.000 description 1
- 150000004756 silanes Chemical class 0.000 description 1
- 229940071536 silver acetate Drugs 0.000 description 1
- 229940071575 silver citrate Drugs 0.000 description 1
- 229910001923 silver oxide Inorganic materials 0.000 description 1
- 229960003600 silver sulfadiazine Drugs 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 238000003892 spreading Methods 0.000 description 1
- 238000011105 stabilization Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 239000011550 stock solution Substances 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- 239000008399 tap water Substances 0.000 description 1
- 235000020679 tap water Nutrition 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- RTAQQCXQSZGOHL-UHFFFAOYSA-N titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- 239000000606 toothpaste Substances 0.000 description 1
- 230000000699 topical Effects 0.000 description 1
- 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 description 1
- 238000004148 unit process Methods 0.000 description 1
- 229920003169 water-soluble polymer Polymers 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- 239000012224 working solution Substances 0.000 description 1
Abstract
The invention concerns a polymeric antimicrobial composition, a method of producing the same and the uses thereof. The ionomer composition comprises an amine functional polymer compound reacted with silver halide, optionally together with a stabilizing component, such as an organic substance carrying a sulfonamide functional group. The ionomer composition can be obtained by reacting together (i) at least one polyamine and silver halide and optionally at least one organic stabilizer substance or; (ii) at least one polyamine, at least one nonhalide silver salt or silver complex, hydrogen halide and/or alkaline metal halide salt and optionally at least one organic stabilizer substance. The present ionomer composition is suitable for use as an antimicrobial coating, antimicrobial finish, antimicrobial additive and as antimicrobial component for formation of new antimicrobial materials.
Description
The présent invention relates to polymeric antimicrobial compositions. In partîcular the invention concems novel antimicrobial ionomer compositions, methods of preparing the same and the uses thereof.
Description of Related Art
Antimicrobial technologies based on the bioactive properties of ionic silver are currently wîdely rccognizcd as bclonging to the most advaneed solutions on the wide application 15 field of antimicrobial materials both in the science community and the industries utilizing antimicrobial surface technologies. Ionie silver has a general status as a safe biocide in many applications. Also the wide antimicrobial spectrum of silver against most bacterial species, including the antibiotic résistant straîns, e.g. MRSA and NDM-1 which currently generate a severe health treat to patients in the form of hospital infections, makes ionic 20 silver particularly interesting.
Recently in the healthcare scctor, strategies for improving hospital hygiene and preventing infections hâve been extendcd to cover the aspect of spreading of infections through various surfaces in the healthcare environments. Correspondingly the application of 25 antimicrobial materials and coating technologies hâve been emphasized as a new complementary mean for together with other aspects contributing to the battle against hospital infections.
Multiple strategies hâve been utilized to form antimicrobially active, silver releasing 30 surfaces on fibers and bulk material surfaces. Conventional strategies typically comprise attachment on the surfaces of silver containing particles, such as nanosilver, silver zcolite, silver zirconium phosphate and silver chloride containing titanium dioxide particles, by various chemical means, typically utilizing a carrier material. Another conventional method is to treat certain surface materials chemically in order to provide attachment of silver ions or silver containing particles on the surface.
Nanoparticulate silver (nanosilver) has rccently been extensively studied emerged as a potentially hazardous material to hcalth and environment, which again has increased pressure towards developing of new silver ion technologies
Liquid antîmicrobial additives for liquid products, such as disinfection solutions, surfactants, paints, wax/polymer coatings, deodorizing solutions and cosmctic solutions, are typically based on utilization of silver citrate solutions or silver zeolite or particulate silver dispersions, colloïdal silver.
To date, polymer carrier based silver technologies hâve not been studied or developed extensively. Technologies based on functional ionic polymers are rare.
International Published Patent Application W02002/030204 discloses novel antibacterial agents, wherein the lone pair électrons of nitrogen atoms of amine compounds with high boiling point or water-soluble polymer with basic nitrogen at the backbone or side chain are coordinated with silver ion. Antibacterial and deodorizing solution comprising them are 20 also disclosed.
US Published Patent Application No. 2009246258 discloses antîmicrobial and odor adsorbing fabric substrate having a surface coating. The coating contains silver compounds and combination thereof, a hyperbranchcd polyethyleneimine dérivative, potassium citrate, 25 inorganic chloride, a polyuréthane binder, and a cross-linking agent. The silver compounds are selected from the group consisting of silver zirconium phosphate, silver zeolite, silver glass, and any mixtures thereof or a conductive silver containing nanoparticles. ioncxchange resins, zeolites, or, possibly substituted glass compounds.
According to the publication hyperbranchcd polyethyleneimine derivative, abbreviated “hPEI”, comprises at least one hyperbranchcd polyethyleneimine linked to one or more linear hydrocarbon groups having 5 to 30 carbons. The preferred silver containing compounds are silver zirconium phosphate available from Milliken & Company under the trade name ALPHASAN, silver zeolite available from Sinanen under the trade name ZEOMIC, and silver glass available from Ishizuka Glass under the trade name IONPURE. Inorganic chlorides are preferred, cspecially magnésium chloride and ammonium chloride. A range of ratios from 1:10 to 5:1 (chloride to silver ion). The h-PEI dérivatives also suffered from discoloration and it was found that potassium citrate reduced or eliminated the yellowîng ofthe h-PEI.
Summary of the Invention
The présent invention aims at providing an antimicrobial ionomer composition, which comprises an amine functional cationic polymer and silver halide.
According to the invention, an antimicrobial amorphous ionomer composition can be obtained by a process comprising reacting at least one amine functional polymer and a silver halide. Altcmately, the composition can be obtained by a process comprising reacting a amine functional polymer and at least one silver non-halidc sait or complex compound and hydrogen halide or an alkali métal or alkaline earth métal or ammonium halide sait.
Thus, in a first preferred embodiment the antimicrobial ionomer composition is obtained by reacting together in a solvent matrix
- at least onc polymer exhibiting functional amine groups, and
- a silver halide.
In another preferred embodiment, the présent antimicrobial ionomer composition is obtained by reacting together in a solvent matrix
- at least onc polymer exhibiting functional amine groups,
- at least onc organic silver sait or complex compound and
- hydrogen halide, an alkali métal or alkaline earth métal halide sait or ammonium halide sait, or a combination thereof.
In further preferred embodiments, the présent antimicrobial ionomer composition is further balanced and controlled by including stabilizing components in the composition. In further preferred embodiments, the stabilizing components comprise a sulfonamide group
containing organic substancc(s). In some embodiments, said stabilizer substance may be the counter-anion or ligand of said at least one organic silver sait or complex compound.
In some embodiments, said antimicrobial composition includes additional components, such as cross-linking agents, hydrophobie modificrs, water rcpcllents, various stabilizers and surfactants.
The préparation methods disclosed above can also be combined.
The antimicrobial ionomer composition according to the invention can be used for coating and treating a grcat varicty of host surfaces.
More specifically, the présent ionomer compositions arc mainly characterized by what is stated in the characterizing part of claim l.
The method according to the présent invention is characterized by what is stated in the characterizing part of claim 25.
The use of the ionomer compositions is characterized by what is stated in claim 31.
The invention provides considérable advantages. Generally, the novel composition is suitable for use as an antimicrobial coating, antimicrobial and sanitizing finish, antimicrobial additive and as antimicrobial component for formation of new antimicrobial materials.
The novel antimicrobial ionomer compositions are particularly useful for coating of various substrates, such as fibcr, fabric and bulk material surfaces, including various synthetic, semisynthetic and natural fïbers, woven fabrics, nonwoven fabrics, knitted fabrics, papers, various polymer surfaces, métal surfaces, various coating surfaces, wood 30 surfaces and fïbers. The novel antimicrobial ionomer compositions are particularly useful for antimicrobial wet wipes, hand sanitizer liquids and cosmctics.
The ionomer composition according to the présent invention provides an enhaneed antimicrobial effect, optical performance and stability which surpasses that of known antibacterial compositions comprising different silver sources mixed with polyamine polymers. It appears that halide carrying ionomers of polyamine and silver provide enhanced adhesion properties, antimicrobial activity, control of silver-ion release and optical performance. The ionomer composition according to the présent invention is 5 preferably free of particles.
Next the invention will be examined more closely with the aid of a detailed description and with reference to a number of working examplcs,
Detailed Description of Preferred Embodiments
The présent invention discloses novei antimicrobial compositions comprising ionomers of amine functional polymers (i.e. polymers exhibiting functional amine groups) and métal halides. According to a preferred embodiment of the ionomer composition according to the 15 invention, the composition is produced in - and it therefore also comprises - a solvent matrix, preferably comprising alcohols, such as methyl alcohol or ethyl alcohol, isopropyl alcohol or water and combinations thereof.
In a first preferred embodiment, the ionomer compositions are obtained by reacting together at least one amine functional polymer (ionomer prepolymer, carrier polymer) and silver halide. In another preferred embodiment the ionomer compositions arc obtained by reacting together at least one amine functional polymer (ionomer prepolymer, carrier polymer), at least one non-halide silver sait or complex compound and hydrogen halide and/or alkali métal or alkaline earth métal (in the following jointly designated “alkaline métal”) halide sait.
In one embodiment, an amine functional polymer “carrier” polymer is reacted together with either silver halide or a silver sait or complex compound, however in the latter case the composition is halidized with either hydrogen halide or alkaline métal halide sait (“halide compound”) in order to obtain the composition characteristic to the invention. In a preferred embodiment, at least one stabilizer component/substance is included in the system (composition). With both routes the obtained product possesses similar essential properties independent of variations in the proton or alkaline métal cation or alkaline métal sait concentrations.
Z
In a preferred embodiment of the invention, said amine functional ionomcr prcpolymer comprises a branched polyethyleneimine, a linear polyethyleneimine or a mixture of corresponding polycthyleneimines of different qualities with different properties with regard to e.g. molecular weights and primary:sccondary:tertiary -amine ratios. Also copolymers of polycthyleneimines are useful.
In other embodiments said amine functional polymer comprises other linear or branched polyamines, such as polyvinylamine, polyacrylamine, polyarylamine, polyethyleneimine, 10 polyhexamethylene-biguanidine and polyvinylpyridine. Combinations of various amine functional polymers may be applied for obtaining the antimicrobial ionomer compositions characteristic to the invention.
The amine functional polymer preferably comprises or consists of or consists essentially of 15 a potentially branched polyethyleneimine having a molecular weight (Mw) between 200 and 3,000,000, in particular about 750 to 2,000,000.
As further examples, the following embodiments can be mentioned:
- compositions wherein the amine functional polymer is polyvinylamine or copolymer having 30-100 mol-% of vinylamine, in particular embodiments wherein the amine functional polymer is graft polymer of polyvinylamine with ethylcncimine;
- compositions wherein the amine functional polymer is a graft polymer of polyamidoamïne with ethylencimine;
- compositions wherein the amine functional polymer is a polyarylamine copolymer;
and
- compositions wherein the amine functional polymer is polyacrylamine.
Compositions wherein the polymer components arc intcmally cross-linkcd through at least 30 one cross-linking agent arc also contemplated.
In some embodiments, said stabilizer component comprises one or more organic or inorganic substances capable of promoting the stability of silver moicties within the composition against various stressors, such as UV radiation, heat, moisture, redox reactions, pH and other factors which may cause unfavorable changes to the compositions in accordance with the invention. The unfavorable effects include discoloration, particle formation and other unfavorable effects in the esscntial chemical structure of the compositions and correspondingly e.g. in the state appearance of the composition.
In one preferred embodiment of the invention, said stabilizer comprises at least one substance or compound carrying sulfonamîde functional group(s).
In another preferred embodiment, said stabilizer comprises ammonium cations.
In another preferred embodiment, said stabilizer comprises excess chloride anions.
In another preferred embodiment, said stabilizer substance or combination of stabilizer substances is selected from the group comprising saccharin, cyclamic acid, sulfadîazine, 15 accsulfame, ammonium chloride and ammonium saccharin.
In a particularly preferred embodiment said stabilizer substance comprises saccharin.
In some embodiments said stabilizer substance may comprise e.g. organic acids (such as carboxylic acids, sulfonic acids and amino acids), quartemary ammonium compounds, phosphates, esters, aldéhydes, ketones, zwittcrionic compounds, titanates and their organic dérivatives, silanes and their organic dérivatives and organosulphur compounds.
Saccharin (o-sulfobenzimide; l,2-bcnzothiazolc-3(2H)-one 1,1-dioxide) is onc of the most widely used artificial sweetening agents. The imino hydrogen of saccharin is acidic. The molécule can casily be converted into the corresponding nitranion. The coordination chemistry of the saccharinato anion is very versatile. It offers multiple coordination sites to mctallic ccntcrs.
A typical silver compound, silver saccharinate (usual form: silver saccharinatc dihydrate) is a solid white powder with limited solubility propertics. Silver saccharin may typically be produced through précipitation by reacting acidic form saccharin and silver nitrate, or from sodium saccharin and silver nitrate in certain solvent compositions depending on the molecular state of saccharin.
In some embodiments, the free amine functional groups of said amine functional polymer, which in a preferred embodiment comprises polyethyleneimine, have a function in attachment of said composition to host materials (materials wherein the ionomer composition of the invention is added to provide antimicrobial functionality) and material surfaces (surfaces coated with material comprising the ionomer composition of the invention). When used as an additive, attachment to host matcrial/host matrix may be achieved through adhesion, e.g. ionic bonding or covalent bonding, between amine groups of the amine functional polymer backbone part of the ionomer composition according to the invention and a molecular structure of a second material or interactions the like.
In one preferred embodiment the solvent matrix comprises ethyl alcohol or methyl alcohol or isopropanol or water or combinations thereof. Mixtures of solvents may be used, such as aqueous alcoholic solutions/mixtures. Said antimicrobial ionomer composition can be extracted from said solvent matrix for further use e.g. through evaporating the solvent. Typically a more practical and economical solution is, however, to design further processes for using the composition directly with a solvent matrix containing the ionomer composition as a starting material.
According to another embodiment of the invention, the silvcr cation is delivered into the ionomer composition as a non-halidc silver sait or silvcr complex, which reacts with amine functional polymer(s), in a preferred embodiment polyethyleneimine, followed by chloridization of the composition with hydrogen halide or alkaline métal halide sait or combinations thereof. In association with the latter embodiment, suitable non-halide silvcr salts or silver complexes include e.g. silver nitrate, silver acetate, silver stéarate, silver oxide, silver saccharinatc, silver imidazole, silvcr citrate, silvcr méthacrylate and silver sulfadiazine. In some embodiments, the chemical properties of the counter-ions (anions) of the spécifie silver salts are utilîzed in stabilization of the composition and in controlling the migration of silver ions from the composition.
The silver content of the ionomer composition is about 0.001 to 50 %, in particular about 0.01 to 30 %, preferably about from 1 or 1.5 up to 25 % by weight of the total dry weight of the composition. The dry weight in this case is defined as the total weight of the composition when the mass of the solvent matrix is cxcluded from the calculation.
In a preferred embodiment, the ionomer composition according to the invention is obtained by a process, which comprises the following steps:
First, an alcoholic or aqueous solution of polycthyleneimine (PE1) is provided. In some embodiments, the optimal ratio (w/w) between PEI and solvent ranges from 1:0.01 to 1:100, in particular from 1:0.5 to 1:5, depending on the desired amount ofthe ionic silver compound, which is to be fed into the solution in the next step. Also, the assessment of the optimal solvent ratio dépends on the molecular weight of polyethyleneimine to be used and 10 the viscosity of the solution. The reaction between PEI and solvent is typically exothermic.
In a preferred embodiment, the mixture is cooled to standard température or below (i.e. the mixture is cooled to 25 °C or less, typically however to a température above the melting point of the liquid part of the mixture).
Next a solid ionic silver source is fed into the solution and mixed. E.g. silver halide reacts with PEI solution while increase of viscosity indicates ionomer formation. Depending on silver content and PEI:solvent ratio, a transparent, yellowish or almost colorlcss silver ionomer composition is formed.
The silver content of the ionomer composition may be controlled by regulating the amount of the silver source reacted with the PEI-solution, in one embodiment silver chloride. Typically the silver compound is used at 0.1 to 10,000 parts by weight, preferably about 1 to 1,000 parts by weight, for example 10 to 100 parts by weight for each 100 parts by weight ofthe ionomer prepolymer. Thus, typically the weight ratio ofthe silver compound to the ionomer prepolymer is about 1:100 to 100:1, in particular 1-10:50-100.
Particularly preferred embodiments comprise rcacting together 70 to 99.99 parts by weight of ionomer prepolymer and 0.01 to 30 parts by weight of a silver halide or of a complex compound and hydrogen halide, or of alkaline métal or ammonium halide sait.
Optionally thcrcaftcr a stabilizer compound, in a preferred embodiment acid form saccharin and/or sodium saccharin and/or potassium acesulfame, is fcd into the composition. When mixed together with the ionomer solution formed by the PEI and silver chloride, said acid form saccharin or sodium saccharin solubilizes into the ionomer solution forming a stable ionomer composition. The stabilizer compound is used in amounts of l to 50 parts by weight for each 100 parts by weight of the combination of the silver compound with the polymer compound. Typically, the weight ratio between the silver compound and the stabilizer compound is about l : 10 to 10: l.
A preferred embodiment comprises rcacting together 50 to 98,99 parts by weight of ionomer prepolymer, 0.01 to 30 parts by weight of a silver compound, or combination of silver compound and a halide compound, as cxplained above, and l to 20 parts by weight of a stabilizer.
In another preferred embodiment, a solution of PEI and alcoholic or aqueous solution is first produced and cooled down as described previously. Thereafter solid silver saccharin is delivered into the polymer solution and mixed. Silver saccharin solubilizes into the PEI solution and forms a transparent, yellowish or almost colorless solution of silver ionomer complex. The silver content of the composition may be controlled e.g. through the amount of silver saccharin.
Thereafter, in a preferred embodiment, an aqueous solution of hydrochloric acid is supplied. In one preferred embodiment the molar amount of the chloride anion is équivalent to the molar amount of silver cations. When the solution of PEI and silver saccharin is chloridized, a momentary white précipitation can be observed suggesting that at least a part of the silver cation is prccipitatcd from the soluble PEI-silvcr complex by the chloride anion, however, the assumed silver chloride précipitation is quickly reacted further. The latter phenomenon also suggests that silver chloride has a tendcncy to form unique ionic bonds with the amine functional groups of polymers. However, this is only one possible explanation for the observed phenomenon and should not interpreted as in any way limiting on the scope of the invention.
The molccular structure of the silver cation source, typically a silver sait or complex, has naturally a rôle in production of silver ionomer, through the introduction of the corresponding counter-ion (anion) or ligand into the system and through the spécifie interactions with the ionomer composition.
An intercsting phcnomenon observed in association with the invention at hand is, that surprisingly, the presence of halide anions, in a preferred embodiment, chloride anions, in the amine functional silver ionomer produces an enhanced antimicrobial effect when compared to ionomers comprising solely a PEI having its amine groups reacted with silver 5 ions.
In a preferred embodiment, polyethyleneimines (PEIs) are applied as amine functional polymers in accordance with the invention. PEIs belong to the class of polyamines and cationic polymers having the highest cationic charges per weight. The structures of homopolymcric polyethyleneimines always follow the pattern: one amine nitrogen and two carbon groups.
In general, PEIs adhéré to various polar surfaces very effectively. Branched PEIs comprising cationic anchor points (amines) allow fixation of the molécules to various surfaces and substrates with exceptionally high adhesion. In some embodiments of the invention, the amine groups of the ionomer composition may be cross-linked to various surfaces. Resulting from the strong surface active character, the ionomer composition according to the invention can be applied as e.g. an additive in substrates and adhesives and as building blocks in a polymer matrix. Like amine functional polymers, the ionomer compositions according to the invention are soluble in polar solvents and miscible with e.g. water, ethyl alcohol and methyl alcohol at any concentration.
In some embodiments the properties of the ionomer composition according to the invention are controlled through chemically bonding the amine groups of the amine functional polymer according to the composition with various additive compounds and compositions suitable for a spécifie application of the ionomer composition. In some embodiments, the additives may include anionic, non-ionic and other non-covalently bonded compounds (such as non-ionic surfactants, conjugate bases of carboxylic acids, zwitterionic compounds etc.) or organic compounds (e.g. epoxy or isocyanate functionalizcd organic compounds) covalently bonded with the amine groups of the composition.
In some embodiments, the ionomer compositions according to the invention may bc crosslinked intcmally and/or to and/or within host surfaces, materials and compositions. In some embodiments, the applicable cross-linking agents include e.g. substances with isocyanate, epoxy, aziridine, titanate, silane and acrylatc functionalities.
The présent antimicrobial ionomer compositions, when supplied in a liquid matrix, hâve a dry matter concentration of 0.0001 to 99 % by weight, in particular about 0.001 to 90 % by weight, advantageously 0.01 to 75 % be weight, calculated from the total weight of the composition. As the below working cxamplcs show, the compositions can readily be manufactured to a dry matter content of about 0.1 to 50 % by weight of the total weight of the composition. Such compositions can be concentrated or, usually diluted with further liquid, for the intended applications.
Based on the above, in a first embodiment a composition according to the présent invention comprises, or alternatively consists of, 70 to 99.99 % (by weight) of polymer and 0.01 to 30 % (by weight) of a silver compound, such as a silver sait, in particular silver halide, for example AgCl. The percentages are calculated from the total weight of the dry matter of the composition. Typically, said composition is free from stabilizing compounds.
In a second embodiment, a composition according to the présent invention comprises, or alternatively consists of, 50 to 98,99 % (by weight) of polymer, 0.01 to 30 % (by weight) of a silver compound, such as a silver sait, in particular silver halogenide, for example
AgCl, and 1 to 20 % (by weight) of a stabilizer. The percentages are calculated from the total weight of the dry matter of the composition (i.e. w/w).
The latter composition is particularly suitable as a concentrate which can be diluted into a liquid, such as an alcohol, typically an aliphatic alcohol having 1 to 6 carbon atoms.
When a composition, for example a concentrate produced in alcohol, is diluted in water, further stabilizer may be added. Generally, the total concentration of stabilizers in aqueous phase can be up to 95 % w/w. An cxamplc of a particularly suitable additional stabilizer is 30 ammonium chloride.
Through the adhesive charactcr of the ionomer composition according to the invention at hand, the composition functions well as thin films and monomolecular layers. Retricved from the properties of PEIs, l mg of the ionomer composition according to the invention may cover an area of close to 2 m2 of a nonporous surface with a monomolecular layer.
Generally, the applied amount of the présent ionomer composition will be dépendent on the aimed concentration of silver on the host surface. Typically, a silver concentration of about 0.001 to 10 % of the total weight of the coating layer on the substrate is sufficient.
The ionomer compositions according to the invention are directly compatible with cationic or nonionic Systems. The PEI-backbone with cationic amine groups may break down anionic dispersions or naturally depending on the chemical environment, produce modified dispersions or émulsions containing the composition according to the invention. Anionic surfaces adhère strongly to the composition due to ionic charges. In some embodiments, anionic or nonionic additives may be incorporated into the composition according to the invention for cnhancing and improving compatibility of the ionomer composition with e.g.
anionic Systems.
In some embodiments, said antimicrobial ionomer composition according to the invention is applied as such or as including additional components, such as cross-linking agents, hydrophobie modifiers, water repellcnts, various stabilizers and surfactants, for coating of 20 host surfaces such as fiber, fabric and bulk material surfaces, including various synthetic scmisynthetic and natural fibers, woven fabrics, nonwovcn fabrics, knitted fabrics, papers, various polymer surfaces, steel surfaces, various coating surfaces, wood surfaces and fiber, fabric and bulk material surfaces the like with the composition according to the invention.
In some embodiments, the ionomer compositions according to the invention adhéré to a large varicty of surfaces very cffcctively because of the cationic character of the PEIbackbone of the ionomer composition can bc used for coating purposcs of various substrates. Good adhesion is achicved to, for example, cellulosic products (e.g. cellulose, rayon and viscose), proteins, polyesters, polyamides, chlorine cont. polymers, silicates, silicium dioxide, iron, pigments, paper, wood, cotton, plants, skin, hair, films and fibers. Smooth polyolefin surfaces (PE, PP etc.) may be pretreated to bind certain substrates like coatings, adhesives or polymer films. An effective pretreatment is an oxidative treatment, which produces an cxceptionally strong adhesion.
Coating can be achieved through e.g. roll coating, spray coating or bath coating or processes the like. The ionomer composition can be diluted in e.g. alcohols or water or combinations thereof or in other suitable solvent compositions to obtain optimal solutions of the ionomer composition according to the invention in relation to the process in question 5 and required thickness of the ionomer composition according to the invention. Substances assïstîng the attachment of said ionomer composition according to the invention to surfaces, e.g. cross-linking agents, primer agents or substances the like can be incorporated to the composition. Said assisting substances may be used e.g. as included in the solvent system. In some embodiment said host surfaces may be treated chemically to assist the attachment of the ionomer composition according to the invention, e.g. through oxidation, attachment of substrate/primer layers and methods the like. In some embodiments the ionomer composition of the invention may be covalently cross-linked to and on host surfaces.
Generally, after dilution, the silver concentration of the diluted composition is from 1/5 to 1/1000 parts by weight of that of the original composition.
In some other embodiments, the antimicrobial ionomer composition according to the invention is used as an antimicrobial additive in various liquid product matrixes (host materials) compatible with said antimicrobial ionomer composition. The antimicrobial ionomer composition according to the invention can be added into said host materials e.g. during a suitable unit process in association with their production processes, or as a fînishing step, naturally depending on the material and process. According to the invention, new antimicrobial materials may be formed through the interaction of the antimicrobial ionomer composition according to the invention (when used as an antimicrobial additive) and said host material. In some embodiments said ionomer composition according to the invention is used as an additive for liquid product matrixes or intermediate product matrixes to form new antimicrobial materials and products.
The “liquid product matrixes” in this context mean any liquid product or intermediate product regardless of its use, its interaction with said antimicrobial additive composition and the final state of matter after usage. In some embodiments the ionomer composition of the invention may be cross-linked with the components of the host matrix. Some exemplifying applications wherein said ionomer composition according to the invention can be used as an antimicrobial additive and/or component for formation of new antimicrobial materials include the following: détergents (e.g. cosmetic/hygienic détergents, shower gels, shampoos and industrial détergents), paints, vamishes, floor conditioners/polishes, adhesives, gelcoats, epoxy materials, polyuréthanes, cosmetic products, disinfection substances (e.g. disinfection hand gels, hospital, public space and consumer applications, medical devices, liquide for moîst wipes), seaming materials, médicinal products, toothpastes and applications the like.
The examples presented in the following are not meant to limit the scope of the invention.
Example 1
An antimicrobial composition according to the invention was produced in a solvent matrix. 2.0 grams of a branched polycthyleneimine (Lupasol WF, BASF, MW 25 000) was solubiüzed in 8 grams of ethyl alcohol and cooled down. The solution was reacted together with 0.295 grams of silver chloride by mixing said suspension at room température until a clear solution was formed. The obtained ionomer composition had a dry content (mass of the solvent excluded) of 22.3 % (w/w) and theoretical silver content of 9.7 % (w/w) of dry mass.
Example 2
An antimicrobial ionomer composition according to the invention was produced in a solvent matrix. Approximately 2.0 g of a branched polyethyleneimîne (Lupasol G20 waterfree, BASF, molecular weight 1300) was mixed with 6 g of ethyl alcohol and cooled down. The solution was reacted with 0.724 g of silver saccharinatc by mixing said suspension at room température until a clear solution was formed. The process was continued by adding 2.49 ml of 1 M hydrochloric acid into said solution under continuous mixing. A clear solution ofan optically clear ionomer composition was formed, having a dry content (w/w) of 25.0 % and theoretical silver content of 9.5 % (w/w) of dry mass.
Example 3
An antîmicrobial ionomer composition according to the invention was produced in a solvent matrix. 1.0 grams of a branchcd polycthyleneimine (Lupasol G20 watcrfrce, BASF, molecular weight 1300) was solubilizcd to 3 grams of ethyl alcohol and cooled down. The solution was reacted together with 0.156 grams of silver saccharinate by mixing said suspension at room température until a clear solution was formed. The process was continued by diluting the intermediate composition to a total volume of 50 ml with EtOH. Finally, the product was chloridizcd by adding 0.570 ml of 1 M HCl under mixing conditions.
Comparison example 4
An antîmicrobial composition was produced in a solvent matrix. 1.0 grams of a branchcd polycthyleneimine (Lupasol G20 waterfree, BASF, molecular weight 1300) was solubilized to 3 grams of ethyl alcohol and cooled down. The solution was reacted together with 0.156 grams of silver saccharinate by mixing said suspension at room température until a clear solution was formed. The product was diluted to a total volume of 50.570 ml with EtOH.
Example 5
An antîmicrobial ionomer composition according to the invention was produced in a solvent matrix. 3.0 grams of a branchcd polycthyleneimine (Lupasol PS, BASF, molecular weight 750,000, concentration in water 33%) was mixed with 1 grams of ethyl alcohol and cooled down. The solution was reacted together with 0.156 grams of silver saccharinate by mixing said suspension at room température until a clear solution was formed. The intermediate composition was diluted to a total volume of 50 ml with EtOH. Finally, the composition was chloridizcd by adding 0.570 ml of 1 M HCl under mixing conditions.
Comparison example 6
An antimicrobial composition was produced in a solvent matrix. 3.0 grams of a branched polyethyleneimine (Lupasol PS, BASF, molecular weight 750,000, concentration in water
33%) was mixed with 1 grams of ethyl alcohol and cooled down. The solution was reacted together with 0.156 grams of silver saccharinate by mixing said suspension at room température until a clear solution was formed. The product was diluted to a total volume of 50.570 ml with ethyl alcohol.
Application Example 7
The antimicrobial ionomer composition according to the invention produced as described in Example 2 was applied as an antimicrobial additive for an acrylic interior paint (Tikkurila Harmony, white, determined dry mass 88 % w/w). Two test batches were prepared by mixing the composition according to Example 2 and the paint in mixing ratios of 1:10 and 1:20, respectively. The resulting theoretical silver contents (% of dry weight) were correspondingly about 0.3 % and 0.14 %.
For both samples, test surfaces were prepared by painting two surfaces of a PVC film with 20 the sample compositions and the allowed to dry at standard température for 48 hours. The antimicrobial efïîcacy of the paint surfaces against Methicillin Résistant Staphylococclus Aureus (MRSA) were determined following standard ISO 22196. As a resuit for the two paint surfaces, a réduction of >41og for MRSA was achieved.
Application Example 8
The antimicrobial ionomer composition according to the invention produced as described in Example 2 was applied as an antimicrobial additive for a waxed floor conditioning and polishing agent (Johnson Diversey, Jontec, determined dry mass 28.6 % w/w). A test batch 30 was prepared by mixing the ionomer composition according to Examplc 2 and the floor conditioning and polishing agent in a mixing ratio of 1:10 resulting in theoretical silver content (% of dry weight) of 0.84 %. A test surface was prepared. A working solution was prepared by further diluting the test batch with tap water in a ratio of 1:20 (composition according to exampie 2: Jontcc). The dilution was spread on a PVC film and let dry for 48 hours leaving a faint colorlcss dry material film on the surface. The antimicrobial cfficacy of the conditioncd surface against Mcthicillin Résistant Staphylococclus aureus (MRSA) was determined following standard ISO 22196. As a resuit for the surface treated with the diluted floor conditioner dopcd with the antimicrobial composition according to the invention, a réduction of >4log for MRSA was achieved.
Application Example 9
The antimicrobial ionomer composition according to the invention produced in examples 3 and 5 and the compositions produced in comparative cxamples 4 and 6 were applied as an antimicrobial coating/ antimicrobial finish for knitted fabric. Four sample pièces (2,5x15 cm2) of a polyester-cotton blond (65%-35%) medical scrub fabrics were treated with the compositions obtained in cxamples 3 (AE91, 4 (AE92), 5 (AE93) and 6 (AE94). The sample fabrics were immersed into the diluted solutions for 30 seconds. The immersed samples were let dry overnight at room température on paper tissues. The antimicrobial efficacy against Staphylococcus aureus (ATCC 6538) was tested following ISO 20645 standard. The results arc presented in Table 1.
Table 1
| Sample | Vinson's rating | Antimicrobial efficacy |
| AE91 | 4+(2mm) | Excellent |
| AE92 | 2 | Fair |
| AE93 | 4+(2mm) | Excellent |
| AE94 | 2 | Fair |
According to the results presented in Table 1, the antimicrobial efïîcacics of chloridized ionomer compositions, tumed out to bc higher compared to the compositions obtained through reacting solely PEI and silver saccharinate.
Application Example 10
A sériés of antimicrobial treatments was carried out for nonwovcn polypropylene (19.9 g/m2) fabric (4 samples, AE101-AE104) and polyester-cotton (65%-35%) blcnd (212.5 g/m2) medical scrub fabric (4 samples, AE105-AE108). An antimicrobial ionomer composition according to the invention was produced in a solvent matrix. 2.0 grams of a
branched polyethylcneiminc (Lupasol G20 waterfree, BASF, molecular weight 1300) was solubilized to 6.0 grams of ethyl alcohol and cooled down. The solution was reacted together with 0.3 grams of silver saccharinate by mixing said suspension at room température until a clear solution was formed. The process was continued by adding 1.140 ml of 1 M hydrochloric acid into said solution. A clear solution of an optically clear ionomer composition was formed, having a dry content (w/w) of 24.8 % and theoretical silver content of 4.7 % (w/w) of dry mass. A séries of baths containing antimicrobial ionomer compostition of the invention obtained previously were prepared. The bath compositions arc presented in Table 2.
Table 2
| Bath | Dilution (AM-comp.:EtOH) | AM-Comp. (g/1) | Ag (mg/1) |
| 1 | 1:20 | 11.50 | 541 |
| 2 | 1:50 | 4.60 | 216 |
| 3 | 1:100 | 2.30 | 108 |
| 4 | 1:200 | 1.15 | 54 |
The fabric samples were treated with the antimicrobial ionomer composition by immersing 15 thc sample fabrics into the diluted solutions. Immersed samples were let dry on paper tissues absorbing part ofthe excess liquid. Resultcd mass percentages of antimicrobial coatings and theoretical silver contents of the treated fabrics are listed in Table 3.
Table 3 ____________________________________________________________
| Sample/ Bath | Material | AM-Comp (%w/w) | Ag (mg/m2) |
| AE101/1 | nonwovcn PP | 6.20 | 54 |
| AE102/2 | nonwovcn PP | 3.26 | 26 |
| AE103/3 | nonwovcn PP | 0.83 | 8 |
| AE 104/4 | nonwovcn PP | 0.40 | 4 |
| AE 105/1 | cotton-PE blond | 1.55 | 155 |
| AE 106/2 | cotton-PE blend | 0.84 | 84 |
| AE 107/3 | cotton-PE blend | 0.39 | 39 |
| AE 108/4 | cotton-PE blend | 0.33 | 33 |
The antimicrobial efïïcacies of treated sample fabrics coated with the antimicrobial composition of the invention were tested against Staphylococcous aureus (ATCC 6538) following ISO 20743 -standard. Thc results arc presented in Table 4.
Table 4
| Antimicrobial | ||
| Sample | Vinson's rating | cfficacy |
| AE101 | 4 | Excellent |
| AE102 | 2 | Fair |
| AE103 | 2 | Fair |
| AE104 | 2 | Fair |
| AE105 | 4 (+2) | Excellent |
| AE106 | 4(+l) | Excellent |
| AE107 | 4 | Excellent |
| AE108 | 4 | Excellent |
It must bc noted that the applied microbiological test has limitations when tested with a very lightweight fabrics, such as CE IOl-104. By taking into account the limitations, very successful antimicrobial performances were achieved for all samples.
Example 11
An antimicrobial ionomer composition according to the invention was produced in a solvent matrix. 2.0 grams of a branched polyethyleneimine (Lupasol WF, BASF, MW 25,000) was solubilized in 8 grams of ethyl alcohol and cooled down. The solution was reactcd together with 0.295 grams of silver chloride by mixing said suspension at room température until a clear solution was formed. The process was continued by adding 0.378 grams of saccharin and mixing until a clear solution was formed.
Example 12
An antimicrobial ionomer composition according to the invention was produced in a solvent matrix. 2.0 grams of a branched polyethyleneimine (Lupasol P, BASF, MW 750,000, concentration in water 50 %) was mixed with 5.460 grams of ethyl alcohol and cooled down. The solution was reacted together with 0.345 grams of silver chloride by mixing said suspension at room température until a clear solution was formed. The process was continued by adding 0.5 grams of saccharin.
Example 13
An antîmicrobial ionomer composition according to the invention was produced in a solvent matrix. 160 grams of a branchcd polyethyleneimine (Lupasol WF, BASF, MW 25,000) was solubilizcd to 640 grams of ethyl alcohol and cooled down. The solution was reacted together with 23.64 grams of silver chloride by initially homogenizing said product with a high shear homogenizer for onc minute and further mixing said suspension at room température under agitation by a magnetic stirrer until a clear solution was formed. The process was continued by adding 35.21 grams of saccharin followed by mixing until a clear transparent composition was formed.
Example 14
An antîmicrobial ionomer composition according to the invention was produced in a solvent matrix. 2.1 grams of a branchcd polyethyleneimine (Lupasol WF, BASF, MW 25,000) was solubilized in 1000 ml of deionized water. The solution was reacted together with 0.3 grams of silver chloride, 0.16 grams of saccharin and 2 grams of ammonium chloride at room température resulting in a clear ionomer solution.
Example 15
An antîmicrobial ionomer composition according to the invention was produced in a solvent matrix. 4 grams of polyvinylamine (Catiofast GM, BASF) and 22.32 grams of a branched polyethyleneimine (Lupasol WF, BASF, MW 25 000) was solubilized in 80.86 grams of isopropanol and cooled down. The solution was reacted together with 3.88 grams of silver chloride by mixing said suspension at room température until a clear solution was formed. The process was continued by adding 2.08 grams of saccharin and mixing until a clear solution was formed.
Example 16
An antîmicrobial ionomer composition according to the invention was produced in a solvent matrix. 26.26 grams of a branchcd polyethyleneimine (Lupasol WF, BASF, MW
000) was solubilizcd in 80.86 grams of isopropanol. The solution was reactcd together with 3.88 grams of silver chloride by mixing said suspension at a constant température of 16 °C until a clear solution was formed. The process was continued by adding 2.08 grams of saccharin and mixing until a clear solution was formed.
Application example 17
An antimicrobial ionomer composition according to the invention may be applied as an antimicrobial finish/topical treatment/coating agent for various fibers and fiber products, including natural (e.g. cotton), semisynthetic (e.g. viscose) and synthetic (e.g. PET, PS, 10 nylon, polyamide, polyacrylonitrile etc.) fibers and fiber products as applied as such or in combination (as reacted or unreactcd), with various fiber/yam/textile treatment additives, modifïcrs, spin bath additives, finishes, lubricants, cross-linking agents, dyes, coating agents, flame retardant agents and the like. It is clear, that various material combinations used in combination with the antimicrobial ionomer composition produce varying properties to the finished fibers with respect to water solubility of the final finish composition on the fiber surfaces, silver release and correspondingly antimicrobial function.
In the cxample, an antimicrobial ionomer composition according to Example 16 was applied as an antimicrobial fiber finish with viscose fiber as an example material. The antimicrobial composition was applied together with an exemplifÿing sériés of fiber and textile treatment agents of different types, in more detail, with a finish agent for water- and oil repellent finish of synthetic and celluosic fibers and textiles (Nuva 2110, Clariant), a low foaming lubricant for ccllulosic fibers (Imacol C), an optical brightener for ccllulosic fibers (Leucophor BFB, Clariant), a viscose process additive/cleaning agent (Afilan ZS, Clariant) and a viscose nonwoven finish (Afilan HSGV, Clariant).
Aqueous fiber finish/treatment baths FB1-FB5 with compositions according to Table 5 were prepared. In association with each bath, a 3.3 g sample of dry viscose fiber ( 1.3 dtex) was pre-moistured with water and immersed into the bath (T=60 °C, volume 100 ml) for 3 minutes. Excess finish solution was removed from the fiber mass of each sample through pressing until a moisture content of 50 % (wet weight of the sample approximately 6.6 grams) was obtained. Ail the samples were dried at 80 °C for 40 minutes and cardcd.
Table 5
| Sample / Bath | Components | Concentration in water |
| AE171 /FBI | AM Comp. Nuva2ll0 | 0.5 % (v/v) 0.5 % (w/w) |
| AE172/FB2 | AM Comp. Imacol C | 0.5 % (v/v) 0.5 % (w/w) |
| AE173/FB3 | AM Comp. Leucophor BFB | 0.5 % (v/v) 0.5 % (w/w) |
| AE174/FB4 | AM Comp. Afilan ZS | 0.5 % (v/v) 0.5 % (w/w) |
| AE175/FB5 | AM Comp. Afilan HSGV | 0.5 % (v/v) 0.5 % (w/w) |
The finished and carded fiber samples were subjcctcd to a quantitative analysis of antimicrobial efficacy according to the international standard ISO 20743:2007 (Textiles Détermination of antibacterial activity of antibacterial finished products). The results are presented in Table 6.
Table 6
| Sample / Bath | Antibacterial activity value (ISO 20743:2007) |
| AE171 /FBI | >4.5 |
| AE172/FB2 | 3.2 |
| AE173/FB3 | >4.5 |
| AE174/FB4 | 3.1 |
| AE175/FB5 | >4.3 |
Various fiber and fabric finish bath compositions comprising the antimicrobial composition and heat applied in combination with the drying process may naturally affect the propcrties of the spécifie chemical structure of the finish combination (AM ionomer composition and other components of a spécifie bath) through e.g. inducing covalent bonding between functional groups of the finish agents and those incorporated to the fiber or fabric. This again may aller the electrical charge and water solubility of the final fiber surface finish composition and correspondingly increase the wash durability ofthe finished fiber and the textile products produced thereof.
Application Example 18
An antimicrobiai ionomcr composition according to Example 16 was applied as an aqueous dilution as an antimicrobiai fiber finish agent together with water- and oilrepcllent finish of synthetic and cclluosic fibers and textiles (Nuva 2110, Clariant). The thermal and UV tolérance of the AM ionomer composition was further increased with ammonium chloride and sodium saccharin dihydrate as included in the composition as stabilizers. A 100 ml finish bath according to Table 7 was prepared.
Table 7
| Sample / Bath | Components | Concentration in water |
| AE181 /FB6 | AM comp. Nuva 2110 NH4CI Sodium saccharin dihydrate | 0.5 % (v/v) 0.5 % (w/w) 0.3 % (w/v) 0.2 % (w/v) |
A viscose fiber (1.3 dtex) sample AE181 of 3.3 grains was treated with bath FB6 following similar steps and conditions as described in Example 17, however as dried at a température of 120 °C for 10 minutes. The antibacterial activity of the antibacterial finished fiber sample AE181 was measured according to international standard ISO 20743:2007. As a rcsult, an excellent antibacterial activity value of 3.9 was achieved for the sample.
Application Example 19
An antimicrobiai ionomer composition according to Example 16 was applied as an antimicrobiai fiber finish agent together with two water dispcrsible crosslinking agents. Various crosslinking agents used together with amine functional polymers rcsult in covalently bondcd fiber finish structures dccreasing the water solubility of the dried finish matrix. In the example, cpichlorohydrin and dipropylene glycol based epoxy resin (D.E.R 736P, Dow) and a water dispcrsible polyîsocyanate (Easaqua X D 803, Perstorp) were applied as crosslinking agents. A fiber treatment bath solution FS3 according to Table 8 was prepared.
Table 8
| Sample ! Solution | Components | Concentration in water |
| AE191 /FB7 | AM comp. Perstorp Easaqua X D 803 Dow D.E.R 803 | 0.5 % (v/v) 0.18% (v/v) 0.23 % (v/v) |
A viscose fiber (l.3 dtex) sample AE191 of 3.3 grams was treated with bath FB7 following similar steps and conditions as described in Example 17.
The antibacterial activity ofthe antibacterial fînished fiber was measured according to international standard ISO 20743:2007. As a resuit, an excellent antibacterial activity value of 3.9 was achieved for the sample.
Application Example 20
An antimicrobial ionomer composition according to Example 16 was applied as an antimicrobial fiber finish agent as combined with a self-emusifiable polyisocyanate -type crosslinking agent in a sequential multibath setup. Three 100 ml aqueous fiber treatment baths FB8.1-FB8.3 with compositions according to Table 8 were prepared. In the bath FS4.1 heat and UV tolérance of the antimicrobial ionomer composition was increased by incorporating ammonium chloride to the composition. The Bath FB4.2 comprised the aqueous solution of a di-isocyanate type crosslinking agent.
Table 9
| Sample ! Bath | Components | Concentration in water |
| AE201 /FB8.1 | AM comp. NH4Cl | 0.5 % (v/v) 0.2 % (w/v) |
| AE201 /FB8.2 | Perstorp Easaqua X D 803 | 0.2 % (v/v) |
| AE201 / FB8.3 | Only H2O |
A 3.3 g sample of dry viscose fiber (1.3 dtex) was pre-moistured with water and immersed sequentially into baths FB8.1-FB8.3 (for ail baths: T=60 °C, volume 100 ml) for 3 minutes per bath. Exccss finish solution was removed from the fiber mass after each bath throgh pressing until a moisture content of 50 % (wet weight of the sample approximately 6.6 grams) was obtained. Finally, the sample was dried at 100 °C for 30 minutes and carded, The antibacterial activity ofthe antibacterial fînished carded fiber was measured according
to international standard ISO 20743:2007. As a resuit, an excellent antibacterial activity value of >4.3 was achicvcd with the sample.
Application Example 21
The antimicrobial ionomer composition in accordance with the invention can be applied as an antimicrobial and dcodorizing agent and additive in multiple surface disinfection and sanitizing compositions and products including e.g. surface desinfection, hand disinfection, shoe and clothing déodorant and wet wipe liquid products and compositions and the like.
One of the unique advantages provided by the antimicrobial ionomer composition in surface treatment applications is the thin ionomeric layer provided on the treated surfaces, leaving the surfaces microbicidal after évaporation of the liquid solvents.
As an example, isopropyl alcohol was applied as a simplified example surface disinfection product and the antimicrobial ionomer composition was applied as an antimicrobial surface treatment additive component forming a dilute antimicrobial ionomer composition according to the invention. A stock solution of antimicrobial ionomer composition was prepared similarly to Example 16, however by using a cosmetic grade SP-012 (Nippon
Shokubai) polyethyleneimine. The stock composition was further diluted into an example product concentration with 200 parts of isopropyl alcohol. The bactericidal activity of the example surface disinfection product was tested following the standard EN 13697:2001 (a quantitative non-porous surface test for the évaluation of bactericidal and/or fimgicidal activity of chcmical disinfectants) showing >log5.8 (0 cfo after treatment = practically stérile) réduction for Staphylococcus aureus. The antimicrobial fonction of the thin antimicrobial ionomer layer left on the treated surface was demonstrated as foliows: a film of the composition was spread onto the surface of a stérile 5x5 cm PVC sheets through dip coating. Three similarly prepared replicate samples were dried for 24 hours at room température. The antimicrobial efficacy of the treated surface was tested following the international standard ISO 22196. The results indicated a log 4 réduction for Staphylococcus aureus.
Claims (27)
1. An antimicrobial ionomer composition which comprises an amine functional cationic polymer compound and silver halide.
2. The antimicrobial ionomer composition according to claim 1, further comprising a stabilizing component.
3. The antimicrobial ionomer composition according to claim 1, wherein silver halide is in 10 molecular form.
4. The antimicrobial ionomer composition according to claim 1, wherein silver halide is silver chloride.
15 5. The antimicrobial ionomer composition according to any of claims claim 1 to 4, comprising at Ieast one stabilizer substance selected from the groups of organic or inorganic substances, preferably a compound comprising ammonium cations, or saccharin, or organic substances carrying sulfonamide functional group(s), in particular the at Ieast one stabilizer substance is selected from the group comprising saccharin, cyclamic acid,
20 sulfadiazine, acesulfame and their alkali métal or ammonium salts or complex dérivatives, ammonium chloride and alkali métal chlorides.
6. The antimicrobial ionomer composition according to any of claims 1 to 5, comprising a solvent matrix, preferably formed by alcohols, such as methyl, ethyl, propyl or butyl
25 alcohol or water and combinations thereof.
7. The antimicrobial ionomer composition according to any of the preceding claims, wherein said amine functional polymer is selected from the group comprising; polyethyleneimine, polyvinylamine, polyacrylamine, polyhexamethylenebiguanîdine,
30 polyvinylpyridine and polyarylamine.
8. The antimicrobial ionomer composition according to any of the preceding claims, wherein said amine functional polymer comprises poly(ethyleneimine) having a molecular weight (Mw) between 200 and 3,000,000, in particular about 750 to 2,000,000.
9. The antimicrobial ionomer composition according to any of claims l to 8, obtainable by rcacting together (i) 70 to 99.99 parts by weight of at least one amine functionai polymer and 0.01 to 30
5 parts by weight of at least one silver halidc or;
(ii) 50 to 99.99 parts by weight of at least one amine functionai polymer, 0.01 to 50 parts by weight of at least one non-halide silver sait or complex compound, and hydrogen halide, or an alkaline métal or ammonium halide sait.
10 10. The antimicrobial ionomer composition according to claim 9, wherein (i) said at least one amine functionai polymer and silver halide; or (ii) said at least one amine functionai polymer and at least one silver sait or complex compound and hydrogen halide, or alkaline métal or ammonium halide sait, are further reactcd together with at least one stabilizer substance.
11. The antimicrobial ionomer composition according to claim 9, wherein the counter anion or ligand of said at least one silver sait or complex compound comprises an organic stabilizer substance.
20
12. The antimicrobial ionomer composition according to any of the preceding claims, wherein said silver halide comprises silver chloride, said hydrogen halide comprises hydrogen chloride and said alkaline métal halide sait comprises sodium chloride or potassium chloride.
25
13. The antimicrobial ionomer composition according to any of the preceding claims, wherein said reacting is carried out in a solvent matrix.
14. The antimicrobial ionomer composition according to any of the preceding claims, wherein said solvent matrix comprises alcohols, such as methyl, ethyl, propyl, butyl
30 alcohol or water and combinations thereof.
15. The antimicrobial ionomer composition according to any of the preceding claims, wherein the amine functionai groups of said amine functionai polymer hâve a fonction as further attaching said composition to a molecular structure of a second material through non-covalent bonding or covalent bonding or coordinate bonding or combinations thereof.
16. The antîmicrobial ionomer composition according to any of the preceding daims,
5 wherein said amine functional polymer is polyvinylamine or copolymer having 30-100 mol-% of vinylamine.
17. The antîmicrobial ionomer composition according to any of the preceding daims, wherein said amine functional polymer is graft polymer of polyvinylamine with
10 ethyleneimine.
18. The antîmicrobial ionomer composition according to any of the preceding daims, wherein said amine functional polymer is graft polymer of polyamidoamine with ethyleneimine
19. The antîmicrobial ionomer composition according to any ofthe preceding daims, wherein said amine functional polymer is a polyarylamine copolymer
20. The antîmicrobial ionomer composition according to any of the preceding daims,
20 wherein said amine functional polymer is polyacrylamine
21. The antîmicrobial ionomer composition according to any ofthe preceding daims, wherein said composition is intemally cross-linked through at least one cross-linking agent.
22. The antîmicrobial ionomer composition according to any of the preceding daims, wherein said composition is attached to a second material through at least one crosslinking agent.
30
23. The antîmicrobial ionomer composition according to any of the preceding daims, wherein the silver content of the composition is about 0.01 to 50 %, in particular about 1 to 30 %, preferably about 1.5 to 25 % by weight of the total weight of the composition.
(f
24, The antimicrobial composition according to any of the preceding claims, wherein the weight ratio ofthe silver compound to the amine compound is about l : 100 to 100:1, in particular 1-10:50-100.
5 25. A method of producing a polymcric antimicrobial composition, comprising reacting together (i) at least one amine functional polymer and silver halide; or (ii) at least onc amine functional polymer and at least one non-halidc silver sait or complex compound and hydrogen halide and/or alkaline métal halide sait; and, 10 (iii) optionally, at least one stabilizer substance.
26. The method according to claim 25, comprising reacting together (i) 70 to 99.99 parts by weight of at least one amine functional polymer and 0.01 to 30 parts by weight of at least one silver halide or;
15 (ii) 70 to 99.99 parts by weight of at least one amine functional polymer, 0.01 to 30 parts by weight of at least onc non-halide silver sait or complex compound, and hydrogen halide, or an alkaline métal or ammonium halide sait.
27. The method according to claim 25 or 26, comprising reacting together in a solvent
20 matrix (i) at least onc amine functional polymer;
(ii) a silver halide; and, (iii) optionally, at least one stabilizer substance.
25 28. The method according to claim 25 or 26, comprising reacting together in a solvent matrix (i) a non-halide silver sait or silver complex;
(ii) hydrogen halide or an alkaline métal halide sait or a combination thereof; and, (iii) optionally, at least one stabilizer substance.
29. The method according to any of claims 25 to 28 carried out in a solvent matrix preferably comprising alcohols, such as methyl alcohol, ethyl alcohol or water and combinations thereof.
30. The method according to any of claims 25 to 29, wherein additive compounds are incorporated into said composition providing means for modifying the physical-chcmical properties of said composition.
31. The use of an ionomer composition according to any of claims 1 to 24 or a composition produced by a method according to any of claims 25 to 30 for coating of host surfaces.
32. The use according to claim 31, comprising coating host surfaces selected from the group of fiber, fabric and bulk material surfaces, including synthetic semisynthetic and natural fibers, woven fabrics, nonwoven fabrics, knitted fabrics, papers, various polymer surfaces, métal surfaces, such as stccl surfaces, various coating surfaces, wood surfaces and fiber, fabric and bulk material surfaces.
33. The use according to claim 31 or 32, comprising coating a material selected from ccllulosic products (e.g. cellulose and viscose), proteins, polyesters, polyamides, chlorine cont. polymers, silicates, silicium dioxide, iron, pigments, paper, wood, cotton, plants, skin and hair.
34. The use according to any of claims 31 to 33, comprising using said composition as an antimicrobial agent, as a deodorizing agent or as an additive for antimicrobial or deodorizing agents, in particular the composition is used in compositions and products for surface desinfection, hand disinfection, as a shoe or clothing déodorant, or as a wet wipe liquid product or composition.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FI20115816 | 2011-08-22 | ||
| US61/525,888 | 2011-08-22 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| OA16743A true OA16743A (en) | 2015-12-14 |
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