JP2022104606A - Antibacterial coating agent - Google Patents
Antibacterial coating agent Download PDFInfo
- Publication number
- JP2022104606A JP2022104606A JP2021211750A JP2021211750A JP2022104606A JP 2022104606 A JP2022104606 A JP 2022104606A JP 2021211750 A JP2021211750 A JP 2021211750A JP 2021211750 A JP2021211750 A JP 2021211750A JP 2022104606 A JP2022104606 A JP 2022104606A
- Authority
- JP
- Japan
- Prior art keywords
- group
- antibacterial
- coating agent
- ether
- antibacterial coating
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 230000000844 anti-bacterial effect Effects 0.000 title claims abstract description 109
- 239000011248 coating agent Substances 0.000 title claims abstract description 54
- -1 silyl compound Chemical class 0.000 claims abstract description 54
- 229910052751 metal Inorganic materials 0.000 claims abstract description 24
- 239000002184 metal Substances 0.000 claims abstract description 24
- 239000004094 surface-active agent Substances 0.000 claims abstract description 15
- 229920001223 polyethylene glycol Polymers 0.000 claims description 27
- 239000002202 Polyethylene glycol Substances 0.000 claims description 21
- 229940008099 dimethicone Drugs 0.000 claims description 15
- 239000004205 dimethyl polysiloxane Substances 0.000 claims description 15
- 235000013870 dimethyl polysiloxane Nutrition 0.000 claims description 15
- 229920000435 poly(dimethylsiloxane) Polymers 0.000 claims description 15
- 150000005215 alkyl ethers Chemical class 0.000 claims description 11
- 229920003171 Poly (ethylene oxide) Polymers 0.000 claims description 9
- 125000003277 amino group Chemical group 0.000 claims description 9
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 claims description 7
- 229920001577 copolymer Polymers 0.000 claims description 7
- 229920002545 silicone oil Polymers 0.000 claims description 7
- 229910052709 silver Inorganic materials 0.000 claims description 7
- 239000004332 silver Substances 0.000 claims description 7
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 claims description 6
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 6
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims description 6
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 6
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims description 6
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 claims description 5
- 150000003839 salts Chemical class 0.000 claims description 5
- 239000002904 solvent Substances 0.000 claims description 5
- AUHDWARTFSKSAC-HEIFUQTGSA-N (2S,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)-2-(6-oxo-1H-purin-9-yl)oxolane-2-carboxylic acid Chemical compound [C@]1([C@H](O)[C@H](O)[C@@H](CO)O1)(N1C=NC=2C(O)=NC=NC12)C(=O)O AUHDWARTFSKSAC-HEIFUQTGSA-N 0.000 claims description 4
- GRSZFWQUAKGDAV-UHFFFAOYSA-N Inosinic acid Natural products OC1C(O)C(COP(O)(O)=O)OC1N1C(NC=NC2=O)=C2N=C1 GRSZFWQUAKGDAV-UHFFFAOYSA-N 0.000 claims description 4
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical group CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 claims description 4
- RQFCJASXJCIDSX-UUOKFMHZSA-N guanosine 5'-monophosphate Chemical compound C1=2NC(N)=NC(=O)C=2N=CN1[C@@H]1O[C@H](COP(O)(O)=O)[C@@H](O)[C@H]1O RQFCJASXJCIDSX-UUOKFMHZSA-N 0.000 claims description 4
- 235000013902 inosinic acid Nutrition 0.000 claims description 4
- 239000004245 inosinic acid Substances 0.000 claims description 4
- 229940028843 inosinic acid Drugs 0.000 claims description 4
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 4
- 125000006353 oxyethylene group Chemical group 0.000 claims description 4
- 125000003396 thiol group Chemical group [H]S* 0.000 claims description 4
- JLGLQAWTXXGVEM-UHFFFAOYSA-N triethylene glycol monomethyl ether Chemical compound COCCOCCOCCO JLGLQAWTXXGVEM-UHFFFAOYSA-N 0.000 claims description 4
- NKJOXAZJBOMXID-UHFFFAOYSA-N 1,1'-Oxybisoctane Chemical compound CCCCCCCCOCCCCCCCC NKJOXAZJBOMXID-UHFFFAOYSA-N 0.000 claims description 3
- DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 claims description 3
- LTSWUFKUZPPYEG-UHFFFAOYSA-N 1-decoxydecane Chemical compound CCCCCCCCCCOCCCCCCCCCC LTSWUFKUZPPYEG-UHFFFAOYSA-N 0.000 claims description 3
- CMCBDXRRFKYBDG-UHFFFAOYSA-N 1-dodecoxydodecane Chemical compound CCCCCCCCCCCCOCCCCCCCCCCCC CMCBDXRRFKYBDG-UHFFFAOYSA-N 0.000 claims description 3
- HANWHVWXFQSQGJ-UHFFFAOYSA-N 1-tetradecoxytetradecane Chemical compound CCCCCCCCCCCCCCOCCCCCCCCCCCCCC HANWHVWXFQSQGJ-UHFFFAOYSA-N 0.000 claims description 3
- OHJYHAOODFPJOD-UHFFFAOYSA-N 2-(2-ethylhexoxy)ethanol Chemical compound CCCCC(CC)COCCO OHJYHAOODFPJOD-UHFFFAOYSA-N 0.000 claims description 3
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 3
- ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 claims description 3
- DFPAKSUCGFBDDF-UHFFFAOYSA-N Nicotinamide Chemical group NC(=O)C1=CC=CN=C1 DFPAKSUCGFBDDF-UHFFFAOYSA-N 0.000 claims description 3
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 claims description 3
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 claims description 3
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 3
- QCWXUUIWCKQGHC-UHFFFAOYSA-N Zirconium Chemical compound [Zr] QCWXUUIWCKQGHC-UHFFFAOYSA-N 0.000 claims description 3
- 125000004423 acyloxy group Chemical group 0.000 claims description 3
- 125000003302 alkenyloxy group Chemical group 0.000 claims description 3
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- 229910052782 aluminium Inorganic materials 0.000 claims description 3
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims description 3
- 125000003368 amide group Chemical group 0.000 claims description 3
- 125000002344 aminooxy group Chemical group [H]N([H])O[*] 0.000 claims description 3
- 229910017052 cobalt Inorganic materials 0.000 claims description 3
- 239000010941 cobalt Substances 0.000 claims description 3
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 claims description 3
- 229910052802 copper Inorganic materials 0.000 claims description 3
- 239000010949 copper Substances 0.000 claims description 3
- DTPCFIHYWYONMD-UHFFFAOYSA-N decaethylene glycol Chemical compound OCCOCCOCCOCCOCCOCCOCCOCCOCCOCCO DTPCFIHYWYONMD-UHFFFAOYSA-N 0.000 claims description 3
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 3
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 3
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 claims description 3
- 229910052737 gold Inorganic materials 0.000 claims description 3
- 239000010931 gold Substances 0.000 claims description 3
- 235000013928 guanylic acid Nutrition 0.000 claims description 3
- 239000004226 guanylic acid Substances 0.000 claims description 3
- 125000005843 halogen group Chemical group 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
- 229910052742 iron Inorganic materials 0.000 claims description 3
- 125000003253 isopropoxy group Chemical group [H]C([H])([H])C([H])(O*)C([H])([H])[H] 0.000 claims description 3
- 239000011133 lead Substances 0.000 claims description 3
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 claims description 3
- 229910052753 mercury Inorganic materials 0.000 claims description 3
- 229910052750 molybdenum Inorganic materials 0.000 claims description 3
- 239000011733 molybdenum Substances 0.000 claims description 3
- 229910052759 nickel Inorganic materials 0.000 claims description 3
- 229910052763 palladium Inorganic materials 0.000 claims description 3
- 229940061571 peg-9 dimethicone Drugs 0.000 claims description 3
- 229910052697 platinum Inorganic materials 0.000 claims description 3
- 229910052718 tin Inorganic materials 0.000 claims description 3
- 239000011135 tin Substances 0.000 claims description 3
- 229910052719 titanium Inorganic materials 0.000 claims description 3
- 239000010936 titanium Substances 0.000 claims description 3
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 claims description 3
- 229910052721 tungsten Inorganic materials 0.000 claims description 3
- 239000010937 tungsten Substances 0.000 claims description 3
- PSVXZQVXSXSQRO-UHFFFAOYSA-N undecaethylene glycol Chemical compound OCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCO PSVXZQVXSXSQRO-UHFFFAOYSA-N 0.000 claims description 3
- 229910052720 vanadium Inorganic materials 0.000 claims description 3
- GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 claims description 3
- 229910052725 zinc Inorganic materials 0.000 claims description 3
- 239000011701 zinc Substances 0.000 claims description 3
- 229910052726 zirconium Inorganic materials 0.000 claims description 3
- PVBRXXAAPNGWGE-LGVAUZIVSA-L disodium 5'-guanylate Chemical compound [Na+].[Na+].C1=2NC(N)=NC(=O)C=2N=CN1[C@@H]1O[C@H](COP([O-])([O-])=O)[C@@H](O)[C@H]1O PVBRXXAAPNGWGE-LGVAUZIVSA-L 0.000 claims description 2
- 125000003506 n-propoxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])O* 0.000 claims description 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 1
- 230000003301 hydrolyzing effect Effects 0.000 claims 1
- 239000003125 aqueous solvent Substances 0.000 abstract description 8
- 230000005923 long-lasting effect Effects 0.000 abstract description 3
- 230000006641 stabilisation Effects 0.000 abstract description 3
- 238000011105 stabilization Methods 0.000 abstract description 3
- 238000001465 metallisation Methods 0.000 abstract 1
- 238000000576 coating method Methods 0.000 description 16
- 230000000052 comparative effect Effects 0.000 description 13
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 10
- 230000001954 sterilising effect Effects 0.000 description 10
- 150000001875 compounds Chemical class 0.000 description 9
- 238000011156 evaluation Methods 0.000 description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 8
- 239000007788 liquid Substances 0.000 description 8
- 238000004659 sterilization and disinfection Methods 0.000 description 8
- 238000012360 testing method Methods 0.000 description 8
- 230000015572 biosynthetic process Effects 0.000 description 7
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- 238000001035 drying Methods 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- 238000000034 method Methods 0.000 description 6
- 239000011734 sodium Substances 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- 150000001413 amino acids Chemical class 0.000 description 5
- 125000004432 carbon atom Chemical group C* 0.000 description 5
- 239000012085 test solution Substances 0.000 description 5
- 241000894006 Bacteria Species 0.000 description 4
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 4
- 150000003973 alkyl amines Chemical class 0.000 description 4
- 238000002474 experimental method Methods 0.000 description 4
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 4
- 229920002477 rna polymer Polymers 0.000 description 4
- 229910052708 sodium Inorganic materials 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 229960000686 benzalkonium chloride Drugs 0.000 description 3
- CADWTSSKOVRVJC-UHFFFAOYSA-N benzyl(dimethyl)azanium;chloride Chemical compound [Cl-].C[NH+](C)CC1=CC=CC=C1 CADWTSSKOVRVJC-UHFFFAOYSA-N 0.000 description 3
- 229930182470 glycoside Natural products 0.000 description 3
- 150000002739 metals Chemical class 0.000 description 3
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- 239000011347 resin Substances 0.000 description 3
- 229920005989 resin Polymers 0.000 description 3
- NDVLTYZPCACLMA-UHFFFAOYSA-N silver oxide Chemical compound [O-2].[Ag+].[Ag+] NDVLTYZPCACLMA-UHFFFAOYSA-N 0.000 description 3
- 230000000087 stabilizing effect Effects 0.000 description 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 2
- 241000222122 Candida albicans Species 0.000 description 2
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 2
- 239000006087 Silane Coupling Agent Substances 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 150000004996 alkyl benzenes Chemical class 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 239000012298 atmosphere Substances 0.000 description 2
- HTZCNXWZYVXIMZ-UHFFFAOYSA-M benzyl(triethyl)azanium;chloride Chemical compound [Cl-].CC[N+](CC)(CC)CC1=CC=CC=C1 HTZCNXWZYVXIMZ-UHFFFAOYSA-M 0.000 description 2
- RLGQACBPNDBWTB-UHFFFAOYSA-N cetyltrimethylammonium ion Chemical compound CCCCCCCCCCCCCCCC[N+](C)(C)C RLGQACBPNDBWTB-UHFFFAOYSA-N 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 229930182478 glucoside Natural products 0.000 description 2
- 150000002431 hydrogen Chemical class 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 150000007524 organic acids Chemical group 0.000 description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 239000007921 spray Substances 0.000 description 2
- 229910001220 stainless steel Inorganic materials 0.000 description 2
- 239000010935 stainless steel Substances 0.000 description 2
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 2
- VDZOOKBUILJEDG-UHFFFAOYSA-M tetrabutylammonium hydroxide Chemical compound [OH-].CCCC[N+](CCCC)(CCCC)CCCC VDZOOKBUILJEDG-UHFFFAOYSA-M 0.000 description 2
- RRQYJINTUHWNHW-UHFFFAOYSA-N 1-ethoxy-2-(2-ethoxyethoxy)ethane Chemical compound CCOCCOCCOCC RRQYJINTUHWNHW-UHFFFAOYSA-N 0.000 description 1
- CNJRPYFBORAQAU-UHFFFAOYSA-N 1-ethoxy-2-(2-methoxyethoxy)ethane Chemical compound CCOCCOCCOC CNJRPYFBORAQAU-UHFFFAOYSA-N 0.000 description 1
- OAYXUHPQHDHDDZ-UHFFFAOYSA-N 2-(2-butoxyethoxy)ethanol Chemical compound CCCCOCCOCCO OAYXUHPQHDHDDZ-UHFFFAOYSA-N 0.000 description 1
- SBASXUCJHJRPEV-UHFFFAOYSA-N 2-(2-methoxyethoxy)ethanol Chemical compound COCCOCCO SBASXUCJHJRPEV-UHFFFAOYSA-N 0.000 description 1
- LKAWQFHWVVSFTR-UHFFFAOYSA-N 2-(methylamino)ethanol;hydrochloride Chemical compound [Cl-].C[NH2+]CCO LKAWQFHWVVSFTR-UHFFFAOYSA-N 0.000 description 1
- WFSMVVDJSNMRAR-UHFFFAOYSA-N 2-[2-(2-ethoxyethoxy)ethoxy]ethanol Chemical compound CCOCCOCCOCCO WFSMVVDJSNMRAR-UHFFFAOYSA-N 0.000 description 1
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- JGFDZZLUDWMUQH-UHFFFAOYSA-N Didecyldimethylammonium Chemical compound CCCCCCCCCC[N+](C)(C)CCCCCCCCCC JGFDZZLUDWMUQH-UHFFFAOYSA-N 0.000 description 1
- RUPBZQFQVRMKDG-UHFFFAOYSA-M Didecyldimethylammonium chloride Chemical compound [Cl-].CCCCCCCCCC[N+](C)(C)CCCCCCCCCC RUPBZQFQVRMKDG-UHFFFAOYSA-M 0.000 description 1
- OJIYIVCMRYCWSE-UHFFFAOYSA-M Domiphen bromide Chemical compound [Br-].CCCCCCCCCCCC[N+](C)(C)CCOC1=CC=CC=C1 OJIYIVCMRYCWSE-UHFFFAOYSA-M 0.000 description 1
- QWZLBLDNRUUYQI-UHFFFAOYSA-M Methylbenzethonium chloride Chemical compound [Cl-].CC1=CC(C(C)(C)CC(C)(C)C)=CC=C1OCCOCC[N+](C)(C)CC1=CC=CC=C1 QWZLBLDNRUUYQI-UHFFFAOYSA-M 0.000 description 1
- OKIZCWYLBDKLSU-UHFFFAOYSA-M N,N,N-Trimethylmethanaminium chloride Chemical compound [Cl-].C[N+](C)(C)C OKIZCWYLBDKLSU-UHFFFAOYSA-M 0.000 description 1
- OPKOKAMJFNKNAS-UHFFFAOYSA-N N-methylethanolamine Chemical compound CNCCO OPKOKAMJFNKNAS-UHFFFAOYSA-N 0.000 description 1
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- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 1
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- 239000002253 acid Substances 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 125000003282 alkyl amino group Chemical group 0.000 description 1
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- 150000001412 amines Chemical class 0.000 description 1
- 230000002238 attenuated effect Effects 0.000 description 1
- 230000001580 bacterial effect Effects 0.000 description 1
- YSJGOMATDFSEED-UHFFFAOYSA-M behentrimonium chloride Chemical compound [Cl-].CCCCCCCCCCCCCCCCCCCCCC[N+](C)(C)C YSJGOMATDFSEED-UHFFFAOYSA-M 0.000 description 1
- 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
- 229960001950 benzethonium chloride Drugs 0.000 description 1
- VJGNLOIQCWLBJR-UHFFFAOYSA-M benzyl(tributyl)azanium;chloride Chemical compound [Cl-].CCCC[N+](CCCC)(CCCC)CC1=CC=CC=C1 VJGNLOIQCWLBJR-UHFFFAOYSA-M 0.000 description 1
- KXHPPCXNWTUNSB-UHFFFAOYSA-M benzyl(trimethyl)azanium;chloride Chemical compound [Cl-].C[N+](C)(C)CC1=CC=CC=C1 KXHPPCXNWTUNSB-UHFFFAOYSA-M 0.000 description 1
- 230000033228 biological regulation Effects 0.000 description 1
- 229940095731 candida albicans Drugs 0.000 description 1
- 201000003984 candidiasis Diseases 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 150000001721 carbon Chemical group 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 229960003431 cetrimonium Drugs 0.000 description 1
- 229960001927 cetylpyridinium chloride Drugs 0.000 description 1
- YMKDRGPMQRFJGP-UHFFFAOYSA-M cetylpyridinium chloride Chemical compound [Cl-].CCCCCCCCCCCCCCCC[N+]1=CC=CC=C1 YMKDRGPMQRFJGP-UHFFFAOYSA-M 0.000 description 1
- WOWHHFRSBJGXCM-UHFFFAOYSA-M cetyltrimethylammonium chloride Chemical compound [Cl-].CCCCCCCCCCCCCCCC[N+](C)(C)C WOWHHFRSBJGXCM-UHFFFAOYSA-M 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 238000011109 contamination Methods 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 238000012258 culturing Methods 0.000 description 1
- 229940073499 decyl glucoside Drugs 0.000 description 1
- 229940078672 didecyldimethylammonium Drugs 0.000 description 1
- 229960004670 didecyldimethylammonium chloride Drugs 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 229940019778 diethylene glycol diethyl ether Drugs 0.000 description 1
- 229940028356 diethylene glycol monobutyl ether Drugs 0.000 description 1
- XXJWXESWEXIICW-UHFFFAOYSA-N diethylene glycol monoethyl ether Chemical compound CCOCCOCCO XXJWXESWEXIICW-UHFFFAOYSA-N 0.000 description 1
- 229940075557 diethylene glycol monoethyl ether Drugs 0.000 description 1
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 1
- GVGUFUZHNYFZLC-UHFFFAOYSA-N dodecyl benzenesulfonate;sodium Chemical compound [Na].CCCCCCCCCCCCOS(=O)(=O)C1=CC=CC=C1 GVGUFUZHNYFZLC-UHFFFAOYSA-N 0.000 description 1
- SYELZBGXAIXKHU-UHFFFAOYSA-N dodecyldimethylamine N-oxide Chemical compound CCCCCCCCCCCC[N+](C)(C)[O-] SYELZBGXAIXKHU-UHFFFAOYSA-N 0.000 description 1
- 229960001859 domiphen bromide Drugs 0.000 description 1
- 125000003700 epoxy group Chemical group 0.000 description 1
- CWAFVXWRGIEBPL-UHFFFAOYSA-N ethoxysilane Chemical compound CCO[SiH3] CWAFVXWRGIEBPL-UHFFFAOYSA-N 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 208000015181 infectious disease Diseases 0.000 description 1
- PYIDGJJWBIBVIA-UYTYNIKBSA-N lauryl glucoside Chemical compound CCCCCCCCCCCCO[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O PYIDGJJWBIBVIA-UYTYNIKBSA-N 0.000 description 1
- 229940048848 lauryl glucoside Drugs 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 229910021645 metal ion Inorganic materials 0.000 description 1
- 150000001455 metallic ions Chemical class 0.000 description 1
- 125000005395 methacrylic acid group Chemical group 0.000 description 1
- 229960002285 methylbenzethonium chloride Drugs 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- HEGSGKPQLMEBJL-RKQHYHRCSA-N octyl beta-D-glucopyranoside Chemical compound CCCCCCCCO[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O HEGSGKPQLMEBJL-RKQHYHRCSA-N 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- JCGNDDUYTRNOFT-UHFFFAOYSA-N oxolane-2,4-dione Chemical compound O=C1COC(=O)C1 JCGNDDUYTRNOFT-UHFFFAOYSA-N 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 238000011056 performance test Methods 0.000 description 1
- 230000001699 photocatalysis Effects 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 229920000259 polyoxyethylene lauryl ether Polymers 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 239000013641 positive control Substances 0.000 description 1
- 230000000644 propagated effect Effects 0.000 description 1
- 125000001453 quaternary ammonium group Chemical group 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 229910001923 silver oxide Inorganic materials 0.000 description 1
- 229940077386 sodium benzenesulfonate Drugs 0.000 description 1
- 229940080264 sodium dodecylbenzenesulfonate Drugs 0.000 description 1
- RLJSXMVTLMHXJS-UHFFFAOYSA-M sodium;4-decylbenzenesulfonate Chemical compound [Na+].CCCCCCCCCCC1=CC=C(S([O-])(=O)=O)C=C1 RLJSXMVTLMHXJS-UHFFFAOYSA-M 0.000 description 1
- MZSDGDXXBZSFTG-UHFFFAOYSA-M sodium;benzenesulfonate Chemical compound [Na+].[O-]S(=O)(=O)C1=CC=CC=C1 MZSDGDXXBZSFTG-UHFFFAOYSA-M 0.000 description 1
- 230000003068 static effect Effects 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 230000002459 sustained effect Effects 0.000 description 1
- JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 description 1
- HWCKGOZZJDHMNC-UHFFFAOYSA-M tetraethylammonium bromide Chemical compound [Br-].CC[N+](CC)(CC)CC HWCKGOZZJDHMNC-UHFFFAOYSA-M 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- LPSKDVINWQNWFE-UHFFFAOYSA-M tetrapropylazanium;hydroxide Chemical compound [OH-].CCC[N+](CCC)(CCC)CCC LPSKDVINWQNWFE-UHFFFAOYSA-M 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- MQAYPFVXSPHGJM-UHFFFAOYSA-M trimethyl(phenyl)azanium;chloride Chemical compound [Cl-].C[N+](C)(C)C1=CC=CC=C1 MQAYPFVXSPHGJM-UHFFFAOYSA-M 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 230000002087 whitening effect Effects 0.000 description 1
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- Agricultural Chemicals And Associated Chemicals (AREA)
- Paints Or Removers (AREA)
Abstract
Description
本発明は，抗菌性コーティング剤に関する。 The present invention relates to an antibacterial coating agent.
細菌，ウイルスに関する感染症の予防には，接触感染の対策が必要である。すなわち，人が接触する箇所を，抗菌状態とすることは有効な対策の一つである。 To prevent infectious diseases related to bacteria and viruses, it is necessary to take measures against contact infections. In other words, it is one of the effective measures to put the part that people come into contact with in an antibacterial state.
無菌的な処理を行う一つの方法として，アルコールなど抗菌力を有する液体の，空間や物体への噴霧が行われている。かかる場合，噴霧対象となる空間や物体は，一時的な無菌状態を維持することが可能である。しかるに，人が手指等で接触するなどして，容易に無菌状態は解除され，汚染源となってしまう。
このような観点から，無菌状態を維持しうる抗菌塗料に関する技術が開示されている（特許文献１）。
As one method of aseptic treatment, a liquid having antibacterial activity such as alcohol is sprayed on a space or an object. In such a case, the space or object to be sprayed can be temporarily kept sterile. However, the aseptic condition is easily released by human contact with fingers or the like, and it becomes a source of contamination.
From this point of view, a technique relating to an antibacterial paint capable of maintaining an aseptic state is disclosed (Patent Document 1).
特許文献１には，光触媒成分となる金属を含んだ抗菌塗料に関する技術が開示されている。先行技術は，抗菌効果を発揮する点において有用であるものの，製造方法が比較的煩雑であり，コストも高くなりがちな点において課題を有する。加えて先行技術は，抗菌効果が静的な状態では安定しているものの，人体の接触により塗膜がはがれる，あるいは塗膜が劣化するという動的な状態において抗菌効果の持続性に課題がある。
上記事情を背景として，本発明では，比較的安価であり，かつ，抗菌効果と持続性の高い抗菌組成物の開発を課題とする。 Against the background of the above circumstances, it is an object of the present invention to develop an antibacterial composition which is relatively inexpensive and has a high antibacterial effect and durability.
発明者は，鋭意研究の結果，加水分解性シリル化合物，金属性イオン，界面活性剤，水性溶媒，これらを組成成分とすることで，対象物表面の皮膜と抗菌が可能な組成物として構成することに着想した。
すなわち，加水分解性シリル化合物としての対象物への結合性と抗菌性金属の安定化，抗菌性金属としての抗菌性，これらを界面活性剤により水性溶媒中で安定化させることにより，抗菌力ならびに持続性の向上を達成しうることを見出し，発明を完成させた。
As a result of diligent research, the inventor constructs a composition capable of forming a film on the surface of an object and antibacterial by using hydrolyzable silyl compounds, metallic ions, surfactants, and aqueous solvents as composition components. I came up with that.
That is, the binding property to the object as a hydrolyzable silyl compound and the stabilization of the antibacterial metal, the antibacterial property as the antibacterial metal, and the antibacterial activity and the antibacterial activity by stabilizing these in an aqueous solvent with a surfactant. He found that the improvement of sustainability could be achieved and completed the invention.
本発明は，以下の構成からなる。
［1］加水分解性シリル化合物と，抗菌性金属と，界面活性剤と，溶媒とからなることを特徴とする抗菌性コーティング剤。
The present invention has the following configurations.
[1] An antibacterial coating agent comprising a hydrolyzable silyl compound, an antibacterial metal, a surfactant, and a solvent.
［2］界面活性剤として，水溶性変性シリコーンオイルを少なくとも含む［1］に記載の抗菌性コーティング剤。
［3］水溶性変性シリコーンオイルが，PEG-3メチルエーテルジメチコン，PEG-9ジメチコン，PEG-10メチルエーテルジメチコン，PEG-11メチルエーテルジメチコン，PEG12ジメチコン，PEG/PPG-20/22ブチルエーテルジメチコン，ラウリルPEG/PPG-18/18メチコン，ポリ（オキシエチレン・オキシプロピレン）メチルポリシロキサン共重合体，ポリオキシエチレン・メチルポリシロキサン共重合体のいずれか又は複数から選択される［1］又は［2］に記載の抗菌性コーティング剤。
[2] The antibacterial coating agent according to [1], which contains at least a water-soluble modified silicone oil as a surfactant.
[3] Water-soluble modified silicone oil is PEG-3 methyl ether dimethicone, PEG-9 dimethicone, PEG-10 methyl ether dimethicone, PEG-11 methyl ether dimethicone, PEG12 dimethicone, PEG / PPG-20 / 22 butyl ether dimethicone, lauryl. Selected from one or more of PEG / PPG-18 / 18 methicone, poly (oxyethylene / oxypropylene) methylpolysiloxane copolymer, polyoxyethylene / methylpolysiloxane copolymer [1] or [2] The antibacterial coating agent described in.
［4］界面活性剤として，さらに直鎖アルキルベンゼンスルホン酸ナトリウム，アルキルグリコシド，アルキルアミンオキシド，第四級アンモニウム塩，ポリオキシエチレンアルキルエーテル，ポリエチレングリコールアルキルエーテルのいずれか又は複数を含む［1］から［3］のいずれかに記載の抗菌性コーティング剤。
［5］ポリエチレングリコールアルキルエーテルが，ポリエチレングリコールモノ-2-エチルヘキシルエーテル，ポリエチレングリコールモノオクチルエーテル，ポリエチレングリコールモノデシルエーテル，ポリエチレングリコールモノドデシルエーテル，ポリエチレングリコールモノテトラデシルエーテルのいずれか又は複数から選択される［4］に記載の抗菌性コーティング剤。
[4] From [1], the surfactant further contains one or more of linear alkylbenzene sulfonate sodium, alkyl glycoside, alkylamine oxide, quaternary ammonium salt, polyoxyethylene alkyl ether, polyethylene glycol alkyl ether. The antibacterial coating agent according to any one of [3].
[5] Polyethylene glycol alkyl ether is selected from one or more of polyethylene glycol mono-2-ethylhexyl ether, polyethylene glycol monooctyl ether, polyethylene glycol monodecyl ether, polyethylene glycol monododecyl ether, and polyethylene glycol monotetradecyl ether. The antibacterial coating agent according to [4].
［6］さらに，アミノ酸有機化合物を含む［1］から［5］のいずれかに記載の抗菌性コーティング剤。
［7］アミノ酸有機化合物が，グアニル酸，イノシン酸，もしくはこれらの塩のいずれか又は複数から選択される［6］に記載の抗菌性コーティング剤。
［8］アミノ酸有機化合物が，グアニル酸ナトリウムである［7］に記載の抗菌性コーティング剤。
[6] The antibacterial coating agent according to any one of [1] to [5], which further contains an amino acid organic compound.
[7] The antibacterial coating agent according to [6], wherein the amino acid organic compound is selected from guanylic acid, inosinic acid, or one or a plurality of salts thereof.
[8] The antibacterial coating agent according to [7], wherein the amino acid organic compound is sodium guanylate.
［9］加水分解性シリル化合物が，水酸基，水素，ハロゲン原子，アルコキシ基，ジアルコキシ基，トリアルコキシ基，アシルオキシ基，ケトキシメート基，アミノ基，アミド基，酸アミド基，アミノオキシ基，メルカプト基，アルケニルオキシ基，ｎ－プロポキシ基，イソプロポキシ基のいずれかを有する加水分解性シリル化合物から選択される［1］から［8］のいずれかに記載の抗菌性コーティング剤。
［10］加水分解性シリル化合物が，メトキシ基，エトキシ基のいずれかを有する加水分解性シリル化合物から選択される［9］に記載の抗菌性コーティング剤。
［11］抗菌性金属が，金，銀，銅，白金，亜鉛，チタン，タングステン，ニッケル，鉄，スズ，水銀，パラジウム，アルミニウム，コバルト，モリブデン，鉛，バナジウム，ジルコニウムのいずれか又は複数から選択される［1］から［10］のいずれかに記載の抗菌性コーティング剤。
[9] The hydrolyzable silyl compound is a hydroxyl group, hydrogen, halogen atom, alkoxy group, dialkoxy group, trialkoxy group, acyloxy group, ketoximate group, amino group, amide group, acid amide group, aminooxy group, mercapto group. , The antibacterial coating agent according to any one of [1] to [8] selected from hydrolyzable silyl compounds having any of an alkenyloxy group, an n-propoxy group and an isopropoxy group.
[10] The antibacterial coating agent according to [9], wherein the hydrolyzable silyl compound is selected from the hydrolyzable silyl compounds having either a methoxy group or an ethoxy group.
[11] The antibacterial metal is selected from one or more of gold, silver, copper, platinum, zinc, titanium, tungsten, nickel, iron, tin, mercury, palladium, aluminum, cobalt, molybdenum, lead, vanadium, and zirconium. The antibacterial coating agent according to any one of [1] to [10].
本発明により，比較的安価であり，かつ，抗菌持続性の高い抗菌性コーティング剤の提供が可能となった。 INDUSTRIAL APPLICABILITY According to the present invention, it has become possible to provide an antibacterial coating agent which is relatively inexpensive and has high antibacterial durability.
本発明の抗菌性コーティング剤は，加水分解性シリル化合物と，抗菌性金属と，界面活性剤と，溶媒とからなることを特徴とする。
すなわち，本発明の抗菌性コーティング剤は，シリル化合物としての対象物への結合性と抗菌性金属の安定化，抗菌性金属としての抗菌性，これらを界面活性剤により溶媒中で安定化させることにより，抗菌力ならびに持続性の向上を達成しうる。
本発明の抗菌性コーティング剤は，塗布することにより，抗菌効果を発揮するとともに，持続性に優れ，汎用的な抗菌性コーティング剤として用いることができる。また，本発明の抗菌性コーティング剤の好適な用途として，好ましくは人体接触が前提となる箇所，さらに好ましくは手指接触が前提となる場所に塗布して抗菌効果を発揮する抗菌処理方法として構成することができる。
The antibacterial coating agent of the present invention is characterized by comprising a hydrolyzable silyl compound, an antibacterial metal, a surfactant, and a solvent.
That is, the antibacterial coating agent of the present invention has the ability to bind to an object as a silyl compound, stabilize the antibacterial metal, and stabilize the antibacterial property as an antibacterial metal in a solvent with a surfactant. This can achieve improved antibacterial activity as well as sustainability.
When applied, the antibacterial coating agent of the present invention exhibits an antibacterial effect, has excellent durability, and can be used as a general-purpose antibacterial coating agent. Further, as a suitable use of the antibacterial coating agent of the present invention, it is configured as an antibacterial treatment method that exerts an antibacterial effect by being applied to a place where human body contact is premised, and more preferably a place where finger contact is premised. be able to.
加水分解性シリル化合物は，加水分解反応により塗布対象に定着させるとともに，抗菌性金属を安定化させる役割を果たす。加水分解性シリル化合物は，かかる役割・機能を果たす限り特に限定する必要はなく，種々の構造とすることができる。 The hydrolyzable silyl compound plays a role of fixing to the object to be coated by a hydrolysis reaction and stabilizing an antibacterial metal. The hydrolyzable silyl compound does not need to be particularly limited as long as it fulfills such a role / function, and may have various structures.
加水分解性シリル化合物は，典型的には，X-Si（OR）nで表されるシランカップリング剤として表すことができる。
Xは，反応性官能基であり，例えば，アミノ基，アルキルアミノ基，エポキシ基，メタクリル基，ビニル基，メルカプト基などを用いることができる。
Rは，H，ハロゲン，炭素原子若しくは窒素原子を含んだ側鎖として表すことができる。また，nは1から3の整数である。
このようなRとして，水酸基，水素，ハロゲン原子，アルコキシ基，ジアルコキシ基，トリアルコキシ基，アシルオキシ基，ケトキシメート基，アミノ基，アミド基，酸アミド基，アミノオキシ基，メルカプト基，アルケニルオキシ基，ｎ－プロポキシ基，イソプロポキシ基のいずれかから選択することができ，より好ましくはメトキシ基，エトキシ基のいずれかを選択することができる。
シランカップリング剤の具体的な化合物としては，例えば，H2N（CH2）3Si（OCH3）3，H2N（CH2）2NH（CH2）3Si（OCH3）3（TMSPEDA），H2N（CH2）2NH（CH2）2NH（CH2）3 Si（OCH3）3（TMSPDETA），H2N（CH2）3Si（OC2H5）3，H2N（CH2）2NH（CH2）3Si（OC2H5）3，H2N（CH2）2 NH（CH2）2 NH（CH2）3 Si（OC2H5）3，H2N（CH2）3Si（CH3）（OC2H5）2，H2N（CH2）2NH（CH2）3Si（CH3）（OC2H5）2，H2N（CH2）2NH（CH2）2NH（CH2）3Si（CH3）2（OC2H5）などを用いることができる。
The hydrolyzable silyl compound can typically be represented as a silane coupling agent represented by X-Si (OR) n .
X is a reactive functional group, and for example, an amino group, an alkylamino group, an epoxy group, a methacrylic group, a vinyl group, a mercapto group and the like can be used.
R can be represented as a side chain containing H, a halogen, a carbon atom or a nitrogen atom. Also, n is an integer from 1 to 3.
Such R includes hydroxyl group, hydrogen, halogen atom, alkoxy group, dialkoxy group, trialkoxy group, acyloxy group, ketoximate group, amino group, amide group, acid amide group, aminooxy group, mercapto group and alkenyloxy group. , N-propoxy group or isopropoxy group can be selected, and more preferably any of methoxy group and ethoxy group can be selected.
Specific compounds of the silane coupling agent include, for example, H 2 N (CH 2 ) 3 Si (OCH 3 ) 3 , H 2 N (CH 2 ) 2 NH (CH 2 ) 3 Si (OCH 3 ) 3 ( TMSPEDA), H 2 N (CH 2 ) 2 NH (CH 2 ) 2 NH (CH 2 ) 3 Si (OCH 3 ) 3 (TMSPDETA), H 2 N (CH 2 ) 3 Si (OC 2 H 5 ) 3 , H 2 N (CH 2 ) 2 NH (CH 2 ) 3 Si (OC 2 H 5 ) 3 , H 2 N (CH 2 ) 2 NH (CH 2 ) 2 NH (CH 2 ) 3 Si (OC 2 H 5 ) 3 , H 2 N (CH 2 ) 3 Si (CH 3 ) (OC 2 H 5 ) 2 , H 2 N (CH 2 ) 2 NH (CH 2 ) 3 Si (CH 3 ) (OC 2 H 5 ) 2 , H 2 N (CH 2 ) 2 NH (CH 2 ) 2 NH (CH 2 ) 3 Si (CH 3 ) 2 (OC 2 H 5 ) etc. can be used.
抗菌性金属は，金属イオンとして添加するものであり，加水分解性シリル化合物により安定化され持続的な抗菌性能を発揮する役割を果たす。抗菌性金属は，かかる役割を果たす限り特に限定する必要はなく，種々の金属から選択することができる。
抗菌性金属は，典型的には，金，銀，銅，白金，亜鉛，チタン，タングステン，ニッケル，鉄，スズ，水銀，パラジウム，アルミニウム，コバルト，モリブデン，鉛，バナジウム，ジルコニウムのいずれか又は複数から選択すればよく，好適には，銀を用いることができる。
Antibacterial metals are added as metal ions and are stabilized by hydrolyzable silyl compounds to play a role in exerting sustained antibacterial performance. The antibacterial metal is not particularly limited as long as it plays such a role, and can be selected from various metals.
Antibacterial metals are typically one or more of gold, silver, copper, platinum, zinc, titanium, tungsten, nickel, iron, tin, mercury, palladium, aluminum, cobalt, molybdenum, lead, vanadium, zirconium. However, silver can be preferably used.
抗菌性金属の含量について，選択する金属の安全性ならびに有効性を考慮したうえで，カップリング樹脂性化合物の物理量を勘案し適宜調整することができる。
すなわち，抗菌性金属の含量は，選択された金属の安全性を踏まえて上限値を設定するとともに，有効性を考慮したうえで下限値を設定することができる。加えて，塗布する対象物の素材との反応性ならびに実際の使用環境での規制等から，含量を適宜調整することができる。
抗菌性金属の含量は，抗菌性コーティング剤において，典型的には0.1から100,000ppmの濃度で添加することができ，好ましくは10から10,000ppm，さらに好ましくは30から1,000ppm，特に好ましくは50から500ppm，最も好ましくは90から300ppmとすることができる。
The content of the antibacterial metal can be appropriately adjusted in consideration of the safety and effectiveness of the selected metal and the physical quantity of the coupling resin compound.
That is, the content of the antibacterial metal can be set to an upper limit in consideration of the safety of the selected metal and a lower limit in consideration of its effectiveness. In addition, the content can be adjusted as appropriate from the reactivity of the object to be applied with the material and the regulations in the actual usage environment.
The content of the antibacterial metal can be added in antibacterial coatings at a concentration typically 0.1 to 100,000 ppm, preferably 10 to 10,000 ppm, more preferably 30 to 1,000 ppm, and particularly preferably 50 to 50. It can be 500 ppm, most preferably 90 to 300 ppm.
本発明において界面活性剤は，加水分解性シリル化合物と，抗菌性金属を水性溶媒中で安定化させるとともに，抗菌力を向上させる役割を果たす。界面活性剤は，かかる役割を果たす限り特に限定する必要はなく，種々の界面活性剤を用いることができる。 In the present invention, the surfactant plays a role of stabilizing the hydrolyzable silyl compound and the antibacterial metal in an aqueous solvent and improving the antibacterial activity. The surfactant is not particularly limited as long as it plays such a role, and various surfactants can be used.
界面活性剤として，少なくとも水溶性変性シリコーンオイルを用いることが好ましい。これにより，本発明の抗菌性コーキング剤の安定性ならびに抗菌力をさらに向上させる効果を有する。
水溶性変性シリコーンオイル（ポリエーテル変性シリコーン）としては，PEG-3メチルエーテルジメチコン，PEG-9ジメチコン，PEG-10メチルエーテルジメチコン，PEG-11メチルエーテルジメチコン，PEG12ジメチコン，PEG/PPG-20/22ブチルエーテルジメチコン，ラウリルPEG/PPG-18/18メチコン，ポリ（オキシエチレン・オキシプロピレン）メチルポリシロキサン共重合体，ポリオキシエチレン・メチルポリシロキサン共重合体を用いることができる。
It is preferable to use at least a water-soluble modified silicone oil as the surfactant. This has the effect of further improving the stability and antibacterial activity of the antibacterial caulking agent of the present invention.
Water-soluble modified silicone oil (polyether modified silicone) includes PEG-3 methyl ether dimethicone, PEG-9 dimethicone, PEG-10 methyl ether dimethicone, PEG-11 methyl ether dimethicone, PEG12 dimethicone, PEG / PPG-20 / 22. Butyl ether dimethicone, lauryl PEG / PPG-18 / 18 methicone, poly (oxyethylene / oxypropylene) methylpolysiloxane copolymer, polyoxyethylene / methylpolysiloxane copolymer can be used.
本発明において水溶性変性シリコーンオイルに加えて，直鎖アルキルベンゼンスルホン酸ナトリウム，アルキルグリコシド，アルキルアミンオキシド，第四級アンモニウム塩，ポリオキシエチレンアルキルエーテル，ポリエチレングリコールアルキルエーテルのいずれか又は複数を用いることが好ましい。これにより，本発明の抗菌性コーキング剤の安定性ならびに抗菌力をより向上させる効果を有する。 In the present invention, in addition to the water-soluble modified silicone oil, one or more of linear alkylbenzene sulfonate sodium, alkyl glycoside, alkylamine oxide, quaternary ammonium salt, polyoxyethylene alkyl ether, and polyethylene glycol alkyl ether shall be used. Is preferable. This has the effect of further improving the stability and antibacterial activity of the antibacterial caulking agent of the present invention.
ポリエチレングリコールアルキルエーテルとしては，例えば，ポリエチレングリコールモノ－２－エチルヘキシルエーテル，ポリエチレングリコールモノオクチルエーテル，ポリエチレングリコールモノデシルエーテル，ポリエチレングリコールモノドデシルエーテル，ポリエチレングリコールモノテトラデシルエーテルなどを用いることができる。
直鎖アルキルベンゼンスルホン酸ナトリウムとしては，例えば，デシルベンゼンスルホン酸ナトリウム，ドデシルベンゼンスルホン酸ナトリウムなど，炭素数が8～22の直鎖アルキル鎖を有するベンゼンスルホン酸ナトリウムを用いることができる。
アルキルグリコシドとしては，例えば，オクチルグルコシド，デシルグルコシド，ラウリルグルコシドなど，炭素数が8～22，より好ましくは炭素数が8～12のアルキルグリコシドを用いることができる。
アルキルアミンオキシドとしては，例えば，ラウリルジメチルアミンオキシドなど炭素数が8～22のアルキル基を有するアミンオキシドなどを用いることができる。
ポリオキシエチレンアルキルエーテルとしては，例えば，ポリオキシエチレンベヘニルエーテル，ポリオキシエチレンラウリルエーテル，ポリオキシエチレントリデシルエーテルなど，炭素数が8～22のポリオキシエチレンアルキルエーテルなどを用いることができる。
ポリエチレングリコールアルキルエーテルとしては，例えば，ジエチレングリコールモノメチルエーテル，ジエチレングリコールモノエチルエーテル，ジエチレングリコールモノブチルエーテル，ジエチレングリコールジメチルエーテル，ジエチレングリコールジエチルエーテル，ジエチレングリコールブチルエーテル，ジエチレングリコールメチルエチルエーテル，トリエチレングリコールモノメチルエーテル，トリエチレングリコールモノエチルエーテルなどを用いることができる。
第四級アンモニウム塩としては例えば，塩化ベンザルコニウム，塩化ベンゼトニウム，塩化メチルベンゼトニウム，塩化セチルピリジニウム，セトリモニウム，塩化ドファニウム，臭化テトラエチルアンモニウム，塩化ジデシルジメチルアンモニウム，臭化ドミフェン，直鎖アルキルベンゼンスルホン酸ナトリウム，アルキルグリコシド，アルキルアミンオキシド，塩化ジアルキルジメチルアンモニウム，ポリオキシエチレンアルキルエーテル，塩化アルキルトリメチルアンモニウム，塩化ヘキサデシルトリメチルアンモニウム，塩化ベヘニルトリメチルアンモニウム，トリ(オキシエチレン)メチルアンモニウム塩メチルサルフェートの脂肪酸エステル，塩化ジヤシアルキルジメチルアンモニウム，塩化ジアルキルジメチルアンモニウム，塩化ジ硬化牛脂アルキルジメチルアンモニウム，ヘキサデシルトリメチルアンモニウムメトサルフェート塩，ジデシルジメチルアンモニウムメトサルフェート，塩化ヤシアルキルビス(2-ヒドロキシ エチル)メチルアンモニウム，塩化ポリオキシエチレンヤシ アルキルメチルアンモニウム，塩化オレイルビス(2-ヒドロキシ エチル)メチルアンモニウム，テトラメチルアンモニウムクロライド，テトラプロピルアンモニウムハイドロオキサイド，テトラブチルアンモニウムブロマイド，テトラブチルアンモニウムハイドロ オキサイド，トリメチルフェニルアンモニウム クロライド，ベンジルトリメチルアンモニウムクロライド，ベンジルトリエチルアンモニウムクロライド，ベンジルトリブチルアンモニウムクロライドのいずれかから選択することができる。好適には，塩化ベンザルコニウムを0.2%以下の濃度で用いることができる。
As the polyethylene glycol alkyl ether, for example, polyethylene glycol mono-2-ethylhexyl ether, polyethylene glycol monooctyl ether, polyethylene glycol monodecyl ether, polyethylene glycol monododecyl ether, polyethylene glycol monotetradecyl ether and the like can be used.
As the sodium linear alkylbenzene sulfonate, for example, sodium benzenesulfonate having a linear alkyl chain having 8 to 22 carbon atoms, such as sodium decylbenzenesulfonate and sodium dodecylbenzenesulfonate, can be used.
As the alkyl glucoside, for example, an alkyl glucoside having 8 to 22 carbon atoms, more preferably 8 to 12 carbon atoms, such as octyl glucoside, decyl glucoside, and lauryl glucoside, can be used.
As the alkylamine oxide, for example, an amine oxide having an alkyl group having 8 to 22 carbon atoms such as lauryldimethylamine oxide can be used.
As the polyoxyethylene alkyl ether, for example, polyoxyethylene behenyl ether, polyoxyethylene lauryl ether, polyoxyethylene tridecyl ether, and the like, polyoxyethylene alkyl ether having 8 to 22 carbon atoms can be used.
Examples of the polyethylene glycol alkyl ether include diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, diethylene glycol monobutyl ether, diethylene glycol dimethyl ether, diethylene glycol diethyl ether, diethylene glycol butyl ether, diethylene glycol methyl ethyl ether, triethylene glycol monomethyl ether, and triethylene glycol monoethyl ether. Can be used.
Examples of the quaternary ammonium salt include benzalkonium chloride, benzethonium chloride, methylbenzethonium chloride, cetylpyridinium chloride, cetrimonium, dofanium chloride, tetraethylammonium bromide, didecyldimethylammonium chloride, domiphen bromide, and linear alkylbenzene sulfone. Fatty acid ester of sodium acid, alkyl glycoside, alkylamine oxide, dialkyldimethylammonium chloride, polyoxyethylene alkyl ether, alkyltrimethylammonium chloride, hexadecyltrimethylammonium chloride, behenyltrimethylammonium chloride, tri (oxyethylene) methylammonium salt methylsulfate , Didecylalkyldimethylammonium chloride, Dialkyldimethylammonium chloride, Di-cured cowfat alkyldimethylammonium chloride, Hexadecyltrimethylammonium metosulfate salt, Didecyldimethylammonium metosulfate, Palm alkylbis (2-hydroxyethyl) methylammonium chloride, Chloride Polyoxyethylene palm Alkylmethylammonium, oleylbis (2-hydroxyethyl) methylammonium, tetramethylammonium chloride, tetrapropylammonium hydroxide, tetrabutylammonium bromide, tetrabutylammonium hydroxide, trimethylphenylammonium chloride, benzyltrimethylammonium chloride , Benzyltriethylammonium chloride, benzyltributylammonium chloride can be selected. Preferably, benzalkonium chloride can be used at a concentration of 0.2% or less.
本発明において溶媒は，好ましくは水性溶媒を用いる。水性溶媒として，典型的には水を用いればよく，必要に応じて，微量の有機溶媒を含むことができる。有機溶媒を用いる際には，水性溶媒との混和が可能な両親媒性有機溶媒を用いればよく，例えば，メタノール，エタノール，プロパノール，イソプロピルアルコール，テトラヒドロフラン，アセトン，エチルメチルケトン，アセトニトリル，DMF，HMPA，トリエチルアミン，DMSOなどを用いることができ，好ましくは，メタノール，エタノール，プロパノール，イソプロピルアルコールを用いることができる。 In the present invention, the solvent is preferably an aqueous solvent. Water may be typically used as the aqueous solvent, and a trace amount of organic solvent can be contained if necessary. When using an organic solvent, an amphoteric organic solvent that can be mixed with an aqueous solvent may be used, for example, methanol, ethanol, propanol, isopropyl alcohol, tetrahydrofuran, acetone, ethylmethylketone, acetonitrile, DMF, HMPA. , Triethylamine, DMSO and the like can be used, preferably methanol, ethanol, propanol and isopropyl alcohol.
本発明においてアミノ基含有有機酸化合物をさらに含むことが好ましい。これにより，本発明の抗菌性コーティング剤の安定性を向上させるとともに，抗菌力を向上させる効果を有する。
本発明において，アミノ基含有有機酸化合物とは，一つの分子内にアミノ基と有機酸官能基を有する有機化合物として定義される。また，有機酸官能基としては特に限定する必要はなく，例えば，カルボキシル基，リン酸基などが挙げられる。
In the present invention, it is preferable to further contain an amino group-containing organic acid compound. This has the effect of improving the stability of the antibacterial coating agent of the present invention and improving the antibacterial activity.
In the present invention, the amino group-containing organic acid compound is defined as an organic compound having an amino group and an organic acid functional group in one molecule. The organic acid functional group is not particularly limited, and examples thereof include a carboxyl group and a phosphoric acid group.
アミノ基含有有機酸化合物が，天然アミノ酸，リボ核酸，またはこれらの塩のいずれか又は複数から選択されることが好ましい。これにより，アミノ基含有有機酸化合物を，汎用性が高く，かつ，有効性が期待できる化合物として選択することが容易となり，本発明の有用性ならびに経済性を向上させる効果を有する。 The amino group-containing organic acid compound is preferably selected from one or more of natural amino acids, ribonucleic acids, or salts thereof. This makes it easy to select an amino group-containing organic acid compound as a compound that is highly versatile and can be expected to be effective, and has the effect of improving the usefulness and economic efficiency of the present invention.
天然アミノ酸としては，天然アミノ酸である限り特に限定する必要はなく，種々の天然アミノ酸を選択することができる。好ましくは塩基性の天然アミノ酸を選択することができ，最も好ましくは，アルギニン酸とすることができる。 The natural amino acid is not particularly limited as long as it is a natural amino acid, and various natural amino acids can be selected. A basic natural amino acid can be preferably selected, and most preferably arginic acid.
リボ核酸としては，リボ核酸である限り特に限定する必要はなく，種々のリボ核酸を選択することができる。好ましくは，イノシン酸，グアニル酸，ないし，これらの塩を用いることができ，最も好ましくはイノシン酸Na又はグアニル酸Naとすることができる。 The ribonucleic acid is not particularly limited as long as it is a ribonucleic acid, and various ribonucleic acids can be selected. Preferably, inosinic acid, guanylic acid, or a salt thereof can be used, and most preferably Na inosinic acid or Na guanylate can be used.
本発明について，実施例を挙げて詳述する。 The present invention will be described in detail with reference to examples.
＜＜実験１＞＞
＜目的＞
本発明の抗菌性コーティング剤の抗菌性能を評価することを目的に実験を行った。
<<
<Purpose>
An experiment was conducted for the purpose of evaluating the antibacterial performance of the antibacterial coating agent of the present invention.
＜方法＞
１．表の成分比率に従い，各試験液の作製を行った。なお，エトキシシランとしてはH2N（CH2）2NH（CH2）3Si（OC2H5）3を，水溶性シリコンとしては，ポリ（オキシエチレン・オキシプロピレン）メチルポリシロキサン共重合体を用いた。
２．各試験液について，液塗布時の性能として，乾燥性と被膜形成性の評価を行った。また，乾燥後の被膜性能について，耐久性，外観，表面摩擦，抗菌性の評価を行った。
1. 1. Each test solution was prepared according to the component ratios in the table. The ethoxysilane is H 2 N (CH 2 ) 2 NH (CH 2 ) 3 Si (OC 2 H 5 ) 3 , and the water-soluble silicon is a poly (oxyethylene / oxypropylene) methylpolysiloxane copolymer. Was used.
2. 2. For each test solution, the drying property and film forming property were evaluated as the performance when the solution was applied. In addition, the durability, appearance, surface friction, and antibacterial properties of the film after drying were evaluated.
＜結果１，液塗布時性能評価＞
１．液塗布時の性能評価を行った結果を，図１に示す。図中，各項目については，下記の通り，評価を行った。
(1) 乾燥性（塗布そのまま）
各試験液20μLを，0.5mmφノズル径より，透明アクリル板滴下し，23±2℃雰囲気で自然乾燥を行った。滴下後，１２時間以内に乾燥したものを〇，24時間以内に乾燥したものを△，48時間以内に乾燥したものを×として評価を行った。
(2) 乾燥性（直拭取後）
各試験液20μLを，0.5mmφノズル径より，透明アクリル板滴下し，塗布した試験液をヘラで伸ばし3分放置後に，キッチンペーパーで液分をふき取った後，23±2℃雰囲気で自然乾燥時間を行った。その後，１分以内に乾燥したものを〇，３分以内に乾燥したものを△，乾燥に５分以上かかったものを×として評価を行った。
(3) 塗布被膜形成（塗布そのまま）
(1)に準じて自然乾燥後，皮膜形成性を，目視で確認できるものを〇，目視で確認できないものを×として評価を行った。
(4) 塗布皮膜抵抗性（直拭取後）
(2)に準じて自然乾燥後，未塗布部に比べ非常に抵抗が少ないものを◎，未塗布部に比べ抵抗が少ないものを〇，未塗布部に比べ抵抗がやや少ないものを△，未塗布部と抵抗が同じものを×として評価を行った。
<
1. 1. Figure 1 shows the results of performance evaluation during liquid application. In the figure, each item was evaluated as follows.
(1) Dryness (as applied)
20 μL of each test solution was dropped on a transparent acrylic plate from a nozzle diameter of 0.5 mmφ, and air-dried in an atmosphere of 23 ± 2 ° C. After the dropping, those dried within 12 hours were evaluated as 〇, those dried within 24 hours were evaluated as Δ, and those dried within 48 hours were evaluated as ×.
(2) Dryness (after direct wiping)
20 μL of each test solution is dropped from a 0.5 mmφ nozzle diameter on a transparent acrylic plate, the applied test solution is spread with a spatula, left for 3 minutes, wiped off with kitchen paper, and then naturally dried in an atmosphere of 23 ± 2 ° C. Was done. Then, those dried within 1 minute were evaluated as 0, those dried within 3 minutes were evaluated as Δ, and those dried within 5 minutes were evaluated as ×.
(3) Coating film formation (coating as it is)
After natural drying according to (1), the film-forming property was evaluated as 〇 for those that could be visually confirmed and × for those that could not be visually confirmed.
(4) Coating film resistance (after direct wiping)
After natural drying according to (2), the one with very low resistance compared to the uncoated part is ◎, the one with less resistance than the uncoated part is 〇, the one with slightly less resistance than the uncoated part is △, not yet Those having the same resistance as the coated part were evaluated as x.
２．液滴を滴下しそのままの状態においては，乾燥の程度に違いは生じず，いずれも12時間以上の乾燥時間がかかるとともに，いずれの実験例においても被膜の形成が確認された。
３．一方，キッチンペーパーでふき取ったものでは，実験例１ならびに実験例２では，そも被膜の形成が確認できなかった。一方，実験例３ならびに実験例４において1分以内の乾燥と被膜の形成が確認された。
2. 2. There was no difference in the degree of drying when the droplets were dropped and left as they were, and it took 12 hours or more to dry, and the formation of a film was confirmed in all the experimental examples.
3. 3. On the other hand, in the case of wiping with kitchen paper, the formation of a film could not be confirmed in Experimental Example 1 and Experimental Example 2. On the other hand, in Experimental Example 3 and Experimental Example 4, drying within 1 minute and formation of a film were confirmed.
＜結果２，被膜性能評価＞
１．被膜性能の評価において，図中，各項目については，下記の通り，評価を行った。
(1) 塗布皮膜耐久性
「(1) 乾燥性（塗布液的そのまま）」に準じて作製したアクリル板について，塗布面をキッチンペーパー5回拭取しても形成膜が剥離しないものを〇，塗布面をキッチンペーパー3回以内拭取で形成膜が剥離するものを△，塗布面をキッチンペーパー1回拭取で形成膜が剥離したものを×として評価を行った。
(2) 塗布被膜形成色目
「(1) 乾燥性（塗布液的そのまま）」に準じて作製したアクリル板について，未塗布面と同じ透明性なものを◎，若干薄曇りが確認されるものを〇，白化ブリードが確認されるものを△，黒～茶色の着色が確認されるものを×として評価を行った。
(3) 易滑性
「(2) 乾燥性（直拭取後）」に準じて作製したアクリル板の表面において，散布粉末残が少なく，塗布面の易滑性が高いものを◎，散布粉末取れやすく，塗布面が易滑性高いものを○，塗布面滑性があるものを△，未塗布面と同じで滑性はなく粉末付着が大きいものを×として評価を行った。
(4) 塗布面抗菌性
作製されたアクリル片5cm×5cmに，カンジダ・アルビカンスの希釈液105CFU/mLを50μL滴下し，菌の作用時間（1分，10分，30分）に，アクリル板表面の菌を回収し，恒温槽35℃で48時間培養した。培養後，繁殖した検体の有無により抗菌性の判定を行った。即効性の評価については，作用時間の短さにより，◎は1分，○は10分，△は30分，×は抗菌性なしとした。持続性の評価については，塗布後20時間において同様の操作を行い，抗菌性が確認されたものを○，抗菌性が確認されないものを×とした。
<Result 2, film performance evaluation>
1. 1. In the evaluation of film performance, each item in the figure was evaluated as follows.
(1) Durability of coated film For acrylic plates prepared according to "(1) Dryness (as is as coated liquid)", those in which the formed film does not peel off even if the coated surface is wiped with
(2) Acrylic plate produced according to the coating film formation color "(1) Dryness (as it is as a coating liquid)", the one that is as transparent as the uncoated surface is ◎, and the one that is slightly cloudy is confirmed. ， Whitening bleed was confirmed as Δ, and black to brown coloring was confirmed as ×.
(3) Easy slipperiness On the surface of the acrylic plate prepared according to "(2) Dryness (after direct wiping)", the one with less spray powder residue and high slipperiness on the coated surface is ◎, spray powder. Those that were easy to remove and had a high slipperiness on the coated surface were evaluated as ◯, those that were slippery on the coated surface were evaluated as Δ, and those that were the same as the uncoated surface and had no slipperiness and had large powder adhesion were evaluated as ×.
(4) Antibacterial property on the coated surface 50 μL of Candida albicans diluted solution 10 5 CFU / mL was dropped onto the prepared
２．塗布被膜耐久性の結果を図７左に示す。
(1) 実験例１ならびに実験例２では，液滴そのままにおいて，被膜が1回のふき取りにより剥離していた。
(2) 一方，実験例３ならびに実験例４では，液滴そのままならびに直拭取後，いずれにおいても，5回のふき取りでも被膜は剥離せず，維持されていた。
(3) これらの結果から，実験例１ならびに実験例２においては，被膜は形成されるものの，拭き取りにより剥離する弱い被膜である一方，実験例３ならびに４においては，被膜が形成されるとともに拭き取りによる耐久性において優れた被膜であることが分かった。
2. 2. The results of coating film durability are shown on the left side of FIG. 7.
(1) In Experimental Example 1 and Experimental Example 2, the coating film was peeled off by a single wiping with the droplet as it was.
(2) On the other hand, in Experimental Example 3 and Experimental Example 4, the coating was not peeled off and was maintained even after 5 times of wiping in both the droplet as it was and after direct wiping.
(3) From these results, in Experimental Example 1 and Experimental Example 2, although a film is formed, it is a weak film that peels off by wiping, whereas in Experimental Examples 3 and 4, a film is formed and wiped off. It was found that the film was excellent in durability.
３．同様に，塗布被膜形成外観の結果を，図７右に示す。
(1) 実験例１では，試験を行ったアクリル板が着色（茶～黒）しており，酸化銀由来の着色をしていると推定された。
(2) 実験例２においては，アクリル板が白化しており，銀が何らかの理由で凝固し粒子化した色に着色していると推定された。
(3) 実験例３ならびに実験例４においては，被膜は透明であり，アクリル板本来の外観を損なうことはなかった。
(4) これらの結果から，実験例３ならびに実験例４においては，塗布対象物の外観を損なわない，透明な被膜形成が可能であることが分かった。
3. 3. Similarly, the results of the coating film formation appearance are shown on the right side of FIG. 7.
(1) In Experimental Example 1, the acrylic plate tested was colored (brown to black), and it was presumed that the color was derived from silver oxide.
(2) In Experimental Example 2, it was presumed that the acrylic plate was whitened and silver was solidified and colored into particles for some reason.
(3) In Experimental Example 3 and Experimental Example 4, the coating film was transparent and did not impair the original appearance of the acrylic plate.
(4) From these results, it was found that in Experimental Example 3 and Experimental Example 4, a transparent film can be formed without impairing the appearance of the object to be coated.
４．易滑性の結果を，図３左に示す。
(1) 実験例１ならびに実験例２においては，被膜が形成されないため，評価は行っていない。
(2) 実験例３では，表面上のざらつきはあるものの，使用に足る十分な易滑性を有していた。
(3) 実験例４では，表面上のざらつきもなく，極めて優れた易滑性を有していた。
4. The results of I Ching are shown on the left side of FIG.
(1) In Experimental Example 1 and Experimental Example 2, no film was formed, so no evaluation was performed.
(2) In Experimental Example 3, although the surface was rough, it had sufficient slipperiness for use.
(3) In Experimental Example 4, there was no roughness on the surface, and it had extremely excellent slipperiness.
５．抗菌性の結果を，図３右に示す。
(1) 実験例１ならびに実験例２においては，被膜が形成されないため，評価は行っていない。
(2) 実験例３では，10分のサンプルで抗菌が確認されるとともに，抗菌作用は20時間においても発揮されていた。
(3) 実験例４では，1分のサンプルで抗菌が確認されるとともに，抗菌作用は20時間においても発揮されていた。
5. The results of antibacterial properties are shown on the right side of FIG.
(1) In Experimental Example 1 and Experimental Example 2, no film was formed, so no evaluation was performed.
(2) In Experimental Example 3, antibacterial activity was confirmed in a 10-minute sample, and the antibacterial activity was exhibited even in 20 hours.
(3) In Experimental Example 4, antibacterial activity was confirmed in a 1-minute sample, and the antibacterial activity was exhibited even after 20 hours.
＜＜実験２，抗菌性コーティング剤の抗菌性能評価＞＞
＜目的＞
本発明の抗菌性コーティング剤について抗菌性能を調べることを目的に実験を行った。
<< Experiment 2, Evaluation of antibacterial performance of antibacterial coating agent >>
<Purpose>
An experiment was conducted for the purpose of investigating the antibacterial performance of the antibacterial coating agent of the present invention.
＜方法＞
１．樹脂性化合物として，メトキシ基を有する加水分解性シリル化合物を用い，塩化ベンザルコニウムをカップリングさせた樹脂性化合物（[3-(トリメトキシシリル)プロピル]ジメチル(オクタデシル)アミニウム クロリド）を用いた。これを有効成分として，下記の実験例ならびに比較例を用いた。
なお，比較例２ならびに３については，第四級アンモニウム塩ならびに加水分解性シリル化合物は含まれておらず，一般的に用いられる抗菌性塗膜剤の比較対象として用いた。
(1) 実験例５
第四級アンモニウムオルガノシノラン化合物（樹脂性化合物） 41%
銀水溶液 100ppm
メタノール 59%
(2) 比較例１
第四級オルガノシノラン化合物（樹脂性化合物） 41%
メタノール 59%
(3) 比較例２ 酸化チタン系塗膜剤
(4) 比較例３ 銀水溶液
<Method>
1. 1. As the resinous compound, a hydrolyzable silyl compound having a methoxy group was used, and a resinous compound ([3- (trimethoxysilyl) propyl] dimethyl (octadecyl) aminium chloride) coupled with benzalkonium chloride was used. .. Using this as an active ingredient, the following experimental examples and comparative examples were used.
Note that Comparative Examples 2 and 3 did not contain a quaternary ammonium salt and a hydrolyzable silyl compound, and were used as comparison targets for commonly used antibacterial coating agents.
(1) Experimental example 5
Quaternary Ammonium Organosinolan Compound (Resin Compound) 41%
Silver aqueous solution 100ppm
Methanol 59%
(2) Comparative Example 1
Fourth Organosinolan Compound (Resin compound) 41%
Methanol 59%
(3) Comparative Example 2 Titanium oxide-based coating agent
(4) Comparative Example 3 Silver aqueous solution
２．実験例５又は比較例の液体をステンレス板に塗布し，乾燥させた後，試験板とした。当該試験板へ手指接触を行い，接触２時間後，カンジタ菌をたらした後，板表面の菌を，細菌培養を４８時間行い，菌数の測定を行った。なお，陽性コントロールとして，液体を塗布しないステンレス板で同様の操作（手指接触なし）を行った。 2. 2. The liquid of Experimental Example 5 or Comparative Example was applied to a stainless steel plate, dried, and then used as a test plate. The test plate was contacted with fingers, and 2 hours after the contact, the candidiasis was spilled, and then the bacteria on the surface of the plate were cultured for 48 hours, and the number of the bacteria was measured. As a positive control, the same operation (without finger contact) was performed on a stainless steel plate to which no liquid was applied.
＜結果＞
１．結果を図４から図７に示す。
(1) 比較例１において，手指接触がない場合は100%の除菌率であったが，手指接触により，除菌率が45.9%まで下がっていた（図５）。
(2) 比較例２において，手指接触がない場合は100%の除菌率であったが，手指接触により，除菌率が1.6%まで下がっていた（図６）。
(3) 比較例３において，手指接触がない場合は100%の除菌率であったが，手指接触により，除菌率が11.1%まで下がっていた（図７）。
(4) 一方，実験例５では，手指接触の有無にかかわらず，全てのサンプルで，除菌率が99.9%を超えていた。
(5) すなわち，全ての比較例において，手指接触による皮膜の剥離ないし除菌物質の効能低下により，除菌効果自体が減衰していることが確認された。一方，実施例では，手指接触による除菌効果の減衰は確認できなかった。
２．これらの結果から，実験例５では，安定的かつ持続的な抗菌作用の発揮が確認された。
<Result>
1. 1. The results are shown in FIGS. 4 to 7.
(1) In Comparative Example 1, the sterilization rate was 100% when there was no finger contact, but the sterilization rate dropped to 45.9% due to finger contact (Fig. 5).
(2) In Comparative Example 2, the sterilization rate was 100% when there was no finger contact, but the sterilization rate dropped to 1.6% due to finger contact (Fig. 6).
(3) In Comparative Example 3, the sterilization rate was 100% when there was no finger contact, but the sterilization rate dropped to 11.1% due to finger contact (Fig. 7).
(4) On the other hand, in Experimental Example 5, the sterilization rate exceeded 99.9% in all samples regardless of the presence or absence of finger contact.
(5) That is, in all the comparative examples, it was confirmed that the sterilizing effect itself was attenuated due to the peeling of the film due to finger contact or the decrease in the efficacy of the sterilizing substance. On the other hand, in the examples, the attenuation of the sterilization effect due to finger contact could not be confirmed.
2. 2. From these results, it was confirmed that in Experimental Example 5, stable and long-lasting antibacterial action was exhibited.
公共交通機関，公共施設における手指接触頻度の高い箇所への抗菌性処理が可能となる。
Antibacterial treatment is possible for places where finger contact is frequent in public transportation and public facilities.
Claims (11)
抗菌性金属と，
界面活性剤と，
溶媒とからなることを特徴とする抗菌性コーティング剤。
Hydrolytic silyl compound and
Antibacterial metal and
Surfactants and
An antibacterial coating agent characterized by being composed of a solvent.
The antibacterial coating agent according to claim 1, which contains at least a water-soluble modified silicone oil as a surfactant.
Water-soluble modified silicone oils are PEG-3 methyl ether dimethicone, PEG-9 dimethicone, PEG-10 methyl ether dimethicone, PEG-11 methyl ether dimethicone, PEG12 dimethicone, PEG / PPG-20 / 22 butyl ether dimethicone, lauryl PEG / PPG. -18/18 The antibacterial property according to claim 1 or 2, which is selected from one or more of methicone, poly (oxyethylene / oxypropylene) methylpolysiloxane copolymer, and polyoxyethylene / methylpolysiloxane copolymer. Coating agent.
3. Antibacterial coating agent described in Crab.
A claim in which the polyethylene glycol alkyl ether is selected from one or more of polyethylene glycol mono-2-ethylhexyl ether, polyethylene glycol monooctyl ether, polyethylene glycol monodecyl ether, polyethylene glycol monododecyl ether, and polyethylene glycol monotetradecyl ether. The antibacterial coating agent according to 5.
The antibacterial coating agent according to any one of claims 1 to 5, further comprising an amino acid organic compound.
The antibacterial coating agent according to claim 6, wherein the amino acid organic compound is selected from guanylic acid, inosinic acid, or one or a plurality of salts thereof.
The antibacterial coating agent according to claim 7, wherein the amino acid organic compound is sodium guanylate.
The hydrolyzable silyl compound is a hydroxyl group, hydrogen, halogen atom, alkoxy group, dialkoxy group, trialkoxy group, acyloxy group, ketoximate group, amino group, amide group, acid amide group, aminooxy group, mercapto group, alkenyloxy. The antibacterial coating agent according to any one of claims 1 to 8, which is selected from a hydrolyzable silyl compound having any of a group, an n-propoxy group and an isopropoxy group.
The antibacterial coating agent according to claim 9, wherein the hydrolyzable silyl compound is selected from the hydrolyzable silyl compounds having either a methoxy group or an ethoxy group.
Claims that the antibacterial metal is selected from one or more of gold, silver, copper, platinum, zinc, titanium, tungsten, nickel, iron, tin, mercury, palladium, aluminum, cobalt, molybdenum, lead, vanadium, zirconium. Item 2. The antibacterial coating agent according to any one of Items 1 to 10.
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