JPH06506197A - Oral and body hygiene articles containing an active agent bound to a surface - Google Patents
Oral and body hygiene articles containing an active agent bound to a surfaceInfo
- Publication number
- JPH06506197A JPH06506197A JP4505234A JP50523492A JPH06506197A JP H06506197 A JPH06506197 A JP H06506197A JP 4505234 A JP4505234 A JP 4505234A JP 50523492 A JP50523492 A JP 50523492A JP H06506197 A JPH06506197 A JP H06506197A
- Authority
- JP
- Japan
- Prior art keywords
- article
- activator
- propyl
- active agent
- group
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- 239000013543 active substance Substances 0.000 title claims description 35
- 238000000034 method Methods 0.000 claims description 24
- 239000012190 activator Substances 0.000 claims description 22
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 claims description 18
- 229920000642 polymer Polymers 0.000 claims description 18
- 239000000463 material Substances 0.000 claims description 17
- 150000003856 quaternary ammonium compounds Chemical group 0.000 claims description 15
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 12
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 12
- -1 2-(3-trimethoxysilylpropyl) (trimethoxysilylpropyl)-N-cetylpyridinium bromide Chemical compound 0.000 claims description 11
- 125000000217 alkyl group Chemical group 0.000 claims description 11
- 239000002904 solvent Substances 0.000 claims description 11
- 125000004432 carbon atom Chemical group C* 0.000 claims description 10
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical group OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 9
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 9
- 235000019270 ammonium chloride Nutrition 0.000 claims description 9
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 9
- 239000000203 mixture Substances 0.000 claims description 9
- 229940027983 antiseptic and disinfectant quaternary ammonium compound Drugs 0.000 claims description 8
- 239000003960 organic solvent Substances 0.000 claims description 7
- 239000000126 substance Substances 0.000 claims description 7
- 229920008347 Cellulose acetate propionate Polymers 0.000 claims description 6
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 5
- 241000628997 Flos Species 0.000 claims description 5
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 5
- 239000002253 acid Substances 0.000 claims description 5
- 229910001854 alkali hydroxide Inorganic materials 0.000 claims description 5
- 150000008044 alkali metal hydroxides Chemical class 0.000 claims description 5
- 150000007524 organic acids Chemical class 0.000 claims description 5
- 239000002861 polymer material Substances 0.000 claims description 5
- QLNOVKKVHFRGMA-UHFFFAOYSA-N trimethoxy(propyl)silane Chemical group [CH2]CC[Si](OC)(OC)OC QLNOVKKVHFRGMA-UHFFFAOYSA-N 0.000 claims description 5
- 235000010585 Ammi visnaga Nutrition 0.000 claims description 4
- 244000153158 Ammi visnaga Species 0.000 claims description 4
- 239000004677 Nylon Substances 0.000 claims description 4
- 239000004952 Polyamide Substances 0.000 claims description 4
- 150000001450 anions Chemical group 0.000 claims description 4
- 229920002678 cellulose Polymers 0.000 claims description 4
- 150000001875 compounds Chemical class 0.000 claims description 4
- 229920001577 copolymer Polymers 0.000 claims description 4
- 150000007522 mineralic acids Chemical class 0.000 claims description 4
- 229920001778 nylon Polymers 0.000 claims description 4
- 229920002647 polyamide Polymers 0.000 claims description 4
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 4
- 239000004793 Polystyrene Substances 0.000 claims description 3
- XECAHXYUAAWDEL-UHFFFAOYSA-N acrylonitrile butadiene styrene Chemical compound C=CC=C.C=CC#N.C=CC1=CC=CC=C1 XECAHXYUAAWDEL-UHFFFAOYSA-N 0.000 claims description 3
- 229920000122 acrylonitrile butadiene styrene Polymers 0.000 claims description 3
- 239000004676 acrylonitrile butadiene styrene Substances 0.000 claims description 3
- 210000001520 comb Anatomy 0.000 claims description 3
- 239000011521 glass Substances 0.000 claims description 3
- 210000004209 hair Anatomy 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
- 229920000728 polyester Polymers 0.000 claims description 3
- 229920002223 polystyrene Polymers 0.000 claims description 3
- 150000001768 cations Chemical group 0.000 claims description 2
- 239000001913 cellulose Substances 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 150000002367 halogens Chemical class 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 150000004679 hydroxides Chemical class 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- 229920000058 polyacrylate Polymers 0.000 claims description 2
- AFVRTALJBDPNPY-UHFFFAOYSA-N [amino(sulfanyl)methylidene]-(3-trimethoxysilylpropyl)azanium;chloride Chemical group [Cl-].CO[Si](OC)(OC)CCC[NH+]=C(N)S AFVRTALJBDPNPY-UHFFFAOYSA-N 0.000 claims 2
- PHDAZHGCTGTQAS-UHFFFAOYSA-M dimethyl-tetradecyl-(3-trimethoxysilylpropyl)azanium;chloride Chemical compound [Cl-].CCCCCCCCCCCCCC[N+](C)(C)CCC[Si](OC)(OC)OC PHDAZHGCTGTQAS-UHFFFAOYSA-M 0.000 claims 2
- 229920001296 polysiloxane Polymers 0.000 claims 2
- ZZQRGVPRICULAJ-UHFFFAOYSA-M 3-(1-hexadecylpyridin-1-ium-2-yl)propyl-trimethoxysilane;bromide Chemical compound [Br-].CCCCCCCCCCCCCCCC[N+]1=CC=CC=C1CCC[Si](OC)(OC)OC ZZQRGVPRICULAJ-UHFFFAOYSA-M 0.000 claims 1
- GZWRMQNNGRSSNL-UHFFFAOYSA-N 3-trimethoxysilylpropan-1-amine;hydrochloride Chemical compound [Cl-].CO[Si](OC)(OC)CCC[NH3+] GZWRMQNNGRSSNL-UHFFFAOYSA-N 0.000 claims 1
- AVMNFQHJOOYCAP-UHFFFAOYSA-N acetic acid;propanoic acid Chemical compound CC(O)=O.CCC(O)=O AVMNFQHJOOYCAP-UHFFFAOYSA-N 0.000 claims 1
- 239000012633 leachable Substances 0.000 claims 1
- 125000004805 propylene group Chemical class [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 claims 1
- 230000000845 anti-microbial effect Effects 0.000 description 16
- 244000005700 microbiome Species 0.000 description 16
- 210000003128 head Anatomy 0.000 description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- 241000589517 Pseudomonas aeruginosa Species 0.000 description 7
- 241000222122 Candida albicans Species 0.000 description 6
- 241000191967 Staphylococcus aureus Species 0.000 description 6
- 229940095731 candida albicans Drugs 0.000 description 6
- 239000003795 chemical substances by application Substances 0.000 description 6
- 239000000835 fiber Substances 0.000 description 6
- 230000000844 anti-bacterial effect Effects 0.000 description 5
- UDSAIICHUKSCKT-UHFFFAOYSA-N bromophenol blue Chemical compound C1=C(Br)C(O)=C(Br)C=C1C1(C=2C=C(Br)C(O)=C(Br)C=2)C2=CC=CC=C2S(=O)(=O)O1 UDSAIICHUKSCKT-UHFFFAOYSA-N 0.000 description 5
- 238000000576 coating method Methods 0.000 description 5
- 230000001332 colony forming effect Effects 0.000 description 5
- 230000008878 coupling Effects 0.000 description 4
- 238000010168 coupling process Methods 0.000 description 4
- 238000005859 coupling reaction Methods 0.000 description 4
- 239000004744 fabric Substances 0.000 description 4
- 239000002054 inoculum Substances 0.000 description 4
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 4
- 239000000606 toothpaste Substances 0.000 description 4
- 238000011282 treatment Methods 0.000 description 4
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 3
- 239000004599 antimicrobial Substances 0.000 description 3
- NEUSVAOJNUQRTM-UHFFFAOYSA-N cetylpyridinium Chemical class CCCCCCCCCCCCCCCC[N+]1=CC=CC=C1 NEUSVAOJNUQRTM-UHFFFAOYSA-N 0.000 description 3
- 239000008367 deionised water Substances 0.000 description 3
- 229910021641 deionized water Inorganic materials 0.000 description 3
- 230000012010 growth Effects 0.000 description 3
- 238000002386 leaching Methods 0.000 description 3
- 230000000813 microbial effect Effects 0.000 description 3
- 229910000077 silane Inorganic materials 0.000 description 3
- 229940034610 toothpaste Drugs 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical group N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- 239000004743 Polypropylene Substances 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 238000002835 absorbance Methods 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 230000004913 activation Effects 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- 150000001412 amines Chemical group 0.000 description 2
- 238000004140 cleaning Methods 0.000 description 2
- 239000000645 desinfectant Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 210000000214 mouth Anatomy 0.000 description 2
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 description 2
- 239000004033 plastic Substances 0.000 description 2
- 229920003023 plastic Polymers 0.000 description 2
- 229920002285 poly(styrene-co-acrylonitrile) Polymers 0.000 description 2
- 229920001155 polypropylene Polymers 0.000 description 2
- 125000001453 quaternary ammonium group Chemical group 0.000 description 2
- 210000004761 scalp Anatomy 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000004094 surface-active agent Substances 0.000 description 2
- 239000000080 wetting agent Substances 0.000 description 2
- VKVJIWVUYNTBEZ-UHFFFAOYSA-N 1,3-bis(3,5-dichlorophenyl)urea Chemical compound ClC1=CC(Cl)=CC(NC(=O)NC=2C=C(Cl)C=C(Cl)C=2)=C1 VKVJIWVUYNTBEZ-UHFFFAOYSA-N 0.000 description 1
- BIGOJJYDFLNSGB-UHFFFAOYSA-N 3-isocyanopropyl(trimethoxy)silane Chemical group CO[Si](OC)(OC)CCC[N+]#[C-] BIGOJJYDFLNSGB-UHFFFAOYSA-N 0.000 description 1
- LHGMHYDJNXEEFG-UHFFFAOYSA-N 4-[4-(dimethylamino)phenyl]iminocyclohexa-2,5-dien-1-one Chemical compound C1=CC(N(C)C)=CC=C1N=C1C=CC(=O)C=C1 LHGMHYDJNXEEFG-UHFFFAOYSA-N 0.000 description 1
- RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 description 1
- 241000894006 Bacteria Species 0.000 description 1
- 244000007835 Cyamopsis tetragonoloba Species 0.000 description 1
- 241000588722 Escherichia Species 0.000 description 1
- 206010018286 Gingival pain Diseases 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 241000588747 Klebsiella pneumoniae Species 0.000 description 1
- 241001077673 Mylon Species 0.000 description 1
- 229920000297 Rayon Polymers 0.000 description 1
- 229920001057 Silicone quaternary amine Polymers 0.000 description 1
- 206010041235 Snoring Diseases 0.000 description 1
- 101150066742 TRI1 gene Proteins 0.000 description 1
- 239000013504 Triton X-100 Substances 0.000 description 1
- 229920004890 Triton X-100 Polymers 0.000 description 1
- MTTQGUIAKDIICU-UHFFFAOYSA-N [Cl-].[NH4+].C=CC Chemical compound [Cl-].[NH4+].C=CC MTTQGUIAKDIICU-UHFFFAOYSA-N 0.000 description 1
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- LFVVNPBBFUSSHL-UHFFFAOYSA-N alexidine Chemical class CCCCC(CC)CNC(=N)NC(=N)NCCCCCCNC(=N)NC(=N)NCC(CC)CCCC LFVVNPBBFUSSHL-UHFFFAOYSA-N 0.000 description 1
- 230000005791 algae growth Effects 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 125000005370 alkoxysilyl group Chemical group 0.000 description 1
- 150000001413 amino acids Chemical class 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 239000003242 anti bacterial agent Substances 0.000 description 1
- 230000002421 anti-septic effect Effects 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 230000003078 antioxidant effect Effects 0.000 description 1
- 239000003125 aqueous solvent Substances 0.000 description 1
- 230000001580 bacterial effect Effects 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 230000000975 bioactive effect Effects 0.000 description 1
- 239000003124 biologic agent Substances 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 239000001045 blue dye Substances 0.000 description 1
- 229920002301 cellulose acetate Polymers 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000004737 colorimetric analysis Methods 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 239000002537 cosmetic Substances 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- AXPYABZPAWSUMG-UHFFFAOYSA-M didecyl-methyl-(3-trimethoxysilylpropyl)azanium;chloride Chemical compound [Cl-].CCCCCCCCCC[N+](C)(CCC[Si](OC)(OC)OC)CCCCCCCCCC AXPYABZPAWSUMG-UHFFFAOYSA-M 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 238000004043 dyeing Methods 0.000 description 1
- 210000005069 ears Anatomy 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 208000030533 eye disease Diseases 0.000 description 1
- 210000003608 fece Anatomy 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 239000006260 foam Substances 0.000 description 1
- 208000007565 gingivitis Diseases 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- ATADHKWKHYVBTJ-UHFFFAOYSA-N hydron;4-[1-hydroxy-2-(methylamino)ethyl]benzene-1,2-diol;chloride Chemical compound Cl.CNCC(O)C1=CC=C(O)C(O)=C1 ATADHKWKHYVBTJ-UHFFFAOYSA-N 0.000 description 1
- 208000015181 infectious disease Diseases 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 230000002147 killing effect Effects 0.000 description 1
- 229940045505 klebsiella pneumoniae Drugs 0.000 description 1
- 210000003127 knee Anatomy 0.000 description 1
- 239000010985 leather Substances 0.000 description 1
- 230000000670 limiting effect Effects 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 230000005923 long-lasting effect Effects 0.000 description 1
- 210000001161 mammalian embryo Anatomy 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 229920005615 natural polymer Polymers 0.000 description 1
- 210000001331 nose Anatomy 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 125000005375 organosiloxane group Chemical group 0.000 description 1
- 230000001151 other effect Effects 0.000 description 1
- 201000001245 periodontitis Diseases 0.000 description 1
- 230000002085 persistent effect Effects 0.000 description 1
- 239000008194 pharmaceutical composition Substances 0.000 description 1
- 230000007505 plaque formation Effects 0.000 description 1
- 239000001967 plate count agar Substances 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 230000002335 preservative effect Effects 0.000 description 1
- PYNUOAIJIQGACY-UHFFFAOYSA-N propylazanium;chloride Chemical compound Cl.CCCN PYNUOAIJIQGACY-UHFFFAOYSA-N 0.000 description 1
- 239000002964 rayon Substances 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 210000003296 saliva Anatomy 0.000 description 1
- 230000001568 sexual effect Effects 0.000 description 1
- 239000002453 shampoo Substances 0.000 description 1
- 239000008257 shaving cream Substances 0.000 description 1
- 150000004756 silanes Chemical class 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 210000003491 skin Anatomy 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 235000017550 sodium carbonate Nutrition 0.000 description 1
- 238000004659 sterilization and disinfection Methods 0.000 description 1
- 238000004381 surface treatment Methods 0.000 description 1
- 230000002195 synergetic effect Effects 0.000 description 1
- 229920002994 synthetic fiber Polymers 0.000 description 1
- 229920001059 synthetic polymer Polymers 0.000 description 1
- 239000004758 synthetic textile Substances 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- 208000004371 toothache Diseases 0.000 description 1
- 238000002834 transmittance Methods 0.000 description 1
- LFRDHGNFBLIJIY-UHFFFAOYSA-N trimethoxy(prop-2-enyl)silane Chemical group CO[Si](OC)(OC)CC=C LFRDHGNFBLIJIY-UHFFFAOYSA-N 0.000 description 1
- GPRLSGONYQIRFK-MNYXATJNSA-N triton Chemical compound [3H+] GPRLSGONYQIRFK-MNYXATJNSA-N 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
- A01N25/34—Shaped forms, e.g. sheets, not provided for in any other sub-group of this main group
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N55/00—Biocides, pest repellants or attractants, or plant growth regulators, containing organic compounds containing elements other than carbon, hydrogen, halogen, oxygen, nitrogen and sulfur
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Environmental Sciences (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- Pest Control & Pesticides (AREA)
- Agronomy & Crop Science (AREA)
- Zoology (AREA)
- Plant Pathology (AREA)
- Toxicology (AREA)
- Cosmetics (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Detergent Compositions (AREA)
- Eyeglasses (AREA)
- Brushes (AREA)
Abstract
(57)【要約】本公報は電子出願前の出願データであるため要約のデータは記録されません。 (57) [Summary] This bulletin contains application data before electronic filing, so abstract data is not recorded.
Description
【発明の詳細な説明】 活性剤を表面に結合して含有する 口腔および身体衛生物品 発明の概要 本発明は、口腔および身体衛生に用いるのに適し、そしてその表面に一種以上の 化学的または生物学的に活性な剤を結合した、ポリマー材料より成る物品に関す る。[Detailed description of the invention] Contains an active agent bound to a surface Oral and body hygiene products Summary of the invention The present invention is suitable for use in oral and body hygiene and has one or more on its surface. Relating to articles made of polymeric materials bound to chemically or biologically active agents. Ru.
適当な物品のいくつかの例には、眼鏡、コンタクトレンズ、歯ブラシ、つまよう じ、義歯、デンタル・フロス、かみそり、ヘアブラシおよびくしが包含される。Some examples of suitable items include eyeglasses, contact lenses, toothbrushes, and toothpicks. This includes teeth, dentures, dental floss, razors, hairbrushes, and combs.
ポリマー材料は、ポリアミド類、ポリスチレン類、スチレン−アクリロニトリル コポリマー類、アクリロニトリル−ブタジェン−スチレンコポリマー類、ポリア クリレート類、ポリエステル類およびポリプロピレン類、好ましくはナイロンお よびセルロースアセテートプロピオネート、より成る群より選択される。活性剤 は好ましくは第四級アンモニウム化合物、例えば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ンモニウムクロライドなどである。Polymer materials include polyamides, polystyrenes, styrene-acrylonitrile copolymers, acrylonitrile-butadiene-styrene copolymers, polyamide Acrylates, polyesters and polypropylenes, preferably nylon or and cellulose acetate propionate. activator is preferably a quaternary ammonium compound, such as 3-(trimethoxysilyl)propylene. Examples include lopyldimethyloctadecylammonium chloride.
さらに本発明は、（ａ）化学的または生物学的活性剤をポリマー材料より成る口 腔または身体衛生物品の表面に直接永久的に結合するか、または（ｂ）（１）前 記物品を酸、アルカリ水酸化物または有機溶媒と接触させ、そして（２）次に前 記活性剤を前記物品の表面に永久的に結合することによる、前記活性剤のコーテ ィングの前記物品への適用方法にも関する。The present invention further provides for (a) introducing a chemically or biologically active agent into a mouth comprising a polymeric material; directly and permanently attached to the cavity or surface of the body hygiene article, or (b)(1) above. (2) contacting the article with an acid, alkali hydroxide or an organic solvent; Coating the activator by permanently bonding the activator to the surface of the article. It also relates to a method of applying coatings to said articles.
本発明は、抗細菌性および／または抗微生物性コーティングおよび／または歯垢 （プラーク）、歯肉炎、歯根膜炎、歯痛および歯肉痛、および皮膚、頭髪、頭皮 および目の病気および感染症の遅鈍化または予防に有用な活性剤のコーティング を有する口腔および身体衛生物品を提供する。The present invention provides antibacterial and/or antimicrobial coatings and/or plaque (plaque), gingivitis, periodontitis, toothache and gum pain, and skin, hair, and scalp and coatings of active agents useful in slowing or preventing eye diseases and infections. To provide an oral and body hygiene article having the following properties.
発明の背景および情報開示 歯ブラシやデンタル・フロスなどの口腔および身体衛生物品はより効果的な清浄 化およびその他の効果をもとめて常に改良されている。それら効果の一部には、 歯および歯肉への活性剤の送達、および口腔衛生物品の消毒特性が包含される。Background of the invention and information disclosure Oral and body hygiene products such as toothbrushes and dental floss clean more effectively It is constantly being improved to improve its effectiveness and other effects. Some of these effects include Includes delivery of active agents to the teeth and gums, and antiseptic properties of oral hygiene articles.
歯ブラシ、ヘアブラシおよびくしは特に、細菌および／または微生物増殖の温床 となり得るので、それらにおける細菌および／またはその他の微生物の増殖を阻 害しまたは予防する歯ブラシその他の口腔および身体衛生物品を提供することは 特に有益であろう。すなわち、本発明の目的の一つは、−以上の活性剤をその表 面に結合した口腔および身体衛生物品を提供することにある。本発明のもう一つ の目的は、永続的または長期持続性の抗細菌および／または抗微生物活性を有す る口腔および身体衛生物品を提供することにある。本発明のもう一つの目的は、 （ａ）（−以上の）活性剤を口腔または身体衛生物品の表面に直接永久的に結合 するか、または（ｂ）それを酸、アルカリ塩基または有機溶媒と接触させ、そし て次に前記活性剤を前記物品の表面に永久的に結合することによる、前記活性剤 を前記口腔または身体衛生物品に適用するための簡易で効率的な方法を提供する ことにある。Toothbrushes, hairbrushes and combs are particularly hotbeds for bacterial and/or microbial growth. inhibit the growth of bacteria and/or other microorganisms in them. Providing toothbrushes and other oral and personal hygiene products that harm or prevent would be particularly useful. That is, one of the objects of the present invention is to An object of the present invention is to provide an oral and personal hygiene article bonded to a surface. Another aspect of the invention The purpose is to have persistent or long-lasting antibacterial and/or antimicrobial activity. Our objective is to provide oral and body hygiene products that are Another object of the invention is to (a) permanently bonding the active agent (- or more) directly to the surface of the oral or personal hygiene article; or (b) contacting it with an acid, an alkali base or an organic solvent; and then permanently bonding the active agent to the surface of the article. to provide a simple and efficient method for applying said oral or personal hygiene products to said oral or personal hygiene articles. There is a particular thing.
当該技術分野の多くの文献が抗細菌性組成物、およびこれらを各種表面処理に用 いることを記載している。米国特許第４．８６６、１９２号は、レーヨン布およ びその他の表面を処理するための有機シリコーン第四級アンモニウム抗微生物化 合物を記載している。米国特許第４．３７１．５７７号は、アミノ酸型界面活性 剤および有機シリコーン第四級アンモニウム塩で処理された抗微生物性カーペッ トを記載している。米国特許第４．６２１．１２０号は第四級窒素基を有するビ ニルコポリマーより成る抗細菌性組成物を記載している。これらの組成物はうが い液、歯みがきおよびデンタル・クリームに有用であるとして記載されている。Much literature in the art describes antibacterial compositions and their use in various surface treatments. It states that there is. U.S. Patent No. 4.866,192 discloses that rayon fabric and Organosilicone quaternary ammonium antimicrobial treatment for treating and other surfaces Compounds are listed. U.S. Patent No. 4,371,577 discloses amino acid type surfactant antimicrobial carpet treated with agents and organosilicone quaternary ammonium salts. are listed. U.S. Pat. No. 4,621,120 discloses Antibacterial compositions comprising nil copolymers are described. These compositions gargle It has been described as useful in fluids, toothpastes, and dental creams.
米国特許第３．１７０．９０１号は、ぬれ強度、撥水性、および耐ちぢみ性を高 めるための紙および繊維布帛処理に有用な第四級アンモニウム化合物またはその ポリマーを記載している。米国特許第４．０２５．６１７号は、少くとも二つの 二官能性第三級アミンと１．４−ジハロ−２−ブテンの縮合により形成される抗 微生物性第四級アンモニウムコポリマーを記載している。これらのコポリマーは 、循環水および静止水の抗微生物処理に有用であるとして記載ることによる生物 活性セルロース布帛の染色方法を記載されている。U.S. Patent No. 3.170.901 provides improved wet strength, water repellency, and shrink resistance. Quaternary ammonium compounds or their Describes polymers. U.S. Patent No. 4.025.617 includes at least two Antioxidant formed by condensation of difunctional tertiary amine and 1,4-dihalo-2-butene Microbial quaternary ammonium copolymers are described. These copolymers are , organisms by listing them as useful in the antimicrobial treatment of circulating and still water. A method for dyeing activated cellulose fabrics is described.
米国特許第４，４８２．６８０号は、化粧用および薬学的組成物のための保存剤 として、また消毒クレンザ−として有用なポリ（ビニルベンジル第四級アンモニ ウム）ハライドを開示している。米国特許第４．１６１．５１８号は第四級アン モニウム有機シリコーンを含有する歯みがき組成物を記載している。米国特許第 ４．３９４．３７８号は繊維、シリカ實材料、金属、皮、木材およびプラスチッ クなどの抗微生物処理に有用なある種のシリル第四級アンモニウム塩例えば３− （トリメトキシシリル）プロピルジデシルメチルアンモニウムクロライドを記載 している。U.S. Pat. No. 4,482.680 describes a preservative for cosmetic and pharmaceutical compositions. Poly(vinylbenzyl quaternary ammonia) useful as a disinfectant and as a disinfectant cleanser. um) halide is disclosed. U.S. Patent No. 4.161.518 is a quaternary A toothpaste composition containing a monium organosilicone is described. US Patent No. No. 4.394.378 applies to textiles, silica materials, metals, leather, wood and plastics. Certain silyl quaternary ammonium salts, such as 3- (Trimethoxysilyl)propyldidecylmethylammonium chloride is listed. are doing.
米国特許第４．１６１．５１８号は歯垢形成の阻害に有用な第四級アンモニウム 有機シロキサンを含有する歯みがき組成物を記載している。米国特許第４．６１ ５．９３７号は有機シリコーン第四級アンモニウム塩を含有する抗微生物活性ウ ェブおよび湿りふきん（ｗｅｔ ｗｉｐｅ）を記載している。U.S. Pat. No. 4,161,518 describes quaternary ammonium useful in inhibiting plaque formation. A toothpaste composition containing an organosiloxane is described. U.S. Patent No. 4.61 No. 5.937 is an antimicrobial active product containing an organosilicone quaternary ammonium salt. web and wet wipes.
米国特許第４，７２１．５１１号は、生物活性量のシリコーン第四級アミンを有 する抗微生物性布帛を記載している。米国特許第４．２８２．３６６号は、抗微 生物剤としての有機シリコーン第四級アンモニウム化合物で含浸された天然およ び合成布帛を記載している。U.S. Pat. No. 4,721.511 contains a biologically active amount of a silicone quaternary amine. It describes an antimicrobial fabric that has antimicrobial properties. U.S. Pat. No. 4,282,366 discloses antimicrobial Natural and impregnated with organosilicone quaternary ammonium compounds as biological agents and synthetic fabrics.
米国特許第４．６３１．２９７号にはシランの第四級アンモニウム塩を含有する 抗微生物性発泡体の製法が記載されている。米国特許第４．４０８．９９６号は 、有機シリコーンポリマー、色素およびシリル第四級アミンの混合物を適用す本 発明に包含される物品には口腔または身体衛生用にしている。U.S. Pat. No. 4,631,297 contains quaternary ammonium salts of silanes. A method for making antimicrobial foams is described. U.S. Patent No. 4.408.996 is , applying a mixture of organosilicone polymers, dyes and silyl quaternary amines Articles encompassed by the invention are intended for oral or personal hygiene.
米国特許第３．７３０．７０１号は、ある種のシリル第四級アミンを添加するこ とによる水中藻増殖の抑制方法を記載している。米国特許第４．８４７．０８８ 号は、第四級アンモニウム化合物と酸より成るカーペット、布帛、壁および家具 ・備品の処理に有用な、相乗的抗微生物性組成物を記載している。U.S. Pat. No. 3,730,701 describes the addition of certain silyl quaternary amines. It describes methods for suppressing underwater algae growth by U.S. Patent No. 4.847.088 The number refers to carpets, fabrics, walls and furniture made of quaternary ammonium compounds and acids. - Describes synergistic antimicrobial compositions useful in treating supplies.
例えば＋Ｄｉｓｉｎｆｅｃｔｉｏｎ ｏｆ Ｗａｔｅｒ ｗｉｔｈ Ｑｕａｔｅ ｒｎａｒｙ＾ｍｗｏｎｉｕｓ ５ａｌｔｓ Ｉｎ５ｏｌｕｂｉｌｉｚｅｄ ｏｎ ａ Ｐｏｒｏｕｓ ＧｌａｓｓＳｕｒｆａｃｅ”、 Ｎａｋａｇａｗａ ｅｔ ａｌ、Ａｐｐｌｉｅｄ ａｎｄ Ｅｎｖｉｒｏｒｖｅｎ−リリＩｉｃｒｏｂｉ ｏｌｏｇｙ、璽ａｒｃｈ １９８４． ｐ−５１３−５１８；および“＾Ｉｇｉ ｃｉｄａｌ Ａｃｔｉｖｉｔｙ ｏｆ ａ ５ｕｒｆａｃｅ−Ｂｏｎｄｅｄ Ｏ ｒｇａｎｏｓｉ−１ｉｃｏｎｅ Ｑｕａｔｅｒｎａｒｙ Ａｍｓｏｎｉｕｍ Ｃ ｈｌｏｒｉｄｅ”、ｆａｌｔｅｒｓ ｅｔａｌ、Ａｐｐｌｉｅｄ ｌｌｉｃｒｏ ｂｉｏｌｏｇｙ、Ｆｅｂ、１９７３． Ｐ、２５３−２５６などの論文は結合し た第四級アンモニウム塩の抗微生物活性を記載している。For example, +Disinfection of Water with Quant rnary＾mwonius 5 alts In5olubilized on a Porous GlassSurface”, Nakagawa et al, Applied and Envirorven-Lili Iicrobi ology, Seal arch 1984. p-513-518; and “^Igi cidal Activity of a 5 surface-Bonded O rganosi-1icone Quaternary Amsonium C hloride”, falters etal, Applied llicro biology, Feb. 1973. Papers such as P, 253-256 are combined. The antimicrobial activity of quaternary ammonium salts is described.
詳細説明 本発明は（−以上の）活性剤がその表面に結合されるように処理された身体およ び口腔衛生品に関する。詳細には、本発明は、−以上の化学的または生物学的活 性剤をその表面に結合したポリマー材料より成る物品であって、口腔または身体 衛生用途に適しそして前記活性剤が水性媒質（ｗａｔｅｒ−ｂａｓｅｄ ＋ｗｅ ｄｉｕｓ）中で前記物品の表面から実質的に非浸出性であるものに関する。Detailed explanation The present invention relates to a body treated in such a way that an active agent (- or more) is bound to its surface. and oral hygiene products. In particular, the invention relates to - or more chemical or biological activities. An article consisting of a polymeric material having a sexual agent attached to its surface, the article comprising: Suitable for sanitary applications and where the active agent is water-based dius) substantially non-leaching from the surface of the article.
適したいずれの製品も包含される。本明細書に用いられる口腔衛生とは、歯、歯 肉、義歯または口腔のその他の部分を清浄化しそして手入れするのに有用である ことを意味する。本明細書に用いられる身体衛生とは頭髪、頭皮、皮膚、耳、鼻 、目および顔および頭の他の部分を清浄化しそして手入れするのに有用であるこ とを意味する。Any suitable product is included. Oral hygiene as used herein refers to teeth, Useful for cleaning and caring for flesh, dentures or other parts of the oral cavity It means that. As used herein, physical hygiene refers to hair, scalp, skin, ears, nose. , useful for cleaning and caring for the eyes and other parts of the face and head. means.
本発明の範囲に包含される好ましい物品には歯ブラシ、デンタル・フロス、つま ようじ、＜シ、ヘアブラシ、かみそり、眼鏡のレンズおよびフレームおよびコン タクトレンズが包含される。Preferred articles within the scope of this invention include toothbrushes, dental floss, and toothbrushes. Toothpicks, toothbrushes, hairbrushes, razors, eyeglass lenses and frames, and glasses Includes tact lenses.
本発明による適切な物品は、一部または全体がポリマー材料で構成されていても よく、あるいはポリマー材料より成る外部表面を有していてもよい。ポリマー材 料は天然または合成ポリマーであってよい。ポリマー材料は好ましくは、ポリア ミド類、ポリアクリレート類、ポリエステル類、ポリプロピレン類、ポリスチレ ン類、スチレン−アクリロニトリルコポリマー類、アクリロニトリル−ブタジェ ン−スチレンコポリマー類、セルロースエステルおよびそれらのブレンドおよび 組合せである。最も好ましいポリマー材料はマイロンおよびセルロースアセテー トプロピオネートである。Suitable articles according to the invention may be constructed in part or in whole from polymeric materials. It may alternatively have an external surface of polymeric material. polymer material The materials may be natural or synthetic polymers. The polymeric material is preferably polyamide. Mids, polyacrylates, polyesters, polypropylenes, polystyrene styrene-acrylonitrile copolymers, acrylonitrile-butadiene - Styrene copolymers, cellulose esters and blends thereof and It's a combination. The most preferred polymeric materials are mylon and cellulose acetate. Topropionate.
本発明の本質的特徴は、その物品が一以上の化学的または生物学的活性剤をその ポリマー表面に永久的に結合している点である。これらの活性剤は、水性媒質中 で物品表面から実質的に浸出できないように物品のポリマー表面に結合される。An essential feature of the invention is that the article contains one or more chemically or biologically active agents. It is permanently bonded to the polymer surface. These active agents are is bonded to the polymer surface of the article in such a way that it cannot be substantially leached from the surface of the article.
適切な活性剤には抗微生物活性を有し、そして物品のポリマー表面に結合され得 るいずれの化合物も包含される。好ましい活性剤には第四級アンモニウム化合物 、有機シリコーン第四級アンモニウム化合物、セチルピリジニウム化合物、グア ニジン化合物、ビス−グアニジン化合物およびイソチオウロニウムノ１ライド化 合物が包含される。Suitable active agents have antimicrobial activity and can be attached to the polymer surface of the article. Any compound that is included is included. Preferred activators include quaternary ammonium compounds. , organosilicone quaternary ammonium compounds, cetylpyridinium compounds, guar Nidine compounds, bis-guanidine compounds and isothiouronium nitrides compounds are included.
本発明に有用な好ましい第四級アンモニウム化合物は式： （式中、Ｒ１は−Ｃ１１２−フェニルまたは約８〜２２個の炭素原子を含むアル キル基であり：Ｒ，はメチル、エチルまたは約８〜２２個の炭素原子を含むアル キル基でありＳＲ３はメチルまたはエチルでありＳＲ４は約１〜６個の炭素原子 を含むアルキル基であり：Ｘはアニオンであり：そしてＹは次の構造ニ ーｚ、 −ｏｎ、 −０Ｒ９、−ＱＣ（０）Ｒ＠、−ＣＮ。Preferred quaternary ammonium compounds useful in the present invention have the formula: (wherein R1 is -C112-phenyl or an alkyl group containing about 8 to 22 carbon atoms) is a methyl group; R is methyl, ethyl or an alkyl group containing about 8 to 22 carbon atoms; kill group and SR3 is methyl or ethyl and SR4 is about 1 to 6 carbon atoms is an alkyl group containing: X is an anion; and Y is an alkyl group containing the following structure: -z, -on, -0R9, -QC(0)R@, -CN.
Ｒ１２ （式中、Ｒ５、Ｒ６、Ｒ７、Ｒ６、Ｒ９、Ｒ１゜、Ｒ１１、ｌ？＋ｔは約１〜１ ２個の炭素原子を含むアルキル基またはフェニルであり：Ｚはハロゲンでありそ してＱは水素またはカチオンである）を有する基である） を有する。R12 (In the formula, R5, R6, R7, R6, R9, R1°, R11, l?+t are about 1 to 1 is an alkyl group containing 2 carbon atoms or phenyl; Z is likely a halogen; and Q is hydrogen or a cation) has.
本発明に有用なより好ましい有機シリコーン第四級アンモニウム化合物は式： （式中、Ｒ，ＳＲ，およびＲ３は前述のとおりであり、Ｘはアニオンであり、モ してｎは約１〜６（好ましくは３〜６）の整数である） を有する。More preferred organosilicone quaternary ammonium compounds useful in the present invention have the formula: (In the formula, R, SR, and R3 are as described above, X is an anion, and and n is an integer of about 1 to 6 (preferably 3 to 6)) has.
最も好ましい有機シリコーン第四級アンモニウム化合物は、ｎ−オクタデシルジ メチル［３−（１−リメトキシシリル）プロピル］アンモニウムクロライド、ｎ −テトラデシルジメチル［３−（）リメトキシシリル）プロピル）アンモニウム クロライド、ｎ−デシルジメチル〔３−（トリメトキシシリル）プロピル〕アン モニウムクロライド、ｎ−ジドデシルメチル〔３−（トリメトキシシリル）プロ ピル〕アンモニウムクロライドおよびｎ−ドデシルジメチル（３−（１−リメト キンンリル）プロピル〕アンモニウムクロライドである。The most preferred organosilicone quaternary ammonium compound is n-octadecyldi Methyl[3-(1-rimethoxysilyl)propyl]ammonium chloride, n -tetradecyldimethyl[3-()rimethoxysilyl)propyl)ammonium Chloride, n-decyldimethyl[3-(trimethoxysilyl)propyl]an Monium chloride, n-didodecylmethyl [3-(trimethoxysilyl)pro ammonium chloride and n-dodecyldimethyl (3-(1-rimeth) (propyl) ammonium chloride.
その他の活性剤は、例えばセチルピリジニウム化合物のように、窒素をペテロ理 系の一部として含むことができる。好ましいセチルピリジニウム化合物は、２− （３−トリメトキノシリルプロピル）−Ｎ−セチルピリジニウムブロマイドであ る。Other activators, such as cetylpyridinium compounds, can be included as part of the system. Preferred cetylpyridinium compounds are 2- (3-trimethoquinosilylpropyl)-N-cetylpyridinium bromide. Ru.
イソヂオウロニウムハライド化合物も本発明による活性剤として用いるのに適し ている。本発明に用いるのに好ましいイソチオウロニウムハライド化合物は、（ トリメトキノシリルプロピル）イソチオウロニウムクロライドである。Isodiouronium halide compounds are also suitable for use as activators according to the present invention. ing. Preferred isothiouronium halide compounds for use in the present invention are ( trimethoquinosilylpropyl)isothiouronium chloride.
本発明の物品は、（−以上の）活性剤が物品に永久的に結合されるように、活性 剤を物品のポリマー表面に結合している。口腔および身体衛生に用いるのに適し たものとなるには、それら物品は（−以」二の）活性剤を、それが水性媒質中で 実質的に浸出できないように、そのポリマー表面に結合していなければならない 。すなわち、それら物品は、唾液、シャンプー、ひげそり用クリーム、歯みがき およびその他の含水媒質により浸出され得ない永久的抗細菌および／または抗微 生物活性を有するポリマー表面を有する。Articles of the present invention include active agents such that the (- or more) active agent is permanently bound to the article. The agent is attached to the polymer surface of the article. Suitable for use in oral and physical hygiene In order to become Must be bound to the polymer surface so that it cannot be substantially leached out . That is, these items include saliva, shampoo, shaving cream, and toothpaste. and other permanent antibacterial and/or antimicrobial agents that cannot be leached by water-containing media. It has a bioactive polymer surface.
活性剤はいずれの適切な手段、例えば多官能性反応有機物（例えばビス−カルベ ンまたはビス−ナイトレン）を用いた化学的連結、シランカップリング系、プラ ズマ活性化、火炎（ｆｌａｍｅ）活性化、化学的処理およびその池のポリマーグ ラフティング法、などにより物品のポリマー表面に永久的に結合させることがで きる。The activator can be added by any suitable means, such as a polyfunctional reactive organic compound (e.g. bis-carvette). chemical linkage using silane coupling or bis-nitrene), silane coupling system, plastic Zuma activation, flame activation, chemical treatment and polymerization of the pond It can be permanently bonded to the polymer surface of an article by a method such as rafting. Wear.
好ましい結合系は、シランカップリング系である。それによって本発明が限定さ れることはないが、活性剤のアルコキシシリル末端が水の存在下に相当するヒド ロキシ成分に加水分解されるものと思われる。この成分は次に、ポリマー材料の 活性−〇Ｂ、アミドまたはその他の反応部位と反応する。活性剤はいずれの結合 タイプによっでも物品のポリマー表面に結合され得るが、物品のポリマー表面に 剤を共有結合的に結合させるのが好ましい。A preferred coupling system is a silane coupling system. This invention is thereby limited. However, the alkoxysilyl end of the activator will not react with the corresponding hydrogen in the presence of water. It is thought that it is hydrolyzed to a roxy component. This component is then added to the polymer material. Activity - Reacts with 〇B, amide or other reactive sites. The activator binds either type may also be bonded to the polymer surface of the article; Preferably, the agent is attached covalently.
さらに本発明は、化学的または生物学的活性剤のコーティングをポリマー材料よ り成る口腔または身体衛生物品に適用する方法にも関する。この方法は、活性剤 を直接物品の未処理表面に永久的に結合させることより行っていてもよい。さら にその方法は、次の工程、すなわち ｌ 前記物品を水性（ａｑｕｅｏｕｅ−ｂａｓｅｄ）有機または無機酸、水性ア ルカリ水酸化物または有機溶媒より成る群より選択される溶媒と接触させ、そし て ２ 次に前記活性剤を前記物品の表面に結合させる工程より成っていてもよい。Additionally, the present invention provides coatings of chemically or biologically active agents with polymeric materials. It also relates to a method for applying it to an oral or personal hygiene article comprising: This method uses activator may be achieved by permanently bonding directly to the untreated surface of the article. Sara The method consists of the following steps, namely l The article is treated with an aqueous-based organic or inorganic acid, an aqueous-based organic or inorganic acid, contact with a solvent selected from the group consisting of alkali hydroxide or an organic solvent; hand 2. The method may then include the step of bonding the active agent to the surface of the article.
さらに、本発明は、前記方法により処理された物品を包含する。Furthermore, the present invention encompasses articles treated by the method described above.
それによって本発明が限定されることはないが、物品のポリマー表面を溶媒処理 すると活性剤を結合させることができるポリマー表面上の反応部位が露出または 形成されるものと思われる。好ましくは、物品のポリマー表面は、活性剤結合の ための活性部位を含む表面積を約２％以上、より好ましくは約５％以上含む。Although the invention is not limited thereby, the polymer surface of the article may be solvent treated. This exposes or exposes reactive sites on the polymer surface to which the active agent can be attached. It is thought that it will be formed. Preferably, the polymer surface of the article has active agent binding. 2% or more, more preferably about 5% or more of the surface area containing active sites for.
すなわち、物品のポリマー表面の処理に適した溶媒には、活性剤結合のためのポ リマー表面の反応性−０■、アミドまたはその池の反応性部位を露出または形成 するいずれの物質も包含される。適当な溶媒の一部の例には、水性有機および無 機酸、水性アルカリ水酸化物および有機溶媒が包含される。好ましい酸は硫酸お よび酢酸である。好ましいアルカリ水酸化物は水酸化カリウムおよび水酸化ナト リウムである。好ましい有機溶媒にはメタノール、エタノール、イソプロパツー ル、アセトンおよび酢酸エチルが包含される。That is, a solvent suitable for treating the polymer surface of an article will contain a port for activator binding. Reactivity of remer surface -0■, exposing or forming reactive sites of amide or its pond Any substance that does so is included. Some examples of suitable solvents include aqueous organic and non-aqueous solvents. Included are organic acids, aqueous alkaline hydroxides and organic solvents. Preferred acids are sulfuric acid and and acetic acid. Preferred alkali hydroxides are potassium hydroxide and sodium hydroxide. It is Rium. Preferred organic solvents include methanol, ethanol, and isopropyl alcohol. ethyl acetate, acetone and ethyl acetate.
物品のポリマー表面を数分から数時間の範囲の十分な時間溶媒と接触させる。そ れら溶媒は単独で、組合せであるいは連続的に使用することができる。The polymer surface of the article is contacted with the solvent for a sufficient period of time ranging from several minutes to several hours. So These solvents can be used alone, in combination or sequentially.
活性剤を物品のポリマー表面に結合させるに際しては、物品を活性剤と、該活性 剤が表面に結合するのに十分な時間接触させることができる。好ましくは、活性 剤を水またはその他の適切な溶媒の溶液の形とする。その溶液は活性剤をいずれ の濃度で含有してもよいが、好ましくは約１〜約４％（重／容）の活性剤を含有 する。物品を活性剤の溶液と十分な時間（好ましくは約３０分またはそれより長 く）接触させた後、その物品を乾燥し、洗浄しそして高められた温度（好ましく は約５０〜１２５℃）で硬化させることができる。乾燥および硬化条件、例えば 温度、時間、湿度などは、物品の寸法安定性に悪影響を与えないように選択され るべきである。In attaching the active agent to the polymer surface of the article, the article is bonded to the active agent and the polymer surface of the article. Contact can be allowed for a sufficient time for the agent to bind to the surface. Preferably, active The agent is in the form of a solution in water or other suitable solvent. The solution will contain the activator. but preferably about 1% to about 4% (wt/vol) active agent. do. The article is soaked in a solution of the active agent for a sufficient period of time (preferably about 30 minutes or longer). After contact, the article is dried, washed and heated to an elevated temperature (preferably can be cured at a temperature of about 50-125°C). Drying and curing conditions, e.g. Temperature, time, humidity, etc. are selected so as not to adversely affect the dimensional stability of the article. Should.
本発明の物品は様々な微生物種に対して有効であり、そしてそれらはその表面で の微生物増殖を連続的に阻害する。それら物品は、カンジダ・アルビカンス（Ｃ ａｎｄｉｄａ ａｌｂｉｃａｎｓ）、緑膿菌（Ｐｓｅｕｄｏｍｏｎａｓ ａｅｒ ｕｇｉｎｏｓａ）、黄色ブドウ球菌（Ｓｔａｐｈｙｌｏｃｏｃｃｕｓ ａｕｒｅ ｕｓ） 、大腸菌（Ｅｓｃｈｅｒｉｃｈｉａ ｃｏｌｔ） 、ミュータンス／糞 便連鎖球菌（５ｔｒｅｐｔｏｃｏｃｃｕｓ ｗｕｔａｎｓ／ ｆａｅｃａｌｉｓ ）およびクレブシェラ・ニューモー１− 工（Ｋｌｅｂｓｉｅｌｌａ ｐｎｅｕ ｍｏｎｉａｅ）に対する抗微生物活性を示した。The articles of the invention are effective against a variety of microbial species, and they Continuously inhibits microbial growth. Those items are Candida albicans (C andida albicans), Pseudomonas aeruginosa uginosa), Staphylococcus aureus us), Escherichia colt, mutans/feces 5treptococcus wutans/faecalis ) and Klebsiella pneu moniae).
以下実施例を挙げて本発明の実証の一部とする。それら実施例は例示のためであ って、限定するためのものではない。本発明は、ここに記載され例示された態様 およびそれらのすべての均等物を包含する。実施例に用いた部およびパーセント は特に断りのない限りすべて重量基準である。Examples will be given below as part of the demonstration of the present invention. These examples are for illustrative purposes only. It's not meant to be limiting. The invention is based on the aspects described and illustrated herein. and all equivalents thereof. Parts and percentages used in examples All values are by weight unless otherwise specified.
実施例Ｉ それぞれ１．２および４％（重／容）の活性剤を含む様々な処理溶液を本発明の 範囲内で調製した。各溶液は１０ｍＮの濃酢酸および２ｇの界面活性剤（ＤｕＰ ｏｎｔ Ｃｏ、社のＺｏｎｙｌ ＦＳＮ）を脱イオン水、次いで１０．２０また は４０ｇの活性剤と混合して１１の各溶液とすることにより調製した。Example I Various treatment solutions containing 1.2 and 4% (wt/vol) active agent, respectively, were prepared according to the present invention. Prepared within the range. Each solution contained 10 mN concentrated acetic acid and 2 g surfactant (DuP Zonyl (FSN) from Co., Ltd.) was added to deionized water, then 10.20 min. were prepared by mixing with 40 g of active agent to give 11 individual solutions.
その溶液を約３０分間撹拌して活性剤を加水分解した。The solution was stirred for approximately 30 minutes to hydrolyze the active agent.
これらの溶液を下記表■に示す。These solutions are shown in Table 1 below.
試料１ ｎ−オクタデシルジメチル（３−（トリ １％メトキシシリル）プロピ ル〕アンモニウムクロライド 試料２ ２％ 試料３ ４％ 試料４ ０−テトラデンルジメチル（３−（）リ １％メトキシシリル）プロピ ル〕アンモニウムクロライド 試料５ ２％ 試料６ ４％ 試料７ （トリメトキンシリルプロピル）イソチ １％オウロニうムクロライド 試料８ ２％ 試料９ ４％ 試料＋０ ２−（３−トリメトキシシリルプロピル） １％−Ｎ−セチルピリジ ニウムブロマイド 試料１１ ２％ 試料１２ ４％ 実施例■ ナイロン歯ブラシ剛毛繊維を、それら剛毛を各溶液中で約３０分間撹拌すること により試料１〜３の溶液で処理した。剛毛繊維を溶液から取り出し、そして周囲 条件で約３時間乾燥した。次にそれら繊維を脱イオン水で洗浄しそしてオーブン 巾約１２５℃で約１０分間加熱した。それら繊維を室温で冷却しそして試料をそ れぞれ黄色ブドウ球菌、緑膿菌およびカンジダ・アルビカンスの接種物中に入れ た。次にそれら繊維を接種物から取り出した。各接種物からの一試料をただちに Ｌｅｔｈｅｅｎ Ｂｒｏｔｈに入れ、撹拌しそして次にらせん状プレーターを介 してプレートカウント寒天にブロス試料をプレートした。ｌ＋＋１あたりのコロ ニー形成単位数を測定した。各接種物からの他の試料は、１時間または２３時間 放置乾燥してから前述のようにＬｅｔｈｅｅｎ Ｂｒｏｔｈに入れた。活性剤溶 液で処理されない剛毛繊維を対照として用い、処理された剛毛と共に評価した。Sample 1 n-octadecyldimethyl (3-(tri1% methoxysilyl)propyl) Ammonium chloride Sample 2 2% Sample 3 4% Sample 4 0-tetradenyl dimethyl (3-()ri 1% methoxysilyl) propylene Ammonium chloride Sample 5 2% Sample 6 4% Sample 7 (trimethine silylpropyl)isothi 1% ouronium chloride Sample 8 2% Sample 9 4% Sample +0 2-(3-trimethoxysilylpropyl) 1%-N-cetylpyridi nium bromide Sample 11 2% Sample 12 4% Example■ Stir the nylon toothbrush bristle fibers in each solution for approximately 30 minutes. The samples were treated with solutions of samples 1 to 3 according to the following procedure. Remove the bristle fibers from the solution and remove the surrounding It was dried under these conditions for about 3 hours. The fibers are then washed with deionized water and oven It was heated at a width of about 125° C. for about 10 minutes. The fibers were cooled at room temperature and the sample was inoculum of Staphylococcus aureus, Pseudomonas aeruginosa, and Candida albicans, respectively. Ta. The fibers were then removed from the inoculum. one sample from each inoculum immediately Add to Letheen Broth, stir and then pass through a spiral plate. Broth samples were plated on plate count agar. Coro around l++1 The number of knee forming units was measured. Other samples from each inoculum were collected at 1 h or 23 h. After being left to dry, it was placed in Letheen Broth as described above. activator solution Bristle fibers that were not treated with the liquid were used as controls and were evaluated along with the treated bristles.
結果を下記表Ｈに示す。The results are shown in Table H below.
表 ■ 微生物：黄色ブドウ球菌 対照２．７Ｘ１０″２．０ｘｌＯ’ −２２，２３，７ｘｌＯ” ＋３７．０試 料３ ２．４ｘｌＯ’ ２．２ｘｌＯ’ −８，３７，１ｘｌＯ” −９７，Ｏ １ｔ料２ １．８ＸＩＯ’ １．４ＸＩＯ’ −２２，２１，２Ｘ１０’ −９ ３，３試料１ ３．３ｘｌＯ’ ２．６ｘｌＯ’ −２１，２６，５ｘｌＯ’ １０．３微生物−緑膿菌 対照８．０Ｘ１０’ ４．６Ｘ１０’ −４２，５１，９ＸＩＯ” −９９，８ 試料３ ５．５ｘｌＯ’ ３．１ｘｌＧ” −４３，６７，１ｘｌＯ’ −９９ ，９試料２ ３．６ＸｌＯ’ ３．３Ｘ１０’ −８，３５，４Ｘ１０” −９ ９，９試＄４１ ４．９ｘｌＯ’ ４．７ｘｌＯ’ −４，１１，８５ｘｌＯ” −９９，９微生物：カンジダ・アルビカンス 対照３．９ｘｌＯ’ ３．９ｘｌＯ’ ０ ２．１ｘｌＯ” −９４，６試料３ ３．９ｘｌＯ’ ４．１ｘｌＯ’ ＋５．１ ９．８ｘｌＯ’ −９９，８試 料２ ５．９ｘｌＯ’ ６．５ｘｌＯ’ ＋ｌＯ１２ｇ、７ｘｌＯ” −９８， ５試料１ ４．２ｘｌＯ’ ３．２ｘｌＯ’ −２３，８３，１ｘｌＯ’ −９ ２，６＊（コロニー形成単位／厘ｌ） 実施例■ 微生物：緑膿菌 微生物：カンジダ・アルビカンス ＊（コロニー形成単位／菖ｌ） 実施例■ 実施例■の手順に従づて、セルロースアセテートプロピオネートより成る歯ブラ シヘッドを試料４〜６の溶液で処理しそして抗微生物活性を評価した。結果を下 記表■に示す。Table ■ Microorganism: Staphylococcus aureus Control 2.7X10″2.0xlO’-22,23,7xlO”+37.0 test Fee 3 2.4xlO’ 2.2xlO’-8,37,1xlO”-97,O 1t charge 2 1.8XIO' 1.4XIO' -22, 21, 2X10' -9 3,3 Sample 1 3.3xlO' 2.6xlO' -21,26,5xlO' 10.3 Microorganisms - Pseudomonas aeruginosa Control 8.0X10' 4.6X10' -42,51,9XIO" -99,8 Sample 3 5.5xlO’ 3.1xlG”-43,67,1xlO’-99 , 9 sample 2 3.6XlO' 3.3X10'-8, 35, 4X10''-9 9.9 trials $41 4.9xlO' 4.7xlO' -4,11,85xlO" -99,9 microorganism: Candida albicans Control 3.9xlO' 3.9xlO' 0 2.1xlO" -94,6 Sample 3 3.9xlO' 4.1xlO' +5.1 9.8xlO' -99,8 trials Feeding 2 5.9xlO' 6.5xlO' +lO12g, 7xlO" -98, 5 Sample 1 4.2xlO' 3.2xlO' -23,83,1xlO' -9 2,6* (colony forming unit/liter) Example■ Microorganism: Pseudomonas aeruginosa Microorganism: Candida albicans *(Colony forming unit/Iris) Example■ A toothbrush made of cellulose acetate propionate was prepared according to the procedure of Example ■. Sea heads were treated with solutions of samples 4-6 and evaluated for antimicrobial activity. result below Shown in table ■.
表 ■ 微生物：黄色ブドウ球菌 睦−ｕ 尊−哲−１時間本 変化率（％）２３３時間本変化率（％）対照５．１ ｘｌＯ’ ？、５ｘｌＯ’ ＋４７．１ ４．９ｘｌＯ’ −３，９試料６ ４ ．２Ｘ１０’ ８．８Ｘ１０” −７９，１１，５Ｘ！Ｏ” −９９，９試？− ４５５，４ＸＩＯ’ ３．５ＸＩＯ’ −３５，２１，８ＸＩＯ１１−６６，７ 試料４ ３．３ＸＩＯ’ ２．９Ｘ１０’ −１２，１１，１Ｘ１０’ −９９ ，７微生物：緑膿菌 対ｆｆｌ ７．９ＸＩＯ’ ５．９Ｘ１０’ −２５，３１，８Ｘ１０” −９ ９，９試料６ ７．５Ｘ１０’ ６．ｌＸｌ０’ −１８，７６，４Ｘ］Ｏ” −９９，９試料５ ７．９ＸｌＯ’ ６．９ＸＩＯ’ −１２，７１，８ＸＩＯ ” −９９，８試料４ ８．０ｘｌＯ’ ６．６ｘｌＯ’ −１７，５１，６Ｘ ｌｏ’ −９９，９微生物・カンジダ・アルビカンス 対照５．５ＸＩＯ” ５．５Ｘ１０’ ０ １．１Ｘ１０２−９８．０試料６ １．ｌＸ１０’ ６．７Ｘ１０” −３９，１０−１００，０試料５ １．５Ｘ １０’ ９．５ＸＩＯ’ −３６，７７，ｌＸ１０’ −９９，５試料４ ｇ、 ５Ｘ１０３５．７ＸＩＯ’ −３２，９０−１００，０＊（コロニー形成単位／ 麿Ｃ） 実施例■ 実施例■の手順に従って、セルロースアセテートプロピオネートより成る歯ブラ シヘッドを試料７〜９の溶液で処理し、そして抗微生物活性を評価した。結果を 下記表Ｖに示す。Table ■ Microorganism: Staphylococcus aureus Mutsu-u Takashi-Tetsu-1 hour book rate of change (%) 233 hour book rate of change (%) control 5.1 xlO'? , 5xlO' +47.1 4.9xlO' -3,9 Sample 6 4 ．． 2X10’ 8.8X10”-79,11,5X!O”-99,9 test? − 455,4XIO' 3.5XIO'-35,21,8XIO11-66,7 Sample 4 3.3XIO' 2.9X10'-12, 11, 1X10'-99 , 7 microorganisms: Pseudomonas aeruginosa vs ffl 7.9XIO’ 5.9X10’-25,31,8X10”-9 9,9 Sample 6 7.5X10' 6. lXl0'-18,76,4X]O" -99,9 sample 5 7.9XIO' 6.9XIO' -12,71,8XIO ”-99,8 Sample 4 8.0xlO' 6.6xlO'-17,51,6X lo’-99,9 Microorganisms, Candida albicans Control 5.5XIO" 5.5X10' 0 1.1X102-98.0 Sample 6 1. lX10’ 6.7X10”-39,10-100,0 sample 5 1.5X 10' 9.5XIO'-36,77,lX10'-99,5 sample 4 g, 5X1035.7XIO'-32,90-100,0*(Colony forming unit/ Maro C) Example■ A toothbrush made of cellulose acetate propionate according to the procedure of Example ■ Sea heads were treated with solutions of samples 7-9 and antimicrobial activity was evaluated. results It is shown in Table V below.
表 Ｖ 微生物：黄色ブドウ球菌 胚−鼾 当 初市 １時間本 変化率（％）２３３時間本変化率（％）対照５． ７ｘｌＯ’ ４．９ｘｌＯ’ −１３，６１，２ｘｌＯ’ ＋１０２．４試料９ ５．７Ｘ１０’ ４．０Ｘ１０’ −９３，０５，２ＸｌＯ” −９９，１試 料８ ６．６ＸｌＯ’ １．８Ｘ１０’ −９７，３１，９ＸｌＯ’ −９７， １試料７ ６．９Ｘ！０’ ４．８Ｘ１０′′−９９，３９，８ｘｌＯ’ ＋４ １．０微生物：緑膿菌 対照２．ｌＸｌ０６２．２Ｘ１０＠ ＋５．３ ２．３Ｘ１０’ −８８，７試 料９ ２．２Ｘ１０＠２．ｌＸ１０＠−３，２４，４Ｘ１０’ −９９，９試料 ８ ２．２ｘｌＯ＠２．１ｘｌＯ’ −５，５７，３ｘｌＯ’ −９６，６試料 ７ ２．２Ｘ１０＠２．２Ｘ１０＠０ ３．８ＸｌＯ” −９９，８微生物：カ ンジダ・アルビカンス 対Ｍｌ １．４ｘｌＯ’ ６．４ｘｌＯ’ −５４，５２，１Ｘ１０” −８５ ，１試料９ ６．３ＸＩＯ’ ４．６ＸＩＯ’ −９２，７１，ｌＸ１ｏ’ − ９９，８試料８ １．５ｘｌＯ’ ２．０ｘｌＯ” −８６，５１，１ｘｌＯ” −９２，７試料７ ２．４ＸＩＯ’ ７．ｌＸ１Ｏ’ ＋１９５．４ ３．３ Ｘ１０’ ＋３７．９＊（コロニー形成単位／１１） 実施例■ 実施例■の手順に従って、セルロースアセテートプロピオネートより成る歯ブラ シヘッドを試料ｌＯ〜１２の溶液で処理し、そして抗微生物活性を評価した。結 果を下記表■に示す。Table V Microorganism: Staphylococcus aureus Embryo - Snoring Current 1 hour book Change rate (%) 233 hour book Change rate (%) Control 5. 7xlO' 4.9xlO' -13,61,2xlO' +102.4 Sample 9 5.7X10' 4.0X10' -93,05,2XlO" -99,1 trial Fee 8 6.6XlO' 1.8X10'-97,31,9XlO'-97, 1 sample 7 6.9X! 0' 4.8X10''-99,39,8xlO'+4 1.0 Microorganism: Pseudomonas aeruginosa Control 2. lXl062.2X10@+5.3 2.3X10'-88,7 test Fee 9 2.2X10@2. lX10@-3,24,4X10'-99,9 samples 8 2.2xlO@2.1xlO' -5,57,3xlO' -96,6 sample 7 2.2X10@2.2X10@0 3.8XlO"-99,8 Microorganisms: Ka Ndida albicans Vs Ml 1.4xlO' 6.4xlO' -54, 52, 1X10" -85 , 1 sample 9 6.3XIO' 4.6XIO' -92,71,lX1o' - 99,8 Sample 8 1.5xlO' 2.0xlO"-86,51,1xlO" -92,7 Sample 7 2.4XIO' 7. lX1O' +195.4 3.3 X10’+37.9*(Colony forming unit/11) Example■ A toothbrush made of cellulose acetate propionate according to the procedure of Example ■ Sea heads were treated with solutions of samples IO-12 and evaluated for antimicrobial activity. Conclusion The results are shown in Table ■ below.
表 ■ 微生物：黄色ブドウ球菌 延−料 当 初市 １時間本 変化率（％）２３時間本 変化率（％）対照２． ９Ｘ１０１１２．０ＸｌＯ’ −３１，０２，２ＸＩＯ’ −２４，１試料１２ ２．７ｘｌＯ’ １．４ｘｌＯ’ −４８，１１，７ｘｌＯ’ −９３，７試 料１１ ３．ｌＸ１Ｏ’ ２．ｌＸ１０’ −３２，３２，０Ｘ１０’ −９３ ，６試０１０ ３．２Ｘ１０’ ２．４Ｘ１０’ −２５，０４，８Ｘ１０’ −８５，０微生物：緑膿菌 対照６．７ＸＩＯ’ ６．４ＸＩＯ３−４，５２，７Ｘ１０” −９９，６試＄ ４１２ ６．８Ｘ１０’ ６．９Ｘ１０’ ＋１．５ ３．９ＸＩＯ” −９９ ，９試料１１ ６．０Ｘ１０’ ４．５ＸＩＯ’ −２５，０７，ｌＸ１０’ −９９，９試料１０ ８．７Ｘ１０’ ６．７Ｘ１０’ −２３，０２，ｌＸ１ ０’ −９９，８微生物：カンジダ・アルビカンス 対照３．５Ｘ１０’ ３、ｌＸｌ０’ −１１，４１，４ＸＩＯ” −９９，６ 試料１２ ４．４Ｘ１０’ ２．５Ｘ１０’ −４３，２２，９ＸＩＯ” −９ ９，３試料！１ ３．３Ｘ１０’ ３．２Ｘ１０’ −３，０６，０ＸＩＯ” −９８，２試料１０ ４．０Ｘ１０’ ３．４Ｘ１０’ −１５，０９，７Ｘ１ ０” −９９，６＊（コロニー形成単位／■ｌ） 実施例■ セルロースアセテートプロピオネートより成りそして実施例■の手順に従って試 料３の溶液で処理された歯ブラシヘッドを活性剤の浸出性について評価した。こ れら処理された歯ブラシヘッドの一部を数回水洗し、その他のものは未洗浄した 。Table ■ Microorganism: Staphylococcus aureus 1-hour book, rate of change (%), 23-hour book, rate of change (%), control 2. 9X10112.0XIO'-31,02,2XIO'-24,1 sample 12 2.7xlO' 1.4xlO' -48,11,7xlO' -93,7 trials Fee 11 3. lX1O' 2. lX10'-32, 32, 0X10'-93 , 6 trials 010 3.2X10' 2.4X10' -25,04,8X10' -85,0 Microorganism: Pseudomonas aeruginosa Control 6.7XIO’ 6.4XIO3-4,52,7X10”-99,6 trial $ 412 6.8X10' 6.9X10' +1.5 3.9XIO" -99 , 9 Sample 11 6.0X10' 4.5XIO' -25,07, lX10' -99,9 sample 10 8.7X10' 6.7X10' -23,02,lX1 0'-99,8 Microorganism: Candida albicans Control 3.5X10' 3, lXl0'-11,41,4XIO''-99,6 Sample 12 4.4X10' 2.5X10'-43,22,9XIO"-9 9.3 samples! 1 3.3X10' 3.2X10'-3,06,0XIO" -98,2 sample 10 4.0X10' 3.4X10' -15,09,7X1 0”-99,6* (colony forming unit/■l) Example■ cellulose acetate propionate and tested according to the procedure of Example ■. Toothbrush heads treated with Solution 3 were evaluated for active agent leaching. child Some of the treated toothbrush heads were washed several times with water, while others were left unwashed. .
洗浄された、および未洗浄の歯ブラシヘッドをブロモフェノールブルー比色分析 法を用いて浸出性について評価した。ブロモフェノールブルー溶液を０．１１２ ５９のブロモフェノールブルー、４５０ｇの脱イオン水および０．１５ｍ１の１ ０％ Ｎａ２ＣＯ３を混合することにより調製した。それら洗浄された歯ブラシ ヘッド２個を５０諺／の前記ブロモフェノールブルー溶液および２１１７の２％ Ｔｒｉｔｏｎ Ｘ−１００湿潤剤と共に４オンスフレンチスクエアびん（ｆｒｅ ｎｃｈｓｑｕａｒｅ ｂｏｔｔｌｅ）に入れた。未洗浄の歯ブラシヘッド２個も ５０ｍ１の前記ブロモフェノールブルー溶液およびＴｒｉｔｏｎ湿潤剤と共に同 様のびんに入れた。それらびんを約２０分間振盪しそして放置した。１時間、１ ２時間および２４時間後、各びんからの溶液をキュベツトに注ぎ、そして透過率 を５８９ナノメートルにおいて分光光度計で測定した。Bromophenol blue colorimetric analysis of cleaned and uncleaned toothbrush heads The leachability was evaluated using the method. Bromophenol blue solution 0.112 59 bromophenol blue, 450 g deionized water and 0.15 ml 1 Prepared by mixing 0% Na2CO3. those cleaned toothbrushes 2 heads of 50 g/ml of the bromophenol blue solution and 2% of 2117 Triton X-100 Wetting Agent in 4oz French Square Bottle nchsquare bottle). 2 unwashed toothbrush heads Same with 50 ml of the above bromophenol blue solution and Triton wetting agent. I put it in your bottle. The bottles were shaken and allowed to stand for approximately 20 minutes. 1 hour, 1 After 2 and 24 hours, pour the solution from each bottle into a cuvette and measure the transmittance. was measured spectrophotometrically at 589 nanometers.
この手順において、青色色素は歯ブラシヘッド上の結合活性剤と反応してブロモ フェノールブルー溶液の色強度を低下させる。この色強度のロスが歯ブラシヘッ ドの表面に結合した活性剤量の定量的尺度となる。In this step, the blue dye reacts with the binding activator on the toothbrush head to Reduces the color intensity of the phenol blue solution. This loss in color intensity is caused by the loss of color intensity in the toothbrush head. It is a quantitative measure of the amount of active agent bound to the surface of the surface.
評価結果を下記表■に示す。The evaluation results are shown in Table ■ below.
（吸光度単位） 試料採取時間（単位二時間） −試 料 リυ リａ 見υ 煕 Ａ、 洗浄された歯ブラシヘッド ０．３２ ０．３０ ０．３１ ０．３３Ｂ 、 未洗浄の歯ブラシヘッド ０．３１ ０．３０ ０．３３ ０．３３Ｃ１ブ ロモフェノールブルー溶液 ０．５３ ０．５３ ０．５３ ０．５３対照 （試料量変動は±０．０２吸光度単位より小さい）前記結果は洗浄された歯ブラ シヘッドと未洗浄の歯ブラシヘッドの間に有意差がないことを示しているが、こ のことは当初または時間経過後も活性剤の浸出がないことを示唆している。(absorbance unit) Sample collection time (unit: 2 hours) -Sample sample A. Cleaned toothbrush head 0.32 0.30 0.31 0.33B , Uncleaned toothbrush head 0.31 0.30 0.33 0.33C1 b Lomophenol blue solution 0.53 0.53 0.53 0.53 Control (Sample amount variation is less than ±0.02 absorbance units) The above results are for cleaned toothbrushes. This shows that there is no significant difference between toothbrush heads and uncleaned toothbrush heads. This suggests that there is no leaching of the active agent either initially or over time.
、 ＋＋−＋＋＋ ＰＣＴ／１１５９１１０９１１ｇフロントページの続き （５１） Ｉｎｔ、 Ｃ１，５識別記号 庁内整理番号Ｇ Ｏ２Ｃ７１０２８８ ０７−２に ７１０４ ８８０７−２Ｋ Ｉ, +++-+++ PCT/1159110911gContinuation of front page (51) Int, C1,5 identification symbol Internal office reference number G O2C710288 on 07-2 7104 8807-2K I
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| US66287091A | 1991-03-01 | 1991-03-01 | |
| US662,870 | 1991-03-01 | ||
| PCT/US1991/009116 WO1992015198A1 (en) | 1991-03-01 | 1991-12-05 | Oral and personal hygiene articles containing active agents bonded to the surface thereof |
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| JP4505234A Pending JPH06506197A (en) | 1991-03-01 | 1991-12-05 | Oral and body hygiene articles containing an active agent bound to a surface |
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| JP (1) | JPH06506197A (en) |
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| JPH11326849A (en) * | 1998-05-20 | 1999-11-26 | Toray Ind Inc | Production of polymer for ocular lens |
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| FR2695800B1 (en) * | 1992-09-23 | 1996-03-08 | Inst Textile De France | ANTISEPTIC COMPOUND. |
| US5340583A (en) * | 1993-05-06 | 1994-08-23 | Allergan, Inc. | Antimicrobial lenses and lens care systems |
| FR2718330B1 (en) * | 1994-04-07 | 1998-10-02 | Transphyto Sa | Antiseptic items. |
| US6295733B1 (en) | 1994-08-03 | 2001-10-02 | Warner-Lambert Company | Changeable color shaving aid |
| DE19643019C1 (en) | 1996-10-18 | 1998-04-16 | Georg Wiegner | toothbrush |
| US6592814B2 (en) | 1998-10-02 | 2003-07-15 | Johnson & Johnson Vision Care, Inc. | Biomedical devices with antimicrobial coatings |
| JP4392773B2 (en) * | 2000-03-16 | 2010-01-06 | 富士フイルム株式会社 | Photoelectric conversion element and photoelectrochemical cell |
| US8172395B2 (en) | 2002-12-03 | 2012-05-08 | Novartis Ag | Medical devices having antimicrobial coatings thereon |
| DE102007054133A1 (en) * | 2007-11-14 | 2009-05-20 | Mitsubishi Polyester Film Gmbh | Antimicrobially finished, coated, biaxially oriented polyester film |
| KR101306537B1 (en) | 2008-06-04 | 2013-09-09 | 콜게이트-파아므올리브캄파니 | Oral care implement with cavitation system |
| WO2013079957A1 (en) * | 2011-11-30 | 2013-06-06 | Coventry University | Antimicrobial animal product |
| CN110194889B (en) * | 2018-02-27 | 2022-11-15 | 嘉丰工业科技（惠州）有限公司 | Method for preparing modified thermoplastic plastic and product with microorganism adhesion resistance and composition for preparing modified thermoplastic plastic |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2938814A (en) * | 1954-07-19 | 1960-05-31 | Gallowhur Chemical Corp | Method of producing antiseptic articles |
| FR1274388A (en) * | 1957-10-31 | 1961-10-27 | Du Pont | Biologically active graft copolymer, and method of preparation thereof |
| US4035146A (en) * | 1975-10-20 | 1977-07-12 | Schwarz Services International Ltd. | Binding of antimicrobial compounds to a hydroxyl containing substrate with cyanuric chloride |
| US4259103A (en) * | 1979-03-12 | 1981-03-31 | Dow Corning Corporation | Method of reducing the number of microorganisms in a media and a method of preservation |
| US4472327A (en) * | 1983-01-31 | 1984-09-18 | Neefe Charles W | Method of making hydrogel cosmetic contact lenses |
| US4615937A (en) * | 1985-09-05 | 1986-10-07 | The James River Corporation | Antimicrobially active, non-woven web used in a wet wiper |
| DE3720555A1 (en) * | 1987-06-22 | 1989-01-05 | Henkel Kgaa | USE OF INSOLUBLE, POLYFUNCTIONAL QUARTAINE AMMONIUM COMPOUNDS FOR ADSORPTIVE BINDING OF MICROORGANISMS |
| DE3889657T2 (en) * | 1987-11-06 | 1994-11-17 | Ioptex Research Inc | SURFACE-MODIFIED LENS AND METHOD. |
| CA1334506C (en) * | 1988-08-22 | 1995-02-21 | William Curtis White | Method of inhibiting the spread of disease and infection in structures |
| JP2608131B2 (en) * | 1989-03-14 | 1997-05-07 | サンスター株式会社 | toothbrush |
-
1991
- 1991-12-05 BR BR9107297A patent/BR9107297A/en unknown
- 1991-12-05 CA CA002104462A patent/CA2104462A1/en not_active Abandoned
- 1991-12-05 JP JP4505234A patent/JPH06506197A/en active Pending
- 1991-12-05 AU AU12598/92A patent/AU1259892A/en not_active Abandoned
- 1991-12-05 WO PCT/US1991/009116 patent/WO1992015198A1/en not_active Ceased
-
1992
- 1992-02-28 ZA ZA921537A patent/ZA921537B/en unknown
- 1992-02-28 NZ NZ241780A patent/NZ241780A/en unknown
- 1992-02-28 MX MX9200893A patent/MX9200893A/en unknown
- 1992-09-19 EP EP92904862A patent/EP0586384A1/en not_active Withdrawn
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH11326849A (en) * | 1998-05-20 | 1999-11-26 | Toray Ind Inc | Production of polymer for ocular lens |
Also Published As
| Publication number | Publication date |
|---|---|
| MX9200893A (en) | 1992-09-01 |
| CA2104462A1 (en) | 1992-09-02 |
| ZA921537B (en) | 1992-11-25 |
| NZ241780A (en) | 1994-11-25 |
| WO1992015198A1 (en) | 1992-09-17 |
| AU1259892A (en) | 1992-10-06 |
| EP0586384A1 (en) | 1994-03-16 |
| BR9107297A (en) | 1994-06-14 |
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