US20110135846A1 - Antibacterial treatment method for fiber, method for producing antibacterial fiber and antibacterial fiber - Google Patents
Antibacterial treatment method for fiber, method for producing antibacterial fiber and antibacterial fiber Download PDFInfo
- Publication number
- US20110135846A1 US20110135846A1 US12/808,771 US80877108A US2011135846A1 US 20110135846 A1 US20110135846 A1 US 20110135846A1 US 80877108 A US80877108 A US 80877108A US 2011135846 A1 US2011135846 A1 US 2011135846A1
- Authority
- US
- United States
- Prior art keywords
- fiber
- noble metal
- antibacterial
- aqueous solution
- silver
- 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.)
- Abandoned
Links
- 239000000835 fiber Substances 0.000 title claims abstract description 138
- 238000000034 method Methods 0.000 title claims abstract description 58
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 16
- 230000000844 anti-bacterial effect Effects 0.000 title claims description 109
- 229910000510 noble metal Inorganic materials 0.000 claims abstract description 110
- 239000007864 aqueous solution Substances 0.000 claims abstract description 62
- 229910052709 silver Inorganic materials 0.000 claims abstract description 40
- 239000004332 silver Substances 0.000 claims abstract description 40
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 claims abstract description 34
- 150000004696 coordination complex Chemical class 0.000 claims abstract description 26
- 229910052737 gold Inorganic materials 0.000 claims abstract description 9
- 239000010931 gold Substances 0.000 claims abstract description 9
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims abstract description 8
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims abstract description 8
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 claims abstract description 6
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 claims abstract description 4
- 229910052741 iridium Inorganic materials 0.000 claims abstract description 4
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 claims abstract description 4
- 229910052763 palladium Inorganic materials 0.000 claims abstract description 4
- 229910052697 platinum Inorganic materials 0.000 claims abstract description 4
- 229910052702 rhenium Inorganic materials 0.000 claims abstract description 4
- WUAPFZMCVAUBPE-UHFFFAOYSA-N rhenium atom Chemical compound [Re] WUAPFZMCVAUBPE-UHFFFAOYSA-N 0.000 claims abstract description 4
- 229910052703 rhodium Inorganic materials 0.000 claims abstract description 4
- 239000010948 rhodium Substances 0.000 claims abstract description 4
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 claims abstract description 4
- 229910052707 ruthenium Inorganic materials 0.000 claims abstract description 4
- 150000002500 ions Chemical class 0.000 claims description 32
- 239000002082 metal nanoparticle Substances 0.000 claims description 30
- 231100000987 absorbed dose Toxicity 0.000 claims description 15
- FOIXSVOLVBLSDH-UHFFFAOYSA-N Silver ion Chemical compound [Ag+] FOIXSVOLVBLSDH-UHFFFAOYSA-N 0.000 claims description 12
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- 239000000654 additive Substances 0.000 claims description 5
- 230000000996 additive effect Effects 0.000 claims description 5
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- 239000003960 organic solvent Substances 0.000 claims description 3
- 230000005251 gamma ray Effects 0.000 abstract description 3
- 230000000845 anti-microbial effect Effects 0.000 abstract 5
- 239000004599 antimicrobial Substances 0.000 abstract 3
- 238000010894 electron beam technology Methods 0.000 abstract 1
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- 238000005406 washing Methods 0.000 description 39
- 239000003242 anti bacterial agent Substances 0.000 description 19
- -1 silver ions Chemical class 0.000 description 19
- SQGYOTSLMSWVJD-UHFFFAOYSA-N silver(1+) nitrate Chemical compound [Ag+].[O-]N(=O)=O SQGYOTSLMSWVJD-UHFFFAOYSA-N 0.000 description 16
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- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 12
- 238000012360 testing method Methods 0.000 description 12
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- 230000003385 bacteriostatic effect Effects 0.000 description 11
- 239000011230 binding agent Substances 0.000 description 11
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- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- GUTLYIVDDKVIGB-OUBTZVSYSA-N Cobalt-60 Chemical compound [60Co] GUTLYIVDDKVIGB-OUBTZVSYSA-N 0.000 description 10
- 230000005855 radiation Effects 0.000 description 9
- 239000003795 chemical substances by application Substances 0.000 description 8
- 238000006722 reduction reaction Methods 0.000 description 8
- 229910001961 silver nitrate Inorganic materials 0.000 description 8
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- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 3
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- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 description 3
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- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical compound OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 description 2
- 229910002651 NO3 Inorganic materials 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
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- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- 229910017053 inorganic salt Inorganic materials 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
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- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
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- 238000010998 test method Methods 0.000 description 2
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 2
- 229910052723 transition metal Inorganic materials 0.000 description 2
- 150000003623 transition metal compounds Chemical class 0.000 description 2
- 150000003624 transition metals Chemical class 0.000 description 2
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- 241000282836 Camelus dromedarius Species 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 description 1
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
- 239000004696 Poly ether ether ketone Substances 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
- 239000004693 Polybenzimidazole Substances 0.000 description 1
- 239000004695 Polyether sulfone Substances 0.000 description 1
- 239000004697 Polyetherimide Substances 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- 239000004734 Polyphenylene sulfide Substances 0.000 description 1
- 239000004743 Polypropylene Substances 0.000 description 1
- 239000004372 Polyvinyl alcohol Substances 0.000 description 1
- 229920000297 Rayon Polymers 0.000 description 1
- 206010041925 Staphylococcal infections Diseases 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 235000011054 acetic acid Nutrition 0.000 description 1
- YRKCREAYFQTBPV-UHFFFAOYSA-N acetylacetone Natural products CC(=O)CC(C)=O YRKCREAYFQTBPV-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000003463 adsorbent Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000001346 alkyl aryl ethers Chemical class 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 229940088710 antibiotic agent Drugs 0.000 description 1
- 230000001580 bacterial effect Effects 0.000 description 1
- 239000003899 bactericide agent Substances 0.000 description 1
- 230000005540 biological transmission Effects 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 229910000365 copper sulfate Inorganic materials 0.000 description 1
- XTVVROIMIGLXTD-UHFFFAOYSA-N copper(II) nitrate Chemical compound [Cu+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O XTVVROIMIGLXTD-UHFFFAOYSA-N 0.000 description 1
- ARUVKPQLZAKDPS-UHFFFAOYSA-L copper(II) sulfate Chemical compound [Cu+2].[O-][S+2]([O-])([O-])[O-] ARUVKPQLZAKDPS-UHFFFAOYSA-L 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 150000001983 dialkylethers Chemical class 0.000 description 1
- 229910001873 dinitrogen Inorganic materials 0.000 description 1
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- 150000002170 ethers Chemical class 0.000 description 1
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 1
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- 150000002334 glycols Chemical class 0.000 description 1
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- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
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- 239000004310 lactic acid Substances 0.000 description 1
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- 239000007788 liquid Substances 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 150000002736 metal compounds Chemical class 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 150000004706 metal oxides Chemical class 0.000 description 1
- 208000015688 methicillin-resistant staphylococcus aureus infectious disease Diseases 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- LGQLOGILCSXPEA-UHFFFAOYSA-L nickel sulfate Chemical compound [Ni+2].[O-]S([O-])(=O)=O LGQLOGILCSXPEA-UHFFFAOYSA-L 0.000 description 1
- 229910000363 nickel(II) sulfate Inorganic materials 0.000 description 1
- KBJMLQFLOWQJNF-UHFFFAOYSA-N nickel(ii) nitrate Chemical compound [Ni+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O KBJMLQFLOWQJNF-UHFFFAOYSA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 229910000069 nitrogen hydride Inorganic materials 0.000 description 1
- 229910052762 osmium Inorganic materials 0.000 description 1
- SYQBFIAQOQZEGI-UHFFFAOYSA-N osmium atom Chemical compound [Os] SYQBFIAQOQZEGI-UHFFFAOYSA-N 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 238000009980 pad dyeing Methods 0.000 description 1
- PIBWKRNGBLPSSY-UHFFFAOYSA-L palladium(II) chloride Chemical compound Cl[Pd]Cl PIBWKRNGBLPSSY-UHFFFAOYSA-L 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 238000007747 plating Methods 0.000 description 1
- 229920002239 polyacrylonitrile Polymers 0.000 description 1
- 229920001515 polyalkylene glycol Polymers 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229920002480 polybenzimidazole Polymers 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920006393 polyether sulfone Polymers 0.000 description 1
- 229920002530 polyetherether ketone Polymers 0.000 description 1
- 229920001601 polyetherimide Polymers 0.000 description 1
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- 229920005862 polyol Polymers 0.000 description 1
- 150000003077 polyols Chemical class 0.000 description 1
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- 229920001155 polypropylene Polymers 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 238000004445 quantitative analysis Methods 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 239000002964 rayon Substances 0.000 description 1
- 229940100890 silver compound Drugs 0.000 description 1
- 150000003379 silver compounds Chemical class 0.000 description 1
- YPNVIBVEFVRZPJ-UHFFFAOYSA-L silver sulfate Chemical compound [Ag+].[Ag+].[O-]S([O-])(=O)=O YPNVIBVEFVRZPJ-UHFFFAOYSA-L 0.000 description 1
- 229910000367 silver sulfate Inorganic materials 0.000 description 1
- RZTYEUCBTNJJIW-UHFFFAOYSA-K silver;zirconium(4+);phosphate Chemical compound [Zr+4].[Ag+].[O-]P([O-])([O-])=O RZTYEUCBTNJJIW-UHFFFAOYSA-K 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 230000001954 sterilising effect Effects 0.000 description 1
- 238000004659 sterilization and disinfection Methods 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 229920002994 synthetic fiber Polymers 0.000 description 1
- 239000012209 synthetic fiber Substances 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- 229910001428 transition metal ion Inorganic materials 0.000 description 1
- 231100000611 venom Toxicity 0.000 description 1
- 238000009941 weaving Methods 0.000 description 1
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Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
- A61L2/00—Methods or apparatus for disinfecting or sterilising materials or objects other than foodstuffs or contact lenses; Accessories therefor
- A61L2/16—Methods or apparatus for disinfecting or sterilising materials or objects other than foodstuffs or contact lenses; Accessories therefor using chemical substances
- A61L2/23—Solid substances, e.g. granules, powders, blocks, tablets
- A61L2/238—Metals or alloys, e.g. oligodynamic metals
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
- D06M10/00—Physical treatment of fibres, threads, yarns, fabrics, or fibrous goods made from such materials, e.g. ultrasonic, corona discharge, irradiation, electric currents, or magnetic fields; Physical treatment combined with treatment with chemical compounds or elements
- D06M10/008—Treatment with radioactive elements or with neutrons, alpha, beta or gamma rays
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
- D06M11/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with inorganic substances or complexes thereof; Such treatment combined with mechanical treatment, e.g. mercerising
- D06M11/32—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with inorganic substances or complexes thereof; Such treatment combined with mechanical treatment, e.g. mercerising with oxygen, ozone, ozonides, oxides, hydroxides or percompounds; Salts derived from anions with an amphoteric element-oxygen bond
- D06M11/36—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with inorganic substances or complexes thereof; Such treatment combined with mechanical treatment, e.g. mercerising with oxygen, ozone, ozonides, oxides, hydroxides or percompounds; Salts derived from anions with an amphoteric element-oxygen bond with oxides, hydroxides or mixed oxides; with salts derived from anions with an amphoteric element-oxygen bond
- D06M11/38—Oxides or hydroxides of elements of Groups 1 or 11 of the Periodic Table
- D06M11/42—Oxides or hydroxides of copper, silver or gold
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
- D06M11/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with inorganic substances or complexes thereof; Such treatment combined with mechanical treatment, e.g. mercerising
- D06M11/32—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with inorganic substances or complexes thereof; Such treatment combined with mechanical treatment, e.g. mercerising with oxygen, ozone, ozonides, oxides, hydroxides or percompounds; Salts derived from anions with an amphoteric element-oxygen bond
- D06M11/36—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with inorganic substances or complexes thereof; Such treatment combined with mechanical treatment, e.g. mercerising with oxygen, ozone, ozonides, oxides, hydroxides or percompounds; Salts derived from anions with an amphoteric element-oxygen bond with oxides, hydroxides or mixed oxides; with salts derived from anions with an amphoteric element-oxygen bond
- D06M11/49—Oxides or hydroxides of elements of Groups 8, 9,10 or 18 of the Periodic Table; Ferrates; Cobaltates; Nickelates; Ruthenates; Osmates; Rhodates; Iridates; Palladates; Platinates
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
- D06M11/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with inorganic substances or complexes thereof; Such treatment combined with mechanical treatment, e.g. mercerising
- D06M11/83—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with inorganic substances or complexes thereof; Such treatment combined with mechanical treatment, e.g. mercerising with metals; with metal-generating compounds, e.g. metal carbonyls; Reduction of metal compounds on textiles
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
- D06M23/00—Treatment of fibres, threads, yarns, fabrics or fibrous goods made from such materials, characterised by the process
- D06M23/08—Processes in which the treating agent is applied in powder or granular form
Definitions
- the present invention relates to an antibacterial treatment method for fiber, a method for producing antibacterial fiber and antibacterial fiber. More particularly, it relates to an antibacterial treatment method for fiber in which antibacterial metal particulates are firmly adhered to the fiber, a method for producing antibacterial fiber and an antibacterial fiber produced by the production method.
- Harm caused by resistant bacteria such as MRSA derived from frequent use of antibiotics is recently becoming a problem, and new merits have been discovered in inorganic bactericides and antibacterial agents. This is principally because a metal such as silver or a metal oxide such as titanium oxide does not always exhibit a strong bactericidal function but is harmless to the human body without producing resistant bacteria and exhibits continuous antibacterial/antimold function against a wide range of bacteria and mold.
- Antibacterial agents using antibacterial metals are already widely commercially available as products.
- Examples of an antibacterial agent using silver as an antibacterial metal are known as brand names of “Bactekiller” (manufactured by Kanebo Ltd., zeolite-based agent), “Ionpure” (manufactured by Ishizuka Glass Co., Ltd., glass-based agent), “Novaron” (manufactured by Toagosei Co., Ltd., silver-loaded zirconium silver phosphate agent), “Zeomic” (manufactured by Shinagawa Nenryo Co., Ltd., silver-zeolite-based agent), “Zeoplus” (manufactured by Matsumoto Yushi-seiyaku Co., Ltd., silver-zeolite-based agent), “Ceramics AM15” (manufactured by Sumitomo Osaka Cement Co., Ltd., silver-based agent), and “GIN-Tech” (manufactured by Kawasumi Giken Co., Ltd., silver-coated titanium
- the methods for adding silver to these products are roughly divided into a method in which silver ions are adsorbed by an adsorbent such as zeolite, a method in which a silver powder is dispersed in a solvent such as glaze, a method in which a silver compound is reduced electrically or by using an agent (including plating) and the like, and these methods are all on the basis of liquid phase methods.
- Examples of a substance to which an antibacterial agent is added include natural fiber, chemical fiber, ceramics, plastics and metals.
- the sale of textile products occupies about a half of the total sales in fiscal 1996 (according to “Report of Discussion Meeting on New Function Processed Products for Daily Use (Antibacterial Processed Products)” issued by the Ministry of Economy, Trade and Industry in December 1998), and there are increasing demands for antibacterial fiber.
- a “kneading method” in which an antibacterial agent is kneaded in fiber at the stage of spinning the fiber or a “post-processing method” in which an antibacterial agent is added to or coated on the surface of fiber by using a processing liquid containing the antibacterial agent at the stage where the fiber is formed into a product in the shape of, for example, cotton, thread or fabric is generally employed.
- the antibacterial effect is poor considering the added amount, since a portion of the antibacterial agent kneaded inside the fiber does not make a large contribution to the antibacterial effect.
- the additional amount can harmfully affect the fiber, for example, the material of the fiber may be changed in its properties, and in addition, there arises a problem of increase of the cost.
- the post-processing method is advantageous from the viewpoint of the cost and is applicable to a wider range of fibers.
- the kneading method In antibacterial fiber processed by this method, most of the antibacterial agent is adhered to the surface of the fiber, and therefore, the fiber exhibits very high antibacterial performance before washing. When it is repeatedly washed, however, the adhered antibacterial agent is peeled off, and therefore, the antibacterial performance attained after repeated washing is largely degraded with the exception of some organic antibacterial agents (that are chemically bonded to a reaction group of fiber).
- the amount of antibacterial agent to be added is increased or a resin binder is used.
- An inorganic antibacterial agent in particular needs a resin binder.
- the cost is increased, and hence, the advantage in the cost to the kneading method is spoiled as well as there arises a problem that processing characteristics of the post-processing or the texture of a resultant product is degraded.
- Patent Document 1 JP 10-280270A
- Patent Document 2 JP2005-126348A
- an object of the invention is to provide an antibacterial treatment method for fiber in which antibacterial metal particulates are firmly adhered to the surface of fiber easily at low cost without using a resin binder for providing antibacterial fiber with high resistance against washing, a method for producing the antibacterial fiber and an antibacterial fiber obtained by the production method.
- Antibacterial metal particulates are firmly adhered to fiber by a very simple method in which an aqueous solution containing a noble metal ion or a noble metal complex with fiber immersed therein is irradiated with ⁇ rays or electron rays, and the thus obtained fiber exhibits an antibacterial property with high resistance against washing.
- the invention according to claim 1 is an antibacterial treatment method for fiber in which fiber is immersed in an aqueous solution containing a noble metal ion or a noble metal complex, and the aqueous solution is irradiated with ⁇ rays or electron rays.
- the noble metal ion or the noble metal complex contained in the aqueous solution is reduced, through the irradiation with the ⁇ rays or the electron rays, into an atomic noble metal on the surface of the fiber, so as to cause deposition of noble metal particulates of nano-order, namely, noble metal nanoparticles. Since the noble metal nanoparticles are firmly bonded to the fiber, the noble metal nanoparticles with an antibacterial property can be firmly adhered to the fiber simply at low cost without using a resin binder. Hence, antibacterial fiber with high resistance against washing can be provided at low cost.
- metal nanoparticles When metal nanoparticles are synthesized and made to adhere to fiber within an aqueous solution, it is generally regarded that the metal nanoparticles cannot be firmly fixed although they are adsorbed onto the surface of the fiber. Accordingly, as a method for making metal nanoparticles adhere firmly to fiber, it is not general to consider a method of synthesizing metal nanoparticles and making them adhere to fiber within an aqueous solution. In the antibacterial treatment method for fiber of this invention, however, the reduction reaction of the noble metal ion and the deposition reaction of the nanoparticles are very uniformly proceeded in the aqueous solution.
- the deposition of the noble metal nanoparticles is caused in the extreme vicinity of the fiber immersed in the aqueous solution, and therefore, it seems that a state where the noble metal nanoparticles are firmly fixed onto the fiber may be attained.
- the metal nanoparticles in a very unstable state attained immediately after the deposition come into contact with the surface of the fiber, so as to firmly bond to the surface by utilizing the surface energy. Therefore, although the method for synthesizing the metal nanoparticles and making them adhere to the fiber within the aqueous solution is employed, the metal nanoparticles can be firmly adhered to the fiber.
- the noble metal is employed because it is chemically stable and good at antibacterial performance.
- a noble metal is deposited in the form of noble metal nanoparticles and firmly adhered to the fiber having a fine surface so as to attain a large surface area, resulting in increasing possibility of contact with fungi for effectively exhibiting the antibacterial performance.
- the size of the noble metal nanoparticles deposited to be adhered to the fiber is nano-order.
- the size of the noble metal particles can be controlled by adjusting the concentration of the aqueous solution containing the noble metal ion or the noble metal complex or adjusting the absorbed dose of the ⁇ rays or the electron rays.
- the size of the noble metal particles is preferably 1 through 500 nm and more preferably 1 through 100 nm. When the size of the noble metal nanoparticles falls within this range, they are more firmly adhered to the fiber and a large surface area is attained, and therefore, the resultant antibacterial fiber achieve higher antibacterial performance.
- the aqueous solution containing the noble metal ion used in this invention can be easily obtained by dissolving, in water, inorganic salt such as nitrate, halide (chloride in particular), sulfate or carbonate of a noble metal, or hydrophilic organic acid salt such as acetate or citrate of a noble metal.
- inorganic salt such as nitrate, halide (chloride in particular), sulfate or carbonate of a noble metal, or hydrophilic organic acid salt such as acetate or citrate of a noble metal.
- nitrate or chloride is preferred because it is easily dissolved in water and is comparatively inexpensive.
- the aqueous solution containing the noble metal complex can be easily obtained by coordinating an appropriate ligand to the noble metal ion.
- the ligand is not particularly specified as far as it has a lone pair or negative charge and may be selected from various kinds of ligands.
- a monodentate ligand such as a halide ion (F ⁇ , Cl ⁇ , Br ⁇ , I ⁇ or the like), a cyanide ion (CN ⁇ ), ammonia (NH 3 ) or pyridine, a bidentate ligand such as ethylenediamine (H 2 NCH 2 CH 2 NH 2 ), an acetyl acetone ion or the like, or a hexadentate ligand such as an ethylenediaminetetraacetic acid ion may be used.
- a monodentate ligand such as a halide ion (F ⁇ , Cl ⁇ , Br ⁇ , I ⁇ or the like), a cyanide ion (CN ⁇ ), ammonia (NH 3 ) or pyridine
- a bidentate ligand such as ethylenediamine (H 2 NCH 2 CH 2 NH 2 ), an acetyl acetone
- the aqueous solution is most preferred in consideration of inconvenience in adjustment of a processing solution, disposal of the processing solution after the antibacterial treatment and the like and the cost for obtaining the alcohol.
- a transition-metal ion or a transition-metal complex may be mixed in the aqueous solution containing the noble metal ion or the noble metal complex. When it is mixed, the amount of noble metal ion or noble metal complex can be decreased. In other words, in preparation of the aqueous solution, a part of an expensive noble metal compound can be replaced with an inexpensive transition-metal compound. As a result, the cost can be further lowered.
- the transition-metal copper or nickel is preferably used. Examples of the transition-metal compound include copper sulfate, nickel sulfate, copper nitrate and nickel nitrate.
- Conceivable examples of radiation used for depositing the noble metal nanoparticles through irradiation include ⁇ rays or ⁇ rays emitted from an atomic nucleus, ⁇ rays emitted through change in the energy state of an atomic nucleus, proton rays or electron rays generated by an accelerator, and neutron rays generated by utilizing a nuclear reactor, an accelerator or the like.
- Such radiation causes an ionization reaction so as to deposit the noble metal nanoparticles from the solution containing the noble metal ion or the noble metal complex.
- the ⁇ rays or the electron rays are suitably used because they do not activate the fiber or the metal particles while causing the ionization reaction.
- the ⁇ rays and the electron rays are already widely used in sterilization or the like for medical instruments and can be obtained by utilizing existing equipment or techniques.
- the wavelength of the radiation used in the invention is preferably less than 1 nm, more preferably 0.1 nm or less and most preferably 0.01 nm or less. As the wavelength is shorter, fine noble metal nanoparticles with a homogenous size tend to be deposited in shorter time.
- the irradiation of the ⁇ rays or the electron rays is preferably performed with stirring the aqueous solution.
- the temperature condition is not particularly specified.
- the irradiation is generally performed at room temperature (ordinary temperature), but cooling conditions or heating conditions of approximately 0 through 100° C. may be employed.
- the volume of a vessel for the aqueous solution to be irradiated with the ⁇ rays or the electron rays is not particularly specified as far as the aqueous solution accommodated therein can be kept in a homogeneous state by, for example, stirring and the fiber contained therein can be irradiated with the ⁇ rays or the electron rays.
- the volume of the vessel may be appropriately selected in consideration of the type of aqueous solution, the size of a textile product to be treated, the transmission of the ⁇ rays or the electron rays and the like, and is generally selected from a range of approximately 1 mL through 100 L.
- the fiber to which the noble metal particles are adhered in the invention is not particularly specified.
- the fiber include natural fiber such as cotton, wool, silk, linen or camel hair, chemical fiber such as rayon or acetate, synthetic fiber such as polyester, polyamide, polyacrylonitrile, polyethylene, polypropylene, polyether imide, polyphenylene sulfide, polyether sulfone, polyether ether ketone or polybenzimidazole, and fabric manufactured by spinning and weaving one of or a mixture of these fibers.
- the fiber may be short fiber or long fiber, and the fiber may be in the form of cotton or thread, or a product such as a cloth or a knit.
- the noble metal nanoparticles with a fine particle size adhere to the fiber without using a resin binder in this invention, change in the texture can be suppressed. Furthermore, the degree of coloring the fiber can be adjusted by adjusting the amount of metal nanoparticles adhered to the fiber. At this point, the adjustment is easy because there is no need to use a resin binder. Moreover, since the resultant fiber attains high resistance against washing, change in the texture through washing can be suppressed to be small.
- the invention according to claim 2 is the antibacterial treatment method for fiber according to claim 1 in which a noble metal used for making up the noble metal ion or the noble metal complex is at least one noble metal selected from the group consisting of gold, silver, platinum, palladium, ruthenium, rhodium, iridium and rhenium.
- the noble metal contained in the aqueous solution of the noble metal ion or the noble metal complex gold, silver, platinum, palladium, ruthenium, rhodium, iridium or rhenium is preferably used from the viewpoint of high antibacterial performance, oxidation resistance and the like.
- gold, silver, platinum, palladium, ruthenium, rhodium, iridium or rhenium is preferably used from the viewpoint of high antibacterial performance, oxidation resistance and the like.
- silver is most preferred from the viewpoint of the antibacterial performance and the cost.
- the aqueous solution containing the noble metal ion or the noble metal complex can be obtained by dissolving an inorganic salt or a hydrophilic organic acid salt of a noble metal in water.
- an inorganic salt or a hydrophilic organic acid salt of a noble metal in water.
- silver nitrate, chloroauric acid, palladium chloride, silver sulfate or the like is used.
- osmium is excluded from the invention because its oxide is very venomous.
- the invention according to claim 3 is the antibacterial treatment method for fiber according to claim 1 or 2 in which the concentration of the noble metal ion or the noble metal complex in the aqueous solution containing the noble metal ion or the noble metal complex is 1 ⁇ M through 1M.
- the concentration of the aqueous solution containing the noble metal ion or the noble metal complex is preferably 1 ⁇ M through 1 M. More preferably, the concentration is 0.1 through 10 mM.
- the invention according to claim 4 is the antibacterial treatment method for fiber according to claim 1 or 2 in which the noble metal is silver and the concentration of a silver ion or a silver complex in the aqueous solution is 0.005 through 10 mM.
- a silver ion aqueous solution or an aqueous solution containing a silver complex is prepared to have a concentration of 0.005 through 10 mM and the fiber immersed in this aqueous solution is irradiated with the ⁇ rays or the electron rays, a textile product with a higher antibacterial property and higher resistance against washing can be obtained.
- the invention according to claim 5 is the antibacterial treatment method for fiber according to claim 4 in which the noble metal is silver and the concentration of a silver ion or a silver complex in the aqueous solution is 0.01 through 10 mM.
- a silver ion aqueous solution or an aqueous solution containing a silver complex is prepared to have a concentration of 0.01 through 10 mM and the fiber immersed in this aqueous solution is irradiated with the ⁇ rays or the electron rays, a textile product with a much higher antibacterial property and much higher resistance against washing can be obtained.
- the invention according to claim 6 is the antibacterial treatment method for fiber according to any one of claims 1 through 5 in which the ⁇ rays or the electron rays are irradiated under a condition of an absorbed dose of 1 J/kg or more.
- the absorbed dose is preferably 1,000,000 J/kg or less.
- the absorbed dose is more preferably 1 through 1,000,000 J/kg, and most preferably 100 through 100,000 J/kg.
- the ⁇ rays are irradiated preferably under a condition of a dose of 1 Gy or more.
- a cobalt-60 ⁇ radiation source (with energy of ⁇ ray photon of 1.25 MeV) is used as a radiation source, so as to perform the irradiation under conditions of a dose rate of approximately 3 kGy/h and irradiation time of 1 through 18 hours.
- the invention according to claim 7 is the antibacterial treatment method for fiber according to any one of claims 1 through 5 in which the noble metal is silver and the irradiation with the ⁇ rays or the electron rays is performed under a condition of an absorbed dose of 10 through 50000 J/kg.
- the invention according to claim 8 is the antibacterial treatment method for fiber according to any one of claims 1 through 7 in which the aqueous solution containing the noble metal ion or the noble metal complex further comprises at least one additive selected from the group consisting of a water-soluble polymer, a surface active agent and an organic solvent.
- the rate of the reduction reaction of the noble metal ion can be increased, or the size or the like of the noble metal nanoparticles to be deposited can be adjusted.
- the additive include a water-soluble polymer such as polyvinyl alcohol, a surface active agent, alcohols, ethers such as tetrahydrofuran, diethyl ether and diisopropyl ether, polyols such as alkylene glycol, polyalkylene glycol, monoalkyl ether or dialkyl ether of these glycols, and glycerin, carboxylic acids such as formic acid, acetic acid, propionic acid, lactic acid and glycolic acid, and ketones such as acetone and methyl ethyl ketone.
- a water-soluble polymer such as polyvinyl alcohol, a surface active agent, alcohols, ethers such as tetrahydrofuran, diethyl ether and diisopropyl ether, polyols such as alkylene glycol, polyalkylene glycol, monoalkyl ether or dialkyl ether of these glycols, and glycerin
- carboxylic acids
- the invention according to claim 9 is a method for producing antibacterial fiber comprising the antibacterial treatment method for fiber according to any one of claims 1 through 8 .
- the invention according to claim 10 is a method for producing antibacterial fiber in which fiber is immersed in an aqueous solution containing a noble metal ion or a noble metal complex and the aqueous solution is irradiated with ⁇ rays or electron rays.
- noble metal nanoparticles with an antibacterial property can be firmly adhered to the fiber easily at low cost without using a resin binder. Hence, antibacterial fiber with high resistance against washing can be produced at low cost.
- the invention according to claim 11 is an antibacterial fiber produced by the method for producing antibacterial fiber according to claim 9 or 10 .
- the antibacterial fiber is produced by the method for producing antibacterial fiber according to claim 9 or 10 , noble metal nanoparticles with an antibacterial property are firmly adhered to the fiber easily at low cost without using a resin binder. Hence, antibacterial fiber with high resistance against washing can be produced at low cost.
- antibacterial metal nanoparticles can be made to firmly adhere to the surface of fiber easily at low cost without using a resin binder, and hence, antibacterial fiber with high resistance against washing can be provided.
- Example 1 In Example 1 and Comparative Example 1, silver was used as the noble metal for the antibacterial treatment, and the thus attained antibacterial performance was compared with that of a commercially available cloth of antibacterial silver fiber.
- a silver nitrate aqueous solution obtained by adding silver nitrate to 800 mL of water so as to attain a concentration of 0.1 mM was put in a 1-L plastic bottle, and 8 mL of 2-propanol was further added thereto for accelerating the reduction reaction of silver ions.
- 8.6 mg of silver is present in the form of ions.
- a commercially available cloth of antibacterial silver fiber (trade name: Ag fresh processing, manufactured by Nisshin Boseki Co., Ltd.) was used as an antibacterial fiber sample of Comparative Example 1 without subjecting it to any particular treatment such as irradiation with the ⁇ rays.
- Example 1 and Comparative Example 1 Each sample obtained in Example 1 and Comparative Example 1 was divided into two pieces, one of which was directly used as a sample (hereinafter referred to as a “sample with 0 washing”) and the other of which was washed 10 times (hereinafter referred to as a “sample with 10 washing”).
- the washing was performed in accordance with the attached table No. 103 for line dry of JIS L0217 (Care Symbols and Care Labeling for Handling of Textiles), and a JAFET standard detergent (with a neutral property; a nonionic surface active agent) was used as a detergent.
- each of the samples i.e., the sample with 0 washing and the sample with 10 washing
- the antibacterial test was performed by inoculating a prescribed number of fungi (with a viable cell count [A]) in each sample and measuring a viable cell count [C] attained after cultivation of 18 hours, and the antibacterial performance is obtained by comparing the viable cell count [C] with a viable cell count [B] attained after the cultivation of 18 hours in a non-processed sample (i.e., a standard cloth) not subjected to an antibacterial treatment.
- test fungi were inoculated by dropping, onto each sample, a test fungi suspension containing 0.05% of a nonionic surface active agent, and the viable cell count was measured by pour plate method.
- silver ions were used as the noble metal ions, and the relationship between the concentration and the antibacterial property was tested.
- a silver nitrate aqueous solution obtained by adding silver nitrate to 1 L of water so as to attain each concentration shown in Table 2 was put in a vessel, and 1 vol % of 2-propanol was further added thereto for accelerating the reduction reaction of silver ions.
- a commercially available cotton cloth (with a size of 50 cm ⁇ 50 cm) was immersed in each of the resultant aqueous solutions, and the vessel was sealed and irradiated with cobalt-60 ⁇ rays at an absorbed dose of 10 kGy (10000 J/kg) by using the same cobalt-60 ⁇ irradiation equipment as in Example 1. It is noted that the aqueous solution was not stirred during the irradiation. Thereafter, the cotton cloth was taken out of the vessel, washed with water and dried to obtain a sample of each of Examples 2 through 5 having silver nanoparticles adhered to the surface of the fiber.
- silver ions were used as the noble metal ions, and the relationship between the absorbed dose and the antibacterial property was tested.
- a silver nitrate aqueous solution obtained by adding silver nitrate to 1 L of water was put in a vessel, and 1 vol % of 2-propanol was further added thereto for accelerating the reduction reaction of silver ions.
- a commercially available cotton cloth (with a size of 50 cm ⁇ 50 cm) was immersed in the resultant aqueous solution, and the vessel was sealed and irradiated with cobalt-60 ⁇ rays at each absorbed dose shown in Table 3 by using the same cobalt-60 ⁇ irradiation equipment as in Example 1. It is noted that the aqueous solution was not stirred during the irradiation. Thereafter, the cotton cloth was taken out of the vessel, washed with water and dried to obtain a sample of each of Examples 6 through 10 having silver nanoparticles adhered to the surface of the fiber.
- gold was used as the noble metal instead of silver, and the influence of the difference in the kind of noble metal on the antibacterial performance was tested.
- a gold ion aqueous solution with a gold ion concentration of 0.1 mM is prepared from 1 L of water, and the solution was put in a vessel. Thereto, 1 vol % of 2-propanol was further added for accelerating the reduction reaction of gold ions.
- a commercially available cotton cloth (with a size of 50 cm ⁇ 50 cm) was immersed in the resultant aqueous solution, and the vessel was sealed and irradiated with cobalt-60 ⁇ rays at an absorbed dose of 1 kGy (1000 J/kg) by using the same cobalt-60 ⁇ irradiation equipment as in Example 1. It is noted that the aqueous solution was not stirred during the irradiation. Thereafter, the cotton cloth was taken out of the vessel, washed with water and dried to obtain a sample of Example 11 having gold nanoparticles adhered to the surface of the fiber.
- Example 11 The sample of Example 11 thus obtained was subjected to the antibacterial performance test in the same manner as in Example 1. As a result, a bacteriostatic activity value of 1.6 was attained with 0 washing and a bacteriostatic activity value of 0.9 was attained after 10 washing. Thus, it was found that the antibacterial performance was not as high as that attained by using silver (as in Example 8).
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PCT/JP2008/072997 WO2009078442A1 (ja) | 2007-12-19 | 2008-12-17 | 繊維の抗菌処理方法、抗菌性繊維の製造方法および抗菌性繊維 |
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2008
- 2008-12-17 US US12/808,771 patent/US20110135846A1/en not_active Abandoned
- 2008-12-17 JP JP2009546286A patent/JP4854097B2/ja active Active
- 2008-12-17 AT AT08861220T patent/ATE549449T1/de active
- 2008-12-17 EP EP08861220A patent/EP2224054B1/en not_active Not-in-force
- 2008-12-17 CN CN200880120827.9A patent/CN101896663B/zh not_active Expired - Fee Related
- 2008-12-17 KR KR1020107015041A patent/KR101234972B1/ko not_active IP Right Cessation
- 2008-12-17 WO PCT/JP2008/072997 patent/WO2009078442A1/ja active Application Filing
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Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
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US20150114423A1 (en) * | 2010-09-03 | 2015-04-30 | Matsukaze Co., Ltd. | Eyelash extension, and method for making and attaching the same |
US9440001B2 (en) | 2013-03-06 | 2016-09-13 | Specialty Fibres and Materials Limited | Absorbent materials |
US10415179B2 (en) | 2014-12-03 | 2019-09-17 | Paul G. McClory | Method for producing antimicrobial yarns and fabrics by nanoparticle impregnation |
CN114277463A (zh) * | 2022-01-13 | 2022-04-05 | 保定乐家纺织有限公司 | 一种耐污抗菌的复合纺织纤维及其制备方法 |
Also Published As
Publication number | Publication date |
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JPWO2009078442A1 (ja) | 2011-04-28 |
KR101234972B1 (ko) | 2013-02-20 |
ATE549449T1 (de) | 2012-03-15 |
WO2009078442A1 (ja) | 2009-06-25 |
KR20100092047A (ko) | 2010-08-19 |
CN101896663A (zh) | 2010-11-24 |
EP2224054A1 (en) | 2010-09-01 |
CN101896663B (zh) | 2013-07-17 |
JP4854097B2 (ja) | 2012-01-11 |
EP2224054B1 (en) | 2012-03-14 |
EP2224054A4 (en) | 2011-01-26 |
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