CA2835211C - Antimicrobial solid and methods of making and using same - Google Patents
Antimicrobial solid and methods of making and using same Download PDFInfo
- Publication number
- CA2835211C CA2835211C CA2835211A CA2835211A CA2835211C CA 2835211 C CA2835211 C CA 2835211C CA 2835211 A CA2835211 A CA 2835211A CA 2835211 A CA2835211 A CA 2835211A CA 2835211 C CA2835211 C CA 2835211C
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- CA
- Canada
- Prior art keywords
- solid
- antimicrobial
- antimicrobial solid
- bacteria
- solid material
- 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.)
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Links
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- 239000007787 solid Substances 0.000 title claims description 31
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- 239000004094 surface-active agent Substances 0.000 claims abstract description 33
- 229920000867 polyelectrolyte Polymers 0.000 claims description 28
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 25
- 239000000463 material Substances 0.000 claims description 20
- 239000004599 antimicrobial Substances 0.000 claims description 18
- 239000011148 porous material Substances 0.000 claims description 16
- 239000003792 electrolyte Substances 0.000 claims description 10
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- 238000010494 dissociation reaction Methods 0.000 claims description 3
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- 230000003000 nontoxic effect Effects 0.000 claims description 3
- PQUXFUBNSYCQAL-UHFFFAOYSA-N 1-(2,3-difluorophenyl)ethanone Chemical compound CC(=O)C1=CC=CC(F)=C1F PQUXFUBNSYCQAL-UHFFFAOYSA-N 0.000 claims description 2
- 229940044192 2-hydroxyethyl methacrylate Drugs 0.000 claims description 2
- AGBXYHCHUYARJY-UHFFFAOYSA-N 2-phenylethenesulfonic acid Chemical compound OS(=O)(=O)C=CC1=CC=CC=C1 AGBXYHCHUYARJY-UHFFFAOYSA-N 0.000 claims description 2
- NUYSYBDIPXEBHS-UHFFFAOYSA-N 3-(3-ethenylimidazol-1-ium-1-yl)propane-1-sulfonate Chemical compound [O-]S(=O)(=O)CCC[N+]=1C=CN(C=C)C=1 NUYSYBDIPXEBHS-UHFFFAOYSA-N 0.000 claims description 2
- KWIUHFFTVRNATP-UHFFFAOYSA-N Betaine Natural products C[N+](C)(C)CC([O-])=O KWIUHFFTVRNATP-UHFFFAOYSA-N 0.000 claims description 2
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- XIXDXIUWZQJVHJ-UHFFFAOYSA-M trimethyl-[2-(2-methylprop-2-enoyloxy)ethyl]azanium;iodide Chemical compound [I-].CC(=C)C(=O)OCC[N+](C)(C)C XIXDXIUWZQJVHJ-UHFFFAOYSA-M 0.000 claims description 2
- UHVMMEOXYDMDKI-JKYCWFKZSA-L zinc;1-(5-cyanopyridin-2-yl)-3-[(1s,2s)-2-(6-fluoro-2-hydroxy-3-propanoylphenyl)cyclopropyl]urea;diacetate Chemical compound [Zn+2].CC([O-])=O.CC([O-])=O.CCC(=O)C1=CC=C(F)C([C@H]2[C@H](C2)NC(=O)NC=2N=CC(=CC=2)C#N)=C1O UHVMMEOXYDMDKI-JKYCWFKZSA-L 0.000 claims description 2
- FHVDTGUDJYJELY-UHFFFAOYSA-N 6-{[2-carboxy-4,5-dihydroxy-6-(phosphanyloxy)oxan-3-yl]oxy}-4,5-dihydroxy-3-phosphanyloxane-2-carboxylic acid Chemical compound O1C(C(O)=O)C(P)C(O)C(O)C1OC1C(C(O)=O)OC(OP)C(O)C1O FHVDTGUDJYJELY-UHFFFAOYSA-N 0.000 claims 1
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- WKALLSVICJPZTM-UHFFFAOYSA-N 3-[decyl(dimethyl)azaniumyl]propane-1-sulfonate Chemical compound CCCCCCCCCC[N+](C)(C)CCCS([O-])(=O)=O WKALLSVICJPZTM-UHFFFAOYSA-N 0.000 description 1
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- LZZYPRNAOMGNLH-UHFFFAOYSA-M Cetrimonium bromide Chemical compound [Br-].CCCCCCCCCCCCCCCC[N+](C)(C)C LZZYPRNAOMGNLH-UHFFFAOYSA-M 0.000 description 1
- 239000005749 Copper compound Substances 0.000 description 1
- QRLVDLBMBULFAL-UHFFFAOYSA-N Digitonin Natural products CC1CCC2(OC1)OC3C(O)C4C5CCC6CC(OC7OC(CO)C(OC8OC(CO)C(O)C(OC9OCC(O)C(O)C9OC%10OC(CO)C(O)C(OC%11OC(CO)C(O)C(O)C%11O)C%10O)C8O)C(O)C7O)C(O)CC6(C)C5CCC4(C)C3C2C QRLVDLBMBULFAL-UHFFFAOYSA-N 0.000 description 1
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- NLEBIOOXCVAHBD-QKMCSOCLSA-N dodecyl beta-D-maltoside Chemical compound O[C@@H]1[C@@H](O)[C@H](OCCCCCCCCCCCC)O[C@H](CO)[C@H]1O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 NLEBIOOXCVAHBD-QKMCSOCLSA-N 0.000 description 1
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- YFVGRULMIQXYNE-UHFFFAOYSA-M lithium;dodecyl sulfate Chemical compound [Li+].CCCCCCCCCCCCOS([O-])(=O)=O YFVGRULMIQXYNE-UHFFFAOYSA-M 0.000 description 1
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- UMWKZHPREXJQGR-UHFFFAOYSA-N n-methyl-n-(2,3,4,5,6-pentahydroxyhexyl)decanamide Chemical compound CCCCCCCCCC(=O)N(C)CC(O)C(O)C(O)C(O)CO UMWKZHPREXJQGR-UHFFFAOYSA-N 0.000 description 1
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- HEGSGKPQLMEBJL-RKQHYHRCSA-N octyl beta-D-glucopyranoside Chemical compound CCCCCCCCO[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O HEGSGKPQLMEBJL-RKQHYHRCSA-N 0.000 description 1
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- XLYOFNOQVPJJNP-UHFFFAOYSA-O oxonium Chemical compound [OH3+] XLYOFNOQVPJJNP-UHFFFAOYSA-O 0.000 description 1
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- 230000036961 partial effect Effects 0.000 description 1
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- 235000021317 phosphate Nutrition 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 238000009428 plumbing Methods 0.000 description 1
- 239000000256 polyoxyethylene sorbitan monolaurate Substances 0.000 description 1
- 235000010486 polyoxyethylene sorbitan monolaurate Nutrition 0.000 description 1
- 235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 description 1
- 235000013824 polyphenols Nutrition 0.000 description 1
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- 229920000053 polysorbate 80 Polymers 0.000 description 1
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- 108700004121 sarkosyl Proteins 0.000 description 1
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- NRHMKIHPTBHXPF-TUJRSCDTSA-M sodium cholate Chemical compound [Na+].C([C@H]1C[C@H]2O)[C@H](O)CC[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CC[C@H]([C@@H](CCC([O-])=O)C)[C@@]2(C)[C@@H](O)C1 NRHMKIHPTBHXPF-TUJRSCDTSA-M 0.000 description 1
- FHHPUSMSKHSNKW-SMOYURAASA-M sodium deoxycholate Chemical compound [Na+].C([C@H]1CC2)[C@H](O)CC[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CC[C@H]([C@@H](CCC([O-])=O)C)[C@@]2(C)[C@@H](O)C1 FHHPUSMSKHSNKW-SMOYURAASA-M 0.000 description 1
- VMSNAUAEKXEYGP-YEUHZSMFSA-M sodium glycodeoxycholate Chemical compound [Na+].C([C@H]1CC2)[C@H](O)CC[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CC[C@H]([C@@H](CCC(=O)NCC([O-])=O)C)[C@@]2(C)[C@@H](O)C1 VMSNAUAEKXEYGP-YEUHZSMFSA-M 0.000 description 1
- KSAVQLQVUXSOCR-UHFFFAOYSA-M sodium lauroyl sarcosinate Chemical compound [Na+].CCCCCCCCCCCC(=O)N(C)CC([O-])=O KSAVQLQVUXSOCR-UHFFFAOYSA-M 0.000 description 1
- WDFRNBJHDMUMBL-OICFXQLMSA-M sodium;(4r)-4-[(3r,5s,7r,8r,9s,10s,13r,14s,17r)-3,7-dihydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1h-cyclopenta[a]phenanthren-17-yl]pentanoate Chemical compound [Na+].C([C@H]1C[C@H]2O)[C@H](O)CC[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CC[C@H]([C@@H](CCC([O-])=O)C)[C@@]2(C)CC1 WDFRNBJHDMUMBL-OICFXQLMSA-M 0.000 description 1
- HRQDCDQDOPSGBR-UHFFFAOYSA-M sodium;octane-1-sulfonate Chemical compound [Na+].CCCCCCCCS([O-])(=O)=O HRQDCDQDOPSGBR-UHFFFAOYSA-M 0.000 description 1
- 239000012453 solvate Substances 0.000 description 1
- 238000004659 sterilization and disinfection Methods 0.000 description 1
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- 239000000758 substrate Substances 0.000 description 1
- 125000000542 sulfonic acid group Chemical group 0.000 description 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
- 239000002344 surface layer Substances 0.000 description 1
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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
- A01N25/08—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 containing solids as carriers or diluents
- A01N25/10—Macromolecular compounds
-
- 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
- A01N25/08—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 containing solids as carriers or diluents
Landscapes
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Health & Medical Sciences (AREA)
- Toxicology (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Agronomy & Crop Science (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Apparatus For Disinfection Or Sterilisation (AREA)
- Paints Or Removers (AREA)
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| US201161484558P | 2011-05-10 | 2011-05-10 | |
| US61/484,558 | 2011-05-10 | ||
| PCT/US2012/037320 WO2012154953A2 (en) | 2011-05-10 | 2012-05-10 | Antimicrobial solid and methods of making and using same |
Publications (2)
| Publication Number | Publication Date |
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| CA2835211A1 CA2835211A1 (en) | 2012-11-15 |
| CA2835211C true CA2835211C (en) | 2019-09-24 |
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| EP (2) | EP2706845B1 (OSRAM) |
| JP (1) | JP6463629B2 (OSRAM) |
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| BR (1) | BR112013028673B1 (OSRAM) |
| CA (1) | CA2835211C (OSRAM) |
| WO (1) | WO2012154953A2 (OSRAM) |
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| EP2346324A4 (en) | 2008-10-06 | 2012-10-10 | Microbial Defense Systems Llc | ANTIMICROBIAL COMPOSITION AND METHODS OF MAKING AND USING |
| CA2835211C (en) | 2011-05-10 | 2019-09-24 | Next Science, Llc | Antimicrobial solid and methods of making and using same |
| US9872843B2 (en) * | 2011-10-08 | 2018-01-23 | Next Science, Llc | Antimicrobial compositions and methods employing same |
| EP2991483A4 (en) | 2013-05-02 | 2016-11-30 | Next Science Llc | ANTIMICROBIAL COMPOSITION WITH HIGH OSMOLARITY WITH ONE OR MORE ORGANIC SOLVENTS |
| EP3337325A4 (en) | 2015-07-17 | 2019-02-13 | Next Science IP Holdings Pty Ltd | ANTIMICROBIAL COMPOSITION WITH EFFICACY TO ENDOSPORES |
| US11118143B2 (en) | 2015-08-07 | 2021-09-14 | Next Science IP Holdings Pty Ltd | Antimicrobial composition having efficacy against endospores |
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| CN113197200B (zh) * | 2021-04-30 | 2022-04-08 | 中国农业科学院植物保护研究所 | 农药分子噁霉灵作为胶凝剂的凝胶载药体系的制备方法及用途 |
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- 2012-05-10 EP EP18203838.0A patent/EP3456200B1/en active Active
- 2012-05-10 BR BR112013028673-3A patent/BR112013028673B1/pt not_active IP Right Cessation
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2014
- 2014-09-14 US US14/485,748 patent/US10045527B2/en active Active
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2018
- 2018-08-11 US US16/101,436 patent/US10609923B2/en active Active
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| WO2012154953A3 (en) | 2013-01-17 |
| US10653133B2 (en) | 2020-05-19 |
| BR112013028673A2 (pt) | 2016-08-09 |
| CA2835211A1 (en) | 2012-11-15 |
| EP3456200A1 (en) | 2019-03-20 |
| AU2012253476A1 (en) | 2013-11-21 |
| US20150004203A1 (en) | 2015-01-01 |
| US10045527B2 (en) | 2018-08-14 |
| EP3456200B1 (en) | 2023-05-03 |
| BR112013028673B1 (pt) | 2020-06-16 |
| WO2012154953A2 (en) | 2012-11-15 |
| EP2706845A2 (en) | 2014-03-19 |
| EP2706845B1 (en) | 2021-06-23 |
| EP2706845A4 (en) | 2014-10-29 |
| US11172677B2 (en) | 2021-11-16 |
| US10609923B2 (en) | 2020-04-07 |
| US20120288469A1 (en) | 2012-11-15 |
| AU2012253476B2 (en) | 2015-09-24 |
| US20200260723A1 (en) | 2020-08-20 |
| JP2014517834A (ja) | 2014-07-24 |
| JP6463629B2 (ja) | 2019-02-06 |
| US20180343853A1 (en) | 2018-12-06 |
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