WO2006085975A2 - Organic biocidal decontamination compositions - Google Patents

Organic biocidal decontamination compositions Download PDF

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Publication number
WO2006085975A2
WO2006085975A2 PCT/US2005/023823 US2005023823W WO2006085975A2 WO 2006085975 A2 WO2006085975 A2 WO 2006085975A2 US 2005023823 W US2005023823 W US 2005023823W WO 2006085975 A2 WO2006085975 A2 WO 2006085975A2
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WO
WIPO (PCT)
Prior art keywords
composition
carrier
weight
biocide
silver
Prior art date
Application number
PCT/US2005/023823
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English (en)
French (fr)
Other versions
WO2006085975A3 (en
Inventor
Kyle Knappenberger
Lisa Martin
Paul S. Malchesky
Original Assignee
Nanoscale Materials, Inc.
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Nanoscale Materials, Inc. filed Critical Nanoscale Materials, Inc.
Priority to EP05857504A priority Critical patent/EP1768680A2/en
Priority to JP2007519540A priority patent/JP2008505123A/ja
Publication of WO2006085975A2 publication Critical patent/WO2006085975A2/en
Publication of WO2006085975A3 publication Critical patent/WO2006085975A3/en

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Classifications

    • AHUMAN NECESSITIES
    • A01AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01NPRESERVATION 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
    • A01N43/00Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/48Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
    • A01N43/541,3-Diazines; Hydrogenated 1,3-diazines
    • AHUMAN NECESSITIES
    • A01AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01NPRESERVATION 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
    • A01N31/00Biocides, pest repellants or attractants, or plant growth regulators containing organic oxygen or sulfur compounds
    • A01N31/04Oxygen or sulfur attached to an aliphatic side-chain of a carbocyclic ring system
    • AHUMAN NECESSITIES
    • A01AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01NPRESERVATION 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
    • A01N37/00Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
    • A01N37/16Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing the group; Thio analogues thereof
    • AHUMAN NECESSITIES
    • A01AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01NPRESERVATION 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
    • A01N59/00Biocides, pest repellants or attractants, or plant growth regulators containing elements or inorganic compounds
    • AHUMAN NECESSITIES
    • A01AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01NPRESERVATION 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
    • A01N59/00Biocides, pest repellants or attractants, or plant growth regulators containing elements or inorganic compounds
    • A01N59/16Heavy metals; Compounds thereof
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00Medicinal preparations containing organic active ingredients
    • A61K31/13Amines
    • A61K31/14Quaternary ammonium compounds, e.g. edrophonium, choline
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K33/00Medicinal preparations containing inorganic active ingredients
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K33/00Medicinal preparations containing inorganic active ingredients
    • A61K33/04Sulfur, selenium or tellurium; Compounds thereof
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K33/00Medicinal preparations containing inorganic active ingredients
    • A61K33/22Boron compounds
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K33/00Medicinal preparations containing inorganic active ingredients
    • A61K33/40Peroxides
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K45/00Medicinal preparations containing active ingredients not provided for in groups A61K31/00 - A61K41/00
    • A61K45/06Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca

Definitions

  • the present invention is broadly concerned with decontamination compositions and methods useful for the neutralization or destruction of biological agents such as biological weapon (BW) agents and environmentally-derived undesirable biological agents (e.g., spores, bacteria, viruses, fungi, and molds). More particularly, the invention is concerned with such compositions and methods which may be in liquid form as sprayable or foamable products for example, and which include a biocide fraction together with a carrier; the compositions preferably are organic in character and have only minimal quantities of water.
  • biological weapon BW
  • environmentally-derived undesirable biological agents e.g., spores, bacteria, viruses, fungi, and molds.
  • Patent No. 5 ,914,436 describes methods for the destruction of unwanted compounds such as chlorocarbons, chlorofluorocarbons and PCBs, making use of metal oxide composites as adsorbents.
  • Patent No. 6,057,488 describes the use of metal oxide nanoparticles for the destructive adsorption of biological and chemical contaminants, including biological and chemical warfare agents and environmental contaminants.
  • Sandia National Laboratories has recently developed a foam decontamination product referred to as "Sandia Decon Formulation” and includes solubilizing compounds such as cationic surfactants and hydrotropes together with reactive compound(s) such as nucleophilic and oxidizing compounds.
  • the Sandia foam products are available from EnviroFoam Technologies of Huntsville, Alabama, and Modec, Inc. of Denver, Colorado, and are described in PCT Publication WO 02/02192 published January 10, 2002 and incorporated by reference herein.
  • the present invention is concerned with decontamination compositions having a relatively low water content (less than about 10% by weight water, more preferably less than about 2% by weight and still more preferably less than about 0.1% by weight water) and including a biocide fraction together with a carrier.
  • the carrier includes a component different than any component of the biocide fraction and is broadly selected from the group consisting of straight or branched chain substituted or unsubstituted halogen C3-C15 hydrocarbons, Cl -C 12 straight or branched chain alkyl alcohols, and mixtures thereof.
  • the compositions of the invention are useful for the neutralization or destruction of biological agents including biological warfare agents and environmental contaminants.
  • the products of the invention may be in the form of liquid sprayable products or can be used in the form of fogs, mists, vapors, gels, pastes, or wipes.
  • a "wipe” is a sheet of woven or unwoven material, formed of natural or synthetic fibers, onto which a quantity of the inventive composition is absorbed.
  • the biocide fraction is preferably selected from the group consisting of biocidally effective organic peroxides, oxides, aldehydes, phenols, napthas and acids, quaternary ammonium compounds, transition metals and salts thereof, the halogens, compounds containing a halogen, N, S or B atom, ozone and mixtures thereof.
  • preferred biocides are selected from the group consisting of organic peroxides, formaldehyde, glutaraldehyde, peroxyacetic acid, ozone, the alkali metal chlorites and hypochlorites (e.g., sodium or potassium chlorite and hypochlorite), chlorine, chlorine dioxide, alkylene oxides (e.g., ethylene and propylene oxides), 2-amino-2-methyl-l-propanol, cetyltrimethylammonium bromide, cetylpyridinium chloride, 2,4,4-trichloro-2-hydroxydiphenylether, l-(4-chlorophenyl)-3-(3,4- dichlorophenyl) urea, zinc salts, pentachlorophenol, copper naphthenate, tributyltin oxide, dichlorophen, p-nitrophenol, p-chloro-m-xylenol, beta-naphthol, 2,3,5,6-te
  • Known antimicrobial compounds can be used in the compositions such as hydrogen peroxide 0.8% in combination with peroxyacetic acid 0.06%; sodium chlorite 1.52%; amylphenol 7.6%; ethylene oxide 8.5%; sodium hypochlorite 12.5%; sodium chlorite 72.8%; hydrogen peroxide 6.9% in combination with peroxyacetic acid 4.4% and octanoic acid 3.3%; hydrogen peroxide 22% in combination with 4.5% peroxyacetic acid 4.5%; peroxyacetic acid 35%; and hydrogen peroxide 31%.
  • the biocide fraction is present in the overall composition at a level of from about 0.01- 10% by weight, more preferably from about 1-5% by weight.
  • the most preferred class of carriers are the substituted fluorinated C3-C15 hydrocarbons, and especially alkoxy-substituted hydrocarbons of this class.
  • exemplary carriers are the HFE solvents such as HFE 7100 (methoxynonafluorobutane), 71DA (HFE7100, trans- 1,2- dichloroethylene and ethanol azeotrope), 7 HPA (HFE7100 and ethanol azeotrope), and 7500 (2- trifluoromethyl-3-ethoxydodecofluorohexane), and mixtures thereof.
  • HFE solvents such as HFE 7100 (methoxynonafluorobutane), 71DA (HFE7100, trans- 1,2- dichloroethylene and ethanol azeotrope), 7 HPA (HFE7100 and ethanol azeotrope), and 7500 (2- trifluoromethyl-3-ethoxydodecofluorohexane), and mixtures thereof.
  • a carrier in the form of a mixture of one or more of the fluorinated hydrocarbons described above together with a C 1 - C6 alkyl alcohol such as ethanol.
  • the alcohol should be present at a level up to about 20% by weight and more preferably less than about 5% by weight.
  • Particularly effective sporicides have been prepared using this type of combined fluorinated hydrocarbon/alkyl alcohol carrier with a silver salt as a biocide, e.g., silver nitrate or with hydrogen peroxide, peroxyacetic acid, or hypochlorite.
  • compositions of the invention may also be advisable to include a surfactant in the compositions of the invention to increase the dispersibility of the biocide in the carrier.
  • a surfactant in the compositions of the invention to increase the dispersibility of the biocide in the carrier.
  • a large number of surfactants would be suitable, depending upon desired end uses.
  • cationic, anionic, nonionic or amphoteric surfactants may be used in the compositions.
  • the surfactant when used is normally present at a level of from about 0.1 to 20% by weight of the composition, and more preferably less than about 3% by weight.
  • compositions of the invention may be used for decontaminating an area by distributing the compositions into or adjacent the area. That is, the compositions may be used to decontaminate surfaces such as buildings, walls, or other structures, equipment, furniture, and the soil. Additionally, the compositions can be used for decontaminating contaminated ambient atmosphere by distribution in the form of a fog, mist, vapor or spray, or may be incorporated into gels, pastes, and wipes for decontaminating inanimate or animate objects. A variety of application equipment and techniques can be used in this context, for example equipment for pressurized broadcast applications, or for layering onto surfaces. Depending upon the biocide fraction selected, the compositions may be used for the neutralization or destruction of bacterial spores, vegetative bacteria, viruses, fungi and molds, or any other bacteriological or infectious agent.
  • the area or surface to be decontaminated may be incompatible with the biocide compositions used with the present invention.
  • the carrier composition (without the biocide) may be used to collect and remove the biological agent from the area.
  • the biological agent may then be deactivated by adding the biocide to the carrier containing the biological agent.
  • a series of formulations were evaluated by placement in a glass screening vial.
  • 5 ml of distilled water was added to a separate screening vial.
  • a concentration of either 10 5 CFU/100 ⁇ l or 1.5 x 10 7 CFU/100 ⁇ l of bacterial spores ⁇ Bacillus subtilus) was added to each vial for a concentration of approximately 3 x 10 6 CFU/ml (for the higher challenges).
  • the vials were capped and vortexed for 30 seconds, whereupon they were allowed to sit undisturbed for 74.5 minutes. After the 74.5 minute sit time had elapsed, each vial was again vortexed for 30 seconds.
  • the suspensions were then filtered by placing a membrane filter on a filtering apparatus and adding 50 ml of distilled water to each filter followed by 100 ⁇ l of solution from a screening vial (appropriate dilutions were carried out on the higher concentration challenges) . After the initial filtering, the filters were washed twice with 25 ml of distilled water. Once the liquid was removed, the filters were taken from the apparatus and placed on a nutrient agar plate and incubated 24 hours at 37 0 C. All experiments were sampled in triplicate at room temperature.
  • HFE solvents formulations 1 and 2
  • silver compounds Formulations 3-7
  • dichumyl peroxide Formulations 8-10
  • sodium hypochlorite/bleach Formulations 11-18
  • peroxyacetic acid Formulations 19-24
  • hydrogen peroxide Formulamulations 25-26.
  • Different carriers were used in respective formulations, as set forth in Table 1.
  • Example 2 In this test, the surface decontamination properties of certain compositions in accordance with the invention were tested. Initially, 1 inch square glass sides were inoculated with 100 ⁇ l of an approximately 1.5 x 10 8 CFU/ml solution of Bacillus subtilus spores in 40% ethanol, and allowed to dry for 2-3 hours. The biocidal formulations being evaluated were prepared minutes before use. The glass slides were each placed in a small plastic jar with a volume of about 30 ml. Each test slide receiving biocide was sprayed with 2.27 ml of the test formulation. Another slide served as a dry control (no formulation added) while a third slide was sprayed with 2.27 ml distilled water (wet control).
  • AU slides were left in the jars, uncapped for 75 minutes. Once the 75 minutes elapsed, 20 ml of distilled water was added to each jar whereupon the jars were capped, vortexed for 30 seconds, and left undisturbed for 10 minutes to elute the spores. Once the 10 minutes had elapsed, the jars were vortexed for a few seconds and 100 ⁇ l of solution removed and diluted in 1.9 ml of distilled water. The diluted mixtures were then filtered by placing a membrane filter on the filtering apparatus and adding 50 ml of distilled water to each filter followed by 100 ⁇ l of test solution (25 ⁇ l for the controls).
  • the filters were washed twice with 25 ml of distilled water. After removing all liquid, the filters were taken from the apparatus and placed on a nutrient agar plate and incubated 24 hours at 37 0 C. All experiments were conducted in triplicate at room temperature.
  • test solutions included HFE-7100 and HFE-7500 solvent supplemented with 13% by weight ethanol and with 0.22% by weight silver nitrate added. These test formulations were prepared by initially dispersing the silver nitrate in ethanol, followed by addition thereof to the HFE solvent. These steps were carried at room temperature with appropriate mixing of the formulation prior to adding it to the cultures. The following table sets forth the results of this test.
  • the spore suspension of the stock specimen was grown on potato dextrose agar (PDA) for approximately one month for the mycelial cultures and on corn meal agar (CMA) for five weeks for the spore cultures, all at room temperature in the dark side of a fume hood.
  • PDA potato dextrose agar
  • CMA corn meal agar
  • the petri dishes were sealed with parafilm.
  • the plates were used to test the effectiveness of the formulations against the mycelial form (PDA) and spore form (CMA). Five ml of each of the formulations were sprayed to evenly cover the entire surface area of the plate in a Biosafety cabinet with vertical flow.
  • PDA mycelial form
  • CMA spore form
  • the formulation was in contact with the specimen for 75 minutes. After the contact time, each treated and control plate had six plugs removed therefrom and transferred to a new PDA plate. The plates were incubated for approximately 1 -2 weeks at room temperature in the dark in a fume hood. The regrowth for each plug was visually determined as emerging mycelium. Untreated controls were used as a gauge of when sufficient growth was achieved. All experiments were sampled in triplicate.
  • Each PDA plate was qualitatively evaluated for the number of plugs that resulted in regrowth on a scale of 0 to 6, with "0" indicating a low level of activity, and "6" indicating a high level of activity.
  • the plates were scored as a number of positive regrowths, the number of kills, and the number of inhibitions.
  • the positive control and distilled water were used to determine the baseline regrowth and for comparison to determine growth inhibition.
  • the sterile distilled water, carrier solvent, and the potato flour treatments were evaluated to determine if the conditions of treatment resulted in reduced growth. All resulted in full regrowth.
  • the results are given in Table 3.
  • the CMA plates were treated in the same manner as the PDA plates for the Stachybotrys mycelia test.
  • the formulation was sprayed evenly on the agar plate in a Biosafety cabinet with vertical flow (Class II) and sealed with parafilm for 75 minutes. Once the 75 minutes had elapsed, 10 ml of sterile deionized water with 0.1% Tween 80 was added to the CMA plate and gently stirred. 150 ⁇ l of the recovered sterile distilled water containing sporces was plated onto PDA in triplicate. The plates were incubated 1-2 weeks at room temperature in a fume hood and the number of established colonies counted. The results are given in Table 4.

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  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Epidemiology (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Animal Behavior & Ethology (AREA)
  • Medicinal Chemistry (AREA)
  • Public Health (AREA)
  • Inorganic Chemistry (AREA)
  • Agronomy & Crop Science (AREA)
  • Pest Control & Pesticides (AREA)
  • Plant Pathology (AREA)
  • Engineering & Computer Science (AREA)
  • Dentistry (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
PCT/US2005/023823 2004-07-02 2005-06-30 Organic biocidal decontamination compositions WO2006085975A2 (en)

Priority Applications (2)

Application Number Priority Date Filing Date Title
EP05857504A EP1768680A2 (en) 2004-07-02 2005-06-30 Organic biocidal decontamination compositions
JP2007519540A JP2008505123A (ja) 2004-07-02 2005-06-30 有機殺生性除染組成物

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US88422804A 2004-07-02 2004-07-02
US10/884,228 2004-07-02

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WO2006085975A2 true WO2006085975A2 (en) 2006-08-17
WO2006085975A3 WO2006085975A3 (en) 2007-06-21

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JP (1) JP2008505123A (ja)
WO (1) WO2006085975A2 (ja)

Cited By (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN102845457A (zh) * 2012-09-03 2013-01-02 南通博大生化有限公司 一种油田用防腐杀菌剂
US20150366904A1 (en) * 2013-01-25 2015-12-24 Otago Innovation Limited Assembly of micelle aggregates of surfactant micelles and silver nanoparticles and use as antibacterial agent
US9969885B2 (en) 2014-07-31 2018-05-15 Kimberly-Clark Worldwide, Inc. Anti-adherent composition
US10028899B2 (en) 2014-07-31 2018-07-24 Kimberly-Clark Worldwide, Inc. Anti-adherent alcohol-based composition
US10238107B2 (en) 2014-07-31 2019-03-26 Kimberly-Clark Worldwide, Inc. Anti-adherent composition
US10251971B2 (en) 2015-09-03 2019-04-09 The Administrators Of The Tulane Educational Fund Compositions and methods for multipurpose disinfection and sterilization solutions
US11168287B2 (en) 2016-05-26 2021-11-09 Kimberly-Clark Worldwide, Inc. Anti-adherent compositions and methods of inhibiting the adherence of microbes to a surface
US11737458B2 (en) 2015-04-01 2023-08-29 Kimberly-Clark Worldwide, Inc. Fibrous substrate for capture of gram negative bacteria
US12037497B2 (en) 2016-01-28 2024-07-16 Kimberly-Clark Worldwide, Inc. Anti-adherent composition against DNA viruses and method of inhibiting the adherence of DNA viruses to a surface

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2011019951A1 (en) * 2009-08-12 2011-02-17 Pure Bioscience Formulations and methods employing anhydrous disinfectant

Citations (2)

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US6180584B1 (en) * 1998-02-12 2001-01-30 Surfacine Development Company, Llc Disinfectant composition providing sustained residual biocidal action
US20020183233A1 (en) * 2000-12-14 2002-12-05 The Clorox Company, Delaware Corporation Bactericidal cleaning wipe

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JPH0742207B2 (ja) * 1987-04-07 1995-05-10 品川燃料株式会社 抗菌性スプレ−用組成物
JPH045209A (ja) * 1990-04-21 1992-01-09 Matsushita Electric Works Ltd 除菌スプレー
JPH0797302A (ja) * 1993-09-29 1995-04-11 Tokuyama Corp 抗菌剤組成物
JPH08311373A (ja) * 1995-05-22 1996-11-26 Tokuyama Corp 抗菌性被膜用光硬化性組成物
US7163589B2 (en) * 2001-05-23 2007-01-16 Argos Associates, Inc. Method and apparatus for decontamination of sensitive equipment
US20030049187A1 (en) * 2001-05-23 2003-03-13 Robert Kaiser Decontamination system and method of decontamination
US20040002550A1 (en) * 2002-06-28 2004-01-01 Mercurio Anthony Fred Post foaming compositions
EP2292715B1 (en) * 2004-04-16 2012-08-22 Honeywell International Inc. Azeotrope-like compositions of tetrafluoropropene and trifluoroiodomethane

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Publication number Priority date Publication date Assignee Title
US6180584B1 (en) * 1998-02-12 2001-01-30 Surfacine Development Company, Llc Disinfectant composition providing sustained residual biocidal action
US20020183233A1 (en) * 2000-12-14 2002-12-05 The Clorox Company, Delaware Corporation Bactericidal cleaning wipe

Cited By (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN102845457A (zh) * 2012-09-03 2013-01-02 南通博大生化有限公司 一种油田用防腐杀菌剂
US20150366904A1 (en) * 2013-01-25 2015-12-24 Otago Innovation Limited Assembly of micelle aggregates of surfactant micelles and silver nanoparticles and use as antibacterial agent
US10064891B2 (en) * 2013-01-25 2018-09-04 Otago Innovation Limited Assembly of micelle aggregates of surfactant micelles and silver nanoparticles and use as antibacterial agent
US9969885B2 (en) 2014-07-31 2018-05-15 Kimberly-Clark Worldwide, Inc. Anti-adherent composition
US10028899B2 (en) 2014-07-31 2018-07-24 Kimberly-Clark Worldwide, Inc. Anti-adherent alcohol-based composition
US10238107B2 (en) 2014-07-31 2019-03-26 Kimberly-Clark Worldwide, Inc. Anti-adherent composition
US10292916B2 (en) 2014-07-31 2019-05-21 Kimberly-Clark Worldwide, Inc. Anti-adherent alcohol-based composition
US11737458B2 (en) 2015-04-01 2023-08-29 Kimberly-Clark Worldwide, Inc. Fibrous substrate for capture of gram negative bacteria
US10251971B2 (en) 2015-09-03 2019-04-09 The Administrators Of The Tulane Educational Fund Compositions and methods for multipurpose disinfection and sterilization solutions
US12037497B2 (en) 2016-01-28 2024-07-16 Kimberly-Clark Worldwide, Inc. Anti-adherent composition against DNA viruses and method of inhibiting the adherence of DNA viruses to a surface
US11168287B2 (en) 2016-05-26 2021-11-09 Kimberly-Clark Worldwide, Inc. Anti-adherent compositions and methods of inhibiting the adherence of microbes to a surface

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EP1768680A2 (en) 2007-04-04
JP2008505123A (ja) 2008-02-21
WO2006085975A3 (en) 2007-06-21

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