WO2017054851A1 - Liquide stable à base d'acide peroxy volatil et composition désinfectante sporicide contenant de l'oxyde d'amine - Google Patents

Liquide stable à base d'acide peroxy volatil et composition désinfectante sporicide contenant de l'oxyde d'amine Download PDF

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Publication number
WO2017054851A1
WO2017054851A1 PCT/EP2015/072464 EP2015072464W WO2017054851A1 WO 2017054851 A1 WO2017054851 A1 WO 2017054851A1 EP 2015072464 W EP2015072464 W EP 2015072464W WO 2017054851 A1 WO2017054851 A1 WO 2017054851A1
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preferred
acid
sporicidal
liquid composition
composition
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PCT/EP2015/072464
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English (en)
Inventor
Katja Teusch
Carola Stingl
Bernhard Meyer
Silke Denzin
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Ecolab Usa Inc.
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Priority to PCT/EP2015/072464 priority Critical patent/WO2017054851A1/fr
Publication of WO2017054851A1 publication Critical patent/WO2017054851A1/fr

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    • 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
    • A01N31/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic oxygen or sulfur compounds
    • A01N31/02—Acyclic 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
    • A01N37/00—Biocides, 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
    • A01N37/02—Saturated carboxylic acids or thio analogues thereof; Derivatives thereof
    • 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
    • A01N37/00—Biocides, 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
    • A01N37/16—Biocides, 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
    • 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
    • A01N59/00—Biocides, pest repellants or attractants, or plant growth regulators containing elements or inorganic compounds

Definitions

  • the invention relates to disinfection compositions that are volatile, surface active, highly effective against bacterial spores and stable as well as a method of manufacture thereof.
  • the invention further relates to the use of such compositions for disinfection purposes in deactivating, inhibiting, disabling, killing, or otherwise sterilizing bacterial spores.
  • Peroxycarboxylic acids are known for use as antimicrobial agents that can kill or otherwise inhibit the growth or proliferation of microbes including bacteria, bacterial spores, yeasts, viruses and fungi.
  • Peroxyacid compositions namely peroxycarboxylic acid compositions, exhibit useful antimicrobial and bleaching activity.
  • Conventional peroxycarboxylic acid compositions typically include short chain peroxycarboxylic acids or mixtures of short chain
  • peroxycarboxylic acids and medium chain peroxycarboxylic acids.
  • peroxyacid compositions have a number of limitations, including low volatility, stability concerns, malodor problems and insufficient micro efficacy against certain microorganisms.
  • peroxyacid compositions such as mixed peroxycarboxylic acid compositions, having improved antimicrobial efficacy compared to conventional peroxyacid compositions due in part to the solubilization of the mixed peroxyacid compositions using esters.
  • This reference further relates to methods employing the enhanced microbial efficacy compositions at reduced temperatures, including for example, use in aseptic cleaning.
  • peroxyacid compositions include an alcohol or esters for the solubilization of the peroxyacids to generate compositions having a lower use concentration. Preferably, up to 5% to about 15% alcohol might be used.
  • peroxyacid compositions have a broad spectrum of antimicrobial properties, many have inadequate activity against hard to kill pathogens, including bacterial spores, fungal spores, and fungi. As a result, killing, inactivating, or otherwise reducing the active population of bacterial spores and fungi on surfaces is particularly difficult.
  • the bacterial spore-forming microorganisms of the Bacillus species are especially important to be aware of during food packaging, particularly during cold or hot aseptic filling of food and beverage, or pharmaceutical, products.
  • Microorganisms of the Bacillus species include Bacillus atropheaus, Bacillus cereus, Bacillus mycoides, Bacillus subtilis, Bacillus anthracis, and Bacillus thuringiensis. These latter microorganisms share many phenotypical properties, have a high level of chromosomal sequence similarity, and are known enterotoxin producers. Bacillus cereus is one of the most problematic because Bacillus cereus has been identified as possessing increased resistance to germicidal chemicals used to decontaminate environmental surfaces.
  • a further object of the invention is an improved peroxyacid composition with enhanced microbial efficacy for targeting endospore-forming bacilli type bacteria.
  • a further object of the invention is a method of use for applications employing a lower use concentration of a peroxyacid composition having enhanced microbial efficacy.
  • a further object of the invention is to provide improved peroxyacid compositions and methods for using the compositions for clean in place (CIP) applications, for example cleaning of tanks, lines, pumps and other process equipment used for processing typically liquid product streams of beverages, in particular for cleaning milking machines.
  • CIP clean in place
  • a still further object of the invention is to provide improved peroxyacid compositions and methods for using the compositions for clean out of place (COP) applications, for example cleaning the interior and exterior surfaces of a wide variety of parts, such as ceramic surfaces, metal surfaces, walls in, wash tanks, soaking vessels, mop buckets, holding tanks, scrub sinks, vehicle parts washers, non-continuous batch washers and systems, and the like.
  • COP clean out of place
  • the disclosure provides a sporicidal liquid composition comprising:
  • IT2 and R 3 J are same or independent selected from an aliphatic substituent, an aromatic substituent, a heterocyclic substituent or an alicyclic substituent, or R 2 and/or R 3 are a hydroxyalkyl of 1 to 3 carbon atoms, or R 2 and R 3 are linked to form a ring structure;
  • the remainder to 100% by weight is water; wherein the weight- % is based on the total weight of the sporicidal liquid composition.
  • the disclosure provides a sporicidal liquid composition comprising:
  • R 1 is selected from Cg to C 18 ,
  • R 3 J are same or independent from each other selected from Q to C 3
  • R 2 and/or R 3 are a hydroxyalkyl of 1 to 3 carbon atoms
  • At least one organic C 2 to Cg peroxycarboxylic acid and at least one C 2 to Cg carboxylic acid are selected from the group comprising of peracetic acid, acetic acid, peroxypropionic acid, propionic acid, peroxyoctanoic acid, octanoic acid, mixtures of peracetic acid and acetic acid, mixtures of peroxypropionic acid and propionic acid, mixtures of octanoic acid and peroxyoctanoic and/or a mixture of peracetic acid, acetic acid, octanoic acid and peroxyoctanoic;
  • the remainder to 100% by weight is water, based on the total weight of the sporicidal liquid composition.
  • the disclosure provides a sporicidal liquid composition comprising:
  • R 1 is selected from Cg to C 18 , preferably Cio to Ci 6 ,
  • R 2" and R 3 J are same or independent from each other selected from Q to C 3
  • R 2 and/or R 3 are a hydroxyalkyl of 1 to 3 carbon atoms
  • peroxycarboxylic acid and at least one C 2 to Cg carboxylic acid preferably at least one peroxycarboxylic acid and one carboxylic acid are selected from the group comprising of peracetic acid, acetic acid, peroxypropionic acid, propionic acid, peroxyoctanoic acid, octanoic acid, mixtures of peracetic acid and acetic acid, mixtures of peroxypropionic acid and propionic acid, mixtures of octanoic acid and peroxyoctanoic and/or a mixture of peracetic acid, acetic acid, octanoic acid and peroxyoctanoic, wherein the total amount of peroxyacid is present in an amount of from > 0.01 wt.-% to about ⁇ 5 wt.-%, preferably > 0.05 wt.-% to about ⁇ 2 wt.-%, further preferred about > 0.1 wt.-% to about ⁇ 1 wt.-%
  • the remainder to 100% by weight is water, based on the total weight of the sporicidal liquid composition.
  • the disclosure provides a sporicidal liquid composition comprising:
  • R 1 is selected from Cg to C 18 , preferably C 10 to Ci 6 ,
  • R 3 J are same or independent from each other selected from Q to C 3
  • R 2 and/or R 3 are a hydroxyalkyl of 1 to 3 carbon atoms, preferably the amine oxide surfactant is dodecyl dimethylamine oxide (DDAO);
  • DDAO dodecyl dimethylamine oxide
  • the disclosure may provide an embodiment of a sporicidal liquid composition, comprising:
  • R 1 is selected from C 8 to C 18 , preferably C 10 to C 16 ,
  • R 3 J are same or independent from each other selected from Ci to C 3
  • R 2 and/or R 3 are a hydroxyalkyl of 1 to 3 carbon atoms, preferably the amine oxide surfactant is dodecyl dimethylamine oxide (DDAO),
  • the remainder to 100% by weight is water; wherein the weight-% is based on the total weight of the of the sporicidal liquid composition.
  • the disclosure may provide an embodiment of a sporicidal liquid composition comprising:
  • R 1 is selected from Cg to C 18 , preferably Cio to Ci 6 ,
  • R 3 J are same or independent from each other selected from Q to C 3
  • R 2 and/or R 3 are a hydroxyalkyl of 1 to 3 carbon atoms, preferably the amine oxide surfactant is dodecyl dimethylamine oxide (DDAO);
  • DDAO dodecyl dimethylamine oxide
  • the remainder to 100% by weight is water; wherein the weight-% is based on the total weight of the sporicidal liquid composition.
  • the disclosure provides an embodiment of a sporicidal liquid composition comprising:
  • amine oxide surfactant having the general formula I:
  • R 1 is selected from Cg to Cig, preferably Cio to Ci 6 ,
  • R 2" and R 3 J are same or independent from each other selected from Ci to C 3
  • R 2 and/or R 3 are a hydroxyalkyl of 1 to 3 carbon atoms, preferably the amine oxide surfactant is dodecyl dimethylamine oxide (DDAO),
  • the remainder to 100% by weight is water; wherein the weight-% is based on the total weight of the sporicidal liquid composition.
  • the disclosure provides a method of manufacture of, wherein the sporicidal liquid composition is obtained by adding the components comprising:
  • R 1 is selected from C 8 to C 18 , preferably C 10 to C 16 ,
  • R 2 and R 3 J are same or independent from each other selected from Q to C 3 hydrocarbon, or R 2 and/or R 3 are a hydroxyalkyl of 1 to 3 carbon atoms;
  • the remainder to 100% by weight is water; wherein the weight-% is based on the total weight of the sporicidal liquid composition.
  • the disclosure provides the use of the stable liquid, volatile peroxy- acid containing sporicidal disinfecting composition for deactivating, inhibiting, disabling, killing and/or sterilizing spores.
  • Other aspects and aspects are encompassed by the disclosure and will become apparent in light of the following description.
  • the disclosure provides a liquid composition that combines several advantages. At first, it is volatile. That means that it evaporates within a short time when applied to a surface. Short time means that 1.0 ml to 3.0 ml of the composition according to the invention placed on the upper surface of a horizontal positioned glass plate of about 10 cm x about 10 cm at a temperature of about 23° C and an air humidity of about 40% evaporates within a time period of about > 2 minutes to about ⁇ 4 minutes. Nevertheless, it is highly efficient and has a long shelf live.
  • composition is surface active. Thus, it is able to spread on non polar as well as on polar surfaces and may emulsify water insoluble liquids.
  • the sporicidal liquid composition is ready-to-use.
  • compositions may be useful for deactivating, inhibiting, disabling, killing and/or sterilizing spores on surfaces of articles used in healthcare, food and beverage industry and any other place, where the reduction of microbial burden is desirable.
  • the sporicidal liquid composition maybe highly effective in deactivating, inhibiting, disabling, killing and/or sterilizing bacterial spores, although it dries very easily, when applied to a surface.
  • the sporicidal liquid composition may be less corrosive, less skin irritating and/or low foaming.
  • the sporicidal liquid composition may feature high sporicidal activity at short contact times, being less metal corrosive and provides significant malodor reduction.
  • the sporicidal liquid compositions according to the invention provide a shelf life of at least 6 months at storage conditions at about 25° C and a sporicidal efficacy against Bacillus subtilis according to EN 13704.
  • by weight refers to the total weight of the composition. For example, if a composition has a total weight of 100 grams and comprises 40% (by weight) of an alcohol, the composition comprises 40 grams of alcohol.
  • sporicidal liquid composition "sporicidal disinfecting composition”, “sporicidal disinfecting composition”, “sporicidal liquid composition” or “disinfecting composition” is simultaneously used.
  • sporicidal liquid agent when used in the context of a sporicidal liquid agent or sporicidal liquid composition, refers to an agent or composition that can kill or otherwise inhibit the growth or proliferation of microbes including, for example, bacteria, viruses, fungi and bacterial spores.
  • the term “trustmicroorganism” refers to any non-cellular or unicellular (including colonial) organism, including all prokaryotes, bacteria (including cyanobacteria), spores, lichens, fungi, protozoa, virinos, viroids, viruses, phages, and algae.
  • sporicidal activity as used in the context of a sporicidal liquid agent or sporicidal liquid composition refers to activity that can kill or otherwise inhibit the growth or proliferation of microbes including bacteria, yeasts, viruses, fungi and bacterial spores.
  • highly effective or efficient when used in the context of a sporicidal liquid composition, refers to a composition that can kill spores according to EN 13704.
  • stable refers to physical and/or chemical stability. Physical stability refers to retaining an original physical form without undergoing phase change or separation, discoloration, and the like. Chemical stability refers to resistance to impurity generation and degradation of active components.
  • storage stable refers to a composition according to the invention, preferably in the form of a ready to use product, that shows no phase separation at about 40° C for a period of at least 7 days, and preferably the composition shows no phase separation at about 40° C for a period of at least 9 weeks.
  • ready to use refers to a composition that can be directly applied to a surface to be disinfected without any further dilution.
  • the term “bulsurface” refers to a surface of a healthcare setting, a medical instrument, , a tool, a machine, equipment, a structure, a building, or the like that is employed as part of a food processing, preparation, or storage activity.
  • healthcare settings include hospitals, doctor's offices and long term care facilities.
  • food processing surfaces include surfaces of food processing or preparation equipment, e.g., slicing, canning, or transport equipment, including flumes, of food processing wares, e.g., utensils, dishware, wash ware, and bar glasses), and of floors, walls, or fixtures of structures in which food processing occurs.
  • Food processing surfaces are found and employed in milking machines, food anti-spoilage air circulation systems, aseptic packaging sanitizing, food refrigeration and cooler cleaners and sanitizers, ware washing sanitizing, blancher cleaning and sanitizing, food packaging materials, cutting board additives, third-sink sanitizing, beverage chillers and warmers, meat chilling or scalding waters, auto dish sanitizers, sanitizing gels, cooling towers, food processing antimicrobial garment sprays, and non-to-low-aqueous food preparation lubricants, oils, and rinse additives.
  • the term “bulware” refers to items such as eating and cooking utensils, dishes, and other hard surfaces such as showers, sinks, toilets, bathtubs, countertops, windows, mirrors, transportation vehicles, and floors.
  • the term “bula” refers to variation in the numerical quantity that can occur, for example, through typical measuring and liquid handling procedures used for making concentrates or use solutions in the real world; through inadvertent error in these procedures; through differences in the manufacture, source, or purity of the ingredients used to make the compositions or carry out the methods; and the like.
  • the term “bulabout” also encompasses amounts that differ due to different equilibrium conditions for a composition resulting from a particular initial mixture. Whether or not modified by the term fittingabout" the claims include equivalents to the quantities.
  • composition containing any compound includes a composition having two or more compounds.
  • the phrases “paymentobjectionable odor”, howeveroffensive odor”, or “malodor”, refer to a sharp, pungent, or acrid odor or atmospheric environment from which a typical person withdraws if they are able to. Hedonic tone provides a measure of the degree to which an odor is pleasant or unpleasant.
  • An "objectionable odor”, “offensive odor”, or “malodor” has an hedonic tone rating it as unpleasant as or more unpleasant than a solution of > 5 wt-% acetic acid, propionic acid, butyric acid, or mixtures thereof.
  • the stable liquid, volatile peroxy- acid containing sporicidal disinfecting composition disclosed herein may be effective for deactivating, inhibiting, disabling, killing, or otherwise sterilizing spores with > 3 log reduction according to EN 13704.
  • any numerical value recited herein includes all values from the lower value to the upper value, i.e., all possible combinations of numerical values between the lowest value and the highest value enumerated are to be considered to be expressly stated in this application.
  • concentration range is stated as 1% to 50%, it is intended that values such as 2% to 40%, 10% to 30%, or 1% to 3%, etc., are expressly enumerated in this specification. These are only examples of what is specifically intended.
  • the stable liquid, volatile peroxyacid containing sporicidal disinfecting composition described herein include at least one C 2 to Cg peroxyorganic acid. According to one aspect the stable liquid, volatile peroxyacid containing sporicidal disinfecting composition
  • described herein may include at least one C 2 to C 3 peroxyorganic acid.
  • C 2 to C 3 peroxycarboxylic acids examples include, but are not limited to peroxyacetic acid, peroxypropionic acid, as well as their branched isomers and mixtures thereof.
  • the stable liquid, volatile peroxyacid containing sporicidal disinfecting composition described herein may include a peroxyacetic acid.
  • peroxyacetic acid and/or peroxyoctanoic acid may be preferred and peroxyacetic acid as the sole peroxy acid may be most preferred.
  • the sporicidal liquid composition may comprise about > 0.01 wt.-% to about ⁇ 5 wt- %, preferably > 0.05 wt.-% to about ⁇ 2 wt.-%, further preferred about > 0.1 wt.-% to about ⁇ 1 wt.-% and more preferred about > 0.2 wt.-% to about ⁇ 0.5 wt.-%, of a C 2 to Cg
  • peroxyorganic acid preferably peroxyacetic acid, based on the total weight of the sporicidal liquid composition.
  • the sporicidal liquid composition may comprise about > 0.01 wt.-% to about ⁇ 5 wt- %, preferably > 0.05 wt.-% to about ⁇ 2 wt.-%, further preferred about > 0.1 wt.-% to about ⁇ 1 wt.-% and more preferred about > 0.2 wt.- to about ⁇ 0.5 wt.-%, of a C 2 to C 3 peroxyorganic acid, preferably peroxyacetic acid, based on the total weight of the sporicidal liquid composition.
  • the stable liquid sporicidal disinfecting composition according to the invention described herein include at least one C 2 to organic acid.
  • the stable liquid, volatile, organic acid containing sporicidal disinfecting composition described herein may include at least one C 2 to C 3 organic acid.
  • Suitable C 2 to C 3 carboxylic acids include, but are not limited to acetic acid, propionic acid, as well as their branched isomers and mixtures thereof.
  • the sporicidal disinfecting composition described herein may include an acetic acid.
  • acetic acid and/or octanoic acid may be preferred and acetic acid as the sole organic acid may be most preferred.
  • the stable liquid, volatile peroxyacid containing sporicidal disinfecting compositions may comprise about > 0 wt.-% to about ⁇ 10 wt.-% or > 0.1 wt.-% to about ⁇ 9 wt.-%, preferably of about > 1 wt.- to about ⁇ 8 wt.-%, further preferred of about > 2 wt.- to about ⁇ 6 wt.-%, and more preferred of about > 3 wt.-% to about ⁇ 4 wt.- , of at least one C 2 to C8 organic acid, preferably of at least one C 2 to C 3 organic acid and more preferred acetic acid, based on the total weight of the sporicidal liquid composition.
  • the stable liquid, volatile peroxyacid containing sporicidal disinfecting compositions may comprise about > 0.5 wt.-% to about ⁇ 10 wt.-%, preferably about > 1 wt.- to about ⁇ 8 wt.-%, further preferred about > 2.5 wt.-% to about ⁇ 5 wt.-% or about > 3 wt.-% to about ⁇ 4 wt.- , of at least one C 2 to Cg organic acid, preferably of at least one C 2 to C 3 organic acid and more preferred acetic acid, based on the total weight of the sporicidal liquid composition.
  • the stable liquid, volatile peroxyacid containing sporicidal disinfecting compositions do not contain phthalimidoalkanoic acids and/or their peroxyacids.
  • Phthalimido-hexanoic peroxyacid should not be present.
  • the sporicidal liquid compositions described herein include at least one C 2 to C 4 alcohol.
  • the C 2 to C 4 alcohol can be selected from the group comprising ethanol, n-propanol, iso-propanol, butanol, isobutanol and tert-butanol, wherein ethanol and iso-propanol may be preferred and n-propanol may be most preferred.
  • the sporicidal liquid composition may comprises about > 20 wt.-%, preferably about more than 20 wt.-% to about ⁇ 50 wt.-%, or of about > 25 wt.-% to about ⁇ 45 wt.-%, or about > 25 wt.-% to about ⁇ 35 wt.-%, and in addition preferred of about > 30 wt.-% to about ⁇ 40 wt.-% C 2 to C 4 alcohol, wherein n-propanol is preferred, based on the total weight of the sporicidal liquid composition.
  • the sporicidal liquid composition may comprises about > 25 wt.- to about ⁇ 35 wt.-%, of a C 2 to C 4 alcohol, wherein n-propanol is preferred, based on the total weight of the sporicidal liquid composition.
  • the stable liquid, volatile peroxyacid containing sporicidal disinfecting compositions described herein may include organic phosphonic acids capable of sequestering bivalent metal cations.
  • organic phosphonic acids capable of sequestering bivalent metal cations.
  • Preferred are low molecular weight aliphatic compounds containing at least two anion groups, at least one of which being a phosphonic acid group.
  • Sequestering agent can be selected from the group comprising phosphonic acid, and more preferred the builder is selected from the group comprising aminomethylphosphonic acid, dimethyl methyl phosphonate, l-hydroxyethylidene-1,1- diphosphonic acid, amino tris(methylenephosphonic acid), ethylenediamine tetra(methylene phosphonic acid), tetramethylenediamine tetra (methylene phosphonic acid),
  • HEDP ethylidene-l,l-diphosphonic acid
  • sequestering agents are aminocarboxylates and their derivatives, pyrophosphates, polyphosphates, ethylenediamene and ethylenetriamine derivatives, hydroxyacids, and mono-, di-, and tri-carboxylates and their corresponding acids.
  • the sporicidal liquid composition may comprises about > 0 wt.- to about ⁇ 5 wt.-%, preferably of about > 0.1 wt.-% to about ⁇ 3 wt.-%, further preferred of about > 0.2 wt.- to about ⁇ 2 wt.- , and in addition preferred of about > 0.1 wt.- to about ⁇ 1.0 wt.-% or of about > 0.3 wt.-% to about ⁇ 1.0 wt.-% of a sequestering agent, based on the total weight of the sporicidal liquid composition.
  • the disinfecting composition can be free of a builder.
  • the stable liquid, sporicidal disinfecting compositions described contain an
  • R 1 , R2 , and R 3 may be aliphatic, aromatic, heterocyclic or alicyclic.
  • R 1 can be an C 8 to C 18 alkyl radical
  • R 2 and/or R 3 are alkyl or hydroxyalkyl of 1 to 3 carbon atoms
  • R 2 and R 3 can be linked to each other, e.g. through an oxygen or nitrogen atom, to form a ring structure.
  • An amine oxide can be generated from the corresponding amine and an peroxide agent, such as hydrogen peroxide.
  • Useful water soluble amine oxide surfactants are selected from the octyl, decyl, dodecyl, isododecyl, coconut, or tallow alkyl di-(lower alkyl)amine oxides, specific examples of which are octyldimethylamine oxide, nonyldimethylamine oxide, decyldimethylamine oxide, undecyldimethylamine oxide, dodecyldimethylamine oxide, iso-dodecyldimethyl amine oxide, tridecyldimethylamine oxide, tetradecyldimethylamine oxide,
  • DDAO dodecyl dimethylamine oxide
  • the sporicidal liquid composition comprises of about > 0.01 wt.-% to about ⁇ 5 wt.-%, preferably of about > 0.05 wt.-% to about ⁇ 2 wt.- , further preferred of about > 0.075 wt.-% to about ⁇ 1 wt.- , and more preferred of about > 0.3 wt.-% to about ⁇ 0.6 wt.-%, of at least one amine oxide surfactant having the general formula I, wherein the at least one amine oxide surfactant can be preferably dodecyldimethylamine oxide, based on the total weight of the sporicidal liquid composition.
  • the stable liquid, volatile sporicidal disinfecting composition may comprise the surfactant of formula I in an amount of about > 0.02 wt.- to about ⁇ 2 wt- , preferably of about > 0.06 wt.- to about ⁇ 1.5 wt.- , further preferred of about > 0.1 wt- % to about ⁇ 1 wt.- , and more preferred of about > 0.3 wt.- to about ⁇ 0.6 wt.- , wherein the at least one amine oxide surfactant can be preferably dodecyldimethylamine oxide, based on the total weight of the sporicidal liquid composition.
  • the peroxide agent - also referred to active oxygen source herein - includes at least one peroxygen compound.
  • Exemplary peroxygen compounds for use in the composition of the present invention include hydrogen peroxide, a perborate, a percarbonate and mixtures and derivatives thereof, and preferably hydrogen peroxide.
  • the active oxygen source includes hydrogen peroxide.
  • the stable liquid, volatile peroxyacid containing sporicidal disinfecting compositions may comprises a peroxide agent, preferably hydrogen peroxide, in an amount of about > 2 wt.- to about ⁇ 20 wt.- , preferably of about > 3 wt.- to about ⁇ 15 wt.- , further preferred of about > 5 wt.- to about ⁇ 10 wt.- or of about > 5 wt.- to about ⁇ 15 wt.- , and more preferred of about > 4 wt.- to about ⁇ 9 wt.- or about > 7 wt.- to about ⁇ 9 wt.- .
  • a peroxide agent preferably hydrogen peroxide
  • the sporicidal liquid compositions may comprise the hydrogen peroxide in an excess that means that the sporicidal liquid compositions may comprise about > 5 wt.- and ⁇ 15 wt.- , and more preferred about > 7 wt.- and ⁇ 10 wt- % hydrogen peroxide, based on the total weight of the sporicidal liquid composition.
  • the peroxide agent preferably the hydrogen peroxide
  • the peroxide agent may be added in an excess that means that the sporicidal liquid compositions may comprise about > 5 wt.- and ⁇ 15 wt.- , preferably about > 6 wt.- and ⁇ 10 wt.- and more preferred about > 7 wt.- and ⁇ 9 wt.- hydrogen peroxide, based on the total weight of the sporicidal liquid composition.
  • Water is added at 100 wt.-% to the sporicidal liquid composition. That means that water can be added as the remaining component.
  • the water can be tape water or preferably deionized water.
  • the balance of the sporicidal liquid composition can be water, or an aqueous medium.
  • a mixed solvent system, buffer, etc. comprising water as the major component, so as to provide 100 wt.-% of a composition.
  • the sporicidal liquid compositions may comprise a thickening agent, which may act to thicken or increase the viscosity of the composition.
  • a thickener may be added to form a viscous liquid or gel.
  • the sporicidal liquid compositions described herein is free of a thickening agent.
  • composition may also include other additives such as stabilizers, dyes, and the like.
  • Each additive when present, may be added in amounts about > 0 wt.-% to about ⁇ 10 wt.-%, such as about > 0.001 wt.-% to about ⁇ 5% wt.-%, or about > 0.01 wt.-% to about ⁇ 1% wt.-%, based on the sporicidal liquid composition.
  • the sporicidal liquid compositions described herein is free of additives, preferably free of thickening agent and/or dyes.
  • the fragrant component usable for the present invention may comprises at least one specific fragrant material selected from synthetic and natural fragrant materials.
  • the specific fragrant material usable for the present invention is required to be capable of masking the irritating odor of for example acetic acid and/or peroxy acetic acid, by the fragrance thereof, without reducing a stability of the effective ingredient in the oxidizing component; chemically stable in the presence of the oxidizing component so that the fragrance-generating property thereof is not reduced by the oxidizing component; and capable of being stably and uniformly solubilized in the appearance of a transparent liquid in the oxidizing component with the aid of the surfactant component.
  • the fragrant component comprises a mixture of two or more fragrant materials selected in consideration of the inherent fragrance thereof and the above-mentioned requirements.
  • the fragrant component usually comprises a fragrance composition.
  • the fragrant compounds, usable for the present invention are classified into hydrocarbons, alcohols, esters, ketones, lactones, acetals, aldehydes and ethers as indicated below.
  • the synthetic fragrant compounds and the natural fragrant materials include the following compounds and materials selected from the group comprising hydrocarbons, such as p-cymene; alcohols, such as borneol, cinnamic alcohol, dimethyl benzyl carbinol, 1- menthol, fenchyl alcohol, phenyl ethyl alcohol, o-tert-butyl cyclohexanol, 2-sec -butyl cyclohexanol, lauryl alcohol, 2-methyl undecanol, citronellol, dihydro myrcenol, tetrahydro linalool, dipropylene glycol, hexylene glycol, p-tert-butyl cyclohexanol,
  • esters such as ethylene tridecane dioate, amyl salicylate, dimethyl benzyl carbinyl acetate, fenchyl acetate, n-hexyl salicylate, iso-bornyl acetate, o-tert- butyl cyclohexyl acetate, p-tert-butyl cyclohexyl acetate, phenyl ethyl acetate, tricyclodecenyl acetate, styrallyl acetate, methyl salicylate, allylamyl glycolate, allyl capronate, ethyl capronate, ethyl cinnamate, geranyl a
  • the fragrant component is present preferably in a content of about > 0.1 wt.- to about ⁇ 1.0 wt.-%, and most preferred about > 0.3 wt.-% to about ⁇ 0.5 wt.-%, based on the total weight of the sporicidal liquid composition according to the invention.
  • Neutrawash available from the company Fragrance Resources GmbH, located in Hamburg, Germany, as a fragrant component, can be most preferred.
  • Neutrawash can be preferably used in a content of about > 0.01 wt.-% to about ⁇ 2.0% by weight, more preferably about > 0.1 wt.-% to about ⁇ 1.0 wt- %, and most preferred about > 0.3 wt.-% to about ⁇ 0.5 wt.-%, based on the total weight of the sporicidal liquid composition according to the invention.
  • the sporicidal liquid compositions described herein is free of an fragrant.
  • the pH of the sporicidal liquid composition can be adjusted with acid or base, if necessary; wherein the acid or base used to adjust the pH differs from the other components of the sporicidal liquid composition.
  • Exemplary acids include citric acid, phosphoric acid, gluconic acid, lactic acid and glycolic acid.
  • the acid is citric acid.
  • the sporicidal liquid composition is free of an additional acid or base to adjust the pH.
  • the sporicidal liquid composition can be free of citric acid, phosphoric acid, gluconic acid, lactic acid and/or glycolic acid.
  • an alkylamine can be used to adjust the pH to be less acidic.
  • exemplary bases include sodium hydroxide, potassium hydroxide, and preferably
  • alkylamines further preferred ethanolamine and/or propanolamine, more preferred
  • the sporicidal liquid composition is free of an additional base to adjust the pH.
  • the sporicidal liquid composition can be free of hydroxide, potassium hydroxide, alkylamines, ethanolamine, propanolamine,
  • the sporicidal liquid composition may comprises about > 0 wt- % to about ⁇ 5 wt.- , preferably of about > 0.05 wt.- to about ⁇ 1 wt.- , further preferred of about > 0.05 wt.- to about ⁇ 0.5 wt.- , and more preferred of about > 0.1 wt.- to about ⁇ 0.2 wt.- or about 0.15 wt.- , of an acid and/or base to adjust the pH, wherein the acid and/or base differs from the other components of the sporicidal liquid composition, preferably the base is selected from the group comprising alkylamine, further preferred ethanolamine and/or propanolamine, more preferred monoethanolamine, diethanolamine, n- monopropanolamine, n-dipropan
  • the pH of the stable liquid, volatile peroxyacid containing sporicidal disinfecting compositions can affect both stability of the formulation and the sporicidal activity. For example, lower pH may increase the sporicidal activity.
  • the sporicidal liquid compositions disclosed herein have a pH that is suitably selected to balance sporicidal efficacy.
  • the sporicidal liquid composition has a pH in the range of about > 1 pH to about ⁇ 8 pH, preferably about > 1.5 pH to about ⁇ 7 pH, further preferred of about > 2 pH to about ⁇ 6 pH, more preferred of about > 2.5 pH to about ⁇ 5 pH, and most preferred of about > 3 pH to about ⁇ 4 pH.
  • the pH of the sporicidal liquid composition may be about > 2.5 to about ⁇ 4.5. Accordingly, the pH may be about > 3.0 to about ⁇ 4.5, about > 4.0 to about ⁇ 4.5, about > 3.0 to about ⁇ 4.0, about > 3.5 to about ⁇ 3.8, about > 3.6 to about ⁇ 3.7, about > 3.5, about > 3.6, about > 3.7 or about > 3.8.
  • a composition may have a pH of up to about 2.5, up to about 3.0, up to about 3.5, up to about 3.6, up to about 3.7, up to about 3.8, up to about 3.9, up to about 4.0, up to about 4.5, at least about 2.5, at least about 3.0, at least about 3.5, at least about 3.6, at least about 3.7, at least about 3.8, at least about 3.9, or at least about 4.0.
  • the sporicidal liquid composition may be free of an additional acid or base to adjust the pH.
  • the stable liquid, volatile peroxyacid containing sporicidal disinfecting composition may comprise: - about > 0.01 wt.-% to about ⁇ 5 wt.-%, preferably of about > 0.05 wt.-% to about ⁇ 2 wt- %, further preferred of about > 0.075 wt.-% to about ⁇ 1 wt.- , and more preferred of about > 0.3 wt.-% to about ⁇ 0.6 wt.-%, of at least one amine oxide surfactant, having the general formula I:
  • IT2 and R 3 J are same or independent selected from an aliphatic substituent, an aromatic substituent, a heterocyclic substituent or an alicyclic substituent, or R 2 and/or R 3 are a hydroxyalkyl of 1 to 3 carbon atoms, or R 2 and R 3 are linked to form a ring structure;
  • the base is selected from the group comprising alkylamine, further preferred ethanolamine and/or propanolamine, more preferred monoethanolamine, diethanolamine, n-monopropanolamine, n-dipropanolamine monoisopropanolamine, diisopropanolamine, triethanolamine, n-tripropanolamine and/or triisopropanolamine, and most preferred triethanolamine;
  • the stable liquid, volatile peroxyacid containing sporicidal disinfecting composition may comprise:
  • R 1 1 , IT2 and R 3 J are same or independent selected from an aliphatic substituent, an aromatic substituent, a heterocyclic substituent or an alicyclic substituent, or R 2 and/or R 3 are a hydroxyalkyl of 1 to 3 carbon atoms, or R 2 and R 3 are linked to form a ring structure;
  • the base is selected from the group comprising alkylamine, further preferred ethanolamine and/or propanolamine, more preferred monoethanolamine, diethanolamine, n-monopropanolamine, n-dipropanolamine monoisopropanolamine, diisopropanolamine, triethanolamine, n-tripropanolamine and/or triisopropanolamine, and most preferred triethanolamine;
  • the stable liquid, volatile peroxyacid containing sporicidal disinfecting composition may comprise:
  • R 1 is selected from C& to Ci 8 ,
  • R 2 and R 3 J are same or independent from each other selected from Ci to C 3 hydrocarbon, or R 2 and/or R 3 are a hydroxyalkyl of 1 to 3 carbon atoms;
  • the base is selected from the group comprising alkylamine, further preferred ethanolamine and/or propanolamine, more preferred monoethanolamine, diethanolamine, n-monopropanolamine, n-dipropanolamine monoisopropanolamine, diisopropanolamine, triethanolamine, n-tripropanolamine and/or triisopropanolamine, and most preferred triethanolamine;
  • the stable liquid, volatile peroxyacid containing sporicidal disinfecting composition may comprise:
  • R 1 is selected from Cg to C 18 ,
  • R 3 J are same or independent from each other selected from Q to C 3
  • the base is selected from the group comprising alkylamine, further preferred ethanolamine and/or propanolamine, more preferred monoethanolamine, diethanolamine, n-monopropanolamine, n-dipropanolamine monoisopropanolamine, diisopropanolamine, triethanolamine, n-tripropanolamine and/or triisopropanolamine, and most preferred triethanolamine; - about > 0 wt.-%
  • the stable liquid, volatile peroxyacid containing sporicidal disinfecting composition may comprise:
  • R 1 is selected from C 8 to C 18 ,
  • R 3 J are same or independent from each other selected from Ci to C 3
  • the stable liquid, volatile peroxyacid containing sporicidal disinfecting composition may comprise:
  • R 1 is selected from C 8 to C 18 ,
  • R 3 J are same or independent from each other selected from Q to C 3 hydrocarbon, or
  • R 2 and/or R 3 are a hydroxyalkyl of 1 to 3 carbon atoms
  • the base is selected from the group comprising alkylamine, further preferred ethanolamine and/or propanolamine, more preferred monoethanolamine, diethanolamine, n-monopropanolamine, n-dipropanolamine monoisopropanolamine, diisopropanolamine, triethanolamine, n-tripropanolamine and/or triisopropanolamine, and most preferred triethanolamine;
  • the stable liquid, volatile peroxyacid containing sporicidal disinfecting composition has a pH in the range of about > 2.5 pH to about ⁇ 5 pH, and most preferred of about > 2.5 pH to about ⁇ 4 pH.
  • the stable liquid, volatile peroxyacid containing sporicidal disinfecting composition may comprise:
  • R 1 is selected from C 8 to C 18 ,
  • R 3 J are same or independent from each other selected from Q to C 3 hydrocarbon, or
  • R 2 and/or R 3 are a hydroxyalkyl of 1 to 3 carbon atoms, wherein the amine oxide surfactant is preferably laurylamine oxide;
  • At least one sequestering agent preferably phosphonic acid, and more preferred 1 -hydroxy ethylidene-l,l-diphosphonic acid;
  • the base is selected from the group comprising alkylamine, further preferred ethanolamine and/or propanolamine, more preferred monoethanolamine, diethanolamine, n- monopropanolamine, n-dipropanolamine monoisopropanolamine, diisopropanolamine, triethanolamine, n-tripropanolamine and/or triisopropanolamine, and most preferred triethanolamine;
  • the stable liquid, volatile peroxyacid containing sporicidal disinfecting composition may comprise:
  • amine oxide surfactant having the general formula I:
  • R 1 is selected from C 10 to C 14 ,
  • R 3 J are same or independent from each other selected from Ci to C 3 hydrocarbon, or
  • R 2 and/or R 3 are a hydroxyalkyl of 1 to 3 carbon atoms, wherein the amine oxide surfactant is preferably laurylamine oxide;
  • peroxyacetic acid and/or peroxypropanoic acid preferably peroxyacetic acid
  • the base is selected from the group comprising alkylamine, further preferred ethanolamine and/or propanolamine, more preferred monoethanolamine, diethanolamine, n- monopropanolamine, n-dipropanolamine monoisopropanolamine, diisopropanolamine, triethanolamine, n-tripropanolamine and/or triisopropanolamine, and most preferred triethanolamine;
  • the stable liquid, volatile peroxyacid containing sporicidal disinfecting composition may comprise:
  • amine oxide surfactant having the general formula I:
  • R 1 is selected from C 10 to C 14 ,
  • R 3 J are same or independent from each other selected from Ci to C 3 hydrocarbon, or
  • R 2 and/or R 3 are a hydroxyalkyl of 1 to 3 carbon atoms, wherein the amine oxide surfactant is preferably laurylamine oxide;
  • peroxyacetic acid and/or peroxypropanoic acid preferably peroxyacetic acid
  • At least one sequestering agent preferably phosphonic acid, and more preferred 1 -hydroxy ethylidene-l,l-diphosphonic acid;
  • the base is selected from the group comprising alkylamine, further preferred ethanolamine and/or propanolamine, more preferred monoethanolamine, diethanolamine, n- monopropanolamine, n-dipropanolamine monoisopropanolamine, diisopropanolamine, triethanolamine, n-tripropanolamine and/or triisopropanolamine, and most preferred triethanolamine;
  • the stable liquid, volatile peroxyacid containing sporicidal disinfecting composition may comprise:
  • the base is selected from the group comprising alkylamine, further preferred ethanolamine and/or propanolamine, more preferred monoethanolamine, diethanolamine, n- monopropanolamine, n-dipropanolamine monoisopropanolamine, diisopropanolamine, triethanolamine, n-tripropanolamine and/or triisopropanolamine, and most preferred triethanolamine;
  • the stable liquid, volatile peroxyacid containing sporicidal disinfecting composition has a pH in the range of about > 2.5 pH to about ⁇ 5 pH, and most preferred of about > 2.5 pH to about ⁇ 4 pH.
  • the composition has a pH in the range of about > 1 pH to about ⁇ 8 pH, preferably about > 1.5 pH to about ⁇ 7 pH, further preferred of about > 2 pH to about ⁇ 6 pH, more preferred of about > 2.5 pH to about ⁇ 5 pH, and most preferred of about > 2.5 pH to about ⁇ 4 pH.
  • the stable liquid, volatile peroxyacid containing sporicidal disinfecting composition may comprise:
  • the base is selected from the group comprising alkylamine, further preferred ethanolamine and/or propanolamine, more preferred monoethanolamine, diethanolamine, n- monopropanolamine, n-dipropanolamine monoisopropanolamine, diisopropanolamine, triethanolamine, n-tripropanolamine and/or triisopropanolamine, and most preferred triethanolamine;
  • the stable liquid, volatile peroxyacid containing sporicidal disinfecting composition has a pH in the range of about > 2.5 pH to about ⁇ 5 pH, and most preferred of about > 2.5 pH to about ⁇ 4 pH.
  • the composition has a pH in the range of about > 1 pH to about ⁇ 8 pH, preferably about > 1.5 pH to about ⁇ 7 pH, further preferred of about > 2 pH to about ⁇ 6 pH, more preferred of about > 2.5 pH to about ⁇ 5 pH, and most preferred of about > 2.5 pH to about ⁇ 4 pH.
  • the sporicidal liquid composition maybe used for disinfection, preferably for deactivating, inhibiting, disabling, killing, and/or sterilizing bacterial spores.
  • the sporicidal liquid composition maybe used for example for deactivating, inhibiting, disabling, killing and/or sterilizing spores from surgical, medical, and dental instruments, including endoscopes and any kind of equipment or building surface in healthcare settings, like hospitals, doctor's offices and long-term care facilities.
  • the sporicidal liquid compositions may be generally prepared by any appropriate manufacturing processes and using any appropriate manufacturing equipment such as are known in the art.
  • the various formulation components are sequentially added to water, with stirring between each addition to ensure dissolution and/or dispersion of the previous component.
  • a formulation may be prepared by first adding hydrogen peroxide to water with stirring. This may be followed by addition of one or more of the other components sequentially or simultaneously.
  • compositions may be prepared at ambient temperature.
  • a method of manufacture of the sporicidal liquid composition include, adding the components comprising:
  • Rl is selected from C 10 to C 18 ;
  • R2 and R3 are same or independent from each other selected from Q to C 3 , or R2 and/or R3 is hydroxylated;
  • - peroxide agent preferably hydrogen peroxide
  • Another method of manufacture of the sporicidal liquid composition include, adding the components comprising:
  • Rl is selected from C 10 to C 18 ;
  • R2 and R3 are same or independent from each other selected from Q to C 3 , and/or R3 is hydroxylated;
  • the method of manufacture of the sporicidal liquid composition include, adding the components in an amount comprising: - about > 0.01 wt.-% to about ⁇ 5 wt.-%, preferably of about > 0.05 wt.-% to about ⁇ 2 wt- %, further preferred of about > 0.075 wt.-% to about ⁇ 1 wt.-%, and more preferred of about > 0.3 wt.-% to about ⁇ 0.6 wt.-%, of at least one amine oxide surfactant having the general formula I:
  • Rl is selected from C 10 to C 18 ;
  • R2 and R3 are same or independent from each other selected from Ci to C 3 , or R2 and/or R3 is hydroxylated;
  • the method of manufacture of the sporicidal liquid composition include, adding the components in an amount comprising:
  • the following example was carried out to illustrate the sporicidal efficacy of the disinfectant according to the invention.
  • the sporicidal efficacy of the examples was investigated against a spore suspension of Bacillus subtilis spores (DSM 347).
  • the investigations were performed according to the procedure of the quantitative suspension test according to European norm DIN EN 13704 (2002) .
  • the chosen neutralisation method was in each case the membrane filtration method according to EN 13704.
  • the test concentration was 80%, which is the maximum possible test concentration in this test, i.e. the test samples were used undiluted in the test.
  • the contact time was 2, 5, 15 and30 minutes (El to E4 and Cland C2) and the test temperature was room temperature of 20° C.
  • the tests were performed with an interfering substance of 0.3 g/1 bovine albumin (simulated clean conditions following EN 13704).
  • the incubation was 2, 5, 15 and30 minutes (El to E4 and Cland C2) and the test temperature was room temperature of 20° C.
  • sporicidal efficacy for a disinfectant is shown by demonstrating a reduction of the spores within a contact time of 60 minutes by a factor of 10 (3 log).
  • a liquid sporicidal composition is made from
  • deionized water add to lOOg in total.
  • the pH was about 3
  • a liquid sporicidal composition is made from
  • deionized water add. to lOOg in total.
  • the pH was about 3
  • deionized water add to lOOg in total.
  • the pH was 3
  • deionized water add. to lOOg in total.
  • the pH was about 3
  • deionized water add. to lOOg in total.
  • the pH was about 3
  • deionized water add. to lOOg in total.
  • the pH was about 3
  • compositions were prepared by adding the components to water and mixing at room temperature.
  • the samples El to E5 are examples according to the invention and the comparative samples CI and C2 have no dodecyldimethylamine oxide surfactant.

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Abstract

La présente invention concerne un liquide stable, composition désinfectante sporicide contenant de l'acide peroxy volatil, efficace dans la désactivation, l'inhibition, l'inactivation, la destruction, et/ou la stérilisation de spores bactériennes, comprenant : au moins un tensioactif à base d'oxyde d'amine, ayant la formule générale I : R1, R2 et R3 étant identiques ou indépendamment sélectionnés à partir d'un substituant aliphatique, un substituant aromatique, un substituant hétérocyclique ou un substituant alicyclique, ou R2 et/ou R3 étant un hydroxyalkyle de 1 à 3 atomes de carbone, ou R2 et R3 étant liés de façon à former une structure cyclique ; environ ≥ 20 % en poids à environ ≤ 50 % en poids d'au moins un alcool C2 à C4 ; environ ≥ 0,05 % en poids à environ < 10 % en poids d'au moins un acide carboxylique organique C2 à C8 et au moins un acide peroxycarboxylique C2 à C8 ; environ ≥ 2 % en poids à environ ≤ 20 % en poids d'un agent peroxyde ; et le complément à 100 % en poids est constitué d'eau ; le poids en % étant basé sur le poids total de la composition liquide sporicide.
PCT/EP2015/072464 2015-09-29 2015-09-29 Liquide stable à base d'acide peroxy volatil et composition désinfectante sporicide contenant de l'oxyde d'amine WO2017054851A1 (fr)

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Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN116509895A (zh) * 2023-07-04 2023-08-01 山东利尔康医疗科技股份有限公司 一种低浓度过氧乙酸的手消毒液及制备方法
JP7365078B1 (ja) 2022-05-30 2023-10-19 ミテジマ化学株式会社 抗ウイルス性層状リン酸アルミニウムおよびそれを含有する抗ウイルス性組成物

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US6479454B1 (en) * 2000-10-05 2002-11-12 Ecolab Inc. Antimicrobial compositions and methods containing hydrogen peroxide and octyl amine oxide
WO2013009754A2 (fr) * 2011-07-14 2013-01-17 Ecolab Usa Inc. Compositions antimicrobiennes améliorées à base de peracides et leurs procédés d'utilisation à des températures réduites en nettoyage aseptique

Patent Citations (2)

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Publication number Priority date Publication date Assignee Title
US6479454B1 (en) * 2000-10-05 2002-11-12 Ecolab Inc. Antimicrobial compositions and methods containing hydrogen peroxide and octyl amine oxide
WO2013009754A2 (fr) * 2011-07-14 2013-01-17 Ecolab Usa Inc. Compositions antimicrobiennes améliorées à base de peracides et leurs procédés d'utilisation à des températures réduites en nettoyage aseptique

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP7365078B1 (ja) 2022-05-30 2023-10-19 ミテジマ化学株式会社 抗ウイルス性層状リン酸アルミニウムおよびそれを含有する抗ウイルス性組成物
CN116509895A (zh) * 2023-07-04 2023-08-01 山东利尔康医疗科技股份有限公司 一种低浓度过氧乙酸的手消毒液及制备方法
CN116509895B (zh) * 2023-07-04 2023-09-12 山东利尔康医疗科技股份有限公司 一种低浓度过氧乙酸的手消毒液及制备方法

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