WO2011129829A1 - Α-cétoalkylperacides et leurs procédés de production et d'utilisation - Google Patents

Α-cétoalkylperacides et leurs procédés de production et d'utilisation Download PDF

Info

Publication number
WO2011129829A1
WO2011129829A1 PCT/US2010/031245 US2010031245W WO2011129829A1 WO 2011129829 A1 WO2011129829 A1 WO 2011129829A1 US 2010031245 W US2010031245 W US 2010031245W WO 2011129829 A1 WO2011129829 A1 WO 2011129829A1
Authority
WO
WIPO (PCT)
Prior art keywords
antimicrobial
bacteria
product
alkyl
compound
Prior art date
Application number
PCT/US2010/031245
Other languages
English (en)
Inventor
Edwin D. Neas
John D. Skinner
Original Assignee
Chata Biosystems, 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 Chata Biosystems, Inc. filed Critical Chata Biosystems, Inc.
Priority to PCT/US2010/031245 priority Critical patent/WO2011129829A1/fr
Publication of WO2011129829A1 publication Critical patent/WO2011129829A1/fr

Links

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
    • 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
    • A01N37/42—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 within the same carbon skeleton a carboxylic group or a thio analogue, or a derivative thereof, and a carbon atom having only two bonds to hetero atoms with at the most one bond to halogen, e.g. keto-carboxylic acids
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C409/00—Peroxy compounds
    • C07C409/24—Peroxy compounds the —O—O— group being bound between a >C=O group and hydrogen, i.e. peroxy acids

Definitions

  • the present invention relates to a-keto alkylperacids and methods for producing and using the same.
  • compositions and methods for reducing and/or eliminating microbial organisms from various surfaces Conventional antimicrobial cleansing products such as hard surface cleaners and surgical disinfectants are typically formulated to provide bacteria removal during washing. Only a few such products have been shown to provide a residual effectiveness against Gram-positive bacteria; however, even such compositions provide only limited residual effectiveness against Gram-negative bacteria.
  • residual effectiveness it is meant that the subject antimicrobial controls microbial growth on a substrate by either preventing growth of microbes or engaging in continuous kill of microbes for some period of time following the washing and/or rinsing process.
  • Vegetative bacteria are bacteria or microogranisms that can grow and reproduce in rich, moist soil where many nutrients are available. The actively growing bacteria in these conditions are referred to as “vegetative cells.” Many types of bacteria and fungi can flourish under these conditions. Some examples of bacteria and fungi that can actively reproduce in this kind of soil are Bacillus, Streptomyces, Pseudomonas, Micrococcus, Mycobacterium, and Clostridium. Mycobacterium tuberculosis can cause the disease tuberculosis, and
  • Colstridium botulinum can cause botulism poisoning.
  • Bacillus and Clostridium produce an endospore inside each vegetative cell. Once the vegetative cell (active bacteria) no longer has enough nutrients or moisture to survive, it releases the endospore. The endospore can remain viable for very long periods. When the right conditions return for growth, the endospore creates another vegetative cell, and the bacteria becomes active again. Some fungi produce spores in a similar fashion.
  • Some aspects of the invention provide a-keto alkylperacids and methods for producing and using the same. Such methods typically comprise contacting an a-keto alkylcarboxylic acid or a salt thereof with an oxidizing agent without any significant stirring and under conditions sufficient to produce the a-keto alkylperacid. While a variety of oxidizing agents can be used in such methods, typically the oxidizing agent comprises hydrogen peroxide, barium peroxide, sodium carbonate peroxide, calcium peroxide, sodium perborate, lithium peroxide, magnesium peroxide strontium peroxide, zinc peroxide, potassium superoxide, or a mixture thereof. In some embodiments, the reaction temperature is about 10 °C or less. In other embodiments, the reaction temperature ranges from about - 30 °C to about 10 °C.
  • a-keto alkylperacid is of the formula:
  • R is alkyl of at least two carbon atoms.
  • R is C 2 -C 20 alkyl. Within these embodiments, in some instances, R is C 2 -C 10 alkyl. In some cases, R is selected from the group consisting of ethyl, isopropyl, propyl, butyl, isobutyl, sec -butyl, pentyl, isopentyl, neopentyl, and n-hexyl.
  • Other aspects of the invention provide methods for reducing the amount of microbe on a surface. Such methods typically include contacting the surface with an antimicrobial solution comprising an effective amount of a compound of Formula I.
  • the microbe comprises vegetative bacteria.
  • the microbe comprises bacterial spores, mycobacteria, gram-negative bacteria, vegetative gram-positive bacteria, or a combination thereof.
  • the antimicrobial solution further comprises hydrogen peroxide.
  • the antimicrobial solution comprises at least 40 ppm of the compound of Formula I.
  • Still other aspects of the invention provide methods for reducing the number of infectious vegetative bacteria on a substrate. Such methods include contacting the substrate with an antimicrobial solution comprising an effective amount of a compound of Formula I.
  • Yet other aspects of the invention provide methods for preventing and/or reducing bacteria-related diseases in a mammal that result from the mammal's contact with a bacteria-infected substrate. Such methods can include contacting the substrate with a composition comprising of a compound of Formula I.
  • antimicrobial products comprising a compound of Formula I.
  • the antimicrobial product is a household care product.
  • Exemplary house hold care products include, but are not limited to, hard surface cleaners, deodorizers, fabric care compositions, fabric cleaning compositions, manual dish detergents, automatic dish detergents, floor waxes, kitchen cleaners, and bathroom cleaners.
  • the antimicrobial product is selected from the group consisting of hard surface cleaners, deodorizers, fabric care compositions, fabric cleaning compositions, manual dish detergents, automatic dish detergents, floor waxes, kitchen cleaners, bathroom cleaners, and combinations thereof.
  • the antimicrobial product is a medical device disinfectant.
  • the amount of compound of Formula I that is present in the antimicrobial product is about 100 ppm or less.
  • Other aspects of the invention provide a method for reducing the amount of microbe on a surface, said method comprising contacting the surface with an antimicrobial solution comprising an effective amount of a compound of Formula I.
  • the microbe comprises vegetative bacteria. In other embodiments, the microbe comprises bacterial spores, mycobacteria, gram-negative bacteria, vegetative gram-positive bacteria, or a combination thereof. In one particular embodiment, the microbe comprises bacterial spores.
  • the antimicrobial solution further comprises hydrogen peroxide.
  • the antimicrobial solution comprises at least 40 ppm of a-keto alkylperacid.
  • the antimicrobial solution comprises about 4,000 ppm or less, typically 1,000 ppm or less, often 500 ppm or less, more often 100 ppm or less, and still more often 50 ppm or less amount of the compound of Formula I.
  • the half-life of compound of Formula I in the antimicrobial solution typically is about 120 days or more, often about 180 days or more, and more often about 360 days or more.
  • Yet other aspects of the invention provide a method for reducing the number of infectious vegetative bacteria on a substrate comprising contacting the substrate with an antimicrobial solution comprising an effective amount of a compound of Formula I.
  • Other aspects of the invention provide a method for reducing the number of bacterial spores on a substrate comprising contacting the substrate with an antimicrobial solution comprising an effective amount of a compound of Formula I.
  • Further aspects of the invention provide methods for preventing and/or reducing bacteria-related diseases in a mammal that result from the mammal's contact with a bacteria-infected substrate. Such methods comprise contacting the substrate with a composition comprising a compound of Formula I prior to allowing the mammal to come in contact with the substrate.
  • an antimicrobial product comprising a compound of Formula I.
  • the product is a household care product.
  • the house hold care product is selected from the group consisting of hard surface cleaners, deodorizers, fabric care compositions, fabric cleaning compositions, manual dish detergents, automatic dish detergents, floor waxes, kitchen cleaners, bathroom cleaners, and combinations thereof.
  • the antimicrobial product is selected from the group consisting of hard surface cleaners, deodorizers, fabric care compositions, fabric cleaning compositions, manual dish detergents, automatic dish detergents, floor waxes, kitchen cleaners, bathroom cleaners, and
  • Antimicrobial products of the invention can be used in a wide variety of settings including, but not limited to, in health care facilities such as hospitals,
  • the antimicrobial product is a medical device disinfectant. Still in other embodiments, the antimicrobial product is used as a disinfectant for aseptic filling equipment. Yet in other embodiments, the antimicrobial product is used in an aseptic food processing system. In other embodiments, the antimicrobial product is used as a disinfectant for biofilms in water systems. Still in other embodiments, the antimicrobial product is used as a disinfectant for waste water treatment.
  • the amount of compound of Formula I present in the antimicrobial product is about 100 ppm or less. Still in other embodiments, the half-life of a compound of Formula I is at least 20 days.
  • Figure 1 shows graph of efficacy of peroxy a-keto pyruvic acid against C.
  • Figure 2 is a graph showing efficacy of peroxy a-keto butyric acid against C. difficile at various concentrations.
  • Figure 3 is a graph showing comparison of effectiveness against C. difficile between peroxy pyruvic acid and peroxy a-ketobutyric acid.
  • Figure 4 is a table showing effectiveness of antimicrobial activities of various carboxylic acids and peroxy a-keto carboxylic acids against various microorganisms.
  • a-keto alkylperacid and methods for producing and using the same.
  • alkyl refers to a saturated linear monovalent hydrocarbon moiety of two to twenty, typically two to ten, and often two to eight carbon atoms or a saturated branched monovalent hydrocarbon moiety of three to twenty, typically three to ten, and often three to eight carbon atoms.
  • Exemplary alkyl group include, but are not limited to, ethyl, w-propyl, 2-propyl, tert- butyl, pentyl, and the like.
  • Peracids or peroxyacids refer to carboxylic acids in which the acidic -OH group has been replaced by an -OOH group. They are strong oxidizing agents and are generally unstable. They are most often used as oxidizing agents in various chemical reactions. Peroxy acids are generally not very stable even in solution and decompose to their corresponding carboxylic acid and oxygen. Because most peracids decompose relatively quickly under ambient conditions, they are typically not used for any other purposes except in chemical reactions. Even then, many peroxyacids are synthesized just prior to their use. Some peroxyacids, for example, meta-chloroperoxybenzoic acid (MCPBA), are somewhat stable at a lower temperature as long as they are not in a pure form. Pure MCPBA can be detonated by shock or by sparks. It is therefore, commercially sold as a much more stable mixture that is less than 72% pure.
  • MCPBA meta-chloroperoxybenzoic acid
  • peroxyacids are prepared by electrolytic oxidation of ordinary carboxylic acids or by using a transition metal catalyst and an oxidizing agent or by using a very strong oxidizing agent.
  • electrolytic oxidation typically a high current density must be used to form the peroxyacid in good yield. Such use of a high current density typically increases the cost of producing peroxyacids.
  • Peroxyacids can also be produced using a transition metal catalyst and an oxidizing agent or simply by using a strong oxidizing agent.
  • a strong oxidizing agent in and of itself creates potentially dangerous conditions and increases the high cost of peroxyacid production.
  • use of a transition metal catalyst render the resulting peroxyacid often contaminated with the transition metal.
  • Some methods of the invention for producing a-keto alkylperacids include contacting an a-keto alkylcarboxylic acid or a salt thereof with an oxidizing agent without any significant stirring and under conditions sufficient to produce the a-keto alklperacid.
  • the reaction condition comprises non- stirring conditions where a mixture of the a- keto alkylcarboxylic acid and the oxidizing agent is simply allow to stand without any stirring.
  • stir or “stirring” refers to agitating or act of causing a mixing of the reagents by using an external force such as by using a mechanical stirrer, a magnetic stirrer, a shaker, or any other mechanical, electrical, magnetic, or manual force including simply mixing the reagents manually (e.g., by stirring or shaking).
  • the present inventors have found that by contacting an a-keto alkylcarboxylic acid and an oxidizing agent and letting the mixture stand without any significant mixing, a good yield of the corresponding a-keto alkylperoxyacid can be produced.
  • the yield of the reaction is at least 5 , typically at least 8 , and often at least 12 %.
  • the yield of the a-keto alkylperoxyacid is affected by a variety of reaction conditions and reagents used.
  • One of the factors influencing the yield of a-keto alkylperoxyacid is the reaction temperature.
  • the rate of reaction increases as the temperature increases.
  • a higher reaction temperature can also increase the yield of side-product(s) and/or decomposition of the a-keto alkylperoxyacid that is formed. Therefore, the reaction temperature is typically kept at about 10 °C or below, often at about 4 °C or below, and more often at about - 10 °C or below.
  • the concentration of the reagents can also affect the rate and the yield of a- keto alkylperoxyacid.
  • the initial concentration of the oxidizing agent is generally about 12 M or less, typically about 7 M or less, and often about 1 M or less.
  • reaction time can also affect the yield of a-keto alkylperoxyacid.
  • reaction time ranges from about 4 hrs to about 12 hrs, often from about 6 hrs to about 8 hrs, and more often from about 10 hrs to about 12 hrs.
  • alkylcarboxylic acids Generally any a-keto alkylcarboxylic acid can be used to produce the corresponding a-keto alkylcarboxylic acid.
  • exemplary a-keto carboxylic acids include, but are not limited to, a-keto butyric acid, a-keto valeric acid, a-keto hexanoic acid, etc.
  • Exemplary oxidizing agents that are useful in methods of the invention include, but are not limited to, hydrogen peroxide, barium peroxide, sodium carbonate peroxide, calcium peroxide, sodium perborate, lithium peroxide, magnesium peroxide strontium peroxide, zinc peroxide, potassium superoxide, and the like.
  • reacting are used interchangeably herein, and refer to adding two or more reagents under appropriate conditions to produce the indicated and/or the desired product. It should be appreciated that the reaction which produces the indicated and/or the desired product may not necessarily result directly from the combination of reagents which were initially added, i.e., there may be one or more intermediates which are produced in the mixture which ultimately leads to the formation of the indicated and/or the desired product.
  • the reaction is generally conducted in an aqueous solution.
  • Other solvents such as an organic solvent can also be used in addition to or in place of the aqueous solution. Because it is inexpensive and commercially available in an aqueous solution, typically hydrogen peroxide is used as an oxidizing agent.
  • the ratio of oxidizing agent to a-keto alkylcarboxylic acid typically ranges from about 0.5: 1 to about 2: 1, often about 2: 1 to about 6: 1.
  • compounds and compositions or the invention can be used as a disinfectant.
  • the term “disinfection” refers to removal, destruction, killing, or reducing of at least a significant portion of a pathogenic microorganism population from a surface of an object.
  • methods, compounds and compositions of the invention can be used to reduce at least about 90%, often at least about 95%, more often at least about 98%, still more often at least about 99.9% and most often all of the
  • microorganism includes bacteria, virus, fungi, algae, prion, and other pathogenic organisms known to one skilled in the art.
  • the term "microorganism” includes bacteria, virus, fungi, algae, prion, and other pathogenic organisms known to one skilled in the art.
  • the term "microorganism” includes bacteria, virus, fungi, algae, prion, and other pathogenic organisms known to one skilled in the art.
  • the term "microorganism” includes bacteria, virus, fungi, algae, prion, and other pathogenic organisms known to one skilled in the art.
  • the term “microorganism” includes bacteria, virus, fungi, algae, prion, and other pathogenic organisms known to one skilled in the art.
  • the term “microorganism” includes bacteria, virus, fungi, algae, prion, and other pathogenic organisms known to one skilled in the art.
  • the term “microorganism” includes bacteria, virus, fungi, algae, prion, and
  • microorganism refers to bacteria.
  • Physical sterilization for example, applying steam or other gas via pressurized autoclave— is generally not feasible for disinfection of large spaces and surfaces or sensitive medical equipment.
  • physical sterilization is generally not feasible for disinfection of large spaces and surfaces or sensitive medical equipment.
  • physical sterilization is generally not feasible for disinfection of large spaces and surfaces or sensitive medical equipment.
  • physical sterilization is generally not feasible for disinfection of large spaces and surfaces or sensitive medical equipment.
  • Bacteria found on human skin is typically divided into two groups, namely, resident and transient bacteria.
  • Resident bacteria are Gram-positive bacteria that establish as permanent microcolonies on the surface and outermost layers of the skin. Such bacteria play a fundamental role in preventing the colonization of other, more harmful bacteria and fungi.
  • Transient bacteria are bacteria that are not part of the normal resident of the flora of the skin. Rather, transient bacteria are deposited when airborne contaminated material lands on the skin or when contaminated material is brought into physical contact with such bacteria.
  • Transient bacteria are typically divided into two subgroups: Gram-positive and Gram- negative.
  • Gram-positive bacteria include pathogens such as Staphylococcus aureus,
  • Gram-negative bacteria include pathogens such as Salmonella, Escherichia coli, Klebsiella, Haemophilus, Pseudomonas aeuginosa, Proteus and Shigella dysenteriae. Gram-negative bacteria are generally
  • compositions and methods for reducing and/or eliminating the formation of bacteria and/or viruses are well known.
  • the washing of hard surfaces, food (e.g., fruit or vegetables) and skin, especially the hands, with antimicrobial or non-medicated soap is effective against viruses and bacteria.
  • removal of the viruses and bacteria is due to the surfactant activity of the soap and the mechanical action of the wash procedure, rather than the function of an antimicrobial agent.
  • antimicrobial agent controls microbial growth on a substrate by either preventing growth of microbes or engaging in continuous kill of microbes for some period of time following the washing and/or rinsing process.
  • Iodophors likewise may function as disinfectants at the proper concentrations, but leave stains (residue) and are ofen less effective if any appreciable amount of protein is present.
  • Most heavy metal based antimicrobial agents are toxic and more bacteriostatic than bacteriocidal. Peroxides are widely used to clean skin surfaces and wounds, but they have negligible antimicrobial activity.
  • Microorganisms including bacteria, fungi, algae, viruses, prions and other such microbial entities, can be found within any growth condition or environment where life exists. While many varieties of bacterial microbes are useful or 'friendly' to their animal- hosts, others prove irritating and troublesome— yet, relatively harmless— to manage their populations. Many strains of microbes pose a very serious— and often lethal— risk to the health of co-existent animal populations. Decreasing those troublesome, very serious, and lethal microbial populations under non- sterile conditions requires the use of an antimicrobial agent. Different bacteria show varying degrees of resistance toward a particular disinfectant. Prions tend to be the most-resistant of all microbial entities to antimicrobial agents. Bacterial spores and mycobacteria are generally considered to be the most resistant forms of the bacteria, followed by Gram-negative bacteria, which are generally considered to be more resistant than vegetative Gram-positive bacteria such as the staphylococci and enterococci.
  • the antimicrobial compositions include an a-keto alkylperoxyacid. Surprisingly and unexpectedly, the present inventors have discovered that such compositions are also effective in disinfecting bacterial spores.
  • compositions of the invention can optionally include one or more additional antimicrobial agent (e.g., hydrogen peroxide), a pH neutral diluting solvent (e.g., water), or a combination thereof.
  • additional antimicrobial agent e.g., hydrogen peroxide
  • a pH neutral diluting solvent e.g., water
  • the diluting solvent is a pH neutral liquid solvent adaptable for dissolving the a-keto alkylperoxyacid, e.g., water.
  • compositions can also include an additional agent that can attack the protective protein layer of microbes (for example, non-enveloped viruses or spores) and/or an additional agent that can dissolve the lipid nature of the envelopes or membranes of the microbes.
  • additional antimicrobial agents include organic acids, peroxides, alcohols, and ethers.
  • the concentration of a-keto alkylperoxyacid in solution is about 1,000 ppm or less, typically 500 ppm or less, often 400 ppm or less, more often 200 ppm or less, and most often 100 ppm or less.
  • the composition comprises at least about 2.5% (v/v) of a-keto alkylperoxyacids.
  • compositions of the invention can also comprise a second antimicrobial agent.
  • the amount of second antimicrobial agent can be at least 3% (v/v).
  • Suitable second antimicrobial agents include those mentioned herein as well as other antimicrobial agents known to one skilled in the art.
  • the second antimicrobial agent is hydrogen peroxide.
  • compositions of the invention can also include one or more of the additional agents.
  • additional agents include, but are not limited to, organic acids (such as dichloracetic acid for protein disruption), other peroxides (for protein disruption), alcohols (such as diacetone alcohol for membrane disruption), and ethers (such as butylene glycol monomethyl ether for membrane disruption).
  • Compositions of the invention have shown to be generally non-toxic and non-flammable. Compositions of the invention also evaporate relatively rapidly from a surface-of-interest leaving only an acceptable level of measurable residue.
  • compositions of the invention are used to disinfect a gram-positive bacteria, a gram-negative bacteria, a bacterial spore, or a combination thereof. Unlike other conventionally known antimicrobial agents that are commercially used, compositions of the invention have been shown to be effective in not only disinfecting gram-positive bacteria, but also in gram-negative bacteria, and bacterial spores. [0062] In many instances, compositions of the invention provide at least 6-log order complete kill or reduction of vegetative bacteria when applied to a surface. In other instances, compositions of the invention provide at least 5-log reduction of bacterial spores.
  • compositions of the invention provide a "complete kill" of the bacterial population atop the surface such that any functional bacteria remaining atop the surface-of-interest is/are not capable of re -populating to a measureable level, thereby rendering any toxicity or pathogenic functionality of the original bacterial population effectively null.
  • compositions of the invention can be applied in aerosol form such as spraying from a bottle containing liquid antimicrobial agent onto a surface. Once applied to the surface, the composition is adapted to evaporate to dryness (to the touch), typically within about 10 to about 30 minutes while leaving acceptable levels (if any) of measureable residue on the surface, such acceptable levels are generally set based on the surface on which the disinfectant is used.
  • Compositions of the invention are typically non-flammable and of very low toxicity allowing them to be shipped as a non-hazardous chemical, per DOT guidelines.
  • solutions comprising the compositions of the invention often have low surface tension and are effective in the presence of proteins.
  • compositions of the invention can be used to disinfect clean rooms, hospitals, veterinary and dental offices, laboratories (e.g., general medical/veterinary/dental, Q.A.
  • compositions of the invention include, but are not limited to, effectiveness at high dilutions in the presence of organic matter; a broad spectrum of antimicrobial activity-effectiveness against gram-positive, gram-negative bacteria, spores, viruses, and fungi); stable under the conditions of transport, storage and use; homogeneity; solubility in water, fats, and oils for good penetration into microorganisms; low surface tension for penetration into cracks and crevices; minimum toxicity-lack of acute and chronic toxicity, mutagenicity, carcinogenicity, etc.; capable of being applied with no residue after a desired period of time has passed; pleasant or minimal odor; non-flammable; low or no impact to plants and animals; and low cost.
  • antimicrobial compositions of the present invention as well as combinations of such products. Indeed, the combined and systematic use of products containing the antimicrobial compositions of the invention serves to eradicate microorganisms for a longer period of time and prevent their spread.
  • Some embodiments of the invention provide personal care products
  • Suitable personal care products comprising the antimicrobial composition disclosed herein include, but are not limited to, hand soaps, hand sanitizers, body washes, mouth washes, toothpastes, shower gels, shampoos, body lotions, deodorants, nasal sprays, foot care, vaginal care and/or wash, pet care and combinations thereof.
  • the personal care products disclosed herein take the form of a wipe product, particularly suitable for wiping or drying the face or hands.
  • the antimicrobial compositions of the invention are typically embedded or impregnated into the wipe product.
  • the personal care product disclosed herein takes the form of a tissue or towel, also suitable for wiping or drying the face or hands.
  • the personal care product takes the form of a feminine napkin and/or a diaper.
  • the personal care product takes the form of a first aid antiseptic for irritated, injured, or acne-affected skin and/or for pre or post surgical use.
  • antimicrobial compositions disclosed herein that are incorporated into one or more household care products.
  • suitable household care products for purposes of the invention include, but are not limited to, hard surface cleaners, deodorizers, fabric care compositions, fabric cleaning compositions, manual dish detergents, automatic dish detergents, floor care compositions, kitchen cleaners or disinfectants, bathroom cleaners or disinfectants and combinations thereof.
  • the household care product takes the form of a wipe or towel, suitable for household cleaning and/or care.
  • the household care products can comprise certain adjunct ingredients.
  • Exemplary adjuncts include, but are not limited to, detersive enzymes, builders, bleaching agents, bleach activators, transitional metal bleach catalysts, oxygen transfer agents and precursors, soil release agents, clay soil removal and/or anti-redeposition agents, polymeric dispersing agents, brightener, polymeric dye transfer inhibiting agents, chelating agents, anti-foam agents, alkoxylated polycarboxylates, fabric softeners, perfumes, carriers, hydrotropes, processing aids, dyes or pigments, solvents for liquid formulations, solid fillers, detersive surfactants and combinations thereof.
  • the antimicrobial compositions disclosed herein can be incorporated into a skin care product.
  • the skin care product incorporates a dermatologically acceptable carrier to facilitate safe transfer of the antimicrobial composition disclosed herein to the desired area of the skin.
  • the skin care product can include certain adjunct ingredients.
  • Suitable adjuncts include, but are not limited to, other antimicrobial and antifungal actives, surfactants, desquamation actives, anti-acne actives, anti-wrinkle actives, anti-atrophy actives, anti-oxidants, radical scavengers, chelators, flavonoids, anti-inflammatory agents, anti- cellulite agents, topical anesthetics, tanning actives, sunscreen actives, conditioning agents, thickening agents, detackifying agents, odor control agents, skin sensates, antiperspirants and mixtures thereof.
  • Other suitable adjunct ingredients are well known to one skilled in the art. See, for example, U.S. Pat. No. 6,294,186, which is incorporated herein by reference in its entirety.
  • This example illustrates one method of testing the antimicrobial effects of compounds of the invention.
  • a tube of the sample-disinfectant is placed into a waterbath for temperature control and allowed to equilibrate; (2) Once the tube has reached temperature, it is inoculated to achieve a concentration of approximately 10 6 CFU/mL; (3) At selected time points (generally five points are used including zero) aliquots are removed and placed into a neutralizer blank; (4) Dilutions of the neutralizer are made and selected dilutions plated onto agar; (5) Colonies are enumerated and log reductions are calculated.
  • CFU/mL CFU/mL was used. Most non-fastidious organism suspensions can be retained in the cooler for several days, and were used as long as enumeration demonstrated satisfactory viability.
  • Glass cover slips e.g., 25 mm 2
  • Sterile slides were used for this procedure. Slides were sterilized by placing them in layers separated by filter paper (e.g., Whatman #1) and placing them in an aluminum envelope then baking at 150-170 °C for 1-2 hours.
  • filter paper e.g., Whatman #1
  • the microorganism film was prepared by dispensing 20 ⁇ ⁇ of suspension onto a sterile slide and spreading the suspension drop over the surface of the slide.
  • a sterile inoculating needle that has been bent in the shape of a hockey stick was used.
  • the slide were placed on the pins of a sterile disposable plastic 96 well inoculating head that had small drops of sterile water placed onto some of the pins to help hold the slide in place during preparation.
  • the suspension was spread as near to the edges of the slide as possible without touching the edge. The drop was respread once more when necessary without over spreading.
  • the suspension was allowed to dry uncovered at room temperature. Inoculated slides were used as soon as possible, often the same day to minimize loss of viability.
  • Travel time for a treatment pass was about 1 ft/sec. Methods were adjusted in order to maintain consistent application between slides. Slides were air dried uncovered at room temperature.
  • the slide was placed into a 50 mL centrifuge tube containing 20 mL of LB. The tube was vigorously shaken for 5 seconds and then vortexed for 5 seconds. Mixing step was repeated once.
  • the LB was diluted in peptone, and was plated on an appropriate agar to attain countable dilutions. The LB tube (for decreased limit of quantitation) and agar plates were incubated overnight at the appropriate atmosphere and temperature.
  • the CFU/slide was calculated using the spiral plater counting tables and multiplying by the dilution factor. Viability loss due to disinfection was determined by comparing treated slide values with the untreated positive control.
  • TABEL Log Reduction of Bacillus cereus spores.
  • Peroxy pyruvic acid was synthesized as follows. Pyruvic acid was added to hydrogen peroxide at a temperature of between -30 °C and 10 °C until a conglomerate layer formed on the bottom of the flask. The reaction was allowed to stand without stirring until all pyruvic acid had dissolved into solution. Formation of peroxy pyruvic acid was confirmed by mass spectrometer and by chemical reaction.
  • Figure 1 shows efficacy of peroxy pyruvic acid against C. Difficile using sulfuric acid catalysts and methods of Example 1 above. All efficacy studies for C difficile were done according to the Official Method 966.04 "Sporicidal Activity of Disinfectants"
  • Figure 2 shows efficacy of peroxy alpha keto butyric acid against C. Difficile.
  • Ketobutyric Acid some modifications were needed due to the physical nature of the material.
  • Alpha-Ketobutyric Acid is a hygroscopic solid that melts at 30-34 °C. Thus, it is often present as a mixture of liquid and solid. The liquid was added first and this initiated the reaction after approximately 10% of the total weight had been added. This was a marked departure from the preparation of peroxypyruvic acid, in which the reaction initiates almost immediatealy with the first addition of the pyruvic acid.
  • PPA Pyruvic peracid
  • POKBA Peroxy a-ketobutyric acid
  • This test method is a standard test promulgated by ASTM Committee E35 on Pesticides and Subcommittee E35.15 on Antimicrobial Agents.
  • the stringency in the test is provided by the use of a soil load, the microtopography of the carrier surface and the small ratio of disinfectant to surface area (1 :5) typical for many disinfectant applications.
  • the metal disks used in the basic test are also compatible with a wide variety of germicidal actives and most surfaces in consumer based product manufacturing and health care facilities.
  • the design of the metal discs makes it possible to place onto each precisely measured volume of the test organism (28 ⁇ ) as well as the test formulation (125 ⁇ ),
  • the inoculum is placed at the center of each disk whereas the volume of the test formulation covers nearly the entire di sk surface thus eliminating the risk of any organisms remaining unexposed to the test formulation.
  • the relatively small ratio of 1:5 between the volume of the inoculum and that of the test formulation closely reflects many field applications of liquid chemical germicides.
  • the addition of 9.95 mL of a diluent gives a 1:200 dilution of the test formulation immediately at the end of the contact time. While this step in itself may be sufficient to arrest the germicidal activity of most formulations, a Letheen Broth (LB) was used as a specific neutralize!- and diluent.
  • the soil load used in this test was a mixture of three types of proteins (high molecular weight proteins, low molecular weight peptides and mucous material) and consisted of a mixture of 0.5 g of tryptone, 0.5 g of BSA, and 0.04 g of bovine mucin in 10 mL phosphate buffer (pH 7.2). These solutions were prepared separately and sterilized by passage through a 0.22 ⁇ pore diameter membrane filter, aliquoted and stored at either 4 °C or -20 °C.
  • Stainless Steel Disks (1 cm in Diameter and Approx. 0.7 mm Thick) were prepared from sheets of magnetized and brushed stainless steel 10 similar to that used in the manufacture of countertops. The disks were soaked in a detergent solution for at least one hour to degrease them and then washed and sterilized by autoclaving.
  • C. difficile was prepared by suspending a C. difficile suspension overnight into pre-reduced Brain heart infusion broth (BHI) and allowed to grow overnight. Inoculates from the BHI were streaked onto the surface of a sufficient number of pre-reduced trypticase soy agar plates with 5% sheep blood (BA) for confluent growth using a swab wetted in the prepared suspension (i.e., containing 1 mL of spore suspension). The BA plates were incubated for 14-28 days anaerobically.
  • BHI Brain heart infusion broth
  • BA sheep blood
  • the cells were harvested from the agar by adding 3 mL of sterile distilled water to the surface of the BA plate and suspended using a bent glass rod to suspended the cells from the plate into the water. A combined rinsing of each plate was added into one or more 50 mL centrifuge tube(s). The cells were centrifuged at 4500 rcf for 15 minutes and the supernatant carefully discarded. These steps were repeated two additional times. The final 10 mL of spore suspension was heated in a 65-70 °C water bath (assuring the entire tube is immersed) for 30 minutes.
  • the final concentration of spores in the suspension were checked for the purity of the spores by preparing a 1 : 1000 dilution in anaerobic broth and spiral plating 50 ⁇ ⁇ onto reduced BA plates.
  • the spores were stored at 2-8 °C until needed.
  • AKPA alpha Keto peroxy acids
  • Example 10 [0098] Various carboxylic acids and peroxy a-keto carboxylic acids were tested against various microorganisms. The results are shown in Figure 4. A series of methods were used for testing the microbes and are defined by the column titles on the Table in Figure 4. The details of these methods are as follows:
  • Suspensions were prepared in sterile skim milk medium (SM) by harvesting the organism from the agar plate using a sterile cotton swab and vigorously vortex mixing to achieve homogeneity. A viable concentration of 10 8 -109 CFU/mL is typically used. Most non-fastidious organism suspensions can be retained in the cooler for several days, and used as long as enumeration demonstrates satisfactory viability. Spore suspensions can be used directly or diluted to achieve the desired concentration of organism.
  • SM sterile skim milk medium
  • Sterile glass cover slips e.g., 25mm 2
  • Slides were Sterilized by placing them in layers separated by filter paper (e.g., Whatman #1) and then in an aluminum envelope and baking them at 150-170 °C for 1-2 hours.
  • the organism film on the slide was prepared by dispensing 20 ⁇ ⁇ of suspension onto a sterile slide and spreading the suspension drop over the surface of the slide. With a sterile inoculating needle that has been bent in the shape of a hockey stick.
  • Disinfectants were applied to inoculated glass coverslips with an air brush
  • Organisms were prepared on slides as indicated above.
  • the carrier slides with the organisms were placed in 20+2 mL of disinfectant and allow to soak for the desired amount of time. After 10 minutes, the carrier slides were placed into LB broth and enumerate discussed below.
  • This test is applicable to testing germicides for presence or absence of sporicidal activity against specified spore forming bacteria in various situations and potential efficacy as sterilizing agent.
  • the organism typically used for testing disinfectants for use against bacteria and bacterial spores with medical devices such as endoscopes, catheters, and etc. is B.
  • Subtilis spores because they are known to form biofilms which are difficult to eradicate. This is done by testing the disinfectants for sporicidal kill of the spores which are attached to ceramic penny cylinders.
  • the B. Subtilis spores were formed by inoculating nutrient agar (NA) slants and then washing growth on the slants with 10 mL of sterile deionized water and transferring to Roux bottles containing antibiotic medium #2 (AM#2) with MnS0 4 .
  • NA nutrient agar
  • A#2 antibiotic medium #2
  • the bottles were placed in a water bath at 65-70 °C water bath for 30 min. Afterwards the spore suspension was centrifuged at ⁇ 4500 rpm for 15 min. The supernatant was decanted and the spores resuspended with ⁇ 20 mL of sterile water.

Landscapes

  • Life Sciences & Earth Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical & Material Sciences (AREA)
  • Dentistry (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Plant Pathology (AREA)
  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Pest Control & Pesticides (AREA)
  • Agronomy & Crop Science (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)

Abstract

La présente invention porte sur des α-cétoalkylperacides et sur leurs procédés de production et d'utilisation. En particulier, les α-cétoalkylperacides sont utiles comme agents antimicrobiens.
PCT/US2010/031245 2010-04-15 2010-04-15 Α-cétoalkylperacides et leurs procédés de production et d'utilisation WO2011129829A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
PCT/US2010/031245 WO2011129829A1 (fr) 2010-04-15 2010-04-15 Α-cétoalkylperacides et leurs procédés de production et d'utilisation

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
PCT/US2010/031245 WO2011129829A1 (fr) 2010-04-15 2010-04-15 Α-cétoalkylperacides et leurs procédés de production et d'utilisation

Publications (1)

Publication Number Publication Date
WO2011129829A1 true WO2011129829A1 (fr) 2011-10-20

Family

ID=44798937

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/US2010/031245 WO2011129829A1 (fr) 2010-04-15 2010-04-15 Α-cétoalkylperacides et leurs procédés de production et d'utilisation

Country Status (1)

Country Link
WO (1) WO2011129829A1 (fr)

Cited By (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US8426634B2 (en) 2008-11-20 2013-04-23 Chd Bioscience, Inc. α-keto peracids and methods for producing and using the same
US8445717B2 (en) 2008-11-20 2013-05-21 Chd Bioscience, Inc. α-Keto alkylperacids and methods for producing and using the same
JP2014513056A (ja) * 2011-02-17 2014-05-29 シーエイチディー・バイオサイエンス，インコーポレーテッド ペルオキシα−ケトカルボン酸を含む組成物、および該組成物を産生し、そして用いるための方法
US9044527B2 (en) 2011-02-17 2015-06-02 Chd Bioscience, Inc. Wound care products with peracid compositions
US9283202B2 (en) 2012-10-18 2016-03-15 Chd Bioscience, Inc. Stable peracid-containing compositions
US9578879B1 (en) 2014-02-07 2017-02-28 Gojo Industries, Inc. Compositions and methods having improved efficacy against spores and other organisms
US11284621B2 (en) 2010-04-15 2022-03-29 Armis Biopharma, Inc. Compositions comprising peroxyacid and methods for producing and using the same
US11713436B2 (en) 2019-06-17 2023-08-01 Ecolab Usa Inc. Textile bleaching and disinfecting using the mixture of hydrophilic and hydrophobic peroxycarboxylic acid composition

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1991013058A1 (fr) * 1990-02-23 1991-09-05 Interox Chemicals Limited Solutions de peracides
WO1993001716A1 (fr) * 1991-07-23 1993-02-04 Ecolab Inc. Composition antimicrobienne a base d'acide peroxyde
US20040176267A1 (en) * 2003-01-06 2004-09-09 Hobson David W. Organic peroxyacid precursors

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1991013058A1 (fr) * 1990-02-23 1991-09-05 Interox Chemicals Limited Solutions de peracides
WO1993001716A1 (fr) * 1991-07-23 1993-02-04 Ecolab Inc. Composition antimicrobienne a base d'acide peroxyde
US5718910A (en) * 1991-07-23 1998-02-17 Ecolab Inc. Peroxyacid antimicrobial composition
US20040176267A1 (en) * 2003-01-06 2004-09-09 Hobson David W. Organic peroxyacid precursors

Cited By (16)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US8445717B2 (en) 2008-11-20 2013-05-21 Chd Bioscience, Inc. α-Keto alkylperacids and methods for producing and using the same
US9012681B2 (en) 2008-11-20 2015-04-21 Chd Bioscience, Inc. α-keto peracids and methods for producing and using the same
US9018412B2 (en) 2008-11-20 2015-04-28 Chd Bioscience, Inc. α-keto alkylperacids and methods for producing and using the same
US9468622B2 (en) 2008-11-20 2016-10-18 Chd Bioscience, Inc. α-keto peracids and methods for producing and using the same
US8426634B2 (en) 2008-11-20 2013-04-23 Chd Bioscience, Inc. α-keto peracids and methods for producing and using the same
US9844219B2 (en) 2008-11-20 2017-12-19 Chd Bioscience, Inc. Alpha-keto peracids and methods for producing and using the same
US11284621B2 (en) 2010-04-15 2022-03-29 Armis Biopharma, Inc. Compositions comprising peroxyacid and methods for producing and using the same
JP2014513056A (ja) * 2011-02-17 2014-05-29 シーエイチディー・バイオサイエンス，インコーポレーテッド ペルオキシα−ケトカルボン酸を含む組成物、および該組成物を産生し、そして用いるための方法
US9044527B2 (en) 2011-02-17 2015-06-02 Chd Bioscience, Inc. Wound care products with peracid compositions
US9283202B2 (en) 2012-10-18 2016-03-15 Chd Bioscience, Inc. Stable peracid-containing compositions
EP2908636A4 (fr) * 2012-10-18 2017-05-31 CHD Bioscience, Inc. Compositions comprenant du peroxyacide
US9877483B2 (en) 2012-10-18 2018-01-30 Armis Biopharma, Inc. Compositions comprising peroxyacid and methods for producing and using the same
US9578879B1 (en) 2014-02-07 2017-02-28 Gojo Industries, Inc. Compositions and methods having improved efficacy against spores and other organisms
US10405545B2 (en) 2014-02-07 2019-09-10 Gojo Industries, Inc. Compositions and methods having improved efficacy against spores and other organisms
US9936695B1 (en) 2014-02-07 2018-04-10 Gojo Industries, Inc. Compositions and methods having improved efficacy against spores and other organisms
US11713436B2 (en) 2019-06-17 2023-08-01 Ecolab Usa Inc. Textile bleaching and disinfecting using the mixture of hydrophilic and hydrophobic peroxycarboxylic acid composition

Similar Documents

Publication Publication Date Title
US9844219B2 (en) Alpha-keto peracids and methods for producing and using the same
US9018412B2 (en) α-keto alkylperacids and methods for producing and using the same
US11839213B2 (en) Antimicrobial, disinfecting, and wound healing compositions and methods for producing and using the same
WO2011129829A1 (fr) Α-cétoalkylperacides et leurs procédés de production et d'utilisation
US20090035339A1 (en) Methods of Inactivating Viruses
US20230404962A1 (en) Antimicrobial, disinfecting and wound healing compositions and methods for producing and using same
WO2005014057A1 (fr) Compositions desinfectantes et leurs procedes de fabrication et d'utilisation
CA2107996A1 (fr) Alcool perillique biocide qui agit contre les bacteries et les levures
WO2021142148A1 (fr) Compositions antimicrobiennes à l'état solide et leurs procédés de production et d'utilisation
US20130079408A1 (en) Peracid and 2-hydroxy organic acid compositions and methods for treating items
KR20060009259A (ko) 살생제, 멸균제, 방부제, 소독제 및 구충제로서의디알킬케톤 퍼옥사이드의 용도
KR100384538B1 (ko) 젖병, 젖꼭지와 같은 유아용품을 살균, 세정하기 위한조성물
RU2796846C1 (ru) Антисептическое и дезинфицирующее средство
US20230030675A1 (en) Solid state antimicrobial compositions and methods for producing and using same
EP4154895A2 (fr) Composition biologiques naturelles antibactériennes et antivirales, composés, procédé d'obtention et leur utilisation
RU2736364C2 (ru) Дезинфицирующая композиция с винной кислотой, молочной кислотой
CN112471161A (zh) 一种多功能聚合性消毒液
Plantation-West STERILIZATION, DISINFECTION, ECOLOGY AND PREPARATION OF PEDAL SKIN

Legal Events

Date Code Title Description
121 Ep: the epo has been informed by wipo that ep was designated in this application

Ref document number: 10849971

Country of ref document: EP

Kind code of ref document: A1

NENP Non-entry into the national phase

Ref country code: DE

122 Ep: pct application non-entry in european phase

Ref document number: 10849971

Country of ref document: EP

Kind code of ref document: A1