WO2004000016A2 - Antimicrobial compositions, products and methods employing same - Google Patents
Antimicrobial compositions, products and methods employing same Download PDFInfo
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- WO2004000016A2 WO2004000016A2 PCT/US2003/019718 US0319718W WO2004000016A2 WO 2004000016 A2 WO2004000016 A2 WO 2004000016A2 US 0319718 W US0319718 W US 0319718W WO 2004000016 A2 WO2004000016 A2 WO 2004000016A2
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q17/00—Barrier preparations; Preparations brought into direct contact with the skin for affording protection against external influences, e.g. sunlight, X-rays or other harmful rays, corrosive materials, bacteria or insect stings
- A61Q17/005—Antimicrobial preparations
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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
- A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
- A01N25/30—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests characterised by the surfactants
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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
- 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
- A01N37/04—Saturated carboxylic acids or thio analogues thereof; Derivatives thereof polybasic
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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
- 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
- A01N37/36—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 at least one carboxylic group or a thio analogue, or a derivative thereof, and a singly bound oxygen or sulfur atom attached to the same carbon skeleton, this oxygen or sulfur atom not being a member of a carboxylic group or of a thio analogue, or of a derivative thereof, e.g. hydroxy-carboxylic acids
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/185—Acids; Anhydrides, halides or salts thereof, e.g. sulfur acids, imidic, hydrazonic or hydroximic acids
- A61K31/19—Carboxylic acids, e.g. valproic acid
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
- A61K31/365—Lactones
- A61K31/375—Ascorbic acid, i.e. vitamin C; Salts thereof
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/70—Carbohydrates; Sugars; Derivatives thereof
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/02—Cosmetics or similar toiletry preparations characterised by special physical form
- A61K8/0208—Tissues; Wipes; Patches
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q19/00—Preparations for care of the skin
- A61Q19/10—Washing or bathing preparations
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02A—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE
- Y02A50/00—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE in human health protection, e.g. against extreme weather
- Y02A50/30—Against vector-borne diseases, e.g. mosquito-borne, fly-borne, tick-borne or waterborne diseases whose impact is exacerbated by climate change
Definitions
- the present invention relates to antimicrobial compositions, products incorporating said antimicrobial compositions and methods of using the present antimicrobial compositions and products. More specifically, the present invention relates to antimicrobial compositions comprising an organic acid or organic acid mixture, a specific, short-chain anionic surfactant having at least one of the following: a large, hydrophilic head group; an unsaturated structure; and/or a branched structure.
- Bacteria found on human skin may be 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 aure s, Streptococcus pyogenes and Clostridi m botulinum.
- Gram-negative bacteria include pathogens such as Salmonella, Escherichia coli, Klebsiella, Haemophilus, Pseudomonas aeuginosa, Proteus and Shigella dysenteriae.
- Gram- negative bacteria are generally distinguished from Gram-positive bacteria via the existence of an additional protective cell membrane in the former, which often results in Gram-negative bacteria being less susceptible to conventional, topical antibacterial actives.
- antimicrobial cleansing products include deodorant soaps, hard surface cleaners, and surgical disinfectants. These traditional, rinse-off antimicrobial products have been formulated to provide bacteria removal during washing. A few such products, including antimicrobial soaps, have also been shown to provide a residual effectiveness against Gram-positive bacteria, but provide 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.
- 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.
- those skilled in the art have sought to incorporate high levels of alcohol and/or harsh surfactants into contemporary antimicrobial products, which have been shown to cause dryness and irritation to skin tissues.
- the present invention addresses and resolves all of the problems associated with the employment of conventional antimicrobial compositions and/or products, indeed, it has been surprisingly discovered that a composition incorporating an organic acid or organic acid mixture, a specific short-chain anionic surfactant having at least one of a large, hydrophilic head group; an unsaturated structure; and/or a branched structure; constitutes a viable advancement and alternative in the realm of antimicrobial formulations.
- the antimicrobial compositions of the present invention are adapted for direct application to human skin, without causing dryness or irritation.
- the antimicrobial compositions of the present invention are designed for use with or without water, and provide immediate and residual effectiveness in either instance against a variety of viruses and bacteria, including rotavirus, rhinovirus, respiratory syricytial virus (RSV), coronavirus, Gram-positive and Gram-negative bacteria.
- viruses and bacteria including rotavirus, rhinovirus, respiratory syricytial virus (RSV), coronavirus, Gram-positive and Gram-negative bacteria.
- anionic surfactant of the present invention presents a particularly novel aspect of the present compositions.
- Those of skill in the art have generally relied upon the incorporation of longer chain (i.e. C ⁇ 2 to C ⁇ 6 ) anionic surfactants into antimicrobial compositions.
- Conventional surfactants comparable to the acyl components found in the phospholipid matrix of the cell membrane of bacteria and virus, are thought to possess optimum antimicrobial activity with reduced skin tissue penetration.
- conventional anionic surfactants have been associated with low solubility under acidic conditions, poor compatibility with cationic antimicrobial agents, slow dissolution kinetics and limited residual antimicrobial performance.
- the short chain anionic surfactants of the present invention comprise at least one of the following characteristics: a large, hydrophilic head group; an unsaturated structure; and/or a branched structure.
- the surfactants of the present invention have traditionally been regarded as unsuitable for incorporation into an antimicrobial composition, based on the belief that such surfactants possess relatively low surface activity.
- the surfactants of the present invention deliver enhanced antimicrobial efficacy against rotavirus, rhinovirus, respiratory syricytial virus (RSV), coronavirus, Gram-negative bacteria and Gram-positive bacteria.
- RSV respiratory syricytial virus
- the large head group, unsaturated structure and/or branched structure of the present surfactants reduces or limits their tendency to penetrate skin tissue, while maximizing the immediate and residual effectiveness of the antimicrobial compositions in which they are incorporated.
- the anionic surfactants of the present invention exhibit stability in an aqueous product at a low pH, are compatible with cationic antimicrobial agents and convey strong residual antimicrobial activity when the substrate on which they are applied is later inoculated with virus or bacteria.
- antimicrobial compositions comprising an organic acid or organic acid mixture, a specific, short-chain anionic surfactant mixture are disclosed.
- suitable anionic surfactants for use in the context of the present invention comprise a chain length of from about C 4 to C12 and at least one of the following characteristics: a large, hydrophilic head group; an unsaturated structure; and/or a branched structure.
- the antimicrobial compositions disclosed herein optionally further comprise a calcium ion scavenger and/or an anti-foam agent.
- the compositions of the present invention are adapted to provide immediate and residual kill of numerous bacteria and viruses, with or without the use of water and without causing dryness or irritation to skin.
- products incorporating the antimicrobial compositions of the present invention are disclosed. Such products may take an assortment of shapes and forms depending on the precise application for which deployment of the product is desired and the needs and/or abilities of the formulator. In any instance, the products of the present invention are effective in eradicating numerous bacteria and viruses, both immediately and residually and are adapted to prevent dryness and/or irritation to mammalian skin tissue.
- methods of using the antimicrobial compositions and products of the present invention are disclosed. The methods of the present invention are adapted to achieve immediate and/or residual kill of a variety of viruses and bacteria, without irritating the skin and with or without the use of water.
- antimicrobial compositions adapted for immediate and residual efficacy against a variety of bacteria and viruses.
- the compositions of the present invention comprise an organic acid or organic acid mixture; an anionic surfactant having a chain length of from about C to about C 12 and at least one of the following characteristics: an unsaturated structure, a branched structure; and/or a hydrophilic head group having a total head group size (defined, infra) of between about 4 to about 15 Angstroms.
- the antimicrobial compositions disclosed herein optionally further comprise a calcium ion scavenger and/or anti-foam agent.
- the compositions of the present invention are characterized by a pH of between about 2.0 to about 4.5, depending on the specific constituents of the present antimicrobial compositions and the application for which their use is intended.
- the antimicrobial compositions disclosed herein comprise an amount of an organic acid or organic acid mixture.
- Organic acids for purposes of the present disclosure, are defined as proton-donating agents that remain at least partially undisassociated in a concentrated composition and remain so when the compositions are diluted during washing and rinsing.
- the organic acids of the present invention serve to protonate the carboxylate functionalities on the phospholipid membrane of bacteria and virus and reduce the tendency of the membrane to electronically repel anionic surfactants, thereby facilitating proper interaction between the present, anionic surfactants and the membrane.
- the organic acids disclosed herein facilitate the creation of a low pH buffer on the surface of a substrate, thereby prolonging the residual antimicrobial activity of the compositions and products in which they are incorporated.
- the present organic acids are added directly to the compositions of the present invention in acidic form or are formed by adding the conjugate base of the desired acid and an amount of a separate acid sufficient to form the undissociated acid from the base.
- the antimicrobial compositions of the present invention comprise from about 0.2% to about 70%, preferably about 0.5% to about 40%, more preferably from about 1.0% to about 30%, based on the total weight of the antimicrobial composition, of an organic acid or organic acid mixture.
- Suitable organic acids of the present invention include, but certainly are not limited to: pyroglutamic acid, adipic acid, gluconic acid, glyconolactone acid, glutamic acid, glycolic acid, glutaric acid, tartaric acid, ascorbic acid, benzoic acid, salicylic acid, citric acid, malic acid, succinic acid, lactic acid, carboxymethylcellulose and mixtures thereof.
- suitable organic acids for incorporation into the present compositions are characterized by a pKa of greater than about 3.0.
- the pKa selection limitation of the present organic acids serves the fundamental goal of ensuring that at least 50% of the organic acids incorporated into the present compositions remain undissociated at the desired pH of from about 2.0 to about 4.5 (discussed, infra).
- the compositions disclosed herein comprise a calcium ion scavenger.
- the calcium ion scavengers of the present invention facilitate the disruption of the cell membrane of bacteria and viruses by the present, anionic surfactants via capture of the calcium ions of the phospholipid cell membrane.
- said calcium ions are believed to exist within and around the cell membrane, thereby often preventing the penetration of conventional surfactants.
- the present, calcium ion scavengers are a particularly preferred ingredient of the present antimicrobial compositions when the targeted microbial is rotavirus.
- Suitable calcium ion scavengers of the present invention include, but are not limited to: citric acid, malic acid, succinic acid, polyacrylic acid, copolymers of acrylic acid and maleic acid, oxydisuccinic acid, nitrilotriacetic acid, iminodisuccinic acid, tartrate disuccinic acid, tartrate monosuccinic acid, ethylenediaminetetraacetic acid, pyrophosphoric acid and mixtures thereof.
- the calcium ion scavengers of the present invention are characterized by a pKa of lower than about 3.0.
- suitable calcium ion scavengers are characterized by a calcium ion binding constant (log P) of greater than about 3.0 at a pH of about 3.
- anionic surfactants of the present invention constitute a particularly novel and unobvious aspect of the present invention. Indeed, it has been surprisingly discovered that, contrary to the conventional wisdom in the art, anionic surfactants having a chain length of from about C 4 to about C 12 and at least one characteristic selected from: a large hydrophilic head group; an unsaturated structure; and/or a branched structure; provide enhanced performance benefits, while minimizing dryness and/or irritation to mammalian skin tissue.
- the short chain anionic surfactants of the present invention exhibit phase stability in formulation, compatibility with other antimicrobial agents and residual efficacy of the antimicrobial compositions in which they are incorporated.
- the antimicrobial compositions of the present invention comprise from about 0.1% to about 40%, preferably from about 0.2% to about 30%, more preferably from about 0.3% to about 20% of an anionic surfactant mixture.
- the short-chain anionic surfactants disclosed herein are incorporated into the present, antimicrobial compositions at a level of greater than about 25%.
- the anionic surfactants useful for incorporation into the present antimicrobial compositions comprise a relatively short carbon chain, preferably between about C to about C ⁇ 2 , more preferably between about C 6 to about Cn, most preferably between about C 6 to about o.
- the average chain length of the resultant anionic surfactant mixture may differ from the above-described ranges.
- short-chain anionic surfactants are characterized by decreased interfacial activity and decreased interaction with the phospholipid membrane of bacteria and virus, and thus, provide poor microbiocidal activity. Accordingly, those of skill in the art have generally relied upon the employment of anionic surfactants with chain lengths of from 2 to C ⁇ 6 in antimicrobial compositions. The chain lengths of such surfactants are comparable to those of the acyl components in the phospholipid membrane of bacteria and virus, and thus, are thought to provide optimum microbiocidal activity.
- longer chain surfactants have conventionally been thought to be less capable of skin penetration, and thus, less likely to cause dryness and irritation to skin. Nevertheless, conventional, longer chain anionic surfactants often exhibit poor phase stability in an acidic product matrix, incompatibility with cationic antimicrobial agents and decreased residual antimicrobial activity. Conversely, the shorter chain anionic surfactants of the present invention exhibit surprisingly high immediate microbiocidal activity, phase stability in broad concentration ranges of acidic aqueous matrices and compatibility with cationic antimicrobial agents. Importantly, the anionic surfactants of the present invention prevent dryness or irritation to skin and demonstrate strong residual microcidial activity on a target substrate when the substrate is later inoculated with bacteria or virus.
- the short chain anionic surfactants disclosed herein possess an unsaturated structure and/or a branched, hydrophobic group with a total carbon content ranging from about C 4 to about C u , preferably from about C 6 to about Cn and more preferably from about C 6 to C 10 .
- the short-chain anionic surfactants disclosed herein comprise a hydrophilic head group with a total head group size of less than about 15 Angstroms, preferably less than about 10 Angstroms, more preferably between about 4 to about 7 Angstroms.
- total head group size it is meant the accumulated size of every substituent on the hydrophilic head group of the present anionic surfactants.
- the present anionic surfactants may comprise more than one substituent on their subject hydrophilic head groups, for a combined, total hydrophilic head group size falling within the above-listed, ranges.
- the unsaturated structure and/or branched structure and/or large hydrophilic head group of the present, anionic surfactants increases their water solubility, increases their compatibility with cationic agents, increases steric hindrance to their disruption of the stratum conium layer of skin and maintains their substantivity to the phospholipid membrane of bacteria and viruses.
- the "hydrophilic head group” is defined as the hydrophilic portion (which may contain both non-hydrocarbon and hydrocarbon units) of the anionic surfactant, measured from the first polar atom to the end of the hydrophilic segment that links to the hydrophobic body.
- the hydrophilic head group of alkyl glyceryl sulfonate R-O-CH 2 CH(OH)CH 2 -SO 3 Na is - O-CH 2 CH(OH)CH 2 -SO 3 Na.
- the hydrophilic head group size is estimated from the Van der Waals radius of the atoms and the configuration of the surfactant molecule.
- Suitable hydrophilic head groups of the present invention with a size of less than about 10 Angstroms include, but are not limited to: glyceryl ether sulfonates and, for compositions having a pH of greater than 3.5, isethionates, sulfosuccinates, amidosulfonates and ethoxylated sulfonates. .
- the head group of the anionic surfactant is characterized by substitution of one or more substituents.
- substituents it is meant any hydrophilic segment that is bonded to the head group, defined hereinbefore, of the present anionic surfactants. Without wishing to be bound by theory, it is believed that such increased substitution on the head group of the present anionic surfactants further increases the size and hydrophilicity of the head group.
- Suitable hydrophilic head groups of the present invention with multiple substituents include, but are not limited to, alpha sulfo fatty acid, and if the pH of the present antimicrobial compositions is greater than 3.5, monoester of sulfosuccinic acid.
- head group size of the present anionic surfactants is defined on the basis of Angstroms, as discussed supra.
- the hydrophilic head group of the present anionic surfactants may comprise more than one substituent, the total hydrophilic head group size should not exceed the preferred size ranges, set forth hereinbefore, in Angstroms.
- suitable anionic surfactants of the present invention include, but certainly are not limited to: linear or branched alkyl glyceryl sulfonate, alkyl alpha sulfo fatty acid, alpha olefin sulfonate, branched alkyl sulfonate, branched alkyl benzene sulfonate, branched alkyl phosphonate and if the pH of the antimicrobial composition is greater than about 3.5, secondary alkyl sulfate, alkyl isethionate, monoester of alkyl sulfosuccinic acid, alkyl aminosulfonate, alkyl ethoxylated sulfonate, and combinations thereof.
- anionic surfactants having a chain length of from about C 4 to about 2 and comprising at least one of the following characteristics are suitable for use herein: an unsaturated structure; a branched structure and/or a hydrophilic head group size as described hereinbefore. Selection of the appropriate anionic surfactant for use in the antimicrobial compositions of the present invention will depend upon the needs and/or abilities of the formulator. In another aspect of the present invention, other surfactants, many commercially available, are incorporated into the antimicrobial compositions of the present invention.
- Said surfactants although depending on the precise form of the desired antimicrobial composition, include, but certainly are not limited to: paraffin sulfonate, hydrolyzed methyl ester sulfonate, alkyl sulfosuccinate, alkyl glyceryl sulfonate, alpha olefin sulfonate, alkyl isethionate, secondary alkyl sulfate, branched alkyl benzene sulfonate, alkyl sulfate and combinations thereof.
- anionic surfactant for use in the context of the antimicrobial compositions of the present invention will depend upon several factors, including, but certainly not limited to: the nature of the substrate for which use of the antimicrobial compositions disclosed herein is desired and the needs and/or abilities of the formulator and/or practitioner of the present compositions.
- short chain anionic surfactants having a hydrophilic head group size of less than about than 4 Angstroms and/or a linear structure may be suitable for use in the context of the present invention.
- suitable anionic surfactants for use in the context of the present invention include, but certainly are not limited to: sulfonates and sulfates having a linear chain with a chain length of from about C 4 to about C ⁇ 2 , preferably having a chain length of from about C 6 to about C ⁇ 2, more preferably having a chain length of from about C 8 to about C 12 .
- the antimicrobial compositions disclosed herein comprise an anti-foam or suds suppression agent. Incorporation of said agents is particularly desired for applications in which the present antimicrobial compositions comprise high sudsing, short chain anionic surfactants such as alkyl glyceryl sulfonate and/or a level of anionic surfactant of greater than about 1 weight percent, incorporation of an anti-foam agent or suds suppression system is further advantageous in compositions for which low foaming is desired, particularly when such foaming has the affect of decreasing the conveyance of antimicrobial dosage.
- the antimicrobial compositions disclosed herein comprise an anti-foam or suds suppression agent, present at a level of from about 0.0001% to about 15%, preferably from about 0.001% to about 10%, most preferably from about 0.005% to about 5% by weight of the antimicrobial composition.
- the anti-foam agent is present in an amount of at least 1 ppm by weight of the total composition.
- suitable suds suppressing systems for use herein may comprise essentially any known antifoam compound that exhibits stability at a pH of about 2.0 to about 4.5, including, but not limited to, those selected from the group consisting of: silicone antifoam compounds, silicone emulsions, 2-alkyl and alkanol antifoam compounds, mineral oil emulsions, hydrocarbon oil emulsions, polyalkylene emulsions and combinations thereof.
- Silicone suds suppressor technologies and other anti-foam agents useful herein are extensively documented in "Defoaming, Theory and Industrial Applications", Ed., P.R. Garrett, Marcel Dekker, N.Y., 1973, ISBN 0-8247-8770-6, incorporated herein by reference. See especially the chapter “Surfactant Antifoams” (Blease et al). See also U.S. Patents 3,933,672 and 4,136,045, both incorporated herein by reference.
- Highly preferred silicone suds suppressors are the compounded types known for use in antimicrobial compositions, including, for example, polydimethylsiloxanes having trimethylsilyl or alternate endblocking units.
- Such compounds may be compounded with silica and/or with surface-active nonsilicon components, as illustrated by a suds suppressor comprising 12% silicone/silica, 18% stearyl alcohol and 70% starch.
- a suitable, commercial source of the silicone active compounds is Dow Corning Corp.
- the antimicrobial compositions disclosed herein further comprise a nonionic agent.
- suitable nonionic agents for use in the present compositions are selected from the group consisting of: alkyl polyols, alkyl alcohols, phenols, chloro phenols, polyphenols and mixtures thereof.
- the optional nonionic agent of the present invention serves many roles, including, but certainly not limited to, increasing the antibacterial efficacy, in both immediate and residual kill, of the organic acid and short chain anionic surfactant system of the present invention.
- alkyl polyols such as l-(2- ethylhexyl)glycerol ether
- alkyl polyols and alkyl alcohols have the affect of increasing the immediate and residual activity of the present compositions.
- the nonionic agents of the present invention are incorporated into the present antimicrobial compositions in an amount of from about 0.1% to about 10%, preferably from about 0.1% to about 5%, more preferably from about 0.1% to about 3%, by weight of the total, antimicrobial composition.
- the antimicrobial compositions of the present invention comprise a nonionic agent
- said agent comprises a carbon chain length of from about C 3 to about C 12 .
- Suitable nonionic agents for incorporation into the antimicrobial compositions of the present invention include, but certainly are not limited to: l-(2-ethylhexyl) glycerol ether, octyl glycerol ether, 2-(2-ethylhexylxoxy) propanol, octyloxy propanol, l-(2-etbylhexyloxy) ethanol, octyloxy ethanol, 1,2 hexylenediol, 1,2-cyclohexanedimethanol, isopropyl glycerol ether, 4-chloro-3-xylenol and combinations thereof.
- the nonionic agent is branched, unsaturated or linear.
- the nonionic agent is substituted with compounds selected from the group consisting of: alcohols, polyols, phenols, chloro phenols, polyphenols and combinations thereof.
- compositions disclosed herein will comprise one or more adjunct ingredients.
- Said ingredients may be employed to increase the mildness of the desired composition, increase immediate and/or residual efficacy of the subject compositions, improve the wetting characteristics of the subject compositions upon application to a target substrate, operate as solvents for diluted compositions, and/or serve to modify the aesthetic characteristics of the composition,
- the compositions disclosed herein comprise from about 0% to about 70%, preferably from about 0% to about 62%, more preferably from about 0% to about 10%, of an alcohol solvent.
- Suitable alcohol solvents of the present invention include, but are not limited to, ethanol, propanol, butanol, probpylene glycol, diethylene glycol, dipropylene glycol and mixtures thereof.
- compositions disclosed herein comprise from about 0% to about 10%, preferably from about 0% to about 5%, more preferably from about 0% to about 1%, of a cationic antimicrobial agent.
- a cationic antimicrobial agent e.g., benzalkonium chloride, benzethonium chloride, triclocarban, tricolsan, chlorhexidine and mixtures thereof.
- the compositions disclosed herein comprise from about 0% to about 5%, preferably from about 0% to about 2%, of a heavy metal salt selected from the group consisting of: silver, zinc, copper and mixtures thereof. Incorporation of said heavy metal salt serves to increase the antimicrobial activity and the viscosity of the present, antimicrobial compositions. Moreover, the other ingredients of the present compositions have exhibited compatibility with the heavy metal salts disclosed herein.
- the compositions disclosed herein comprise from about 0% to about 20%, preferably from about 0% to about 5%, of a skin emollient or moisturizer. Such ingredients serve the fundamental purpose of increasing the mildness (discussed infra) of the present antimicrobial compositions and are particularly desired when incorporating the present antimicrobial compositions into a skin care product (discussed infra).
- one or more adjunct ingredients are incorporated into the antimicrobial compositions disclosed herein, to facilitate formulation of the desired composition.
- additional adjunct ingredients is often necessary to formulate certain ingredients included in the present compositions and in antimicrobial compositions generally. Indeed, it has been discovered, and documented via the present disclosure, that the formulation of certain perfumes and/or skin emollients in antimicrobial compositions requires the use of alkyl polyether-type emulsifiers. It has been learned that the use of said alkyl polyether-type emulsifiers is necessary to achieve physical stability of the resultant antimicrobial product when attempting to formulate certain perfumes and/or skin emollients.
- the antimicrobial compositions disclosed herein comprise from about 0.05% to about 5%, preferably from about 0.1% to about 1%, more preferably from about 0.2% to about 0.5% of an alkyl polyether-type emulsifier.
- alkyl polyether-type emulsifiers suitable for incorporation into the antimicrobial compositions disclosed herein include: isoceteth-20 (CAS No. 69364-63-2) and ceteth -20 (CAS No. 9004-95-9),.
- alkyl polyether-type emulsifiers disclosed herein are provided for use in the context of formulation of any antimicrobial composition comprising one or more otherwise physically instable adjunct ingredients, and not specifically limited to the antimicrobial compositions disclosed herein.
- said otherwise physically instable adjunct ingredients include, but certainly are not limited to: perfumes, skin emollients, other nonionic agents and mixtures thereof.
- other ingredients are included into the antimicrobial compositions to achieve physical stability for perfumes, skin emollients and other adjunct incorporated therein that otherwise exhibit physical instability absent the use of such adjuncts.
- the present invention further seeks to encompass the use of sulfonate anionic surfactant having a chain length of 2 to Cm are suitable for use in the context of the antimicrobial compositions disclosed herein, and are particularly preferred when the formulator of the present compositions seeks to incorporate certain adjuncts such as perfumes, skin emollients and combinations thereof.
- the antimicrobial compositions disclosed herein comprise from about 0 to about 5%, preferably from about 0.1% to about 2%, more preferably from about 0.2% to about 1%.
- Suitable sulfonate anionic surfactants for use in the context of the present invention include, but certainly are not limited to: C ⁇ 4 - ⁇ s paraffin sulfonate and C 14 - ⁇ 8 alkyl alpha olefin sulfonate. .
- the incorporation of sulfonate anionic surfactants is particularly preferred in the context of the present invention when the formulator of the present compositions seeks to include perfumes, skin emollients and combinations thereof.
- the pH of the antimicrobial compositions of the present invention must be adjusted to a sufficiently low level in order to either form or deposit substantially undissociated acids onto the substrate for which treatment is desired.
- substantially undissociated it is meant that, upon application of the present compositions onto a target substrate, such as mammalian skin, about 30%, preferably 50%, more preferably 70%, of the organic acids incorporated in said compositions remain undissociated following the elapse of about 30 minutes from application.
- the pH of the present compositions should be adjusted and preferably buffered to achieve the desired range.
- the antimicrobial compositions disclosed herein are characterized by a pH of from about 2.0 to about 4.5, preferably from about 2.5 to about 4.0.
- the pH of the antimicrobial compositions of the present invention will depend upon the precise ingredients incorporated into the subject compositions. Nevertheless, the pH of the present compositions is generally, and preferably, above about 2.0, as compositions characterized by a pH below 2.0 are typically required to be identified as toxic or hazardous materials. Mildness of Antimicrobial Compositions
- Topically applied products including rinse-off cleansers and leave-on sanitizers, have conventionally possessed the tendency to irritate or dry mammalian skin.
- the compositions of the present invention provide immediate and residual kill of bacteria and viruses, while possessing the fundamental characteristic of mildness.
- mildness it is meant the degree to which a composition prevents dryness or irritation to skin.
- Factors that influence the mildness of a topically applied antimicrobial product include, but are not limited to, duration of exposure to the product, the frequency of use of the product and the degree to which the skin is occluded following exposure to the product.
- Irritation is observed by several methods, including but not limited to, visual and instrumental assessment of the erythema for redness and of the skin for edema following application of an antimicrobial product. Irritation may be measured by determining the transepidermal water loss (TEWL) of skin before and after exposure to an antimicrobial product, using, for example, a TEWL meter. Indeed, products that cause irritation may eventually compromise the natural barrier function of mammalian skin - resulting in increased water loss through the epidermis. Dryness is observed by several methods including, but not limited to, visual and instrumental assessment of the level and severity of dry skin flakes following exposure to an antimicrobial product. Dryness may be measured by instruments that examine the water content of the skin. One such instrument, a corneometer, measures the water content of skin via capacitance.
- a corneometer measures the water content of skin via capacitance.
- the present invention despite its enormous cleaning and antimicrobial characteristics, is adapted to ensure increased mildness to mammalian skin upon application, particularly when compared to conventional cleansers such as bar or liquid soap and leave-on sanitizers.
- conventional cleansers such as bar or liquid soap and leave-on sanitizers.
- the efficacy and mildness of the compositions of the present invention has been examined and illustrated under a variety of use conditions and methods. Namely, during a 10-day clinical forearm study, subjects applying the compositions of the present invention experienced significantly less skin irritation and dryness than subjects engaging in the same number of washes per day with soap and water and subjects applying conventional alcohol-based hand sanitizers. The results of the aforementioned study were measured using both visual and instrumental methods.
- the present invention further relates to products that comprise the 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 present invention serves to eradicate viruses (e.g. rhinovirus, rotavirus, respiratory syricytial virus (RSV), coronavirus) and bacteria (e.g. Gram-positive and Gram-negative) for a longer period of time and prevent their spread.
- viruses e.g. rhinovirus, rotavirus, respiratory syricytial virus (RSV), coronavirus
- bacteria e.g. Gram-positive and Gram-negative
- Suitable personal care products comprising the antimicrobial compositions of the present invention 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 present invention are preferably embedded or impregnated into said 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.
- the antimicrobial compositions of the present invention are incorporated into one or more household care products.
- suitable household care products for purposes of the present 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 disclosed herein comprise certain adjunct ingredients.
- Said adjuncts include, but certainly 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 of the present invention are incorporated into a skin care product.
- the skin care product incorporates a dermatologically acceptable carrier to facilitate safe transfer of the antimicrobial composition of the present invention to the desired area of the skin.
- the skin care product of the present invention comprises certain adjunct ingredients.
- Said adjuncts include, but certainly are not limited to: 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.
- antimicrobial and antifungal actives include, but certainly are not limited to: 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
- articles of manufacture comprising the antimicrobial compositions of the present invention and/or one or more of the aforementioned products, are intended for personal care, skin care and household care applications.
- the article of manufacture of the present invention encompasses one or more products as described hereinbefore that may be packaged in a container or dispenser with a set of instructions for the consumer.
- the article of manufacture of the present invention typically comprises (a) container or dispenser, (b) product and (c) set of instructions to apply said product to an appropriate substrate to achieve immediate and residual antimicrobial activity.
- Containers and/or dispensers suitable for the article of manufacture of the present invention include, but are not limited to: PET bottles and tubs, flow-wrap pouches, foaming dispensers, spray dispensers and combinations thereof.
- the article of manufacture of the present invention further comprises a set of instructions in association with the container.
- association with it is meant that the instructions are either directly printed on the container or dispenser itself or presented in a different fashion including, but not limited to: a brochure, print advertisement, electronic advertisement and/or verbal communication, so as to communicate the set of the instructions to a consumer of the article of manufacture.
- the set of instructions typically comprise the instructions relating to the use of the product to apply the antimicrobial composition of the present invention onto a suitable substrate for which treatment is sought.
- the set of instructions may further comprise the instruction to allow the antimicrobial composition of the present invention to remain on the treated substrate, without rinsing or otherwise removing the antimicrobial composition from the treated substrate.
- the precise instructions included with the article of manufacture of the present invention will depend on the precise ingredients of the subject antimicrobial composition and the product for which the inclusion of instructions is desired and the substrate onto which application of the product is intended.
- the instructions included in the present articles of manufacture coincide with the methods set forth in the "Methods of Use" section of the present disclosure.
- the antimicrobial compositions and products of the present invention are suitable for a variety of uses. Indeed, suitable uses of the present compositions include, but certainly are not limited to, the eradication of viruses and or bacteria; the provision of residual anti-viral efficacy; the provision of residual antibacterial efficacy; the prevention and/or treatment of a common cold or associated respiratory disease in a mammal; the prevention and/or treatment of a diarrhea disease in a mammal; the prevention and/or treatment of bacteria-related diseases in mammals resulting from contact with a bacteria-infected surface; the sanitization of hard surfaces; the improvement of the overall health of a mammal; the reduction of absenteeism; the prevention and/or treatment of dandruff and acne; and combinations thereof.
- treatment with the compositions and products disclosed herein is effective when the cold or respiratory disease is caused by rhinovirus, coronavirus or RSV. It should be noted that, in the case of diarrhea, treatment with the present compositions and/or products is effective when the diarrhea is caused by rotavirus or bacteria.
- a method of killing bacteria comprises the steps of topically applying the composition and/or product of the present invention to an area in need of treatment and, optionally, removing said composition and/or product following application.
- a method of inactivating viruses is disclosed. Said method, too, comprises the steps of topically applying the composition and or product of the present invention to an area in need of treatment and, optionally, removing said composition and/or product following application.
- the method of inactivating viruses is useful in treating viruses selected from the group consisting of: rotavirus, rhinovirus and combinations thereof.
- a method of providing residual antibacterial and antiviral efficacy preferably comprises the steps of topically applying the composition and/or product of the present invention to an area in need of treatment and, optionally, removing said composition following application.
- a method of preventing and/or treating a respiratory disease or diarrhea in a mammal where the sickness is caused by a rhinovirus, coronavirus, RSV or rotavirus, respectively is envisioned.
- Said method comprises the steps of topically applying the composition and/or products of the present invention to an area of the mammal in need of treatment and, optionally, removing said composition and/or product following application.
- the present invention seeks to encompass a method of preventing and/or treating bacteria-related diseases in a mammal that result from said mammal's contact with a bacteria- infected substrate.
- Said method comprises the steps of topically applying the composition and/or product of the present invention to an area of the mammal that is infected with said bacteria and, optionally, removing said composition and/or product following application.
- each of the methods of the present invention comprise the step of topically applying a composition or product comprising same to an area or surface in need of treatment.
- areas and/or surfaces in need of treatment, against which the compositions of the present invention are effective include, but are not limited to: one or more hands, a nose, a nasal canal or passage, an article of clothing, a hard surface, irritated, acne-affected, or injured skin, pre or post surgical areas and combinations thereof.
- antimicrobial compositions or products of the present invention are topically applied to keratinous tissue, e.g. adult hands, they are applied in doses of from about 0.1 mL to about 5 mL per use, more preferably 0.5 mL to about 4 mL, most preferably from about 1 mL to about 3 mL.
- the compositions and products of the present invention are topically applied to surfaces in need of treatment from about 2 to about 6 times daily. Once applied, the compositions are rubbed on the treated surfaces for a period of time to ensure coverage, typically at least 5 seconds, preferably at least 10 seconds, more preferably at least 20 seconds and most preferably at least 30 seconds.
- Example 12 and 16 relate to the preparation of a concentrated version of the antimicrobial compositions of the present invention.
- the product solution of Examples 1 to 12 in Table 1 changed opacity from clear to hazy over time, due to the slow hydrolysis of hydrogenated castor oil.
- the antimicrobial efficacy of the solutions included therein remained unaffected.
- Examples 13 to 16 in Table 2 remained stable as clear aqueous solutions with consistent antimicrobial performance after prolonged storage under stressed conditions (e.g. one month at 45 degree C).
- Tables 3 to 6 summarize the efficacy of a few examples, the preparation of which is summarized in Tables 1 and 2.
- the following disclosure further includes a discussion of the testing methods and results of the compositions disclosed herein, as well as methods for preparing one or more products in accordance with the present invention.
- test bacteria suspension 10 uL was spread on mammalian skin and allowed to air dry for one minute, then 20 uL of the active solution was spread evenly over the treated skin and the preparation was allowed to rest uncovered for five minutes.
- the skin substrate was placed into a test tube containing 10 mL of extraction solution (Phosphate buffer with Triton X-100, Lecithin and Tween) and vortex for 30 seconds.
- extraction solution Phosphate buffer with Triton X-100, Lecithin and Tween
- a 50 uL aliquot was dispensed (via Spiral Biotech Autoplater) onto Trypticase Soy Agar + 1.5% Tween 80 plates and viability was determined after 18 hours of incubation at 37°C (CUF/ml)
- test bacteria suspension (TSB) culture with a density of l.OE+09 CFUs/ml was mixed with 5 ml of the active solution. After one minute time, the inoculated solution was mixed with
- test virus suspension 10 uL was spread on the skin substrate and allowed to air dry at room temperature then 25 uL of the active solution was spread evenly over the treated skin and the preparation was allowed to rest for five minutes. Following the exposure period, a sterile 1.5 ml cryovial containing 1.0 ml of elution medioum was inverted over the sink substrate surface and extraction was performed. The solution was mixed and serial 10 fold dilution was performed. The dilutions were assayed for the presence of virus in a host system. The virus liter of the stock was determined by the median cell culture infective dose (TCID 50). Cytotoxicity to the host system (active solution) at tested concentrations was also determined. The virus-product mixture was assayed in numerous units of the host system. Median values of log 10 virus inactivation were calculated. Residual Efficacy:
- test wipe was inoculated with 1.0 ml of virus suspension to cover one quarter of the folded wipe. 5 minutes after inoculation the treated wipe was placed into a sterile bag containing 100 ml of DE neutralizer medium, the bag was sealed and placed in the Stomacher for 2 minutes. After blending, a 50 uL aliquot was dispensed (via Spiral Biotech Autoplater) onto Trypticase Soy Agar
- the liquid composition produced in accordance with the previous section may be packaged in a typical PET bottle with a flip-top cap. Liquid is dispensed to the hands in an amount to ensure complete wetting. Employing this method delivers immediate microbial il and, upon drying, provides prolonged, residual activity.
- the lotion produced in accordance with the previous section may be used to produce a wet wipe product for topical cleaning and/or sanitizing of skin and/or hard surfaces.
- a wet wipe product for topical cleaning and/or sanitizing of skin and/or hard surfaces.
- Such a product is made by saturating a paper or cloth substrate with the liquid composition prepared in accordance with the previous section. The level of saturation depends upon the substrate in which incorporation of the antimicrobial composition is desired.
- a 5" x 8" hand wipe towelette made from 40-60 grams per square meter spun-lace non-woven material may be saturated with about 1- 3 grams of liquid composition.
- the liquid may be applied to the substrate via spraying and/or soaking prior to final packaging.
- the wipe may be wrapped in single use pouches made from foil or plastic or packed in groups of 10, 40, or more in multiple use tubs.
- the wipe is removed from its package and is rubbed onto the target surface, in a manner that ensures complete wetting of the surface.
- the wetting practice removes visible dirt and eradicates bacteria and viruses. Upon drying, the surface experiences residual antimicrobial activity for several hours.
- the lotion produced in accordance with the previous section may be used to produce a dry towel product for topical cleaning and/or sanitizing of skin or hard surfaces.
- a dry towel product for topical cleaning and/or sanitizing of skin or hard surfaces.
- Such a product is made by saturating a paper or cloth substrate with the liquid prepared in accordance with the preceding section. The substrate is then dried to remove all water. The level of saturation depends upon the substrate in which incorporation of the antimicrobial composition is desired.
- a 5" x 8" towel made from 40-60 grams per square meter spun-lace non-woven material may be saturated with about 1-3 grams of liquid.
- the liquid may be applied to the substrate via spraying and/or soaking prior to final packaging.
- the liquid may also be applied in concentrate form using printing techniques employed in the color design of commercial, paper towels.
- the towel may then be rolled or inserted into boxes.
- the towel is applied to any wet skin or hard surface to dry it.
- the water activates the antimicrobial properties of the composition within the towel, which is then imparted onto the surface.
- the towel dries the target surface, removes visible dirt, delivers anitmicrobial kill and provides prolonged, residual activity.
- the antimicrobial compositions, methods and products of the present invention have demonstrated surprising anti-inflammatory benefits in the topical treatment of inflammation or dermatitis.
- In vitro studies of the present invention and its key components have been conducted to assess the efficacy of the claimed compositions in inhibiting the cycloxygenase (COX) 1 and 2 enzymes.
- Said enzymes are adapted to convert arachidonic acid in cell membranes to prostaglandin, a messenger agent that conveys a signal to the cells to increase and enhance their inflammatory response.
- the results of the aforementioned in vitro study demonstrate that the present invention can significantly reduce the activity of both COX 1 and 2 enzymes.
Abstract
Description
Claims
Priority Applications (6)
Application Number | Priority Date | Filing Date | Title |
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CA2487270A CA2487270C (en) | 2002-06-21 | 2003-06-20 | Antimicrobial compositions, products and methods employing same |
NZ536482A NZ536482A (en) | 2002-06-21 | 2003-06-20 | Antimicrobial compositions, hygiene and personal care products and use thereof |
JP2004530966A JP2005530857A (en) | 2002-06-21 | 2003-06-20 | Antibacterial compositions, antibacterial products, and methods of using them |
EP03761254A EP1515607A2 (en) | 2002-06-21 | 2003-06-20 | Antimicrobial compositions, products and methods employing same |
AU2003243732A AU2003243732B2 (en) | 2002-06-21 | 2003-06-20 | Antimicrobial compositions, products and methods employing same |
NO20050345A NO20050345L (en) | 2002-06-21 | 2005-01-21 | Antimicrobial preparations, products and methods using the same |
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US10/177,445 US20040001797A1 (en) | 2002-06-21 | 2002-06-21 | Antimicrobial compositions, products and methods employing same |
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US10/263,211 US20030235550A1 (en) | 2002-06-21 | 2002-10-02 | Antimicrobial compositions, products and methods employing same |
US10/263,211 | 2002-10-02 |
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JP (1) | JP2005530857A (en) |
AU (1) | AU2003243732B2 (en) |
CA (1) | CA2487270C (en) |
NO (1) | NO20050345L (en) |
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Also Published As
Publication number | Publication date |
---|---|
CA2487270C (en) | 2010-10-26 |
CA2487270A1 (en) | 2003-12-31 |
WO2004000016A3 (en) | 2004-04-29 |
JP2005530857A (en) | 2005-10-13 |
AU2003243732A1 (en) | 2004-01-06 |
EP1515607A2 (en) | 2005-03-23 |
NO20050345L (en) | 2005-03-17 |
AU2003243732B2 (en) | 2008-02-28 |
NZ536482A (en) | 2007-03-30 |
WO2004000016A9 (en) | 2005-07-14 |
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