WO2011105985A1 - Sels biocides à libération contrôlée - Google Patents

Sels biocides à libération contrôlée Download PDF

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Publication number
WO2011105985A1
WO2011105985A1 PCT/US2010/000607 US2010000607W WO2011105985A1 WO 2011105985 A1 WO2011105985 A1 WO 2011105985A1 US 2010000607 W US2010000607 W US 2010000607W WO 2011105985 A1 WO2011105985 A1 WO 2011105985A1
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WIPO (PCT)
Prior art keywords
salt
acid
biocidal
component
group
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PCT/US2010/000607
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English (en)
Inventor
Anthony J. Sawyer
Richard F. Stockel
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Colorado Synthetics, Inc.
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Priority to PCT/US2010/000607 priority Critical patent/WO2011105985A1/fr
Publication of WO2011105985A1 publication Critical patent/WO2011105985A1/fr

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Classifications

    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23B—PRESERVING, e.g. BY CANNING, MEAT, FISH, EGGS, FRUIT, VEGETABLES, EDIBLE SEEDS; CHEMICAL RIPENING OF FRUIT OR VEGETABLES; THE PRESERVED, RIPENED, OR CANNED PRODUCTS
    • A23B4/00—General methods for preserving meat, sausages, fish or fish products
    • A23B4/14—Preserving with chemicals not covered by groups A23B4/02 or A23B4/12
    • A23B4/18—Preserving with chemicals not covered by groups A23B4/02 or A23B4/12 in the form of liquids or solids
    • A23B4/20—Organic compounds; Microorganisms; Enzymes
    • 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
    • A01N37/44—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 nitrogen atom attached to the same carbon skeleton by a single or double bond, this nitrogen atom not being a member of a derivative or of a thio analogue of a carboxylic group, e.g. amino-carboxylic acids
    • 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
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
    • A01N43/36—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom five-membered rings
    • A01N43/38—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom five-membered rings condensed with carbocyclic rings
    • 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
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
    • A01N43/50—1,3-Diazoles; Hydrogenated 1,3-diazoles
    • 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
    • A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
    • A01N47/40—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having a double or triple bond to nitrogen, e.g. cyanates, cyanamides
    • A01N47/42—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having a double or triple bond to nitrogen, e.g. cyanates, cyanamides containing —N=CX2 groups, e.g. isothiourea
    • A01N47/44—Guanidine; Derivatives thereof
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
    • A23L3/00—Preservation of foods or foodstuffs, in general, e.g. pasteurising, sterilising, specially adapted for foods or foodstuffs
    • A23L3/34—Preservation of foods or foodstuffs, in general, e.g. pasteurising, sterilising, specially adapted for foods or foodstuffs by treatment with chemicals
    • A23L3/3454—Preservation of foods or foodstuffs, in general, e.g. pasteurising, sterilising, specially adapted for foods or foodstuffs by treatment with chemicals in the form of liquids or solids
    • A23L3/3463—Organic compounds; Microorganisms; Enzymes
    • A23L3/3526—Organic compounds containing nitrogen

Definitions

  • the invention relates to controlled release biocidal salts that are environmentally safe that can have antimicrobial, antibacterial, antiviral, antifungal properties and/or skin/hair activity.
  • the salts of the invention which can be used as preservatives comprise two components: a first component comprising a cation of a N° - (Ci - C22) alkanoyl di-basic amino acid alkyl (Ci - C 22 ) ester cationic biocidal molecule and a second component comprising an anion of a monomeric anionic molecule having insignificant biocidal activity.
  • compositions especially those that are referred to as "green"
  • biocidal materials that have controlled release (also referred to as extended release) properties and also can be used as preservatives.
  • the use of natural or naturally-derived materials is also very much of interest in topically applied and ingested compositions. It is also important that both green and naturally-derived materials be utilized in a composition that will provide antimicrobial, antibacterial, antifungal, antiviral and skin/hair beneficial properties as well as preservative capability and controlled release properties. If all of the components of a biocidal composition are GRAS (Generally Regarded as Safe) and are approved for food use, the resulting composition could also be ingested with little or no side effects. Since the use of food-grade materials are being promoted as a strategy of selecting ingredients that are intended to be applied to skin/hair, compositions utilizing GRAS ingredients would meet such need.
  • preservatives are not green and are not natural or naturally-derived and many are not approved for food use. There is a growing movement in the cosmetics industry to avoid the use of ingredients that cannot be eaten. Furthermore, commonly-used preservatives do not possess controlled release properties which would allow continuous release of the preservative at effective levels as the preservative is consumed. If a preservative composition having controlled release properties also included GRAS ingredients that have an antimicrobial component as well as a naturally occurring component that has skin/hair benefits, then such approach would be beneficial in reducing the potential irritation from hash chemicals while improving skin/hair health.
  • the invention pertains to environmentally safe controlled release biocidal salts that have antimicrobial, antibacterial, antifungal and antiviral properties as well as skin/hair beneficial properties.
  • biocidal salts can be considered to be green and natural or naturally derived and are particularly useful for cosmetic applications and for the preservation of foods. Details of the Invention
  • the controlled release biocidal salts of the invention comprise a first component comprising a cation of a ⁇ ⁇ - (Ci - C22) alkanoyl di-basic amino acid alkyl (Ci - C22) ester cationic biocidal molecule and a second component comprising an anion of a monomeric anionic molecule having insignificant biocidal activity.
  • the salt is such that when it is exposed to an aqueous medium, the salt partially dissolves thereby releasing biocidal ions in an amount sufficient to exceed the MIC or MBC of a target bacteria being controlled, and further characterized as leaving a residual reservoir of undissolved salt capable of releasing more biocidal ions as the salt is consumed or otherwise removed from the environment encompassing the target bacteria.
  • the di-basic amino acid of the first component is selected from the group consisting of arginine, lysine, histidine and tryptophan.
  • the most preferred cationic biocidal molecule is N a -lauroyl-L-arginine ethyl ester, hereinafter frequently referred to as "LAE”.
  • MIC and MCC employed in the description and the claims, refer to the Minimum Inhibitory Concentration and Minimum Bactericidal Concentration, respectively.
  • biocidal ions typically, about 2 to about 500 ppm of biocidal ions are released when the salt is exposed to an aqueous medium such as water.
  • aqueous medium such as water.
  • CPC cetyl pyridinium chloride
  • PCMX para-chloro-meta-xylenol
  • triclosan biocidal ions are needed to inhibit or kill microbes such as bacteria, fungi and yeasts.
  • Microbiological testing can be used to establish the MIC or MBC of a target microbe.
  • Simple analyses can be used to determine the solubility of the biocidal salt and hence to establish its ability to provide continuous release as the biocidal ion is consumed or is otherwise removed from the environment encompassing the target microbe. For those situations in which a very rapid inhibition or kill of a microbe is required, excess amounts of the first component can be provided together with the polymeric biocidal salt to rapidly sanitize the area to be treated.
  • the molar ratio of the first component to the second component Is such that there is an equivalency between the first component and the second component.
  • excess amounts of the first component can be provided together with the salt of the invention to rapidly sanitize the area to be treated.
  • the salt of the invention releases at least about 2 ppm of biocidal ions when the salt is exposed to an aqueous medium such as water.
  • the monomeric anionic molecule having insignificant biocidal activity will contain a moiety selected from the group consisting of carboxylic, hydroxycarboxylic, phenolic (e.g., resorcinol, ferulic acid), pentacyclic triterpenoid, enol (e.g., ascorbic acid, its esters and its phosphate salts and dehydroacetic acid), acidic amino acid, a protein having a residual negative charge, a phosphate moiety present on a DNA nucleotide, an anionic phospho- lipid, bis-phosphonate, phosphonate, sulfate, sulfonate and mixtures of the foregoing moieties.
  • a moiety selected from the group consisting of carboxylic, hydroxycarboxylic, phenolic (e.g., resorcinol, ferulic acid), pentacyclic triterpenoid, enol (e.g., ascorbic acid, its
  • the carboxylic moiety comprises a carboxylic acid selected from the group consisting of adapalene; isotretinoin; pantothenic acid; benzoic acid; salicyclic acid; retinoic acid; tretinoin; an aldobionic acid; undecylenic acid; an a-hydroxycarboxylic acid; a ⁇ -hydroxycarboxylic acid; an a-ketocarboxylic acid; a ⁇ -keto carboxylic acid; an aromatic carboxylic acid; and azelaic acid.
  • Suitable a-hydroxycarboxylic acids include glycolic, lactic, tartaric, mandelic, malic, citric, gluconic, glyceric and glyoxylic.
  • the carboxylic moiety may be a Cs - C 22 saturated or unsaturated fatty acid.
  • saturated fatty acids include lauric, myristic, palmitic, and stearic acids.
  • unsaturated fatty acids include linolenic, arachidonic, oleic, linoleic, and eicosapentanoic and docosahexenoic acids.
  • Other compounds useful as the second component are the polyphenols and derivatives thereof. Polyphenols are a group of chemical substances found in plants and are characterized by the presence of one or more phenolic units.
  • Suitable polyphenols are ferulic acid, reservatrol, gallic acid, coumaric acid, catechin, caffeic acid, vanillic acid, chlorogenic acid, and aplanin and sinapyl arbutin.
  • Additional useful second components are the pentacyclic triperpenoids, such as betulinic acid, moronic acid, ursolic acid and oleanolic acid.
  • the salts of the invention include a saturated C6 - C14 fatty acid monoglyceride such as glycerol monolaurate. If present, the monolaurate is utilized in an amount of about 1 to about 10wt. %, based on the weight of the salt.
  • the salts of the invention may be prepared by a metathesis reaction between an acid salt of the first component and an alkali or alkaline earth metal salt of the second component.
  • the salts of the invention may be prepared by an acid-base reaction between the first component present in the form of its free base and the second component present in the form of an undissociated molecule having a transferable proton.
  • the metathesis and acid-base reactions are described in detail below.
  • metathesis is a reaction involving the exchange of elements or groups as in the general reaction:
  • the metathesis reaction is straight forward and can be readily carried out in aqueous solutions using water alone or a mixture of water and up to about 85wt.% of a solvent such as a Ci - C 4 alcohol, e.g., methanol, ethanol, isopropanol, n- butanol, etc.
  • a solvent such as a Ci - C 4 alcohol, e.g., methanol, ethanol, isopropanol, n- butanol, etc.
  • a solvent such as a Ci - C 4 alcohol, e.g., methanol, ethanol, isopropanol, n- butanol, etc.
  • water alone or water-alcohol solvent will be utilized in an amount of about 40 to about 85wt. %, based on the weight of the reaction mixture.
  • Water is the solvent of choice; the by-products are harmless salts and the yields of the salt of the invention range from excellent to quantitative. Where one or both of the react
  • An alkali or alkaline earth metal (e.g., Na, K, Li, Ca, etc.) salt of the selected first component is formed by reacting it with an equivalent amount of an alkali or alkaline earth metal hydroxide in water or water-alcohol solution.
  • An acid salt, e.g., acetate, hydrohalide, gluconate, sulfate, etc. of the selected second component is formed by reacting it with an equivalent amount of an acid such as acetic, hydrochloric, hydrobromic, gluconic acid, sulfuric, etc. in water or water- alcohol solution.
  • aqueous alkali or alkaline earth metal salt solution of the selected first component is mixed with the aqueous acid salt solution of the selected second component.
  • concentration of the reactants can vary from about 20 to about 60wt. % of the total reaction mixture. Mixing is continued at room temperature for several minutes up to about one hour.
  • the reaction product may be readily recovered by decantation of the supernatant layer (which contains the byproduct salts) or by filtration.
  • the solid layer consisting of the salt of the invention may be used as is for many of the applications recited below or dried (e.g., in air, in vacuuo at a temperature of about 50 to about 130°C, etc.).
  • the salt may be recrystallized using a solvent such that the solubility of the salt in the solvent is low at room temperature, but the solubility increases significantly near the boiling point of the solvent.
  • the K sp of the salt of the invention will generally be about 6 x 10 2 moles/liter or less.
  • the acid-base reaction it is preferred to use the acid-base reaction to prepare the polymeric salts of the invention rather than the metathesis reaction since the acid-base reaction does not result in by-product salts that must be disposed of in an environmentally sound manner.
  • the selected first component be present in the form of its free base having a pKb numerical value of at least about 6 and the second component be present in the form of its undissociated acid having a pKg numerical value of about 8 or less.
  • the selected first component must be present in the form of its acid having a pKa numerical value of about 8 or less and the second component must be present in the form of its free base having a pKb numerical value of at least about 6.
  • the acid-base reaction is typically carried out in the presence of about 40 to about 80wt. % of a solvent consisting of a Ci - C4 alcohol or a mixture of about 20 to about 60wt. % water and such alcohol.
  • the reaction mixture is generally stirred under reflux for about 30 minutes to about 10 hours and the reaction product, i.e., the polymeric biocidal salt of the invention, is recovered by evaporation of the solvent.
  • the reaction product may be recrystallized using a solvent or a mixture of solvents such as isopropanol, propylene glycol, dimethyl formamide, etc., or with small amounts of water.
  • the molar ratio of the first component to the second component is such that the polymeric biocidal salt of the invention will bear a charge ranging from less than 50% negative charge to neutrality to less than 50% positive charge.
  • the acid-base reaction may be illustrated by the following equation: N a -lauroyl-L-arginine ethyl ester + lauric acid ⁇ ⁇ ⁇ -lauroyl-L-arginine ethyl ester la urate
  • the controlled-release biocidal salts of the invention typically have limited solubility in aqueous media such as water. Therefore, for many of the applications described below, it is desirable to utilize the salts in the form of emulsions or microemulsions.
  • the following is a generalized procedure for preparing emulsions or microemulsions of the salts.
  • the selected salt is dissolved in the minimum amount ⁇ a solvent that will completely dissolve the salt in the amount that is intended for use in the desired application.
  • the solvent of choice will be one with the appropriate Hildebrand solubility parameter.
  • the solubility parameter is a numerical value that indicates the relative solvency behavior of a specific solvent.
  • Hildebrand solubility parameters of about 8.5 to about 22.0 are generally suitable for solubilization of the salts.
  • Exemplary solvents with the requisite Hildebrand solubility parameters include ethanol, glycerin, propylene glycol, sorbitol, methanol and the like.
  • the desirable Hildebrand solubility parameter will depend on the ionic/covalent bonding energies of the salts.
  • the correct solvent will be one having a relatively low Hildebrand solubility parameter if the bonding has more covalency and a relatively high Hildebrand solubility parameter if the bonding is more ionic.
  • combinations of correct solvents may also be utilized to dissolve the salts.
  • the surfactant may be cationic, anionic or amphoteric in nature, and combinations of the different types or combinations of the same type of surfactants may be use.
  • the surfactant will be amphoteric or nonionic in nature. Highly negative anionic surfactants are not very functional.
  • the last step is to dilute the salt-solvent-surfactant composition with water to the concentration desired for the selected application so as to form an emulsion or microemulsion depending on the micellar size and the choice of solvents/cosolvents/surfactant(s).
  • the Surfactants are used to dilute the salt-solvent-surfactant composition with water to the concentration desired for the selected application so as to form an emulsion or microemulsion depending on the micellar size and the choice of solvents/cosolvents/surfactant(s).
  • the surfactants employed in the formation of microemulsions (cosolvents are added) or emulsions of the salts are generally of the nonionic or amphoteric type or combinations of one or more nonionics, one or more amphoterics or one or more nonionics in combination with one or more amphoterics.
  • Highly charged anionic surfactants are less desirable since they have the potential to reduce the biocidal activity of the salts by causing some degree of precipitation, thereby lessening the effectiveness of the salts.
  • cationic phospholipids preferably in combination with nonionic and/or amphoteric surfactants are effective in the formation of microemulsions or emulsions of the salts.
  • amphoteric Surfactants that carry a positive charge in strongly acidic media carry a negative charge in strongly basic media, and form zwitterionic species at intermediate pH levels are amphoteric.
  • the preferred pH range for stability and effectiveness is about 5.0 to about 9.0.
  • the amphoteric surfactant is mostly or fully in the zwitter (neutral) form, thereby negating any dilution of biocidal activity of the salts, provided that the surfactant is employed in the preferred concentration range of about 0.25 to about 4.0wt. %, based on the weight of the salt in the final formulation.
  • amphoteric amidobetaines nonionic polyethoxylated sorbital esters, polycondensates of ethylene oxide-propylene oxides (polyoxamers), polyethoxylated hydrogenated castor oils, and certain cationic phospholipids.
  • amidobetaines include cocoamidoethyl betaine, cocoamido-propyl betaine; and mixtures thereof.
  • suitable amphoteric surfactants include long chain imidazole derivatives such as the product marketed under the trade name "Miranol C2M” by Rhodia and long chain betaines such as the product marketed under the trade name "Empigen BB” by Huntsman Corporation, and mixtures thereof.
  • Suitable nonionic surfactants include polyethoxylated sorbitol esters, especially poly-ethoxylated sorbital monoesters, e.g., PEG sorbitan di-isostearate, and the products marketed under the trade name Tween" by ICI; polycondensates of ethylene oxide and propylene oxide (polyoxamers), e.g., the products marketed under the trade name "Pluronic” by BASF; condensates of propylene glycol; polyethoxylated hydrogenated castor oil such as the products marketed under the trade name "Cremophors" by BASF; and sorbitan fatty esters marketed by ICI.
  • Other effective nonionic surfactants include the polyalkyl (Ce - Cie) glucosides.
  • Suitable cationic surfactants include D,L- pyrrolidone-5-carboxylic acid salt of ethyl- cocoyl-L-arginate (CAE) marketed by Ajinomoto, and cocoamidopropyl (PTC), lauramidopropyl PG diammonium chloride phosphates and the like marketed by Uniqema.
  • CAE ethyl- cocoyl-L-arginate
  • PTC cocoamidopropyl
  • lauramidopropyl PG diammonium chloride phosphates and the like marketed by Uniqema.
  • the controlled release biocidal salts of the invention are suitable for a wide range of applications. It should be understood that this list is presented for illustrative purposes only and does not represent any limitation as to possible applications. It should be further understood that it is within the purview of this invention that the products described below may be combined with conventional antioxidants, antibacterial agents, antifungal agents, hormones, vitamins, antioxidants, hydroxy acids, cleansers, soaps, shampoos, silicones, biocides, humectants, emollients, synthetic or natural oils, deodorizers, perfumes, colorants, preservatives, plant extracts, etc.
  • skin and hair care products e.g., sunscreens; suntan lotions; after-sun gels, lotions and creams; antiperspirants; deodorants (solutions, powders, gels, roll-ons, sticks, sprays, pastes, creams, lotions); cleansing creams; skin conditioners; skin moisturizers; protectants; skin aging products; skin wrinkle reduction products; products for treatment of acne; products for treatment of rosacea; age-spot reduction products; stretch-mark reduction products; pimple treatment products, skin soothing products; skin infection and lesion treatment products; skin-redness reduction products; stretch-mark reduction products; varicose and spider-vein reduction products; lotions; oils; hand/body creams; shaving gels/creams; body washes; liquid and solid soaps; blood microcirculation improvement products, cellulite reduction products, body toning products, skin penetration enhancers; skin whitening products; cosmetics; shampoos; shower gels; bubble baths; hair treatment products, e.g., medicated shampoos,
  • dental care materials mouthwash; dentifrice; dental floss coated and/or impregnated with the salt; protective coating for teeth; toothbrush bristles coated and/or impregnated with the salt; orthodontic appliance coated and/or impregnated with the salt; orthodontic appliance adhesive; denture appliance coated and/or impregnated with the salt; denture appliance adhesive; endodontic composition coated and/or impregnated with the salt; composite-type dental restorative materials; dental cement; dental liner; dental bonding agent; and the like.
  • foods and food products food-stuffs; animal feed-stuffs; grains; breads; bakery products; confectionary; potato products; pasta products; salads; soups; seasonings; condiments; syrups; jams, jellies and marmalades; dairy products; egg-based products; meats and meat-based products; poultry and poultry-based products; fish and fish-based products; crustaceans and crustacean-based products; fresh and dried fruit products; vegetables and vegetable products; greens; salads; sauces; beverages, e.g., wines, tea extracts, beers, juices; and the like.
  • plastics and miscellaneous products, coated and/or impregnated with the salt including: medical items, e.g., thermometers, catheters, surgical sutures, blood lines, implants, bandages, surgical dressings, surgical apparel, respirators, etc.; food packaging; fluid-dispensing tubing; drug and cosmetic packaging; eating utensils; shower curtains; bath mats; sponges; mops; toilet seats, rubber gloves; contact lenses; hearing aids; shelving paper; carpet pads; pool covers; animal bedding and cat litter; computer covers and computer keys; doorknobs; tampons and sanitary napkins; adult novelties; sexual aids; sex toys; condoms; pregnancy barriers; dental chairs; dryer sheets; dishcloths; paints and coatings; powdered, liquid, gel and spray cleaners for floors, sinks, counter-tops, walls, tiles, carpets; deodorizing liquids, solids, sprays, gels and powders; filters; foams; hair brushes; combs; diaper rash preventer;
  • fibers and fabrics coated and/or impregnated with the salt including natural and synthetic fibers and fabrics manufactured from such fibers; wipes, cloths; surgical gauze; crib covers; bassinet covers; bed linens; towels and wash cloths; tents; draw sheets; cubicle curtains; shower curtains; wall coverings; wood and wood products; hospital clothing such as examination robes, physicians' coats, nurses uniforms, etc.; apparel; paper, non-woven fabric, knitted fabric, woven fabric, brick, stone, plastic, polymer, latex, metal, tile, walls, floors, gurneys, tables, or trays; shoes and the like.
  • facial cream as an acne treatment
  • bactericidal bactericidal
  • fungicidal fungicidal
  • virucidal shampoo, hand lotion
  • athlete's foot medication osteointment, powder, soap
  • candies for sore throat, bad breath, recurrent herpes
  • ointment or foam spray for genital herpes legion treatment
  • shaving cream mouth wash; after shave lotions; lip balm; paste; and the like
  • the controlled release biocidal salt of the invention will typically be applied to the food product in the form of an aqueous emulsion or microemulsion such that the salt will be present in an amount of about of about 10 to about 1 ,000 parts per million parts of food product, preferably 40 to 200 parts per million parts of food product.
  • the salt may be applied to the food product by conventional techniques, e.g., spraying, immersion, dipping or injection.
  • the salt may be incorporated in a suitable packaging material by techniques such as dissolution in thermoplastic resins, melt spun or melt blown into the packaging material, etc.
  • the packaging material may be any GRAS material, e.g. a thermoplastic material such as a polyolefin and copolymers thereof, polyesters, polyvinyl chloride, polyacrylate, polyamide, etc., that is suitable for packaging food products.
  • the packaging material containing the salt of the invention would then be placed in contact with the food product. This technique would result in a wrapped perishable food and would greatly reduce the amount of preservative from finding its way into the food product.
  • LAE laurate N a -lauroyl-L-arginine ethyl ester laurate
  • Two beef tenderloins containing a large quantity of purge i.e., liquid surrounding raw meats; meat soaker pads were used to trap such liquids to the extent possible
  • the purge was isolated from the packages and transferred to a series of test tubes and 10 ml of purge were placed in each test tube.
  • To the test tubes was added 0.5 g of either LAE hydrochloride or LAE mono-laurate salts.
  • the samples were mixed in a vortex mixer and serial dilutions were then plated on petrifilm for readings at time zero.
  • the test tubes were then placed in the refrigerator and were again plated at 24 hours and 48 hours.
  • the beef purge contained naturally-occurring aerobic bacteria.
  • Aloe vera gel was prepared as a 50% dilution and dispensed as 20g per container.
  • Inoculum was prepared as 48 hour yeast cultures in tripticase soy broth and A. niger suspension. The inoculum was pooled and " ⁇ added to each container. The preservatives were prepared as 1 % solutions and added to each pre-labeled container. The samples were well mixed and stored. Recoveries were carried out at selected intervals (1 :10 dilutions plated with sabourad dextrose agar. Pre-labeled plates were incubated at 25-30°C for 48-72 hours; the pH of the samples was in the range of 4-4.5. The plates were removed from incubation, counted cfu recorded and converted to log reduction values.
  • the initial challenge was 7 logs at day 0. Thereafter, re-challenges of 7 logs each were made at day 21 and day 28. The results were that after the two re-challenges, the LAE-lactate salt was superior to LAE-HCI.
  • LAE-HCI showed a decrease at day 28 versus the LAE-lactate salt and almost no reduction at day 35 after the second re-challenge, compared to a 4.0 log reduction for the LAE-lactate salt. Further, the LAE-lactate salt continued to exhibit a log reduction even at day 42.
  • Lactic acid 1500 ppm 0 1.0 0.2 0.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0

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Abstract

L'invention porte sur un sel biocide à libération contrôlée d'un premier composant comprenant un cation d'une molécule biocide cationique ester alkylique en (C1-C22) d'acide Nα-(alcanoyl en C1-C22)aminodiacide et d'un second composant comprenant un anion d'une molécule anionique monomère ayant une activité biocide négligeable. Le sel est caractérisé en ce que, lorsqu'il est exposé à un milieu aqueux, il se dissout partiellement, ce qui libère de cette manière des ions biocides en une quantité suffisante pour dépasser la MIC ou la MBC de bactéries cibles contre lesquelles on cherche à lutter, et il est en outre caractérisé en ce qu'il laisse un réservoir résiduel de sel non dissous pouvant libérer plus d'ions biocides au fur et à mesure que le sel est consommé ou autrement enlevé de l'environnement comprenant les bactéries cibles. La molécule biocide cationique préférée comprend de l'ester éthylique de Nα-lauroyl-L-arginine (« LAE »).
PCT/US2010/000607 2010-02-27 2010-02-27 Sels biocides à libération contrôlée WO2011105985A1 (fr)

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US11832638B2 (en) 2012-03-30 2023-12-05 Givaudan Sa N-acyl derivatives of gamma amino-butyric acid and beta alanine as food flavouring compounds
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US11492326B2 (en) 2012-03-30 2022-11-08 Givaudan Sa Organic compounds
US10201175B2 (en) 2012-03-30 2019-02-12 Givaudan Sa N-acylated 1-aminocycloalkyl carboxylic acids as food flavouring compounds
US11091429B2 (en) 2012-03-30 2021-08-17 Givaudan Sa Organic compounds
US10582715B2 (en) 2012-03-30 2020-03-10 Givaudan Sa Powder flavour composition
US10913922B2 (en) 2012-03-30 2021-02-09 Givaudan S.A. N-acylated methionine derivatives as food flavoring compounds
US10645955B2 (en) 2012-03-30 2020-05-12 Givaudan Sa N-acyl derivatives of gamma amino-butyric acid and beta alanine as food flavouring compounds
US10856563B2 (en) 2012-03-30 2020-12-08 Givaudan S.A. N-acyl-amino acid derivatives for improvement of the flavor profile of edible compositions
US10711230B2 (en) 2012-03-30 2020-07-14 Givaudan Sa N-acyl proline derivatives as food flavoring compounds
EP2846637B1 (fr) 2012-05-07 2017-11-01 Nevada Naturals, Inc. Agents antimicrobiens synergiques
US10834950B2 (en) 2013-10-02 2020-11-17 Givaudan S.A. Organic compounds
US10834943B2 (en) 2013-10-02 2020-11-17 Givaudan S.A. Organic compounds having taste-modifying properties
WO2015048990A1 (fr) * 2013-10-02 2015-04-09 Givaudan Sa Composés organiques présentant des propriétés de modification du goût
US10834951B2 (en) 2013-10-02 2020-11-17 Givaudan S.A. Organic compounds
US10674755B2 (en) 2013-10-02 2020-06-09 Givaudan S.A. Organic Compounds
CN105636457B (zh) * 2013-10-02 2020-03-10 奇华顿股份有限公司 具有味道改进特性的有机化合物
US10975018B2 (en) 2013-10-02 2021-04-13 Givaudan Sa Organic compounds
US10537127B2 (en) 2013-10-02 2020-01-21 Givaudan S.A. Organic compounds
US11122826B2 (en) 2013-10-02 2021-09-21 Givaudan Sa Organic compounds
US20160242444A1 (en) * 2013-10-02 2016-08-25 Givaudan Sa Organic Compounds having Taste-Modifying Properties
CN105636457A (zh) * 2013-10-02 2016-06-01 奇华顿股份有限公司 具有味道改进特性的有机化合物
US11834393B2 (en) 2013-10-02 2023-12-05 Givaudan Sa Organic compounds having taste-modifying properties
US9695073B2 (en) 2014-07-30 2017-07-04 Ecolab Usa Inc. Dual biocide generator

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