WO2020229202A1 - Lactylate blend for preservative/antimicrobial system - Google Patents

Lactylate blend for preservative/antimicrobial system Download PDF

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Publication number
WO2020229202A1
WO2020229202A1 PCT/EP2020/062194 EP2020062194W WO2020229202A1 WO 2020229202 A1 WO2020229202 A1 WO 2020229202A1 EP 2020062194 W EP2020062194 W EP 2020062194W WO 2020229202 A1 WO2020229202 A1 WO 2020229202A1
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Prior art keywords
composition
preservative
antimicrobial system
antimicrobial
surfactant
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PCT/EP2020/062194
Other languages
French (fr)
Inventor
Esther LANSDAAL
Rupert GIJSSEN
Evelien JOCHEMS
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Purac Biochem B.V.
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Publication of WO2020229202A1 publication Critical patent/WO2020229202A1/en

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    • AHUMAN NECESSITIES
    • A01AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01NPRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N37/00Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
    • A01N37/36Biocides, 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
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00Cosmetics or similar toiletry preparations
    • A61K8/18Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/33Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/36Carboxylic acids; Salts or anhydrides thereof
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00Cosmetics or similar toiletry preparations
    • A61K8/18Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/33Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/37Esters of carboxylic acids
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61QSPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00Preparations for care of the skin
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2800/00Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
    • A61K2800/40Chemical, physico-chemical or functional or structural properties of particular ingredients
    • A61K2800/52Stabilizers
    • A61K2800/524Preservatives
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2800/00Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
    • A61K2800/40Chemical, physico-chemical or functional or structural properties of particular ingredients
    • A61K2800/59Mixtures
    • A61K2800/592Mixtures of compounds complementing their respective functions
    • A61K2800/5922At least two compounds being classified in the same subclass of A61K8/18
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61QSPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00Preparations for care of the skin
    • A61Q19/10Washing or bathing preparations
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61QSPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q5/00Preparations for care of the hair
    • A61Q5/02Preparations for cleaning the hair

Definitions

  • the present invention relates to a preservative/antimicrobial system, a cleaning composition and personal care composition comprising said
  • preservative/antimicrobial system a method for preservation, a method for killing microbial cells and the use of said preservative/antimicrobial system in cleaning, personal care, agrochemical products, inks and coatings.
  • compositions that deteriorate or spoil as a result of the presence and the growth of microorganisms can have a very short shelf life, that is the period during which they can usefully be employed, unless they are refrigerated, frozen or sterilized within a sealed container.
  • compositions which are intended for occasional or regular use by the consumer for example as cleaning products, agricultural products, beauty products or cleansing products for the skin, hair or teeth, it is inconvenient to maintain them under refrigerated conditions, and normally impossible to prevent contamination by
  • a preservative chemical such as 2-bromo-2-nitropropane- 1 ,3-diol (Bronopol), methyl paraben or other commonly used preservatives such as isothiazolinones, phenoxy ethanol, parabens, acids and its salts (like lactic, sorbic, benzoic).
  • a preservative chemical such as 2-bromo-2-nitropropane- 1 ,3-diol (Bronopol), methyl paraben or other commonly used preservatives such as isothiazolinones, phenoxy ethanol, parabens, acids and its salts (like lactic, sorbic, benzoic).
  • lactylates show efficacy against certain specimen, however the individual lactylates were found not to be effective against a full spectrum of bacteria, yeasts, fungi and moulds.
  • an antibacterial composition based on a combination of fatty acid ester of fatty acid and hydroxy carboxylic acid with an antibacterial agent selected from polylysine, protamine, their salts and mixtures hereof.
  • the hydroxy carboxylic acid may be present as acid in its free form, in its salt form and/or in its ester form.
  • the publication is further directed to the use of said composition as antibacterial agent against gram-negative bacteria in various products, applications and methods.
  • the invention is related to products comprising said antibacterial agent.
  • C10-C14 lactylates are used either alone or in combination with polylysine.
  • WO 98/22086 describes an aqueous cleansing composition suitable for claiming human skin and hair, which comprises:
  • a short-chain anionic surfactant chosen from C6-C9 alkyl ether sulphates, C5-C11 acyl lactylates, C6-C9 acyl methyl taurates, C6-C9 acyl isethionates, C6-C11 fatty acid soaps, C6-C9 alkyl sulphates, C6-C11 acyl sarcosinates, C6-C9 alkyl sulphosuccinates, C6-C9 alkyl ether sulphosuccinates, or mixtures thereof; (b) a long-chain anionic surfactant chosen from C13-C1 s alkyl ether sulphates, C13- C1 s acyl lactylates, C13-C16 acyl methyl taurates, C13-C15 acyl isethionates, C13- C16 alkyl sulphates, C13-C16 acyl sarc
  • a medium-chain anionic surfactant chosen from C10-C12 alkyl ether sulfates, C12 acyl lactylates, C10-C12 acyl methyl taurates, C10-C12 acyl
  • At least one of the surfactants (a) and (b) is selected from the group consisting of the acyl lactylates, the acyl sarcosinates, the acyl methyl taurates, the alkyl ether sulphates and the acyl isethionates, or the short-chain anionic surfactant
  • (a) is a C6-C11 fatty acid soap; (ii) if surfactant (c) is present, then the surfactants (a),
  • EP 0572271 discloses the use of acyl lactylate as antimicrobial actives, that is to inhibit or prevent the growth of micro-organisms or to reduce the amount of micro organisms present.
  • acyl lactylate as antimicrobial actives, that is to inhibit or prevent the growth of micro-organisms or to reduce the amount of micro organisms present.
  • single acyl acrylates such as hexanoyl lactylate octanoyl lactylate and a 50/50 mixture of sodium capryl/sodium lauryl lactylate are used.
  • WO 2002/08377 discloses an antimicrobial composition comprising an enzymatic component and one or more non-enzymatic biocides; a method for killing or inhibiting microbial cells comprising a treatment with the antimicrobial composition and a detergent composition comprising the antimicrobial composition.
  • WO 2009/037274 is directed to a method for preserving acidic beverages having a pH of or below 4.8 against fungi, yeasts and bacteria.
  • Said preservation method comprises the application of a composition based on polylysine and/or a salt hereof in combination with a second preservative agent selected from glyceride and/or fatty acid ester of hydroxycarboxylic acid in its acidic, salt or ester form.
  • a second preservative agent selected from glyceride and/or fatty acid ester of hydroxycarboxylic acid in its acidic, salt or ester form.
  • the use of C6- C18 lactylates is preferred and the combination of C12 and C14 lactylates is specifically mentioned.
  • compositions especially those useful when applied topically to tissue, such as mucosal tissues (i.e. , mucous membranes), that include an antimicrobial selected from the group consisting of peroxides, C6-C14 alkyl carboxylic acids, C6-C14 alkyl carboxylate ester carboxylic acids, C8-C22 mono- or polyunsaturated carboxylic acids, and antimicrobial natural oils.
  • the compositions can also include an enhancer component, a surfactant, a hydrophobic component, and/or a hydrophilic component.
  • Such compositions provide effective topical antimicrobial activity and are accordingly useful in the treatment and/or prevention of conditions that are caused, or aggravated by, microorganisms.
  • US 2005/053593A is generally related to a product and process to reduce the microbial contamination on organic matter, such as processed meat, fruits and vegetables, plant parts, inanimate surfaces such as textiles and stainless steel, and in the mouth or on dental products.
  • the invention is related to a product and process to disinfect surfaces using an antimicrobial composition containing an antimicrobial lipid, an enhancer selected from the group consisting of bacteriocins, antimicrobial enzymes, sugars, sugar alcohols, iron-binding proteins and derivatives thereof, siderophores, and combinations thereof, and optionally a surfactant.
  • the compositions may optionally also contain a surfactant (i.e., one or more surfactants).
  • Suitable surfactants include acyl lactylate salts, dioctyl sulfosuccinate salts, lauryl sulfate salts, dodecylbenzene sulfonate salts, and salts of (C8-C18) fatty acids.
  • US 6001787 discloses an aqueous cleansing composition, which comprises: (a) a short-chain anionic surfactant chosen from C6-C9 alkyl ether sulphates, C8-C11 acyl lactylates, C6-C9 acyl methyl taurates, C6-C9 acyl isethionates, C6-C11 fatty acid soaps, C6-C9 alkyl sulphates, C6-C11 acyl sarcosinates, C6-C9 alkyl
  • a long-chain anionic surfactant chosen from C13-C18 alkyl ether sulphates, C13-C18 acyl lactylates, C13-C16 acyl methyl taurates, C13-C15 acyl isethionates, C13-C16 alkyl sulphates, C13-C16 acyl sarcosinates, C13-C16 alkyl sulphosuccinates, C13- C16 alkyl ether sulphosuccinates, or mixtures thereof; (c) optionally, a medium-chain anionic surfactant chosen from C10-C12 alkyl ether sulphates, C12 acyl lactylates, C10-C12 acyl methyl taurates, C10-C12 acyl isethionates, C10-C12 al
  • the present preservative/antimicrobial system is useful at any locus subject to contamination by bacteria, fungi, yeast or algae; for the preservation of agrochemical compositions, personal care products such as cosmetics, deodorants, contact lens products, as a disinfection for use, e.g., on human or animal skin, hair, oral cavity, mucous membranes, wounds, bruises or in the eye; for incorporation in cleaning compositions; and for disinfection of hard surfaces such as cleaning.
  • the present invention is directed to a preservative/antimicrobial system having an effective pH range of 4.5-7 comprising a blend of lactylates of the general formula:
  • a) 20-80 wt.%, preferably 60-70 wt% of the blend comprises a lactylate wherein R1 represents an C7 alkyl or alkenyl chain which may be branched or unbranched, and
  • b) 20-80 wt.% preferably 25-50 wt%, most preferably 27-45wt% of the blend comprises a lactylate wherein R1 represents an C9 alkyl or alkenyl chain which may be branched or unbranched, and c) 1 -30 wt. %, preferably 2-15 wt%, more preferably 9-12 wt% of the blend comprises a lactylate wherein R1 represents an C11 alkyl or alkenyl chain which may be branched or unbranched.
  • the present disclosure is also directed to a preservative/antimicrobial system according to the general formula wherein n is 1 and/or 2 in either one of the groups of lactylates falling within the definition of a), b), and c).
  • the present disclosure is also directed to a preservative/antimicrobial system according to the general formula wherein the ratio a/b/c between the amounts in weight of lactylates falling within the definition of a., b., and c., respectively, is in the range of 0.9-1.1 / 0.9-1.1 / 0.15-0.25.
  • the present disclosure is further directed to a preservative/antimicrobial system according to the general formula wherein additional conventional preservative is present, said preservative preferably chosen from sorbic acid or its salt, benzoic acid or its salt, dehydro acetic acid or its salt, ethyl hexyl glycerin, isothiazolinone or a combination hereof, most preferably sorbic acid or its salt or dehydro acetic acid is present.
  • sorbic acid or its salt preferably chosen from sorbic acid or its salt, benzoic acid or its salt, dehydro acetic acid or its salt, ethyl hexyl glycerin, isothiazolinone or a combination hereof, most preferably sorbic acid or its salt or dehydro acetic acid is present.
  • sorbic acid or its salt preferably chosen from sorbic acid or its salt, benzoic acid or its salt, dehydro acetic acid or its salt, ethyl
  • the present disclosure is directed to a low surfactant system comprising the preservative/antimicrobial system and containing between 0 and at maximum 4wt% of additional conventional preservative.
  • additional preservative is as low as possible and at or below 3 wt%, or at or below 2 wt% or even approaching 1wt% or less
  • the present disclosure is directed to a high surfactant system comprising the preservative/antimicrobial system and containing between at minimum 4 wt% of additional conventional preservative,.
  • the present disclosure further pertains to a cleaning composition comprising the preservative/antimicrobial system, preferably in an amount of between 0.25- 2 wt%, based on the total weight of the cleaning composition.
  • Said cleaning composition may be an all-purpose cleaning composition or a dish washing composition, which optionally comprises further additives such as
  • the present disclosure further pertains to an agrochemical composition
  • an agrochemical composition comprising the preservative/antimicrobial system, preferably in an amount of between 0.25- 2 wt%, based on the total weight of the agrochemical composition.
  • the present disclosure further pertains to a personal care composition
  • a personal care composition comprising the preservative/antimicrobial system according to the disclosure, preferably in an amount of between 0.25- 4 wt%, preferably 0.5-2 wt% based on the total weight of the personal care composition.
  • Said personal care composition may be a personal care cleaning composition or a personal care treatment composition.
  • the personal care composition may comprise additional additives such as
  • the present disclosure further pertains to a method for prolonging shelf-life of a composition wherein between 0.25-4 wt%, preferably 0.5-2 wt%, of the
  • preservative/antimicrobial system is added to the composition, based on the total weight of the composition.
  • Said composition may be a cleaning composition, an agrochemical composition, a personal care composition, a personal care treatment composition, a personal care cleaning composition, an ink or a coating.
  • the present disclosure is also directed to a method reducing microbial growth, and a method for preventing germination or spore-forming comprising treating the microbial cells with a composition comprising the preservative/antimicrobial system according to the disclosure.
  • the present disclosure is also directed to a method for cleaning, disinfecting or inhibiting microbial growth on a locus comprising contacting the locus with a composition comprising the preservative/antimicrobial system according to the present disclosure.
  • the present disclosure further pertains to the use of the preservative/antimicrobial system according to the disclosure in a cleaning composition, and agrochemical composition or a personal care composition, preferably a body cleaning composition, more preferably a skin cleaning composition or a hair cleaning composition.
  • the present disclosure further pertains to the use of the preservative/antimicrobial system according to the disclosure in a body treatment composition, preferably a skin treatment composition and/or a hair treatment composition.
  • the present invention is directed to a preservative/antimicrobial system having an effective pH range of 4.5-7 comprising a blend of lactylates of the general formula:
  • a) 20-80 wt.%, preferably 60-70 wt% of the blend comprises a lactylate wherein R1 represents an C7 alkyl or alkenyl chain which may be branched or unbranched, and
  • R1 represents an C11 alkyl or alkenyl chain which may be branched or unbranched.
  • Acyl lactylates are esters of fatty acids and (poly) lactic acid.
  • an ester may be obtained via, for example, an esterification or enzymatic process.
  • most processes for the manufacture of fatty acid esters result in a mixture of fatty acid esters whereby said mixture is for example a mixture of fatty acid esters of different fatty acid tails or of different ester tails.
  • a specific fatty acid in its pure form may be obtained out of this mixture by various means that are well-known to the person skilled in the art.
  • the fatty acid reactant may be a saturated or unsaturated fatty acid comprising 4 to 18 and preferably 6 to 18 carbon atoms.
  • C8 fatty acid reactants e.g. octanoic acid
  • C10 fatty acid reactants e.g. decanoic acid
  • C12 fatty acid reactants e.g.
  • dodecanoic acid are present.
  • the lactic acid may comprise of one monomer or several monomers of lactic acid linked to each other by polymerized bonds.
  • salts of said (poly) lactic acid are also very suitable for the
  • lactylates may comprise up to 6 lactic acid units. This is depicted in the formula as n.
  • lactic acid or lactide to form monolactylates or dilactylates respectively, is preferred.
  • preservation/antimicrobial system could be used at a lower dose rate and/or a lower dose of conventional preservatives or antimicrobial agents may be used or may even make the use of other preservative or antimicrobial agents superfluous.
  • lactylates both has a preservative activity and antimicrobial activity.
  • a preservative system protects the product from spoiling, extents shelf life and protects the consumer from getting ill from a contaminated (spoiled) product. It is for instance used in home and personal care products, food, agrochemical products, ink, coatings.
  • An antimicrobial system protects the consumer from germs by killing them.
  • these are used in home care and l&l cleaners (hygienic clean all-purpose cleaners, toilet bowl cleaners, wipes, floor cleaners, kitchen cleaner, and more) but can also be personal care deodorant, body washes, hand soaps, teat dips for cattle, anti-acne facial cleansers, tooth paste and more. It can also be used in agrochemical products like antifungal / antiviral / antibacterial pesticide. These antimicrobial system- containing products almost always also contain a preservative.
  • the preservative/antimicrobial system according to the present description has an effective pH range of between 4.5-7. This means that the system according to the description can be effectively used in compositions that have a pH value pH 4.5 to pH 7.
  • Adjustment of pH can be achieved by addition of a pH adjustant as conventionally used in the cosmetics art.
  • lactylates comprising 2 polymerized/esterified lactic acid molecules.
  • the lactylate components are often obtained as mixtures of for example a mixture of predominantly
  • lactylates may be obtained in their pure form (e.g. only the mono-form) by means of for example chromatographic separation or by any other means known to the person skilled in the art.
  • a high surfactant system is one wherein the total weight of surfactant and preservative/antimicrobial system in the final composition is at least 4 wt%. It usually comprises between 4- 40wt% of surfactant and preservative/antimicrobial system. This is the case in for instance, dish washing compositions, shampoos, liquid soap applications as for example body wash or hand soap compositions, rinse-off personal care
  • a low surfactant system is one wherein the total weight of surfactant and preservative/antimicrobial system in the final composition is at or below 4 wt%. This is the case in for instance leave-on personal care compositions and highly aqueous rinse-off personal care compositions comprising more than 85 % water, and in so- called ready-to-use applications such as for example low concentrated or ready to use agrochemical compositions, and ready-to-use wipes.
  • the amount of surfactant could be reduced by a same amount and even further. Addition of for example 0.25 wt% of the preservative/antimicrobial system of the present invention led to a minimal reduction of the total amount of surfactant with 0.25wt%. In low surfactant systems it was observed that the amount of surfactant could be lowered to about or below 3.5 wt% or to and below 3wt%, and even to and below 2 wt%. In the applications for home and personal care, the surfactant in the low surfactant systems could be lowered to about or below 0.1 wt%, more preferably to or below 0.75 wt% and most preferably to or below 0.5 or 0.35 wt%.
  • the amount of additional conventional preservative could also be reduced by addition of the preservative/antimicrobial system of the present invention.
  • the amount of additional conventional preservative was found possible to be reduced by 25% and even 50 to 60% to reach similar preservative and
  • the additional preservative is added in amounts of at maximum 0.4 wt% and more preferably at or below 0.2 or 0.1 wt%.
  • the additional conventional preservative is at max 0.08 wt%, at 0.05 wt% or even below 0.05 wt%, or completely omitted or lowered to such low quantities that it does not need to be registered on the label of the final consumer product.
  • additional conventional preservative is still added in above-mentioned quantities, this is mainly because a broader antimicrobial or preservative scope is desired (i.e. becoming effective against more different fungi, yeasts and/or bacteria) or the preservative and/or antimicrobial effect is to be further increased compared to the effect that the originally added amount of additional conventional preservative was showing.
  • the amount of additional surfactant may be lowered to between 0.006-0.75 wt%, preferably to 0.4 wt% or below, even more preferably to 0.2 wt% or below.
  • the lactylate composition was found to have a boosting effect in combination with conventional preservatives.
  • the currently used preservatives such as benzoic acid and salt, sorbic acid and salt, propionic acid and salt, phenoxyethanol, parabens, dehydroactic acid and salt, capryl hydroxamic acid and salt, anisic acid and salt, C6-C14 fatty acids and salts, lactic acid, isothiazolinones, quatermonium compounds.
  • the currently used preservatives such as benzoic acid and salt, sorbic acid and salt, propionic acid and salt, phenoxyethanol, parabens, dehydroactic acid and salt, capryl hydroxamic acid and salt, anisic acid and salt, C6-C14 fatty acids and salts, lactic acid, isothiazolinones, quatermonium compounds.
  • preservatives chosen from sorbic acid or its salt, benzoic acid or its salt, dehydro acetic acid or its salt, ethyl hexyl glycerin or a combination hereof, most preferably sorbic acid or its salt and dehydro acetic acid were found suitable to be used in combination with the lactylates according to the present description.
  • the fact that the preservative/antimicrobial system enables the use of lowered dose levels is especially an advantage when said conventional preservative is sorbic acid.
  • Sorbic acid is a relatively inexpensive and active preservative, but it is not readily dosed because it is a powder with a relatively low solubility. Sorbic acid powder is difficult to handle and dose and not the safest material to process.
  • sorbic acid or sorbate is being applied at all, it is added as one of the last ingredients to the final formulation. It is added to for example the final shampoo formulation and not to the surfactant system that is made up for the shampoo formulation. The possibility to use a lower dose and still ensure preservative action by application of the
  • preservative/antimicrobial system of the present invention facilitates the use of sorbic acid in liquid compositions.
  • the sorbic is in its
  • sorbic acid both (undissociated) sorbic acid is meant and (dissociated) sorbate. It was actually found that the problem of using sorbic acid is solved by creating sorbate/lactate solutions or by dissolving sorbic acid and/or sorbate into the lactylate preservative/antimicrobial system according to the present invention. Thus, by using lactate or the lactylate blend of the present invention sorbic acid and/or sorbate may be used as additional preservative in both low surfactant and high surfactant systems as described in the previous paragraphs.
  • the sorbate may be any mineral salt but preferably potassium or sodium sorbate salt or a mixture hereof.
  • the lactate may be any salt but preferably potassium or sodium lactate is applied or a mixture hereof.
  • a new invention thus is directed to a formulation comprising lactate and sorbate, and most preferably the sodium or potassium salts of lactate and sorbate and/or mixtures hereof.
  • the final concentration of sorbic acid and/or sorbate in a lactate solution may be 20 wt% or higher and preferably 30wt% or higher and most preferably 35 or 40%. When added to a high or low surfactant system, the sorbate is present in
  • the present invention further encompasses a formulation of sorbic acid and/or sorbate and the lactylate compositions as described previously in this application with optionally some further lactic acid present.
  • the final concentration of sorbic acid and/or sorbate in a lactylate preservative/antimicrobial system of the present invention may be 0.01 wt% or higher and preferably 0.025wt% or higher and most preferably between 0.025 and 0.075wt%.
  • sorbic acid and/or sorbate is present in concentrations of about 0.005 - 0.75 and more preferably in 0.01 - 0.40 wt% when combined with 0.1 - 4 wt% and more preferably 0.25 - 2 wt% of the lactylate blend compositions as mentioned previously.
  • the invention encompasses a method for dosing sorbic acid and/or sorbate into formulations for preservative and/or antimicrobial purposes and into the applications described in this disclosure_by combining the sorbic acid and/or sorbate with one or more lactate salts or with the lactylate preservative/antimicrobial system of the present invention or with a mixture of lactate and
  • preservative/antimicrobial system wherein further optionally some lactic acid may be present.
  • sorbic acid and/or sorbate were in particular found to be very effective in inhibiting fungal growth in non-sterile situations (like for example open bottles or containers at customers) and in preventing fungal growth in closed bottles with very few specimen present.
  • the preservation/antimicrobial system comprising the lactylate blend according to the present invention and sorbic acid was found to be effective on a broad scope of microorganisms including fungi and bacteria while the preservation/antimicrobial systems as known in literature have not been found that effective over such a broad scope of microorganisms and usually target only fungi or only bacteria or may be both but then with a much lower efficacy resulting still in growth of one or the other type of microorganism when used in conventional concentrations.
  • lactylate formulations of the present invention prevents the use of such high concentrations and is still effective against both fungi and bacteria while maintaining an acceptable organoleptic profile of the end consumer product and the combination with sorbic acid even further improves this effect.
  • the preservative/antimicrobial system can be used in cleaning compositions in which they reduce or completely inhibit growth or kill microorganisms present at the surface of the object to be cleaned or treated. Since the lactylates also have surfactant properties it further helps to remove spores, germs and other residual contaminant material from the surface. Said cleaning composition may be added to water or other solvent, directly used on a cloth, or may be provided on ready-to-use wipes. The preservative/antimicrobial system can also be used to prevent deterioration of the compositions in which they are used.
  • the preservation/antimicrobial system can be used in cleaning composition comprising the preservative/antimicrobial system, preferably in an amount of between 0.25- 4 wt%, preferably 0.5-2 wt%, based on the total weight of the cleaning composition.
  • Cleaning compositions usually comprise high surfactant systems such as in manual dish wash compositions, and all-purpose cleaners. These cleaning compositions may be used for cleaning surfaces and cooking utensils in food processing plants and in areas in which food is prepared or served such as hospitals nursing homes, restaurants or at home, such as all-purpose cleaners, manual dish washing compositions, disinfective cleaners and sprays and the like.
  • other conventional components for cleaning compositions may be present such as detergent, surfactants, surface active agent.
  • the present disclosure further pertains to an agrochemical composition
  • an agrochemical composition comprising the preservative/antimicrobial system, preferably in an amount of between 0.25- 4 wt%, preferably 0.5-2 wt%, based on the total weight of the agrochemical
  • agrochemical composition may be in the form of a dilutable concentrate (DC), emulsifiable concentrate (EC), suspension concentrate (SC), capsule suspension (CS), oil in water (EW), oil dispersion (OD).
  • DC dilutable concentrate
  • EC emulsifiable concentrate
  • SC suspension concentrate
  • CS capsule suspension
  • EW oil in water
  • OD oil dispersion
  • Concentrated agrochemical compositions usually are high surfactant systems, while ready-to-use agrochemical compositions usually are low surfactant systems.
  • Common other components in agrochemical compositions are:
  • solvents for the actives preferably“green” solvents such as natural vegetable oils, long chain aliphatic carboxylic acids, triglyceride esters and methylated vegetable oils,
  • surfactants such as anionic, cationic, nonionic and amphoteric surfactants - freeze/thaw additive
  • preservative/antimicrobial system may also be used in addition to other, conventional, preservatives, since the lactylate composition was found to have a boosting effect in combination with conventional preservatives. This may support the lowered dose-levels of the currently used preservatives such as benzoic acid and salt, sorbic acid and salt, propionic acid and salt, phenoxyethanol, parabens, dehydroacetic acid and salt, capryl hydroxamic acid and salt, anisic acid and salt, C6-C14 fatty acids and salts, lactic acid, isothiazolinones, quatermonium compounds
  • the preservative/antimicrobial system according to the present description can be used in personal care composition comprising the preservative/antimicrobial system, preferably in an amount of between 0.25- 4 wt%, preferably 0.5-2 wt%, based on the total weight of the personal care composition.
  • Said personal care composition may be a personal care cleaning composition or a personal care treatment composition.
  • These personal care compositions can, for example, include skin creams, lotions, milks and powders, skin cleansing products, hair treatment products, such as shampoos, conditioners, styling aids and dental products, such as toothpastes and mouthwashes.
  • Personal care cleaning composition can be applied topically in the form of ointments, solutions, gels or any other cosmetically acceptable type of composition. They may be formulated for washing the hair or skin, for example, hair shampoos; rinse-off hair care products; bath or shower gels; and facial washing compositions. Said personal cleaning composition may also may be provided on ready-to-use wipes.
  • personal care cleaning compositions may comprise surfactants, solvents (usually water), structurants such as swelling clays, fatty acids and polyglycol-ethers, thickeners, opacifiers, plant extracts, colourants, cationic surfactant, and perfumes.
  • the acyl lactylates are usually employed in a cosmetically acceptable vehicle. They are usually formulated as leave-on
  • Rinse-off formulations usually are high surfactant systems, while leave-on formulations usually are low surfactant compositions.
  • Vehicles other than water can include liquid or solid emollients, solvents, humectants, thickeners and powders.
  • Emollients such as stearyl alcohol, glyceryl monoricinoleate, mink oil, cetyl alcohol, isopropyl isostearate, stearic acid, isobutyl palmitate, isocetyl stearate, oleyl alcohol, isopropyl laurate, hexyl laurate, decyl oleate, octadecan-2-ol, isocetyl alcohol, eicosanyl alcohol, behenyl alcohol, cetyl palmitate, silicone oils such as dimethylpolysiloxane,di-n-butyl sebacate, isoporpyl myristate, isopropyl palmitate, isopropyl stearate, butylstearate, polyethylene glycol, triethylene glycol, lanolin, cocoa butter, corn oil, cotton seed oil, olive oil, palm kernel oil, rapeseed oil, safflower seed oil, evening primrose oil
  • Solvents such as ethyl alcohol, methylene chloride, isopropanol, acetone, ethylene glycol monoethyl ether, diethylene glucol monobutyl ether, diethylene glycol monoethyl ether, dimethyl sulphoxide, dimethyl formamide,
  • Powders such as chalk, talc, fullers earth, kaolin, starch, gums, colloidal silica sodium polyacrylate, tetraalkyl and/or trialkyl aryl ammonium smectites, chemically modified magnesium aluminium silicate, organically modified montmorillonite clay, hydrated aluminium silicate, fumed silica, carboxyvinyl polymer, sodium carboxymethylcellulose, ethylene glycol monostearate.
  • colloidal silica sodium polyacrylate such as chalk, talc, fullers earth, kaolin, starch, gums, colloidal silica sodium polyacrylate, tetraalkyl and/or trialkyl aryl ammonium smectites, chemically modified magnesium aluminium silicate, organically modified montmorillonite clay, hydrated aluminium silicate, fumed silica, carboxyvinyl polymer, sodium carboxymethylcellulose, ethylene glycol monostearate.
  • Emulsion ingredients are present if the composition for the use according to the invention is in the form of an emulsion in which case an oil or oily material will normally be present, together with an emulsifier to provide either a water- in-oil emulsion or an oil-in-water emulsion.
  • suitable oils and oily materials include mineral oil, vegetable oils, silicone oils, both volatile and non volatile, such as polydimethyl siloxanes.
  • the oil or oily material when present for the purposes for forming an emulsion will normally form up to 90%, preferably from 10 to 80% by volume of the composition.
  • the amount of the emulsifier or mixtures thereof will normally be from 1 to 50%, preferably from 2 to 20% and most preferably from 2 to 10% by weight of the composition.
  • the composition can also comprise of water, usually up to 80%, preferably from 5 to 80% by volume.
  • surfactants such as anionic, non-anionic, cationic or amphoteric surfactants or mixtures thereof may be present, particularly when the composition is intended for shampooing the hair or for use when bathing or in the shower.
  • the surfactants form from 2 to 40 % by weight and preferably from 5 to 30 % by weight.
  • the presence of surfactants is usually kept low, generally lower than 4 wt%, to avoid the risk of irritation of the skin.
  • Suitable surfactants are sodium lauryl sulfate, sodium laureth sulfate, APG, quats, CAP B, etcetera.
  • quats that have shown to work well in combination with the present invention may be ADEBAC (C12-14- alkyl [(ethylphenyl) methyl] dimethyl chlorides), ADBAC (Benzyl C12-16 alkyl dimethyl chlorides), DDAC (Didecyldimethylammonium chloride) and/or combinations hereof.
  • Hydrophylic components may be present to help solubilize and/or physically stabilize the lactylates in the composition and/or to enhance the antimicrobial efficacy and/or the speed of antimicrobial efficacy.
  • hydrophilic components include, but are not limited to, water, polyhydric alcohols, lower alkyl ethers (i.e., having a sufficiently small number of carbon atoms to meet the solubility limit above), N- methylpyrrolidone, alkyl esters (i.e., having a sufficiently small number of carbon atoms to meet the solubility limit above), and the lower monohydroxy alcohols.
  • the hydrophilic components include polyhydric alcohols, lower alkyl ethers, and short chain esters. More preferably, the hydrophilic components include polyhydric alcohols.
  • composition Adjuncts which include for instance antioxidants, such as butyl hydroxy toluene; humectants such as glycerol, sorbitol; buffers such as lactic acid or sodium hydroxide; waxes such as beeswax, paraffinwax;
  • moisturizers such as aloa vera
  • UV- absorbers vitamins, anti oxidants, thickeners
  • colourants such as kaolin, kaolin, kaolin, kaolin, kaolin, kaolin, kaolin, kaolin, kaolin, kaolin, kaolin, kaolin, kaolin, kaolin, kaolin, kaolin, kaolin, kaolin, kaolin, kaolin, kaolin, FD&C Red No., FD&C Red No., FD&C Red No., FD&C Red No., FD&C Red No., FD&C Red No., FD&C Red No., FD&C Red No., FD&C Red No., FD&C Red No., FD&C Red No., FD&C Red No., FD&C Red No., FD&C Red No., FD&C Red No., FD&C Red No., FD&C Red
  • the preservative/antimicrobial system may also be used in addition to other, conventional, preservatives, since the lactylate composition was found to have a boosting effect in combination with conventional preservatives. This may support the lowering of dose-levels or even complete avoidance of use of the currently used preservatives such as benzoic acid and salt, sorbic acid and salt, propionic acid and salt, phenoxyethanol, parabens, dehydroacetic acid and salt, capryl hydroxamic acid and salt, anisic acid and salt, C6-C14 fatty acids and salts, lactic acid, isothiazolinones, quatermonium compounds.
  • benzoic acid and salt such as benzoic acid and salt, sorbic acid and salt, propionic acid and salt, phenoxyethanol, parabens, dehydroacetic acid and salt, capryl hydroxamic acid and salt, anisic acid and salt, C6-C14 fatty acids and salts, lactic acid, isothia
  • the cosmetically acceptable vehicle will usually form from 10 to 99.9%, preferably from 50 to 99% by weight of the composition, and can, in the absence of other cosmetic adjuncts, form the balance of the composition.
  • the acyl lactylates are also usually employed in cosmetically acceptable vehicle as described above for personal care cleaning compositions. They usually are formulated as leave-on formulation, i.e. as low surfactant system, but rinse-off formulations are also possible.
  • the personal care treatment composition can comprise specific cosmetic adjuncts such as organic sunscreen materials in an amount of from 0.1 to 20%, preferably from 1 to 10% by weight and/or Inorganic sunscreens, such as ultra fine titanium dioxide, dandruff treatment components, anti-acne agents, tanning agent, anti-wrinkle, anti-ageing agents and tooth paste components.
  • the personal care treatment compositions as defined above can also serve as a vehicle to distribute the acyl lactylates to areas such as the human skin, nails, hair or tooth which are affected by undesired microorganisms, in particular fungi.
  • the present description is also directed to a method for prolonging shelf-life of a composition wherein between 0.25-4 wt%, preferably 0.5-2 wt%, of a
  • preservative/antimicrobial composition according to claim 1 is added to the
  • composition based on the total weight of the composition.
  • Said composition may be a cleaning composition, an agrochemical composition, ink, a coating composition, personal care composition or a personal care cleaning composition.
  • Compositions that can suitably be preserved are for instance cosmetics, deodorants, contact lens products.
  • the present disclosure is also directed to a method for reducing microbial growth and a method preventing germination or inhibition of spore-forming, comprising treating the microbial cells with a composition comprising the preservative/antimicrobial system according to the disclosure.
  • Said microbial cells may be present in any composition that is susceptible to microbial contamination by bacteria, fungi, yeast or algae.
  • the present disclosure is also directed to a method for cleaning, disinfecting or inhibiting microbial growth on a locus comprising contacting the locus with a composition comprising the preservative/antimicrobial system according to the present disclosure.
  • cleaning is also meant: removal of contaminants such as germs and spores.
  • Said locus may be any hard surface, but also human or animal skin, hair, oral cavity, mucous membranes, wounds, bruises or in the eye may be disinfected with the preservative/antimicrobial system according to the present disclosure.
  • the present disclosure further pertains to the use of the preservative/antimicrobial system according to the disclosure in a cleaning composition or a personal care composition, preferably a body cleaning composition, more preferably a skin cleaning composition or a hair cleaning composition, a body treatment composition, preferably a skin treatment composition and/or a hair treatment composition.
  • a cleaning composition or a personal care composition preferably a body cleaning composition, more preferably a skin cleaning composition or a hair cleaning composition, a body treatment composition, preferably a skin treatment composition and/or a hair treatment composition.
  • BSA Bovine Albumin Serum
  • Candida Albicans AB stands for Aspargillus Brasilliensis ; a minus (-) indicates that no significant reduction of the microorganisms took place, a plus (+) indicated that for bacteria more than log 5 reduction took place and for fungi that more than log 4 reduction took place, and a plus-minus (+/-) indicates that for bacteria a reduction of between log 3 to log 5 took place and for fungi that a reduction of between log 2.5 and log 4 took place.
  • lactylate compositions were bioscreened. All samples contained: 0.25 wt% APG (Alkyl polyglycoside) and 0.01 wt % yeast extract. The pH was set to 5.5 and 6.5 with NaOH or HCI.
  • the samples further contained C6 or C8 or C10 or C12 lactylate or mixtures hereof in concentrations that were varied between 0 (bianco) and about 1.2 wt% at pH 5.5 and 6.5 as indicated in Table II.
  • the plates were placed in a bioscreen machine 30 °C, filter 420-580 nm, and followed for 21 days with every 6 hrs being measured for optical density (OD) using a filter of 420-580 nm. Increase of OD in time meant growth of cells.
  • composition of the lactylate formulation is the composition of the lactylate formulation:
  • the preservative/antimicrobial system of the present invention is able to reduce growth faster than the conventional preservatives and thereby prevent the concentration of cells to become that high that the added dose of preservative/antimicrobial system is too low to have sufficient effect. This further prevents (re)contamination due to the customer (re-) opening the package.

Abstract

The present invention is directed to a preservative/antimicrobial system having an effective pH range of 4.5-7 comprising: a. 20-80 wt.% of C8 lactylate, preferably 60-70 wt%, b. 20-80 wt.% of C10 lactylate, preferably 25-50 wt%, and c. 1 -30 wt. % of C12 lactylate, preferably 2-15 wt%. This preservative/antimicrobial system can suitably be used in cleaning compositions, agrochemical compositions, and personal care compositions such as personal care cleaning compositions and personal care treatment compositions. It was found that this preservative/antimicrobial system is so effective that it can be used in relatively low doses such as between 0.25 wt% to 4, preferably between 0.5-2 wt%.

Description

LACTYLATE BLEND FOR PRESERVATIVE/ANTIMICROBIAL SYSTEM
Field
The present invention relates to a preservative/antimicrobial system, a cleaning composition and personal care composition comprising said
preservative/antimicrobial system, a method for preservation, a method for killing microbial cells and the use of said preservative/antimicrobial system in cleaning, personal care, agrochemical products, inks and coatings.
Current preservative/antimicrobial systems are getting more under pressure by law. Some are not allowed anymore, and the trend is that regulations demand lower dose levels due to environmental problems, skin irritation and bacterial resistance. At lower dose levels most preservatives/antimicrobials do not perform well anymore. For this problem there is a market need for new preservatives/antimicrobials or preservative boosters.
Background
It is well known that the presence and the growth and proliferation of many bacteria, moulds, mildews and yeasts is undesired in many locations because of deterioration of the materials concerned, toxicological hazards, disease causing factors and similar considerations. For instance, personal care products, agrochemicals and cleaning products may be subject to deterioration or spoilage because of growth of such microorganisms. Furthermore, most skin diseases can be caused or initiated by the presence of bacteria but also by specific types of fungi. Compositions that deteriorate or spoil as a result of the presence and the growth of microorganisms can have a very short shelf life, that is the period during which they can usefully be employed, unless they are refrigerated, frozen or sterilized within a sealed container. For compositions which are intended for occasional or regular use by the consumer, for example as cleaning products, agricultural products, beauty products or cleansing products for the skin, hair or teeth, it is inconvenient to maintain them under refrigerated conditions, and normally impossible to prevent contamination by
l adventitious microorganisms, particularly yeast, moulds and bacteria, of an otherwise sterile product, once the packaging that maintains sterility is opened.
In order to prevent microbial spoilage of such products, it has hitherto been necessary to incorporate a preservative chemical, such as 2-bromo-2-nitropropane- 1 ,3-diol (Bronopol), methyl paraben or other commonly used preservatives such as isothiazolinones, phenoxy ethanol, parabens, acids and its salts (like lactic, sorbic, benzoic). As research into the merits or demerits of using conventional preservative chemicals progresses, there is an increasing realization that some of these chemicals can themselves deteriorate on storage, so that their preservative benefits diminish or are lost, or they can decompose in the product with the formation of bi-products that can be harmful to health. Furthermore, as indicated above the conventional preservative systems are getting more and more under pressure by law, and regulations demand lower dose levels.
It is known that some lactylates show efficacy against certain specimen, however the individual lactylates were found not to be effective against a full spectrum of bacteria, yeasts, fungi and moulds.
For instance, in WO 2009/037269 an antibacterial composition is disclosed based on a combination of fatty acid ester of fatty acid and hydroxy carboxylic acid with an antibacterial agent selected from polylysine, protamine, their salts and mixtures hereof. The hydroxy carboxylic acid may be present as acid in its free form, in its salt form and/or in its ester form. The publication is further directed to the use of said composition as antibacterial agent against gram-negative bacteria in various products, applications and methods. Furthermore, the invention is related to products comprising said antibacterial agent. In the examples only C10-C14 lactylates are used either alone or in combination with polylysine.
WO 98/22086 describes an aqueous cleansing composition suitable for claiming human skin and hair, which comprises:
(a) a short-chain anionic surfactant chosen from C6-C9 alkyl ether sulphates, C5-C11 acyl lactylates, C6-C9 acyl methyl taurates, C6-C9 acyl isethionates, C6-C11 fatty acid soaps, C6-C9 alkyl sulphates, C6-C11 acyl sarcosinates, C6-C9 alkyl sulphosuccinates, C6-C9 alkyl ether sulphosuccinates, or mixtures thereof; (b) a long-chain anionic surfactant chosen from C13-C1 s alkyl ether sulphates, C13- C1 s acyl lactylates, C13-C16 acyl methyl taurates, C13-C15 acyl isethionates, C13- C16 alkyl sulphates, C13-C16 acyl sarcosinates, C13-C16 alkyl sulphosuccinates, C13-C16 alkyl ether sulphosuccinates, or mixtures thereof;
(c) optionally, a medium-chain anionic surfactant chosen from C10-C12 alkyl ether sulfates, C12 acyl lactylates, C10-C12 acyl methyl taurates, C10-C12 acyl
isethionates, C10-C12 alkyl sulphates, C12 acyl sarcosinates, C10-C12 alkyl sulphosuccinates, C10--C12 alkyl ethersulphosuccinates, or mixtures thereof, and (d) water; wherein (i) at least one of the surfactants (a) and (b) is selected from the group consisting of the acyl lactylates, the acyl sarcosinates, the acyl methyl taurates, the alkyl ether sulphates and the acyl isethionates, or the short-chain anionic surfactant
(a) is a C6-C11 fatty acid soap; (ii) if surfactant (c) is present, then the surfactants (a),
(b) and (c) are present
in an amount such that the weight ratio of (c): [(a) + (b)] is less than 1 :1.
EP 0572271 discloses the use of acyl lactylate as antimicrobial actives, that is to inhibit or prevent the growth of micro-organisms or to reduce the amount of micro organisms present. In the publication only single acyl acrylates such as hexanoyl lactylate octanoyl lactylate and a 50/50 mixture of sodium capryl/sodium lauryl lactylate are used.
In WO 2009/092787 the use of lactylate or glycolate for preventing or treating intestinal infections caused by gram-positive bacteria in animals such as Clostridia is disclosed.
WO 2002/08377 discloses an antimicrobial composition comprising an enzymatic component and one or more non-enzymatic biocides; a method for killing or inhibiting microbial cells comprising a treatment with the antimicrobial composition and a detergent composition comprising the antimicrobial composition.
WO 2009/037274 is directed to a method for preserving acidic beverages having a pH of or below 4.8 against fungi, yeasts and bacteria. Said preservation method comprises the application of a composition based on polylysine and/or a salt hereof in combination with a second preservative agent selected from glyceride and/or fatty acid ester of hydroxycarboxylic acid in its acidic, salt or ester form. The use of C6- C18 lactylates is preferred and the combination of C12 and C14 lactylates is specifically mentioned.
US 2006/0051384 discloses antimicrobial compositions, especially those useful when applied topically to tissue, such as mucosal tissues (i.e. , mucous membranes), that include an antimicrobial selected from the group consisting of peroxides, C6-C14 alkyl carboxylic acids, C6-C14 alkyl carboxylate ester carboxylic acids, C8-C22 mono- or polyunsaturated carboxylic acids, and antimicrobial natural oils. The compositions can also include an enhancer component, a surfactant, a hydrophobic component, and/or a hydrophilic component. Such compositions provide effective topical antimicrobial activity and are accordingly useful in the treatment and/or prevention of conditions that are caused, or aggravated by, microorganisms.
US 2005/053593A is generally related to a product and process to reduce the microbial contamination on organic matter, such as processed meat, fruits and vegetables, plant parts, inanimate surfaces such as textiles and stainless steel, and in the mouth or on dental products. In particular, the invention is related to a product and process to disinfect surfaces using an antimicrobial composition containing an antimicrobial lipid, an enhancer selected from the group consisting of bacteriocins, antimicrobial enzymes, sugars, sugar alcohols, iron-binding proteins and derivatives thereof, siderophores, and combinations thereof, and optionally a surfactant. The compositions may optionally also contain a surfactant (i.e., one or more surfactants). Suitable surfactants include acyl lactylate salts, dioctyl sulfosuccinate salts, lauryl sulfate salts, dodecylbenzene sulfonate salts, and salts of (C8-C18) fatty acids.
US 6001787 discloses an aqueous cleansing composition, which comprises: (a) a short-chain anionic surfactant chosen from C6-C9 alkyl ether sulphates, C8-C11 acyl lactylates, C6-C9 acyl methyl taurates, C6-C9 acyl isethionates, C6-C11 fatty acid soaps, C6-C9 alkyl sulphates, C6-C11 acyl sarcosinates, C6-C9 alkyl
sulphosuccinates, C6-C9 alkyl ether sulphosuccinates, or mixtures thereof; (b) a long-chain anionic surfactant chosen from C13-C18 alkyl ether sulphates, C13-C18 acyl lactylates, C13-C16 acyl methyl taurates, C13-C15 acyl isethionates, C13-C16 alkyl sulphates, C13-C16 acyl sarcosinates, C13-C16 alkyl sulphosuccinates, C13- C16 alkyl ether sulphosuccinates, or mixtures thereof; (c) optionally, a medium-chain anionic surfactant chosen from C10-C12 alkyl ether sulphates, C12 acyl lactylates, C10-C12 acyl methyl taurates, C10-C12 acyl isethionates, C10-C12 alkyl sulphates, C12 acyl sarcosinates, C10-C12 alkyl sulphosuccinates, C10-C12 alkyl ether sulphosuccinates, or mixtures thereof, and (d) water; wherein (i) at least one of the surfactants (a) and (b) is selected from the group consisting of the acyl lactylates, the acyl sarcosinates, the acyl methyl taurates, the alkyl ether sulphates and the acyl isethionates, or the short-chain anionic surfactant (a) is a C6-C11 fatty acid soap; (ii) if surfactant (c) is present, then the surfactants (a), (b) and (c) are present in an amount such that the weight ratio of (c):[(a)+(b)] is less than 1 :1.
We have found that a mixture of specific lactylates in specific ratios is a very suitable preservative/antimicrobial system. The present preservative/antimicrobial system is useful at any locus subject to contamination by bacteria, fungi, yeast or algae; for the preservation of agrochemical compositions, personal care products such as cosmetics, deodorants, contact lens products, as a disinfection for use, e.g., on human or animal skin, hair, oral cavity, mucous membranes, wounds, bruises or in the eye; for incorporation in cleaning compositions; and for disinfection of hard surfaces such as cleaning.
Summary of the invention
The present invention is directed to a preservative/antimicrobial system having an effective pH range of 4.5-7 comprising a blend of lactylates of the general formula:
R1 -COO[-CH(CH3)-COO]n- H, wherein: n= between 1 and 6,
or a salt of the compound according to the general formula and wherein:
a) 20-80 wt.%, preferably 60-70 wt% of the blend comprises a lactylate wherein R1 represents an C7 alkyl or alkenyl chain which may be branched or unbranched, and
b) 20-80 wt.% preferably 25-50 wt%, most preferably 27-45wt% of the blend comprises a lactylate wherein R1 represents an C9 alkyl or alkenyl chain which may be branched or unbranched, and c) 1 -30 wt. %, preferably 2-15 wt%, more preferably 9-12 wt% of the blend comprises a lactylate wherein R1 represents an C11 alkyl or alkenyl chain which may be branched or unbranched.
The present disclosure is also directed to a preservative/antimicrobial system according to the general formula wherein n is 1 and/or 2 in either one of the groups of lactylates falling within the definition of a), b), and c).
The present disclosure is also directed to a preservative/antimicrobial system according to the general formula wherein the ratio a/b/c between the amounts in weight of lactylates falling within the definition of a., b., and c., respectively, is in the range of 0.9-1.1 / 0.9-1.1 / 0.15-0.25.
The present disclosure is further directed to a preservative/antimicrobial system according to the general formula wherein additional conventional preservative is present, said preservative preferably chosen from sorbic acid or its salt, benzoic acid or its salt, dehydro acetic acid or its salt, ethyl hexyl glycerin, isothiazolinone or a combination hereof, most preferably sorbic acid or its salt or dehydro acetic acid is present. Especially a preservative/antimicrobial system that fulfills the preferred ranges of the general formula in combination with sorbic acid or dehydroacetic acid was found very suitable.
Depending on the type of final use, i.e. in a high surfactant system or a low
surfactant system, the use of additional conventional preservative could be lowered or even omitted altogether
The present disclosure is directed to a low surfactant system comprising the preservative/antimicrobial system and containing between 0 and at maximum 4wt% of additional conventional preservative. Preferably the additional preservative is as low as possible and at or below 3 wt%, or at or below 2 wt% or even approaching 1wt% or less
The present disclosure is directed to a high surfactant system comprising the preservative/antimicrobial system and containing between at minimum 4 wt% of additional conventional preservative,. The present disclosure further pertains to a cleaning composition comprising the preservative/antimicrobial system, preferably in an amount of between 0.25- 2 wt%, based on the total weight of the cleaning composition.
Said cleaning composition may be an all-purpose cleaning composition or a dish washing composition, which optionally comprises further additives such as
surfactants, detergent, colorant and perfume.
The present disclosure further pertains to an agrochemical composition comprising the preservative/antimicrobial system, preferably in an amount of between 0.25- 2 wt%, based on the total weight of the agrochemical composition.
The present disclosure further pertains to a personal care composition comprising the preservative/antimicrobial system according to the disclosure, preferably in an amount of between 0.25- 4 wt%, preferably 0.5-2 wt% based on the total weight of the personal care composition. Said personal care composition may be a personal care cleaning composition or a personal care treatment composition.
The personal care composition may comprise additional additives such as
surfactants, detergent, colorant and perfume.
The present disclosure further pertains to a method for prolonging shelf-life of a composition wherein between 0.25-4 wt%, preferably 0.5-2 wt%, of the
preservative/antimicrobial system according to the disclosure is added to the composition, based on the total weight of the composition. Said composition may be a cleaning composition, an agrochemical composition, a personal care composition, a personal care treatment composition, a personal care cleaning composition, an ink or a coating.
The present disclosure is also directed to a method reducing microbial growth, and a method for preventing germination or spore-forming comprising treating the microbial cells with a composition comprising the preservative/antimicrobial system according to the disclosure.
The present disclosure is also directed to a method for cleaning, disinfecting or inhibiting microbial growth on a locus comprising contacting the locus with a composition comprising the preservative/antimicrobial system according to the present disclosure. The present disclosure further pertains to the use of the preservative/antimicrobial system according to the disclosure in a cleaning composition, and agrochemical composition or a personal care composition, preferably a body cleaning composition, more preferably a skin cleaning composition or a hair cleaning composition.
The present disclosure further pertains to the use of the preservative/antimicrobial system according to the disclosure in a body treatment composition, preferably a skin treatment composition and/or a hair treatment composition.
Detailed description
The present invention is directed to a preservative/antimicrobial system having an effective pH range of 4.5-7 comprising a blend of lactylates of the general formula:
R2-COO[-CH(CH3)-COO]n- H, wherein: n= between 1 and 6,
or a salt of the compound according to the general formula and wherein
a) 20-80 wt.%, preferably 60-70 wt% of the blend comprises a lactylate wherein R1 represents an C7 alkyl or alkenyl chain which may be branched or unbranched, and
b) 20-80 wt.% preferably 25-50 wt%, most preferably 27-45 wt% of the blend comprises a lactylate wherein R1 represents an C9 alkyl or alkenyl chain which may be branched or unbranched, and
c) 1 -30 wt. %, preferably 2-15 wt%, more preferably 9-12 wt%, of the blend
comprises a lactylate wherein R1 represents an C11 alkyl or alkenyl chain which may be branched or unbranched.
Thus, the present description describes a blend of acyl lactylates in a specific ratio.
Acyl lactylates are esters of fatty acids and (poly) lactic acid. As the person skilled in the art knows, such an ester may be obtained via, for example, an esterification or enzymatic process. As is common knowledge, most processes for the manufacture of fatty acid esters result in a mixture of fatty acid esters whereby said mixture is for example a mixture of fatty acid esters of different fatty acid tails or of different ester tails. A specific fatty acid in its pure form may be obtained out of this mixture by various means that are well-known to the person skilled in the art.
The fatty acid reactant may be a saturated or unsaturated fatty acid comprising 4 to 18 and preferably 6 to 18 carbon atoms. As is clear from the formula above, in the system according to the invention mainly C8 fatty acid reactants (e.g. octanoic acid), C10 fatty acid reactants (e.g. decanoic acid) and C12 fatty acid reactants (e.g.
dodecanoic acid) are present.
The lactic acid may comprise of one monomer or several monomers of lactic acid linked to each other by polymerized bonds.
Further, the salts of said (poly) lactic acid are also very suitable for the
preservative/antimicrobial system according to the present invention. The lactylates according to the description may comprise up to 6 lactic acid units. This is depicted in the formula as n. The use of lactic acid or lactide to form monolactylates or dilactylates respectively, is preferred.
It is known that some lactylates show efficacy against certain specimen, but not against a full spectrum. To reach the full spectrum the addition of other antimicrobial agents is necessary. We have now found that specific mixtures of lactylates with the ratios as described above gave better results than the single lactylates. Furthermore, the combined use of a mixture of lactylates in a specific ratio was found to be more effective than sum of the activities of the individual lactates. In other words, the blend of lactylates was found to work in synergy. As a result thereof, the
preservation/antimicrobial system according to the description could be used at a lower dose rate and/or a lower dose of conventional preservatives or antimicrobial agents may be used or may even make the use of other preservative or antimicrobial agents superfluous.
It was found that this specific blend of lactylates both has a preservative activity and antimicrobial activity. A preservative system protects the product from spoiling, extents shelf life and protects the consumer from getting ill from a contaminated (spoiled) product. It is for instance used in home and personal care products, food, agrochemical products, ink, coatings. An antimicrobial system protects the consumer from germs by killing them. Generally, these are used in home care and l&l cleaners (hygienic clean all-purpose cleaners, toilet bowl cleaners, wipes, floor cleaners, kitchen cleaner, and more) but can also be personal care deodorant, body washes, hand soaps, teat dips for cattle, anti-acne facial cleansers, tooth paste and more. It can also be used in agrochemical products like antifungal / antiviral / antibacterial pesticide. These antimicrobial system- containing products almost always also contain a preservative.
The preservative/antimicrobial system according to the present description has an effective pH range of between 4.5-7. This means that the system according to the description can be effectively used in compositions that have a pH value pH 4.5 to pH 7.
Adjustment of pH can be achieved by addition of a pH adjustant as conventionally used in the cosmetics art.
Components wherein n is for example 1 are referred to as monolactylates
(i.e.comprising only 1 lactic acid molecule) and wherein x is 2 are called dilactylates (comprising 2 polymerized/esterified lactic acid molecules). The lactylate components are often obtained as mixtures of for example a mixture of predominantly
monolactylates and further comprising dilactylates due to the way in which they are prepared. It may be very well possible that also higher polymerized lactylates are present in the mixture. The parameter n, as described above thus presents average number.
The lactylates may be obtained in their pure form (e.g. only the mono-form) by means of for example chromatographic separation or by any other means known to the person skilled in the art.
Good results were obtained with mixtures predominantly containing mono- and/or di- lactylate esters of octanoic acid (C8), and decanoic acid (C10), and dodecanoic acid (C12) and the sodium, potassium and calcium salts hereof.
It was found that ratio a/b/c between the amounts in weight of lactylates falling within the definition of a., b., and c., respectively, preferably is in the range of 0.9-1.1 / 0.9- 1.1 / 0.15-0.25. With these specific amounts of lactylates a synergetic effect was obtained.
As mentioned above, it was found that the preservative/antimicrobial system can be used both in high surfactant systems and in low surfactant systems. A high surfactant system is one wherein the total weight of surfactant and preservative/antimicrobial system in the final composition is at least 4 wt%. It usually comprises between 4- 40wt% of surfactant and preservative/antimicrobial system. This is the case in for instance, dish washing compositions, shampoos, liquid soap applications as for example body wash or hand soap compositions, rinse-off personal care
compositions, all-purpose cleaners, concentrated agrochemical compositions etcetera. A low surfactant system is one wherein the total weight of surfactant and preservative/antimicrobial system in the final composition is at or below 4 wt%. This is the case in for instance leave-on personal care compositions and highly aqueous rinse-off personal care compositions comprising more than 85 % water, and in so- called ready-to-use applications such as for example low concentrated or ready to use agrochemical compositions, and ready-to-use wipes.
In both systems it was found that by addition of a certain amount of the
preservative/antimicrobial system of the present invention, the amount of surfactant could be reduced by a same amount and even further. Addition of for example 0.25 wt% of the preservative/antimicrobial system of the present invention led to a minimal reduction of the total amount of surfactant with 0.25wt%. In low surfactant systems it was observed that the amount of surfactant could be lowered to about or below 3.5 wt% or to and below 3wt%, and even to and below 2 wt%. In the applications for home and personal care, the surfactant in the low surfactant systems could be lowered to about or below 0.1 wt%, more preferably to or below 0.75 wt% and most preferably to or below 0.5 or 0.35 wt%.
It was further found that at the same time when reducing the conventionally applied amount of surfactant, the amount of additional conventional preservative could also be reduced by addition of the preservative/antimicrobial system of the present invention. The amount of additional conventional preservative was found possible to be reduced by 25% and even 50 to 60% to reach similar preservative and
antimicrobial effects as with the conventional amount of preservative. Conventionally about or between 0.01 and 1 wt% of conventional preservative is used in both low and high surfactant systems and more often around 0.025 wt%. It was found that the use of additional conventional preservative in low surfactant systems could be lowered to 0-0.75 wt% of the total preservative/antimicrobial system. Preferably the additional preservative is added in amounts of at maximum 0.4 wt% and more preferably at or below 0.2 or 0.1 wt%. Most preferably the additional conventional preservative is at max 0.08 wt%, at 0.05 wt% or even below 0.05 wt%, or completely omitted or lowered to such low quantities that it does not need to be registered on the label of the final consumer product. In the cases where additional conventional preservative is still added in above-mentioned quantities, this is mainly because a broader antimicrobial or preservative scope is desired (i.e. becoming effective against more different fungi, yeasts and/or bacteria) or the preservative and/or antimicrobial effect is to be further increased compared to the effect that the originally added amount of additional conventional preservative was showing. In high surfactant systems the amount of additional surfactant may be lowered to between 0.006-0.75 wt%, preferably to 0.4 wt% or below, even more preferably to 0.2 wt% or below.
When the preservative/antimicrobial system is used in addition to other, conventional, preservatives, the lactylate composition was found to have a boosting effect in combination with conventional preservatives. This enables the use of lowered dose- levels of the currently used preservatives such as benzoic acid and salt, sorbic acid and salt, propionic acid and salt, phenoxyethanol, parabens, dehydroactic acid and salt, capryl hydroxamic acid and salt, anisic acid and salt, C6-C14 fatty acids and salts, lactic acid, isothiazolinones, quatermonium compounds. Especially
preservatives chosen from sorbic acid or its salt, benzoic acid or its salt, dehydro acetic acid or its salt, ethyl hexyl glycerin or a combination hereof, most preferably sorbic acid or its salt and dehydro acetic acid were found suitable to be used in combination with the lactylates according to the present description. The fact that the preservative/antimicrobial system enables the use of lowered dose levels is especially an advantage when said conventional preservative is sorbic acid. Sorbic acid is a relatively inexpensive and active preservative, but it is not readily dosed because it is a powder with a relatively low solubility. Sorbic acid powder is difficult to handle and dose and not the safest material to process. If sorbic acid or sorbate is being applied at all, it is added as one of the last ingredients to the final formulation. It is added to for example the final shampoo formulation and not to the surfactant system that is made up for the shampoo formulation. The possibility to use a lower dose and still ensure preservative action by application of the
preservative/antimicrobial system of the present invention, facilitates the use of sorbic acid in liquid compositions. Depending on the usage pH the sorbic is in its
undissociated form or in its dissociated form, for the purpose of this disclosure with sorbic acid, both (undissociated) sorbic acid is meant and (dissociated) sorbate. It was actually found that the problem of using sorbic acid is solved by creating sorbate/lactate solutions or by dissolving sorbic acid and/or sorbate into the lactylate preservative/antimicrobial system according to the present invention. Thus, by using lactate or the lactylate blend of the present invention sorbic acid and/or sorbate may be used as additional preservative in both low surfactant and high surfactant systems as described in the previous paragraphs. The sorbate may be any mineral salt but preferably potassium or sodium sorbate salt or a mixture hereof. The lactate may be any salt but preferably potassium or sodium lactate is applied or a mixture hereof. A new invention thus is directed to a formulation comprising lactate and sorbate, and most preferably the sodium or potassium salts of lactate and sorbate and/or mixtures hereof. The final concentration of sorbic acid and/or sorbate in a lactate solution may be 20 wt% or higher and preferably 30wt% or higher and most preferably 35 or 40%. When added to a high or low surfactant system, the sorbate is present in
concentrations of 0.01 - 0.2 wt% and more preferably 0.05 - 0.15 wt% or 0.05 - 0.10 wt% when combined with 0.1 wt% - 2 wt% of lactic acid and more preferably 0.2-1 wt% or 0.2 -0.5 wt% lactic acid. The present invention further encompasses a formulation of sorbic acid and/or sorbate and the lactylate compositions as described previously in this application with optionally some further lactic acid present. The final concentration of sorbic acid and/or sorbate in a lactylate preservative/antimicrobial system of the present invention may be 0.01 wt% or higher and preferably 0.025wt% or higher and most preferably between 0.025 and 0.075wt%. When added to a low or high surfactant system, sorbic acid and/or sorbate is present in concentrations of about 0.005 - 0.75 and more preferably in 0.01 - 0.40 wt% when combined with 0.1 - 4 wt% and more preferably 0.25 - 2 wt% of the lactylate blend compositions as mentioned previously. The invention encompasses a method for dosing sorbic acid and/or sorbate into formulations for preservative and/or antimicrobial purposes and into the applications described in this disclosure_by combining the sorbic acid and/or sorbate with one or more lactate salts or with the lactylate preservative/antimicrobial system of the present invention or with a mixture of lactate and
preservative/antimicrobial system wherein further optionally some lactic acid may be present. These formulations containing sorbic acid and/or sorbate were in particular found to be very effective in inhibiting fungal growth in non-sterile situations (like for example open bottles or containers at customers) and in preventing fungal growth in closed bottles with very few specimen present.
Especially a preservative/antimicrobial system that fulfills the preferred ranges of the general formula in combination with sorbic acid was found very suitable. The preservation/antimicrobial system comprising the lactylate blend according to the present invention and sorbic acid was found to be effective on a broad scope of microorganisms including fungi and bacteria while the preservation/antimicrobial systems as known in literature have not been found that effective over such a broad scope of microorganisms and usually target only fungi or only bacteria or may be both but then with a much lower efficacy resulting still in growth of one or the other type of microorganism when used in conventional concentrations. To increase the efficacy such high concentrations need to be used that either the formulation becomes too expensive, or the formulations are not acceptable from a regulatory perspective or the organoleptic characteristics of the final consumer product are affected at an unacceptable degree. The use of the lactylate formulations of the present invention prevents the use of such high concentrations and is still effective against both fungi and bacteria while maintaining an acceptable organoleptic profile of the end consumer product and the combination with sorbic acid even further improves this effect.
The preservative/antimicrobial system according to the present description can be used in cleaning compositions in which they reduce or completely inhibit growth or kill microorganisms present at the surface of the object to be cleaned or treated. Since the lactylates also have surfactant properties it further helps to remove spores, germs and other residual contaminant material from the surface. Said cleaning composition may be added to water or other solvent, directly used on a cloth, or may be provided on ready-to-use wipes. The preservative/antimicrobial system can also be used to prevent deterioration of the compositions in which they are used. Accordingly, the preservation/antimicrobial system can be used in cleaning composition comprising the preservative/antimicrobial system, preferably in an amount of between 0.25- 4 wt%, preferably 0.5-2 wt%, based on the total weight of the cleaning composition. Cleaning compositions usually comprise high surfactant systems such as in manual dish wash compositions, and all-purpose cleaners. These cleaning compositions may be used for cleaning surfaces and cooking utensils in food processing plants and in areas in which food is prepared or served such as hospitals nursing homes, restaurants or at home, such as all-purpose cleaners, manual dish washing compositions, disinfective cleaners and sprays and the like. In addition to the preservation/antimicrobial system, other conventional components for cleaning compositions may be present such as detergent, surfactants, surface active agent.
The present disclosure further pertains to an agrochemical composition comprising the preservative/antimicrobial system, preferably in an amount of between 0.25- 4 wt%, preferably 0.5-2 wt%, based on the total weight of the agrochemical
composition. Also in the agrochemical field there is a demand for so-called green formulations which are more human friendly, environmentally friendly, sustainable and low toxic. The present preservative/antimicrobial system may suitably be used in these green agrochemical formulations since they provide good preservation and also antimicrobial activity. Said agrochemical composition may be in the form of a dilutable concentrate (DC), emulsifiable concentrate (EC), suspension concentrate (SC), capsule suspension (CS), oil in water (EW), oil dispersion (OD). Concentrated agrochemical compositions usually are high surfactant systems, while ready-to-use agrochemical compositions usually are low surfactant systems. Common other components in agrochemical compositions are:
- water
- solvents for the actives, preferably“green” solvents such as natural vegetable oils, long chain aliphatic carboxylic acids, triglyceride esters and methylated vegetable oils,
- wetting/dispersing agents,
- antifreeze such as propylene glycol or glycerine
- surfactants, such as anionic, cationic, nonionic and amphoteric surfactants - freeze/thaw additive
- bactericide. These may be added in addition to the lactylate composition
according to the present disclosure,
- foam control agent, and
- viscosity modifier,
- preservative, when desired in addition to the lactylate composition according to the present disclosure. The preservative/antimicrobial system may also be used in addition to other, conventional, preservatives, since the lactylate composition was found to have a boosting effect in combination with conventional preservatives. This may support the lowered dose-levels of the currently used preservatives such as benzoic acid and salt, sorbic acid and salt, propionic acid and salt, phenoxyethanol, parabens, dehydroacetic acid and salt, capryl hydroxamic acid and salt, anisic acid and salt, C6-C14 fatty acids and salts, lactic acid, isothiazolinones, quatermonium compounds
The preservative/antimicrobial system according to the present description can be used in personal care composition comprising the preservative/antimicrobial system, preferably in an amount of between 0.25- 4 wt%, preferably 0.5-2 wt%, based on the total weight of the personal care composition. Said personal care composition may be a personal care cleaning composition or a personal care treatment composition. These personal care compositions can, for example, include skin creams, lotions, milks and powders, skin cleansing products, hair treatment products, such as shampoos, conditioners, styling aids and dental products, such as toothpastes and mouthwashes.
Personal care cleaning composition can be applied topically in the form of ointments, solutions, gels or any other cosmetically acceptable type of composition. They may be formulated for washing the hair or skin, for example, hair shampoos; rinse-off hair care products; bath or shower gels; and facial washing compositions. Said personal cleaning composition may also may be provided on ready-to-use wipes. In addition to the preservative/antimicrobial composition according to the description, personal care cleaning compositions may comprise surfactants, solvents (usually water), structurants such as swelling clays, fatty acids and polyglycol-ethers, thickeners, opacifiers, plant extracts, colourants, cationic surfactant, and perfumes. In the case of personal care compositions, the acyl lactylates are usually employed in a cosmetically acceptable vehicle. They are usually formulated as leave-on
formulations, but they can also be formulated as rinse-off formulation. Rinse-off formulations usually are high surfactant systems, while leave-on formulations usually are low surfactant compositions.
Vehicles other than water can include liquid or solid emollients, solvents, humectants, thickeners and powders.
Examples of each of these types of vehicle which can be used singularly or as mixtures of one or more vehicles, are as follows:
- Emollients, such as stearyl alcohol, glyceryl monoricinoleate, mink oil, cetyl alcohol, isopropyl isostearate, stearic acid, isobutyl palmitate, isocetyl stearate, oleyl alcohol, isopropyl laurate, hexyl laurate, decyl oleate, octadecan-2-ol, isocetyl alcohol, eicosanyl alcohol, behenyl alcohol, cetyl palmitate, silicone oils such as dimethylpolysiloxane,di-n-butyl sebacate, isoporpyl myristate, isopropyl palmitate, isopropyl stearate, butylstearate, polyethylene glycol, triethylene glycol, lanolin, cocoa butter, corn oil, cotton seed oil, olive oil, palm kernel oil, rapeseed oil, safflower seed oil, evening primrose oil, soybean oil, sunflower seed oil, avocado oil, sesame seed oil, coconut oil, arachis oil, castor oil, acetylated lanolin alcohols, petroleum jelly, mineral oil, butyl myristate, isostearic acid, palmitic acid, isopropyl linoleate, lauryl lactate, myristyl lactate, decyl oleate, myristylmyristate;
- Propellants, such a propane, butane, isobutane, dimethyl ether, carbon
dioxide, nitrous oxide;
- Solvents, such as ethyl alcohol, methylene chloride, isopropanol, acetone, ethylene glycol monoethyl ether, diethylene glucol monobutyl ether, diethylene glycol monoethyl ether, dimethyl sulphoxide, dimethyl formamide,
tetrahydrofuran;
- Powders, such as chalk, talc, fullers earth, kaolin, starch, gums, colloidal silica sodium polyacrylate, tetraalkyl and/or trialkyl aryl ammonium smectites, chemically modified magnesium aluminium silicate, organically modified montmorillonite clay, hydrated aluminium silicate, fumed silica, carboxyvinyl polymer, sodium carboxymethylcellulose, ethylene glycol monostearate. - Emulsion ingredients are present if the composition for the use according to the invention is in the form of an emulsion in which case an oil or oily material will normally be present, together with an emulsifier to provide either a water- in-oil emulsion or an oil-in-water emulsion. Examples of suitable oils and oily materials include mineral oil, vegetable oils, silicone oils, both volatile and non volatile, such as polydimethyl siloxanes. The oil or oily material when present for the purposes for forming an emulsion, will normally form up to 90%, preferably from 10 to 80% by volume of the composition. The amount of the emulsifier or mixtures thereof will normally be from 1 to 50%, preferably from 2 to 20% and most preferably from 2 to 10% by weight of the composition. The composition can also comprise of water, usually up to 80%, preferably from 5 to 80% by volume.
- Surfactants, such as anionic, non-anionic, cationic or amphoteric surfactants or mixtures thereof may be present, particularly when the composition is intended for shampooing the hair or for use when bathing or in the shower. When present, the surfactants form from 2 to 40 % by weight and preferably from 5 to 30 % by weight. When the composition is intended as leave-on- product, the presence of surfactants is usually kept low, generally lower than 4 wt%, to avoid the risk of irritation of the skin. Suitable surfactants are sodium lauryl sulfate, sodium laureth sulfate, APG, quats, CAP B, etcetera. As described above, in low surfactant systems the use of additional preservatives could be lowered or omitted altogether. Examples of quats that have shown to work well in combination with the present invention may be ADEBAC (C12-14- alkyl [(ethylphenyl) methyl] dimethyl chlorides), ADBAC (Benzyl C12-16 alkyl dimethyl chlorides), DDAC (Didecyldimethylammonium chloride) and/or combinations hereof. Hydrophylic components may be present to help solubilize and/or physically stabilize the lactylates in the composition and/or to enhance the antimicrobial efficacy and/or the speed of antimicrobial efficacy. Incorporation of a sufficient amount of hydrophilic component in hydrophobic ointments can increase the antimicrobial activity both in terms of speed and extent of kill. Exemplary hydrophilic components include, but are not limited to, water, polyhydric alcohols, lower alkyl ethers (i.e., having a sufficiently small number of carbon atoms to meet the solubility limit above), N- methylpyrrolidone, alkyl esters (i.e., having a sufficiently small number of carbon atoms to meet the solubility limit above), and the lower monohydroxy alcohols. Preferably, the hydrophilic components include polyhydric alcohols, lower alkyl ethers, and short chain esters. More preferably, the hydrophilic components include polyhydric alcohols.
- Other Cosmetic Adjuncts, which include for instance antioxidants, such as butyl hydroxy toluene; humectants such as glycerol, sorbitol; buffers such as lactic acid or sodium hydroxide; waxes such as beeswax, paraffinwax;
moisturizers, plant extracts, such as aloa vera; UV- absorbers, vitamins, anti oxidants, thickeners; colourants; and perfumes,
- Other preservatives. The preservative/antimicrobial system may also be used in addition to other, conventional, preservatives, since the lactylate composition was found to have a boosting effect in combination with conventional preservatives. This may support the lowering of dose-levels or even complete avoidance of use of the currently used preservatives such as benzoic acid and salt, sorbic acid and salt, propionic acid and salt, phenoxyethanol, parabens, dehydroacetic acid and salt, capryl hydroxamic acid and salt, anisic acid and salt, C6-C14 fatty acids and salts, lactic acid, isothiazolinones, quatermonium compounds.
The cosmetically acceptable vehicle will usually form from 10 to 99.9%, preferably from 50 to 99% by weight of the composition, and can, in the absence of other cosmetic adjuncts, form the balance of the composition.
In the case of personal care treatment compositions, the acyl lactylates are also usually employed in cosmetically acceptable vehicle as described above for personal care cleaning compositions. They usually are formulated as leave-on formulation, i.e. as low surfactant system, but rinse-off formulations are also possible. In addition to that, the personal care treatment composition can comprise specific cosmetic adjuncts such as organic sunscreen materials in an amount of from 0.1 to 20%, preferably from 1 to 10% by weight and/or Inorganic sunscreens, such as ultra fine titanium dioxide, dandruff treatment components, anti-acne agents, tanning agent, anti-wrinkle, anti-ageing agents and tooth paste components. The personal care treatment compositions as defined above can also serve as a vehicle to distribute the acyl lactylates to areas such as the human skin, nails, hair or tooth which are affected by undesired microorganisms, in particular fungi.
The present description is also directed to a method for prolonging shelf-life of a composition wherein between 0.25-4 wt%, preferably 0.5-2 wt%, of a
preservative/antimicrobial composition according to claim 1 is added to the
composition, based on the total weight of the composition. Said composition may be a cleaning composition, an agrochemical composition, ink, a coating composition, personal care composition or a personal care cleaning composition. Compositions that can suitably be preserved are for instance cosmetics, deodorants, contact lens products.
The present disclosure is also directed to a method for reducing microbial growth and a method preventing germination or inhibition of spore-forming, comprising treating the microbial cells with a composition comprising the preservative/antimicrobial system according to the disclosure. Said microbial cells may be present in any composition that is susceptible to microbial contamination by bacteria, fungi, yeast or algae.
The present disclosure is also directed to a method for cleaning, disinfecting or inhibiting microbial growth on a locus comprising contacting the locus with a composition comprising the preservative/antimicrobial system according to the present disclosure. With cleaning is also meant: removal of contaminants such as germs and spores. Said locus may be any hard surface, but also human or animal skin, hair, oral cavity, mucous membranes, wounds, bruises or in the eye may be disinfected with the preservative/antimicrobial system according to the present disclosure.
The present disclosure further pertains to the use of the preservative/antimicrobial system according to the disclosure in a cleaning composition or a personal care composition, preferably a body cleaning composition, more preferably a skin cleaning composition or a hair cleaning composition, a body treatment composition, preferably a skin treatment composition and/or a hair treatment composition. The present disclosure is illustrated by means of the following examples. These examples are for illustrative purposes only.
EXAMPLES
Example 1 Anti-microbial activity of lactylate compositions
The antimicrobial effect of various lactylate compositions were tested using the EN1276 and EN1650 test method under dirty conditions (as described in the
EN1650:2008+A1 : 2013 publication and the FprENI 276:2009 and August 2010 NEN-EN 1276AC1 publication), wherein an all-purpose cleaning composition comprising the components as indicated in TABLE I, was contacted for 5 minutes with a specific bacterium or 15 minutes with a specific fungus.
Reaction mixture
To this end 1 ml of Bovine Albumin Serum (BSA) and 1 microliter of the micro organism were combined and mixed for 2 minutes (test suspension 108 CFU/ml). 8 ml of test solution (lactylate + surfactant was added and contacted for 5 minutes (in the case of bacteria) or 15 minutes (in the case of fungi), while mixing.
Neutralizer mixture
Subsequently 1 ml of the resulting reaction mixture was poured in a tube together with 8 ml neutralizer, 1 ml water and contacted while mixing for 5 minutes at a temperature of 20 °C. Samples were taken in duplicate and plated on tryptone soya agar (TSA, in the case of bacteria) or malt extract agar (MEA, in the case of fungi) and incubated 2 times 24 hours at 37 °C ( in the case of bacteria) or 48 +72 hours at 30 °C (in the case of fungi). Finally, the surviving microorganisms were counted.
The results are given in TABLE I wherein the percentages are weight percentages and SLS stands for sodium lauryl sulphate, APG stands for alkyl polyglycoside. EH stands for enterococcus hirae, SA stands for staphylococcus aureus, EC stands for Escherichia coli, PA stands for pseudomonas. aeruginosa, and CA stands for
Candida Albicans, AB stands for Aspargillus Brasilliensis ; a minus (-) indicates that no significant reduction of the microorganisms took place, a plus (+) indicated that for bacteria more than log 5 reduction took place and for fungi that more than log 4 reduction took place, and a plus-minus (+/-) indicates that for bacteria a reduction of between log 3 to log 5 took place and for fungi that a reduction of between log 2.5 and log 4 took place.
TABLE I: Anti-microbial activity of various lactylates on various fungi and bacteria at pH 4.5 or 5.5
Figure imgf000023_0001
The ratios in between brackets as mentioned in the above table are on weight basis. These results show that single lactylates do provide satisfactory activity towards fungal and bacterial growth but only when applied in high dosages that are unacceptable in view of either costs and/or bad effects on organoleptic
characteristics of the final consumer product. When combining three lactylates the synergistic effect of that combination makes it possible to lower the individual dose level of each lactylate and/or they become effective against a broader scope of microorganisms. Example 2 Preservation/antimicrobial activity lactylate compositions
In order to test the activity, various lactylate compositions were bioscreened. All samples contained: 0.25 wt% APG (Alkyl polyglycoside) and 0.01 wt % yeast extract. The pH was set to 5.5 and 6.5 with NaOH or HCI.
The samples further contained C6 or C8 or C10 or C12 lactylate or mixtures hereof in concentrations that were varied between 0 (bianco) and about 1.2 wt% at pH 5.5 and 6.5 as indicated in Table II.
In a 2x 96 wells plate (Bioscreen honeycomb plates) the wells were filled with 200 microliter sample (each sample its own well). To each well of one plate 2microliter bacteria (10L6 cfu/ml mix of e. coli / p. aeruginosa / e.hirae / s. aureus in a volume ratio of 1 : 1 : 1 : 1 ) were added. To the second plate 2 microliter fungal suspension (1 :1 107 cfu/ml mix of c. albicans / a. brasiliensis in a 1 :1 volume ratio) was added.
The plates were placed in a bioscreen machine 30 °C, filter 420-580 nm, and followed for 21 days with every 6 hrs being measured for optical density (OD) using a filter of 420-580 nm. Increase of OD in time meant growth of cells.
The results are given in TABLE II wherein a minus (-) indicates that no significant reduction of the microorganisms took place. In the other situations, the lactylates were present in the compositions in wt% as indicated in the TABLE and in those situations no OD increase was measured during these 21 days, meaning that growth was inhibited for 21 days with the lactylates present in the compositions as indicated. A growth below 0.1 was defined as no growth.
TABLE II: Preserving action of blends of lactylates on fungi and bacteria
Figure imgf000024_0001
Figure imgf000025_0001
These results show that with blends according to the invention microbial growth could be prevented at various pH both for fungi and bacteria at relatively low doses.
Example 3 testing of various lactylate formulations
In the following experiments two lactylate formulations according to the invention were tested at various pH for both fungi and bacteria using the same test conditions as used in example 1 with the exception that microbial growth of a consortium of bacteria and a consortium of fungi was measured after various treatment times up and to 28 days ( if no further change took place over time ( e.g. from 48 hours to 28 days), the data are only given for the period wherein a change in activity was observed). All formulations also comprised 4 wt% sodium laureth sulphate, and 2 wt% alkyl polyglycoside. Further, compositions were tested that comprised
conventional preservative in addition to the preservation/antimicrobial system according to the invention. The results are given below in TABLE III and TABLE IV wherein a minus (-) indicates that no significant reduction took place; A plus (+) indicates that for bacteria more than log 5 reduction took place and for fungi that more than log 4 reduction took place, and a plus-minus (+/-) indicates that for bacteria a reduction of between log 3 to log 5 took place and for fungi that a reduction of between log 2,5 and log 4 took place. Percentages are weight based.
The composition of the lactylate formulation:
Lactylate 1 :
45 wt% C8 lactylate + 45 wt% C10 lactylate + 10 wt% C12 lactylate
Lactylate 2:
65wt% C8 lactylate + 25 wt% C10 lactylate + 10 wt% C12 lactylate TABLE III Activity lactylate 1 formulation
Figure imgf000026_0001
*) experiments not according to the invention TABLE IV Activity lactylate 2 formulation
Figure imgf000027_0001
*) experiments not according to the invention
These experiments show that the preservative/antimicrobial system according to the invention provides adequate protection against both bacteria and fungi while using a concentration of at or below 1 wt%. The experiments further show that the combined use of the preservative/antimicrobial system according to the invention and conventional preservatives improves the protection so that lower concentrations of both can be used. When comparing the effectiveness of lactylate blend according to the invention with the effectiveness of conventional preservatives, the lactylate blend according to the invention provides equal or better protection. Further, lactylate 2 blend proved to give excellent protection in combination with sorbic acid. This shows that a preservative/ antimicrobial system comprising 40-70 wt% of C8 lactylate, 25-50 wt% C10 lactylate and 2-15 wt% C12 lactylate and sorbic acid gives optimal protection.
The faster a reduction in growth is observed, the better this is for the logistics in the manufacturing process as a production batch may be released sooner and thus production time may be reduced.
Furthermore, the longer it takes to reduce growth, the faster the still alive or present microorganisms will duplicate and the faster a concentration of microbial cells is reached at which the added dose of preservatives is no longer sufficient. It is observed from the Tables above that the preservative/antimicrobial system of the present invention is able to reduce growth faster than the conventional preservatives and thereby prevent the concentration of cells to become that high that the added dose of preservative/antimicrobial system is too low to have sufficient effect. This further prevents (re)contamination due to the customer (re-) opening the package.

Claims

CLAIMS:
1. Preservative/antimicrobial system having an effective pH range of 4.5-7
comprising a blend of lactylates of the general formula:
R1 -COO[-CH(CH3)-COO]n- H, wherein: n= between 1 and 6,
or a salt of the compound according to the general formula and wherein:
a) 20-80 wt.%, preferably 60-70 wt% of the blend comprises a lactylate wherein R1 represents an C7 alkyl or alkenyl chain which may be branched or unbranched,
b) 20-80 wt.%, preferably 25-50 wt%, most preferably 27-45 wt% of the blend comprises a lactylate wherein R1 represents an C9 alkyl or alkenyl chain which may be branched or unbranched, and
c) 1 -30 wt. %, preferably 2-15 wt%, more preferably 9-12 wt%, of the blend
comprises a lactylate wherein R1 represents an C1 1 alkyl or alkenyl chain which may be branched or unbranched.
2. Preservative/antimicrobial system according to claim 1 , wherein n is 1 and/or 2 in either one of the groups of lactylates falling within the definition of a., b., and c.
3. Preservative/antimicrobial system according to claim 1 , wherein the ratio a/b/c between the amounts in weight of lactylates falling within the definition of a., b., and c., respectively, is in the range of 0.9-1.1 1 0.9-1.1 / 0.15-0.25.
4. Preservative/antimicrobial system according to claim 1 , wherein additional
conventional preservative is present, said preservative preferably chosen from sorbic acid or its salt, benzoic acid or its salt, dehydro acetic acid or its salt, ethyl hexyl glycerin, isothiazolinone or a combination hereof, most preferably sorbic acid or its salt or dehydro acetic acid is present.
5. High surfactant system comprising preservative/antimicrobial system according to any one of the preceding claims and surfactant, wherein at least 4 wt% of the high surfactant system consists of preservative/antimicrobial system and surfactant.
6. High surfactant system according to claim 5 wherein the reservative/antimicrobial system comprises between 0.006- 0.75 wt% of sorbic acid, preferably 0.4 wt% or below, more preferably 0.2 or below, most preferably between 0.2-0.1 wt% based on the total weight of the preservative/antimicrobial system.
7. High surfactant system according to claim 6, wherein the amount of surfactant os 3.5 wt% or below, preferably 3 wt% or below, more preferably 2 wt % or below, based on the total weight of the preservative/antimicrobial system.
8. Low surfactant system comprising preservative/antimicrobial system according to any one of the preceding claims'! -4 and surfactant, wherein less than 4 wt% of the high surfactant system consists of preservative/antimicrobial system and surfactant.
9. Low surfactant system according to claim 8 wherein the preservative/antimicrobial system comprises between 0.0 - 0.75 wt% of sorbic acid, preferably 0.4 wt% or below, more preferably 0.02wt% or most preferably 0.1 wt% or below, based on the total weight of the preservative/antimicrobial system.
10. Cleaning composition comprising the preservative/antimicrobial system according to any one of preceding claims 1 -9, preferably in an amount of between 0.25- 4 wt%, more preferably between 0.5-2 wt%, based on the total weight of the composition.
1 1. Cleaning composition according to claim 10 wherein the cleaning composition is a high surfactant system.
12. Cleaning composition according to claim 1 1 wherein the composition is an all purpose cleaning composition or a dish washing composition.
13. Cleaning composition according to claim 10, wherein the composition comprises further additives such as detergent, surfactant, surface active agent, colorant, perfume.
14. Agrochemical composition comprising the preservative/antimicrobial system
according to any one of claims 1 -9, preferably in an amount of between 0.25- 4 wt%, based on the total weight of the agrochemical composition
15. Personal care composition comprising the preservative/antimicrobial system
according to any one of claim 1 -9, preferably in an amount of between 0.25- 4 wt%, preferably 0.5-2 wt% based on the total weight of the composition.
16. Personal care composition according to claim 15, wherein the composition is a personal care cleaning composition or a personal care treatment composition.
17. Personal care composition according to claim 15 or 16, wherein the composition comprises further additives such as surfactants, detergent, colorant, and perfume.
18. Method for prolonging shelf-life of a composition wherein between 0.25-4,
preferably 0.5-2 wt% of the preservative/antimicrobial system according to the disclosure is added to the cleaning composition, based on the total weight of the cleaning composition.
19. Method according to claim 18, wherein said composition is a cleaning
composition, an agrochemical composition, a personal care composition, a personal care treatment composition, a personal care cleaning composition, an ink or a coating.
20. Method for reducing microbial growth comprising treating the microbial cells with a composition comprising the preservative/antimicrobial system according to any one of claims 1 -9.
21. Method for a method preventing germination or inhibition of spore-forming comprising treating the microbial cells with a composition comprising the preservative/antimicrobial system according to any one of claims 1 -9.
22. Method for cleaning, disinfecting or inhibiting microbial growth on a locus
comprising contacting the locus with a composition comprising the
preservative/antimicrobial system according to any one of claims 1 -9.
23. Use of the preservative/antimicrobial system according to any one of preceding claims 1 -9 in a cleaning composition and agrochemical composition or a personal care composition, preferably a body cleaning composition, more preferably a skin cleaning composition or a hair cleaning composition, a body treatment
composition, preferably a skin treatment composition and/or a hair treatment composition.
PCT/EP2020/062194 2019-05-15 2020-05-01 Lactylate blend for preservative/antimicrobial system WO2020229202A1 (en)

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Citations (16)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4198311A (en) * 1978-07-03 1980-04-15 C. J. Patterson Company Skin conditioning toilet bar
EP0572271A2 (en) 1992-05-29 1993-12-01 Unilever Plc Acyl lactylates as antimicrobial actives
EP0595528A2 (en) * 1992-10-23 1994-05-04 Unilever Plc Skin cosmetic composition containing lactylates
US5490955A (en) * 1992-02-27 1996-02-13 Elizabeth Arden Company, Division Of Conopco, Inc. Cleansing compositions based on C10 -C16 acyl lactylate
WO1998022086A1 (en) 1996-11-18 1998-05-28 Unilever Plc Aqueous cleansing composition
WO2002008377A1 (en) 2000-07-21 2002-01-31 Novozymes A/S Antimicrobial compositions
US20050053593A1 (en) 2003-09-09 2005-03-10 3M Innovative Properties Company Antimicrobial compositions and methods
US20060051384A1 (en) 2004-09-07 2006-03-09 3M Innovative Properties Company Antiseptic compositions and methods of use
US20090082253A1 (en) * 2007-09-17 2009-03-26 Purac Biochem B.V. Antibacterial agent based on fatty acid esters of hydroxy carboxylic acid acids
WO2009037274A1 (en) 2007-09-17 2009-03-26 Purac Biochem Bv Preservation of acidic beverages
WO2009037269A1 (en) 2007-09-17 2009-03-26 Purac Biochem Bv New antibacterial agent based on fatty acid esters of hydroxy carboxylic acids
US20090169655A1 (en) * 2007-08-10 2009-07-02 Lori Ann Porter Insect repellent formulation
WO2009092787A1 (en) 2008-01-25 2009-07-30 Purac Biochem Bv Lactylates for the prevention and treatment of infections caused by gram-positive bacteria in animals
EP2745877A1 (en) * 2012-12-20 2014-06-25 PURAC Biochem BV Oral care product comprising lactylate
CN107602248A (en) * 2017-10-20 2018-01-19 刘青亚 A kind of nutrition is comprehensive, the production method of green foliar fertilizer
WO2018222184A1 (en) * 2017-05-31 2018-12-06 Kimberly-Clark Worldwide, Inc. Antimicrobial composition including an acyl lactylate and a glycol and methods of inhibiting microbial growth utilizing the same

Patent Citations (19)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4198311A (en) * 1978-07-03 1980-04-15 C. J. Patterson Company Skin conditioning toilet bar
US5490955A (en) * 1992-02-27 1996-02-13 Elizabeth Arden Company, Division Of Conopco, Inc. Cleansing compositions based on C10 -C16 acyl lactylate
EP0572271A2 (en) 1992-05-29 1993-12-01 Unilever Plc Acyl lactylates as antimicrobial actives
AU665081B2 (en) * 1992-05-29 1995-12-14 Unilever Plc Acyl lactylates as antimicrobial actives
EP0595528A2 (en) * 1992-10-23 1994-05-04 Unilever Plc Skin cosmetic composition containing lactylates
WO1998022086A1 (en) 1996-11-18 1998-05-28 Unilever Plc Aqueous cleansing composition
US6001787A (en) 1996-11-18 1999-12-14 Helene Curtis, Inc. Aqueous cleansing composition
WO2002008377A1 (en) 2000-07-21 2002-01-31 Novozymes A/S Antimicrobial compositions
US20050053593A1 (en) 2003-09-09 2005-03-10 3M Innovative Properties Company Antimicrobial compositions and methods
US20060051384A1 (en) 2004-09-07 2006-03-09 3M Innovative Properties Company Antiseptic compositions and methods of use
US20090169655A1 (en) * 2007-08-10 2009-07-02 Lori Ann Porter Insect repellent formulation
US20090082253A1 (en) * 2007-09-17 2009-03-26 Purac Biochem B.V. Antibacterial agent based on fatty acid esters of hydroxy carboxylic acid acids
WO2009037274A1 (en) 2007-09-17 2009-03-26 Purac Biochem Bv Preservation of acidic beverages
WO2009037269A1 (en) 2007-09-17 2009-03-26 Purac Biochem Bv New antibacterial agent based on fatty acid esters of hydroxy carboxylic acids
WO2009092787A1 (en) 2008-01-25 2009-07-30 Purac Biochem Bv Lactylates for the prevention and treatment of infections caused by gram-positive bacteria in animals
US20180193301A1 (en) * 2008-01-25 2018-07-12 Purac Biochem Bv Lactylates for the prevention and treatment of infections caused by gram-positive bacteria in animals
EP2745877A1 (en) * 2012-12-20 2014-06-25 PURAC Biochem BV Oral care product comprising lactylate
WO2018222184A1 (en) * 2017-05-31 2018-12-06 Kimberly-Clark Worldwide, Inc. Antimicrobial composition including an acyl lactylate and a glycol and methods of inhibiting microbial growth utilizing the same
CN107602248A (en) * 2017-10-20 2018-01-19 刘青亚 A kind of nutrition is comprehensive, the production method of green foliar fertilizer

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
"Personal care. A modern, multifunctional anti-drandruff agent", 1 January 2012, article DR. STRAETMANS ET AL: "Personal care. A modern, multifunctional anti-drandruff agent", XP055673671 *
WILMA F BERGFELD ET AL: "Safety Assessment of Alkyl Lactyl Lactate Salts as Used in Cosmetics The 2018 Cosmetic Ingredient Review Expert Panel members are: Chair", 1 January 2018 (2018-01-01), XP055673720, Retrieved from the Internet <URL:https://cir-safety.org/sites/default/files/alkylL122018rep.pdf> [retrieved on 20200304] *

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