Antimicrobial composition

Abstract

Provided herein are antimicrobial compositions comprising an alkylene glycol ester and at least one antimicrobial compound, wherein suitably the alkylene glycol ester and the antimicrobial compound are present in the antimicrobial composition in a beneficial weight ratio. Also provided are methods for increasing the efficacy of an antimicrobial compound and methods for reducing the minimum amount of an antimicrobial compound required to remain active in an end use formulation.

Description

Technical Field

[0001] This invention relates to antimicrobial compositions comprising an alkylene glycol ester and at least one antimicrobial compound, wherein suitably, the alkylene glycol ester and the antimicrobial compound are present in the antimicrobial composition in a weight ratio for providing a synergistic effect. Furthermore, this invention relates to a method for inhibiting microbial growth in an end-user formulation (e.g., a personal care or home care product) comprising the antimicrobial composition, and to an end-user formulation comprising the antimicrobial composition. Technical Background

[0003] Microbial contamination of personal care products (such as cosmetics, home care products, and other similar products) is a significant problem for industries such as the personal care industry. Microbial contamination can be a major cause of product loss in end-use formulations and can lead to significant economic losses. Furthermore, contamination of cosmetics and home care products can transform them into products harmful to users. Certain antimicrobial compounds and compositions for protection against microbial attacks from bacterial or fungal sources are known in the art. These antimicrobial compounds have wide applications in fields such as personal care products, home care products, and health and hygiene products.

[0004] In end-use formulations, there is ongoing regulatory pressure to reduce the amount of antimicrobial compounds. Similarly, in the field of formulations such as personal care preparations, there is ongoing regulatory pressure to reduce the amount of active ingredients in said formulations. Additionally, there is ongoing regulatory pressure to discontinue the use of certain conventional antimicrobial compounds or to reduce the amount of certain conventional antimicrobial compounds in end-use formulations.

[0005] Therefore, there is a need for antimicrobial compositions that contain fewer active ingredients or antimicrobial compounds while maintaining an acceptable level of overall antimicrobial efficacy.

[0006] Invention Summary

[0007] The compositions and methods of the present invention satisfy the above-mentioned needs. Therefore, the present invention provides a mixture of at least one antimicrobial compound with an alkylene glycol ester (appropriately synergistically), which can be used in various formulations, including personal care and home care formulations. The inventors have surprisingly discovered that, when both the alkylene glycol ester and at least one antimicrobial compound are present, the antimicrobial composition allows for the application of small amounts of the active ingredient while still producing the desired antimicrobial efficacy.

[0008] In a first aspect, the present invention relates to an antimicrobial composition comprising an alkylene glycol ester and at least one antimicrobial compound selected from citric acid and its salts, salicylic acid and its salts, gluconolactone, levulinic acid and its salts, ethyl levulinate, butyl levulinate, ethylhexylglycerol, ethylene glycol, 1,3-propanediol, 1,3-butanediol, 2,3-butanediol, 1,2-pentanediol, 1,2-hexanediol, caprylyl glycol, ethyl lactate, butyl lactate, clomiphene citrate, 1,2-decanediol, 4-hydroxyacetophenone, and caprylhydroxamic acid. 5-chloro-2-(2,4-dichlorophenoxy)phenol (also known as triclosan), methyl heptaglycerol, polyglycerol-2, 3, 4, 6, or 10-caprylate, polyglycerol-2, 3, 4, 6, or 10-decanoate / caprylate, azelaic acid, vitamin C, zinc oxide, zinc citrate, zinc pyrrolidone carboxylate (PCA zinc), zinc glycinate, zinc oxide, nicotinamide, hyaluronic acid, 2-methyl-5-cyclohexylpentanol, aluminum sulfate, aluminum zirconium, aluminum chloride, aluminum chloride hydrate, other aluminum salts, benzoyl peroxide, glycolic acid, phenylethanol, 3-phenylprop-1-ol, anisic acid and its salts, 1,2-heptanediol, caprylyl glyceryl ether, caprylyl glycine, tetrasodium glutamate. diacetate), trisodium dicarboxymethylalanine, and phytic acid and its salts, wherein the alkylene glycol ester and the antimicrobial compound are present in a weight ratio of about 1:1000 to about 2500:1.

[0009] In a second aspect, the present invention relates to an antimicrobial composition comprising an alkylene glycol ester and at least one antimicrobial compound selected from citric acid and its salts, salicylic acid and its salts, gluconolactone, levulinic acid and its salts, ethyl levulinate, butyl levulinate, ethylhexylglycerin, ethylene glycol, 1,3-propanediol, 1,3-butanediol, 2,3-butanediol, 1,2-pentanediol, 1,2-hexanediol, octyl glycol, ethyl lactate, butyl lactate, clomiphene, 1,2-decanediol, 4-hydroxyacetophenone, octyl isohydroxamic acid and its salts, octyl glycerol, chlorphenesin, triclosan, methylheptylglycerin, polyglycerol-2, 3, 4, or 6. Or 10-octanoate, polyglycerol-2, 3, 4, 6 or 10-decanoate / octanoate, azelaic acid, nonanoic acid, vitamin C, zinc oxide, zinc citrate, zinc pyrrolidone carboxylate (PCA zinc), zinc glycinate, zinc oxide, nicotinamide, hyaluronic acid, 2-methyl-5-cyclohexylpentanol, aluminum sulfate, aluminum zirconium, aluminum chloride, hydrated aluminum chloride, other aluminum salts, benzoyl peroxide, glycolic acid, phenethyl alcohol, 3-phenylprop-1-ol, anisic acid and its salts, 1,2-heptanediol, octylglycerol ether, octyl glycine, tetrasodium diacetate of glutamate, trisodium dicarboxymethylalanine, and phytic acid and its salts, wherein the alkylene glycol esters and the antimicrobial compounds are present in synergistically effective amounts.

[0010] In a third aspect, the present invention relates to end-use formulations comprising the antimicrobial composition according to the invention, preferably home care or personal care products.

[0011] In a fourth aspect, the present invention relates to a method for inhibiting the growth of microorganisms in a home care product, a personal care product, or an aqueous ingredient to be added to a home care product or a personal care product, comprising the step of adding an antimicrobial composition according to the invention to said home care product, personal care product, or aqueous ingredient.

[0012] In a fifth aspect, the present invention relates to a method for preventing end-use formulations (preferably home care or personal care products) from microbial spoilage, comprising incorporating an antimicrobial composition according to the invention into the end-use formulation (preferably home care or personal care product).

[0013] In a sixth aspect, the present invention relates to the use of the antimicrobial composition according to the invention for improving efficacy against microorganisms compared with an equal amount of at least one antimicrobial compound excluding the alkylene glycol ester, preferably wherein the increased efficacy is determined by a synergistic index value of less than 1.

[0014] In a seventh aspect, the present invention relates to a method for enhancing the efficacy of an antimicrobial compound against microorganisms in an end-use formulation, the method comprising providing an end-use formulation and at least one antimicrobial compound, adding an effective amount of an alkylene glycol ester to the at least one antimicrobial compound and the end-use formulation, thereby increasing the efficacy of the at least one antimicrobial compound in the end-use formulation compared to an equivalent amount of the antimicrobial compound in which the alkylene glycol ester is not present, wherein the at least one antimicrobial agent is selected from citric acid and its salts, salicylic acid and its salts, gluconolactone, levulinic acid and its salts, ethyl levulinate, butyl levulinate, ethylhexylglycerin, ethylene glycol, 1,3-propanediol, 1,3-butanediol, 2,3-butanediol, 1,2-pentanediol, 1,2-hexanediol, octanediol, ethyl lactate, butyl lactate, clomiphene, 1 2-Decanediol, 4-Hydroxyacetophenone, Octylisohydroxamic acid and its salts, Caprylic acid glyceride, Chlorphenesin, Triclosan, Methylheptaglycerin, Polyglycerol-2, 3, 4, 6, or 10-caprylate, Polyglycerol-2, 3, 4, 6, or 10-decanoate / caprylate, Azelaic acid, Vitamin C, Zinc oxide, Zinc citrate, Zinc pyrrolidone carboxylate (PCA zinc), Zinc glycine, Zinc oxide, Nicotinamide, Hyaluronic acid, 2-Methyl-5-cyclohexane Amyl alcohol, aluminum sulfate, aluminum zirconium, aluminum chloride, hydrated aluminum chloride, other aluminum salts, benzoyl peroxide, glycolic acid, phenylethanol, 3-phenylprop-1-ol, anisic acid and its salts, 1,2-heptanediol, octylglycerol ether, octyl glycine, tetrasodium diacetate of glutamic acid, trisodium dicarboxymethylalanine, nonanoic acid and phytic acid and their salts; and alkylene glycol esters thereof derived from (a) alkylene glycols and (b) fatty acids having about 6 to 14 carbon atoms. Invention Details

[0016] The invention will be explained in more detail below.

[0017] definition

[0018] To facilitate understanding of this invention, some definitions of terms used in the course of this invention are explained below.

[0019] Generally, the present invention relates to antimicrobial compositions. As used herein, the term "antimicrobial compound" refers to a biocide or biocide composition intended to be incorporated into end-use formulations, such as personal care formulations, home care formulations, and health and hygiene products, to prevent microorganisms from destroying the end-use formulation or rendering the end-use formulation unusable for the specific purpose for which the end-use formulation was developed.

[0020] It has now been surprisingly discovered that incorporating a certain amount of alkylene glycol ester into an antimicrobial compound for use in an end-use formulation can provide an effective antimicrobial end-use formulation, wherein there is a synergistic interaction between the antimicrobial compound and the alkylene glycol ester. As used herein, “synergistic interaction” means that the total antimicrobial / antifungal activity of the antimicrobial compound, when combined with an alkylene glycol ester, is greater than the antimicrobial / antifungal properties of either the antimicrobial compound alone or the alkylene glycol ester alone. In other words, the antimicrobial compound of the present invention synergizes with the alkylene glycol ester, thereby exhibiting greater antimicrobial / antifungal activity against certain microorganisms in their respective presence compared to the antimicrobial activity of the same concentration of either the antimicrobial compound alone or the alkylene glycol ester alone. Due to the synergistic effect, the amount of antimicrobial compound present in the antimicrobial composition can be reduced while still producing the desired efficacy. This effect is also referred to herein as “enhancement” of the antimicrobial compound in the antimicrobial composition. This enhancement of the antimicrobial compound is also referred herein as the “synergistic effect” between the antimicrobial compound and the alkylene glycol ester for enhancing the efficacy of the antimicrobial compound.

[0021] Furthermore, the use of the antimicrobial compositions disclosed herein offers numerous technical advantages and benefits. For example, the antimicrobial compositions disclosed herein can maintain antibacterial and / or antifungal activity at a variety of pH levels. Additionally, the antimicrobial compositions disclosed herein generally remain stable during temperature variations and during changes encountered during the manufacture, packaging, transportation, and storage of the final formulation in which the antimicrobial composition may be included. Furthermore, the antimicrobial compositions disclosed herein are physically and chemically compatible with components present in a variety of end-use formulations. Finally, as further described herein, the antimicrobial compositions of the present invention may contain small amounts of antimicrobial compounds but still provide antimicrobial efficacy that meets industry standards.

[0022] As used herein, the term "alkyl" in each case refers to a straight-chain or branched saturated hydrocarbon group that typically has 1 to 8 carbon atoms, preferably 1 to 6 or 1 to 4 carbon atoms, more preferably 1 to 3 or 1 to 2 or 1 carbon atom. Examples of alkyl groups include methyl, ethyl, n-propyl, isopropyl, n-butyl, 2-butyl, isobutyl, tert-butyl, n-pentyl, 1-methylbutyl, 2-methylbutyl, 3-methyl-butyl, 2,2-dimethylpropyl, 1-ethylpropyl, n-hexyl, 1,1-dimethylpropyl, 1,2-dimethylpropyl, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 1,1-dimethylbutyl, 1,2-dimethyl-butyl, 1,3-dimethylbutyl, 2,2-dimethylbutyl, 2,3-dimethylbutyl, 3,3-dimethylbutyl, 1-ethylbutyl, 2-ethylbutyl, 1,1,2-trimethylpropyl, 1,2,2-trimethylpropyl, 1-ethyl-1-methylpropyl, 1-ethyl-2-methylpropyl, etc.

[0023] As used herein, the term "alkenyl" in each case refers to a straight-chain or branched hydrocarbon group having 2 to 18 carbon atoms, often 2 to 8 or 2 to 6 carbon atoms, typically having one or more C=C double bonds. Where appropriate, the alkenyl moiety may be (E)- or (Z)-configuration.

[0024] As used herein, the term "alkynyl" in each case refers to a straight-chain or branched hydrocarbon group having one or more C=C triple bonds, typically having 2 to 18 carbon atoms, often 2 to 8, 2 to 6, or 2 to 4 carbon atoms.

[0025] As used herein, the term "cycloalkyl" refers to a saturated bicyclic or monocyclic hydrocarbon that typically, and unless otherwise defined in the specification, has a single connection point to the rest of the molecule and has 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, or 18 cyclic carbon atoms. The C3-8-cycloalkyl group may be unsubstituted or substituted with one, two, or three substituents (unless otherwise specified elsewhere in this specification), which may be the same or different, and (unless otherwise specified elsewhere in this specification) selected from C1-6-alkyl, C1-6-alkoxy, halogen, hydroxyl, unsubstituted or mono- or di-substituted amino groups. Exemplary cycloalkyl groups are cyclopentyl, cyclohexyl, and cycloheptyl.

[0026] As used herein, the term "aryl" (alone or as part of a larger group, such as an aryloxy group) refers to an aromatic ring system (i.e., satisfying the Hückel rule – having (4n+π²) electrons, where n is 0 or preferably an integer from 1 to 3), which can be monocyclic, bicyclic, or tricyclic. Examples of such rings include phenyl, naphthyl, or indenyl. Preferred aryl groups are phenyl and naphthyl, with phenyl being the most preferred. Suitable examples of aryloxy rings include phenoxy.

[0027] As used herein, the term "alkoxy" in each case refers to an alkyl substituent as defined above, which is attached to another structural part by an oxygen atom (-O-). Exemplary alkoxy groups are methoxy, trifluoromethoxy, ethoxy, 2,2,2-trifluoroethoxy, n-propoxy, isopropoxy, n-butoxy, sec-butoxy, tert-butoxy, and n-pentoxy.

[0028] The organic part mentioned in the definitions of the variables above—such as the term halogen—is a collective term that is a separate enumeration of the individual group members. The prefixes Cn-Cm (and Cn to Cm or Cn-m) in each case indicate the possible number of carbon atoms in the group.

[0029] As used in this article, the term "carbonyl" refers to the carbonyl moiety, also known as "C(O)" or "C=O".

[0030] The term "halogen" in each case refers to fluorine, bromine, chlorine, or iodine.

[0031] As used herein, the term "comprising" should be interpreted to encompass both "including" and "consisting of," both meanings specific to the invention and the embodiments disclosed therein. A composition of the invention may include, comprise, or consist substantially of, the components of the invention as well as other ingredients described herein. As used herein, "consistently consisting of" means that a composition or component may include additional ingredients, but only if such additional ingredients do not substantially alter the essential and novel characteristics of the claimed composition or method.

[0032] The articles “a” and “an” preceding an element or component as used herein imply that the number of instances (i.e., existence) of an element or component is non-restrictive. Therefore, “a” or “an” should be understood to include one (type) or at least one (type), and the singular form of an element or component also includes the plural, unless the number clearly indicates the singular.

[0033] As used herein, the term "about" to modify the amount of a substance, ingredient, component, or parameter refers to a numerical quantity that may vary, for example, through typical measurement and processing procedures (e.g., liquid processing procedures for preparing concentrates or solutions). Furthermore, variations in the preparation, source, or purity of the ingredients used to implement this invention may occur due to inadvertent errors in the measurement procedures. In one embodiment, the term "about" means within 10% of the reported value. In a more specific embodiment, the term "about" means within 5% of the reported value.

[0034] As described above, the present invention relates, in a first aspect, to an antimicrobial composition comprising an alkylene glycol ester and at least one antimicrobial compound selected from citric acid and its salts, salicylic acid and its salts, gluconolactone, levulinic acid and its salts, ethyl levulinate, butyl levulinate, ethylhexylglycerin, ethylene glycol, 1,3-propanediol, 1,3-butanediol, 2,3-butanediol, 1,2-pentanediol, 1,2-hexanediol, octanediol, ethyl lactate, butyl lactate, clomiphene, 1,2-decanediol, 4-hydroxyacetophenone, octyl isohydroxamic acid and its salts, octyl glycerol, chlorphenesin, triclosan, methylheptylglycerin, polyglycerol-2 or 3 The antimicrobial compound is present in a weight ratio of about 1:1000 to about 2500:1, including 4, 6, or 10-octanoate, polyglycerol-2, 3, 4, 6, or 10-decanoate / octanoate, azelaic acid, vitamin C, zinc oxide, zinc citrate, zinc pyrrolidone carboxylate (PCA zinc), zinc glycinate, zinc oxide, nicotinamide, hyaluronic acid, 2-methyl-5-cyclohexylpentanol, aluminum sulfate, aluminum zirconium, aluminum chloride, hydrated aluminum chloride, other aluminum salts, benzoyl peroxide, glycolic acid, phenethyl alcohol, 3-phenylprop-1-ol, anisic acid and its salts, 1,2-heptanediol, octylglycerol ether, octyl glycine, tetrasodium diacetate of glutamate, trisodium dicarboxymethylalanine, and phytic acid and its salts.

[0035] According to a second aspect, the present invention relates to an antimicrobial composition comprising an alkylene glycol ester and at least one antimicrobial compound selected from citric acid and its salts, salicylic acid and its salts, gluconolactone, levulinic acid and its salts, ethyl levulinate, butyl levulinate, ethylhexylglycerin, ethylene glycol, 1,3-propanediol, 1,3-butanediol, 2,3-butanediol, 1,2-pentanediol, 1,2-hexanediol, octyl glycol, ethyl lactate, butyl lactate, clomiphene, 1,2-decanediol, 4-hydroxyacetophenone, octyl isohydroxamic acid and its salts, octyl glycerol, chlorphenesin, triclosan, methylheptylglycerin, polyglycerol-2, 3, 4, or 6. Or 10-octanoate, polyglycerol-2, 3, 4, 6 or 10-decanoate / octanoate, azelaic acid, nonanoic acid, vitamin C, zinc oxide, zinc citrate, zinc pyrrolidone carboxylate (PCA zinc), zinc glycinate, zinc oxide, nicotinamide, hyaluronic acid, 2-methyl-5-cyclohexylpentanol, aluminum sulfate, aluminum zirconium, aluminum chloride, hydrated aluminum chloride, other aluminum salts, benzoyl peroxide, glycolic acid, phenethyl alcohol, 3-phenylprop-1-ol, anisic acid and its salts, 1,2-heptanediol, octylglycerol ether, octyl glycine, tetrasodium diacetate of glutamate, trisodium dicarboxymethylalanine, and phytic acid and its salts, wherein the alkylene glycol esters and the antimicrobial compounds are present in synergistically effective amounts.

[0036] The following sections provide further detailed description of specific embodiments of the first and second aspects of the invention, such as antimicrobial compounds, proportions, etc. It should be understood that each embodiment, both individually and in combination with other embodiments, is relevant.

[0037] Embodiments of the present invention include one or more alkylene glycol esters. The alkylene glycol esters used in the present invention can be formed from saturated, unsaturated, natural, or synthetic fatty acids, etc. For example, saturated fatty acids include caprylic acid, capric acid, hexanoic acid, dodecanoic acid, lauric acid, myristic acid, palmitic acid, stearic acid, arachidic acid, behenic acid, tetracosanoic acid, ceric acid, nonanoic acid, combinations thereof, and derivatives thereof. Fatty acids having a carbon chain length of about 5 to about 16 carbon atoms are particularly suitable for forming alkylene glycol esters. Alkylene glycol esters can be formed from any suitable alkylene group, such as ethylene, butylene, or propylene. Alkylene glycol esters can comprise monoesters or diesters. In one aspect, mixtures of monoesters, mixtures of diesters, or mixtures of monoesters and diesters can be incorporated into the compositions of the present invention. In one aspect, at least one monoester is used, and it comprises a majority of the alkylene glycol ester present.

[0038] In some embodiments, the alkylene glycol ester is derived from (a) propylene glycol and (b) a fatty acid having about 6 to 12 carbon atoms, such as hexanoic acid, octanoic acid, capric acid, lauric acid, and mixtures thereof. For example, propylene glycol C6-C12 fatty acid monoesters or diesters can be used. Propylene glycol C6-C14 fatty acid monoesters or diesters can also be used.

[0039] Suitable examples of alkylene glycol esters include, but are not limited to, propylene glycol isostearate, propylene glycol laurate, propylene glycol myristate, propylene glycol oleate, propylene glycol monolaurate, propylene glycol monodecanoate, propylene glycol monooctanoate, propylene glycol monohexanoate, propylene glycol diperlargonate, propylene glycol diisostearate, propylene glycol dilaurate, propylene glycol monopalmitate, propylene glycol monostearate, or mixtures thereof, other complexes or derivatives thereof.

[0040] A suitable example of an alkylene glycol diester is propylene glycol dioctanoate.

[0041] In one embodiment, the alkylene glycol ester is primarily propylene glycol monooctanoate. Propylene glycol monooctanoate may comprise a mixture of propylene glycol monoester and diester. For example, propylene glycol monooctanoate may contain 2-hydroxypropyl octanoate (e.g., 40 wt.-% to 70 wt.-%), 2-hydroxy-1-methylethyl octanoate (e.g., 23 wt.-% to 33 wt.-%), and 1,2-propanediol dioctanoate (e.g., 5 wt.-% to 28 wt.-%).

[0042] In one embodiment, the alkylene glycol ester comprises propylene glycol octanoate (PGC). In one embodiment, the alkylene glycol ester comprises a mixture of at least one mono- and di-propylene glycol octanoate. In one embodiment, the alkylene glycol ester is a mixture of at least one mono- and di-propylene glycol octanoate. In one embodiment, the at least one mono-propylene glycol octanoate is selected from 2-hydroxy-1-methylethyl octanoate, 2-hydroxypropyl octanoate, and combinations thereof. In one embodiment, the at least one mono-propylene glycol octanoate is a mixture of 2-hydroxy-1-methylethyl octanoate and 2-hydroxypropyl octanoate. In one embodiment, the di-propylene glycol octanoate is 1,2-propanediol dioctanoate. In one embodiment, based on the total weight of the alkylene glycol ester, the alkylene glycol ester comprises at least 50 wt.% of at least one mono-propylene glycol octanoate, preferably at least 60 wt.% of at least one mono-propylene glycol octanoate, more preferably at least 70 wt.% of at least one mono-propylene glycol octanoate. In one embodiment, the at least one monooctanoic acid propylene glycol ester and dioctanoic acid propylene glycol ester are contained in the mixture in a weight ratio of 15:1 to 1:1, preferably 10:1 to 1:1, and more preferably 5:1 to 2:1.

[0043] In one embodiment, the alkylene glycol ester comprises a mixture of 2-hydroxy-1-methylethyl octanoate, 2-hydroxypropyl octanoate, and 1,2-propanediol dioctanoate. In one embodiment, based on the total weight of the alkylene glycol ester, the alkylene glycol ester comprises 20 wt.-% to 35 wt.-% of 2-hydroxy-1-methylethyl octanoate, 40 wt.-% to 70 wt.-% of 2-hydroxypropyl octanoate, and 5 wt.-% to 30 wt.-% of 1,2-propanediol dioctanoate.

[0044] In one embodiment, based on the total weight of the alkylene glycol ester, the alkylene glycol ester comprises 20 wt.-% to 30 wt.-% of 2-hydroxy-1-methylethyl octanoate, 40 wt.-% to 60 wt.-% of 2-hydroxypropyl octanoate, and 20 wt.-% to 30 wt.-% of 1,2-propanediol dioctanoate.

[0045] In one embodiment, based on the total weight of the alkylene glycol ester, the alkylene glycol ester comprises 20 wt.-% to 40 wt.-% of 2-hydroxy-1-methylethyl octanoate, 50 wt.-% to 70 wt.-% of 2-hydroxypropyl octanoate, and 5 wt.-% to 15 wt.-% of 1,2-propanediol dioctanoate.

[0046] In some embodiments, the alkylene glycol ester may not include propylene glycol monoesters derived from propylene glycol components and fatty acids having 16 or more carbon atoms (such as palmitic acid). While not bound by any particular theory, it has been found that combinations of antimicrobial compounds and propylene glycol monoesters containing C16 fatty acids may not provide additive or synergistic benefits. Therefore, in some embodiments, the alkylene glycol esters used in the compositions described herein may be substantially free of propylene glycol monoesters containing C16 fatty acids (such as palmitic acid).

[0047] In one embodiment, the alkylene glycol ester comprises a propylene glycol ester, preferably propylene glycol octanoate, and particularly propylene glycol monooctanoate. In another embodiment, the alkylene glycol ester is a propylene glycol ester, such as propylene glycol octanoate or propylene glycol monooctanoate.

[0048] In one embodiment, the alkylene glycol ester comprises an alkylene glycol octanoate, such as selected from mono-alkylene glycol octanoate, dialkylene glycol octanoate, and mixtures thereof.

[0049] In one embodiment, the alkylene glycol ester is selected from alkylene glycol monoesters, alkylene glycol diesters and mixtures thereof, preferably from propylene glycol monoesters, propylene glycol diesters and mixtures thereof, and particularly from propylene glycol monooctanoate, propylene glycol dioctanoate and mixtures thereof.

[0050] In one embodiment, the alkylene glycol ester is a mixture of alkylene glycol monoester and alkylene glycol diester, comprising, based on the total weight of the alkylene glycol monoester and propylene glycol diester, at least 10 wt.-%, preferably at least 30 wt.-%, more preferably at least 50 wt.-%, still more preferably at least 60 wt.-%, and particularly at least 70 wt.-% of the alkylene glycol monoester. In another embodiment, the alkylene glycol ester is a mixture of monooctanoic acid alkylene glycol ester and dioctanoic acid alkylene glycol ester, comprising, based on the total weight of the monooctanoic acid alkylene glycol ester and dioctanoic acid propylene glycol ester, at least 10 wt.-%, preferably at least 30 wt.-%, more preferably at least 50 wt.-%, still more preferably at least 60 wt.-%, and particularly at least 70 wt.-% of the monooctanoic acid alkylene glycol ester. In one embodiment, the alkylene glycol ester is a mixture of propylene glycol monooctanoate and propylene glycol dioctanoate, comprising, based on the total weight of propylene glycol monooctanoate and propylene glycol dioctanoate, at least 10 wt.-%, preferably at least 30 wt.-%, more preferably at least 50 wt.-%, still more preferably at least 60 wt.-%, particularly at least 70 wt.-% of propylene glycol monooctanoate.

[0051] In one embodiment, the alkylene glycol ester comprises a mixture of at least one propylene glycol monooctanoate and propylene glycol dioctanoate. In one embodiment, based on the total weight of the alkylene glycol ester, the alkylene glycol ester comprises at least 50 wt.% of at least one propylene glycol monooctanoate, preferably at least 60 wt.% of at least one propylene glycol monooctanoate, more preferably at least 70 wt.% of at least one propylene glycol monooctanoate. In one embodiment, the at least one propylene glycol monooctanoate and propylene glycol dioctanoate are contained in the mixture in a weight ratio of about 15:1 to about 1:1, preferably about 10:1 to about 1:1, more preferably about 5:1 to about 2:1.

[0052] The weight ratio of the alkylene glycol ester to the at least one antimicrobial compound can vary depending on a variety of factors. For example, the weight ratio may depend on the composition of the final product, the microorganism to be controlled, the specific alkylene glycol ester and antimicrobial compound used, the final properties of the product, etc. The weight ratio of the alkylene glycol ester to the at least one antimicrobial compound can, for example, range from about 1:50,000 to about 500:1, for example from about 1:10,000 to about 400:1, for example from about 1:5,000 to about 200:1, for example from about 1:2,500 to about 100:1, for example from about 1:1,500 to about 50:1, for example from about 1:1,000 to 30:1. In many applications, only a small amount of the alkylene glycol ester is required to enhance the efficacy of the at least one antimicrobial compound. For example, in one aspect, the at least one antimicrobial compound is present in a larger amount than the alkylene glycol ester. In some embodiments, the weight ratio of the alkylene glycol ester to the at least one antimicrobial compound can be from about 1:5,000 to about 4:1, for example, from about 1:1,500 to about 4:1, from about 1:300 to about 4:1, from about 1:20 to about 4:1, from about 1:15 to about 4:1, or from about 1:10 to about 4:1. In one embodiment, the at least one antimicrobial compound and the alkylene glycol ester are included in the antimicrobial composition in a weight ratio of 1:1 to 6:1. In one embodiment, the at least one antimicrobial compound and the alkylene glycol ester are included in the antimicrobial composition in a weight ratio of 1.1:1 to 3:1. In one embodiment, the at least one antimicrobial compound and the alkylene glycol ester are included in the antimicrobial composition in a weight ratio of 1.2:1 to 2:1.

[0053] In one embodiment, the alkylene glycol ester and the antimicrobial compound are present in a synergistically effective weight ratio.

[0054] In one embodiment, the alkylene glycol ester and the antimicrobial compound are present in a weight ratio of about 1:1000 to about 2000:1, or about 1:1000 to about 1500:1, or about 1:1000 to about 500:1, or about 1:1000 to about 50:1, or about 1:800 to about 200:1, or about 1:800 to about 40:1, or about 1:600 ​​to about 150:1, or about 1:600 ​​to about 30:1, or about 1:550 to about 100:1, or about 1:550 to about 20:1. In another embodiment, the alkylene glycol ester and the antimicrobial compound are present in a weight ratio of about 1:500 to about 2000:1, or about 1:200 to about 2000:1, or about 1:50 to about 1500:1, or about 1:10 to about 1300:1.

[0055] Salts of citric acid, salicylic acid, levulinic acid, anisic acid, and phytic acid can be any salt known in the art. Suitable cation counterions are, for example, ions of alkali metals (preferably lithium, sodium, and potassium), alkaline earth metals (preferably calcium, magnesium, and barium), and transition metals (preferably manganese, copper, silver, zinc, and iron), as well as ammonium (NH4+) and substituted ammonium, wherein one to four hydrogen atoms are replaced by C1-C4-alkyl, C1-C4-hydroxyalkyl, C1-C4-alkoxy, C1-C4-alkoxy-C1-C4 alkyl, hydroxyC1-C4-alkoxy-C1-C4-alkyl, phenyl, or benzyl. Suitably, the salts of said acids are sodium salts, for example, the salt of salicylic acid is sodium salicylate.

[0056] In one embodiment, the at least one antimicrobial compound is selected from citric acid and its salts, salicylic acid and its salts, gluconolactone, levulinic acid and its salts, ethyl levulinate, butyl levulinate, ethylhexylglycerin, ethylene glycol, 1,3-propanediol, 1,3-butanediol, 2,3-propanediol, 1,2-pentanediol, 1,2-hexanediol, octyl glycol, ethyl lactate, butyl lactate, clomiphene, 1,2-decanediol, 4-hydroxyacetophenone, octyl... Hydroxamic acid and its salts, caprylic acid glyceride, chlorphenesin, triclosan, methylheptylglycerol, polyglycerol-2, 3, 4, 6, or 10-caprylate, polyglycerol-2, 3, 4, 6, or 10-decanoate / caprylate, azelaic acid, vitamin C, zinc oxide, zinc citrate, zinc pyrrolidone carboxylate (PCA zinc), zinc glycinate, nicotinamide, hyaluronic acid, 2-methyl-5-cyclohexylpentanol, aluminum sulfate, aluminum zirconium, aluminum chloride, hydrated aluminum chloride, and benzoyl peroxide.

[0057] In one embodiment, the at least one antimicrobial compound is selected from citric acid and its salts, salicylic acid and its salts, gluconolactone, levulinic acid and its salts, ethyl levulinate, butyl levulinate, ethylhexylglycerol, ethylene glycol, 1,3-propanediol, 1,3-butanediol, 2,3-propanediol, 1,2-pentanediol, 1,2-hexanediol, octanediol, ethyl lactate, methylheptylglycerol, zinc glycinate, and butyl lactate, such as citric acid and sodium salicylate.

[0058] In one embodiment, the at least one antimicrobial compound is selected from levulinic acid and its salts, ethyl levulinate and butyl levulinate, for example selected from levulinic acid, ethyl levulinate and butyl levulinate, preferably levulinic acid.

[0059] In one embodiment, the at least one antimicrobial compound is selected from ethylene glycol, 1,3-propanediol, 1,3-butanediol, 2,3-butanediol, 1,2-pentanediol, 1,2-hexanediol, and octanediol.

[0060] In one embodiment, at least one antimicrobial compound is selected from ethyl lactate and butyl lactate.

[0061] In one embodiment, the at least one antimicrobial compound is selected from ethyl levulinate, butyl levulinate, ethyl lactate, and butyl lactate.

[0062] In one embodiment, at least one antimicrobial compound is selected from citric acid and its salts, salicylic acid and its salts, and levulinic acid and its salts, for example selected from citric acid, sodium salicylate, and levulinic acid, preferably selected from citric acid and levulinic acid.

[0063] In one embodiment, the alkylene glycol ester is propylene glycol octanoate (PGC), for example selected from propylene glycol monooctanoate, propylene glycol dioctanoate, and mixtures thereof, and the antimicrobial compound is citric acid, wherein the PGC and the citric acid are present in a weight ratio of about 1:32 to about 200:1.

[0064] In one embodiment, the alkylene glycol ester is propylene glycol octanoate (PGC), for example selected from propylene glycol monooctanoate, propylene glycol dioctanoate, and mixtures thereof, and the antimicrobial compound is sodium salicylate, wherein the PGC and the sodium salicylate are present in a weight ratio of about 1:128 to about 20:1.

[0065] In one embodiment, the alkylene glycol ester is propylene glycol octanoate (PGC), for example selected from propylene glycol monooctanoate, propylene glycol dioctanoate, and mixtures thereof, and the antimicrobial compound is gluconolactone, wherein the PGC and the gluconolactone are present in a weight ratio of about 1:128 to about 80:1.

[0066] In one embodiment, the alkylene glycol ester is propylene glycol octanoate (PGC), for example selected from propylene glycol monooctanoate, propylene glycol dioctanoate, and mixtures thereof, and the antimicrobial compound is levulinic acid, ethyl levulinate, or butyl levulinate, and wherein the PGC and the levulinic acid, ethyl levulinate, or butyl levulinate are present in a weight ratio of about 1:256 to about 5:1.

[0067] In a preferred embodiment, the antimicrobial compound is levulinic acid, and is selected from propylene glycol monooctanoate, propylene glycol dioctanoate, and mixtures thereof, and the alkylene glycol ester and the levulinic acid are present in a weight ratio of about 1:256 to about 5:1.

[0068] In a preferred embodiment, the alkylene glycol ester comprises a mixture of 2-hydroxy-1-methylethyl octanoate, 2-hydroxypropyl octanoate, and 1,2-propanediol dioctanoate, and the at least one antimicrobial compound comprises levulinic acid. In a preferred embodiment, the mixture of 2-hydroxy-1-methylethyl octanoate, 2-hydroxypropyl octanoate, and 1,2-propanediol dioctanoate is included in the antimicrobial composition with levulinic acid in a weight ratio of about 1:256 to about 5:1.

[0069] In another embodiment, the antimicrobial compound is ethyl levulinate or butyl levulinate, and wherein the PGC and the ethyl levulinate or butyl levulinate are present in a weight ratio of about 1:256 to about 1:1.

[0070] In one embodiment, the alkylene glycol ester is propylene glycol octanoate (PGC), for example selected from propylene glycol monooctanoate, propylene glycol dioctanoate, and mixtures thereof, and the antimicrobial compound is ethylhexylglycerin, wherein the PGC and the ethylhexylglycerin are present in a weight ratio of about 1:32 to about 4:1.

[0071] In one embodiment, the alkylene glycol ester is propylene glycol octanoate (PGC), for example selected from propylene glycol monooctanoate, propylene glycol dioctanoate, and mixtures thereof, and the antimicrobial compound is octanediol, 1,2-pentanediol, or 1,2-hexanediol, and wherein the PGC and the octanediol, 1,2-pentanediol, or 1,2-hexanediol are present in a weight ratio of about 1:256 to about 5:1. Preferably, the antimicrobial compound is octanediol, and wherein the PGC and the octanediol are present in a weight ratio of about 1:8 to about 5:1; or wherein the antimicrobial compound is 1,2-pentanediol, and wherein the PGC and the 1,2-pentanediol are present in a weight ratio of about 1:256 to about 2:13; or wherein the antimicrobial compound is 1,2-hexanediol, and wherein the PGC and the 1,2-hexanediol are present in a weight ratio of about 1:128 to about 4:13.

[0072] In one embodiment, the alkylene glycol ester is propylene glycol octanoate (PGC), for example selected from propylene glycol monooctanoate, propylene glycol dioctanoate, and mixtures thereof, and the antimicrobial compound is ethylene glycol, 1,3-propanediol, or 1,3-butanediol, and wherein the PGC and the ethylene glycol, 1,3-propanediol, 1,3-butanediol, or 2,3-butanediol are present in a weight ratio of about 1:256 to about 10:1, preferably wherein the antimicrobial compound is ethylene glycol, and wherein the PGC and the ethylene glycol are present in a weight ratio of about 1:256 to about 10:1, or wherein the antimicrobial compound is The antimicrobial compound is 1,3-propanediol, and wherein the PGC and the 1,3-propanediol are present in a weight ratio of about 1:128 to about 5:1; or wherein the antimicrobial compound is 1,3-butanediol, and wherein the PGC and the 1,3-butanediol are present in a weight ratio of about 1:128; or wherein the antimicrobial compound is 2,3-propanediol, and wherein the PGC and the 2,3-propanediol are present in a weight ratio of about 1:128 to about 5:1; or wherein the antimicrobial compound is 2,3-butanediol, and wherein the PGC and the 2,3-butanediol are present in a weight ratio of about 1:128.

[0073] In one embodiment, the alkylene glycol ester is propylene glycol octanoate (PGC), for example selected from propylene glycol monooctanoate, propylene glycol dioctanoate, and mixtures thereof, and the antimicrobial compound is ethyl lactate or butyl lactate, wherein the PGC and the ethyl lactate or butyl lactate are present in a weight ratio of about 1:512 to about 1:1, preferably wherein the antimicrobial compound is ethyl lactate. Alternatively, the antimicrobial compound may be butyl lactate, and the PGC and butyl lactate may be present in a weight ratio of about 1:128 to about 1:1.

[0074] In one embodiment, the alkylene glycol ester is propylene glycol octanoate (PGC), for example selected from propylene glycol monooctanoate, propylene glycol dioctanoate, and mixtures thereof, and the antimicrobial compound is methylheptylglycerol, wherein the PGC and the methylheptylglycerol are present in a weight ratio of about 1:4 to about 32:1.

[0075] In one embodiment, the alkylene glycol ester is propylene glycol octanoate (PGC), for example selected from propylene glycol monooctanoate, propylene glycol dioctanoate, and mixtures thereof, and the antimicrobial compound is zinc glycinate, wherein the PGC and the zinc glycinate are present in a weight ratio of about 2:1 to about 500:1.

[0076] In one embodiment, the alkylene glycol ester is propylene glycol octanoate (PGC), for example selected from propylene glycol monooctanoate, propylene glycol dioctanoate, and mixtures thereof, and the antimicrobial compound is zinc pyrrolidone carboxylate, wherein the PGC and the zinc pyrrolidone carboxylate are present in a weight ratio of about 1:1 to about 2000:1.

[0077] In one embodiment, the alkylene glycol ester is propylene glycol octanoate (PGC), for example selected from propylene glycol monooctanoate, propylene glycol dioctanoate, and mixtures thereof, and the antimicrobial compound is hyaluronic acid, wherein the PGC and the hyaluronic acid are present in a weight ratio of about 1:1 to about 1250:1.

[0078] In one embodiment, the alkylene glycol ester is propylene glycol octanoate (PGC), for example selected from propylene glycol monooctanoate, propylene glycol dioctanoate, and mixtures thereof, and the antimicrobial compound is glycolic acid, wherein the PGC and the glycolic acid are present in a weight ratio of about 1:8 to about 1:1.

[0079] In one embodiment, the alkylene glycol ester is propylene glycol octanoate (PGC), for example selected from propylene glycol monooctanoate, propylene glycol dioctanoate, and mixtures thereof, and the antimicrobial compound is nonanoic acid, wherein the PGC and the nonanoic acid are present in a weight ratio of about 1:1 to 8:1.

[0080] In one embodiment, the antimicrobial composition comprises

[0081] (i) at least one antimicrobial compound, such as levulinic acid; and

[0082] (ii) A mixture of 2-hydroxy-1-methyl ethyl octanoate, 2-hydroxypropyl octanoate, and 1,2-propanediol dioctanoate.

[0083] In one embodiment, the antimicrobial composition comprises

[0084] (i) about 10 to about 90 wt.% of at least one antimicrobial compound, such as levulinic acid; and

[0085] (ii) about 10 to about 80 wt.% of the alkylene glycol ester, preferably derived from (a) an alkylene glycol and (b) a fatty acid having about 6 to 14 carbon atoms; wherein the amount is based on the total weight of the antimicrobial composition.

[0086] In one embodiment, the antimicrobial composition comprises

[0087] (i) about 10 to about 90 wt.% of at least one antimicrobial compound, such as levulinic acid; and

[0088] (ii) a mixture of about 10 to about 80 wt.% of 2-hydroxy-1-methylethyl octanoate, 2-hydroxypropyl octanoate and 1,2-propanediol dioctanoate; wherein the amount is based on the total weight of the antimicrobial composition.

[0089] In some embodiments, the antimicrobial compositions disclosed herein may have a pH of about 2 to about 11, for example about 3 to about 10, particularly about 3 to about 8.

[0090] This invention also relates to end-use formulations comprising the antimicrobial composition according to the invention. As described above, the amount of the at least one antimicrobial compound used in the end-use formulations of the invention varies depending on the specific at least one antimicrobial compound. In an alternative embodiment, the at least one antimicrobial compound may be formulated as an antimicrobial concentrate. "Antimicrobial concentrate" or "antimicrobial composition" refers to a composition to be added to the end-use formulation in a specified amount. In the antimicrobial concentrate, the amount of the at least one antimicrobial compound will be higher than the final amount formulated in the final product. In some embodiments, the antimicrobial concentrate may contain only the at least one antimicrobial compound and the alkylene glycol ester. Alternatively, in some embodiments, the antimicrobial concentrate may contain at least one antimicrobial compound, the alkylene glycol ester, and a carrier compatible with the end-use formulation. Exemplary carriers include, for example, water, aqueous solvents, or other solvents acceptable for the use of the end-use formulation and these formulations. The antimicrobial concentrate may be added to the end-use formulation in an amount required to achieve the desired amount of the at least one antimicrobial compound in the end-use formulation.

[0091] When included in an antimicrobial concentrate, the at least one antimicrobial compound and the alkylene glycol ester can be combined with a variety of different components. For example, in one embodiment, the antimicrobial concentrate may contain a solvent. The solvent may be a polar solvent, such as water, or a water-miscible solvent, such as an alcohol and / or glycol ether. In some embodiments, the antimicrobial composition may also include a water-miscible organic solvent. Examples of suitable water-miscible solvents include ethanol, propanol, benzyl alcohol, isopropanol, diethylene glycol propyl ether, ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, ethylene glycol monopropyl ether, ethylene glycol monoisopropyl ether, ethylene glycol monobutyl ether, diethylene glycol monomethyl ether, diethylene glycol monobutyl ether, diethylene glycol monoethyl ether, diethylene glycol monon-butyl ether, diethylene glycol dimethyl ether, ethylene glycol diethyl ether, ethylene glycol dibutyl ether, propylene glycol n-butyl ether, tripropylene glycol methyl ether, dipropylene glycol methyl ether, dipropylene glycol butyl ether, and combinations thereof.

[0092] In other embodiments, one or more alkylene glycol esters and at least one antimicrobial compound may be added to the end-use formulation independently of each other. For example, in some embodiments, the alkylene glycol ester may be added to at least one antimicrobial compound before the at least one antimicrobial compound is added to the end-use formulation. In still other embodiments, the alkylene glycol ester may be added to the end-use formulation after the at least one antimicrobial compound is added to the end-use formulation. In some embodiments, the alkylene glycol ester may be added to the end-use formulation as a separate component along with at least one antimicrobial compound.

[0093] As described above, in a third aspect, the present invention relates to end-use formulations comprising the antimicrobial composition according to the invention, preferably home care or personal care products.

[0094] The embodiments of the corresponding antimicrobial compositions have been described above and are also applicable to end-use formulations, such as home care or personal care products. Further embodiments are described below.

[0095] In some embodiments, the antimicrobial composition of the present invention may be added to the end-use formulation (e.g., a home care or personal care product) in an amount of 0.01% to about 10% by weight of the formulation. More specifically, in some embodiments, the amount of antimicrobial composition added is about 0.1% to 5.0% by weight of the formulation. The amount of antimicrobial composition added may depend on the antimicrobial compound selected.

[0096] In one embodiment, the antimicrobial composition has a weight percentage of 0.02% to 10% based on the total weight of the end-use formulation (e.g., home care or personal care product).

[0097] In one embodiment, the alkylene glycol ester contained in the antimicrobial composition is present in the end-use formulation (e.g., home care or personal care product) in an amount of 10 wt.-% or less, such as 5 wt.-% or less, based on the weight of the end-use formulation (e.g., home care or personal care product).

[0098] In one embodiment, the at least one antimicrobial compound contained in the antimicrobial composition is present in the end-use formulation (e.g., home care or personal care product) in an amount of 10 wt.-% or less, such as 5 wt.-% or less, based on the weight of the end-use formulation (e.g., home care or personal care product).

[0099] In one embodiment, the antimicrobial composition is levulinic acid or a salt thereof, ethyl levulinate or butyl levulinate, preferably said antimicrobial compound is levulinic acid.

[0100] Generally, the antimicrobial compositions of the present invention can be incorporated into any number of different end-use formulations or products. As used herein, “end-use formulation” or “end-use product” is intended to refer to personal care products, including cosmetics, home care products, and health and hygiene products.

[0101] In one implementation, personal care products are selected from shampoos, skin lotions, shower gels, deodorants, bubble baths, bath oils, creams, baby products, liquid soaps, hair gels, conditioners, hair conditioning masks, hair styling products, cosmetics, sunscreens, color cosmetics, toothpaste, mouthwash, and wipes.

[0102] For example, personal care products may include products such as cosmetic formulations, including creams, makeup removers, mascaras, or wipes. Personal care product formulations also include shampoos, conditioners, body lotions, or liquids for any personal care wet wipe application. Personal care product formulations may include any product for topical application to a user's skin or hair. When the antimicrobial compositions disclosed herein are formulated into personal care products, the antimicrobial compositions provide effective broad-spectrum antimicrobial activity over a wide pH range. For example, in some embodiments, the personal care products may have a pH of about 2 to 11, such as about 3 to about 10, particularly about 3 to about 8. Therefore, the antimicrobial compositions disclosed herein can exhibit broad antimicrobial coverage over a range of end-use products having a pH spectrum.

[0103] Personal care product formulations may comprise a base formulation into which the antimicrobial composition of the present invention is incorporated. The base formulation may contain a variety of different ingredients, depending on the end-use application. For example, personal care product formulations may contain solvents, surfactants, emulsifiers, consistency factors, conditioning agents, emollients, skin care ingredients, humectants, thickeners, moisturizers, fillers, antioxidants, preservatives, active ingredients, particularly dermatologically active ingredients, fragrances, etc., and mixtures thereof. Active ingredients mentioned herein include, for example, agents such as anti-inflammatory agents, antibacterial agents, and antifungal agents. Active ingredients suitable for topical application are particularly preferred.

[0104] Suitable surfactants include: alkyl sulfates, such as sodium lauryl sulfate and ammonium lauryl sulfate; sodium cetearyl sulfate; alkyl sulfonate salts, such as sodium lauryl sulfonate; alkyl ether sulfates, such as sodium lauryl polyoxyethylene ether sulfate; sodium tridecyl polyoxyethylene ether sulfate; sodium oleyl polyether sulfate; ammonium lauryl polyoxyethylene ether sulfate; alkyl ether sulfosuccinates, such as disodium lauryl polyoxyethylene ether sulfosuccinate; alkyl glycosides, such as decyl glucoside; lauryl... Glucosides; alkyl hydroxyethyl sulfonate amphoteric surfactants, such as cocamidopropyl betaine; sodium cocamidopropyl acetate; sodium lauroyl amphoteric acetate; disodium lauroyl diacetate; disodium cocamidopropyl acetate; sodium lauroyl amphoteric propionate; disodium lauroyl dipropionate; potassium or ammonium salts of the above amphoteric surfactants; octanoyl / decanoyl amphoteric betaine; undecenoyl amphoteric betaine; lauroyl amphoteric betaine; and fatty alcohol polyethylene glycol ethers.

[0105] Suitable emulsifiers include, for example, anionic surfactants such as fatty acid salts, such as sodium stearate or sodium palmitate; organic soaps such as mono-, di-, or triethanolaminoeate; sulfonated or sulfonated compounds such as sodium lauryl sulfate or sodium cetyl sulfonate; saponins; lamepone; cationic surfactants such as quaternary ammonium salts; nonionic surfactants such as fatty alcohols, fatty acid esters having saturated or unsaturated fatty acids, polyoxyethylene esters or polyoxyethylene ethers of fatty acids, polymers of ethylene oxide and propylene oxide or propylene glycol; amphoteric surfactants such as phospholipids; proteins such as gelatin; casein alkyl amide betaine, alkyl betaine and amphoteric glycinate; alkyl phosphates, alkyl polyoxyethylene phosphates or corresponding acids; and siloxane derivatives such as alkyl polydimethylsiloxane copolyols.

[0106] Suitable consistency factors include, for example, fatty alcohols or mixtures thereof with fatty acid esters, such as acetylated lanolin alcohol, aluminum stearate, carbomer, cetyl alcohol, glyceryl oleate, glyceryl stearate, glyceryl stearate (and) PEG 100 stearate, magnesium stearate, magnesium sulfate, oleic acid, stearic acid, stearyl alcohol, myristyl myristate, isopropyl palmitate, beeswax and its synthetic equivalents, carbomer, etc. Suitable conditioning agents are, for example, alkylaminolactic acid ammonium, hexadecyltrimethylammonium chloride and distearylethylhydroxyethylmethylammonium sulfate and cetearyl alcohol, cetyl polydimethylsiloxane, castor oil cetyl ester, polydimethylsiloxane, lauryl ether-23, lauryl ether-4, polydecene, retinyl palmitate, quaternized protein hydrolysate, quaternized cellulose and starch derivatives, quaternized copolymers of acrylic acid or methacrylic acid or their salts, and quaternized siloxane derivatives.

[0107] Suitable emollients include, for example, cetearyl isononanoate, cetearyl caprylate, decyl oleate, isooctyl stearate, cocoyl caprylate / caprylate, ethylhexyl hydroxystearate, ethylhexyl isononanoate, isopropyl isostearate, isopropyl myristate, oleic acid ester, hexyl laurate, liquid paraffin, PEG-75 lanolin, PEG-7 glyceryl cocoate, petrolatum, ceresin, cyclomethicone, dimethicone, dimethicone copolyol, dioctyl ether, shea butter (butyrospermum parkii), jojoba oil (buxus chinensis), low-erucic acid rapeseed oil (canola), carnauba wax (carnauba cera), copernicia cerifera wax (copernicia cerifera), evening primrose oil (oenotherabiennis), oil palm oil (elaeis guineensis), sweet almond seed oil (prunus) Dulcis, squalane, corn silk germ oil (zea mays), wild soybean seed extract (glycinesoja), sunflower seed oil (helianthus annuus), lanolin, hydrogenated castor oil, hydrogenated coconut oil, hydrogenated polyisobutylene, sucrose cocoate, stearoxy polydimethylsiloxane, lanolin alcohol, isohexadecane.

[0108] Suitable skincare ingredients include, for example, plant extracts, bisabolol, anti-inflammatory agents, urea, allantoin, panthenol and panthenol derivatives, phytanetriol, vitamins A, E, C, and D, ceramides of animal or plant origin, lecithin, etc.

[0109] Suitable humectants include, for example, butylene glycol, cetyl alcohol, polydimethylsiloxane, dimyristyl tartrate, glucosyl glycerol polyether-26, glycerin, glyceryl stearate, hydrolyzed milk protein, lactic acid, lactose and other sugars, lauryl ether-8, lecithin, octyloxyglycerol, PEG-12, PEG 135, PEG-150, PEG-20, PEG-8, pentylene glycol, hexanediol, phytanetriol, polyquaternium-39 PPG-20 methyl glucosyl ether, propylene glycol, sodium hyaluronate, sodium lactate, sodium PCA, sorbitol, succinosyl polysaccharide, synthetic beeswax, tri-C14-15 alkyl citrate, and starch.

[0110] Suitable thickeners include, for example, acrylate / stearyl alcohol polyether-20 methacrylate copolymer, carbomer, carboxymethyl starch, beeswax, polydimethylsiloxane / vinyl polydimethylsiloxane crosspolymer, propylene glycol alginate, hydroxyethyl cellulose, hydroxypropyl methylcellulose, silica, silica dimethyl silyl alkylate, xanthan gum, and hydrogenated butene / ethylene / styrene copolymer.

[0111] Suitable humectants include, for example, adipic acid, fumaric acid and its salts, benzoic acid and its salts, triacetin, sodium lauryl sulfate or magnesium lauryl sulfate, magnesium stearate, solid polyethylene glycol, polyvinylpyrrolidone, boric acid, monolaurate or monopalmitate, myristic acid, cetyl alcohol, cetearyl alcohol, talc, calcium or magnesium salts of higher fatty acids, mono-, di- or triglycerides of higher fatty acids, and polytetrafluoroethylene.

[0112] Suitable antioxidants include, for example, sulfites such as sodium sulfite, tocopherol or its derivatives, ascorbic acid or its derivatives, citric acid, propyl gallate, chitosan glycolate, cysteine, N-acetylcysteine ​​plus zinc sulfate, thiosulfates such as sodium thiosulfate, polyphenols, etc.

[0113] Suitable preservatives may include, for example, acids, esters, ethers and their salts, ketones, phenolic compounds, sulfites and chelating agents, aromatic alcohols, quaternary ammonium compounds, aldehydes, pyranone compounds, urea compounds, imidazole compounds, isothiazolinones, amines, amides, halogen compounds and combinations thereof.

[0114] In one embodiment, the preservative may be an acid compound, including aromatic and non-aromatic acids. Exemplary acids include, for example, benzoic acid, propionic acid, salicylic acid, sorbic acid, formic acid, undecanoic acid, lactic acid, citric acid, and glycolic acid. Salts of these acids and esters of these acids may also be used. Examples of salts include sodium benzoate and potassium sorbate. Other salts may also be used. Acid compounds are typically used as preservatives in end-use formulations in amounts up to about 3% by weight, depending on the specific acid compound. Esters and salts may be used in similar amounts. In most cases and under the circumstances of use, the amount of the acid, its ester, or salt thereof is up to about 1% by weight, and more typically up to about 0.6% by weight. Mixtures of acids may also be used as preservatives.

[0115] In another embodiment, the preservative may be an aldehyde. Exemplary aldehydes include, for example, formaldehyde and paraformaldehyde. Exemplary aldehyde forming agents include imidazolidinyl compounds, such as hydantoin, for example dimethyloldimethylhydantoin (DMDMH), and other similar aldehyde-forming hydantoin. Depending on the application, the aldehyde may be present in the composition to be preserved in an amount of up to 0.3% by weight. Typically, the amount of aldehyde is up to 0.2% based on the weight of the composition to be preserved. Mixtures of aldehydes are also used as preservatives.

[0116] In a further embodiment, the preservative may be a phenolic compound. Exemplary phenolic compounds include, for example, parabens, biphenyl-2-ol (o-phenylphenol) or salts thereof, 4-chloro-m-cresol, 4-chloro-3,5-dimethylphenol, 4-isopropyl-m-cresol, 2-benzyl-4-chlorophenol, 2-phenoxyethyl-1-ol, chlorophenoxyethanol, 3-phenylpropanol, 2-phenylethanol, and bromochlorophenol. Exemplary parabens include, for example, butyl paraben, propyl paraben, ethyl paraben, methyl paraben, and salts thereof, including, for example, potassium, sodium, and / or calcium salts. Based on the total weight of the end-use formulation, phenolic compounds are typically used as preservatives in the end-use formulation in an amount of up to about 1% by weight. This upper limit depends on the specific phenolic compound. More generally, up to about 0.5% by weight of phenolic compounds are used in cosmetic formulations.

[0117] In yet another embodiment, the preservative may be a compound called a chelating agent, such as an iron chelating agent. Exemplary iron chelating agents include pyridinethiones and compounds such as pyrrolidone ethanolamine or hydroxypyridines and their salts. Pyridinethions are known by several names, including 2-mercaptopyridine-N-oxide; 2-pyridinethiol-1-oxide (CAS Registry No. 1121-31-9); 1-hydroxypyridine-2-thione and 1-hydroxy-2(1H)-pyridinethione (CAS Registry No. 1121-30-8); 2-pyridineol-1-oxide (HPNO) and N-hydroxy-6-octoxypyridine 2(1H)-one and 1-hydroxy-6-octoxypyridine 2(1H)-one ethanolamine salts. Pyridinethione salts are commercially available from Arxada AG, such as Sodium OMADINE® or ZincOMADINE®.

[0118] Pyrithiones as preservatives can exist in either water-insoluble or water-soluble forms. Pyrithiones may include sodium pyrithione, zinc pyrithione, barium pyrithione, strontium pyrithione, copper pyrithione, cadmium pyrithione, and / or zirconium pyrithione. Other pyrithiones that may be present in the composition include sodium pyrithione, bismuth pyrithione, potassium pyrithione, lithium pyrithione, ammonium pyrithione, calcium pyrithione, magnesium pyrithione, silver pyrithione, gold pyrithione, manganese pyrithione, and / or organic amine pyrithiones. A single pyrithione may be present as a preservative, or a combination of any of the above substances may be included as a preservative.

[0119] Iron chelating compounds are typically used as preservatives in end-use formulations at a maximum of about 1% by weight, depending on the specific compound. Of particular interest are zinc pyrithione and pyrrolidone ethanolamine. These iron chelating agents may also offer other advantages, such as anti-dandruff properties.

[0120] In another embodiment, the preservative may include inorganic sulfite compounds and bisulfite compounds. The sulfite compound is typically present in an amount of up to about 0.5% by weight, based on the total weight of the final-use formulation.

[0121] In some embodiments, the preservative comprises an alcohol compound. The alcohol may be a lower alcohol or an aromatic alcohol. Lower alcohols are typically selected from monofunctional low-molecular-weight alcohols, preferably alkanols having 1 to 4 carbon atoms, such as methanol, ethanol, isopropanol, or butanol, or combinations thereof. Substituted alcohols, such as chlorobutanol, may also be used. Particularly suitable lower alcohols include ethanol and isopropanol. Aromatic alcohols may also be used. Suitable aromatic alcohols include phenoxyethanol, 2,4-dichlorophenylmethanol, benzyl alcohol, 1-phenoxypropanol, chlorophenylglycerol ether, and benzyl hemiacetal. A particularly preferred alcohol is phenoxyethanol. The alcohol compound may be used as a preservative in the end-use formulation in an amount up to about 1.5% by weight based on the total weight of the end-use formulation, depending on the specific alcohol compound. In most cases, the amount of the alcohol compound is typically up to about 1% by weight, more typically up to about 0.5% by weight, based on the weight of the end-use formulation.

[0122] In another embodiment, one or more quaternary ammonium compounds may be used as preservatives. Quaternary ammonium compounds, also known as "quaternary ammonium compounds (quats)," typically contain at least one quaternary ammonium cation having a suitable anion. Quaternary ammonium salts typically have the general formula (1).

[0123] (1)

[0124] Groups R1, R2, R3, and R4 can vary over a wide range and possess antimicrobial properties. Typically, at least one, such as at least two, of R1, R2, R3, and R4 is a lower alkyl group, meaning having 1 to 4 carbon atoms, such as methyl, ethyl, propyl, or butyl. In one aspect, at least one, such as at least two, of R1, R2, R3, and R4 is a longer-chain alkyl group with 6 to 24 carbon atoms. R4 can also be a substituted or unsubstituted benzyl group, such as ethylbenzyl, or an alkoxy group. - It is a monovalent anion or a polyvalent anion of inorganic or organic acids. A - Suitable anions are, in principle, all inorganic or organic anions, especially halide ions (such as chloride or bromide ions), carbonate ions, bicarbonate ions, carboxylate ions, sulfonate ions, phosphate ions, propionate ions, saccharin ions, or mixtures thereof. Carboxylates can be derived from lower carboxylic acids or fatty acids.

[0125] In the following text, alkyl refers in each case to unbranched or branched alkyl groups having a specified number of carbon atoms, but unbranched alkyl groups are preferred, and particularly those having an even number of carbon atoms. In particular, this also includes homologues derived from natural sources, such as "cocoyl alkyl".

[0126] In one embodiment, the quaternary ammonium compound may have the following R groups: R1, R2, and R3 are alkyl groups, and R4 is benzyl, C 1-18 Alkyl groups, such as C 6-18 Alkyl or alkoxy groups, for example, have the structure -[(CH2)2-O] n The group R5, wherein n = 1-20 and R5 is hydrogen or an unsubstituted or substituted phenyl group, and A- is, as described above, a monovalent anion or an equivalent polyvalent anion of an inorganic or organic acid. For example, R1 is an alkyl group having 1 to 4 carbon atoms, and R2 and R3 are independently alkyl groups having 6 to 24 carbon atoms, or R1 and R2 are independently alkyl groups having 1 to 4 carbon atoms, and R3 is an alkyl group having 6 to 24 carbon atoms.

[0127] Suitable quaternary ammonium compounds include, for example, alkyl (C 12-22 Trimethylammonium bromide, alkyl (C 12-22 Trimethylammonium chloride compounds, including, for example, hexadecyltrimethylammonium bromide, hexadecyltrimethylammonium chloride, lauryltrimethylammonium bromide, lauryltrimethylammonium chloride, stearyltrimethylammonium bromide and stearyltrimethylammonium chloride or mixtures thereof, and benzalkonium compounds (including, for example, benzalkonium chloride, benzalkonium bromide and benzalkonium saccharin).

[0128] In one embodiment, the quaternary ammonium compound may comprise a dialkylammonium compound, such as a dimethyl dialkylammonium compound. In one embodiment, the dimethyl dialkylammonium compound may have about 8 to about 12 carbon atoms, for example, about 8 to about 10 carbon atoms, in each alkyl group.

[0129] Examples of dimethyldialkylammonium compounds include dimethyldioctylammonium compounds such as dimethyldioctylammonium chloride, and dimethyldidecylammonium compounds such as dimethyldidecylammonium chloride. Mixtures of dimethyldialkylammonium compounds may also be used, and other anions, such as those described above, may also be used. Commercially available dimethyldialkylammonium compounds include, for example, compositions marketed and sold by Arxada AG under the trade names BARDAC®, BARDAP®, BARQUAT®, or CARBOQUAT®.

[0130] Commercially available examples of dimethyl dialkylammonium compounds include dioctyl dimethylammonium chloride (available from Arxada AG as Bardac® LF and LF-80), octyldecyl dimethylammonium chloride (available from Arxada AG as Bardac® 2050 and 2080 as a mixture of octyldecyl dimethylammonium chloride, dioctyl dimethylammonium chloride and didecyl dimethylammonium chloride), didecyl dimethylammonium chloride (available from Arxada AG as Bardac® 2250 and 2280), decyl isononyl dimethylammonium chloride (available from Arxada AG as Bardac® 21), diisodecyl dimethylammonium chloride (available from Stepan Co., Northfield, III. as BTC 99), and any combination of the foregoing substances.

[0131] Based on the total weight of the end-use formulation, the quaternary ammonium compound may be included in the end-use formulation in an amount of up to about 0.2% by weight, depending on the specific quaternary ammonium compound. In some embodiments, the end-use formulation may contain about 0.1% by weight to about 0.05% by weight, based on the weight of the end-use formulation.

[0132] Exemplary pyranone compounds that can be used as preservatives in this invention include, for example, dehydroacetic acid and its salts. Based on the total weight of the end-use formulation, a pyranone compound may be used in an amount of up to about 1.0% by weight. In some embodiments, one or more pyranone compounds may be used in an amount of up to about 0.6% by weight.

[0133] In some embodiments, the preservative may include one or more isothiazolinones. Exemplary isothiazolinones include, for example, 5-chloro-2-methyl-isothiazolinone (chloromethylisothiazolinone), 2-methyl-isothiazolinone (methylisothiazolinone), benzisothiazolinone, and mixtures thereof. In some embodiments, one or more isothiazolinones may be used in an amount of up to about 0.01% by weight of the end-use formulation.

[0134] In some embodiments, one or more urea compounds may be used as preservatives. Exemplary urea compounds include, for example, 3-(4-chlorophenyl)-1-(3,4-dichlorophenyl)urea (triclocarban); 1,1'-methylenebis{3-[4-(hydroxymethyl)-2,5-dioxoimidazolidine-4-yl]urea}; and N-(hydroxymethyl)-N-(dihydroxymethyl-1,3-dioxo-2,5-imidazolidine-4)-N′-(hydroxymethyl)urea. These compounds are typically used in amounts of up to about 0.5% by weight in the end-use formulation.

[0135] Exemplary imidazole compounds that can be used as preservatives in this invention include, for example, 1-(4-chlorophenoxy)-1-(imidazol-1-yl)-3,3-dimethylbut-2-one; 1,3-bis(hydroxymethyl)-5,5-dimethylimidazolidine-2,4-dione. In some embodiments, the amount of one or more urea compounds that may be contained in the end-use formulation is up to about 0.5% by weight.

[0136] On another front, preservatives can be amine compounds, such as triamine compounds. Suitable triamine compounds include, but are not limited to, those having the following formula:

[0137]

[0138] Where R represents substituted or unsubstituted C8 to C9. 18 Alkyl, C8 to C 18 alkenyl, C8 to C 18 alkynyl or C8 to C 18 Cycloalkyl or aryl, and R is optionally separated by one or more heteroatoms.

[0139] As used herein, the term "substituted" includes compounds substituted with one or more of the following groups: halogens (e.g., F, Cl, I, or Br); heteroatomic groups; C8 to C9 groups. 18 Alkyl; C8 to C 18 Alkenyl; C8 to C 18 alkynyl group; C8 to C 18 cycloalkyl; aryl; or C8 to C9 containing a carbonyl group 18 Alkyl, C8 to C 18 alkenyl or C8 to C 18 Alkyne groups (such as ketones, esters, ethers, carbonates, or carboxylic esters).

[0140] Suitable heteroatoms include, but are not limited to, O, N, P, and S.

[0141] Suitable heteroatomic groups include, but are not limited to, -NH2, -NO2, -SO2, -SO3, -PO3, ═O, and -OH.

[0142] The substituent R is preferably unsubstituted C8 to C9. 18 Alkyl, C8 to C 18 alkenyl, C8 to C 18 alkynyl group, C8 to C 18 Cycloalkyl or aryl. Preferred triamines include, but are not limited to, N,N-bis(3-aminopropyl)-dodecylamine, which is available from Arxada AG as Lbac® 12. Bis(3-aminopropyl)octylamine and N,N-bis(3-aminopropyl)-octylamine.

[0143] The content of amine preservatives can typically be up to about 2% by weight of the final-use formulation, particularly about 50 ppm to about 200,000 ppm, for example about 50 ppm to about 500 ppm.

[0144] Other components that can be used as preservatives include dibromohexamidine and its salts; thimerosal; phenylmercuric salts; hexoteridin; 2-bromo-2-nitroprop-1,3-diol; 5-bromo-5-nitro-1,3-dioxane; polyhexamethylene biguanide or its salts; hexamethylenetetramine; methenamine 3-chloroallylochloride; 2-chloroacetamide; chlorhexidine and its diglucuronide, or its diacetate and dihydrochloride; 4,4-dimethyl,1,3-oxazolidine; glutaraldehyde; 5-ethyl-3,7-dioxa-1-azabicyclooctane; sodium hydroxymethylglycinate, iodo-2-propynyl butylcarbamate (IPBC), and ethyl lauroyl alginate. In some embodiments, these compounds may be used in an amount of up to about 0.5% by weight of the final-use article.

[0145] In addition, the preservative can be a single preservative, a mixture of two or more preservatives from a single type of preservative, or a mixture of two or more different types of preservatives.

[0146] Suitable preservatives are phenolic compounds, such as phenoxyethanol, bis(3-aminopropyl)dodecylamine, didecyldimethylammonium chloride, sodium benzoate, lactic acid, benzyl alcohol, benzisothiazolinone, sorbic acid and dehydroacetic acid, or their salts.

[0147] The formulations and compositions disclosed herein may further include active ingredients such as antimicrobial agents, anti-inflammatory agents, plant extracts, bisabolol, panthenol, tocopherol, active ingredients for anti-irritant, anti-dandruff applications, or anti-aging agents such as retinol, melibiose, etc. Other suitable active ingredients include, for example, medicinal dandelion (Medicago officinalis), Chinese kiwi fruit (Actinidia chinensis), allantoin, Aloe barbadensis, Anona cherimolia, Anthemis nobilis, peanut (Arachis hypogaea), arnica (Arnica Montana), wild oats (Avena sativa), beta-carotene, bisabolol, borage (Borago officinalis), butylene glycol, calendula officinalis, Camellia sinensis, camphor, Candida bombicola, capryloyl glycine, papaya (Carica papaya), cornflower (Centaurea cyanus), cetylpyridinium chloride, chamomile (Chamomillarecutita), quinoa (Chenopodium quinoa), and cinchona (Chinchona). Succirubra, Chondrus crispus, Citrus aurantium dulcis, Citrus grandis, Citrus limonum, Cocos nucifera, Coffea Arabica, Crataegus monogina, Cucumis melo, Dichlorophenylimidazoldioxolan, Enteromorpha compressa, Equisetum arvense, Ethoxydiethylene glycol, Ethyl panthenol, Farnesol, Ferulic acid, Fragaria chiloensis, Gentiana alutea, Ginkgo biloba, Glycerin, Glyceryl laurate, Glycyrrhiza glabra, Hamamelis virginiana, Heliotrope extract (heliotropine), hydrogenated palm oil glycerides, citrate, hydrolyzed castor oil, hydrolyzed wheat protein, Hypericum perforatum, Iris florentina, Juniper berries, milk protein, lactose, Lawsonia inermis, linalool, Linumus itatisimum, lysine, magnesium aspartate, mango, Malvasia sylvestris, mannitol, Melaleuca alternifolia, Menthapiperita, menthol, menthyl lactate, Mimosa tenuiflora, Nymphaea alba, olaflur, rice (Oryza sativa) Sativa, Panthenol, Liquid Paraffin, PEG-20M, PEG-26 Hojojoba Acid, PEG-26 Hojojoba Alcohol, PEG-35 Castor Oil, PEG-40 Hydrogenated Castor Oil, PEG-60 Hydrogenated Castor Oil, PEG-8 Caprylic / Capric Acid, Avocado (Perseagratissima), Petrolatum, Potassium Aspartate, Potassium Sorbate, Propylene Glycol, Sweet Almond (Prunus amygdalusdulcis), Apricot (Prunus armeniaca), Peach (Prunus persica), Retinyl Palmitate, Castor Bean (Ricinus communis), Dog Rose (Rosa canina), Rosemary (Rosmarinus officinalis), Raspberry (Rubusidaeus), Salicylic Acid, Elderberry (Sambucus nigra), Creatine, Saw Palmetto (Serenoaserrulata), Jojoba (Simmondsia) (chinensis), sodium carboxymethyl beta-glucan, sodium cocoyl amino acid, sodium hyaluronate, sodium palmitoyl praline, stearoxytrimethylsilane, stearyl alcohol, sulfonated TEA-ricinoleate, talc, thymus (Thymus vulgaris), Tilia cordata, tocopherol, tocopherol acetate, tridecyl alcohol polyether-9, wheat (triticum vulgare), tyrosine, undecenoyl glycine, urea, European blueberry (Vaccinium myrtillus), valine, zinc oxide, zinc sulfate.

[0148] Those skilled in the art will understand that the end-use formulation may contain at least one antimicrobial compound according to the invention and other ingredients classified as antimicrobial compounds but different from them, such as skin care ingredients. In this regard, the end-use formulation may contain at least one antimicrobial compound (e.g., levulinic acid) and ascorbic acid (as a skin care ingredient).

[0149] The antimicrobial compositions of the present invention can be used in emulsions (oil-in-water and water-in-oil), aqueous solutions, PIT (phase inversion temperature) emulsions, oily solutions, foaming cosmetic formulations (foams), and so-called multiple emulsions, such as triple emulsions (e.g., water / oil / water emulsions).

[0150] The antimicrobial compositions of the present invention can also be formulated as creams, gels, liquids, or lotions. They can be used in hair care products, such as shampoos, conditioners, hair masks, hair styling products, hair dyes, hair growth oils, hair gels, hair styling products, hair trimming aids, and other hair care preparations; shaving products, such as shaving creams, aftershaves, and other shaving products; personal cleansers for the body and hands, such as liquid bath soaps and detergents; fragrance preparations, such as perfumes, after-bath sprays, and other similar fragrance preparations; skin care products, such as moisturizers, creams, and lotions, and other similar skin care products; cosmetic products, such as makeup, mascara, foundation, etc.; makeup removers, sunscreens (e.g., sunscreen creams), tanning products, toothpaste, mouthwash, and other similar personal care products. In some embodiments, the antimicrobial compositions disclosed herein can be incorporated into formulations for impregnating wipes for personal hygiene and cleanliness (e.g., baby wipes, toilet wipes, makeup remover wipes, and exfoliating wipes, etc.). Antimicrobial compositions can also be used in other formulations in which antimicrobial compounds are required.

[0151] The above ingredients are also commonly used in home care products.

[0152] In some embodiments, the antimicrobial composition may be incorporated into household care products, such as cleaning products, including hand-dish soaps, machine-dish soaps, machine-dish rinse aids, laundry detergents, fabric conditioners, fabric fragrances and / or wrinkle treatments, ironing aids, cleaning wipes, general-purpose cleaners, and other similar formulations used in the home. In one embodiment, the household care product is selected from cleaning products such as hand-dish soaps, laundry detergents, cleaning wipes, and cleaning agents such as floor cleaners, countertop cleaners, kitchen cleaners, carpet cleaners, toilet cleaners, and bathroom cleaners.

[0153] In some embodiments, the antimicrobial composition may be included in the wipe formulation for impregnating the wipes. In these embodiments, the antimicrobial composition may be used to preservative the wipe formulation and the wipes before use. Once the wipe formulation composition is formulated, it is applied to a substrate.

[0154] The wipe formulation containing the antimicrobial composition can be applied to the substrate to be treated using conventional application techniques. Conventional techniques may include spraying, pouring, spraying, and / or wiping onto the substrate. In some embodiments, the wipe composition is provided to the end user as a ready-to-use formulation or in the form of a container with an application device. For example, the wipe formulation may be provided as an aerosol pressurized container, a container with a trigger or pump sprayer, a spray container, or a conventional container with a removable cap that allows the user to pour the formulation onto the substrate.

[0155] However, in some embodiments, the wipe formulation containing the antimicrobial composition disclosed herein can be impregnated or applied to a wipe substrate. In this embodiment, the wipe is a single-use wipe impregnated with the formulation and stored in a container to be dispensed to a user. The container containing the wipe can contain a single wipe or multiple wipes. Suitable containers include pouches containing single wipes, such as user-torn wipe packs, or pouches with resealable openings, in which multiple wipes are accommodated in a stacked or other suitable manner, such that one wipe can be removed from the opening at a time. Pouches are typically made of a fluid-resistant material, such as a film, coated paper, or foil, or other similar fluid-resistant material. In some embodiments, the wipes can be placed in a fluid-resistant container having an opening for removing the wipes from the container. In this way, a user can remove one or more wipes from the opening of the container. Suitable containers can include molded plastic containers with lids, which are typically fluid-resistant. The lids may have openings for removing the wipes from the container. The wet wipes in the container can be arranged in a staggered stack, such that when one wipe is removed from the container, the next wipe is positioned at the container's opening for the user to retrieve as needed. Alternatively, in some embodiments, the wipes can be a continuous material with perforations between the wipes. The perforated continuous wet wipe material can be in folded or rolled form. Typically, in rolled form, the wet wipe material is fed from the center of the roll and dispensed through the container's lid opening. Similar to staggered stacking, when one wipe is removed from the container, the next wipe is positioned at the opening for the user to retrieve as needed.

[0156] Disposable wipes offer advantages over other application media (such as reusable sponges, cloths, etc.). A particularly advantageous aspect is that soaked wipes are discarded after a single use, unlike reusable sponges, cloths, etc.

[0157] In some embodiments, the formulation containing the antimicrobial composition disclosed herein is impregnated into a wet wipe, such that the wet wipe is pre-wetted, and when the wet wipe is applied to a substrate to be treated, the formulation is squeezed out of the wet wipe or released onto the substrate. Typically, the formulation is saturated into the wet wipe, such that the wet wipe releases the formulation onto the substrate through a wiping action.

[0158] Suitable wet wipe substrates include woven and nonwoven materials. In some embodiments, any nonwoven fiber web material can be used. Exemplary nonwoven materials may include, but are not limited to, meltblown, coform, spunbond, airlaid, airlaced, hydroentangled nonwoven materials, spunlace, bonded carded webs, and laminates thereof. The fibers used to prepare the wet wipe substrate can be cellulose fibers, thermoplastic fibers, and mixtures thereof. The fibers can also be continuous fibers, discontinuous fibers, short fibers, and mixtures thereof. The basis weights of the nonwoven fiber web can vary from about 12 g / m² to 200 g / m² or greater.

[0159] In one embodiment, the substrate impregnated with the wiping composition contains a large amount of cellulose fibers. In particular, the wiping composition of the present invention is especially suitable for protecting cellulose substrates from microorganisms that may contaminate products. In a specific embodiment, for example, the substrate may be made of more than 80% by weight, for example, more than 85% by weight, for example, more than 90% by weight, for example, more than 95% by weight, for example, even 100% by weight of cellulose fibers. For example, in one embodiment, the substrate is made from pulp fibers and a binder via an air jet entanglement process. The basis weight of the substrate can be from about 20 gsm to about 100 gsm, for example, from about 40 gsm to about 70 gsm, for example, from about 50 gsm to about 60 gsm.

[0160] Once incorporated into the substrate, the resulting wiping product can have a liquid-to-substrate weight ratio of about 5:1 to about 1:1, for example about 2:1 to about 4:1.

[0161] As described above, in a fourth aspect, the present invention relates to a method for inhibiting the growth of microorganisms in home care, personal care products, or aqueous raw materials for inclusion in home or personal care formulations, comprising the step of adding the antimicrobial composition of the present invention to said home care or personal care product or aqueous raw material.

[0162] For example, embodiments of the corresponding antimicrobial compositions and home care or personal care products have been described above and are also applicable to this method. Further embodiments are described below.

[0163] According to the present invention, various microorganisms can be controlled / inhibited. For example, the antimicrobial composition of the present invention can control Gram-positive bacteria, Gram-negative bacteria, etc. In addition to bacteria, the antimicrobial composition of the present invention can also kill and control the growth of various other microorganisms, such as fungi, viruses, spores, yeasts, mycobacteria, etc.Non-limiting examples of specific microorganisms that can be controlled according to the present invention include Staphylococcus aureus, Streptococcus pneumoniae, Pseudomonas aeruginosa, Serratia marcescens, Salmonella enteritidis, Neisseria gonorrhoeae, Escherichia coli, Enterococcus hirae, Acinetobacter baumannii, Listeria monocytogenes, Enterobacter gergoviae, Klebsiella pneumoniae, Burholderia cepacia, Pseudomonas putida, and Kocuria... rhizophila, Candida albicans, Saccharomyces cerevisiae, Aspergillus brasiliensis, Penicillium funiculosum, Eupenicillium levitum, Bacillus cereus, Bacillus subtilis, Clostridium difficile, Clostridium perfringens, Mycobacterium tuberculosis, Mycobacterium terrae, Mycobacterium avium, poliovirus, adenovirus, norovirus, vaccinia virus, influenza virus, hepatitis B virus, human immunodeficiency virus. Immunodeficiency virus, human papillomavirus, or a mixture thereof.

[0164] In a fifth aspect, the present invention also relates to a method for preventing household care or personal care products from being spoiled by microorganisms, the method comprising incorporating an antimicrobial composition according to the present invention into the household care or personal care product.

[0165] In a sixth aspect, the invention also relates to the use of the antimicrobial composition according to the invention for improving efficacy against microorganisms compared with an equal amount of at least one antimicrobial compound that does not contain the said alkylene glycol ester.

[0166] In a seventh aspect, the present invention also relates to a method for enhancing the efficacy of an antimicrobial compound against microorganisms in an end-use formulation, the method comprising providing an end-use formulation and at least one antimicrobial compound, adding an effective amount of an alkylene glycol ester to the at least one antimicrobial compound and the end-use formulation to enhance the efficacy of the at least one antimicrobial compound in the end-use formulation compared to an equivalent amount of the antimicrobial compound in which the alkylene glycol ester is not present, wherein the at least one antimicrobial agent is selected from citric acid and its salts, salicylic acid and its salts, gluconolactone, levulinic acid and its salts, ethyl levulinate, butyl levulinate, ethylhexylglycerin, ethylene glycol, 1,3-propanediol, 1,3-butanediol, 2,3-butanediol, 1,2-pentanediol, 1,2-hexanediol, octanediol, ethyl lactate, butyl lactate, clomiphene, 1,2-decanediol, and 4-hydroxybenzene. Ethyl ketone, caprylhydroxamicacid and its salts, caprylic acid glyceride, chlorphenesin, triclosan, methylheptylglycerol, polyglycerol-2, 3, 4, 6, or 10-caprylate, polyglycerol-2, 3, 4, 6, or 10-decanoate / caprylate, azelaic acid, nonanoic acid, vitamin C, zinc oxide, zinc citrate, zinc pyrrolidone carboxylate (PCA zinc), zinc glycine, zinc oxide, nicotinamide, hyaluronic acid, 2- Methyl 5-cyclohexylpentanol, aluminum sulfate, aluminum zirconium, aluminum chloride, hydrated aluminum chloride, other aluminum salts, benzoyl peroxide, glycolic acid, phenylethanol, 3-phenylprop-1-ol, anisic acid and its salts, 1,2-heptanediol, octylglycerol ether, octyl glycine, tetrasodium diacetate of glutamic acid, trisodium dicarboxymethylalanine, and phytic acid and its salts, wherein the alkylene glycol esters are derived from (a) alkylene glycols and (b) fatty acids having about 6 to 14 carbon atoms.

[0167] For example, embodiments relating to the corresponding antimicrobial compositions, end-use formulations such as home care or personal care products, and microorganisms have been described above, and should also apply to aspects five through seven. Further embodiments are described below.

[0168] In one implementation, the improved efficacy is confirmed by a synergistic index value of less than 1.

[0169] It will be apparent to those skilled in the art that the above embodiments merely depict examples of a variety of possibilities. Therefore, the embodiments shown herein should not be construed as limiting these features and configurations. Any possible combination and configuration of the described features may be selected according to the scope of the invention. All embodiments and preferred embodiments described herein relating to a particular aspect of the invention (e.g., the antimicrobial compositions of the invention) are equally applicable to all other aspects of the invention, such as end-use formulations, uses, or methods according to the invention.

[0170] The following examples illustrate the invention but are not intended to limit it. Unless otherwise stated, all parts and percentages provided are by weight.

[0171] Example

[0172] method

[0173] To demonstrate the synergistic effect in the following examples, the propylene glycol octanoate (PGC) used was a mixture of mono- and di-propanediol octanoate (2-hydroxy-1-methylethyl octanoate and 2-hydroxypropyl octanoate) and di- and di-propanediol octanoate (1,2-propanediol dioctanoate), the mixture comprising about 70-80% by weight of mono- and di- and di-propanediol octanoate and about 20-30% by weight of di- and di-propanediol octanoate.

[0174] Test program

[0175] The synergistic activity of alkylene glycol esters and antimicrobial compounds was validated as part of a two-component composition.

[0176] A wide range of concentrations were tested against the following microorganisms: Pseudomonas aeruginosa ( Pseudomonas aeruginosa ATCC 9027 / DSM 1128), Staphylococcus aureus ( Staphylococcus aureus ATCC6538 / DSM 799), Escherichia coli ( Escherichia coli ATCC 8739 / DSM 1576) and Candida albicans ( Candida albicans ATCC 10231 / DSM 1386).

[0177] The lowest concentration of each mixture or single compound that prevents observable growth levels is determined as the minimum inhibitory concentration (MIC). The MIC value is determined for each microorganism.

[0178] Prepare a series of dilutions for each mixture or single compound. Inoculate the microorganisms into the culture medium: nutrient broth (bacteria) or malt extract broth (yeast). The final concentration of microorganisms in the culture medium is approximately 10. 5 CFU / ml. The inoculated culture medium was introduced into each serial dilution at a 1:1 ratio and incubated at 30±1℃ for 24-48 hours.

[0179] The MIC of each mixture was compared with the MIC of each individual compound.

[0180] The Kull equation was used to determine the synergistic effect (FC Kull et al., “Mixtures of Quaternary Ammonium Compounds and Long-chain Fatty Acids as Antifungal Agents”). Appl Microbiol . 1961 Nov; 9(6): 538–541), which calculates the Synergy Index (SI) based on the following equation:

[0181] SI = Qa / QA + Qb / QB

[0182] in

[0183] QA = the concentration of compound A, in ppm, that produces the endpoint when acting alone.

[0184] Qa = the concentration of compound A in the mixture that produces the endpoint, expressed in ppm (e.g., MIC).

[0185] QB = the concentration of compound B, in ppm, that produces the endpoint when acting alone.

[0186] Qb = the concentration of compound B in the mixture that produces the endpoint, expressed in ppm.

[0187] In this study, the endpoint was measured using the MIC. Where appropriate, the MIC was rounded to the nearest integer.

[0188] An SI value less than 1 indicates a synergistic effect. An SI value equal to 1 indicates an additive effect. An SI value greater than 1 indicates an antagonistic effect.

[0189] Synergy Index:

[0190] Synergistic interactions between propylene glycol octanoate (PGC) and antimicrobial compounds.

[0191]

[0192]

[0193] Pseudomonas aeruginosa:

[0194] The MIC (minimum inhibitory concentration) of PGC was not determined, therefore it was assumed that its MIC was higher than the highest concentration tested. In this study, the MIC of PGC was determined to be higher than 50,000 ppm, so 50,000 ppm was used as the MIC.

[0195]

[0196]

[0197]

[0198]

[0199]

[0200] The following study used PEG 40 HCl to dissolve hydroxyacetophenone. For this assay, the MIC of PGC was determined independently.

[0201]

[0202]

[0203]

[0204] Staphylococcus aureus:

[0205] The MIC of PGC was determined independently for each measurement.

[0206]

[0207]

[0208]

[0209]

[0210]

[0211]

[0212]

[0213]

[0214]

[0215] The following study used PEG 40 HCl to dissolve 4-hydroxyacetophenone. For this assay, the MIC of PGC was determined independently.

[0216]

[0217]

[0218]

[0219] Escherichia coli:

[0220] The MIC of PGC was not measured, therefore it was assumed to be higher than the highest concentration tested. In this study, the MIC of PGC was determined to be higher than 50,000 ppm, so 50,000 ppm was used as the MIC.

[0221]

[0222]

[0223]

[0224]

[0225]

[0226]

[0227]

[0228]

[0229]

[0230]

[0231]

[0232]

[0233]

[0234]

[0235]

[0236]

[0237] Candida albicans:

[0238] The MIC of PGC was determined independently for each measurement.

[0239]

[0240]

[0241]

[0242]

[0243]

[0244]

[0245]

[0246]

[0247]

[0248]

[0249]

[0250]

[0251]

[0252]

[0253]

[0254]

[0255]

[0256]

[0257]

[0258] The following study used PEG 40 HCl to dissolve 4-hydroxyacetophenone. For this assay, the MIC of PGC was determined independently.

[0259]

[0260]

[0261]

[0262]

[0263]

Claims

1. An antimicrobial composition comprising an alkylene glycol ester and at least one antimicrobial compound selected from citric acid and its salts, salicylic acid and its salts, gluconolactone, levulinic acid and its salts, ethyl levulinate, butyl levulinate, ethylhexylglycerin, ethylene glycol, 1,3-propanediol, 1,3-butanediol, 2,3-butanediol, 1,2-pentanediol, 1,2-hexanediol, octanediol, ethyl lactate, butyl lactate, clomiphene citrate, 1,2-decanediol, 4-hydroxyacetophenone, octyl isohydroxamic acid and its salts, octyl glycerol, chlorphenesin, triclosan, methylheptylglycerin, polyglycerol-2, 3, 4, 6, or 10-octyl ester, polyglycerol -2, 3, 4, 6, or 10-decanoate / caprylate, azelaic acid, vitamin C, zinc oxide, zinc citrate, zinc pyrrolidone carboxylate (PCA zinc), zinc glycinate, zinc oxide, nicotinamide, hyaluronic acid, 2-methyl-5-cyclohexylpentanol, aluminum sulfate, aluminum zirconium, aluminum chloride, hydrated aluminum chloride, other aluminum salts, benzoyl peroxide, glycolic acid, phenethyl alcohol, 3-phenylprop-1-ol, anisic acid and its salts, 1,2-heptanediol, octylglycerol ether, octyl glycine, tetrasodium diacetate of glutamate, trisodium dicarboxymethylalanine, and phytic acid and its salts, wherein the alkylene glycol esters and the antimicrobial compounds are present in a weight ratio of about 1:1000 to about 2500:

1.

2. An antimicrobial composition comprising an alkylene glycol ester and at least one antimicrobial compound selected from citric acid and its salts, salicylic acid and its salts, gluconolactone, levulinic acid and its salts, ethyl levulinate, butyl levulinate, ethylhexylglycerin, ethylene glycol, 1,3-propanediol, 1,3-butanediol, 2,3-butanediol, 1,2-pentanediol, 1,2-hexanediol, octanediol, ethyl lactate, butyl lactate, clomiphene, 1,2-decanediol, 4-hydroxyacetophenone, octyl isohydroxamic acid and its salts, octyl glycerol, chlorphenesin, triclosan, methylheptylglycerin, polyglycerol-2, 3, 4, 6, or 10- Caprylate, polyglycerol-2, 3, 4, 6, or 10-decanoate / caprylate, azelaic acid, vitamin C, zinc oxide, zinc citrate, zinc pyrrolidone carboxylate (PCA zinc), zinc glycinate, zinc oxide, nicotinamide, hyaluronic acid, 2-methyl-5-cyclohexylpentanol, aluminum sulfate, aluminum zirconium, aluminum chloride, hydrated aluminum chloride, other aluminum salts, benzoyl peroxide, glycolic acid, phenethyl alcohol, 3-phenylprop-1-ol, anisic acid and its salts, 1,2-heptanediol, octylglycerol ether, octyl glycine, tetrasodium diacetate of glutamate, trisodium dicarboxymethylalanine, and phytic acid and its salts, wherein the alkylene glycol esters and the antimicrobial compounds are present in synergistically effective amounts.

3. The antimicrobial composition according to claim 1 or 2, wherein the alkylene glycol ester comprises a propylene glycol ester, preferably propylene glycol octanoate, particularly propylene glycol monooctanoate.

4. The antimicrobial composition according to any one of claims 1 to 3, wherein the alkylene glycol ester is selected from alkylene glycol monoesters, alkylene glycol diesters and mixtures thereof, preferably from propylene glycol monoesters, propylene glycol diesters and mixtures thereof, more preferably from propylene glycol monooctanoate, propylene glycol dioctanoate and mixtures thereof, particularly a mixture of propylene glycol monooctanoate and propylene glycol dioctanoate or propylene glycol monooctanoate.

5. The antimicrobial composition according to any one of claims 1 to 4, wherein the alkylene glycol ester is a mixture of propylene glycol monooctanoate and propylene glycol dioctanoate, and the mixture comprises at least 10 wt.-%, preferably at least 30 wt.-%, particularly at least 60 wt.-% of propylene glycol monooctanoate based on the total weight of propylene glycol monooctanoate and propylene glycol dioctanoate.

6. The antimicrobial composition according to any one of claims 1 to 5, wherein the alkylene glycol ester and the antimicrobial compound are present in a weight ratio of about 1:1000 to about 2000:1, or about 1:1000 to about 1500:1, or about 1:1000 to about 500:1, or about 1:1000 to about 50:1, or about 1:800 to about 200:1, or about 1:800 to about 40:1, or about 1:600 ​​to about 1:150, or about 1:600 ​​to about 30:1, or about 1:550 to about 100:1, or about 1:550 to about 20:

1.

7. The antimicrobial composition according to any one of claims 1 to 6, wherein the at least one antimicrobial compound is selected from citric acid and its salts, salicylic acid and its salts, gluconolactone, levulinic acid and its salts, ethyl levulinate, butyl levulinate, ethylhexylglycerol, ethylene glycol, 1,3-propanediol, 1,3-butanediol, 2,3-butanediol, 1,2-pentanediol, 1,2-hexanediol, octanediol, ethyl lactate, methylheptylglycerol, zinc glycinate, and butyl lactate, preferably levulinic acid.

8. The antimicrobial composition according to claim 1 or 2, wherein the alkylene glycol ester is propylene glycol octanoate (PGC), and the antimicrobial compound is citric acid, and wherein the PGC and the citric acid are present in a weight ratio of about 1:32 to about 200:

1.

9. The antimicrobial composition according to claim 1 or 2, wherein the alkylene glycol ester is propylene glycol octanoate (PGC), and the antimicrobial compound is sodium salicylate, and wherein the PGC and the sodium salicylate are present in a weight ratio of about 1:128 to about 20:

1.

10. The antimicrobial composition according to claim 1 or 2, wherein the alkylene glycol ester is propylene glycol octanoate (PGC), and the antimicrobial compound is gluconolactone, and wherein the PGC and the gluconolactone are present in a weight ratio of about 1:128 to about 80:

1.

11. The antimicrobial composition of claim 1 or 2, wherein the alkylene glycol ester is propylene glycol octanoate (PGC), and the antimicrobial compound is levulinic acid, ethyl levulinic acid, or butyl levulinic acid, and wherein the PGC and the levulinic acid, ethyl levulinic acid, or butyl levulinic acid are present in a weight ratio of about 1:256 to about 5:1, preferably wherein the antimicrobial compound is levulinic acid, and wherein the PGC and the levulinic acid are present in a weight ratio of about 1:256 to about 5:1, or wherein the antimicrobial compound is ethyl levulinic acid or butyl levulinic acid, and wherein the PGC and the ethyl levulinic acid or butyl levulinic acid are present in a weight ratio of about 1:256 to about 1:

1.

12. The antimicrobial composition according to claim 1 or 2, wherein the alkylene glycol ester is propylene glycol octanoate (PGC), and the antimicrobial compound is ethylhexylglycerol, and wherein the PGC and the ethylhexylglycerol are present in a weight ratio of about 1:32 to about 4:

1.

13. The antimicrobial composition according to claim 1 or 2, wherein the alkylene glycol ester is propylene glycol octanoate (PGC), and the antimicrobial compound is octanediol, 1,2-pentanediol, or 1,2-hexanediol, and wherein the PGC and the octanediol, 1,2-pentanediol, or 1,2-hexanediol are present in a weight ratio of about 1:256 to about 5:1, preferably wherein the antimicrobial compound is octanediol, and wherein the PGC and the octanediol are present in a weight ratio of about 1:8 to about 5:1, or wherein the antimicrobial compound is 1,2-pentanediol, and wherein the PGC and the 1,2-pentanediol are present in a weight ratio of about 1:256 to about 2:13, or wherein the antimicrobial compound is 1,2-hexanediol, and wherein the PGC and the 1,2-hexanediol are present in a weight ratio of about 1:128 to about 4:13, and / or wherein the alkylene glycol ester is propylene glycol octanoate (PGC). C), wherein the antimicrobial compound is ethylene glycol, 1,3-propanediol, 1,3-butanediol, or 2,3-butanediol, and wherein the PGC and the ethylene glycol, 1,3-propanediol, 1,3-butanediol, or 2,3-butanediol are present in a weight ratio of about 1:256 to about 10:1, preferably wherein the antimicrobial compound is ethylene glycol, and wherein the PGC and the ethylene glycol are present in a weight ratio of about 1:256 to about 10:1, or wherein the antimicrobial compound is 1,3-propanediol, and wherein the PGC and the 1,3-propanediol are present in a weight ratio of about 1:128 to about 5:1, or wherein the antimicrobial compound is 1,3-butanediol, and wherein the PGC and the 1,3-butanediol are present in a weight ratio of about 1:128, or wherein the antimicrobial compound is 2,3-butanediol, and wherein the PGC and the 2,3-butanediol are present in a weight ratio of about 1:

128.

14. The antimicrobial composition according to claim 1 or 2, wherein the alkylene glycol ester is propylene glycol octanoate (PGC), and the antimicrobial compound is ethyl lactate or butyl lactate, and wherein the PGC and the ethyl lactate or butyl lactate are present in a weight ratio of about 1:512 to about 1:1, preferably wherein the antimicrobial compound is ethyl lactate, and wherein the PGC and the ethyl lactate are present in a weight ratio of about 1:512 to about 1:1, or wherein the antimicrobial compound is butyl lactate, and wherein the PGC and the butyl lactate are present in a weight ratio of about 1:128 to about 1:

1.

15. The antimicrobial composition according to claim 1 or 2, wherein the alkylene glycol ester is propylene glycol octanoate (PGC), and the antimicrobial compound is nonanoic acid, and wherein the PGC and the nonanoic acid are present in a weight ratio of about 1.1 to 8:

1.

16. The antimicrobial composition according to claim 1 or 2, wherein the alkylene glycol ester is propylene glycol octanoate (PGC), and the antimicrobial compound is 4-hydroxyacetophenone, and wherein the PGC and the 4-hydroxyacetophenone are present in a weight ratio of about 8:1 to 1:

8.

17. An end-use formulation, preferably a home care or personal care product, comprising an antimicrobial composition according to any one of claims 1 to 16.

18. The home care or personal care product of claim 17, wherein the antimicrobial composition comprises 0.02% to 10% by weight based on the total weight of the home care or personal care product, and / or wherein the antimicrobial composition is the antimicrobial composition of claim 11, preferably wherein the antimicrobial compound is levulinic acid.

19. The personal care product according to claim 17 or 18, selected from shampoos, body lotions, shower gels, deodorants, bubble baths, bath oils, creams, baby products, liquid soaps, hair gels, conditioners, hair conditioning masks, hair styling products, cosmetics, sunscreens, makeup products, toothpaste, mouthwash, and wipes.

20. The household care product according to claim 17 or 18, wherein it is a cleaning product, preferably selected from hand-washing dish soap, machine-washing dish soap, machine-washing dish rinse aid, laundry detergent, fabric conditioner, fabric fragrance and / or anti-wrinkle agent, ironing aid, cleaning wipes and general cleaning agents.

21. A method for inhibiting the growth of microorganisms in a household care product, a personal care product, or an aqueous ingredient for inclusion in a household care product or a personal care product, the method comprising the step of adding an antimicrobial composition according to any one of claims 1 to 16 to said household care product, personal care product, or aqueous ingredient.

22. A method for preventing microbial spoilage of an end-use formulation, preferably a home care or personal care product, comprising adding an antimicrobial composition according to any one of claims 1 to 16 to the end-use formulation, preferably the home care or personal care product.

23. Use of the antimicrobial composition according to any one of claims 1 to 16 for improving efficacy against microorganisms compared with an equal amount of at least one antimicrobial compound excluding the alkylene glycol ester, preferably wherein the improved efficacy is determined by a synergistic index value of less than 1.

24. A method for enhancing the efficacy of an antimicrobial compound against microorganisms in an end-use formulation, the method comprising providing an end-use formulation and at least one antimicrobial compound, adding an effective amount of an alkylene glycol ester to the at least one antimicrobial compound and the end-use formulation to enhance the efficacy of the at least one antimicrobial compound in the end-use formulation compared to an equivalent amount of the antimicrobial compound in which the alkylene glycol ester is not present, wherein the at least one antimicrobial agent is selected from citric acid and its salts, salicylic acid and its salts, gluconolactone, levulinic acid and its salts, ethyl levulinate, butyl levulinate, ethylhexylglycerin, ethylene glycol, 1,3-propanediol, 1,3-butanediol, 1,2-pentanediol, 1,2-hexanediol, octanediol, ethyl lactate, butyl lactate, clomiphene, 1,2-decanediol, 4- Hydroxyacetophenone, octyl isohydroxamic acid and its salts, octyl glycerol ester, chlorphenesin, triclosan, methyl heptaglycerol, polyglycerol-2, 3, 4, 6, or 10-octyl ester, polyglycerol-2, 3, 4, 6, or 10-decanoate / octyl ester, azelaic acid, nonanoic acid, vitamin C, zinc oxide, zinc citrate, zinc pyrrolidone carboxylate (PCA zinc), zinc glycinate, zinc oxide, nicotinamide, hyaluronic acid, 2-methyl-5-cyclohexylpentanol, aluminum sulfate, aluminum zirconium, aluminum chloride, hydrated aluminum chloride, other aluminum salts, benzoyl peroxide, glycolic acid, phenethyl alcohol, 3-phenylprop-1-ol, anisic acid and its salts, 1,2-heptanediol, octyl glycerol ether, octyl glycine, tetrasodium glutamate diacetate, trisodium dicarboxymethyl alanine, and phytic acid and its salts, wherein the alkylene glycol esters are derived from (a) alkylene glycols and (b) fatty acids having about 6 to 14 carbon atoms.

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