Antimicrobial composition containing cationic antimicrobial substances and acidic glycolipids

Abstract

This disclosure relates to antimicrobial compositions comprising at least one cationic antimicrobial substance and at least one acidic glycolipid, as well as the use of such compositions in product formulations, particularly anionic formulations such as personal care, home care, and other product formulations.

Description

[Technical Field]

[0001] The present invention relates to an antimicrobial composition containing a cationic antimicrobial substance and an acidic glycolipid, and to the use of this composition in product formulations such as personal care, home care, and other product formulations, particularly anionic formulations. [Background technology]

[0002] Many cationic substances, such as ethyl lauroyl alginate hydrochloride (LAE), chlorhexidine digluconate hydrochloride, and others, are known to be effective as antimicrobial and preservative agents. However, many product formulations are based on anionic formulations, such as those utilizing anionic rheology modifiers, anionic surfactants, and / or other anionic substances. Cationic antimicrobial agents such as LAE are generally unsuitable for use in these anionic formulations, and the combination can typically lead to aggregation and / or turbidity, and a decrease in antimicrobial activity. Therefore, cationic antimicrobial substances are generally unsuitable for use in anionic formulations. For example, while LAE is recommended as a broad-acting food safety preservative and is used in many personal care, food, and other product formulations, it is known to be incompatible with anionic thickeners such as carbomer, carboxymethylcellulose, carrageenan, and xanthan gum, as well as anionic surfactants such as sodium laureth sulfate or sodium lauryl sulfate (SLES / SLS) and alkyl phosphates, and carboxylates. In particular, its use in anionic formulations is usually avoided because the effectiveness of cationic antimicrobial agents such as LAE is generally lost.

[0003] Therefore, in personal care, home care, and other industries, there is a need to adapt cationic antimicrobial substances for use in anionic product formulations and achieve effective antimicrobial activity within those formulations. [Prior art documents] [Patent Documents]

[0004] [Patent Document 1] WO2021183526 [Overview of the project] [Problems that the invention aims to solve]

[0005] This need is addressed by this disclosure. As described herein, the use of cationic antimicrobial agents in combination with acidic glycolipids has been shown to enable their use as effective antimicrobial and preservative agents in anionic formulations. Furthermore, combining these cationic antimicrobial agents with the glycolipids enables an efficient antimicrobial alternative in anionic product formulations in personal care (e.g., cosmetics), home care, and other industries, and can impart effective antimicrobial activity to product formulations at lower usage levels than conventionally reported for cationic antimicrobial agents, regardless of whether they are anionic, nonionic, or cationic. [Means for solving the problem]

[0006] An antimicrobial composition is provided, comprising (a) a mixture of at least one cationic antimicrobial substance and (b) at least one acidic glycolipid, wherein the amount of at least one acidic glycolipid (b) by mass is approximately equal to or greater than the amount of at least one cationic antimicrobial substance (a) by mass.

[0007] The present invention also provides a method for preparing an antimicrobial composition comprising a combination of (a) at least one cationic antimicrobial substance and (b) at least one acidic glycolipid, wherein the amount of at least one acidic glycolipid (b) by mass is approximately equal to or greater than the amount of at least one cationic antimicrobial substance (a) by mass. Preferably, components (a) and (b) are combined in water and / or a water-miscible solvent. Preferably, components (a) and (b) are combined before use or addition to a product formulation, particularly anionic product formulations.

[0008] In another embodiment, product formulations are provided that include an effective amount of the antimicrobial composition of the present disclosure for applications such as personal care, home care, healthcare, food, or industrial products.

[0009] The product formulations of this disclosure are preferably anionic formulations, for example, an anionic product formulation comprising at least one anionic rheology modifier, at least one anionic surfactant, at least one anionic emulsifier, or a combination thereof, and an antimicrobially effective amount of at least one cationic antimicrobial substance or preservative and at least one acidic glycolipid, wherein the amount by mass of the at least one acidic glycolipid is approximately equal to or greater than the amount by mass of the at least one cationic antimicrobial substance or preservative.

[0010] Also provided is a method for formulating or preparing product formulations for applications such as personal care, home care, healthcare, food, or industrial products, comprising the step of adding an effective amount of (a) at least one cationic antimicrobial substance and (b) at least one acidic glycolipid to the product formulation, wherein the amount of at least one acidic glycolipid (b) by mass is approximately equal to or greater than the amount of at least one cationic antimicrobial substance (a) by mass. Components (a) and (b) may be added to the product formulation individually or in the form of a mixture, preferably in the form of a mixture such as the antimicrobial compositions described herein, particularly for addition to anionic product formulations.

[0011] In a further embodiment, a method is provided for controlling or inhibiting microbial growth, or for preserving product formulations such as formulations for personal care, home care, healthcare, food, or industrial products, comprising the step of adding an effective amount of (a) at least one cationic antimicrobial substance and (b) at least one acidic glycolipid to a product formulation, wherein the amount of at least one acidic glycolipid (b) by mass is approximately equal to or greater than the amount of at least one cationic antimicrobial substance (a) by mass. Components (a) and (b) may be added to the product formulation individually or in the form of a mixture, preferably in the form of a mixture such as the antimicrobial composition described herein, particularly for addition to anionic product formulations. Preferably, the product formulation is an anionic formulation. The method may further include the preparation of an antimicrobial composition by a combination of at least one cationic antimicrobial substance (a) and at least one acidic glycolipid (b), usually in water and / or a water-miscible solvent, before adding the antimicrobial composition to the product formulation, particularly an anionic formulation.

[0012] A method for preparing or formulating at least one cationic antimicrobial substance for an anionic product formulation is also provided, comprising the step of combining at least one cationic antimicrobial substance and an acidic glycolipid, usually in water and / or a water-miscible solvent, in such a way that the amount of at least one acidic glycolipid by mass is approximately equal to or greater than the amount of at least one cationic antimicrobial substance, before using or adding the cationic antimicrobial substance to the anionic product formulation. [Modes for carrying out the invention]

[0013] Unless otherwise specified, the following terms are defined as follows:

[0014] In this specification, “compound” means a preparation that is to retain or impart antimicrobial activity using the antimicrobial compositions of this disclosure.

[0015] In this specification, “cationic antimicrobial substance” means an antimicrobial compound having one or more cationic groups. A typical example in accordance with this disclosure is an antimicrobial compound having one or more cationic nitrogen-based groups.

[0016] In this specification, “anionic formulation” means a formulation that uses one or more anionic compounds. Examples of anionic compounds include, but are not limited to, anionic rheology modifiers and anionic surfactants, such as anionic thickeners and anionic emulsifiers.

[0017] In this specification, "glycolipid" means a compound comprising a carbohydrate group having one or more monosaccharide residues (e.g., monosaccharides, disaccharides, oligosaccharides, or polysaccharide residues) attached to a lipid group by a glycosidic bond.

[0018] In this specification, "glycosidic bond" or "glycosidic linkage" refers to a covalent bond that connects a monosaccharide or monosaccharide residue of a carbohydrate component to a lipid component.

[0019] In the antimicrobial compositions of this disclosure, “acidic glycolipid” means at least one glycolipid in an acidic form or a salt thereof (with respect to salts, for example, a physiologically, cosmetically, pharmacologically, or nutritionally acceptable salt), i.e., the lipid component of the glycolipid contains at least one carboxyl group in the form of a fatty acid moiety or a salt thereof, and the carbohydrate component is bound to the lipid component by a glycoside linkage without carboxyl groups. Generally, acidic glycolipids are usually miscible and / or soluble in water.

[0020] In this specification, "effective amount" refers to the amount that imparts the desired antibacterial effect or activity.

[0021] According to the present disclosure, it has surprisingly been discovered that by combining an acidic glycolipid with a cationic antimicrobial substance, the cationic antimicrobial substance can be used as an effective antibacterial agent and preservative in anionic formulations. Even more unexpectedly, the combination with the acidic glycolipid can reduce the level of use of the cationic antimicrobial substance to achieve effective antibacterial activity in any product formulation, whether anionic, nonionic, or cationic, compared to the levels previously reported.

[0022] The cationic antimicrobial substances of the present disclosure may be, for example, antimicrobial compounds having one or more cationic nitrogen-based groups. Examples of such compounds are known in the art. For example, the cationic antimicrobial substance is N α -alkanoyl dibasic amino acid alkyl ester salts such as N α -alkanoyl dibasic amino acid ester salts, preferably selected from. In many of those embodiments, the cationic antimicrobial substance is N α -(C6-C 20 ) alkanoyl dibasic amino acid (C1-C6) alkyl ester salts. N α -alkanoyl dibasic amino acid ester salts are preferably derived from dibasic amino acid esters such as L-arginine, L-histidine, L-tryptophan, or L-lysine, more preferably alkyl esters of L-arginine. The cationic antimicrobial substance may be derived from the condensation of a fatty acid such as a C6-C 20 fatty acid and a dibasic amino acid such as the esterified above-mentioned amino acid. Preferably, N α -alkanoyl dibasic amino acid ester salts are N α -lauroyl-L-arginine-(C1-C6) alkyl esters such as N α -(C6-C 20 ) alkanoyl-L-arginine-(C1-C6) alkyl esters, more particularly N α -lauroyl-L-arginine ethyl ester.

[0023] N α- The selection of the anionic component of the alkanoyl dibasic amino acid ester salt is not limited to a specific anion, and can be selected, for example, so that the solubility of the salt is sufficient for the intended mixing with acidic glycolipids and can also contribute to the intended use of the antimicrobial composition. Examples of such anions include, but are not limited to, halides, linolenates, laurates, oleoates, nitrates, nitrites, gluconates, and pyroglutamates.

[0024] N α - The alkanoyl dibasic amino acid ester salt is preferably of the following formula (I).

[0025] [ka]

[0026] In formula (I), R1 is a linear alkyl chain of a saturated fatty acid or hydroxy acid, bonded to an α-amino group via an amide bond, and having 6 to 20, preferably 8 to 14, carbon atoms. R2 is a linear or branched alkyl chain or aromatic group consisting of 1 to 6 carbon atoms, for example, 1 to 4 or 1 to 2 carbon atoms. R3 is selected from the following: [ka] n ranges from 1 to 6. X - Cl - , Br - Alternatively, it may be a counterion derived from an organic acid, an inorganic acid, or a phenolic compound.

[0027] Examples of acids that can be sources of counterion X include acetic acid, citric acid, lactic acid, fumaric acid, maleic acid, gluconic acid, propionic acid, sorbic acid, benzoic acid, carbonic acid, glutamic acid, pyroglutamic acid, lauric acid, oleic acid, linoleic acid, phosphoric acid, nitric acid, sulfuric acid, and thiocyanic acid. Examples of phenolic compounds that can be sources of counterion X include butylated hydroxyanisole (BHA), butylated hydroxytoluene, tertiary butylhydroquinone, methylparaben, ethylparaben, propylparaben, and butylparaben.

[0028] N α -The alkanoyl dibasic amino acid alkyl ester salt is more preferably of the following formula (II).

[0029] [ka]

[0030] In equation (II), R2, R3, n, and X are as in equation (I) above. m is 6 to 18, preferably 6 to 12.

[0031] N α A specific example of an alkanoyl dibasic amino acid ester salt is ethyl lauroyl alginate hydrochloride (LAE), which can be prepared from L-arginine and lauric acid, and in particular from the ethyl ester of the lauramide of arginine monohydrochloride. The chemical structure of LAE is shown in formula (III) below. [ka]

[0032] N α -Another example of an alkanoyl dibasic amino acid ester salt is N, such as CAE (pyrrolidone carboxylic acid (PCA) ethyl cocoyl alginate). αIt contains a cocoyl-L-arginine ethyl ester cation.

[0033] In preferred embodiments, the cationic antimicrobial substance has one or more cationic guanidine or amidine functional groups. As described above, LAE and CAE are examples of cationic antimicrobial substances having cationic guanidine groups. Further examples include, but are not limited to, alkyl guanidines and their salts, such as dodecyl guanidine and their salts (e.g., hydrochloride); biguanides and their salts, such as chlorhexidine, alexidine and their salts (e.g., digluconate, diacetate, dihydrochloride, cyclamate, etc.); and polybiguanides and their salts, such as polyhexamethylene biguanide (PHMB), polyaminopropyl biguanide and their salts (e.g., hydrochloride, acetate, gluconate, etc.). Hexamidine and their salts (e.g., diisethionate) are examples of cationic antimicrobial substances containing cationic amidine functional groups. Further examples of cationic antimicrobial substances having one or more guanidine or amidine functional groups, including further examples of the aforementioned subgenera, are known in the art.

[0034] Cationic antimicrobial substances may be quaternary ammonium compounds, including their salts. Examples include, but are not limited to, benzalkonium, cetrimonium, cetylpyridinium, alkyltrimethylammonium, dialkyldimethylammonium, polyquaternium, and their salts (e.g., chlorides, bromides, etc.). Further examples of quaternary ammonium antimicrobial substances and the aforementioned subgenus are known in the art.

[0035] Cationic antimicrobial substances can be further selected from peptides such as polylysine (e.g., epsilon-poly-L-lysine), nisin, and natamycin.

[0036] More than 1 cationic antimicrobial substance may be used in compositions, formulations, and methods of the present disclosure.

[0037] In many embodiments of the acidic glycolipids of this disclosure, the acidic glycolipid comprises a monosaccharide, disaccharide, or oligosaccharide moiety. In many embodiments, the acidic glycolipid comprises one, two, or three monosaccharide residues. One or more monosaccharide residues of the acidic glycolipid may be derived from, for example, glucose, sucrose, fructose, xylose, galactose, rhamnose, arabinose, mannose, cellobiose, lactose, galacturonate, sophorose, or mixtures thereof. One or more hydroxyl groups of the monosaccharide residue may be acylated (e.g., acetylated) or etherified. With respect to the lipid component, the fatty acid moiety may be saturated or unsaturated and may contain, for example, 6 to 30 carbon atoms (e.g., 8 to 28 or 10 to 26 carbon atoms), and they may be linear or branched. The fatty acid chain may be substituted with functional groups that are not particularly limited, insofar as the acidic glycolipid is generally miscible with water and / or soluble in water. Examples of substituents include halogen atoms, hydroxyls, alkyl groups (e.g., C 1~6 Alkyl), haloalkyl (e.g., halo C 1~6 Alkyl), hydroxyalkyl groups (e.g., hydroxy C 1~6 Alkyl), haloalkoxy group (e.g., halo C 1~6 This includes, but is not limited to, alkoxys and similar compounds. Furthermore, the lipid components may contain fatty acid residues that are esterified to each other.

[0038] The acidic glycolipids of this disclosure may have the following general formula.

[0039] [ka]

[0040] In formula (VII), L is a lipid group which may be linear or branched and which contains a saturated or unsaturated fatty acid moiety or a salt thereof which contains 6 to 30 carbon atoms (e.g., 8 to 28 or 10 to 26 carbon atoms) that are optionally substituted as described in the preceding paragraph, and R is a carbohydrate group which has 1 to 5 monosaccharide residues, preferably 1 to 3 (e.g., 1 or 2) monosaccharide residues, where each monosaccharide residue is independently a ring having a 5 or 6 membered ring, and one or more hydroxyl groups of the monosaccharide residues can be acylated (e.g., acetylated) or etherified.

[0041] The acidic glycolipids of this disclosure are produced by extraction or fermentation processes from natural resources (e.g., natural or modified microorganisms, fungi, etc.) that are known in the art, or by known chemical synthesis methods, or are available commercially.

[0042] In many embodiments, at least one acidic glycolipid of the present disclosure is a mixture of acidic glycolipids. In many embodiments, at least one acidic glycolipid is present in a mixture with at least one non-acidic glycolipid (e.g., at least one lactone glycolipid). When at least one acidic glycolipid is present in a mixture of acidic and non-acidic glycolipids, the acidic glycolipid typically accounts for 25% by mass, for example, at least 50% by mass, at least 60% by mass, at least 70% by mass, at least 80% by mass, or at least 90% by mass, based on the total mass of glycolipids in the mixture.

[0043] In many embodiments, the acidic glycolipid comprises at least one sophorolipid, at least one rhamnolipid, or a mixture thereof. The at least one acidic glycolipid preferably comprises one or more sophorolipids as described herein.

[0044] Sophorolipids generally consist of disaccharide sophoroses linked to fatty acids via glycosidic bonds. The fatty acid chain length generally varies as described herein for lipid components (e.g., 6 to 30, 8 to 28, or 10 to 26 carbon atoms) and can be saturated or unsaturated. Sophorolipids are generally known to exist in one of two common forms: acidic or lactone. The acidic glycolipids of this disclosure are preferably sophorolipids in acidic form (may include their salts). One or more acidic sophorolipids may exist in a mixture with one or more lactone sophorolipids as described above.

[0045] In many embodiments, the at least one acidic glycolipid comprises at least one sophorolipid of formula (IV) or a salt thereof. In further embodiments, the at least one sophorolipid of formula (IV) is present in a mixture with at least one lactone sophorolipid of formula (V).

[0046] [ka]

[0047] [ka]

[0048] In the above, R 1 and R 1‘ Each independently represents a saturated hydrocarbon chain, or one or more, particularly one, unsaturated hydrocarbon chain having 8 to 20 carbon atoms, for example 12 to 18 carbon atoms, particularly 14 to 18 or 14 to 16 carbon atoms, which may be linear or branched, and may contain halogen atoms, hydroxyl atoms, lower (C) atoms. 1~6 ) Alkyl group, lower halo (C 1~6 ) alkyl group, hydroxyl lower (C 1~6 ) Alkyl group, lower halo (C 1~6 ) May contain one or more substituents, including but not limited to alkoxy groups, R2 and R 2‘ Each independently represents a hydrogen atom, or a saturated alkyl functional group, or one or more, particularly one, unsaturated alkyl functional groups having 1 to 9 carbon atoms, for example, 1 to 4 carbon atoms, which may be linear or branched and may contain one or more hydroxyl groups. R 3 , R 3‘ , R 4 , and R 4’ Each of these independently represents either a hydrogen atom or an acetyl group.

[0049] In many embodiments, R 2 and R 2‘ This represents a methyl group or a hydrogen atom.

[0050] Sophorolipids may be produced or commercially available by fermentation processes from natural or modified microorganisms known in the art, such as yeast. Sophorolipid production processes are described, for example, in WO2021183526, and include production adjustment techniques, such as during fermentation, to promote the production of acidic forms of sophorolipids relative to lactone forms. Acidic forms of sophorolipids may be further isolated and purified by known techniques.

[0051] Acidic glycolipids may contain at least one rhamnolipid. Generally, a rhamnolipid consists of one or two rhamnose moieties (mono- or di-rhamnolipids) as a carbohydrate component attached to a fatty acid tail, which is usually a 3-(hydroxyalkanoyloxy)alkanoic acid (HAA), which varies in length and degree of branching, such as 3-hydroxydecanoic acid.

[0052] In many embodiments, at least one rhamnolipid is of formula (VI) or a salt thereof.

[0053] [ka]

[0054] In equation (VI), m is 2, 1, or 0, and n is 1 (diramnolipid) or 0 (monorhamnolipid), R 1 and R 2 These are the same or different organic functional groups, each independently having 2 to 24 carbon atoms, for example, 5 to 13 carbon atoms, preferably substituted (e.g., hydroxy-substituted), unsubstituted, branched, or unbranched alkyl functional groups, which may be unsaturated, and the alkyl functional group is preferably a linear saturated alkyl functional group having 8 to 12 carbon atoms, such as a nonyl or decyl functional group.

[0055] Rhamnolipid is known in the art, may be produced, or may be available commercially.

[0056] It should be understood that the acidic glycolipids of this disclosure may be provided in the form of salts, at least partially. For example, the cation of the glycolipid salt is Li + na + , K + Mg 2+ Ca 2+ , Al 3+ NH4 + Primary ammonium ions, secondary ammonium ions, tertiary ammonium ions, and quaternary ammonium ions may also be selected.

[0057] The acidic glycolipids of this disclosure may be used in crude form in production, or may be further processed by purification or isolation techniques, etc.

[0058] In the compositions, formulations, or methods of the present disclosure, the amount by mass of at least one acidic glycolipid is approximately equal to or greater than the amount by mass of at least one cationic antimicrobial substance. For example, the mass ratio of at least one acidic glycolipid to at least one cationic antimicrobial substance may be at least 1.1:1, at least 1.2:1, at least 1.4:1, at least 1.6:1, at least 1.8:1, at least 2:1, at least 2.5:1, at least 3:1, at least 3.5:1, at least 4:1, at least 4.5:1, or at least 5:1. Typically, the mass ratio of at least one acidic glycolipid to at least one cationic antimicrobial substance ranges from approximately 1:1 to 1.2:1, 1.4:1, 1.6:1, 1.8:1, 2:1, 2.5:1, 3:1, 3.5:1, 4:1, 4.5:1, or 5:1 to 100:1, 75:1, 50:1, 40:1, 35:1, 30:1, 25:1, 20:1, 15:1, or 10:1. In many embodiments, the mass ratio of at least one acidic glycolipid to at least one cationic antimicrobial substance ranges from about 1:1 to 1.2:1, 1.4:1, 1.6:1, 1.8:1, 2:1, 2.5:1, or 3:1 to 25:1, 20:1, 15:1, or 10:1. In many embodiments, the mass ratio of at least one acidic glycolipid to at least one cationic antimicrobial substance ranges from 1.2:1 to 20:1 or 15:1, for example, 1.4:1 to 15:1, 10.2:1, or 10:1. The above includes all ranges formed from any pair of lower and upper limits, including their endpoints.

[0059] The mass content of acidic glycolipids can be measured by methods known in this field, preferably by HPLC or HPLC / MS.

[0060] Cationic antimicrobial substances and acidic glycolipids are typically mixed in water and / or a water-miscible solvent to prepare antimicrobial compositions. Each component may, but is not required to, be present in the solvent or a suitable carrier at the time of mixing. Suitable water-miscible solvents include, for example, glycerin, glycerol, glycol, polyethylene glycol, and alcohol. This mixture containing the cationic antimicrobial substance and acidic glycolipid can be used or added to a variety of product formulations, as further described herein.

[0061] Generally, an antimicrobial composition may contain, for example, at least one cationic antimicrobial substance (a) and at least one acidic glycolipid (b) in a total amount, based on the mass of the antimicrobial composition, from about 3% by mass, from about 4% by mass, from about 5% by mass, preferably from about 10% by mass, from about 15% by mass, more preferably from about 20% by mass, or from about 30% by mass to about 99% by mass, up to about 95% by mass, preferably up to about 90% by mass, more preferably up to about 80% by mass, even more preferably up to about 70% by mass, up to about 60% by mass, or up to about 50% by mass. For example, the total amount of at least one cationic antimicrobial substance (a) and at least one acidic glycolipid (b) may be from about 5% by mass, or from about 10% by mass to about 95% by mass, preferably from about 10% by mass to about 90% by mass, more preferably from about 20% by mass to about 80% by mass, or from about 30% by mass to about 70% by mass. The composition may, for example, contain (c) one or more solvents in an amount from about 1% by mass, from about 3% by mass, from about 5% by mass, preferably from about 10% by mass, more preferably from about 20% by mass, or from about 30% by mass to about 97% by mass, up to about 95% by mass, up to about 90% by mass, up to about 80% by mass, preferably up to about 70% by mass, more preferably up to about 60% by mass, even more preferably up to about 50% by mass, or up to about 40% by mass, based on the mass of the antimicrobial composition. For example, the amount of component (c) may be from about 5% by mass to about 95% by mass, from about 10% by mass to about 90% by mass, from about 20% by mass to about 80% by mass, or from about 30% by mass to about 70% by mass, preferably from about 10% by mass, or from about 20% by mass to about 70% by mass, or up to about 60% by mass, more preferably from about 10% by mass, or from about 20% by mass to about 60% by mass, up to about 50% by mass, or up to about 40% by mass. The above includes all ranges formed by any pair of lower and upper limits, and their endpoints.

[0062] The antimicrobial composition may also contain, typically in small amounts, one or more excipients (d). Examples of excipients include, but are not limited to, dispersants, solubilizers, buffers, stabilizers, and / or preservatives. If present, these one or more excipients typically constitute, in total, from about 0.001% by mass to about 10% by mass, for example, from about 0.01% by mass, from about 0.05% by mass, or from about 0.1% by mass to about 5% by mass, up to about 3% by mass, or up to about 1% by mass, based on the mass of the antimicrobial composition. For example, component (d) may range from 0 to 10% by mass, from about 0.01% by mass to about 5% by mass, from about 0.1% by mass to about 5% by mass, from about 0.01% by mass to about 3% by mass, from about 0.1% by mass to about 3% by mass, from about 0.01% by mass to about 1% by mass, or from about 0.1% by about 1% by mass. The above includes all ranges formed by any pair of lower and upper limits, and their endpoints.

[0063] The antimicrobial composition may also contain one or more non-acidic glycolipids (e), such as lactone glycolipids, particularly lactone sophorolipids. Typically, the one or more non-acidic glycolipids are present in small amounts compared to the acidic glycolipids.

[0064] The compositional percentages and ratios are further related to the methods of this disclosure for preparing antimicrobial compositions, and it should be understood that the components may be combined, for example, according to the mass concentrations and ratios described herein.

[0065] In some embodiments, the antimicrobial composition substantially comprises at least one cationic antimicrobial substance (a), at least one acidic glycolipid (b), and at least one solvent (c), and optionally at least one excipient (d), and / or optionally at least one non-acidic glycolipid (e) (e.g., lactone sophorolipid).

[0066] In one embodiment, the antimicrobial compositions according to any embodiment of this specification do not contain bacteriophage endolysin.

[0067] This application provides the use of the antimicrobial compositions of this disclosure in product formulations, such as formulations for personal care, home care, healthcare, food, and industrial products. This application also encompasses the use of at least one cationic antimicrobial agent and at least one acidic glycolipid in product formulations, such as formulations used as personal care, home care, healthcare, food, or industrial products, where at least one cationic antimicrobial agent and at least one acidic glycolipid are added individually to the product formulation to provide the combination thereof of this disclosure. At least one cationic antimicrobial agent and at least one acidic glycolipid may be supplied to the product formulation in amounts and ratios by mass as described herein. Preferably, at least one or both of the at least one cationic antimicrobial agent and at least one acidic glycolipid are present in a solvent or in a suitable carrier, such as those described herein, for addition to the product formulation. Even if at least one cationic antimicrobial agent and at least one acidic glycolipid are added individually to a product formulation, it is believed that a product formulation containing one or more anionic materials (i.e., an anionic formulation as described herein), such as at least one of anionic rheology modifiers, anionic surfactants, or anionic emulsifiers, will benefit from the adaptation of cationic antimicrobial agents as described herein. However, without wishing to be bound by any particular theory, it is believed that the benefits associated with the combinations of the disclosures can be maximized by combining the cationic antimicrobial agent and the acidic glycolipid as described herein before applying the materials to an anionic product formulation. An anionic product formulation containing at least one cationic antimicrobial agent and at least one acidic glycolipid is free from or substantially free from aggregates or precipitates.

[0068] In many embodiments, the anionic product formulation includes, in addition to the antimicrobial composition, an anionic rheology modifier (e.g., an anionic thickener) and / or an anionic surfactant (e.g., an anionic emulsifier).

[0069] Examples of suitable anionic thickeners, though not limited to these, include carboxylic acid polymers, crosslinked polyacrylate polymers, polyacrylamide polymers, polysaccharides, and gums.

[0070] Non-restrictive examples of gum include acacia, agar, algin, alginic acid, ammonium alginate, amylopectin, calcium alginate, calcium carrageenan, carrageenan, dextrin, gelatin, gelan gum, karaya gum, konjac gum, locust bean gum, natto gum, potassium alginate, potassium carrageenan, propylene glycol alginate, sodium carboxymethyl dextran, sodium carrageenan, tragacanth gum, xanthan gum, and mixtures thereof.

[0071] Non-limiting examples of suitable polymeric anionic thickeners include acrylic acid homopolymers with INCI name carbomer, acrylic acid and alkyl acrylate copolymers with INCI name acrylate copolymer, acrylic acid and vinylpyrrolidone copolymers with INCI name acrylic acid / VP crosspolymer, acrylic acid and C10-C30 alkyl acrylate copolymers with INCI name acrylate / C10-C30 alkyl acrylate crosspolymer, acrylic acid and ethyl acrylate copolymers with INCI name acrylate copolymer, and Copolymers of (meth)acrylic acid and alkyl acrylates and ethoxylated hydrophobic modified alkyl acrylates include copolymers of associative alkyl acrylates, or copolymers of (meth)acrylic acid and alkyl acrylates and ethoxylated hydrophobic modified alkyl acrylates whose INCI names are acrylate / steareth-20 methacrylate copolymer, acrylate / steareth-20 methacrylate crosspolymer, acrylate / steareth-20 methacrylate copolymer, or acrylate / palmes-25 acrylate copolymer. Polymeric anionic thickeners also include, but are not limited to, acrylamide methylpropanesulfonic acid (AMPS)-based thickeners such as ammonium acryloyldimethyltaurate / VP copolymer or ammonium acryloyldimethyltaurate / beheneth-25 methacrylate copolymer.

[0072] The product formulation may contain, for example, at least one anionic thickener selected from polyacrylic acid-based polymers, xanthan gum, carbomer, carboxymethylcellulose, and carrageenan.

[0073] Examples of suitable anionic surfactants or emulsifiers, though not limited to these, include those having anionic functional groups such as sulfates, sulfonates, phosphates, and carboxylates on their heads.

[0074] Common examples of anionic surfactants, though not limited to these, include soaps, alkylbenzene sulfonates, alkanesulfonates, olefin sulfonates, alkyl ether sulfonates, glycerol ether sulfonates, methyl ester sulfonates, sulfo fatty acids, alkyl sulfates, fatty alcohol ether sulfates, glycerol ether sulfates, fatty acid ether sulfates, hydroxy mixed ether sulfates, monoglyceride (ether) sulfates, fatty acid amide (ether) sulfates, mono and dialkyl sulfosuccinates, mono and dialkyl sulfosuccinates, sulfotriglycerides, amide soaps, ether carboxylic acids and their salts, fatty acid isethionates, fatty acid sarcosinates, fatty acid taurides, N-acyl amino acids such as acyl lactylate, acyl tartrate, acyl glutarate, acyl aspartate, alkyl oligoglucoside sulfates, protein fatty acid condensates, and alkyl (ether) phosphates.

[0075] Examples of alkyl sulfates include ammonium lauryl sulfate, sodium lauryl sulfate (also known as sodium dodecyl sulfate, SDS), and related alkyl ether sulfates such as sodium lauryl ether sulfate (SLES) and sodium mireth sulfate. Carboxylates are common anionic surfactants and may include alkyl carboxylates such as sodium stearate.

[0076] In many embodiments, the product formulation contains an anionic surfactant or anionic emulsifier selected from sulfates (e.g., sodium laureth or lauryl sulfate (SLES / SLS)), sulfonates, phosphates, and carboxylates (e.g., alkyl sulfates, alkyl phosphates, or alkyl carboxylates).

[0077] The antimicrobial compositions of this disclosure may be used in nonionic and cationic formulations. Cationic antimicrobial substances and acidic glycolipids may be added to the product formulation individually, but preferably in the form of a mixture as described herein.

[0078] Generally, an effective amount of the antimicrobial composition is added to the product formulation. The optimized amount of the antimicrobial composition, and the specific optimized ratio of cationic antimicrobial substances and acidic glycolipids contained therein, may vary depending on, for example, the selected specific components, the end-use application, the desired level of antimicrobial activity or preservation, and the final characteristics of the product. As is well known in the art, antimicrobial effects can be demonstrated by a variety of suitable antimicrobial efficacy tests (AETs). Suitable test procedures and acceptance criteria are described, for example, in the United States Pharmacopeia, AETs, the European Pharmacopoeia (antimicrobial and preservative efficacy), and the Japanese Pharmacopoeia (preservative efficacy tests). Other suitable challenge tests, such as those recommended by the FDA, may be used.

[0079] Generally, an antimicrobial composition can be added to a product formulation, such as for personal care, home care, or other product applications, to provide a total amount of at least one cationic antimicrobial substance and at least one acidic glycolipid, for example, based on the mass of the formulation, ranging from about 0.01% by mass, from about 0.05% by mass, preferably from about 0.1% by mass, or more preferably from about 0.2% by mass to about 3% by mass, up to about 2.5% by mass, preferably up to about 2% by mass, more preferably up to about 1.5% by mass, or even more preferably up to about 1% by mass. Preferably, at least one cationic antimicrobial substance is added to the product formulation (and formulations containing at least one cationic antimicrobial substance) in an amount of 1% by mass or less or 0.75% by mass or less, more preferably 0.5% by mass or less, or even more preferably 0.25% by mass or less, 0.2% by mass or less, or 0.1% by mass or less. The above range includes all ranges formed from any pair of lower and upper limits, and their endpoints.

[0080] The antimicrobial compositions of this disclosure are suitable for use in a wide range of product formulations and applications, including applications in personal care, home care, healthcare (such as pharmaceuticals (i.e., those having at least one active pharmaceutical ingredient), vitamins, nutraceuticals, or other healthcare products), food, or industrial products. Examples include, but are not limited to, household goods and cleaners, laundry detergents, dish soaps, cleansers, soaps, bubble baths, disinfectants, deodorants, foods, food products, beverages, antimicrobial packaging, pharmaceuticals, medical devices, contact lenses, cosmetics, sanitary compositions, infant care products, antimicrobial soaps, hand sanitizers, deodorants, antiperspirants, antimicrobial coatings, dental compositions, toothpaste, mouthwash, lipstick, dental instruments, drugs, athlete's foot treatments, medicinal chewing gum, wound care compositions, skin compositions, acne treatments, skin conditioners, skin moisturizers, anti-wrinkle formulations, whitening agents, sunscreens, sunscreens, hair products, shampoos, shower gels, bubble baths, conditioners, shaving creams, spermicides, and the like. This also includes antibacterial fibers and clothing, antibacterial condoms, surgical gowns, antibacterial medical devices, antibacterial paper products, animal care products, antibacterial plastics, antibacterial plastic instruments, rubber and other processed materials, and instruments with antibacterial components or coatings.

[0081] Generally, product formulations include the antimicrobial composition of this disclosure and one or more additional components suitable for personal care (e.g., cosmetics), home care, healthcare, or industrial product formulations, or food product applications.

[0082] As a specific example, antimicrobial compositions may be incorporated into any number and variety of different personal care products, such as cosmetics. For example, the antimicrobial compositions of this disclosure may be used in personal care products used for skin care, hair care, oral care, makeup, personal cleaning, hygiene, sun protection, and other personal care applications. Examples of such products, but not limited to these, include skin toners, skin cleansers, night creams, skin creams, shaving creams, skin lotions, makeup, mascaras, lipsticks, blushes, glosses, eyeliners, makeup removers, sunscreens, lip balms, fragrances, massage oils, shampoos, conditioners, hair styling gels, hair repair agents, hair tonics, hair fixatives, hair mousses, bath and shower gels, liquid soaps, moisturizing sprays, bath additives, ophthalmic formulations, foaming soaps and body washes, and any liquid for personal care wet wipes.

[0083] As a further example, antimicrobial compositions can be incorporated into any number and variety of different home care products, such as fabric care products and cleaning products. Examples include dish soap, laundry detergent, cleaning wipes, cleaning formulations, and other home care products.

[0084] Depending on the application, product formulations may contain a large number of different suitable ingredients. Personal care formulations may contain, for example, any solvent, surfactant, emulsifier, chelating agent, oxidizing agent, colorant, rheological modifier, conditioner, emollient, skincare ingredient, moisturizer, thickener, moisturizing ingredient, filler, antioxidant, other antibacterial or preservative agents, active ingredients such as dermatologically active ingredients usually suitable for topical application, fragrances, etc.

[0085] Home care product formulations may contain, for example, any cleaning agents, detergents, emulsifiers, surfactants, thickeners, gelling agents, bleaches, whiteners, deodorants, enzymes, stabilizers, fragrances, stain repellents, shrinkage inhibitors, wrinkle inhibitors, stain inhibitors, antioxidants, UV-absorbing compounds, rust inhibitors, antistatic agents, ironing aids, odor-reducing compounds, etc.

[0086] Examples of the above-mentioned ingredients and other agents used in personal care and home care product compositions are known in the art.

[0087] Antimicrobial compositions may be included in a variety of different product formulations, such as liquids, pastes, serums, hydrogels, creams, emulsions, lotions, gels, oils, wipes, ointments, semi-solid compositions, foams, and aerosol sprays. Antimicrobial compositions may be used in leave-on or rinse-off product formulations. Antimicrobial compositions may be used in hair care products such as shampoos, hair conditioners, hair dyes, hair tonics, hair gels, hair dressings, hair grooming aids, and other hair care formulations; shaving products such as shaving creams, aftershave lotions, and other shaving products; personal cleaners for the body and hands such as liquid bath soaps and detergents; fragrance formulations such as perfumes, after-bath sprays, and other similar fragrance formulations; skin care products such as moisturizers, creams, lotions, and other similar skincare products; makeup products such as mascaras and base foundations; makeup removers; sunscreens; indoor tanning products; and other similar personal care products. Antimicrobial compositions may be incorporated into formulations used in saturated wipes used as personal cleaning and hygiene products, such as baby wipes, wet toilet wipes, makeup remover wipes, exfoliating wipes, or home care wet wipe formulations.

[0088] Preferably, when added to a product formulation, the antimicrobial composition provides an antimicrobial effect according to the challenge test procedure in the following examples, which achieves a passing growth rating based on the criteria related to Table 3 in this specification.

[0089] The antimicrobial compositions of this disclosure may be used in product formulations containing other antimicrobial substances, preservatives, or boosters. Examples of such agents include those for which the antimicrobial compositions of this disclosure are beneficial and suitable for use in a variety of industries. Examples of suitable additional antimicrobial substances or boosters, but not limited to these, include 1,2-decanediol, 1,2-hexanediol, 1,3-propanediol, 4-hydroxyacetophenone, amyl cinnamaldehyde, benzyl alcohol, caprylhydroxamic acid, caprylyl glycol, cinnam alcohol, cinnamaldehyde, ethylhexylglycerin, gluconolactone, glyceryl caprate / caprylate, phenethyl alcohol, phenoxyethanol, potassium benzoate, propylene glycol caprylate, p-thymol, salicylic acid, sodium anisate, sodium benzoate, sodium dehydroacetate, sodium levulinate, sorbic acid, sorbitan caprylate, and combinations thereof. At least one additional antimicrobial agent or booster may be present in an amount of 1% by mass or less, preferably 0.75% by mass or 0.5% by mass or less, more preferably less than 0.4% by mass or less than 0.3% by mass, for example, in an amount from about 0.05% by mass to less than 0.3% by mass (for example, from about 0.05% by mass to about 0.25% by mass).

[0090] Preferably, at least one additional antimicrobial agent or booster is selected from sodium benzoate, glyceryl caprylate, 4-hydroxyacetophenone, sodium dehydroacetate, sodium anisate, 1,2-hexanediol, gluconolactone, benzyl alcohol, and combinations thereof.

[0091] The disclosure further includes methods for controlling or inhibiting microbial growth or preserving product formulations, such as formulations for personal care, home care, healthcare, food, or industrial product applications. The methods include adding effective amounts of at least one cationic antimicrobial agent and at least one acidic glycolipid to a product formulation, wherein the mass amount of at least one acidic glycolipid is approximately equal to or greater than the mass amount of at least one cationic antimicrobial agent, as described herein by mass ratio.

[0092] Preferably, the product formulation is an anionic formulation. At least one cationic antimicrobial agent and at least one acidic glycolipid may be added to the product formulation, individually or in mixture form, preferably in mixture form, as described herein, for use in an antimicrobial composition, particularly for addition to an anionic product formulation. The method may further include a step of preparing an antimicrobial composition, by combining at least one cationic antimicrobial agent and at least one acidic glycolipid, usually in water and / or a water-miscible solvent, before adding at least one cationic antimicrobial agent and at least one acidic glycolipid to the product formulation, particularly to an anionic formulation.

[0093] A method for preparing an antimicrobial composition is also provided, comprising a combination of at least one cationic antimicrobial substance and at least one acidic glycolipid, wherein the amount by mass of at least one acidic glycolipid is approximately equal to or greater than the amount by mass of at least one cationic antimicrobial substance, as described in the mass ratios herein. Preferably, at least one cationic antimicrobial substance and at least one acidic glycolipid are combined in water and / or a water-miscible solvent. Preferably, at least one cationic antimicrobial substance and at least one acidic glycolipid are combined before use or addition to a product formulation, particularly an anionic product formulation.

[0094] Also provided is a method for formulating or preparing at least one cationic antimicrobial substance for use in an anionic product formulation, wherein the amount by mass of at least one acidic glycolipid is approximately equal to or greater than the amount by mass of at least one cationic antimicrobial substance, as described herein by mass ratio, and the method typically includes the step of combining the at least one cationic antimicrobial substance and the acidic glycolipid in water and / or a water-miscible solvent before use or addition of the cationic antimicrobial substance to an anionic product formulation.

[0095] Further, we provide a method for preparing or formulating product formulations for personal care, home care, healthcare, food or industrial product applications, comprising the step of adding an effective amount of at least one cationic antimicrobial agent and at least one acidic glycolipid to a product formulation, wherein the amount by mass of at least one acidic glycolipid is approximately equal to or greater than the amount by mass of at least one cationic antimicrobial agent, as described in the mass ratios described herein. The at least one cationic antimicrobial agent and at least one acidic glycolipid may be added to the product formulation individually or in mixture form, preferably in the form of a mixture such as the antimicrobial compositions described herein, particularly for addition to anionic product formulations.

[0096] This disclosure further includes, but is not limited to, the following exemplary embodiments.

[0097] Embodiment 1: comprising at least one of an anionic rheology modifier, anionic surfactant, or anionic emulsifier, and a combination of at least one cationic antimicrobial substance and at least one acidic glycolipid in an amount effective for antimicrobial activity, wherein the cationic antimicrobial substance is (1) A compound having one or more cationic guanidine or amidine functional groups, or (2)N α -Alkanoyl dibasic amino acid ester salts including, or, At least one acidic glycolipid contains at least one acidic sophorolipid, A product formulation in which the amount by mass of at least one acidic glycolipid is approximately equal to or greater than the amount by mass of at least one cationic antimicrobial substance.

[0098] Embodiment 2: The product formulation according to Embodiment 1, wherein the cationic antimicrobial substance comprises or is an alkylguanidine, a biguanide, a polybiguanide, a salt thereof, or a combination thereof.

[0099] Embodiment 3: The product formulation according to Embodiment 1, wherein the cationic antimicrobial substance comprises or is dodecylguanidine, chlorhexidine, alexidine, polyhexamethylene biguanide, polyaminopropyl biguanide, hexamidine, salts thereof, or combinations thereof.

[0100] Embodiment 4: The cationic antimicrobial substance is N α -(C6~C 20 The product formulation according to Embodiment 1, comprising or containing an alkanoyl dibasic amino acid (C1-C6) alkyl ester salt.

[0101] Embodiment 5: The cationic antimicrobial substance is N of the following formula (I). α - Contains or is an alkanoyl dibasic amino acid ester salt. [ka] In the above formula (I), R1 is a linear alkyl chain of a saturated fatty acid or hydroxy acid having 6 to 20 carbon atoms and bonded to an α-amino group via an amide bond. R2 is a linear or branched alkyl chain of 1 to 6 carbon atoms, or an aromatic group. R3 is selected from the following: [ka] n ranges from 1 to 6. X - Cl - , Br -Alternatively, a counterion derived from an organic or inorganic acid or a phenolic compound, Product formulation as described in Embodiment 1.

[0102] Embodiment 6: The cationic antimicrobial substance is N α -(C6~C 20 The product formulation according to Embodiment 1, comprising or being an alkanoyl-L-arginine (C1-C6) alkyl ester salt.

[0103] Embodiment 7: The product formulation according to Embodiment 1, wherein the cationic antimicrobial substance comprises or is ethyl lauroyl alginate hydrochloride (LAE), pyrrolidone carboxylic acid (PCA), ethyl cocoyl alginate, chlorhexidine digluconate, or a combination thereof.

[0104] Embodiment 8: At least one acidic sophorolipid is of the following formula (IV), [ka] In equation IV above, R 1‘ This is an optionally substituted saturated or unsaturated hydrocarbon chain having 8 to 20 carbon atoms, which may be linear or branched. R 2‘ This is a saturated or unsaturated alkyl functional group having a hydrogen atom or 1 to 9 carbon atoms, which may be linear or branched, and is optionally substituted with one or more hydroxyl groups. R 3‘ and R 4‘ These are, independently, a hydrogen atom or an acetyl group. A product formulation according to any one embodiment of Embodiments 1 to 7.

[0105] Embodiment 9: A product formulation according to any one embodiment of Embodiments 1 to 8, wherein the mass ratio of the acidic glycolipid to the cationic antimicrobial substance is about 1:1 to 100:1, preferably 1.2:1 to 20:1.

[0106] Embodiment 10: A product formulation according to any one embodiment of Embodiments 1 to 9, wherein the product formulation comprises at least one anionic rheology modifier, which includes a carboxylic acid polymer, a crosslinked polyacrylate polymer, a polyacrylamide polymer, a polysaccharide, a gum, or a combination thereof.

[0107] Embodiment 11: The product formulation according to Embodiment 10, wherein the anionic rheology modifier comprises a polyacrylic acid-based polymer, xanthan gum, carbomer, carboxymethylcellulose, carrageenan, or a combination thereof.

[0108] Embodiment 12: A product formulation according to any one embodiment of Embodiments 1 to 11, wherein the product formulation comprises at least one anionic surfactant, which includes sulfates, sulfonates, phosphates, carboxylates, or combinations thereof.

[0109] Embodiment 13: A product formulation according to any one embodiment of Embodiments 1 to 12, wherein the product formulation is a personal care or home care product formulation.

[0110] Embodiment 14: A product formulation according to any one embodiment of Embodiments 1 to 13, wherein at least one cationic antimicrobial substance is present in an amount not exceeding 0.5% by mass, preferably not exceeding 0.25% by mass, based on the mass of the formulation.

[0111] Embodiment 15: A product formulation according to any one embodiment of Embodiments 1 to 14, wherein the formulation further comprises at least one additional antimicrobial agent or booster agent selected from 1,2-decanediol, 1,2-hexanediol, 1,3-propanediol, 4-hydroxyacetophenone, amyl cinnamaldehyde, benzyl alcohol, caprylyl hydroxy acid, caprylyl glycol, cinnam alcohol, cinnamaldehyde, ethylhexylglycerin, gluconolactone, glyceryl caprate, glyceryl caprylate, phenethyl alcohol, phenoxyethanol, potassium benzoate, propylene glycol caprylate, p-thymol, salicylic acid, sodium anisate, sodium benzoate, sodium dehydroacetate, sodium levulinate, sorbic acid, sorbitan caprylate, and combinations thereof.

[0112] Embodiment 16: The product formulation according to Embodiment 15, wherein at least one additional antimicrobial agent or booster agent is present in an amount not exceeding 0.5% by mass, preferably less than 0.3% by mass, based on the mass of the formulation.

[0113] Embodiment 17: The product formulation according to Embodiment 15 or 16, wherein at least one additional antimicrobial agent or booster is selected from sodium benzoate, glyceryl caprylate, 4-hydroxyacetophenone, sodium dehydroacetate, sodium anisate, 1,2-hexanediol, gluconolactone, benzyl alcohol, and combinations thereof.

[0114] Embodiment 18: A method for preparing a product formulation according to any one embodiment of Embodiments 1 to 17, comprising the steps of: providing a formulation containing at least one anionic rheology modifier, anionic surfactant, or anionic emulsifier; and adding at least one acidic glycolipid and at least one cationic antimicrobial substance to the formulation in an amount that is effective in antimicrobial activity.

[0115] Embodiment 19: The method according to Embodiment 18, wherein at least one cationic antimicrobial substance and at least one acidic glycolipid are added to a formulation in the form of a mixture.

[0116] Embodiment 20: A method for controlling microbial growth in a product formulation, or a method for preserving a product formulation, comprising at least one of an anionic rheology modifier, an anionic surfactant, or an anionic emulsifier, The process includes adding at least one cationic antimicrobial substance and at least one acidic glycolipid to the product formulation in an amount that is effective in antimicrobial activity. (I) One or more cationic guanidines, or compounds having an amidine functional group, (II)N α -Alkanoyl dibasic amino acid ester salts, It contains or is a cationic antimicrobial substance. A method wherein at least one acidic glycolipid contains at least one acidic sophorolipid, and the amount by mass of at least one acidic glycolipid is approximately equal to or greater than the amount by mass of at least one cationic antimicrobial substance.

[0117] Embodiment 21: The method according to Embodiment 20, wherein at least one cationic antimicrobial substance and at least one acidic glycolipid are added to a product formulation in the form of a mixture.

[0118] Embodiment 22: The method according to Embodiment 20 or 21, wherein the cationic antimicrobial substance comprises or is an alkylguanidine, a biguanide, a polybiguanide, a salt thereof, or a combination thereof.

[0119] Embodiment 23: The method according to Embodiment 20 or 21, wherein the cationic antimicrobial substance comprises or is dodecylguanidine, chlorhexidine, alexidine, polyhexamethylene biguanide, polyaminopropyl biguanide, hexamidine, salts thereof, or combinations thereof.

[0120] Embodiment 24: A cationic antimicrobial substance is N α -(C6~C 20 The method according to Embodiment 20 or 21, comprising or being an alkanoyl dibasic amino acid (C1-C6) alkyl ester salt.

[0121] Embodiment 25: The cationic antimicrobial substance is N of the following formula (I). α - Contains or is an alkanoyl dibasic amino acid ester salt. [ka] In the above chemical formula I, R1 is a linear alkyl chain of a saturated fatty acid or hydroxy acid, having 6 to 20 carbon atoms, and is bonded to an α-amino group via an amide bond. R2 is a linear or branched alkyl chain of 1 to 6 carbon atoms, or an aromatic group. R3 is selected from the following: [ka] n ranges from 1 to 6. X - Cl - , Br - or counterions derived from organic or inorganic acids or phenolic compounds, The method according to Embodiment 20 or 21.

[0122] Embodiment 26: A cationic antimicrobial substance is N α -(C6~C 20 The method according to Embodiment 20 or 21, comprising or being an alkanoyl-L-arginine (C1-C6) alkyl ester salt.

[0123] Embodiment 27: The method according to Embodiment 20 or 21, wherein the cationic antimicrobial substance comprises or is ethyl lauroyl alginate hydrochloride (LAE), pyrrolidone carboxylic acid (PCA), ethyl cocoyl alginate, chlorhexidine digluconate, or a combination thereof.

[0124] Embodiment 28: At least one acidic sophorolipid is of the following formula (IV), [ka] In the above equation (IV), R 1‘ This is an optionally substituted saturated or unsaturated hydrocarbon chain having 8 to 20 carbon atoms, which may be linear or branched. R 2‘ This is a saturated or unsaturated alkyl functional group having a hydrogen atom or 1 to 9 carbon atoms, which may be linear or branched, and which is optionally substituted with one or more hydroxyl groups. R 3‘ and R4‘ These are, independently, a hydrogen atom or an acetyl group. A method according to any one embodiment of Embodiments 20 to 27.

[0125] Embodiment 29: The method according to any one embodiment of Embodiments 20 to 28, wherein at least one acidic sophorolipid is present in a mixture with at least one lactonic sophorolipid in an amount of at least 50% by mass, for example, at least 60% by mass, at least 70% by mass, at least 80% by mass, or at least 90% by mass, based on the total mass of sophorolipids in the mixture, and is in an acidic form.

[0126] Embodiment 30: The following formula (IV) represents at least one acidic sophorolipid, and the following formula (V) represents at least one lactone sophorolipid, [ka] [ka] In the above formulas (IV) and (V), R 1 R 1‘ Each of these is independently a saturated or unsaturated hydrocarbon chain having 8 to 20 carbon atoms, which may be linear or branched, and which may be optionally substituted. R 2and R 2‘ Each is independently a hydrogen atom or a saturated or unsaturated alkyl functional group having 1 to 9 carbon atoms, which may be linear or branched, and optionally substituted with one or more hydroxyl groups. R 3 , R 3‘ , R 4 and R 4‘ Each is independently a hydrogen atom or an acetyl group. The method according to Embodiment 29.

[0127] Embodiment 31: The method according to any one embodiment of Embodiments 20 to 30, wherein the mass ratio of the acidic glycolipid to the cationic antimicrobial substance is about 1:1 to 100:1, preferably 1.2:1 to 20:1.

[0128] Embodiment 32: The method according to any one embodiment of Embodiments 20 to 31, wherein the product formulation is a personal care or home care product formulation.

[0129] Embodiment 33: The method according to any one embodiment of Embodiments 20 to 32, wherein at least one cationic antimicrobial substance is added in an amount not exceeding 0.5% by mass, preferably not exceeding 0.25% by mass, based on the mass of the formulation.

[0130] Embodiment 34: The method according to any one embodiment of Embodiments 20 to 33, further comprising the step of adding to the formulation at least one additional antimicrobial substance or booster selected from 1,2-decanediol, 1,2-hexanediol, 1,3-propanediol, 4-hydroxyacetophenone, amyl cinnamaldehyde, benzyl alcohol, caprylhydroxamic acid, caprylyl glycol, cinnam alcohol, cinnamaldehyde, ethylhexylglycerin, gluconolactone, glyceryl caprylate, glyceryl caprate, phenethyl alcohol, phenoxyethanol, potassium benzoate, propylene glycol caprylate, p-thymol, salicylic acid, sodium anisate, sodium benzoate, sodium dehydroacetate, sodium levulinate, sorbic acid, sorbitan caprylate, and combinations thereof.

[0131] Embodiment 35: The method according to Embodiment 34, wherein at least one additional antimicrobial agent or booster is added in an amount not exceeding 0.5% by mass, preferably less than 0.3% by mass, based on the mass of the formulation.

[0132] Embodiment 36: The method according to Embodiment 34 or 35, wherein at least one additional antimicrobial agent or booster agent is selected from sodium benzoate, glyceryl caprylate, 4-hydroxyacetophenone, sodium dehydroacetate, sodium anisate, 1,2-hexanediol, gluconolactone, benzyl alcohol, and combinations thereof.

[0133] Embodiment 37: An antimicrobial composition comprising (a) at least one cationic antimicrobial substance and (b) a combination of at least one acidic glycolipid, in an amount of about 10% to about 95% by mass, preferably about 10% to about 90% by mass, more preferably about 20% to about 80% by mass, and even more preferably about 30% to about 70% by mass, based on the total mass of the antimicrobial composition, wherein the cationic antimicrobial substance is (I) One or more cationic guanidines, or compounds having an amidine functional group, (II)N α - Contains or comprises an alkanoyl dibasic amino acid ester salt, At least one acidic glycolipid comprises or is an acidic sophorolipid, The mass ratio of (b) to (a) is approximately 1:1 to 100:1. Antibacterial composition.

[0134] Embodiment 38: The antimicrobial composition according to Embodiment 37, wherein the cationic antimicrobial substance comprises or is an alkylguanidine, a biguanide, a polybiguanide, a salt thereof, or a combination thereof.

[0135] Embodiment 39: The antimicrobial composition according to Embodiment 37, wherein the cationic antimicrobial substance comprises or is dodecylguanidine, chlorhexidine, alexidine, polyhexamethylene biguanide, polyaminopropyl biguanide, hexamidine, salts thereof, or combinations thereof.

[0136] Embodiment 40: A cationic antimicrobial substance is N α -(C6-C 20 The antimicrobial composition according to Embodiment 37, comprising or containing an alkanoyl dibasic amino acid (C1-C6) alkyl ester salt.

[0137] Embodiment 41: The cationic antimicrobial substance is N of the following formula (I). α - Contains or is an alkanoyl dibasic amino acid ester salt. [ka] In the above formula (I), R1 is bonded to an α-amino group via an amide bond, has 6 to 20 carbon atoms, and is a linear alkyl chain of a saturated fatty acid or hydroxy acid. R2 is a linear or branched alkyl chain of 1 to 6 carbon atoms, or an aromatic group. R3 is selected from the following,

Chemical formula

[0138] Embodiment 42: The cationic antibacterial substance is N α -(C6 - C 20 ) alkanoyl-L-arginine (C1 - C6) alkyl ester salt, or is, the antibacterial composition according to Embodiment 37.

[0139] Embodiment 43: The cationic antibacterial substance contains ethyl lauroyl arginate hydrochloride (LAE), pyrrolidone carboxylic acid (PCA), ethyl cocoyl arginate, chlorhexidine digluconate, or a combination thereof, or is, the antibacterial composition according to Embodiment 37.

[0140] Embodiment 44: At least one acidic sophorolipid is the following formula (IV),

Chemical formula

[0141] Embodiment 45: An antimicrobial composition according to any one embodiment of Embodiments 37 to 44, wherein the mass ratio of the acidic glycolipid to the cationic antimicrobial substance is 1.2:1 to 20:1.

[0142] Embodiment 46: The antimicrobial composition according to any one embodiment of Embodiments 37 to 45, wherein the combined amount of (a) and (b) is about 20% by mass to about 80% by mass, based on the total mass of the antimicrobial composition.

[0143] As used herein, the articles “a,” “an,” and “the” placed before an element or component of an invention are not intended to be restrictive with respect to the number of instances (i.e., occurrences) of the element or component. Therefore, “a,” “an,” and “the” should be read as including one or at least one, and the singular form of the element or component also includes the plural form unless the number is clearly intended to be singular.

[0144] As used herein, the term “comprising” means the presence of features, integers, processes, or components as described in the claims, but does not exclude the presence or addition of one or more other features, integers, processes, components, or groups thereof. Unless otherwise specified in the context, “comprising” is intended to include embodiments that are encompassed by the terms “consisting essentially of” and “consisting of.”

[0145] As used herein, the term “about” modifying the amount of an ingredient used indicates the possible variation in numerical quantity due to, for example, the normal measurement and operating procedures used to prepare a concentrate or solution in the real world, careless errors in those procedures, differences in manufacturing, the source, or the purity of the ingredients used to prepare the composition, or the methods performed.

[0146] If any range exists, all ranges are inclusive and combinable. For example, if the range "1 to 5" is specified, the specified range should be interpreted as including ranges such as "1 to 4", "1 to 3", "1 to 2", "1 to 2 and 4 to 5", and "1 to 3 and 5".

[0147] Where a parameter is given as a range, a preferred range, or a list of preferred upper and preferred lower values, whether the range is disclosed separately or not, this should be understood as clearly disclosing all ranges formed from any pair of any upper limit or preferred value and any lower limit or preferred value. Wherever a numerical range is described herein, unless otherwise specified, that range is intended to include its endpoints and all integers and fractions within that range. [Examples]

[0148] Challenge Test Procedure The preservative activity of representative formulations was evaluated using an improved method of the Personal Care Products Council (PCPC) protocol (Machtiger et al., 2001, Evaluation of preservative effects of water-miscible cosmetic and toiletry formulations for non-eye areas, collaborative research, J of AOAC International. 84:1, 101-109). To determine the preservative effect of each treatment, a microbial preservative effect test (challenge test) was performed over 4 weeks, in 2 cycles, at 25°C.

[0149] Table 1 shows typical formulations of xanthan gum-based anionic lotion compositions. Xanthan gum is commonly used as a natural rheological modifier in personal care products. The formulations below were prepared by heating the aqueous phase (A) and oil phase (B) separately to 75 to 80°C. The oil phase was then poured into the aqueous phase and mixed using an overhead mixer and homogenizer. The oil-in-water emulsion was cooled to room temperature. Sodium hydroxide solution was used to adjust the pH.

[0150] [Table 1]

[0151] The lotion formulation sample was further added to the specific test material as described below, thoroughly mixed at room temperature, and divided into two 5-gram aliquots. One aliquot was inoculated with 50 μl of diluted bacterial pool, and the second aliquot was inoculated with 50 μl of diluted fungal pool as described below. Unpreserved product samples were included in the test as a growth control.

[0152] Mixed bacterial inoculum was prepared using test bacteria (Table 2) cultured for 24 hours in Tripticase Soy Medium (TSB). The bacterial test strains were combined in equal volumes, diluted 10-fold with phosphate buffer, and measured approximately 5 × 10⁶ units per ml. 7 From 5x10 8An inoculum of colony-forming units (cfu / ml) was obtained. The test samples were inoculated with a 1% mixed bacterial inoculum. The mixed fungal inoculum was prepared in phosphate buffer using cell suspensions of yeast Candida albicans ATCC#10231 and mold Aspergillus brasiliensis ATCC#16404. The fungal test strains were combined in equal volumes and diluted 10-fold with phosphate buffer to obtain an inoculum of approximately 5×10 6 to 5×10 7 cfu / ml. The test samples were inoculated with a 1% mixed fungal inoculum.

[0153]

Table 2

[0154] The samples were subjected to a microbial challenge at time zero and a second inoculation was performed after 7 days. The number of microorganisms added to each sample was determined by the standard most-probable number (MPN) method using trypticase soy broth (TSB) for bacteria and potato dextrose broth (PDB) for fungi. The samples were cultured at 25°C during a 4-week test period. The bacterial and fungal contamination of the samples was monitored on days 2, 7, 14, 21, and 28, respectively.

[0155] Samples challenged for bacteria were streak-plated on Trypticace soy agar (TSA) and incubated at 30°C for 24 hours. Samples challenged for fungi were streak-plated on potato dextrose agar (PDA) and incubated at 25°C for 7 days. After incubation, the plates were assigned a Growth Rating to determine the number of colony-forming units (CFU / g) present in each test sample at that time. Table 3 shows the growth scores. As used in various challenge test methods, the pass criteria for bacteria are stricter than for fungi. For bacteria, a rating of 2, 3, or 4 at day 21 and / or day 28 was considered a failure. For fungi, a rating of 2 at day 21 and / or day 28 was considered a pass.

[0156] [Table 3]

[0157] In the bacterial challenge test, a composition was judged as "passing" if it obtained a bacterial growth evaluation score of 1 or less between days 21 and 28 of the test period, and as "failing" if it obtained a bacterial growth evaluation score of 2 or more between days 21 and 28.

[0158] In the fungal challenge test, if a composition obtained a fungal growth evaluation score of 2 or less between days 21 and 28 of the test period, that composition was judged as "passing," and if a composition obtained a fungal growth evaluation score greater than 2 between days 21 and 28, it was judged as "failing."

[0159] A "pass" rating for the administered composition was conditional on the unpreserved sample receiving a "fail" rating.

[0160] Test materials and abbreviations CHD.G: Chlorhexidine digluconate GC: Glyceryl Caprylate GL-A: A sophorolipid mixture aqueous solution (in which the mass ratio of acidic sophorolipids and lactone sophorolipids of formulas (IV) and (V) herein is approximately 90:10) GL-L: Aqueous solution of sophorolipid mixture (in which the mass ratio of acidic sophorolipids and lactone sophorolipids of formulas (IV) and (V) herein is approximately 30:70) HAP: 4-Hydroxyacetophenone LAE: Ethyl lauroyl alginate hydrochloride NaBz: Sodium benzoate XG: Xanthan Gum Lotion

[0161] The ethyl lauroyl alginate hydrochloride (LAE) used to form the mixture with acidic glycolipids was a solid raw material with a purity exceeding 85%, and when added alone to the test formulation (as a control), it was a 20% by mass solution of LAE in glycerin.

[0162] The chlorhexidine digluconate used in this test was a 20% by mass aqueous solution.

[0163] Solutions containing LAE and glycolipids were prepared by dissolving high-purity solid LAE raw materials in GL-A or GL-L glycolipid mixtures. These mixtures were prepared using approximately 1% to 20% LAE in a glycolipid / water mixture. Solutions containing CHD.G and glycolipids were prepared using approximately 5% CHD.G in a GL-A / glycolipid mixture. The resulting solutions were administered as test samples to representative lotion formulations.

[0164] In particular, representative lotion formulations containing xanthan gum were prepared using the compositions listed in Table 1. According to the samples and mass percentages listed in Tables 4 and 5, this unpreserved anionic xanthan gum lotion was administered to various test samples at room temperature and thoroughly mixed. The concentrations of LAE and CHD.G in the sample formulations are shown in ppm. The mass percentage of acidic glycolipids in the sample formulations, and the mass ratio of acidic glycolipids to LAE or CHD.G, are shown in columns 3 and 4, respectively.

[0165] As shown, when LAE, CHD.G, GL-A, or GL-L solutions alone, or mixtures of LAE and GL-L with an acidic glycolipid mass ratio of approximately 0.5 to LAE, were administered, none of the lotion formulations passed the challenge test. However, when the anionic formulation was administered to a mixture of LAE or CHD.G and GL-A with an acidic glycolipid ratio to LAE or CHD.G as shown in Samples I to L and N, the mixture was conferred with effective antibacterial activity and met the pass criteria, as shown in Table 4.

[0166] [Table 4]

[0167] Unpreserved anionic xanthan gum lotions were further administered with various antimicrobial booster compounds according to the samples and mass percentages shown in Table 5. As shown, none of the lotion formulations passed the challenge test when administered with NaBz, GC, or HAP alone, or in combination with GL-A or LAE. However, when the anionic formulations were administered with LAE or a mixture of CHD.G and GL-A, as well as the booster compounds shown in Table 5, the formulations were conferred with effective antimicrobial activity and met the pass criteria.

[0168] [Table 5] Table 6

Claims

1. At least one of an anionic rheology modifier, anionic surfactant, or anionic emulsifier, and It comprises a combination of at least one cationic antimicrobial substance and at least one acidic glycolipid in an amount that is effective in antibacterial activity, The aforementioned cationic antimicrobial substance (1) A compound having one or more cationic guanidine or amidine functional groups, (2) N α - Alkanoyl dibasic amino acid ester salts Includes, The at least one acidic glycolipid comprises at least one acidic sophorolipid, A product formulation in which the amount by mass of the at least one acidic glycolipid is approximately equal to or greater than the amount by mass of the at least one cationic antimicrobial substance.

2. The product formulation according to claim 1, wherein the cationic antimicrobial substance comprises alkylguanidine, biguanide, polybiguanide, salts thereof, or combinations thereof.

3. The product formulation according to claim 1, wherein the cationic antimicrobial substance comprises dodecylguanidine, chlorhexidine, alexidine, polyhexamethylene biguanide, polyaminopropyl biguanide, hexamidine, salts thereof, or combinations thereof.

4. The aforementioned cationic antimicrobial substance is N α - (C ６ ~C ２０ ) Alkanoyl dibasic amino acid (C １ ~C ６ The product formulation according to claim 1, comprising an alkyl ester salt.

5. The cationic antimicrobial substance is N of the following formula (I). α - Contains alkanoyl dibasic amino acid ester salts, 【Chemistry 1】 In the above formula (I), R １ It is a linear alkyl chain of a saturated fatty acid or hydroxy acid, bonded to an α-amino group via an amide bond and having 6 to 20 carbon atoms. R ２ is a straight-chain or branched alkyl chain having 1 to 6 carbon atoms, or an aromatic group, R ３ The following can be selected: 【Chemistry 2】 n is between 1 and 6. X － Cl － , Br － Alternatively, a counterion derived from an organic or inorganic acid or a phenolic compound, The product formulation according to claim 1.

6. The aforementioned cationic antimicrobial substance is N α - (C ６ ~C ２０ ) Alkanoyl-L-arginine (C １ ~C ６ The product formulation according to claim 1, comprising an alkyl ester salt.

7. The product formulation according to claim 1, wherein the cationic antimicrobial substance comprises ethyl lauroyl alginate hydrochloride (LAE), pyrrolidone carboxylic acid (PCA), ethyl cocoyl alginate, chlorhexidine digluconate, or a combination thereof.

8. The at least one acidic sophorolipid is defined by the following formula (IV): 【Transformation 3】 In the above formula IV, R １‘ This is an optionally substituted saturated or unsaturated hydrocarbon chain having 8 to 20 carbon atoms, which may be linear or branched. R ２‘ This is a saturated or unsaturated alkyl functional group having a hydrogen atom or 1 to 9 carbon atoms, which may be linear or branched, and is optionally substituted with one or more hydroxyl groups. R ３‘ and R ４‘ These are, independently, a hydrogen atom or an acetyl group. Product formulation according to any one of claims 1 to 7.

9. The product formulation according to any one of claims 1 to 8, wherein the mass ratio of the acidic glycolipid to the cationic antimicrobial substance is about 1:1 to 100:

1.

10. The product formulation according to claim 9, wherein the mass ratio of the acidic glycolipid to the cationic antimicrobial substance is 1.2:1 to 20:

1.

11. The product formulation according to any one of claims 1 to 10, wherein the product formulation comprises at least one anionic rheology modifier, which includes a carboxylic acid polymer, a crosslinked polyacrylate polymer, a polyacrylamide polymer, a polysaccharide, a gum, or a combination thereof.

12. The product formulation according to claim 11, wherein the anionic rheology modifier comprises a polyacrylic acid-based polymer, xanthan gum, carbomer, carboxymethylcellulose, carrageenan, or a combination thereof.

13. The product formulation according to any one of claims 1 to 12, wherein the product formulation comprises at least one anionic surfactant, which includes sulfates, sulfonates, phosphates, carboxylates, or combinations thereof.

14. The product formulation according to any one of claims 1 to 13, wherein the product formulation is a personal care or home care product formulation.

15. The product formulation according to any one of claims 1 to 14, wherein the at least one cationic antimicrobial substance is present in an amount not exceeding 0.5% by mass, based on the mass of the formulation.

16. The product formulation according to claim 15, wherein the at least one cationic antimicrobial substance is present in an amount not exceeding 0.25% by mass, based on the mass of the formulation.

17. The product formulation according to any one of claims 1 to 16, wherein the formulation further comprises at least one additional antimicrobial agent or booster agent selected from 1,2-decanediol, 1,2-hexanediol, 1,3-propanediol, 4-hydroxyacetophenone, amyl cinnamaldehyde, benzyl alcohol, caprylyl hydroxy acid, caprylyl glycol, cinnam alcohol, cinnamaldehyde, ethylhexylglycerin, gluconolactone, glyceryl caprate, glyceryl caprylate, phenethyl alcohol, phenoxyethanol, potassium benzoate, propylene glycol caprylate, p-thymol, salicylic acid, sodium anisate, sodium benzoate, sodium dehydroacetate, sodium levulinate, sorbic acid, sorbitan caprylate, and combinations thereof.

18. The product formulation according to claim 17, wherein the at least one additional antimicrobial substance or booster agent is present in an amount not exceeding 0.5% by mass, based on the mass of the formulation.

19. The product formulation according to claim 18, wherein the at least one additional antimicrobial substance or booster agent is present in an amount of less than 0.3% by mass, based on the mass of the formulation.

20. The product formulation according to any one of claims 17 to 19, wherein the at least one additional antimicrobial agent or booster agent is selected from sodium benzoate, glyceryl caprylate, 4-hydroxyacetophenone, sodium dehydroacetate, sodium anisate, 1,2-hexanediol, gluconolactone, benzyl alcohol, and combinations thereof.

21. A method for preparing a product formulation according to any one of claims 1 to 20, comprising the steps of: providing a formulation comprising at least one anionic rheology modifier, an anionic surfactant, or an anionic emulsifier; and adding to the formulation an amount that is effective in antimicrobial activity the at least one acidic glycolipid and the at least one cationic antimicrobial substance.

22. The method according to claim 21, wherein the at least one cationic antimicrobial substance and the at least one acidic glycolipid are added to the formulation in the form of a mixture.

23. A method for controlling microbial growth in a product formulation, or a method for preserving the product formulation, comprising at least one of an anionic rheology modifier, an anionic surfactant, or an anionic emulsifier, The process includes adding at least one cationic antimicrobial substance and at least one acidic glycolipid to the product formulation in an amount that is effective in antimicrobial activity. (I) One or more cationic guanidines, or compounds having an amidine functional group, (II) N α - Alkanoyl dibasic amino acid ester salts, The cationic antimicrobial substance contains the above, The at least one acidic glycolipid comprises at least one acidic sophorolipid, A method wherein the amount by mass of the at least one acidic glycolipid is approximately equal to or greater than the amount by mass of the at least one cationic antimicrobial substance.

24. The method according to claim 23, wherein the at least one cationic antimicrobial substance and the at least one acidic glycolipid are added to the product formulation in the form of a mixture.

25. The method according to claim 23 or 24, wherein the cationic antimicrobial substance comprises alkylguanidine, biguanide, polybiguanide, salts thereof, or combinations thereof.

26. The method according to claim 23 or 24, wherein the cationic antimicrobial substance comprises dodecylguanidine, chlorhexidine, alexidine, polyhexamethylene biguanide, polyaminopropyl biguanide, hexamidine, salts thereof, or combinations thereof.

27. The aforementioned cationic antimicrobial substance is N α - (C ６ ~C ２０ ) Alkanoyl dibasic amino acid (C １ ~C ６ The method according to claim 23 or 24, comprising an alkyl ester salt.

28. The aforementioned cationic antimicrobial substance is N of the following formula I. α - Contains alkanoyl dibasic amino acid ester salts, 【Chemistry 4】 In the above chemical formula I, R １ It is a linear alkyl chain of saturated fatty acids or hydroxy acids, bonded to an α-amino group via an amide bond, and having 6 to 20 carbon atoms. R ２ This is a linear or branched alkyl chain of 1 to 6 carbon atoms, or an aromatic group. R ３ The following can be selected: 【Transformation 5】 n is between 1 and 6. X － Cl － , Br － or counterions derived from organic or inorganic acids or phenolic compounds, The method according to claim 23 or 24.

29. The aforementioned cationic antimicrobial substance is N α - (C ６ ~C ２０ ) Alkanoyl-L-arginine (C １ ~C ６ The method according to claim 23 or 24, comprising an alkyl ester salt.

30. The method according to claim 23 or 24, wherein the cationic antimicrobial substance comprises ethyl lauroyl alginate hydrochloride (LAE), pyrrolidone carboxylic acid (PCA), ethyl cocoyl alginate, chlorhexidine digluconate, or a combination thereof.

31. The at least one acidic sophorolipid is defined by the following formula (IV): 【Transformation 6】 In the above formula (IV), R １‘ This is an optionally substituted saturated or unsaturated hydrocarbon chain having 8 to 20 carbon atoms, which may be linear or branched. R ２‘ This is a saturated or unsaturated alkyl functional group having a hydrogen atom or 1 to 9 carbon atoms, which may be linear or branched, and which is optionally substituted with one or more hydroxyl groups. R ３‘ and R ４‘ These are, independently, a hydrogen atom or an acetyl group. The method according to any one of claims 23 to 30.

32. The method according to any one of claims 23 to 31, wherein the at least one acidic sophorolipid is present in an amount of at least 50% by mass, based on the total mass of sophorolipids in the mixture, as a mixture with at least one lactonic sophorolipid, and is in an acidic form.

33. The following formula (IV) represents the at least one acidic sophorolipid, and the following formula (V) represents the at least one lactone sophorolipid. 【Transformation 7】 【Transformation 8】 In the above formulas (IV) and (V), R １ And R １‘ Each of these is independently a saturated or unsaturated hydrocarbon chain having 8 to 20 carbon atoms, which may be linear or branched, and which may be optionally substituted. R ２ and R ２‘ Each is independently a hydrogen atom or a saturated or unsaturated alkyl functional group having 1 to 9 carbon atoms, which may be linear or branched, and is optionally substituted with one or more hydroxyl groups. R ３ , R ３‘ , R ４ and R ４‘ Each is independently a hydrogen atom or an acetyl group. The method according to claim 32.

34. The method according to any one of claims 23 to 33, wherein the mass ratio of the acidic glycolipid to the cationic antimicrobial substance is about 1:1 to 100:

1.

35. The method according to claim 34, wherein the mass ratio of the acidic glycolipid to the cationic antimicrobial substance is 1.2:1 to 20:

1.

36. The method according to any one of claims 23 to 35, wherein the product formulation is a personal care or home care product formulation.

37. The method according to any one of claims 23 to 36, wherein the at least one cationic antimicrobial substance is added in an amount not exceeding 0.5% by mass, based on the mass of the formulation.

38. The method according to claim 37, wherein the at least one cationic antimicrobial substance is added in an amount not exceeding 0.25% by mass, based on the mass of the formulation.

39. The method according to any one of claims 23 to 38, further comprising the step of adding to the formulation at least one additional antimicrobial substance or booster selected from 1,2-decanediol, 1,2-hexanediol, 1,3-propanediol, 4-hydroxyacetophenone, amyl cinnamaldehyde, benzyl alcohol, caprylhydroxamic acid, caprylyl glycol, cinnam alcohol, cinnamaldehyde, ethylhexylglycerin, gluconolactone, glyceryl caprylate, glyceryl caprylate, phenethyl alcohol, phenoxyethanol, potassium benzoate, propylene glycol caprylate, p-thymol, salicylic acid, sodium anisate, sodium benzoate, sodium dehydroacetate, sodium levulinate, sorbic acid, sorbitan caprylate, and combinations thereof.

40. The method according to claim 39, wherein the at least one additional antimicrobial substance or booster agent is added in an amount not exceeding 0.5% by mass, based on the mass of the formulation.

41. The method according to claim 40, wherein the at least one additional antimicrobial substance or booster agent is added in an amount of less than 0.3% by mass, based on the mass of the formulation.

42. The method according to any one of claims 39 to 41, wherein the at least one additional antimicrobial agent or booster agent is selected from sodium benzoate, glyceryl caprylate, 4-hydroxyacetophenone, sodium dehydroacetate, sodium anisate, 1,2-hexanediol, gluconolactone, benzyl alcohol, and combinations thereof.

43. An antimicrobial composition comprising (a) a combination of at least one cationic antimicrobial substance and (b) at least one acidic glycolipid, in an amount of about 10% to about 95% by mass based on the total mass of the antimicrobial composition, wherein the cationic antimicrobial substance is (I) One or more cationic guanidines, or compounds having an amidine functional group, (II) N α - Contains alkanoyl dibasic amino acid ester salts, The aforementioned at least one acidic glycolipid comprises at least one acidic sophorolipid, The mass ratio of (b) to (a) is approximately 1:1 to 100:

1. Antibacterial composition.

44. The antimicrobial composition according to claim 43, wherein the cationic antimicrobial substance comprises alkylguanidine, biguanide, polybiguanide, salts thereof, or combinations thereof.

45. The antimicrobial composition according to claim 43, wherein the cationic antimicrobial substance comprises dodecylguanidine, chlorhexidine, alexidine, polyhexamethylene biguanide, polyaminopropyl biguanide, hexamidine, salts thereof, or combinations thereof.

46. The aforementioned cationic antimicrobial substance is N α - (C ６ -C ２０ ) Alkanoyl dibasic amino acid (C １ ~C ６ The antimicrobial composition according to claim 43, comprising an alkyl ester salt.

47. The cationic antimicrobial substance is N of the following formula (I). α - Contains alkanoyl dibasic amino acid ester salts, 【Chemistry 9】 In the above formula (I), R １ It is bonded to an α-amino group via an amide bond, has 6 to 20 carbon atoms, and is a linear alkyl chain of a saturated fatty acid or hydroxy acid. R ２ This is a linear or branched alkyl chain of 1 to 6 carbon atoms, or an aromatic group. R ３ The following can be selected: 【Chemistry 10】 n is between 1 and 6. X － Cl － , Br － or counterions derived from organic or inorganic acids or phenolic compounds, The antimicrobial composition according to claim 43.

48. The aforementioned cationic antimicrobial substance is N α - (C ６ ~C ２０ ) Alkanoyl-L-arginine (C １ -C ６ The antimicrobial composition according to claim 43, comprising an alkyl ester salt.

49. The antimicrobial composition according to claim 43, wherein the cationic antimicrobial substance comprises ethyl lauroyl alginate hydrochloride (LAE), pyrrolidone carboxylic acid (PCA), ethyl cocoyl alginate, chlorhexidine digluconate, or a combination thereof.

50. The at least one acidic sophorolipid is defined by the following formula (IV): 【Chemistry 11】 In the above formula (IV), R １‘ This is an optionally substituted saturated or unsaturated hydrocarbon chain having 8 to 20 carbon atoms, which may be linear or branched. R ２‘ This is a saturated or unsaturated alkyl functional group having a hydrogen atom or 1 to 9 carbon atoms, which may be linear or branched, and which is optionally substituted with one or more hydroxyl groups. R ３‘ and R ４‘ These are, independently, a hydrogen atom or an acetyl group. The antimicrobial composition according to any one of claims 43 to 49.

51. The antimicrobial composition according to any one of claims 43 to 50, wherein the mass ratio of the acidic glycolipid to the cationic antimicrobial substance is 1.2:1 to 20:

1.

52. The antibacterial composition according to any one of claims 43 to 51, wherein the combined amount of (a) and (b) is about 20% by mass to about 80% by mass, based on the total mass of the antibacterial composition.

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