Alkylhydroxamic acid potassium hydrogen salts and compositions containing the same

Abstract

The present invention relates to potassium hydrogen alkyl hydroxamate compounds and compositions, as well as formulations containing same, methods for preparing the potassium hydrogen alkyl hydroxamate compounds of the invention, and uses thereof, including the use of the compounds and compositions of the invention in products or in the formulation of components of products.

Description

Technical Field

[0001] [Cross - Reference to Related Applications] This application claims priority to U.S. Provisional Patent Application No. 63 / 235,495, filed on August 20, 2021, which is incorporated herein by reference in its entirety.

[0002] The present invention relates to potassium hydrogen alkyl hydroxamate salts and compositions, formulations containing such compounds and compositions, methods for producing and using such compounds, compositions and formulations, and their use, particularly in cosmetic applications.

Background Art

[0003] Organic acids are well known for preserving foods, cosmetics, personal care products, and pharmaceuticals. Examples include benzoic acid and sorbic acid. 1,2 . These compounds must be present in their acid form to effectively preserve formulations against microbial contamination and growth. As the pH of the formulation increases, the proportion of the organic acid present in the active acid form decreases, and the proportion of the inactive ionized or salt form increases. This phenomenon depends on the pK a of the organic acid, and the lower the pK a , the lower the pH of the formulation must be for the acid to provide effective preservation. Some pK a values of various acids are: salicylic acid, pK a = 3.0; benzoic acid, pK a = 4.2; p - anisic acid, pK a = 4.5; levulinic acid, pK a = 4.6; and sorbic acid, pK a = 4.8.

[0004] However, in acid form, these compounds have limited water solubility and are poorly soluble in water, making formulation difficult. Previous solutions involved preparing pre-solubilized blends of organic acids using water-miscible carrier solvents, such as glycols, polyols, and aromatic alcohols. An alternative and more economical solution involves adding organic acids in salt form, such as sodium benzoate or potassium sorbate, to facilitate dissolution, and then lowering the solution pH with an acid to obtain a homogeneous solution of the organic acid. Nevertheless, such compounds generally have a low pK a Based on the values, pH levels above 5.5 are considered inefficient or ineffective in controlling microbial contamination and inhibiting microbial growth.

[0005] Caprylhydroxamic acid ("CHA") is particularly useful as a chelating agent that also helps protect formulations from microbial contamination and growth. CHA and related C6-C 10 A key advantage of alkylhydroxamic acids is that the hydroxamic acid functional group has a much higher pK compared to conventional organic acids. a This means that the acid remains in its acidic form even at higher pH values. For example, Figure 1 shows that CHA (pKa ≈ 9.4) is primarily present in a more beneficial acidic form over a much wider pH range compared to benzoic acid and sorbic acid. This greater pH flexibility gives compounders greater discretion in selecting ingredients and setting formulation specifications.

[0006] Similar to conventional organic acids, CHA and related C6-C6 10 Alkylhydroxamic acids exhibit limited water solubility and are poorly soluble in water. However, CHA and related C6-C 10 The alkali metal salts of alkylhydroxamic acids exhibit remarkably high water solubility, readily dissolving in aqueous media at higher concentrations than their acidic forms. Therefore, CHA or related C6-C 10 It is expected that by utilizing the salt form of alkylhydroxamic acid, the compound can be rapidly dissolved in water, and then the pH of the resulting solution can be lowered to obtain the acid form in the solution.

[0007] Patent Document 1 for Hughes discloses that the potassium salt of alkylhydroxamic acid can be isolated as a crystalline solid, i.e., KH(AH)2, which is an "aggregate" in which one equivalent of potassium hydrogen alkylhydroxamate is combined with one equivalent of alkylhydroxamic acid. 3 This discovery was confirmed by Hope and co - researchers in 2010. 4 However, Hughes is related to alkaline compositions with a pH value exceeding 11 and does not teach about the addition of acids and / or the decrease in pH. Hughes is also related to the flotation of ores and does not mention the use of alkylhydroxamates for the control of microbial growth or microbial contamination.

[0008] Patent Document 2 for Inolex and Patent Document 3 for Unilever disclose alkylhydroxamic acids and salts, but do not distinguish between sodium salts or potassium salts and do not mention the KH(AH)2 form either. Also, Patent Document 3 only discloses monovalent salts (i.e., MAH, where M is an alkali metal and AH is an alkylhydroxamate) and compositions buffered to pH 7 - 8 and formulated with bases such as sodium hydroxide and triethanolamine.

[0009] From the position of potassium relative to sodium in the periodic table, it is generally recognized that potassium salts are more basic than sodium salts. The higher alkalinity of potassium hydroxide compared to sodium hydroxide is because the atomic radius of potassium is larger, so the attraction to the hydroxide counter - ion is weaker, and potassium hydroxide can be more easily ionized when dissolved in an aqueous solution.

Prior Art Documents

Patent Documents

[0010]

Patent Document 1

Patent Document 2

[0011] It is undesirable to rely on significant pH adjustments in cosmetic formulations. Alkylhydroxamic acids and salts that do not require significant pH adjustments are still needed, and it is preferable that these alkylhydroxamic acids and salts are considered "natural" or "sustainable" by consumers of cosmetic formulations. [Means for solving the problem]

[0012] Surprisingly, the applicants have identified CHA and related C6-C 10 We discovered that the potassium hydrogen salt of alkylhydroxamic acid is actually less alkaline than its sodium counterpart. This is beneficial for formulations where the desired pH is approximately 8 or lower, as it dramatically reduces the pH adjustment required for in situ generation of the alkylhydroxamic acid form.

[0013] In some embodiments, the present invention is Equation (I): MH(AH)2(I) (In the formula, M is an alkali metal cation essentially composed of potassium, H is hydrogen, AH is C6~C 10 Compounds of alkylhydroxamic acid anions, A sufficient amount of pH adjuster to bring the pH value of the formulation to approximately 8 or less, Regarding formulations containing the above.

[0014] The formulation described in the previous paragraph, in which the pH adjuster is an organic acid.

[0015] A formulation as described in any of the preceding paragraphs, either individually or in combination thereof, wherein the organic acid is selected from the group consisting of benzoic acid, sorbic acid, p-anisic acid, levulinic acid, salicylic acid, citric acid, lactic acid, malic acid, succinic acid, malonic acid, fumaric acid, anisic acid, glycolic acid, salts thereof, and combinations thereof.

[0016] The formulations described in the preceding paragraph, either alone or in combination, wherein AH is caprylhydroxamate.

[0017] A formulation according to any of the preceding paragraphs, either alone or in combination, wherein MH(AH)2 is potassium hydrogen caprylhydroxamate.

[0018] A formulation containing approximately 0.2 ppm to approximately 2200 ppm of potassium, either alone or in combination, as described in any of the preceding paragraphs.

[0019] A formulation described in any of the preceding paragraphs, either alone or in combination, wherein substantially all of the carbon present in the compound of formula (I) is biobased.

[0020] A formulation described in any of the preceding paragraphs, either alone or in combination, wherein the compound of formula (I) is present in an aqueous formulation at a solution concentration of approximately 0.0002% to approximately 2.0%, or approximately 0.0002% to approximately 1.5%, or approximately 0.0002% to approximately 1.0%, or approximately 0.0002% to approximately 0.5%.

[0021] A formulation, either alone or in combination, described in any of the preceding paragraphs, wherein the pH value of the formulation is approximately 3.5 to approximately 7.9, or approximately 4.0 to approximately 7.5, or approximately 4.5 to approximately 7.5.

[0022] A formulation, either alone or in combination, described in any of the preceding paragraphs, having a free hydroxylamine concentration of less than 1000 ppm, less than 500 ppm, less than 200 ppm, or less than 100 ppm.

[0023] A formulation, either alone or in combination, described in any of the preceding paragraphs, which substantially does not contain free hydroxylamine.

[0024] A formulation, either alone or in combination, described in any of the preceding paragraphs, having a turbidity of less than approximately 20 NTU, or less than approximately 10 NTU, or less than approximately 5 NTU, or less than approximately 2.5 NTU.

[0025] A formulation described in any of the preceding paragraphs, either alone or in combination therewith, which is a personal care product, home care product, textile care product, institutional care product, pharmaceutical product, animal product, food product, or industrial product, or a component thereof.

[0026] A personal care product, or a formulation, selected from the group consisting of cosmetics, conditioners for hair, nails, skin or textiles, shampoos, hair styling products, oils or waxes for grooming facial hair, permanent wave solutions, hair coloring agents, facial cleansers or body soaps, makeup removers, cleansing lotions, emollient lotions or creams, bar soaps, liquid soaps, shaving creams, foams or gels, sunscreens, sunscreen gels, lotions or creams, deodorants or antiperspirants, moisturizing gels, shaving foams, face powders, foundations, lipsticks, blushes, eyeliners, wrinkle creams or anti-aging creams, eyeshadows, eyebrow pencils, mascaras, mouthwashes, toothpastes, oral care products, skin cleansing products, textile cleaning products, dishwashing products, hair or fur cleaning products, and lotions or moisturizers, either alone or in combination, as described in any of the preceding paragraphs.

[0027] In other embodiments, the present invention is A medium-chain terminal diol and Equation (I): MH(AH)2(I) (In the formula, M is an alkali metal cation essentially composed of potassium, H is hydrogen, AH is C6~C 10 Compounds of alkylhydroxamic acid anions, C6~C 10 Alkylhydroxamic acid and Optionally, an organic acid or a salt thereof, This relates to an antimicrobial composition containing [specific components].

[0028] A composition containing approximately 11 ppm to approximately 11,000 ppm of potassium, either alone or in combination, as described in any of the preceding paragraphs.

[0029] Approximately 0.01 wt% to 10 wt% of the compound of formula (I), approximately 10 wt% to 80 wt% of the medium-chain terminal diol, and approximately 1 wt% to 20 wt% of the C6-C6 compound. 10 A composition comprising an alkylhydroxamic acid, either alone or in combination, as described in any of the preceding paragraphs.

[0030] A composition according to any of the preceding paragraphs, either individually or in combination thereof, wherein the medium-chain terminal diol is at least one of glyceryl monoesters, glyceryl monoethers, 1,2-alkanediols, and combinations thereof.

[0031] The composition according to any one of the preceding paragraphs, either alone or in combination, wherein the medium-chain terminal diol is a glyceryl monoester selected from the group consisting of glyceryl monolaurate, glyceryl monocaprate, glyceryl monopelargonate, glyceryl monocaprylate, glyceryl monoheptanoate, and glyceryl monoundecylenate.

[0032] The composition according to any of the preceding paragraphs, either alone or in combination, wherein the medium-chain terminal diol is a glyceryl monoether selected from the group consisting of ethylhexylglycerin, methylheptylglycerin, caprylyl glyceryl ether, heptylglycerin, or cyclohexylglycerin.

[0033] The composition according to any of the preceding paragraphs, either alone or in combination, wherein the middle-chain terminal diol is a 1,2-alkanediol selected from the group consisting of 1,2-pentanediol, 1,2-hexanediol, 1,2-heptanediol, caprylyl glycol, and 1,2-decanediol.

[0034] A composition according to any of the preceding paragraphs, either individually or in combination thereof, wherein any organic acid is selected from the group consisting of benzoic acid, sorbic acid, p-anisic acid, levulinic acid, salicylic acid, citric acid, lactic acid, malic acid, malonic acid, succinic acid, fumaric acid, anisic acid, glycolic acid, salts thereof, and combinations thereof.

[0035] A composition further comprising a polyol, either alone or in combination, as described in any of the preceding paragraphs.

[0036] A composition as described in any of the preceding paragraphs, either individually or in combination thereof, wherein the polyol is selected from the group consisting of glycerin, propanediol, 1,2-propanediol (propylene glycol), 1,3-butanediol, 2,3-butanediol, 1,4-butanediol, 1,2-pentadiol, sorbitol, sorbitan, isosorbide, and combinations thereof.

[0037] A composition according to any of the preceding paragraphs, either alone or in combination thereof, further comprising at least one additional component selected from surfactants, emollients, moisturizers, conditioning agents, surfactants, bleaching or whitening agents, fragrances, colorants, exfoliants, antioxidants, plant components, mica, smectite, thickeners, cannabinoids, oils, dyes, waxes, amino acids, nucleic acids, vitamins, hydrolyzed proteins and their derivatives, glycerin derivatives, glyceride esters, enzymes, anti-inflammatory agents, bactericides, antifungal agents, disinfectants, antioxidants, UV absorbers, dyes and pigments, preservatives, sunscreen activators, antiperspirant activators, oxidizing agents, pH balancers, moisturizers, peptides and their derivatives, anti-aging activators, hair growth activators, anti-cellulite activators, and combinations thereof.

[0038] A composition according to any of the preceding paragraphs, either alone or in combination, wherein a 2% aqueous solution of the composition has a turbidity of less than about 5 NTU.

[0039] A composition, either alone or in combination, according to any of the preceding paragraphs, wherein a 2% aqueous solution of the composition has a pH value of approximately 9 or less.

[0040] A composition, either alone or in combination, according to any of the preceding paragraphs, wherein the pH value of the composition is approximately 3.5 to approximately 7.9, or approximately 4.0 to approximately 7.5, or approximately 4.5 to approximately 7.5.

[0041] A formulation comprising the antimicrobial composition described in any of the preceding paragraphs, either alone or in combination, wherein the antimicrobial composition is present in the formulation in an amount ranging from approximately 0.25 wt% to approximately 5.0 wt%.

[0042] A formulation according to any of the preceding paragraphs, either alone or in combination, wherein the antimicrobial composition is present in the formulation in an amount ranging from approximately 0.50 wt% to approximately 2.5 wt%.

[0043] A formulation containing approximately 0.2 ppm to approximately 2200 ppm of potassium, either alone or in combination, as described in any of the preceding paragraphs.

[0044] A formulation described in any of the preceding paragraphs, either alone or in combination therewith, which is a personal care product, home care product, textile care product, institutional care product, pharmaceutical product, animal product, food product, or industrial product, or a component thereof.

[0045] A personal care product, or a formulation, selected from the group consisting of cosmetics, conditioners for hair, nails, skin or textiles, shampoos, hair styling products, oils or waxes for grooming facial hair, permanent wave solutions, hair coloring agents, facial cleansers or body soaps, makeup removers, cleansing lotions, emollient lotions or creams, bar soaps, liquid soaps, shaving creams, foams or gels, sunscreens, sunscreen gels, lotions or creams, deodorants or antiperspirants, moisturizing gels, shaving foams, face powders, foundations, lipsticks, blushes, eyeliners, wrinkle creams or anti-aging creams, eyeshadows, eyebrow pencils, mascaras, mouthwashes, toothpastes, oral care products, skin cleansing products, textile cleaning products, dishwashing products, hair or fur cleaning products, and lotions or moisturizers, either alone or in combination, as described in any of the preceding paragraphs.

[0046] In yet another embodiment, the present invention is Equation (I): MH(AH)2(I) (In the formula, M is an alkali metal cation essentially composed of potassium, H is hydrogen, AH is C6~C 10 The preparation of an aqueous solution containing a compound (which is an alkylhydroxamic acid anion), Combining the aqueous solution with at least one other component, Add a sufficient amount of pH adjuster to bring the pH value of the formulation to approximately 8 or less, Furthermore, the pH adjuster should be added before, after, or in combination with at least one other component; The present invention relates to a method for preparing a compound that includes [a specific compound].

[0047] The method described in the preceding paragraph, wherein the compound of formula (I) is present in an aqueous solution at a concentration of approximately 0.0002% to approximately 2.0%, or 0.0002% to approximately 1.5%, or approximately 0.0002% to approximately 1.0%, or approximately 0.0002% to approximately 0.5%.

[0048] The method described in either the preceding paragraph, either alone or in combination, wherein the addition is performed before the combination.

[0049] The method described in the preceding paragraph, either individually or in combination, wherein the addition is made after the combination.

[0050] The method according to any of the preceding paragraphs, either alone or in combination, wherein the pH adjuster is an organic acid.

[0051] The method according to any of the preceding paragraphs, wherein the organic acid is selected from the group consisting of benzoic acid, sorbic acid, p-anisic acid, levulinic acid, salicylic acid, citric acid, lactic acid, malic acid, malonic acid, succinic acid, fumaric acid, anisic acid, glycolic acid, salts thereof, and combinations thereof, either individually or in combination thereof.

[0052] The method according to either of the preceding paragraphs, either alone or in combination, wherein AH is caprylhydroxamate.

[0053] The method according to any of the preceding paragraphs, either alone or in combination, wherein MH(AH)2 is potassium hydrogen caprylhydroxamate.

[0054] The method described in either of the preceding paragraphs, either alone or in combination, wherein substantially all of the carbon present in the compound of formula (I) is biobased.

[0055] The method described in either of the preceding paragraphs, either alone or in combination, wherein at least one other component comprises a medium-chain terminal diol.

[0056] The method according to any of the preceding paragraphs, either alone or in combination, wherein the mid-chain terminal diol is a glyceryl monoester, glyceryl monoether, or 1,2-alkanediol.

[0057] The method according to any of the preceding paragraphs, either alone or in combination, wherein the medium-chain terminal diol is a glyceryl monoester selected from the group consisting of glyceryl monolaurate, glyceryl monocapreate, glyceryl monocaprylate, and glyceryl undecylenate.

[0058] The method according to either the preceding paragraph, alone or in combination, wherein the medium-chain terminal diol is a glyceryl monoether selected from the group consisting of ethylhexylglycerin, methylheptylglycerin, caprylyl glyceryl ether, heptylglycerin, or cyclohexylglycerin.

[0059] The method according to any of the preceding paragraphs, either alone or in combination, wherein the mid-chain terminal diol is a 1,2-alkanediol selected from the group consisting of 1,2-pentanediol, 1,2-hexanediol, caprylyl glycol, and 1,2-decanediol.

[0060] At least one other component is C6-C 10The method described in any of the preceding paragraphs, either alone or in combination, comprising alkylhydroxamic acid.

[0061] The method described in either of the preceding paragraphs, either alone or in combination, wherein at least one other component comprises a polyol.

[0062] The method according to either the preceding paragraph, wherein the polyol is selected from the group consisting of glycerin, propanediol, 1,2-propanediol (propylene glycol), 1,3-butanediol, 1,4-butanediol, 1,2-pentadiol, sorbitol, sorbitan, isosorbide, and combinations thereof, either individually or in combination.

[0063] The method according to any of the preceding paragraphs, either individually or in combination thereof, wherein at least one other component is selected from surfactants, emollients, moisturizers, conditioning agents, surfactants, bleaching or whitening agents, fragrances, colorants, exfoliants, antioxidants, plant components, mica, smectite, thickeners, cannabinoids, oils, dyes, waxes, amino acids, nucleic acids, vitamins, hydrolyzed proteins and their derivatives, glycerin derivatives, glyceride esters, enzymes, anti-inflammatory agents, bactericides, antifungal agents, disinfectants, antioxidants, UV absorbers, dyes and pigments, preservatives, sunscreen surfactants, antiperspirant surfactants, oxidizing agents, pH balancers, moisturizers, peptides and their derivatives, anti-aging surfactants, hair growth agents, anti-cellulite surfactants, and combinations thereof.

[0064] The method according to any of the preceding paragraphs, either alone or in combination, wherein the pH value of the composition is approximately 3.5 to approximately 7.9, or approximately 4.0 to approximately 7.5, or approximately 4.5 to approximately 7.5.

[0065] The method described in either of the preceding paragraphs, either alone or in combination, wherein the formulation has a turbidity of less than approximately 10 NTU.

[0066] The methods described in either the preceding paragraph, either individually or in combination, may include preparing a formulation containing the antimicrobial composition described above. [Brief explanation of the drawing]

[0067] [Figure 1] This figure shows the degree of ionization of benzoic acid, sorbic acid, and caprylhydroxamic acid as a function of solution pH. [Figure 2] This figure shows the solution pH as a function of concentration for NaCH and KH(CH)2. [Figure 3] This figure shows the titration curves for NaCH and KH(CH)2. [Modes for carrying out the invention]

[0068] Before describing the compounds, compositions, and methods of the present invention in particular, it should be understood that the invention is not limited to the specific processes, compositions, or methods described, as these may be modified. It should also be understood that the terms used in the description are intended solely to describe specific versions or embodiments and are not intended to limit the scope of the invention, which is limited only by the appended claims. Unless otherwise specified, all technical and scientific terms used herein have the same meaning as those commonly understood by those skilled in the art. Any methods and materials similar to or equivalent to those described herein may be used in carrying out or testing embodiments of the present invention, but preferred methods, devices, and materials are described herein. All publications referenced herein constitute part of this specification by literal quotation. Nothing in this specification should be construed as acknowledging that the present invention has no prior rights to such disclosure for the sake of prior art.

[0069] Furthermore, when used herein and in the appended claims, it should be noted that the singular forms "a," "an," and "the" refer to multiple objects unless otherwise clearly indicated by the context. For example, a reference to "cell" refers to one or more cells and their equivalents that are known to those skilled in the art.

[0070] Unless otherwise specified, "%" can refer to either weight percentage or volume percentage.

[0071] "Cosmetic-acceptable" means suitable for use in contact with the skin without excessive toxicity, incompatibility, instability, irritation, allergic reactions, etc.

[0072] In some embodiments, the present invention relates to compositions and / or formulations having antimicrobial properties. As used herein, “antimicrobial” means inhibiting the growth of undesirable microorganisms and / or killing undesirable microorganisms in order to improve the shelf life of a product.

[0073] Where applicable, chemical substances are designated by their INCI names in accordance with the International Nomenclature Guidelines for Cosmetic Ingredients. Additional information, including suppliers and trade names, can be found in the appropriate INCI monograph in the 16th edition of the International Dictionary of Cosmetic Ingredients Handbook published by the Personal Care Products Council (Washington, DC), or online in the Personal Care Products Council's INCIpedia database (http: / / incipedia.personalcarecouncil.org).

[0074] Among many embodiments, the present invention includes bio-based compositions. The production of bio-based compositions requires the use of bio-based or “natural” source materials. Examples of bio-based compositions are those prepared from biological source materials (e.g., from current sustainable agricultural activities such as fermentation, algae, plants, or vegetables; for example, preferably obtained from plant sources using non-genetically modified organisms or biomass) and are non-petrochemical (e.g., obtained from sustainable tree and plant farms operating in the 21st century, as opposed to fossil sources such as petroleum, natural gas, or coal). Such source materials are referred to herein as “natural” and “renewable” (i.e., “sustainable”) and are known in the art as non-petroleum source materials. Furthermore, such materials are formed from “new” carbon rather than petroleum or other fossil fuel sources (“old” carbon). Such products are referred to herein as “natural” products and are known in the art as non-petrochemical or “bio” products. As used herein, the term “sustainable” refers to starting materials, reaction products, compositions, and / or formulations derived from renewable source materials. Therefore, the term “sustainable” is in contrast to “unsustainable” starting materials, reaction products, compositions, and / or formulations that contain carbon from limited natural resources such as fossil fuels (e.g., petroleum or coal) and natural gas. For this reason, natural or bio-products are non-petrochemical and / or not petrochemical, but rather produced from sustainable and renewable sources. True natural products (bio-products) are formed using biomass (e.g., substances stored from carbon cycling processes in living plants, roots, etc., or released from or by the respiration or excrement of animals). When carbon is broken down and decomposes under pressure over millions of years, fossil fuels (petrochemical sources of carbon) are produced. Bio-compounds as used herein include and / or are intended to be sustainable materials derived from carbon from recently existing (or previously existing) plant sources / biomass, with materials derived from fossil fuels expressly excluded.

[0075] The compositions and / or formulations of the present invention can be identified by their bio-based carbon content and distinguished from prior art compositions and / or formulations. In some embodiments, the bio-based carbon content can be determined by radiocarbon dating, which determines the relative age of materials composed of organic (i.e., carbon-containing) substances. Radiocarbon is carbon-14 (i.e., " 14 It is an unstable isotope of carbon, known as "C". 14 C emits radiant energy in the form of beta particles at a very consistent rate (i.e., the half-life of radioactive carbon is 5730 years), and eventually becomes the more stable nitrogen-14 ( 14 It is an unstable isotope that decays into N). Petroleum-based (i.e., petrochemical-derived) raw materials originate from plants and animals buried millions of years ago, and therefore the radiocarbon (i.e., 14 C) is lost through radioactive decay. The ASTM international standard sets out a test standard for determining the certainty of "bio-based compounds" using radiocarbon, which can be found in ASTM D6866-16. This standard distinguishes between newer carbon and carbon derived from fossil fuels or petroleum and petrochemical sources, i.e., "older carbon" in recent or current biomass. 14 Since the amount of C is known, the percentage of carbon originating from renewable sources can be estimated from total organic carbon analysis, which provides the necessary data to determine whether a compound originates from truly “natural” and / or “sustainable” (“renewable”) source materials, or conversely, from “old” sequestration compounds (i.e., petrochemical or petroleum-based sources). The use of petroleum-based (also referred to as “fossil”) source materials is generally considered unsustainable; that is, old carbon is unsustainable, not a renewable source material, and furthermore, not considered “natural” and / or “sustainable” in the art.

[0076] In some embodiments, the formulations and / or compositions of the present invention contain biobased carbon as substantially all of the carbon present in the mixture of compounds, which may refer to a biobased carbon content of at least 90%, at least 95%, or at least 98%.

[0077] In some embodiments, the compositions of the present invention, as determined according to ASTM D6866, are in the current atmosphere 14 The C content is substantially equivalent to 14 Contains C content. In some embodiments, the compositions of the present invention, as determined according to ASTM D6866, are in the current atmosphere. 14 C content of at least about 90%, at least about 95%, at least about 98%, or at least about 99% 14 It contains C. In some embodiments, the composition of the present invention, as determined according to ASTM D6866, contains 10 C. 12 At least about 0.8 per carbon atom 14 C atom, 10 present in the composition 12 At least about 1.0 per carbon atom 14 C atoms, or 10 present in the composition 12 At least about 1.2 per carbon atom 14 Contains a carbon atom.

[0078] As used herein, “sustainable” refers to materials derived from renewable sources. In contrast, “unsustainable” refers to materials derived from limited natural resources such as fossil fuels (e.g., oil, natural gas, coal, etc.).

[0079] Formulations containing potassium hydrogenated alkylhydroxamate In some embodiments, the present invention relates to formulations comprising potassium hydrogenated alkylhydroxamate salts. These formulations can be used in a variety of applications. They may be personal care products, home care products, textile care products, institutional care products, pharmaceuticals, animal products, food products, or industrial products, or components thereof. In some embodiments, the formulation may be a personal care product or a component thereof. Personal care products include cosmetics, conditioners for hair, nails, skin, or textiles, shampoos, hair styling products, oils or waxes for facial hair care, permanent wave solutions, hair coloring agents, facial cleansers or body soaps, makeup removers, cleansing lotions, emollient lotions or creams, bar soaps, liquid soaps, shaving creams, foams or gels, sunscreens, sunscreen gels, lotions or creams, deodorants or antiperspirants, moisturizing gels, shaving foams, foundations, lipsticks, blushes, eyeliners, wrinkle creams or anti-aging creams, mascaras, mouthwashes, toothpastes, oral care products, skin cleansing products, textile cleaning products, dishwashing products, hair or fur cleaning products, and toners or moisturizers.

[0080] The alkylhydroxamic acid potassium salts used in combination with the formulations, compositions, products, and methods of the present invention include C6-C 10 Alkylhydroxamic acid, or C6-C 10 Examples include alkylhydroxamic acid anions or salts thereof. Formulations containing potassium hydrogen alkylhydroxamic acid salts may include aqueous formulations.

[0081] Formulations containing potassium hydrogenated alkylhydroxamate are defined by formula (I): MH(AH)2(I) (In the formula, M is an alkali metal cation essentially composed of potassium, H is hydrogen, AH is C6~C 10The compound may contain an alkylhydroxamic acid anion. The molar ratio of M to alkylhydroxamic acid nitrogen (N) in the alkylhydroxamic acid potassium salt KH(AH)2 is preferably about 0.3 to about 0.7, more preferably about 0.4 to about 0.6, and even more preferably about 0.45 to about 0.55.

[0082] M in formula (I) is essentially an alkali metal cation consisting of potassium. In other words, M may be the absence of other alkali metal cations. In some embodiments, M does not contain or substantially contains alkali metal cations other than potassium. Preferably, M does not contain or substantially contains sodium. Substantially sodium-free may mean that sodium is present in amounts less than 5000 ppm, preferably less than 4000 ppm, and more preferably less than 2000 ppm. In some embodiments, sodium is present in amounts less than 1000 ppm, for example less than 500 ppm, less than 200 ppm, or less than 100 ppm. The inventors have surprisingly found that the potassium hydrogenated alkylhydroxamate salts of the formulations disclosed herein require significantly less pH adjuster, as supported in the following examples. This is desirable because it allows for easier processing with fewer pH adjusters and at the same time provides consumers with personal care products containing minimal additives.

[0083] AH according to equation (I) is C6~C 10 Alkylhydroxamate anions, such as hexanohydroxamate (caprohydroxamate), heptanohydroxamate, octanohydroxamate (caprylohydroxamate or caprylhydroxamate), nonanohydroxamate (pelargohydroxamate), decanohydroxamate (caprinohydroxamate), or combinations thereof. In some embodiments, AH according to formula (I) is caprylhydroxamate, where C6~C 10The alkylhydroxamate anion is a C8 alkylhydroxamate. In some embodiments, when AH is a caprylhydroxamate, MH(AH)2 is potassium hydrogen caprylhydroxamate KH(C8H 16 It is O2N2.

[0084] The aqueous formulation containing the alkylhydroxamic acid potassium salt as described above contains water, for example, deionized water. The water in the aqueous formulation according to the present invention, which contains the alkylhydroxamic acid potassium salt compound and a pH adjuster, may be present in amounts ranging from about 50 wt% to about 99 wt%, for example, 60 wt% to 99 wt%, 70 wt% to 99 wt%, 80 wt% to 99 wt%, 85 wt% to 99 wt%, 90 wt% to 99 wt%, 95 wt% to 99 wt%, or 98 wt% to 99 wt%. As for the lower limit, water may be present in amounts greater than 50 wt%, for example, greater than 60 wt%, greater than 70 wt%, greater than 80 wt%, greater than 85 wt%, greater than 90 wt%, greater than 95 wt%, or greater than 98 wt%.

[0085] C6~C 10 As described above, the carbon atoms present in the compound of formula (I), such as alkylhydroxamic acid anions, may be bio-based. In some embodiments, substantially all of the carbon atoms present in the compound of formula (I) are bio-based. This is important because the compound according to formula (I) is useful as a personal care product as described above, and non-petrochemical components are highly valued by consumers for their safety and efficacy.

[0086] A formulation containing potassium hydrogen alkylhydroxamate may further contain a pH adjuster in an amount sufficient to yield an aqueous formulation pH of about 8 or less. In some embodiments, the pH adjuster is an organic acid.

[0087] The organic acids described herein are of the formula RA, where R is the organic (carbon-containing) part and A is the acidic group. The acidic group may include proton-donating acids such as Brønsted acids. The acidic group may include carboxylic acids (COOH), sulfonic acids (SO3H), etc. For example, the organic acids described herein may include carboxylic acids and R-COOH, where R is the organic part (carbon-containing). Examples of carboxylic acids used herein include benzoic acid, hexanoic acid, heptanoic acid, octanoic acid, nonanoic acid, decanoic acid, dodecanoic acid, undecylenic acid, palmitic acid, isopalmitic acid, isostearic acid, stearic acid, behenic acid, and their derivatives and combinations.

[0088] Organic acids can be selected from the group consisting of benzoic acid, sorbic acid, p-anisic acid, levulinic acid, salicylic acid, citric acid, lactic acid, malic acid, fumaric acid, anisic acid, glycolic acid, ethanesulfonic acid, acetic acid, their salts, and combinations thereof.

[0089] In some cases, pH adjusters lower the pH of aqueous formulations containing potassium hydrogenated alkylhydroxamate salts to a lower pH than when no pH adjuster is used with the compound. The amount of pH adjuster required depends on the concentration of potassium hydrogenated alkylhydroxamate salt in the aqueous solution. For example, the pH of potassium hydrogenated caprylhydroxamate salt in a 1% aqueous solution is 9.0 to 10.0. In comparison, the pH of sodium caprylhydroxamate salt in a 1% aqueous solution is 11.0 to 11.5. The target pH level of formulations disclosed herein, such as personal care products, is less than pH 8. When using potassium hydrogenated alkylhydroxamate salt compounds described herein, the amount of pH adjuster required to achieve the desired pH below 8 is minimal.

[0090] In comparison, the amount of pH adjuster required when using sodium alkylhydroxamate is significantly higher than when using potassium alkylhydroxamate. Surprisingly, it was found that the amount of pH adjuster required when using potassium alkylhydroxamate is less than the amount required when using sodium alkylhydroxamate. In some embodiments, by weight, formulations using potassium alkylhydroxamate require 25 wt% to 70 wt% less pH adjuster than formulations using sodium alkylhydroxamate. The amount of pH adjuster required varies depending on the formulation, as the requirements are also influenced by other components in the formulation matrix. In other embodiments, by molar basis, formulations using potassium alkylhydroxamate require 50 mol% less pH adjuster than formulations using sodium alkylhydroxamate to achieve complete neutralization to the acid form.

[0091] In some embodiments, the addition of a pH adjuster alters the pH of the aqueous formulation so that the pH value is in the range of about 3.5 to about 7.9. The pH value of the aqueous formulation according to the present invention, comprising an alkylhydroxamic acid potassium salt compound and a pH adjuster, can be in the range of, for example, about 3.5 to about 7.9, for example, 4.0 to about 7.5, about 4.5 to about 7.5, about 5.0 to about 7.0, or about 5.5 to about 6.5. With respect to the upper limit, the addition of a pH adjuster alters the pH of the aqueous formulation so that the pH value can be less than 8, for example, less than 7.9, less than 7.5, less than 7.0, or less than 6.5. With respect to the lower limit, the addition of a pH adjuster alters the pH value of the aqueous formulation so that the pH value can be greater than 3.5, for example, greater than 4.0, greater than 4.5, greater than 5.0, or greater than 5.5.

[0092] The concentration of the compound according to formula (I) may vary depending on the final formulation and / or the final use of the formulation. The compound of formula (I) can be present in an aqueous formulation at a solution concentration of about 0.0002% to about 2.0%. The concentration of the compound of formula (I) may be present in an aqueous formulation at a solution concentration in the range of, for example, about 0.0002% to about 2.0%, for example, about 0.0002% to about 1.5%, about 0.0002% to about 1.0%, about 0.0002% to about 0.5%, or about 0.0002% to about 0.1%. Regarding the upper limit, the solution concentration may be less than 2.0%, for example less than 1.5%, less than 1.0%, less than 0.5%, or less than 0.2%. Regarding the lower limit, the solution concentration may be greater than 0.0002%, for example greater than 0.001%, greater than 0.01%, greater than 0.05%, or greater than 0.1%.

[0093] The aqueous formulations containing alkylhydroxamate potassium hydrogen salts described herein contain potassium, for example, potassium is present at a concentration greater than about 0.2 ppm. The potassium content can be measured by atomic absorption spectroscopy or inductively coupled plasma mass spectrometry (ICP-MS). The concentration of potassium (K) may be present in aqueous formulations containing alkylhydroxamate potassium hydrogen salt in the range of about 0.2 ppm K to about 2200 ppm K, for example, 0.2 ppm to 2000 ppm, 1.0 ppm to 1800 ppm, or 10 ppm to 1600 ppm, or 100 ppm to 1400 ppm. As an upper limit, the concentration may be less than 2200 ppm, for example, less than 2000 ppm, less than 1800 ppm, less than 1600 ppm, less than 1400 ppm, less than 1200 ppm, or less than 1000 ppm. Regarding the lower limit, the concentration can be greater than 0.2 ppm, for example, greater than 1.0 ppm, greater than 10 ppm, greater than 100 ppm, or greater than 200 ppm.

[0094] In formulations containing potassium hydrogenated alkylhydroxamate as described herein, it may be preferable to maintain a free hydroxylamine concentration of less than 100 ppm. Free hydroxylamine (NH2OH) is an undesirable inorganic compound in the formulations disclosed herein due to health and safety concerns. The free hydroxylamine content can be measured by high-performance liquid chromatography (HPLC) with spectroscopic detection. 5 The concentration of free hydroxylamine may be present in the formulation at concentrations in the range of, for example, about 0 ppm to about 100 ppm, for example, 0 ppm to 100 ppm, 0 ppm to 50 ppm, or 0 ppm to 20 ppm, or 0 ppm to 10 ppm. Regarding the upper limit, the concentration may be less than 100 ppm, for example, less than 80 ppm, less than 50 ppm, less than 40 ppm, less than 20 ppm, less than 10 ppm, or less than 5 ppm. In some embodiments, the formulation may contain no free hydroxylamine or substantially no free hydroxylamine, for example, less than 1 ppm. In some embodiments, the free hydroxylamine concentration may be below the detection limit, for example, less than 0.1 ppm.

[0095] Formulations containing the compound of formula (I) may have a turbidity of less than about 10 turbidimetric units (NTU). Turbidity is important so that the formulation can be easily incorporated into end-use products that are intended to be clear or transparent. For this reason, the turbidity of the clear and / or transparent formulations intended herein should be as low as possible for a given formulation. Turbidity is measured by turbidimetric turbidity measurement using an instrument such as HF Scientific's Micro 100 bench turbidimeter. The turbidity of formulations containing potassium alkylhydroxamate salts may be in the range of, for example, about 0 NTU to about 20 NTU, e.g., 0.05 NTU to 15 NTU, 0.05 NTU to 10 NTU, or 0.05 NTU to 5 NTU. As an upper limit, the turbidity may be less than 20 NTU, e.g., less than 15 NTU, less than 10 NTU, less than 5 NTU, or less than 2.5 NTU. In some embodiments, the formulation has a turbidity of less than about 1 NTU in a 2% aqueous solution in deionized water. In some embodiments, the turbidity is 0 or essentially 0, and is, for example, below a reliable detection limit.

[0096] Antimicrobial composition containing potassium alkylhydroxamate and medium-chain terminal diol Multi-component (i.e., multi-component) blends are also disclosed herein and are suitable for use in formulations as antimicrobial compositions. In embodiments, the antimicrobial compositions of the present invention may comprise a potassium hydrogen alkylhydroxamate salt as described above, and additionally a medium-chain terminal diol (MCTD). The potassium hydrogen alkylhydroxamate salt in these embodiments may be a compound of formula (I) as described above. These compositions may also be used in or as components of formulations for personal care products or other uses as described above. Potassium hydrogen alkylhydroxamate salts can act synergistically with other components, such as MCTD.

[0097] In some embodiments, the present invention relates to an antimicrobial composition comprising a potassium hydrogenated alkylhydroxamate salt, which can be used in formulations for various applications. The antimicrobial composition or formulation of the present invention may be a personal care product, a home care product, a textile care product, a facility care product, a pharmaceutical product, a veterinary product, a food product, or an industrial product, or a component thereof. In some embodiments, the composition may be used in a formulation of a personal care product, or may be a component thereof. Personal care products include cosmetics, conditioners for hair, nails, skin, or textiles, shampoos, hair styling products, oils or waxes for facial hair care, permanent wave solutions, hair coloring agents, facial cleansers or body soaps, makeup removers, cleansing lotions, emollient lotions or creams, bar soaps, liquid soaps, shaving creams, foams or gels, sunscreens, sunscreen gels, lotions or creams, deodorants or antiperspirants, moisturizing gels, shaving foams, face powders, foundations, lipsticks, blushes, eyeliners, wrinkle creams or anti-aging creams, eyeshadows, eyebrow pencils, mascaras, mouthwashes, toothpastes, oral care products, skin cleansing products, textile cleaning products, dishwashing products, hair or fur cleaning products, and toners or moisturizers.

[0098] In these embodiments, the antimicrobial composition of the present invention, comprising an alkylhydroxamic acid potassium hydrogen salt, comprises a compound according to formula (I) as described above, a medium-chain terminal diol, and C6-C 10 The present invention may contain an alkylhydroxamic acid and optionally an organic acid or a salt thereof, or any other component. The antimicrobial composition of the present invention containing potassium hydrogen alkylhydroxamic acid salt may be non-aqueous.

[0099] For use in cosmetic, toiletry, and pharmaceutical applications, the most preferred diols for use in the compositions described herein are medium-chain linear vicinal diols that exhibit antimicrobial activity at relatively low usage levels. In some embodiments, the medium chain length is C4-C for the diol.10Such diols include 1,2-pentanediol, 1,2-hexanediol, 1,2-heptanediol, caprylyl glycol, and 1,2-decanediol. Other vicinal diols useful in the compositions described herein include molecules derived from glycerin. Glycerin can react with other molecules at the 1st or 3rd position, leaving two adjacent hydroxyl groups. For example, glyceryl monoethers such as ethylhexylglycerin, marketed by INOLEX, Inc. as Lexgard® E, or methylheptylglycerin, marketed by INOLEX, Inc. as Lexgard® MHG Natural MB, are useful liquid vicinal diols with antimicrobial properties. Glyceryl monoesters, such as glyceryl monolaurate, glyceryl monocaprate, glyceryl monopelargonate, glyceryl monoheptanoate, or glyceryl monocaprylate, which is LEXGARD® GMCY marketed by INOLEX, Inc. (Philadelphia, Pa.), are also useful antimicrobial vicinaldiols. For preservation of cosmetics, toiletries, and pharmaceuticals, vicinaldiols are known to be effective against bacteria and yeast, but weak against fungi. In the book *Preservatives for Cosmetics*, 2nd ed, (2006), pg. 102, the author states that vicinaldiols have "the weakest activity against all of these, with respect to fungi." In the paper "The Self-Preserving Challenge" by D. Smith et al., Cosmetic & Toiletries, No. 1, 115, No. 5 (May 2000), it is stated that vicinaldiol has bacterial activity, but "its activity against Aspergillus species is limited."Aspergillus niger, also known as Aspergillus brasiliensis, is one of the microorganisms used in the CTFA challenge test; therefore, products containing vicinaldiol as the sole preservative ingredient as described herein may not pass the CTFA challenge test adequately.

[0100] In some embodiments, the mid-chain terminal diol is at least one of glyceryl monoesters, glyceryl monoethers, 1,2-alkanediols, and combinations thereof. The mid-chain terminal diol may be a glyceryl monoester selected from the group consisting of glyceryl monolaurate, glyceryl monocaprate, glyceryl monopelargonate, glyceryl monocaprylate, glyceryl monoheptanoate, and glyceryl monoundecylenate. The mid-chain terminal diol may be a glyceryl monoether selected from the group consisting of ethylhexylglycerin, methylheptylglycerin, caprylyl glyceryl ether, heptylglycerin, hexylglycerin, or cyclohexylglycerin. The mid-chain terminal diol may be a 1,2-alkanediol selected from the group consisting of 1,2-pentanediol, 1,2-hexanediol, 1,2-heptanediol, caprylyl glycol, and 1,2-decanediol.

[0101] The compositions of these embodiments also include chelating agents. Suitable chelating agents for use with the compositions, formulations, products and methods of the present invention include C6-C6. 10Examples of chelating agents include, but are not limited to, alkylhydroxamic acid or its alkylhydroxamate salts, tetrasodium glutamate diacetate, phytic acid or its salts, gluconic acid or its salts, galacturonic acid or its salts, galactaric acid or its salts, and combinations thereof. In some embodiments, the chelating agent is caprylhydroxamic acid, a hydroxamate of caprylhydroxamic acid, or a combination thereof. In some embodiments, the chelating agent essentially consists of caprylhydroxamic acid, a hydroxamate of caprylhydroxamic acid, or a combination thereof.

[0102] The antimicrobial composition and / or blend of the present invention used in formulations comprises at least the following components: potassium hydrogenated alkylhydroxamate, medium-chain terminal diol and C6-C6 10 Alkylhydroxamic acid. In some embodiments, the antimicrobial composition of the present invention comprises about 0.01% to about 10% of the compound of formula (I), about 10% to about 80% of a medium-chain terminal diol, and about 1% to about 20% of C6-C 10 It contains alkylhydroxamic acid, and the percentage composition is calculated on a weight basis. Any other components may be included in the antimicrobial composition as follows:

[0103] The antimicrobial composition of the present invention comprises a potassium hydrogenated alkylhydroxamate salt and contains, for example, a compound of formula (I) in an amount of about 0.01 wt% to about 10 wt%, for example, 0.02 wt% to 9.0 wt%, 0.03 wt% to 8.0 wt%, 0.04 wt% to 7.0 wt%, 0.05 wt% to 6.0 wt%, or 0.10 wt% to 5.0 wt%. Regarding the upper limit, the amount of the compound of formula (I) may be less than 10 wt%, for example, less than 9.0 wt%, less than 8.0 wt%, less than 7.0 wt%, less than 6.0 wt%, or less than 5.0 wt%. Regarding the lower limit, the amount of compound in formula (I) may be greater than 0.01 wt%, for example, greater than 0.02 wt%, greater than 0.03 wt%, greater than 0.04 wt%, greater than 0.05 wt%, or greater than 0.10 wt%.

[0104] The antimicrobial composition of the present invention contains medium-chain terminal diols in amounts ranging from about 10 wt% to about 80 wt%, for example, 15 wt% to 75 wt%, 20 wt% to 70 wt%, 25 wt% to 65 wt%, 30 wt% to 60 wt%, or 35 wt% to 55 wt%. Regarding the upper limit, the amount of medium-chain terminal diols may be less than 80 wt%, for example, less than 75 wt%, less than 70 wt%, less than 65 wt%, less than 60 wt%, or less than 55 wt%. Regarding the lower limit, the amount of medium-chain terminal diols may be greater than 10 wt%, for example, greater than 15 wt%, greater than 20 wt%, greater than 25 wt%, greater than 30 wt%, or greater than 35 wt%.

[0105] The antimicrobial composition of the present invention is C6~C 10 It contains alkylhydroxamic acid in amounts ranging from approximately 1 wt% to 20 wt%, for example, 1.5 wt% to 20 wt%, 2.0 wt% to 20 wt%, 1.0 wt% to 15 wt%, 1.5 wt% to 15 wt%, 2.0 wt% to 15 wt%, or 2.5 wt% to 15 wt%. Regarding the upper limit, C6 to C 10 The amount of alkylhydroxamic acid may be less than 20 wt%, for example, less than 19 wt%, less than 18 wt%, less than 17 wt%, less than 16 wt%, or less than 15 wt%. Regarding the lower limit, C6~C 10 The amount of alkylhydroxamic acid may be greater than 1 wt%, for example, greater than 1.0 wt%, greater than 1.5 wt%, greater than 2.0 wt%, or greater than 2.5 wt%.

[0106] Optionally, the antimicrobial composition of the present invention may include additional components or elements such as organic acids and / or polyols. The antimicrobial composition of the present invention may include organic acids selected from the group consisting of benzoic acid, sorbic acid, p-anisic acid, levulinic acid, salicylic acid, citric acid, lactic acid, succinic acid, malonic acid, malic acid, fumaric acid, anisic acid, glycolic acid, salts thereof, and combinations thereof. The antimicrobial composition of the present invention may include polyols selected from the group consisting of glycerin, propanediol, 1,2-propanediol (propylene glycol), 1,3-butanediol, 1,4-butanediol, 2,3-butanediol, 1,2-pentadiol, sorbitol, sorbitan, isosorbide, and combinations thereof. The antimicrobial composition of the present invention may include medium-chain amino acids (C6~C) of the amino acid glycine. 10 ) May include fatty acid amides, such as capryloyl glycine or its salts.

[0107] Optionally, the antimicrobial compositions of the present invention as described herein may include additional components or ingredients such as surfactants, emollients, moisturizers, conditioning agents, surfactants, bleaching or whitening agents, fragrances, colorants, exfoliants, antioxidants, plant components, mica, smectite, thickeners, cannabinoids, oils, dyes, waxes, amino acids, nucleic acids, vitamins, hydrolyzed proteins and their derivatives, glycerin derivatives (e.g., glyceride esters), enzymes, anti-inflammatory agents and other agents, bactericides, antifungal agents, disinfectants, antioxidants, UV absorbers, dyes and pigments, preservatives, sunscreen activators, antiperspirant activators, oxidizing agents, pH balancers, moisturizers, peptides and their derivatives, anti-aging activators, hair growth activators, anti-cellulite activators, and combinations thereof.

[0108] These components may be considered optional. In some cases, one or more of the above components may be explicitly excluded from the disclosed composition by means of the claim language in this section, for example. For example, the claim language may be modified to state that the disclosed composition, formulation, method, etc., does not utilize or contain one or more of the above optional components.

[0109] Subsequently, the antimicrobial composition of the present invention can be used in subsequent formulations, such as in the formulation of personal care products. The amount of the antimicrobial composition of the present invention may be present in the formulation in the range of, for example, about 0.25 wt% to about 5.0 wt%, for example, 0.30 wt% to 4.5 wt%, 0.35 wt% to 4.0 wt%, 0.40 wt% to 3.5 wt%, 0.45 wt% to 3.0 wt%, or 0.50 wt% to 2.5 wt%. Regarding the upper limit, the amount of the antimicrobial composition of the present invention in the formulation may be less than 5.0 wt%, for example, less than 4.5 wt%, less than 4.0 wt%, less than 3.5 wt%, less than 3.0 wt%, or less than 2.5 wt%. Regarding the lower limit, the amount of the antimicrobial composition of the present invention in the formulation may be greater than 0.25 wt%, for example, greater than 0.30 wt%, greater than 0.35 wt%, greater than 0.40 wt%, greater than 0.45 wt%, or greater than 0.50 wt%.

[0110] In some embodiments, a 2% aqueous solution of the antimicrobial composition of the present invention has a pH value of about 9 or less. The pH value can be in the range of, for example, about 3.5 to about 8.9, for example, 3.5 to about 7.9, 4.0 to about 7.5, about 4.5 to about 7.5, about 5.0 to about 7.0, or about 5.5 to about 6.5. Regarding the upper limit, the pH value may be less than 9, for example less than 8.9, less than 8.0, less than 7.5, less than 7.0, or less than 6.5. Regarding the lower limit, the pH value may be greater than 3.5, for example greater than 4.0, greater than 4.5, greater than 5.0, or greater than 5.5. These ranges and limits can also be applied to formulations containing these compositions.

[0111] Compositions comprising a potassium hydrogen alkylhydroxamate salt and a medium-chain terminal diol may have a lower turbidity than those described above, for example, less than about 5 NTU. As with the formulations discussed above, the turbidity of the antimicrobial compositions of the present invention as herein should be as low as possible. The turbidity of the antimicrobial compositions of the present invention may be in the range of, for example, about 0 NTU to about 10 NTU, for example, 0 NTU to 5 NTU, 0 NTU to 2.5 NTU, 0 NTU to 2 NTU, or 0 NTU to 1 NTU. With respect to the upper limit, the turbidity may be less than 10 NTU, for example, less than 5 NTU, less than 2.5 NTU, less than 2 NTU, less than 1.5 NTU, less than 1 NTU, or less than 0.5 NTU. In some embodiments, the antimicrobial compositions of the present invention have a turbidity of less than about 1 NTU in a 2% aqueous solution in deionized water. In some embodiments, the turbidity is 0 or essentially 0, for example, below the detection limit.

[0112] The antimicrobial compositions comprising alkylhydroxamic acid potassium salts described herein contain potassium (in the form of potassium ions), for example, potassium is present at a concentration greater than about 11 ppm. The concentration of potassium (K) may be present in the antimicrobial compositions of the present invention comprising alkylhydroxamic acid potassium salt in the range of about 11 ppm K to about 11,000 ppm K, for example, 11 ppm to 10,000 ppm, 50 ppm to 9,000 ppm, or 100 ppm to 8,000 ppm, or 200 ppm to 7,000 ppm. Regarding the upper limit, the concentration may be less than 11,000 ppm, for example, less than 10,000 ppm, less than 9,000 ppm, less than 8,000 ppm, or less than 7,000 ppm. Regarding the lower limit, the concentration may be greater than 11 ppm, for example, greater than 50 ppm, greater than 100 ppm, or greater than 200 ppm.

[0113] The antimicrobial compositions described above can be used in formulations. Formulations containing antimicrobial compositions contain potassium, for example, potassium is present at a concentration greater than approximately 0.2 ppm. The concentration of potassium (K) in a formulation (containing an antimicrobial composition containing an alkylhydroxamate potassium hydrogen salt) may range from approximately 0.2 ppm K to approximately 2200 ppm K, for example, 0.2 ppm to 2000 ppm, 1.0 ppm to 1800 ppm, or 10 ppm to 1600 ppm, or 100 ppm to 1400 ppm. Regarding the upper limit, the concentration may be less than 2200 ppm, for example, less than 2000 ppm, less than 1800 ppm, less than 1600 ppm, less than 1400 ppm, less than 1200 ppm, or less than 1000 ppm. Regarding the lower limit, the concentration can be greater than 0.2 ppm, for example, greater than 1.0 ppm, greater than 10 ppm, greater than 100 ppm, or greater than 200 ppm.

[0114] Method for preparing formulations and antimicrobial compositions containing alkylhydroxamic acid potassium hydrogen salts The formulations and antimicrobial compositions described herein, which contain potassium hydrogen alkylhydroxamate salts, are prepared by the method for preparing the formulations. In some embodiments, the method for preparing the formulations is formula (I): MH(AH)2(I) (In the formula, M is an alkali metal cation essentially composed of potassium, H is hydrogen, AH is C6~C 10 This involves preparing an aqueous solution containing a compound (which is an alkylhydroxamic acid anion).

[0115] This method further comprises combining an aqueous solution with at least one other component and adding a pH adjuster in an amount sufficient to produce a pH value of about 8 or less of the formulation. The pH adjuster may be added before, after, or in combination with at least one other component.

[0116] This method may include cases where the concentration of the compound according to formula (I) may vary depending on the final use of the final composition and / or formulation. This method may include the presence of the compound of formula (I) in an aqueous solution at a concentration of about 0.0002% to about 2.0%. For example, the compound of formula (I) can be present in an aqueous solution at a concentration in the range of about 0.0002% to about 2.0%, for example, about 0.0002% to about 1.5%, about 0.0002% to about 1.0%, about 0.0002% to about 0.5%, or about 0.0002% to about 0.1%. Regarding the upper limit, the concentration may be less than 2.0%, for example, less than 1.5%, less than 1.0%, less than 0.5%, or less than 0.2%. Regarding the lower limit, the concentration may be greater than 0.0002%, for example, greater than 0.001%, greater than 0.01%, greater than 0.05%, or greater than 0.1%. In some embodiments, as discussed above, substantially all of the carbon present in the compound of formula (I) is biobased.

[0117] This method involves combining a compound of formula (I) in an aqueous solution with at least one other component. This at least one other component is added in addition to (i) water and (ii) a pH adjuster in the aqueous solution. Examples of the at least one other component include a medium-chain terminal diol, a chelating agent, a polyol, or a combination thereof. The at least one other component to be combined may additionally or alternatively include the following additional components or components.

[0118] At least one other component of this method may include a medium-chain terminal diol, one of which is one of the above. In some embodiments, the medium-chain terminal diol is combined with an aqueous solution containing the compound of formula (I) in this method. In some embodiments, the medium-chain terminal diol is a glyceryl monoester, glyceryl monoether, or 1,2-alkanediol. The medium-chain terminal diol may be a glyceryl monoester selected from the group consisting of glyceryl monolaurate, glyceryl monocaprate, glyceryl monoperargonate, glyceryl monocaprylate, glyceryl monoheptanoate, and glyceryl monoundecylenate. The medium-chain terminal diol may be a glyceryl monoether selected from the group consisting of ethylhexylglycerin, methylheptylglycerin, caprylylglyceryl ether, heptylglycerin, or cyclohexylglycerin. The mid-chain terminal diol may be a 1,2-alkanediol selected from the group consisting of 1,2-pentanediol, 1,2-hexanediol, 1,2-heptanediol, caprylyl glycol, and 1,2-decanediol.

[0119] Suitable chelating agents for combination with an aqueous solution containing a compound of formula (I) in the method of the present invention include C6-C 10 Examples of chelating agents include, but are not limited to, alkylhydroxamic acid or its alkylhydroxamate salts, tetrasodium glutamate diacetate, phytic acid or its salts, gluconic acid or its salts, galacturonic acid or its salts, galactaric acid or its salts, and combinations thereof. In some embodiments, the chelating agent is caprylhydroxamic acid, a hydroxamate of caprylhydroxamic acid, or a combination thereof. In some embodiments, the chelating agent essentially consists of caprylhydroxamic acid, a hydroxamate of caprylhydroxamic acid, or a combination thereof.

[0120] Suitable polyols for use with the method of the present invention include, but are not limited to, polyols selected from the group consisting of glycerin, propanediol, 1,2-propanediol (propylene glycol), 1,3-butanediol, 2,3-butanediol, 1,4-butanediol, 1,2-pentanediol, sorbitol, sorbitan, isosorbide, and combinations thereof.

[0121] Optionally, at least one other component to be combined in the methods herein may additionally or alternatively include additional components or ingredients such as surfactants, emollients, humectants, conditioning agents, surfactants, bleaching or whitening agents, fragrances, colorants, exfoliants, antioxidants, plant components, mica, smectite, thickeners, cannabinoids, oils, dyes, waxes, amino acids, nucleic acids, vitamins, hydrolyzed proteins and their derivatives, glycerin derivatives (e.g., glyceride esters), enzymes, anti-inflammatory agents and other agents, bactericides, antifungal agents, disinfectants, antioxidants, UV absorbers, dyes and pigments, preservatives, sunscreen activators, antiperspirant activators, oxidizing agents, pH balancers, humectants, peptides and their derivatives, anti-aging activators, hair growth activators, anti-cellulite activators, and combinations thereof. These components may be considered optional in the methods herein.

[0122] This method involves adding a pH adjuster in an amount sufficient to produce a composition with a pH value of approximately 8 or less. The pH adjuster is added before, after, or in combination with at least one other component.

[0123] In some embodiments, the pH adjuster is added before combining it with at least one other component. In other embodiments, the pH adjuster is added after combining it with at least one other component. In yet another embodiment, the pH adjuster is added at the same time as combining it with at least one other component.

[0124] The pH adjuster used in this method may be an organic acid. The organic acid is selected from the group consisting of benzoic acid, sorbic acid, p-anisic acid, levulinic acid, salicylic acid, citric acid, lactic acid, malic acid, fumaric acid, succinic acid, malonic acid, anisic acid, glycolic acid, their salts, and combinations thereof. Preferred organic acids include citric acid, lactic acid, and malic acid.

[0125] In some embodiments, the method includes adding a pH adjuster in an amount sufficient to affect the pH value of the formulation to be in the range of about 3.5 to about 7.9. The pH value can be, for example, in the range of about 3.5 to about 7.9, e.g., 4.0 to about 7.5, about 4.5 to about 7.5, about 5.0 to about 7.0, or about 5.5 to about 6.5. Regarding the upper limit, the pH value may be less than 8, e.g., less than 7.9, less than 7.5, less than 7.0, or less than 6.5. Regarding the lower limit, the pH value may be greater than 3.5, e.g., greater than 4.0, greater than 4.5, greater than 5.0, or greater than 5.5. These ranges and limits can also be applied to formulations containing the antimicrobial composition of the present invention.

[0126] This method may include preparing a formulation containing an antimicrobial composition. Depending on the final formulation, additional components such as those described above may be added. The formulation or composition may be a component of personal care products, home care products, textile care products, institutional care products, pharmaceuticals, animal products, food products, or industrial products. Personal care products that can be manufactured by the methods described herein include cosmetics, conditioners for hair, nails, skin or textiles, shampoos, hair styling products, oils or waxes for grooming facial hair, permanent wave solutions, hair coloring agents, facial cleansers or body soaps, makeup removers, cleansing lotions, emollient lotions or creams, bar soaps, liquid soaps, shaving creams, foams or gels, sunscreens, sunscreen gels, lotions or creams, deodorants or antiperspirants, moisturizing gels, shaving foams, face powders, foundations, lipsticks, blushes, eyeliners, wrinkle creams or anti-aging creams, eyeshadows, eyebrow pencils, mascaras, mouthwashes, toothpastes, oral care products, skin cleansing products, textile cleaning products, dishwashing products, hair or fur cleaning products, and lotions or moisturizers.

[0127] These detailed descriptions are useful in illustrating the above general description and embodiments that form part of the present invention. These detailed descriptions are provided for illustrative purposes only and are not intended to limit the scope of the present invention. [Examples]

[0128] Example 1: Alkali metal salt of caprylhydroxamic acid Potassium hydrogen caprylate in Example 1 was prepared by the reaction of methyl caprylate with hydroxylamine according to the procedure described in Hughes (Patent Document 1). The resulting salt was isolated by filtration, purified by washing with methanol, and dried to a certain weight. Sodium caprylate (sodium octanohydroxamate monohydrate, more than 98% anhydrous) in Comparative Example 1 was purchased from TCI America and used as is.

[0129] Table 1 shows the theoretical and actual elemental compositions of Example 1 and Comparative Example 1, as well as those determined by elemental analysis (Galbraith Laboratories, Inc.). Elemental analysis revealed that the molar ratio of potassium to nitrogen in Example 1 (0.52) is consistent with the expected value for potassium hydrogen caprylhydroxamate (0.50), confirming that the compound in Example 1 follows the formula KH(CH)2 (where CH = caprylhydroxamate). In contrast, the molar ratio of sodium to nitrogen in Comparative Example 1 is observed to be 0.97, indicating the completely neutralized sodium salt NaCH of caprylhydroxamic acid.

[0130] TIFF0007905426000001.tif72170

[0131] Example 2: Solution of alkali metal salt of caprylhydroxamic acid Table 2 and Figure 2 show that an aqueous solution of potassium hydrogen caprylhydroxamate (Example 1) exhibits a pH value approximately 0.9 to 1.5 pH units lower than that of sodium caprylhydroxamate (Comparative Example 1) at a comparable concentration.

[0132] TIFF0007905426000002.tif43170

[0133] Example 3: Titration of aqueous solution of alkali metal salt of caprylhydroxamic acid Aqueous solutions (0.24 wt%) of KH(CH)2 and NaCH were prepared by dissolving the compounds from Example 1 and Comparative Example 1 in deionized water. The solutions were titrated with 0.1 N HCl solution using a Metrohm automatic titrator. Figure 3 shows the titration curves for both solutions. From both the titration curves and the determined titration endpoints (10.7 mL for KH(CH)2 and 18.4 mL for NaCH), it was found that the amount of acid required to neutralize the KH(CH)2 solution was significantly less, approximately 42%, compared to a NaCH solution of the same concentration.

[0134] Example 4: Micellar water formulation containing potassium hydrogen caprylhydroxamate Micellar water was prepared according to the formulation in Table 3 using the following procedure. Water (95% of the total water required for the batch) was added to a beaker of appropriate size with a known tare weight, equipped with an overhead mechanical stirrer and anchor-type blades. Mixing was started at a low to medium speed, and potassium hydrogen caprylhydroxamate (Example 1) was added to the water and mixed until completely dissolved. Polysorbate 20, butylene glycol, and methylheptylglycerin were added to the batch and mixed until a clear, homogeneous solution was formed. After recording the pH of the formulation, citric acid (10% aqueous solution) was added to adjust the pH to 6.5 ± 0.2, and the amount of citric acid solution required for pH adjustment was recorded. The remaining water was added in appropriate amounts until 100%, and after mixing the batch until homogeneous, it was transferred to a suitable container and stored. Comparative Example 2 was prepared according to the same procedure, except that sodium caprylhydroxamate (Comparative Example 1) was replaced with potassium hydrogen caprylhydroxamate.

[0135] Before pH adjustment, the micellar water formulation prepared with NaCH showed a significantly higher pH value compared to the formulation prepared with KH(CH)2 (pH=10.34 vs. pH=9.55). Therefore, the formulation prepared with KH(CH)2 required 65% less citric acid to adjust the pH to the target value of pH=6.5±0.2. The turbidity values ​​for Example 4 and Comparative Example 2 were 0.71 NTU and 0.77 NTU, respectively.

[0136] TIFF0007905426000003.tif119170

[0137] Example 5: Natural lotion formulation containing potassium hydrogen caprylhydroxamate A lotion containing 100% bio-based ingredients was prepared according to the formulation in Table 4 using the following procedure. Water (95% of the total water required for the batch), glycerin, methylheptylglycerin, and potassium hydrogen caprylhydroxamate (Example 1) were added to a beaker of appropriate size with a known tare weight, equipped with an overhead mechanical stirrer, anchor blades, and a heating hot plate. Mixing was started at a low to medium speed, and the xanthan gum was slowly separated into the aqueous phase and mixed until uniformly dispersed (no lumps remained). The mixture was then heated to 80°C. The oil phase components were combined in a separate beaker and heated to 80°C while mixing at a low speed until homogenized. The oil phase mixture was added to the 80°C aqueous phase mixture while mixing at a medium to high speed. After reaching a uniform appearance, the mixture was cooled to approximately 75°C and then homogenized at 3500 rpm for 3 minutes. After homogenization, the mixture was cooled to approximately 45°C to 50°C while stirring at a medium speed. After cooling to 30°C, the pH of the mixture was recorded, followed by the addition of citric acid (10% aqueous solution) to adjust the pH to 6.5 ± 0.2, and the amount of citric acid solution required for pH adjustment was recorded. The remaining water was added in appropriate amounts until the mixture reached 100%, and after mixing until homogeneous, it was transferred to a suitable container for storage. Comparative Example 2 was prepared according to the same procedure, except that sodium caprylhydroxamate (Comparative Example 1) was replaced with potassium hydrogen caprylhydroxamate.

[0138] Before pH adjustment, the lotion formulation prepared with NaCH showed a significantly higher pH value compared to the formulation prepared with KH(CH)2 (pH=8.62 vs. pH=8.11). Consequently, the formulation prepared with KH(CH)2 required 36% less citric acid to adjust the pH to the target value of pH=6.5±0.2.

[0139] TIFF0007905426000004.tif166170

[0140] Example 6: Natural shampoo formulation containing potassium hydrogen caprylhydroxamate Example 6 was prepared according to the formulation in Table 5. Water (95% of the total water required for the batch), potassium hydrogen caprylhydroxamate (Example 1), lauryl glucoside, sodium cocoyl glutamate, cocamidopropyl betaine, and methylheptylglycerin were added to a beaker of appropriate size with a known tare weight equipped with an overhead mechanical stirrer. The batch was mixed at a slow to medium speed until the contents were homogeneous. After recording the pH of the formulation, citric acid (10% aqueous solution) was added to adjust the pH to 6.5 ± 0.2, and the amount of citric acid solution required for pH adjustment was recorded. The remaining water was added in appropriate amounts until 100%, and the batch was mixed until homogeneous before being transferred to a suitable container and stored. Comparative Example 2 was prepared according to the same procedure, except that sodium caprylhydroxamate (Comparative Example 1) was replaced with potassium hydrogen caprylhydroxamate.

[0141] Before pH adjustment, the shampoo formulation prepared with NaCH showed a significantly higher pH value compared to the formulation prepared with KH(CH)2 (pH=11.46 vs. pH=10.71). Therefore, the formulation prepared with KH(CH)2 required 29% less citric acid to adjust the pH to the target value of pH=6.5±0.2. The turbidity values ​​for Example 6 and Comparative Example 4 were 7.30 NTU and 7.83 NTU, respectively.

[0142] TIFF0007905426000005.tif129170

[0143] Example 7: Antimicrobial composition using potassium hydrogen caprylhydroxamate An antimicrobial composition consisting of caprylhydroxamic acid, 1,2-hexanediol, propanediol, and potassium caprylhydroxamate was prepared according to the formulation in Table 6 and the following procedure: 1,2-hexanediol and propanediol were placed in a beaker of appropriate size with a known tare weight, equipped with an overhead mechanical stirrer. The mixture was heated to 40°C to 45°C while mixing at a low speed to ensure sufficient mixing without introducing air into the batch. Caprylhydroxamic acid and potassium caprylhydroxamate were slowly sprinkled into the batch and mixed until completely dissolved. The batch was cooled and stored in a suitable container. Comparative Example 5 was prepared in the same manner, except that potassium caprylhydroxamate was excluded from the batch.

[0144] The transparency of the antimicrobial compositions was evaluated by preparing aqueous solutions (2 wt%) in deionized water. The antimicrobial composition of Example 7 showed a turbidity of 0.12 NTU, while the antimicrobial composition of Comparative Example 5 showed a turbidity of 3.35 NTU. Furthermore, it was observed that the 2% aqueous solution of Example 7 maintained higher transparency over 48 hours compared to the 2% aqueous solution of Comparative Example 5.

[0145] TIFF0007905426000006.tif58170

[0146] Example 8: Microbiological challenge test of micellar water formulation containing KH(CH)2 A micellar water formulation was prepared according to Example 8 in Table 7 using the following procedure. Deionized water was placed in a beaker of appropriate size equipped with an overhead mechanical stirrer and anchor-type blades. Mixing was started at a low to medium speed, and polysorbate 20, butylene glycol, and KH(CH)2 were added to the batch and mixed until a clear, homogeneous solution was formed. Citric acid (20% aqueous solution) was added to adjust the pH to 6.5 ± 0.1. After mixing the batch until homogeneous, it was transferred to a suitable container and stored.

[0147] TIFF0007905426000007.tif91170

[0148] Comparative Example 6 was prepared according to the procedure used in Example 8, except that KH(CH)2 was excluded from the composition.

[0149] Microbiological challenge tests ("MCT") were performed on the micellar water formulations of Example 8 and Comparative Example 6. The challenge tests were conducted in accordance with USP and PCPC official test methods to determine the preservative efficacy of potassium hydrogen caprylhydroxamate KH(CH)2. The results are shown in Tables 8A and 8B.

[0150] TIFF0007905426000008.tif70170

[0151] TIFF0007905426000009.tif63170

[0152] Comparative Example 6, which does not contain potassium caprylhydroxamate hydrogen, fails to meet the PCPC acceptance criteria of a 99% reduction in bacteria and a 90% reduction in yeast and fungi within 7 days. Example 8, which contains potassium caprylhydroxamate hydrogen KH(CH)2 as an antimicrobial chelating agent to inhibit microbial growth, exhibits remarkable preservative efficacy. Example 8 meets and exceeds all USP, PCPC, and EP-B acceptance criteria for all organisms, and also meets the EP-A acceptance criteria of a 99% reduction in bacteria in 2 days (2log reduction), a 99.9% reduction in bacteria in 7 days (3log reduction), and a 99% reduction in yeast and mold in 14 days (2log reduction). Both Example 8 and Comparative Example 6 exhibit a pH value of 6.5 ± 0.1, which is considered an ideal environment for many microorganisms. Even under these conditions, Example 8 exhibits remarkable preservative efficacy.

[0153] Example 9: Micellar water formulation containing KH(CH)2 antimicrobial blend Example 9 was prepared according to the procedure used in Example 8, except that methylheptylglycerin (MHG) was added according to the formulation shown in Table 7. Example 9 has the same formulation as Example 4 used above.

[0154] The preservative efficacy of Example 9 was determined by conducting a challenge test in accordance with the USP and PCPC official test methods. The results are shown in Table 8C.

[0155] TIFF0007905426000010.tif67170

[0156] Example 9, which contained KH(CH)2 and MHG, showed remarkable preservative efficacy, meeting and exceeding the acceptance criteria of USP, PCPC, EP-A, and EP-B for all organisms. In contrast, Comparative Example 6 showed very low preservative efficacy and failed to meet the acceptance criteria.

[0157] Example 10: Natural lotion formulation containing KH(CH)2 antimicrobial blend A lotion containing 100% bio-based ingredients was prepared according to the formulation in Table 10 using the following procedure. Water and glycerin were placed in a beaker of appropriate size equipped with an overhead mechanical stirrer, anchor blades, and a heating hot plate. Mixing was started at a low to medium speed, and xanthan gum was slowly sprinkled into the aqueous phase and mixed until uniformly dispersed (no lumps remained). Methylheptylglycerin (MHG) and KH(CH)2 were added. The mixture was then heated to 80°C. The oil phase components were combined in a separate beaker and heated to 80°C while mixing at a low speed until uniform. The oil phase mixture was added to the 80°C aqueous phase mixture while mixing at a medium to high speed. After reaching a uniform appearance, the mixture was cooled to approximately 75°C and then homogenized at 5000 rpm for 3 minutes. The mixture was cooled to approximately 25°C while stirring at a medium speed. The batch pH was adjusted to 6.6 ± 0.1 using citric acid (20% aqueous solution). After mixing the composition until uniform, it was transferred to a suitable container and stored. The formulation of Example 10 corresponds to the formulation of Example 5 above.

[0158] TIFF0007905426000011.tif143170

[0159] Comparative Example 7: Natural lotion formulation that does not contain methylheptylglycerin (MHG) and KH(CH)2 Comparative Example 7 was prepared according to the procedure used in Example 10, except that methylheptylglycerin (MHG) and KH(CH)2 were excluded from the formulation. The formulation of Comparative Example 7 corresponds to the formulation of Comparative Example 3 above.

[0160] Microbiological challenge tests (MCTs) were conducted in accordance with the United States Pharmacopeia (USP) and PCPC official test methods to determine the preservative efficacy of KH(CH)2 and MHG in Example 10 and Comparative Example 7, thereby determining the preservative efficacy in the natural lotion formulations ("Personal Care Products Council Technical Guidelines. Microbiology Guidelines," (2018) Personal Care Products Council, Washington, DC). 7 (See also the cited literature). The results shown in Tables 10A and 10B represent the logarithmic values ​​of the number of viable bacteria measured after the end of the period. The row titled "Inoculation Level" indicates the initial number of organisms present at the start of the experiment.

[0161] Comparative Example 7, which does not contain KH(CH)2 and MHG, fails to meet the PCPC acceptance criteria of a 99% reduction in bacteria and a 90% reduction in yeast and fungi within 7 days. Example 10, which contains KH(CH)2 and MHG as antimicrobial agents to inhibit microbial growth, meets all USP 51 and PCPC acceptance criteria for all organisms and exceeds the acceptance criteria for Gram-positive bacteria, Gram-negative bacteria, and yeast. Furthermore, Example 10 was observed to meet the European Pharmacopoeia (EP) "B" criterion (EP-B) for the control of bacteria, yeast, and mold, namely a 99.9% reduction in bacteria (3-log reduction) and a 90% reduction in yeast and mold (1-log reduction) within 14 days (European Pharmacopeia (Ph. Eur.) 10.0, 2021, Section 5.1.3, Efficacy of Antimicrobial Preservation). 6 (See reference).

[0162] TIFF0007905426000012.tif67170

[0163] TIFF0007905426000013.tif67170

[0164] The present invention is not limited in scope by the specific embodiments described herein. In fact, various modifications of the present invention, in addition to those described herein, will be apparent to those skilled in the art from the above description and drawings. Such modifications are intended to be included in the appended claims.

[0165] It should be further understood that all values ​​are approximations and are provided for illustrative purposes only. All references cited and discussed herein constitute part of this specification by citation to the same extent that each reference constitutes part of this specification by citation.

[0166] References 1. M.J. Fevola, "Ingredient Profile: Benzoic Acid / Sodium Benzoate," Cosmetics and Toiletries 126(11):776-779 (Nov 2011). 2. M.J. Fevola, "Ingredient Profile: Sorbic Acid / Potassium Sorbate," Cosmetics and Toiletries 127(11):756-762 (Nov 2012). 3. U.S. Patent No. 7,007,805 B2, issued March 7, 2006. 4. G.A. Hope et al., "Spectroscopic characterization of n-octanohydroxamic acid and potassium hydrogen n-octanohydroxamate," Inorganica Chimica Acta 363:935-943 (2010). 5. Determination of hydroxylamine in aqueous solutions of pyridinium aldoximes by high-performance liquid chromatography with UV and fluorometric detection, W. D. Korte, J. Chromatog. A, 1992, 603(1-2), 145-150. 6. "Personal Care Products Council Technical Guidelines. Microbiology Guidelines," 2018 Personal Care Products Council, Washington, DC.

Claims

1. Equation (I): MH(AH) ２ (I) (In the formula, M is potassium, H is hydrogen, AH is C ６ ~C １０ Compounds of alkylhydroxamic acid anions, A sufficient amount of organic acid to produce a pH value of 8 or less in the formulation, Aqueous formulations containing the above.

2. C ４ ~C １０ A mid-chain terminal diol having the following chain length, Equation (I): MH(AH) ２ (I) (In the formula, M is potassium, H is hydrogen, AH is C ６ ~C １０ Compounds of alkylhydroxamic acid anions, C ６ ~C １０ an alkyl hydroxamic acid, and An antimicrobial composition containing the following:

3. AH is caprylhydroxamate, and MH(AH) ２ The formulation according to claim 1, wherein the compound is potassium hydrogen caprylhydroxamate.

4. The formulation according to claim 1, wherein the organic acid is selected from the group consisting of benzoic acid, sorbic acid, p-anisic acid, levulinic acid, salicylic acid, citric acid, lactic acid, malic acid, succinic acid, malonic acid, fumaric acid, anisic acid, glycolic acid, salts thereof, and combinations thereof.

5. The formulation according to claim 1, wherein the compound of formula (I) is present in the aqueous formulation at a solution concentration of 0.0002% to 2.0%, or 0.0002% to 1.5%, or 0.0002% to 1.0%, or 0.0002% to 0.5%, or the pH value of the formulation is 3.5 to 7.9, or 4.0 to 7.5, or 4.5 to 7.5, or the formulation has a free hydroxylamine concentration of less than 100 ppm, or less than 50 ppm, or less than 20 ppm, or less than 10 ppm, or the formulation has a turbidity of less than 20 NTU, or less than 10 NTU, or less than 5 NTU, or less than 2.5 NTU.

6. A compound of formula (I) in an amount of 0.01 wt% to 10 wt%, 10 wt% to 80 wt% of the aforementioned medium-chain terminal diol, 1 wt% to 20 wt% of the above C ６ ~C １０ Alkylhydroxamic acid and The composition according to claim 2, wherein the composition contains 11 ppm to 11,000 ppm of potassium.

7. The aforementioned mid-chain terminal diol is A glyceryl monoester selected from the group consisting of glyceryl monocaprate, glyceryl monoperargonate, glyceryl monocaprylate, and glyceryl monoheptanoate. Glyceryl monoethers selected from the group consisting of ethylhexylglycerin, methylheptylglycerin, caprylyl glyceryl ether, heptylglycerin, and cyclohexylglycerin. A 1,2-alkanediol selected from the group consisting of 1,2-pentanediol, 1,2-hexanediol, 1,2-heptanediol, caprylyl glycol, and 1,2-decanediol, And combinations thereof, The composition according to claim 2, wherein at least one of the following.

8. It further comprises polyols selected from the group consisting of glycerin, propanediol, 1,2-propanediol (propylene glycol), 1,3-butanediol, 2,3-butanediol, 1,4-butanediol, sorbitol, sorbitan, isosorbide and combinations thereof, or surfactants, emollients, moisturizers, conditioning agents, surfactants, bleaching agents or whitening agents, fragrances, colorants, exfoliants, antioxidants, plant components, mica, smectite, thickeners, cannabinoids, The composition according to claim 2, further comprising at least one additional component selected from oils, dyes, waxes, amino acids, nucleic acids, vitamins, hydrolyzed proteins and their derivatives, glycerin derivatives, glyceride esters, enzymes, anti-inflammatory agents, bactericides, antifungal agents, disinfectants, antioxidants, UV absorbers, dyes and pigments, antimicrobial agents, sunscreen activators, antiperspirant activators, oxidizing agents, pH balancers, moisturizers, peptides and their derivatives, anti-aging activators, hair growth activators, anti-cellulite activators, and combinations thereof.

9. The composition according to claim 2, wherein a 2% aqueous solution of the composition has a turbidity of less than 5 NTU and a pH value of 3.5 to 7.9, or 4.0 to 7.5, or 4.5 to 7.

5.

10. A composition comprising the composition according to claim 2, wherein the composition is present in the composition in an amount of 0.25 wt% to 5.0 wt%, or 0.50 wt% to 2.5 wt%.

11. The formulation according to claim 1 or 10, comprising 0.2 ppm to 2200 ppm of potassium.

12. The formulation according to claim 1 or 10, which is a personal care product, home care product, textile care product, institutional care product, pharmaceutical product, animal product, food product, or industrial product, or a component thereof.

13. A formulation according to claim 1 or 10, which is a personal care product selected from the group consisting of cosmetics, hair conditioners, nail conditioners, skin or textile conditioners, shampoos, hair styling products, oils or waxes for grooming facial hair, permanent wave solutions, hair coloring agents, facial cleansers or body soaps, makeup removers, cleansing lotions, emollient lotions or creams, bar soaps, liquid soaps, shaving creams, foams or gels, sunscreens, sunscreen gels, lotions or creams for sun treatment, deodorants or antiperspirants, moisturizing gels, shaving foams, face powders, foundations, lipsticks, blushes, eyeliners, wrinkle creams or anti-aging creams, eyeshadows, eyebrow pencils, mascaras, mouthwashes, toothpastes, oral care products, skin cleansing products, textile cleaning products, dishwashing products, hair or fur cleaning products, and lotions or moisturizers, or a component thereof.

14. Equation (I): MH(AH) ２ (I) (In the formula, M is potassium, H is hydrogen, AH is C ６ ~C １０ The preparation of an aqueous solution containing a compound (which is an alkylhydroxamic acid anion), The aqueous solution is combined with at least one other component, Add a sufficient amount of pH adjuster to achieve a pH value of 8 or less in the formulation, Furthermore, the pH adjusting agent may be added before, after, or in combination with at least one other component; A method for preparing a compound containing the above.

15. The formulation according to claim 1 or the composition according to claim 2, wherein substantially all of the carbon present in the compound of formula (I) is bio-based.

16. At least one other component is a medium-chain terminal diol, C ６ ~C １０ The method according to claim 14, comprising alkylhydroxamic acid, polyol, surfactant, emollient, moisturizing agent, conditioning agent, surfactant, bleaching agent or whitening agent, fragrance, colorant, exfoliant, antioxidant, plant component, mica, smectite, thickener, cannabinoid, oil, dye, wax, amino acid, nucleic acid, vitamin, hydrolyzed protein and its derivatives, glycerin derivative, glyceride ester, enzyme, anti-inflammatory agent, bactericide, antifungal agent, disinfectant, antioxidant, UV absorber, pigment, antimicrobial agent, sunscreen surfactant, antiperspirant surfactant, oxidizing agent, pH balancer, moisturizer, peptide and its derivatives, anti-aging surfactant, hair growth agent, anti-cellulite surfactant, and combinations thereof.

17. The antimicrobial composition according to claim 2, wherein the antimicrobial composition has a free hydroxylamine concentration of less than 200 ppm.

18. The formulation according to claim 1, wherein the formulation has a free hydroxylamine concentration of 0 to 100 ppm.

19. The formulation according to claim 1, wherein the formulation does not contain free hydroxylamine concentration.

20. The method according to claim 14, wherein substantially all of the carbon present in the compound of formula (I) is biobased.

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