Potassium hydrogen alkyl hydroxamate and compositions containing 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 August 20, 2021, and is incorporated herein by reference.

[0002] The present invention relates to potassium alkylhydroxamic acid hydrogen salt compounds and compositions, formulations containing the compounds and compositions, methods of making and using the compounds, compositions and formulations, and applications thereof, including, particularly, cosmetic applications. [Background technology]

[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 the formulation against microbial contamination and growth. As the pH of a formulation increases, the proportion of organic acids present in their active acid form decreases and the proportion of inactive ionized or salt forms increases. This phenomenon is known as the pK a Depends on pK a The lower the pK of the various acids, the lower the pH of the formulation must be for the acid to provide effective preservation. a Values ​​are for salicylic acid, pK a =3.0;benzoic acid, pK a p-Anisic acid, pK = 4.2 a = 4.5; levulinic acid, pK a = 4.6; and sorbic acid, pK a =4.8.

[0004] However, in the acid form, these compounds have limited water solubility and are difficult to dissolve in water, making formulations difficult. Previous solutions have involved making a pre-solubilized blend of the organic acid with a water-miscible carrier solvent, such as glycols, polyols, aromatic alcohols, etc. An alternative, more economical solution is to add a salt form of the organic acid, such as sodium benzoate or potassium sorbate, to facilitate dissolution, and then use an acid to lower the solution pH to obtain a homogeneous solution of the organic acid. Nevertheless, such compounds generally have a low pK a From the values, a pH above 5.5 is not considered efficient or effective for controlling microbial contamination and inhibiting microbial growth.

[0005] Particularly useful is caprylhydroxamic acid ("CHA"), which is a chelating agent that also helps protect the formulation against microbial contamination and growth. CHA and related C6-C 10 An important advantage of alkylhydroxamic acids is that the hydroxamic acid functional group has a much higher pK a The advantage of CHA over its pH range is that it has a pKa of 9.4 and therefore remains in the acid form even at higher solution pH values. For example, Figure 1 shows that CHA (pKa ≈ 9.4) exists primarily in its more beneficial acid form over a much wider range of pH values ​​than benzoic acid and sorbic acid. This greater pH flexibility gives formulators greater latitude in selecting ingredients and setting formulation specifications.

[0006] As well as conventional organic acids, CHA and related C6-C 10 Alkylhydroxamic acids exhibit limited water solubility and are poorly soluble in water. However, CHA and related C6-C 10 The corresponding alkali metal salts of alkylhydroxamic acids are significantly more water soluble and more readily dissolve in aqueous media at higher concentrations than the acid form. 10 It is anticipated that the salt form of the alkylhydroxamic acid can be utilized to obtain the acid form in solution by rapidly dissolving the compound in water and subsequently lowering the pH of the resulting solution.

[0007] U.S. Patent No. 5,393,333 to Hughes discloses that potassium salts of alkylhydroxamic acids can be isolated as crystalline solids that are "aggregates" of one equivalent of potassium hydrogen alkylhydroxamate combined with one equivalent of alkylhydroxamic acid, i.e., KH(AH). 3 This finding was confirmed in 2010 by Hope and colleagues. 4 However, Hughes is directed to alkaline compositions having pH values ​​above 11 and does not teach the addition of acid and / or lowering of pH. Hughes is also directed to ore flotation and does not mention the use of alkyl hydroxamates for the control of microbial growth or microbial contamination.

[0008] US Patent No. 5,399,633 to Inolex and US Patent No. 5,399,633 to Unilever disclose alkylhydroxamic acids and salts, but do not distinguish between sodium or potassium salts, nor do they mention the KH(AH)2 form. US Patent No. 5,399,633 discloses only 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 a base, e.g., sodium hydroxide, triethanolamine.

[0009] It is generally accepted that potassium salts are more basic than sodium salts due to the position of potassium relative to sodium in the periodic table of the elements. Potassium hydroxide is more alkaline compared to sodium hydroxide because the larger atomic radius of potassium results in a weaker attraction to the hydroxide counterion, allowing potassium hydroxide to ionize more easily when dissolved in aqueous solution. [Prior art documents] [Patent documents]

[0010] [Patent Document 1] U.S. Patent No. 7,007,805 [Patent Document 2] International Publication No. 2009 / 070736 [Patent Document 3] International Publication No. 2010 / 069957 Summary of the Invention [Problem to be solved by the invention]

[0011] It is undesirable to rely on significant pH adjustment in cosmetic formulations, and there remains a need for alkylhydroxamic acids and salts that do not require significant pH adjustment, and which are preferably considered "natural" or "sustainable" by consumers of cosmetic formulations. [Means for solving the problem]

[0012] Applicants have surprisingly found that CHA and related C6-C 10 It has been discovered that the hydrogen potassium salts of alkylhydroxamic acids are in fact less alkaline than their sodium counterparts, which is beneficial in formulations of compositions where the desired pH is about 8 or less, since dramatically less pH adjustment of the formulation is required for in situ generation of the alkylhydroxamic acid form.

[0013] In some embodiments, the present invention provides a method for producing a cellular membrane comprising: Formula (I): MH(AH)2(I) wherein M is an alkali metal cation consisting essentially of potassium; H is hydrogen, AH is C6~C 10 an alkylhydroxamic acid anion; a pH adjuster in an amount sufficient to provide a pH value of the formulation of about 8 or less; The present invention relates to a formulation comprising:

[0014] The formulation of the preceding paragraph, wherein the pH adjuster is an organic acid.

[0015] The formulation according to any of the preceding paragraphs, alone or in combination, 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 combination described in the preceding paragraph, alone or in combination, wherein AH is caprylhydroxamate.

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

[0018] The formulation of any of the preceding paragraphs, alone or in combination, comprising from about 0.2 ppm to about 2200 ppm of potassium.

[0019] The formulation described in any of the preceding paragraphs, alone or in combination, wherein substantially all of the carbon present in the compound of formula (I) is bio-based.

[0020] The formulation according to any of the preceding paragraphs, alone or in combination, wherein the compound of formula (I) is present in the aqueous formulation in a solution concentration of from about 0.0002% to about 2.0%, or from about 0.0002% to about 1.5%, or from about 0.0002% to about 1.0%, or from about 0.0002% to about 0.5%.

[0021] The formulation according to any of the preceding paragraphs, alone or in combination, wherein the pH value of the formulation is from about 3.5 to about 7.9, or from about 4.0 to about 7.5, or from about 4.5 to about 7.5.

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

[0023] The formulation of any of the preceding paragraphs, alone or in combination, being substantially free of free hydroxylamine.

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

[0025] A formulation according to any of the preceding paragraphs, alone or in combination, which is, or is a component of, a personal care product, a home care product, a fabric care product, an institutional care product, a pharmaceutical product, an animal product, a food product or an industrial product.

[0026] The formulation according to any of the preceding paragraphs, alone or in combination, which is or is a component of a personal care product selected from the group consisting of cosmetics, hair, nail, skin or fabric conditioners, shampoos, hair styling products, oils or waxes for grooming facial hair, permanent wave solutions, hair colouring agents, face washes or body washes, make-up removing products, cleansing lotions, emollient lotions or creams, bar soaps, liquid soaps, shaving creams, foams or gels, sunscreens, gels, lotions or creams for treating sunburn, deodorants or antiperspirants, moisturising gels, shaving foams, face powders, foundations, lipsticks, blushes, eyeliners, wrinkle or anti-aging creams, eye shadows, eyebrow pencils, mascaras, mouthwashes, toothpastes, oral care products, skin cleansing products, fabric cleaning products, dish washing products, hair or fur cleaning products, and lotions or moisturising agents.

[0027] In another embodiment, the present invention provides a method for producing a composition comprising: A mid-chain end diol, Formula (I): MH(AH)2(I) wherein M is an alkali metal cation consisting essentially of potassium; H is hydrogen, AH is C6~C 10 an alkylhydroxamic acid anion; C6~C 10 Alkylhydroxamic acid, Optionally, an organic acid or a salt thereof; The present invention relates to an antimicrobial composition comprising:

[0028] The composition of any of the preceding paragraphs, alone or in combination, comprising from about 11 ppm to about 11,000 ppm of potassium.

[0029] About 0.01 wt% to about 10 wt% of the compound of formula (I), about 10 wt% to about 80 wt% of a mid-chain terminal diol, and about 1 wt% to about 20 wt% of a C6-C 10 A composition according to any of the preceding paragraphs, alone or in combination, comprising an alkyl hydroxamic acid.

[0030] The composition of any of the preceding paragraphs, alone or in combination, wherein the mid-chain end diol is at least one of a glyceryl monoester, a glyceryl monoether, a 1,2-alkanediol, and combinations thereof.

[0031] The composition of any of the preceding paragraphs, alone or in combination, wherein the mid-chain terminating 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 of any of the preceding paragraphs, alone or in combination, wherein the mid-chain end diol is a glyceryl monoether selected from the group consisting of ethylhexylglycerin, methylheptylglycerin, caprylyl glyceryl ether, heptylglycerin, or cyclohexylglycerin.

[0033] The composition of any of the preceding paragraphs, alone or in combination, wherein the mid-chain end 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] The composition according to any of the preceding paragraphs, alone or in combination, wherein the optional 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] The composition of any of the preceding paragraphs, alone or in combination, further comprising a polyol.

[0036] The composition of any of the preceding paragraphs, alone or in combination, 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-pentanediol, sorbitol, sorbitan, isosorbide, and combinations thereof.

[0037] The composition of any of the preceding paragraphs, alone or in combination, further comprising at least one additional ingredient selected from surfactants, emollients, humectants, conditioning agents, active agents, bleaching or whitening agents, fragrances, colorants, exfoliants, antioxidants, botanical ingredients, mica, smectites, thickeners, cannabinoids, oils, dyes, waxes, amino acids, nucleic acids, vitamins, hydrolyzed proteins and derivatives thereof, glycerin derivatives, glyceride esters, enzymes, anti-inflammatory agents, bactericides, antifungal agents, disinfectants, antioxidants, UV absorbers, dyes and pigments, preservatives, sunscreen actives, antiperspirant actives, oxidizing agents, pH balancing agents, moisturizers, peptides and derivatives thereof, anti-aging actives, hair growth agents, anti-cellulite actives, and combinations thereof.

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

[0039] The composition of any of the preceding paragraphs, alone or in combination, wherein a 2% aqueous solution of the composition has a pH value of about 9 or less.

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

[0041] A formulation comprising the antimicrobial composition of any of the preceding paragraphs, alone or in combination, wherein the antimicrobial composition is present in the formulation in a range of about 0.25 wt% to about 5.0 wt%.

[0042] The formulation described in any of the preceding paragraphs, alone or in combination, wherein the antimicrobial composition is present in the formulation in the range of about 0.50 wt% to about 2.5 wt%.

[0043] The formulation of any of the preceding paragraphs, alone or in combination, comprising from about 0.2 ppm to about 2200 ppm of potassium.

[0044] A formulation according to any of the preceding paragraphs, alone or in combination, which is, or is a component of, a personal care product, a home care product, a fabric care product, an institutional care product, a pharmaceutical product, an animal product, a food product or an industrial product.

[0045] The formulation according to any of the preceding paragraphs, alone or in combination, which is or is a component of a personal care product selected from the group consisting of cosmetics, hair, nail, skin or fabric conditioners, shampoos, hair styling products, oils or waxes for grooming facial hair, permanent wave solutions, hair colouring agents, face washes or body washes, make-up removing products, cleansing lotions, emollient lotions or creams, bar soaps, liquid soaps, shaving creams, foams or gels, sunscreens, gels, lotions or creams for treating sunburn, deodorants or antiperspirants, moisturising gels, shaving foams, face powders, foundations, lipsticks, blushes, eyeliners, wrinkle or anti-aging creams, eye shadows, eyebrow pencils, mascaras, mouthwashes, toothpastes, oral care products, skin cleansing products, fabric cleaning products, dish washing products, hair or fur cleaning products, and lotions or moisturising agents.

[0046] In yet another embodiment, the present invention provides a method for producing a method for manufacturing a semiconductor device comprising: Formula (I): MH(AH)2(I) wherein M is an alkali metal cation consisting essentially of potassium; H is hydrogen, AH is C6~C 10 preparing an aqueous solution containing a compound of formula (I) combining the aqueous solution with at least one other ingredient; adding a pH adjuster in an amount sufficient to provide a pH value of the formulation of about 8 or less; Additionally, the pH adjuster is added before, after, or in combination with at least one other ingredient; The present invention relates to a method for preparing a formulation comprising the steps of:

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

[0048] The method of any of the preceding paragraphs, alone or in combination, wherein the addition occurs prior to combining.

[0049] The method according to any of the preceding paragraphs, alone or in combination, where the addition occurs after the combination.

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

[0051] The method of any of the preceding paragraphs, alone or in combination, 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.

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

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

[0054] The method of any of the preceding paragraphs, alone or in combination, wherein substantially all of the carbon present in the compound of formula (I) is bio-based.

[0055] The method of any of the preceding paragraphs, alone or in combination, wherein at least one other component comprises a mid-chain end diol.

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

[0057] The method of any of the preceding paragraphs, alone or in combination, wherein the mid-chain end diol is a glyceryl monoester selected from the group consisting of glyceryl monolaurate, glyceryl monocaprate, glyceryl monocaprylate and glyceryl undecylenate.

[0058] The method of any of the preceding paragraphs, alone or in combination, wherein the mid-chain end diol is a glyceryl monoether selected from the group consisting of ethylhexylglycerin, methylheptylglycerin, caprylyl glyceryl ether, heptylglycerin, or cyclohexylglycerin.

[0059] The method of any of the preceding paragraphs, alone or in combination, wherein the mid-chain end 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 according to any of the preceding paragraphs comprising an alkylhydroxamic acid, either alone or in combination.

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

[0062] The method of any of the preceding paragraphs, alone or in combination, 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-pentanediol, sorbitol, sorbitan, isosorbide, and combinations thereof.

[0063] The method of any of the preceding paragraphs, alone or in combination, wherein the at least one other ingredient is selected from surfactants, emollients, humectants, conditioning agents, active agents, bleaching or whitening agents, fragrances, colorants, exfoliants, antioxidants, botanical ingredients, mica, smectites, thickeners, cannabinoids, oils, dyes, waxes, amino acids, nucleic acids, vitamins, hydrolyzed proteins and derivatives thereof, glycerin derivatives, glyceride esters, enzymes, anti-inflammatory agents, bactericides, antifungal agents, disinfectants, antioxidants, UV absorbers, dyes and pigments, preservatives, sunscreen actives, antiperspirant actives, oxidizing agents, pH balancing agents, moisturizing agents, peptides and derivatives thereof, anti-aging actives, hair growth agents, anti-cellulite actives, and combinations thereof.

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

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

[0066] The methods according to any of the preceding paragraphs, alone or in combination, may comprise preparing a formulation comprising an antimicrobial composition as described above. [Brief description of the drawings]

[0067] [Figure 1] FIG. 1 shows the degree of ionization as a function of solution pH for benzoic acid, sorbic acid and caprylhydroxamic acid. [Diagram 2] FIG. 1 shows solution pH as a function of concentration for NaCH and KH(CH). [Diagram 3] FIG. 1 shows titration curves of NaCH and KH(CH). DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS

[0068] Before describing the compounds, compositions, and methods of the present invention in particular, it is to be understood that the present invention is not limited to the particular process, composition, or method described, as such may be modified. It is also to be understood that the terms used in the description are only for the purpose of describing the particular versions or embodiments, and are not intended to limit the scope of the present invention, which is limited only by the appended claims. Unless otherwise specified, all technical and scientific terms used herein have the same meaning as commonly understood by one of ordinary skill in the art. Although any methods and materials similar or equivalent to those described herein can be used in the practice or testing of embodiments of the present invention, the preferred methods, devices, and materials are described herein. All publications mentioned herein are incorporated by reference in their entirety. Nothing herein should be construed as an admission that the present invention is not entitled to antedate such disclosure by virtue of prior invention.

[0069] Also, it should be noted that as used in this specification and the appended claims, the singular forms "a," "an," and "the" include plural referents unless the context clearly dictates otherwise. Thus, for example, reference to a "cell" is a reference to one or more cells and equivalents thereof known to those skilled in the art.

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

[0071] "Cosmetically acceptable" means suitable for use in contact with the skin without undue toxicity, incompatibility, instability, irritation, allergic response, and the like.

[0072] In some embodiments, the present invention relates to compositions and / or formulations that have antimicrobial properties. As used herein, "antimicrobial" means inhibiting the growth of and / or killing undesirable microorganisms to enhance the shelf life of a product.

[0073] Where applicable, chemicals are designated by their INCI names following the guidelines of the International Nomenclature of Cosmetic Ingredients. Additional information, including suppliers and trade names, can be found in the appropriate INCI monographs in the International Cosmetic Ingredient Dictionary and Handbook, 16th Edition, published by the Personal Care Products Council of America (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" feedstocks. Examples of bio-based compositions are those prepared from biologically derived feedstocks (e.g., by current sustainable agricultural practices such as fermentation, algae, plant or vegetable origin; e.g., obtained from plant sources, preferably using non-genetically modified organisms or biomass) and are non-petrochemically derived (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 feedstocks are referred to herein as "natural" and "renewable" (i.e., "sustainable") and are known in the art as non-petroleum derived feedstocks. Moreover, such materials are formed by "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-petrochemically derived or "bio" products. As used herein, the term "sustainable" refers to starting materials, reaction products, compositions and / or formulations that are derived from renewable sources. The term "sustainable" is therefore 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., oil or coal), natural gas, etc. For this reason, natural or bioproducts are non-petrochemically derived and / or are not derived from petrochemicals, but rather are produced from sustainable and renewable sources. True natural products (bioproducts) are formed using biomass (e.g., materials stored from carbon cycle processes in living plants, roots, etc., or released from animal respiration or waste, or by decomposition). When carbon is broken down and decomposed under pressure over millions of years, fossil fuels (sources of petrochemically derived carbon) are produced. Biocompounds herein are intended to include materials derived from carbon from recently existing (existing) plant sources / biomass and / or are sustainable, and materials derived from fossil fuels are expressly excluded.

[0075] The compositions and / or formulations of the present invention can be identified and distinguished from prior art compositions and / or formulations by their biobased carbon content. In some embodiments, the biobased carbon content can be measured by radiocarbon dating, which determines the relative age of materials composed of organic (i.e., carbon-containing) matter. Radiocarbon is the radioactive carbon found in the presence of carbon-14 (i.e., " 14 It is an unstable isotope of carbon known as 1H). 14 C releases radiant energy in the form of beta particles at a very consistent rate (i.e., radioactive carbon has a half-life of 5730 years) and eventually decays into the more stable nitrogen-14( 14 Petroleum-based (i.e., petrochemical-derived) feedstocks are derived from plants and animals buried millions of years ago, so the radioactive carbon (i.e., 14 C) has been lost to radioactive decay. ASTM International Standards has established a test standard for determining the authenticity of "biobased 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-derived sources, i.e., "old carbon." In recent or present biomass, 14 Since the amount of C is known, the percentage of carbon that is derived from renewable sources can be estimated from the total organic carbon analysis, providing the necessary data to determine whether a compound is truly derived from a "natural" and / or "sustainable" ("renewable") feedstock source, or conversely, whether it is derived from an "old" sequestration compound (i.e., petrochemical-derived or petroleum-based source). The use of petroleum-based (also referred to as "fossil-based") feedstocks is generally recognized as unsustainable, i.e., old carbon is unsustainable, is not a renewable feedstock, and is not considered "natural" and / or "sustainable" in the art.

[0076] In some embodiments, the blends and / or compositions of the present invention comprise bio-based carbon as substantially all of the carbon present in the mixture of compounds, which can refer to a bio-based carbon content of at least 90%, at least 95%, or at least 98%.

[0077] In some embodiments, the compositions of the present invention have a solubility in water that is less than 50% of the present atmospheric solubility as determined according to ASTM D6866. 14 C content substantially equal 14 In some embodiments, the compositions of the present invention have a carbon content that is less than 100% of the carbon content of current atmospheric carbon as determined according to ASTM D6866. 14 C content of at least about 90%, at least about 95%, at least about 98%, or at least about 99% 14 In some embodiments, the compositions of the present invention comprise at least 10 C present in the composition as determined according to ASTM D6866. 12 At least about 0.8 per carbon atom 14 C atoms 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 carbon atoms per 14 Contains C atoms.

[0078] By "sustainable" herein, applicants refer to materials that are derived from renewable sources. In contrast, "unsustainable" refers to materials that are derived from limited natural resources, such as fossil fuels (e.g., petroleum, natural gas, coal, etc.).

[0079] Formulations containing potassium hydrogen alkyl hydroxamate In some embodiments, the present invention relates to a formulation comprising an alkyl hydroxamic acid hydrogen potassium salt. The formulation can be used in a variety of applications. The formulation can be or be a component of a personal care product, a home care product, a fabric care product, an institutional care product, a pharmaceutical product, an animal product, a food product, or an industrial product. In some embodiments, the formulation can be or be a component of a personal care product. Personal care products include cosmetics, hair, nail, skin or fabric conditioners, shampoos, hair styling products, oils or waxes for grooming facial hair, permanent wave solutions, hair coloring agents, face or body washes, makeup remover products, cleansing lotions, emollient lotions or creams, bar soaps, liquid soaps, shaving creams, foams or gels, sunscreens, gels, lotions or creams for treating sunburn, deodorants or antiperspirants, moisturizing gels, shaving foams, foundations, lipsticks, blushes, eyeliners, wrinkle or anti-aging creams, mascara, mouthwashes, toothpastes, oral care products, skin cleansing products, fabric cleaning products, dishwashing products, hair or fur cleaning products, and toners or moisturizers.

[0080] The potassium hydrogen alkyl hydroxamate salts for use with the formulations, compositions, products and methods of the present invention include C6-C 10 Alkylhydroxamic acid, or C6-C 10 The alkylhydroxamic acid anion or salt thereof may be included. The formulation containing the alkylhydroxamic acid potassium hydrogen salt may include an aqueous formulation.

[0081] The formulations containing alkylhydroxamic acid hydrogen potassium salts have the formula (I): MH(AH)2(I) wherein M is an alkali metal cation consisting essentially of potassium; H is hydrogen, AH is C6~C 10The molar ratio of M to the alkylhydroxamic acid nitrogen (N) in the alkylhydroxamic acid potassium hydrogen 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 according to formula (I) is an alkali metal cation consisting essentially of potassium. In other words, M can be exclusive of other alkali metal cations. In some embodiments, M is free or substantially free of alkali metal cations other than potassium. Preferably, M is free or substantially free of sodium. Substantially free of sodium can mean that sodium is present in an amount less than 5000 ppm, preferably less than 4000 ppm, more preferably less than 2000 ppm. In some embodiments, sodium is present in an amount less than 1000 ppm, such as less than 500 ppm, less than 200 ppm, or less than 100 ppm. The inventors have surprisingly found that the potassium alkylhydroxamic acid hydrogen salt of the formulation disclosed herein requires significantly less pH adjuster, as supported in the examples below. This is desirable due to ease of processing with less pH adjuster, while providing consumers with a personal care product that contains minimal additives.

[0083] AH according to formula (I) is a C6-C 10 An alkylhydroxamate anion, such as hexanohydroxamate (caprohydroxamate), heptanohydroxamate, octanohydroxamate (caprylohydroxamate or caprylhydroxamate), nonanohydroxamate (pelargohydroxamate), decanohydroxamate (caprinohydroxamate), or a combination thereof. In some embodiments, AH according to formula (I) is caprylhydroxamate, where C6-C 10The alkyl hydroxamate anion is a C8 alkyl hydroxamate. In some embodiments, when AH is capryl hydroxamate, MH(AH)2 is potassium hydrogen caprylhydroxamate, KH(C8H 16 O2N)2.

[0084] The aqueous formulation comprising the alkylhydroxamic acid potassium hydrogen salt as described above comprises water, for example deionized water. The water in the aqueous formulation according to the present invention comprising the alkylhydroxamic acid potassium hydrogen salt compound and a pH adjuster can be present in an amount 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%. In terms of the lower limit, the water can be present in an amount greater than 50 wt%, for example greater than 60 wt%, 70 wt%, 80 wt%, 85 wt%, 90 wt%, 95 wt%, or greater than 98 wt%.

[0085] C6~C 10 Like the alkylhydroxamate anion, the carbon present in the compound of formula (I) may be bio-based, as described above. In embodiments, substantially all of the carbon present in the compound of formula (I) is bio-based. This is important because compounds according to formula (I) are useful in personal care products, as described above, and ingredients of non-petrochemical origin are valued by consumers for safety and efficacy.

[0086] The formulation comprising the alkylhydroxamic acid hydrogen potassium salt may further comprise a pH adjusting agent in an amount sufficient to provide a pH value of the aqueous formulation of less than or equal to about 8. In some embodiments, the pH adjusting agent is an organic acid.

[0087] The organic acids described herein are of the formula RA, where R is an organic (carbon-containing) moiety and A is an acidic group. The acid group may include a proton donor acid, such as a Bronsted acid. The acid group may include a carboxylic acid (COOH), a sulfonic acid (SO3H), and the like. For example, the organic acids herein may include a carboxylic acid, R-COOH, where R is an organic moiety (carbon-containing). Carboxylic acids used herein may 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 derivatives and combinations thereof.

[0088] The organic acid may 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, salts thereof, and combinations thereof.

[0089] In some cases, the pH adjuster causes the aqueous formulation containing the alkylhydroxamic acid hydrogen potassium salt to have a lower pH value than if the pH adjuster was not used in the compound. The amount of pH adjuster depends on the concentration of the alkylhydroxamic acid hydrogen potassium salt in the aqueous solution. For example, the pH value of caprylhydroxamic acid hydrogen potassium salt in a 1% aqueous solution is 9.0-10.0. In comparison, the pH value of caprylhydroxamic acid sodium salt in a 1% aqueous solution is 11.0-11.5. The target pH level of the formulations disclosed herein, such as personal care products, is less than pH 8. When using the alkylhydroxamic acid hydrogen potassium salt compounds described herein, minimal addition of pH adjuster is required to achieve the desired pH of less than 8.

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

[0091] In some embodiments, the addition of the pH adjuster changes the pH value of the aqueous formulation such 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 alkyl hydroxamic acid hydrogen 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. In terms of the upper limit, the addition of the pH adjuster changes the pH value of the aqueous formulation such 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. In terms of the lower limit, the addition of the pH adjuster changes the pH value of the aqueous formulation such 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 end use of the formulation. The compound of formula (I) may be present in the 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 the aqueous formulation at a solution concentration ranging, for example, from about 0.0002% to about 2.0%, such as from about 0.0002% to about 1.5%, from about 0.0002% to about 1.0%, from about 0.0002% to about 0.5% or from about 0.0002% to about 0.1%. In terms of the upper limit, the solution concentration may be less than 2.0%, such as less than 1.5%, less than 1.0%, less than 0.5% or less than 0.2%. In terms of the lower limit, the solution concentration may be greater than 0.0002%, such as greater than 0.001%, greater than 0.01%, greater than 0.05% or greater than 0.1%.

[0093] The aqueous formulations comprising alkylhydroxamic acid potassium salts described herein contain potassium, for example, potassium is present at a concentration of 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) can be, for example, present in the aqueous formulations comprising alkylhydroxamic acid potassium salts at a concentration ranging from 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. With respect to the upper limit, the concentration can 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. In terms of the lower limit, the concentration may be greater than 0.2 ppm, such as greater than 1.0 ppm, greater than 10 ppm, greater than 100 ppm or greater than 200 ppm.

[0094] In formulations containing alkylhydroxamic acid hydrogen potassium salts described herein, it may be preferable to maintain free hydroxylamine concentrations below 100 ppm. Free hydroxylamine NH2OH is an inorganic compound that is undesirable in the formulations disclosed herein due to health and safety concerns. 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 a concentration ranging from 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. With respect to 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 is free or substantially free of 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 compounds of formula (I) may have a turbidity of less than about 10 nephelometric turbidity units (NTU). Turbidity is important so that the formulation can be easily formulated into end-use products that are intended to be clear or transparent. For this reason, the turbidity of clear and / or transparent formulations contemplated herein should be as low as possible for a given formulation. Turbidity is measured by nephelometric turbidity measurement using an instrument such as HF Scientific's Micro 100 benchtop turbidimeter. The turbidity of formulations containing potassium alkyl hydroxamic acid hydrogen salts can range, for example, from about 0 NTU to about 20 NTU, such as 0.05 NTU to 15 NTU, 0.05 NTU to 10 NTU, or 0.05 NTU to 5 NTU. In terms of upper limits, the turbidity can be less than 20 NTU, such as 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 for a 2% aqueous solution in deionized water. In some embodiments, the turbidity is zero or essentially zero, eg, below the limit of reliable detection.

[0096] Antimicrobial composition comprising potassium hydrogen alkylhydroxamate and medium chain end diol Multi-component (i.e., multi-element) 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 include an alkylhydroxamic acid potassium salt as described above, and additionally a mid-chain end diol (MCTD). The alkylhydroxamic acid potassium salt of these embodiments may be a compound of formula (I) as described above. These compositions may also be used in or be a component of the formulation of personal care products or other applications as described above. The alkylhydroxamic acid potassium salt may act synergistically with other ingredients, such as MCTD.

[0097] In some embodiments, the present invention relates to antimicrobial compositions comprising potassium hydrogen alkyl hydroxamate salts that can be used in formulations for a variety of applications. The antimicrobial compositions or formulations of the present invention can be, or be a component of, personal care products, home care products, fabric care products, institutional care products, pharmaceutical products, animal products, food products, or industrial products. In some embodiments, the compositions can be used in, or be a component of, personal care product formulations. Personal care products include cosmetics, hair, nail, skin or fabric conditioners, shampoos, hair styling products, oils or waxes for grooming facial hair, permanent wave solutions, hair coloring agents, face or body washes, makeup remover products, cleansing lotions, emollient lotions or creams, bar soaps, liquid soaps, shaving creams, foams or gels, sunscreens, gels, lotions or creams for treating sunburn, deodorants or antiperspirants, moisturizing gels, shaving foams, face powders, foundations, lipsticks, blushes, eyeliners, wrinkle or anti-aging creams, eye shadows, eyebrow pencils, mascara, mouthwashes, toothpastes, oral care products, skin cleansing products, fabric cleaning products, dishwashing products, hair or fur cleaning products, and lotions or moisturizers.

[0098] In these embodiments, the antimicrobial compositions of the invention comprising an alkylhydroxamic acid potassium salt comprise a compound according to formula (I) as described above, a mid-chain terminal diol, and a C6-C 10 It may comprise an alkylhydroxamic acid and, optionally, an organic acid or salt thereof, or other optional ingredients.Antimicrobial compositions of the present invention comprising potassium hydrogen alkylhydroxamate salts 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 length linear vicinal diols that exhibit antimicrobial activity at relatively low use levels. In some embodiments, the medium chain length is C4 to C6 for the diols.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 be reacted with other molecules at the 1- or 3-position, leaving two adjacent hydroxyl groups. For example, glyceryl monoethers such as ethylhexylglycerin, available from INOLEX, Inc. as Lexgard™ E, or methylheptylglycerin, available from 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, commercially available as LEXGARD™ GMCY from INOLEX, Inc. (Philadelphia, Pa.), are also useful antimicrobial vicinal diols. For preservation of cosmetics, toiletries, and pharmaceuticals, vicinal diols are known to be effective against bacteria and yeasts, but weak against fungi. In the book D. Steinberg, Preservatives for Cosmetics. 2nd ed, (2006), pg. 102, the author states that, regarding vicinal diols, "the weakest activity of all of these is against fungi." In the article D. Smith et al., "The Self-Preserving Challenge," Cosmetic & Toiletries, No. 1, 115, No. 5 (May 2000), it is stated that vicinal diols have activity against bacteria, but "limited activity against Aspergillus."Aspergillus niger, also known as Aspergillus brasiliensis, is one of the organisms used in CTFA challenge testing; therefore, products with vicinal diols as the only preservative ingredient described herein may not pass CTFA challenge testing satisfactorily.

[0100] In some embodiments, the mid-chain end diol is at least one of a glyceryl monoester, a glyceryl monoether, a 1,2-alkanediol, and combinations thereof. The mid-chain end 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 end diol may be a glyceryl monoether selected from the group consisting of ethylhexylglycerin, methylheptylglycerin, caprylyl glyceryl ether, heptylglycerin, hexylglycerin, or cyclohexylglycerin. The mid-chain end 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 a chelating agent. Chelating agents suitable for use with the compositions, formulations, products and methods of the present invention include C6-C 10These include, but are not limited to, alkylhydroxamic acid or its alkylhydroxamate salt, 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 salt of caprylhydroxamic acid, or a combination thereof. In some embodiments, the chelating agent consists essentially of caprylhydroxamic acid, a hydroxamate salt of caprylhydroxamic acid, or a combination thereof.

[0102] The antimicrobial compositions and / or blends of the present invention used in the formulations include at least the following components: potassium alkyl hydroxamate hydrogen salt, a mid-chain end diol, and a C6-C 10 In some embodiments, the antimicrobial compositions of the present invention comprise from about 0.01% to about 10% of a compound of formula (I), from about 10% to about 80% of a mid-chain terminal diol, and from about 1% to about 20% of a C6-C 10 and alkylhydroxamic acid, the percent composition being calculated on a weight basis. Other optional ingredients may be included in the antimicrobial composition as described below.

[0103] The antimicrobial composition of the present invention comprises an alkylhydroxamic acid hydrogen potassium salt, for example, a compound of formula (I) in the range 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%. With respect to the upper limit, the amount of the compound of formula (I) can 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%. In terms of the lower limit, the amount of the compound of formula (I) may be greater than 0.01 wt%, such as 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 includes the mid-chain end diol in the range of 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%. In terms of the upper limit, the amount of the mid-chain end diol can 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%. In terms of the lower limit, the amount of the mid-chain end diol can be more than 10 wt%, for example, more than 15 wt%, more than 20 wt%, more than 25 wt%, more than 30 wt%, or more than 35 wt%.

[0105] The antimicrobial composition of the present invention is 10 The alkyl hydroxamic acid is contained in a range of about 1 wt% to about 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%. 10 The amount of alkyl hydroxamic 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%. 10 The amount of alkylhydroxamic acid can be greater than 1 wt%, such as 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 compositions of the present invention include additional components or ingredients, such as organic acids and / or polyols. The antimicrobial compositions of the present invention may include an organic acid 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 compositions of the present invention may include a polyol selected from the group consisting of glycerin, propanediol, 1,2-propanediol (propylene glycol), 1,3-butanediol, 1,4-butanediol, 2,3-butanediol, 1,2-pentanediol, sorbitol, sorbitan, isosorbide, and combinations thereof. The antimicrobial compositions of the present invention may include a polyol selected from the group consisting of a medium chain (C6-C8) polyol of the amino acid glycine. 10 ) fatty acid amides, such as capryloyl glycine or salts thereof.

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

[0108] These components may be considered optional. In some cases, this section may explicitly exclude one or more of the above-mentioned components from the disclosed compositions, for example, by claim language. For example, the claim language may be modified to state that the disclosed compositions, formulations, methods, etc. do not utilize or include one or more of the above-mentioned optional components.

[0109] The antimicrobial composition of the present invention can then be used in subsequent formulations, such as in the formulation of personal care products. The amount of the antimicrobial composition of the present invention can be present in the formulation in a range of, for example, about 0.25 wt% to about 5.0 wt%, such as 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%. In terms of upper limits, the amount of the antimicrobial composition of the present invention in the formulation can be less than 5.0 wt%, such as 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%. In terms of the lower limit, the amount of the antimicrobial composition of the invention in the formulation may be greater than 0.25 wt%, such as 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 invention has a pH value of about 9 or less. The pH value can range, for example, from about 3.5 to about 8.9, such as from 3.5 to about 7.9, from 4.0 to about 7.5, from about 4.5 to about 7.5, from about 5.0 to about 7.0 or from about 5.5 to about 6.5. In terms of the upper limit, the pH value can be less than 9, such as less than 8.9, less than 8.0, less than 7.5, less than 7.0 or less than 6.5. In terms of the lower limit, the pH value can be greater than 3.5, such as greater than 4.0, greater than 4.5, greater than 5.0 or greater than 5.5. These ranges and limits can also apply to formulations containing these compositions.

[0111] Compositions comprising alkylhydroxamic acid hydrogen potassium salt and mid-chain end diol may have a lower turbidity than 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 herein should be as low as possible. The turbidity of the antimicrobial compositions of the present invention may range, for example, from about 0 NTU to about 10 NTU, for example, from 0 NTU to 5 NTU, from 0 NTU to 2.5 NTU, from 0 NTU to 2 NTU, or from 0 NTU to 1 NTU. In terms of upper limits, 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 for 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 hydrogen potassium salts described herein contain potassium (in the form of potassium ions), for example, potassium is present at a concentration of greater than about 11 ppm. The concentration of potassium (K) can be, for example, present in the antimicrobial compositions of the present invention comprising alkylhydroxamic acid hydrogen potassium salts at a concentration ranging from about 11 ppm K to about 11000 ppm K, for example, 11 ppm to 10000 ppm, 50 ppm to 9000 ppm, or 100 ppm to 8000 ppm, or 200 ppm to 7000 ppm. In terms of the upper limit, the concentration can be less than 11000 ppm, for example less than 10000 ppm, less than 9000 ppm, less than 8000 ppm, or less than 7000 ppm. In terms of the lower limit, the concentration can be greater than 11 ppm, for example greater than 50 ppm, greater than 100 ppm, or greater than 200 ppm.

[0113] The antimicrobial composition as described above can be used in a formulation. The formulation containing the antimicrobial composition includes potassium, for example, potassium is present at a concentration of more than about 0.2 ppm. The concentration of potassium (K) can be, for example, present in the formulation (including the antimicrobial composition containing the potassium hydrogen alkyl hydroxamate salt) at a concentration ranging from 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. With respect to the upper limit, the concentration can 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. In terms of the lower limit, the concentration may be greater than 0.2 ppm, such as greater than 1.0 ppm, greater than 10 ppm, greater than 100 ppm or greater than 200 ppm.

[0114] Formulations containing potassium hydrogen alkyl hydroxamate salts and methods for preparing antimicrobial compositions The formulations and antimicrobial compositions described herein that include alkylhydroxamic acid hydrogen potassium salts are prepared by the method of preparing the formulation. In some embodiments, the method of preparing the formulation comprises the step of preparing a compound of formula (I): MH(AH)2(I) wherein M is an alkali metal cation consisting essentially of potassium; H is hydrogen, AH is C6~C 10 The method includes preparing an aqueous solution containing a compound of formula (I), which is an alkyl hydroxamic acid anion.

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

[0116] The method may include the case where the concentration of the compound according to formula (I) may vary depending on the end use of the final composition and / or formulation. The method may include the compound of formula (I) being present in the aqueous solution at a concentration of about 0.0002% to about 2.0%. For example, the compound of formula (I) may be present in the aqueous solution at a concentration ranging from about 0.0002% to about 2.0%, such as from about 0.0002% to about 1.5%, from about 0.0002% to about 1.0%, from about 0.0002% to about 0.5% or from about 0.0002% to about 0.1%. In terms of the upper limit, the concentration may be less than 2.0%, such as less than 1.5%, less than 1.0%, less than 0.5% or less than 0.2%. In terms of the lower limit, the concentration may be greater than 0.0002%, such as 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 bio-based.

[0117] The method includes combining at least one other component with a compound of formula (I) in an aqueous solution. The at least one other component is added in addition to (i) the water and (ii) the pH adjuster of the aqueous solution. The at least one other component can include a mid-chain end diol, a chelating agent, a polyol, or combinations thereof. The at least one other component for combination can additionally or alternatively include the following additional components or ingredients:

[0118] At least one other component of the method may include a mid-chain end diol, any of which are described above. In some embodiments, a mid-chain end diol is combined with the aqueous solution containing the compound of formula (I) in the method. In some embodiments, the mid-chain end diol is a glyceryl monoester, a glyceryl monoether, or a 1,2-alkanediol. The mid-chain end 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 end diol may be a glyceryl monoether selected from the group consisting of ethylhexylglycerin, methylheptylglycerin, caprylyl glyceryl ether, heptylglycerin, or cyclohexylglycerin. The mid-chain end 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] Chelating agents suitable for combination with the aqueous solution containing the compound of formula (I) in the method of the present invention include C6-C 10 These include, but are not limited to, alkylhydroxamic acid or its alkylhydroxamate salt, 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 salt of caprylhydroxamic acid, or a combination thereof. In some embodiments, the chelating agent consists essentially of caprylhydroxamic acid, a hydroxamate salt of caprylhydroxamic acid, or a combination thereof.

[0120] Polyols suitable for use with the methods 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, the at least one other ingredient for combination in the methods herein may additionally or alternatively include additional components or ingredients such as surfactants, emollients, humectants, conditioning agents, active agents, bleaching or whitening agents, fragrances, colorants, exfoliants, antioxidants, botanical ingredients, mica, smectites, thickeners, cannabinoids, oils, dyes, waxes, amino acids, nucleic acids, vitamins, hydrolyzed proteins and derivatives thereof, glycerin derivatives (e.g., glyceride esters), enzymes, anti-inflammatory and other agents, bactericides, antifungals, disinfectants, antioxidants, UV absorbers, dyes and pigments, preservatives, sunscreen actives, antiperspirant actives, oxidants, pH balancing agents, moisturizers, peptides and derivatives thereof, anti-aging actives, hair growth agents, anti-cellulite actives, and combinations thereof. These components may be considered optional in the methods herein.

[0122] The method includes adding a pH adjuster in an amount sufficient to provide a pH value of the formulation below about 8. The pH adjuster is added before, after, or in combination with at least one other ingredient.

[0123] In some embodiments, the pH adjuster is added prior to combining with at least one other ingredient, in other embodiments, the pH adjuster is added after combining with at least one other ingredient, and in still other embodiments, the pH adjuster is added simultaneously with combining with at least one other ingredient.

[0124] The pH adjuster according to the present 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, salts thereof, and combinations thereof. Preferred organic acids include citric acid, lactic acid, and malic acid.

[0125] In some embodiments, the method includes adding a sufficient amount of a pH adjusting agent 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. In terms of the upper limit, the pH value can be less than 8, e.g., less than 7.9, less than 7.5, less than 7.0, or less than 6.5. In terms of the lower limit, the pH value can 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 comprising the antimicrobial compositions of the present invention.

[0126] The method may include preparing a formulation comprising the antimicrobial composition. Depending on the end-use formulation, further additional ingredients, as described above, may be added. The formulation or composition may be a component of a personal care product, a home care product, a fabric care product, an institutional care product, a pharmaceutical product, an animal product, a food product, or an industrial product. Personal care products that can be made by the process herein include cosmetics, hair, nail, skin or fabric conditioners, shampoos, hair styling products, oils or waxes for grooming facial hair, permanent wave solutions, hair coloring agents, face or body washes, makeup remover products, cleansing lotions, emollient lotions or creams, bar soaps, liquid soaps, shaving creams, foams or gels, sunscreens, gels, lotions or creams for treating sunburn, deodorants or antiperspirants, moisturizing gels, shaving foams, face powders, foundations, lipsticks, blushes, eyeliners, wrinkle or anti-aging creams, eye shadows, eyebrow pencils, mascara, mouthwashes, toothpastes, oral care products, skin cleansing products, fabric cleaning products, dishwashing products, hair or fur cleaning products, and toners or moisturizers.

[0127] These detailed descriptions serve to illustrate the above general description and the embodiments which form a part of the present invention. These detailed descriptions are presented for purposes of illustration only and are not intended to limit the scope of the invention. EXAMPLES

[0128] Example 1: Alkali metal salts of caprylhydroxamic acid Potassium hydrogen caprylhydroxamate in Example 1 was prepared by 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 constant weight. Sodium caprylhydroxamate in Comparative Example 1 (sodium octanohydroxamate monohydrate, >98% as anhydrous) was purchased from TCI America and used as received.

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

[0130] TIFF2024531343000002.tif72170

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

[0132] TIFF2024531343000003.tif43170

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

[0134] Example 4: Micellar Water Formulations Containing Potassium Hydrogen Caprylhydroxamate Micellar water was prepared according to the formula in Table 3 using the following procedure: Water (95% of the total water required for the batch) was charged to an appropriately sized beaker of known tare weight equipped with an overhead mechanical stirrer and anchor-type blade. Mixing was started at 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 homogenous solution was formed. The pH of the formulation was recorded and then citric acid (10% in water) was added to adjust the pH to 6.5±0.2 and the amount of citric acid solution needed to adjust the pH was recorded. The remaining water was added appropriately to 100% and the batch was mixed until homogenous before being removed to a suitable container and stored. Comparative Example 2 was prepared following the same procedure except that potassium hydrogen caprylhydroxamate was substituted for sodium caprylhydroxamate (Comparative Example 1).

[0135] Prior to pH adjustment, the micellar water formulation prepared with NaCH exhibited significantly higher pH values ​​compared to the formulation prepared with KH(CH)2 (pH=10.34 vs. pH=9.55), and thus 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] TIFF2024531343000004.tif119170

[0137] Example 5: Natural Lotion Formulation Containing Potassium Hydrogen Caprylhydroxamate A lotion containing 100% bio-based ingredients was prepared according to the formula in Table 4 using the following procedure: A suitably sized beaker of known tare weight equipped with an overhead mechanical stirrer and anchor-type blade and hot plate for heating was charged with water (95% of the total water required for the batch), glycerin, methylheptylglycerin, and potassium hydrogen caprylhydroxamate (Example 1). Mixing was started at low to medium speed and the xanthan gum was slowly broken into the water phase and mixed until uniformly dispersed (no lumps remaining). The mixture was then heated to 80°C. In a separate beaker the oil phase ingredients were combined and heated to 80°C with low speed mixing and mixed until uniform. The oil phase mixture was added to the 80°C water phase mixture with medium to high speed mixing. After reaching a uniform appearance the mixture was cooled to approximately 75°C followed by homogenization at 3500 rpm for 3 minutes. After homogenization the mixture was cooled to approximately 45°C to 50°C with medium speed mixing. After cooling to 30°C, the pH of the formulation was recorded, followed by the addition of citric acid (10% in water) to adjust the pH to 6.5±0.2, recording the amount of citric acid solution required to adjust the pH. The remaining water was qs to 100% and the batch was mixed until uniform before being removed to a suitable container and stored. Comparative Example 2 was prepared following the same procedure, except that sodium caprylhydroxamate (Comparative Example 1) was replaced with potassium hydrogen caprylhydroxamate.

[0138] Prior to pH adjustment, the lotion formulation prepared with NaCH exhibited significantly higher pH values ​​compared to the formulation prepared with KH(CH)2 (pH=8.62 vs. pH=8.11), and thus 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] TIFF2024531343000005.tif166170

[0140] Example 6: Natural shampoo formulation containing potassium hydrogen caprylhydroxamate Example 6 was prepared according to the formula in Table 5. An appropriately sized beaker of known tare weight equipped with an overhead mechanical stirrer was charged with water (95% of the total water required for the batch), potassium hydrogen caprylhydroxamate (Example 1), lauryl glucoside, sodium cocoyl glutamate, cocamidopropyl betaine, and methylheptylglycerin. The batch was mixed at low to medium speed until the contents were uniform. The pH of the formulation was recorded, and then citric acid (10% in water) was added to adjust the pH to 6.5±0.2, and the amount of citric acid solution required to adjust the pH was recorded. The remaining water was added appropriately to 100%, and the batch was mixed until uniform, then removed 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] Prior to pH adjustment, the shampoo formulation prepared with NaCH exhibited significantly higher pH values ​​compared to the formulation prepared with KH(CH)2 (pH=11.46 vs. pH=10.71), and thus 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 ​​of Example 6 and Comparative Example 4 were 7.30 NTU and 7.83 NTU, respectively.

[0142] TIFF2024531343000006.tif129170

[0143] Example 7: Antimicrobial composition using potassium hydrogen caprylhydroxamate An antimicrobial composition consisting of caprylhydroxamic acid, 1,2-hexanediol, propanediol and potassium hydrogen caprylhydroxamate was prepared according to the formula in Table 6 and following the procedure below. 1,2-hexanediol and propanediol were charged to an appropriately sized beaker of known tare weight equipped with an overhead mechanical stirrer. The mixture was heated to 40°C-45°C with slow mixing to ensure adequate mixing without entraining air into the batch. Caprylhydroxamic acid and potassium hydrogen caprylhydroxamate were slowly sprinkled into the batch and mixed until completely dissolved. The batch was cooled and removed to a suitable container for storage. Comparative Example 5 was prepared similarly except that potassium hydrogen caprylhydroxamate was omitted from the batch.

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

[0145] TIFF2024531343000007.tif58170

[0146] Example 8: Microbiological challenge testing of micellar water formulations containing KH(CH)2 A micellar water formulation was prepared according to Example 8 in Table 7 using the following procedure: Deionized water was charged to an appropriate sized beaker equipped with an overhead mechanical stirrer and anchor type blade. Mixing was started at low to medium speed and the Polysorbate 20, Butylene Glycol and KH(CH)2 were added to the batch and mixed until a clear homogenous solution was formed. The pH was adjusted to 6.5±0.1 by adding Citric Acid (20% in water). The batch was mixed until homogenous and then removed and stored in an appropriate container.

[0147] TIFF2024531343000008.tif91170

[0148] Comparative Example 6 was prepared following the procedure used in Example 8, except that KH(CH)2 was omitted from the formulation.

[0149] A microbiological challenge test ("MCT") was conducted on the micellar water formulations of Example 8 and Comparative Example 6. The challenge test was conducted according to 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] TIFF2024531343000009.tif70170

[0151] TIFF2024531343000010.tif63170

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

[0153] Example 9: Micellar Water Formulations Containing KH(CH)2 Antimicrobial Blend Example 9 was prepared according to the procedure used for Example 8, except that methylheptylglycerin (MHG) was added according to the formula as in Table 7. Example 9 has the same formula as that of Example 4 used above.

[0154] Challenge tests were conducted according to USP and PCPC official test methods to determine the preservative efficacy of Example 9. The results are shown in Table 8C.

[0155] TIFF2024531343000011.tif67170

[0156] Example 9, containing KH(CH)2 and MHG, demonstrated outstanding preservative efficacy, meeting and exceeding the USP, PCPC, EP-A and EP-B acceptance criteria against all organisms, while Comparative Example 6 demonstrated very poor 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 formula in Table 10 using the following procedure: Water and glycerin were added to an appropriate sized beaker equipped with an overhead mechanical stirrer and anchor-type blade and hot plate for heating. Mixing was started at low to medium speed and the xanthan gum was slowly sprinkled into the water phase and mixed until uniformly dispersed (no lumps remaining). Methylheptylglycerin (MHG) and KH(CH)2 were added. The mixture was then heated to 80°C. In a separate beaker, the oil phase ingredients were combined and heated to 80°C with low speed mixing and mixed until uniform. The oil phase mixture was added to the water phase mixture at 80°C with medium to high speed mixing. After reaching a uniform appearance, the mixture was cooled to approximately 75°C and subsequently homogenized at 5000 rpm for 3 minutes. The mixture was cooled to approximately 25°C with medium speed stirring. The batch pH was adjusted to 6.6±0.1 using citric acid (20% in water). The composition was mixed until uniform and then removed and stored in a suitable container.The formulation of Example 10 corresponds to that of Example 5 above.

[0158] TIFF2024531343000012.tif143170

[0159] Comparative Example 7: Natural lotion formulation without 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 omitted from the formulation. The formulation of Comparative Example 7 corresponds to that of Comparative Example 3 above.

[0160] A microbiological challenge test (MCT) in accordance with the United States Pharmacopoeia (USP) and PCPC official test methods was conducted 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 formulation ("Personal Care Products Council Technical Guidelines. Microbiology Guidelines," (2018) Personal Care Products Council, Washington, DC 7 (See, e.g., and the references cited therein.) The results shown in Tables 10A and 10B show the logarithm of the viable counts measured at the end of the period. The row entitled "Inoculation Level" shows the initial number of organisms present at the start of the test.

[0161] Comparative Example 7, which does not contain KH(CH)2 and MHG, fails to meet the PCPC acceptance criteria of 99% reduction of bacteria and 90% reduction of 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. Example 10 was also observed to meet the European Pharmacopeia (EP) "B" criteria (EP-B) for control of bacteria, yeast and mold, i.e., 99.9% reduction (3 log reduction) of bacteria in 14 days and 90% reduction (1 log reduction) of yeast and mold in 14 days (European Pharmacopeia (Ph. Eur.) 10.0, 2021, Section 5.1.3, Efficacy of Antimicrobial Preservation 6 (See ).

[0162] TIFF2024531343000013.tif67170

[0163] TIFF2024531343000014.tif67170

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

[0165] It should be further understood that all values ​​are approximate and are provided for illustrative purposes. All references cited and discussed herein are incorporated by reference in their entirety to the same extent as if each reference was individually incorporated by reference.

[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. Formula (I): MH(AH) ２ (I) wherein M is potassium; H is hydrogen, AH is C ６ ~C １０ an alkylhydroxamic acid anion; an organic acid in an amount sufficient to provide a pH value of the formulation of 8 or less; 1. An aqueous formulation comprising:

2. A diol having a C4 to C10 chain length and a medium chain end diol, Formula (I): MH(AH) ２ (I) wherein M is potassium; H is hydrogen, AH is C ６ ~C １０ an alkylhydroxamic acid anion; C ６ ~C １０ an alkylhydroxamic acid, 1. An antimicrobial composition comprising:

3. AH is caprylhydroxamate and MH(AH) ２ 2. The formulation of claim 1, wherein is potassium hydrogen caprylhydroxamate.

4. 2. The formulation of 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. 10. The formulation of 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 wherein the formulation has a pH value of 3.5 to 7.9, or 4.0 to 7.5, or 4.5 to 7.5, or wherein 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 wherein 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. 0.01 wt% to 10 wt% of the compound of formula (I); 10 wt % to 80 wt % of the mid-chain end diol; 1 wt% to 20 wt% of said C ６ ~C １０ an alkylhydroxamic acid, 3. The composition of claim 2, wherein the composition comprises 11 ppm to 11,000 ppm of potassium.

7. The mid-chain terminal diol is a glyceryl monoester selected from the group consisting of glyceryl monocaprate, glyceryl monopelargonate, glyceryl monocaprylate, and glyceryl monoheptanoate; a glyceryl monoether selected from the group consisting of ethylhexylglycerin, methylheptylglycerin, caprylyl glyceryl ether, heptylglycerin, and cyclohexylglycerin; 1,2-alkanediols 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 of claim 2, wherein the composition is at least one of:

8. further comprising a polyol 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 a surfactant, emollient, humectant, conditioning agent, active agent, bleaching or whitening agent, fragrance, colorant, exfoliant, antioxidant, botanical, mica, smectite, thickener, cannabinoid, 3. The composition of claim 2, further comprising at least one additional ingredient selected from oils, dyes, waxes, amino acids, nucleic acids, vitamins, hydrolyzed proteins and derivatives thereof, glycerin derivatives, glyceride esters, enzymes, anti-inflammatory agents, bactericides, antifungals, disinfectants, antioxidants, UV absorbers, dyes and pigments, antimicrobial agents, sunscreen actives, antiperspirant actives, oxidizing agents, pH balancing agents, moisturizers, peptides and derivatives thereof, anti-aging actives, hair growth agents, anti-cellulite actives, and combinations thereof.

9. 3. The composition of 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. 3. A formulation comprising the composition of claim 2, wherein the composition is present in the formulation in a range of 0.25 wt% to 5.0 wt%, or 0.50 wt% to 2.5 wt%.

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

12. 11. The formulation of claim 1 or 10, which is or is a component of a personal care product, a home care product, a fabric care product, an institutional care product, a pharmaceutical product, an animal product, a food product, or an industrial product.

13. 11. The formulation of claim 1 or 10, which is, or is a component of, a personal care product selected from the group consisting of cosmetics, hair conditioners, nail conditioners, skin or fabric conditioners, shampoos, hair styling products, oils or waxes for grooming facial hair, permanent wave solutions, hair colorants, face or body washes, makeup remover products, cleansing lotions, emollient lotions or creams, bar soaps, liquid soaps, shaving creams, foams or gels, sunscreens, gels, lotions or creams for treating sunburn, deodorants or antiperspirants, moisturizing gels, shaving foams, face powders, foundations, lipsticks, blushers, eyeliners, wrinkle or anti-aging creams, eye shadows, eyebrow pencils, mascara, mouthwashes, toothpastes, oral care products, skin cleansing products, fabric cleaning products, dishwashing products, hair or fur cleaning products, and toners or moisturizers.

14. Formula (I): MH(AH) ２ (I) wherein M is potassium; H is hydrogen, AH is C ６ ~C １０ preparing an aqueous solution containing a compound of formula (I), combining the aqueous solution with at least one other ingredient; adding a pH adjuster in an amount sufficient to provide a pH value of the formulation of 8 or less; wherein the pH adjuster is added before, after, or in combination with the at least one other ingredient; A method for preparing a formulation comprising:

15. 15. The formulation of claim 1 or the composition of claim 2 or the method of claim 14, wherein substantially all of the carbon present in the compound of formula (I) is bio-based.

16. The method of claim 14, wherein the at least one other ingredient comprises a mid-chain end diol, a C6-C10 alkyl hydroxamic acid, a polyol, a surfactant, an emollient, a humectant, a conditioning agent, an active agent, a bleaching or whitening agent, a fragrance, a colorant, an exfoliant, an antioxidant, a botanical, mica, smectite, a thickener, a cannabinoid, an oil, a dye, a wax, an amino acid, a nucleic acid, a vitamin, a hydrolyzed protein and its derivatives, a glycerin derivative, a glyceride ester, an enzyme, an anti-inflammatory agent, a bactericide, an antifungal agent, a disinfectant, an antioxidant, a UV absorber, a pigment, an antimicrobial agent, a sunscreen active, an antiperspirant active, an oxidizer, a pH balancer, a moisturizer, a peptide and its derivatives, an anti-aging active, a hair growth agent, an anti-cellulite active, and combinations thereof.

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

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

19. The formulation of claim 1, wherein the formulation does not contain a free hydroxylamine concentration.

Images