Cationic compositions based on self-neutralizing amino acids

Abstract

The invention described herein includes a self-neutralizing amino acid-based cationic composition comprising an amino acid-based cationic ester, a nonionic amphiphilic molecule, and an anhydrous buffer. In an embodiment, when the composition is dispersed or dissolved in an aqueous solvent, the composition provides a final output solution / dispersion having a pH value greater than about 4. The amino acid-based cationic ester can be a reaction product of (i) an amino acid having a non-polar side chain and an amino group that has been neutralized by an acid; and (ii) a long-chain fatty alcohol. Also included within the scope of the present invention is a method for preparing a self-neutralizing amino acid-based cationic composition, which comprises combining an amino acid-based cationic ester, a nonionic amphiphilic molecule, and an anhydrous buffer. The final output composition is in the form of an anhydrous solid. The present invention also discloses formulations containing the amino acid-based cationic ester and / or compositions containing the amino acid-based cationic ester.

Description

[0001] Cross-reference

[0002] This application claims the benefit of U.S. Provisional Patent Application No. 62 / 815,314, filed on March 7, 2019, entitled “Self-Neutralizing Amino Acid-Based Cationic Compositions,” under 35 U.S.C. §119(e), the entire contents of which are incorporated herein by reference. Background Art

[0003] Neutralized amino acid esters of non-petrochemically derived cationic emulsifiers are described and claimed in Burgo's U.S. Pat. No. 8,105,569 and related applications. Burgo's amino acid-based cationic esters (hereinafter referred to as "AABC"s) can be provided in anhydrous form, that is, a form that does not contain any substantial amount of water, e.g., less than about 5% water by weight.

[0004] Burgo's AABC composition consists primarily of amino acid esters, wherein the amino groups are neutralized by a strong organic acid, such as ethanesulfonic acid (ESA), which renders the amino acid esters cationic species. The AABC composition may also contain a small amount, such as less than 2 weight percent (wt%), of unreacted amino acids, such as isoleucine or valine, which are also neutralized by a strong organic acid to produce strong acid salts, such as isoleucine ethanesulfonate or valine ethanesulfonate.

[0005] When Burgo's AABC compositions are dissolved or dispersed in an aqueous medium, they tend to produce aqueous compositions having relatively low pH values ​​(e.g., pH < 3.0). Without being limited by theory, it is believed that these low pH values ​​are due to the fact that the AABCs are salts of strong acids and weak bases. The anions (i.e., the conjugate bases of the strong acids) become spectator ions and are unable to attract protons, while the cations of the weak bases donate protons to the water, forming hydronium ions (H 3 O + ), thereby lowering the pH of the solution. In addition, strongly acidic amino acid salts, such as isoleucine ethanesulfonate or valine ethanesulfonate, are present as unreacted byproducts in the AABC composition, which will also contribute to lowering the pH of the solution.

[0006] Such low pH values ​​are undesirable in many applications, particularly in personal care and cosmetics, where most products are formulated at a pH of 4.0 or greater. Previously, formulations prepared using AABC required careful and time-consuming adjustment of the pH using a suitable base in order to achieve a stable pH within the desired range. For example, the skin pH range reported in the literature is pH 4.5-pH 5.0, which is generally the desired pH associated with personal care products intended for topical use on the skin. See, for example, JW Weichers, Formulating at pH 4-5: How to Lower the pH to Benefit Skin and Formulation, Cosmetics & Toiletries, 2008, 123(12), 61-70.

[0007] There remains a need in the art for an amino acid based cationic ester which, when included in a formulation, provides a final output solution / dispersion having a pH suitable for personal care and cosmetic products. Summary of the invention

[0008] The invention described herein includes a self-neutralizing amino acid based cationic composition comprising an amino acid based cationic ester, a nonionic amphiphilic molecule and an anhydrous buffer. In one embodiment, when the composition is dispersed or dissolved in an aqueous solvent, the composition provides a final output solution / dispersion having a pH greater than about 4.

[0009] The amino acid-based cationic ester may be a reaction product of (i) an amino acid having a non-polar side chain and an amino group neutralized with an acid; and (ii) a long-chain fatty alcohol.

[0010] The present invention also includes a method for preparing a self-neutralizing amino acid-based cationic composition, which comprises combining an amino acid-based cationic ester, a nonionic amphiphilic molecule and an anhydrous buffer. The resulting composition is in the form of an anhydrous solid.

[0011] The present invention also discloses a formulation containing the amino acid-based cationic ester and / or a composition comprising the amino acid-based cationic ester. BRIEF DESCRIPTION OF THE DRAWINGS

[0012] The foregoing summary, as well as the following detailed description of preferred embodiments of the invention, will be better understood when read in conjunction with the appended drawings.

[0013] The present invention is not limited to the specific arrangements and means shown. In the drawings:

[0014] Figure 1 pH of aqueous compositions shown as a function of wt % AABC blend in the compositions of Examples 4 to 6 and Comparative Examples 4 to 6;

[0015] Figure 2 is a polarized light micrograph (400x magnification) of a typical formulation of the present invention comprising 15% of a self-neutralizing AABC composition prepared according to the present invention;

[0016] Figure 3 SAXS data showing a lamellar liquid crystal system comprising brassinoyl valine ethanesulfonate; and

[0017] Figure 4 SAXS data for a lamellar liquid crystal system containing brassinolide ethanesulfonate are shown. DETAILED DESCRIPTION

[0018] Detailed description of the invention

[0019] The present invention provides a self-neutralizing amino acid-based cationic composition that can be dissolved or dispersed in water to provide an aqueous composition having an ideal pH value (about 3.5 to about 7) without the need to adjust the pH value by adding a base. The present invention also provides a method for preparing the self-neutralizing amino acid-based cationic composition and a method for preparing a composition containing the self-neutralizing amino acid-based cationic composition.

[0020] The self-neutralizing amino acid-based cationic composition described herein includes an amino acid-based cationic ester (i.e., a neutralized amino acid ester), a nonionic amphiphilic molecule, and an anhydrous buffering agent (hereinafter referred to as "ABA"). Each component can exist independently in the composition in a single form (e.g., an amino acid-based cation) or as a mixture (e.g., a mixture of two or more amino acid-based cationic esters). Detailed information on the individual components of the composition is provided below. When dispersed or dissolved in an aqueous solvent such as water, the resulting solution / dispersion has a pH greater than about 3.5, about 3.5 to about 7, about 4 to about 6.5, about 4 to about 5.5, or about 4 to about 5.

[0021] With respect to the use of the self-neutralizing AABC compositions described herein, neutralized amino acid esters (i.e., amino acid-based cationic esters) described in Burgo (hereinafter referred to as "AABC") may be used. The contents of Burgo are incorporated herein by reference and are provided in Appendix A for convenience. Generally, such AABCs may be prepared by esterification of (i) an amino acid having a non-polar side chain, wherein the amino group of the amino acid has been neutralized with an acid; and (ii) a long chain fatty alcohol. AABC may be represented by the structure of formula (I):

[0022]

[0023] In the molecular formula (I), R 1 R represents an alkyl group which may be branched or straight chain. It may have one to ten carbon atoms or two to six carbon atoms. 2 R represents a carbon chain, which may be straight or branched. It may contain ten to fifty carbon atoms or twenty-four to thirty-two carbon atoms. 2 The chain may contain at least one unsaturated carbon atom. 2 is an alkyl group having eight to twenty-four carbon atoms. - represents the conjugate base of the acid used to neutralize the amino acid ester.

[0024] The amino acids forming the AABC include any neutral amino acids. In one embodiment, L-alanine, L-valine, L-leucine and L-isoleucine can be selected. In some embodiments of the present invention, L-isoleucine and L-valine are particularly preferred. Other options can include any α, ω-aminoalkyl carboxylic acid, such as 11-aminoundecanoic acid or 12-aminododecanoic acid.

[0025] To obtain the esters of the present invention, the amino group of the amino acid is neutralized with an acid and reacted with a long chain fatty alcohol. Suitable fatty alcohols may be straight chain and / or branched and may additionally be saturated and / or unsaturated. Most preferably, the fatty alcohol contains from about 10 carbon atoms to 50 carbon atoms or from about 24 carbon atoms to about 32 carbon atoms. In one embodiment, straight chain and / or branched fatty alcohols containing from about 12 carbon atoms to about 22 carbon atoms may be preferred. In another embodiment, straight chain fatty alcohols containing from about 16 carbon atoms to about 24 carbon atoms are preferred.

[0026] Examples of suitable fatty alcohols include lauryl alcohol, myristyl alcohol, palmityl alcohol, stearyl alcohol, oleyl alcohol, isostearyl alcohol, arachidyl alcohol, behenyl alcohol and mixtures or combinations thereof. It is recommended that the fatty alcohol is from a non-petrochemical source. In one embodiment, the AABC is the reaction product of the amino acid and the fatty alcohol, wherein the amino acid is L-alanine, L-valine, L-leucine, L-isoleucine and / or mixtures of the same, and the fatty acid is coconut oil (including a mixture of various long chain fatty acids), stearyl alcohol, isostearyl alcohol and / or brassicyl alcohol (optionally hydrogenated). Brassica alcohol as used herein is defined as a fatty alcohol made from seed oil, the seed oil being derived from a plant containing or consisting essentially of C 18 , C 20 and C 22 Fatty alcohols from the cruciferous family.

[0027] In some embodiments, AABC is most preferably a fatty alcohol ester whose amino acid is L-valine or L-isoleucine, neutralized with ethanesulfonic acid and preferably solid at 25°C. Such AABCs can include, for example, brassicyl valinate esylate, cetyl valinate esylate, cetearyl valinate esylate, stearyl valinate esylate, isostearyl valinate esylate, behenyl valinate esylate, octyldodecyl valinate esylate, decyltetradecyl valinate esylate; brassicylisoleucinate esylate, cetyl isoleucinate esylate, Preferably, the esylate is selected from the group consisting of cetearyl isoleucinate esylate, stearyl isoleucinate esylate, isostearyl isoleucinate esylate, behenyl isoleucinate esylate, octyldodecyl isoleucinate esylate, decyltetradecyl isoleucinate esylate; most preferably, brassicyl valinate esylate and / or brassicylisoleucinate esylate.

[0028] AABC can be synthesized by any method known or developed in the art. However, an exemplary embodiment of the synthesis is provided in Burgo, which is incorporated herein by reference.

[0029] The composition also includes at least one nonionic amphiphile; the selected nonionic amphiphile is most preferably a nonionic amphiphile that is solid at 25°C. In some embodiments, it can contain from about 10 carbon atoms to about 35 carbon atoms, from about 15 carbon atoms to about 30 carbon atoms, and from about 16 carbon atoms to about 24 carbon atoms. Typical nonionic amphiphiles can contain:

[0030] Fatty alcohols, such as, for example, straight or branched chain fatty alcohols containing 12 or more carbon atoms, such as lauryl, myristyl, cetyl, cetearyl, stearyl, isostearyl, oleyl, arachidyl, behenyl alcohol, octyldodecanol, decyltetradecyl alcohol, coconut alcohol, palmitoleyl alcohol, palm kernelol, brassic alcohol, hydrogenated rapeseed alcohol; preferably straight chain fatty alcohols containing 16 or more carbon atoms; most preferably brassic, cetyl, cetearyl, stearyl or behenyl alcohol;

[0031] Fatty glyceryl esters, such as, for example, mono-, di- or triesters of glycerol or mixtures thereof, comprising esters of glycerol and one or more fatty acids containing 12 or more carbon atoms, such as, for example, glyceryl laurate, glyceryl myristate, glyceryl palmitoleate, glyceryl sesquistearate, glyceryl stearate, glyceryl stearate se, glyceryl behenate, glyceryl distearate, brassica glycerides, hydrogenated rapeseed glycerides, hydrogenated coconut glycerides, hydrogenated C 12-18 Glycerides, hydrogenated palm oil glycerides, hydrogenated soybean glycerides; preferably canola glycerides;

[0032] Fatty glycol esters, such as, for example, monoesters or diesters of ethylene glycol or mixtures thereof; esters of ethylene glycol and one or more fatty acids containing 12 or more carbon atoms, such as, for example, ethylene glycol stearate, ethylene glycol distearate, butylene glycol behenate, ethylene glycol dibehenate;

[0033] Fatty esters of polyglycerol, such as, for example, polyglycerol esters are monoacyl esters or polyacyl esters of polyglycerol (e.g., each polyglycerol chain carries an average of 1.5 to 10 ester groups), wherein the polyglycerol has an average degree of polymerization of 2 to 10 glyceryl repeating units and has an acyl group of about 12 carbon atoms to about 24 carbon atoms, wherein the acyl group can include lauroyl, cocoyl, myristoyl, palmitoyl, stearoyl, arachidonic acid, behenyl and brassicyl, such as, for example, polyglyceryl-3 stearate, polyglyceryl-3 stearate SE, polyglyceryl-4 stearate, polyglyceryl-10 stearate, polyglyceryl-6 sesquistearate, polyglyceryl-4 pentastearate, polyglyceryl-6 pentastearate, polyglyceryl-10 pentastearate, polyglyceryl-3 behenyl esters, polyglyceryl-5 tribehenate, polyglyceryl-6 tetrabehenate, polyglyceryl-2 distearate, polyglyceryl-3 distearate, polyglyceryl-6 distearate, polyglyceryl-10 distearate, polyglyceryl-2 palmitate, polyglyceryl-3 palmitate, polyglyceryl-4 palmitate, polyglyceryl-6 palmitate, polyglyceryl-6 dipalmitate, polyglyceryl-4 laurate, polyglyceryl-5 laurate, polyglyceryl-6 laurate, polyglyceryl-7 laurate, polyglyceryl-8 laurate, polyglyceryl-10 laurate, polyglyceryl-2 myristate, polyglyceryl-3 myristate, polyglyceryl-4 myristate, polyglyceryl-5 myristate, polyglyceryl-6 myristate, polyglyceryl-10 myristate, and polyglyceryl-5 pentamyristate;

[0034] Fatty esters of methyl glucose, such as, for example, methyl glucose esters such as mono- or polyacyl esters of methyl glucose (e.g., with an average of 1.5 to 3 ester groups per methyl glucose unit), when in the case of an acyl group of about 12 to about 24 carbon atoms, wherein the acyl group may comprise lauroyl, cocoyl, myristoyl, palmitoyl, stearoyl, arachidonyl, behenyl and brassicyl, such as, for example, methyl glucose dioleate, methyl glucose isostearate, methyl glucose laurate, methyl glucose sesquicaprylate / sesquicaprate, methyl glucose sesquicocoate, methyl glucose sesquiisostearate, methyl glucose sesquilaurate, methyl glucose sesquioleate and methyl glucose sesquistearate;

[0035] Fatty esters of sorbitan, such as, for example, monoacyl or polyacyl esters of sorbitan (e.g., with an average of 1.5 to 4 ester groups per methyl glucose unit) and having an acyl group of about 12 to about 24 carbon atoms, such as lauroyl, cocoyl, myristoyl, palmitoyl, stearoyl, arachidonyl, behenyl and brassicyl. Examples include sorbitan cocoate, sorbitan dioleate, sorbitan distearate, sorbitan laurate, sorbitan oleate, sorbitan olivate, sorbitan palmitate, sorbitan palmitoleate, sorbitan sesquioleate, sorbitan sesquistearate, sorbitan stearate, sorbitan trioleate and sorbitan tristearate.

[0036] The composition further comprises an anhydrous buffer ("ABA"). By describing a material herein, such as a buffer, "anhydrous" means that the material is substantially free of added water, preferably contains less than about 5% water, more preferably contains less than about 4% water, even more preferably contains less than about 2% water, and most preferably contains less than about 1.5% water. Anhydrous materials may contain small amounts of incidental water, e.g., absorbed from ambient humidity or processing conditions, e.g., from incomplete drying after washing. In some embodiments, the ABA is preferably in particulate or powder form, e.g., it is a finely divided solid having a small particle size, preferably less than about 100 μm (micrometers).

[0037] ABA suitable for use in the composition of the present invention includes any known or under development in the art or the same combination. In various embodiments, when the AABC composition is dissolved in water, the ABA is a material capable of maintaining the pH of the aqueous solution.

[0038] If in powder form, ABA can be a free-flowing solid having an average particle size of less than about 100 μm, preferably less than about 75 μm, more preferably less than about 50 μm, even more preferably less than about 25 μm, and in certain embodiments, the average particle size will be less than about 20 μm. In many embodiments, the small particle size powder form can be used to facilitate the maintenance of a uniform dispersion of ABA throughout the composition during processing in the molten state and during the cooling and solidification process to produce a solid form having the buffer uniformly dispersed throughout.

[0039] In various embodiments, the selected ABA can be a salt of a strong base or a weak organic acid, for example, the strong base is sodium hydroxide, potassium hydroxide, calcium hydroxide, etc., and the weak organic acid is gluconic acid, citric acid, lactic acid, etc.

[0040] Typical ABAs for use in the compositions of the present invention include, for example, alkali metal or alkaline earth metal salts of gluconic acid, such as sodium gluconate, calcium gluconate.

[0041] As prepared, the composition of the present invention may contain any relative amount of any of the two / three above-mentioned components; such relative amounts may vary depending on several factors, such as manufacturing parameters, the intended end use of the composition, and the like as understood in the art. Therefore, variations in relative amounts are a routine matter for those skilled in the art.

[0042] However, for purposes of illustrating the present invention, it is suggested that AABC is present in the composition in an amount of about 10 wt % to about 70 wt %, about 12 wt % to about 60 wt %, about 15 wt % to about 55 wt %, or about 20 wt % to about 50 wt %, each with respect to the weight of the total composition.

[0043] In some embodiments, ABA can be included in the composition in an amount of about 2 wt % to about 25 wt %, about 4 wt % to about 20 wt %, about 6 wt % to about 15 wt %, or about 8 wt % to about 12 wt %, each with respect to the weight of the total composition.

[0044] In many embodiments, the balance of the composition can be made up of the selected nonionic amphiphilic molecule. If other ingredients are included in the composition of the present invention, the selected nonionic amphiphilic molecule can be present in an amount of at least about 10 wt%, about 15 wt% to about 70 wt%, and in some embodiments, preferably about 20 wt% to about 40 wt%, each with respect to the total composition.

[0045] In various embodiments, regardless of the amount of nonionic amphiphilic molecules present, the ratio of amino acid-based cationic ester to anhydrous buffer in the composition can be: (i) by weight (wt%:wt%): about 1:2 to about 1:8, about 1:2 to about 1:6, about 1:2 to about 1:4, or about 1:2 to about 1:3; or, (ii) by mole: about 1:1 to about 1:5, about 1:1 to about 1:4, about 1:1 to about 1:3, or about 1:1 to about 1:2. In some embodiments, the molar ratio of amino acid-based cationic ester to anhydrous buffer can be 1:1 or 1:2.

[0046] In many embodiments, the composition is in an anhydrous form, preferably in an anhydrous solid form.

[0047] The self-neutralizing AABC composition can include other ingredients. Such ingredients are preferably present in a powder form and / or are also anhydrous. Examples include water-soluble polymers or water-soluble resins, such as guar hydroxypropyl ammonium chloride, hydroxypropyl guar gum, polyquaternium-10, hydroxyethylcellulose, hydroxypropyl methylcellulose, starch, guar gum, and cassia gum; chelating agents, such as tetrasodium EDTA, disodium EDTA, and tetrasodium glutamate diacetate; and zwitterionic surfactants, such as cocamidopropyl betaine, cocamidopropyl hydroxysultaine, and lauramidopropyl betaine.

[0048] The self-neutralizing AABC composition also includes other solid or semi-solid ingredients that can be incorporated into the composition within the molten phase, such as, for example, plant-derived triglycerides, i.e., oils and butters, and waxes and wax esters, preferably non-petrochemically derived. Other therapeutic or cosmetic benefit agents, including antioxidants, such as, tocopheryl acetate or ascorbyl palmitate, may also be added to the self-neutralizing AABC composition.

[0049] The self-neutralizing AABC compositions of the present invention may be prepared by any process known or developed in the art. However, for illustrative purposes, the general manufacturing process is as follows: The AABC and nonionic amphiphilic molecules are heated until completely melted and mixed to form a homogeneous molten mixture. An anhydrous buffer is dispersed in the molten mixture to produce a uniform dispersion of powder in the molten mixture, preferably under shear. This dispersion is maintained under heat and shear during processing to ensure that it remains homogeneous in the molten state.

[0050] In one embodiment, care should be taken to ensure that the ABA does not precipitate out, e.g., by precipitation, during processing. A homogeneous mixture can be maintained by applying constant shear, e.g., with a mechanical mixer. In a larger vessel, recirculation of the contents by pumping and in-line shear mixing can be combined with mechanical agitation to maintain a homogenous dispersion of ABA in the molten mixture.

[0051] The molten mixture is then cooled. If desired, a solid may be obtained to increase the ease of subsequent post-manufacturing handling and processing. In some embodiments, the composition may be subjected to various post-manufacturing processes, such as, for example, tableting, tableting, granulation, beading, extrusion, and spheronization, etc. For example, the mixture may be spread into a thin layer on a frozen surface and then cooled and solidified; the resulting solid sheet may be broken into small pieces (flakes) and stored for subsequent mixing into the formulation. The cooling and solidification process is preferably configured to ensure a uniform and homogeneous distribution of the buffer in solid form, for example, from flake to flake or tablet to tablet, from the beginning of the run to the end of the run when performed on a large-scale continuously running equipment; therefore, cooling and solidification must occur on a time scale that is much faster than the sedimentation rate (i.e., sedimentation velocity) of the ABA particles in the molten mixture.

[0052] The compositions of the present invention can be incorporated into a variety of consumer and industrial end-use formulations, such as those used in personal care, home and institutional care, pharmaceuticals, veterinary care, oral care, textile care, metalworking, food processing and industrial applications.

[0053] In one embodiment of the present invention, the composition is incorporated with at least one other ingredient to form a formulation, such as a personal care formulation. Suitable additive ingredients include water, surfactants, emollients, moisturizers, conditioners for hair, skin or nails, chelating agents, active agents, bleaching or whitening agents, additional pH adjusters, fragrances, colorants, exfoliants, antioxidants, botanical ingredients such as plant extracts, mica, montmorillonite, thickeners, drugs, cannabinoids, oils, dyes, waxes, amino acids, nucleic acids, vitamins, hydrolyzed proteins and their derivatives, glycerol and its derivatives, enzymes, anti-inflammatory drugs and other drugs, microbicides, antifungals, antibacterial agents, antioxidants, UV absorbers, dyes and pigments, preservatives, sunscreen actives, sweat blockers, oxidants, pH balancers, monoglycerides, moisturizing agents, peptides and their derivatives, anti-aging actives, hair growth promoters, anti-cellulite actives, etc. can be used in formulations for human use.

[0054] Such formulations can have end uses such as, but not limited to, hair, nail, skin or textile treatments, shampoos, hair gels, beard / moustache oils or waxes, hair styling formulations, perming solutions, hair dyes, glazes, lotions, face and body washes, makeup removers, face makeup removers, skin lotions / creams, bar soaps, shaving creams, sunscreens, sunburn treatments, deodorants, moisturizing gels, moisturizing serums, UV protection serums, shaving foams, face powders, foundations, lipsticks, blushes, eyeliners, anti-wrinkle and anti-aging creams, eye shadows, eyebrow pencils, mascara, mouthwashes, toothpastes, oral care compositions, skin cleaning compositions, textile cleaning compositions, dish cleaning compositions, hair or fur cleaning compositions, deodorants or antiperspirants, make-up, hair styling compositions, skin moisturizers, lotions, hair conditioners, and nail conditioners.

[0055] These formulations of the present invention, including self-neutralizing AABC compositions, can be prepared by any processing method known or developed in the art. However, for illustrative purposes, the general process is as follows: An aqueous phase is heated to a temperature above the melting temperature of the self-neutralizing AABC composition and maintained under shear (mixing). While mixing, the solid self-neutralizing AABC composition is slowly added and dispersed and dissolved in the aqueous phase. The formulation is mixed until the buffering agent of the AABC is dissolved and a stable, uniform pH is obtained throughout the final output composition. Other ingredients can be added before or after the addition of the self-neutralizing AABC composition as appropriate.

[0056] Alternatively, the process is as follows: the self-neutralizing AABC composition is heated to form a liquid; the liquid is maintained under shear (mixing) to ensure uniform distribution of the buffer. An aqueous phase is heated to approximately the same temperature as the molten self-neutralizing AABC composition. The molten self-neutralizing AABC composition is combined with the heated aqueous phase while heating and mixing; appropriate agitation is used to ensure uniform mixing of the two phases. The formulation is mixed until the buffer of the AABC is dissolved and a stable, uniform pH is achieved throughout the final resulting composition. In this process, other ingredients may be added to the aqueous phase or the molten self-neutralizing AABC phase, as appropriate, before the two phases are combined, or added to the final resulting composition after the two phases are combined.

[0057] For example, fatty alcohols, fatty acids, triglycerides, waxes, cosmetic oils, and the like can be mixed with the melt prior to combining with the aqueous phase. Alternatively, water soluble ingredients, such as humectants, chelating agents, viscosity increasing agents such as water soluble polymers, and the like can be added to the aqueous phase prior to combining with the melt self-neutralizing AABC.

[0058] In many embodiments, aqueous formulations prepared using the self-neutralizing AABC compositions of the present invention will exhibit lamellar liquid crystal phase behavior. Such liquid crystal phase behavior can be readily characterized using techniques familiar to those skilled in the art, such as polarizing microscopy, small angle X-ray scattering (SAXS), and cryo-fracture scanning electron microscopy (cryo-SEM). Lamellar liquid crystal systems can be characterized by the spacing of the lamellar bilayer plates, referred to as the lattice spacing (D-spacing). The lamellar liquid crystal phase formed by the compositions of the present invention can have a lattice spacing of about 1 nm (nanometer) to about 100 nm as measured by SAXS, and in certain embodiments, have a lattice spacing of about 2 nm to about 25 nm, with preferred embodiments having a lattice spacing of about 3 nm to about 15 nm.

[0059] Those skilled in the art will recognize that the lattice spacing of the lamellar liquid crystal phase can be adjusted by changing one or more variables, including the carbon chain length of the AABCs and / or nonionic amphiphiles in the self-neutralizing AABC composition, the levels of AABC and nonionic amphiphiles in the formulation, or the ratio of AABC to nonionic amphiphiles in the self-neutralizing AABC composition or in the formulation itself, for example, additional AABC or nonionic amphiphiles can be added to the formulation containing the self-neutralizing AABC composition to affect the lattice spacing of the lamellar liquid crystal phase. The pH, ionic strength or level of dispersed oil phase in the formulation can also be changed to affect the lamellar lattice spacing. The lamellar liquid crystal phase of the present invention preferably has a lattice spacing that remains constant over a temperature range of 20-60°C.

[0060] In another exemplary embodiment of a method for preparing a solid formulation containing the self-neutralizing composition of the present invention, the self-neutralizing AABC is heated to a molten state and mixed with appropriate agitation to maintain a uniform distribution of the buffer in the mixture. Additional ingredients are added and mixed into the molten mixture. The mixture is cooled to produce a solid formulation that exhibits a preselected pH value when used by the end consumer.

[0061] For example, a 10% solution of the solid formulation preferably has a pH of about 3.5 to about 6.5, more preferably about 3.7 to about 6.0, even more preferably about 3.8 to about 5.5, and most preferably about 3.8 to about 5.0. The solid formulation can be further processed by milling, extrusion or other processes to add additional ingredients, such as surfactants, conditioners, fragrances, colorants, exfoliants or other cosmetic or therapeutic benefit agents. The solid formulation can be molded into various shapes, such as sticks, balls, and sticks, etc., by melting, casting into a mold and allowing it to solidify, or by extruding and stamping into a molded shape.

[0062] Example

[0063] Examples 1 to 3 and Comparative Examples 1 to 3: The relative amount of each component used in Examples 1 to 3 and Comparative Examples 1 to 3 is shown in Table 1 below:

[0064] Table 1

[0065]

[0066]

[0067] *Obtained from INOLEX, product: AminoSensyl AS94

[0068] ** Obtained from INOLEX, product: Emulsense

[0069] ***Obtained from INOLEX, product: SustOleo BA

[0070] **** Obtained from INOLEX, product: SustOleo BG

[0071] ^Obtained from Spectrum Chemical Products (New Brunswick, NJ)

[0072] Example 1 - Procedure for preparing a self-neutralizing AABC composition using Brassinoyl Valinate Ethyl Sulfonate

[0073] Brassicyl valinate esylate (BVE) and Brassica alcohol (BA) are added to an appropriately sized beaker equipped with an overhead mechanical stirrer with propeller blade and a hot plate. The mixture is gently heated while manually stirring with a spatula to melt the solid ingredients; after liquefaction, stirring is started at medium to high speed and the temperature reaches 75-80°C. Anhydrous calcium gluconate (CaG) powder with a D50 average particle size of 11 μm is slowly sieved into the molten BVE / BA blend and mixed until uniformly dispersed. After stopping stirring, the mixture is immediately poured onto a stainless steel pan, which is spread into a thin, uniform layer, cooled to ambient temperature and solidified.

[0074] The cured layer was scraped off the tray to produce a thin sheet of the self-neutralized AABC composition.

[0075] Comparative Example 1

[0076] The amounts in Table 1 and the procedure of Example 1 were used to prepare a comparative AABC composition. However, in this example, the calcium gluconate was omitted from the composition. Note that when ABA was omitted from the AABC composition, additional nonionic amphiphile was added in appropriate amounts to reach 100 wt % in this example.

[0077] Example 2 - Procedure for preparing a self-neutralized AABC composition using Brassica alcohol isoleucinate ethanesulfonate

[0078] The amounts in Table 1 and the procedure of Example 1 were used to prepare an AABC composition. However, in Example 2, the AABC was brassinolide ethylsulfonate.

[0079] Comparative Example 2

[0080] The amounts in Table 1 and the procedure of Example 1 were used to prepare a comparative AABC composition. However, in this example, the calcium gluconate was omitted from the composition.

[0081] Example 3 - Procedure for Preparing a Self-Neutralizing AABC Composition Having a Secondary Nonionic Amphiphile

[0082] The amounts in Table 1 and the procedure of Example 1 were used to prepare a self-neutralizing AABC composition. However, in Example 3, the AABC was brassica valine ester ethanesulfonate, and a secondary nonionic amphiphile, brassica glyceride, was added to the composition.

[0083] Comparative Example 3

[0084] The amounts in Table 1 and the procedure of Example 1 were used to prepare a comparative AABC composition. However, in this example, the calcium gluconate was omitted from the composition.

[0085] Embodiment 4 to 6 and comparative example 4 to 6: The relative amount of each component used in Examples 4 to 6 and Comparative Examples 4 to 6 is the same as that used in Examples 1 to 3 and Comparative Examples 1 to 3 (see Table 1). Each collected pH data is shown in Table 2 below:

[0086] Table 2

[0087]

[0088] Example 4 - Preparation of formulations containing self-neutralizing AABC compositions

[0089] The formulations were prepared as follows: Deionized water (qs to 100 wt%) was added to a beaker equipped with an overhead mechanical stirrer with a propeller blade and a hot plate, which was heated to 75-80°C. The specified amount (shown in Table 2) of the self-neutralizing AABC composition of Example 1 was slowly added to the hot water phase while mixing at a moderate speed and mixed until completely uniformly dispersed. The mixture was cooled to ambient temperature while stirring at a low moderate speed and then discharged into a container for storage. The formulations were allowed to equilibrate overnight and then the pH was measured using a pH meter. The compositions of Examples 4 to 6, including the self-neutralizing AABC composition, were characterized using a polarizing microscope and were observed to exhibit the lamellar liquid crystal phase behavior, as evidenced by the typical Maltese cross pattern.

[0090] Figure 2 is a polarized light micrograph (400x magnification) of the Example 4 formulation containing 15% of the self-neutralizing AABC composition of Example 1.

[0091] The compositions of Examples 4 and 5 containing 15% of the self-neutralized AABC composition were analyzed by SAXS to characterize the lattice spacing of the resulting lamellar liquid crystal systems in the temperature range of 20-70°C. Figure 3 and 4 The SAXS data of lamellar liquid crystal systems containing brassinolide valine ester ethanesulfonate and brassinolide isoleucine ester ethanesulfonate are shown respectively. The observed peaks indicate that the lattice spacing of the respective formulations is (7.5nm) and (7.7 nm). The disappearance of the peak at temperatures above 60 °C is indicative of a phase transition to a non-lamellar system.

[0092] Comparative Example 4

[0093] The procedure of Example 3 was repeated using the materials prepared in Comparative Example 1 in the amounts specified in Table 2.

[0094] Example 5 - Preparation of formulations containing self-neutralizing AABC compositions

[0095] The procedure of Example 4 was repeated using the self-neutralizing AABC composition prepared in Example 2 in the amounts specified in Table 2.

[0096] Comparative Example 5

[0097] The procedure of Example 4 was repeated using the materials prepared in Comparative Example 2 in the amounts specified in Table 2.

[0098] Example 6 - Preparation of Formulations Containing Self-Neutralizing AABC Compositions

[0099] The procedure of Example 4 was repeated using the self-neutralizing AABC composition prepared in Example 3 in the amounts specified in Table 2.

[0100] Comparative Example 6

[0101] The procedure of Example 4 was repeated using the materials prepared in Comparative Example 3 in the amounts specified in Table 2.

[0102] The pH data collected from these examples are shown in Figure 1 As shown in Table 2 and Figure 1 The data demonstrate the pH buffering benefit of the self-neutralizing AABC compositions (Examples 1 to 3) when dispersed in water.

[0103] It can be seen that in the state where the concentration of the AABC blend ranges from 5 wt % to 20 wt %, the aqueous composition comprising Examples 1, 2 and / or 3 exhibits an almost constant pH value of 4.3-4.5, and the comparative examples without a buffer (Comparative Examples 1, 2 and 3) exhibit a lower pH value, which decreases with increasing concentration of the AABC blend.

[0104] Thus, the self-neutralizing AABC compositions of Examples 1, 2 and 3 provide the benefits of pH values ​​suitable for formulation of compositions for use in hair care and skin care, are used in unlimited amounts, and do not require further adjustment upon mixing into aqueous media.

[0105] Example 7 - Natural Rinse-Off Conditioner

[0106] Table 3 shows the relative amounts of ingredients used in the formulation of the following typical conditioner.

[0107] Table 3

[0108]

[0109] To an appropriately sized beaker equipped with an overhead mechanical stirrer with propeller blade and a hot plate, add water and caprylhydroxamic acid (and) propylene glycol, which are heated to 75-80° C. while stirring at low-medium speed. At 70-75° C., the self-neutralized AABC blend of Example 1, Brassicyl alcohol, triheptanoin, diheptylsuccinate (and) capryloylglycerol sebacic acid copolymer, and argan kernel oil are added to the beaker.

[0110] The temperature was raised to 80-85°C and the mixture was stirred at medium-high speed for 10-15 minutes. While stirring at medium-high speed, the heating was stopped and the mixture was allowed to cool to 70°C. At 70°C, the mixture was homogenized at high speed for three minutes and then cooled to 45-50°C while stirring at low speed with an anchor blade. At 50°C, the mixture was discharged into a suitable container for storage. The resulting formulation had a pH of 4.2 and a Brookfield viscosity (RVT(D), lifter TC, 10 rpm) of 53,500 cP at room temperature (about 21°C).

[0111] Example 8 – Natural Leave-In Split End Repair Cream

[0112] Table 4 shows the relative amounts of ingredients used in the formulation of the following typical split-end repair cream.

[0113] Table 4

[0114]

[0115] To an appropriately sized beaker equipped with an overhead mechanical stirrer with a propeller blade and a hot plate, add water, caprylhydroxamic acid (and) benzyl alcohol (and) glycerin, and glycerin. Agitation is initiated at medium-low speed, and the mixture is heated to 80° C. In a separate beaker, cetyl alcohol, diheptylsuccinate (and) caprylylglycerol sebacic acid copolymer, the self-neutralizing AABC composition of Example 1, and cocos nucifera (coconut) oil are combined and heated to 80° C. (while stirring), and mixed until homogeneous.

[0116] The oil phase mixture is added to the water phase mixture at 80°C while stirring at medium-high speed. The mixture is cooled to 70°C and then homogenized at high speed for three minutes. After homogenization, the mixture is cooled to 45-50°C while stirring at low speed with an anchor blade. At 45-50°C, the mixture is discharged into a suitable container for storage.

[0117] The resulting formulation had a pH of 4.27 and a Brookfield viscosity (RVT(D), lift rod TC, 10 rpm) of 69,600 cP at room temperature (about 21°C).

[0118] Examples 9 and 10: Natural Conditioner Soap

[0119] Table 5 shows the relative amounts of ingredients used in the formulation of the following typical conditioner soap.

[0120]

[0121]

[0122] Examples 9 and 10 were prepared by a "melt and pour" procedure known to those skilled in the art. The ingredients were charged to an appropriately sized beaker and heated to 80-85°C while stirring at a moderate speed to maintain a uniform dispersion of the buffer in the mixture. The flavor was withheld from the mixture until the last 1-2 minutes of stirring. After the flavor was added, the mixture was immediately discharged into a cooling stick mold and flash cooled to maintain a uniform, homogeneous solid form. The pH values ​​of 10% solutions of the stick compositions of Examples 9 and 10 in water were 4.09 and 5.39, respectively.

[0123] Example 11 and Comparative Example 11 - Therapeutic Emulsion Formulations

[0124] Table 6 shows the relative amounts of ingredients used in the formulations of the therapeutic emulsion formulations of Example 11 and Comparative Example 11. The stated viscosity and pH value of each formulation is also shown in Table 6.

[0125]

[0126]

[0127] Embodiment 11

[0128] To an appropriately sized beaker equipped with an overhead mechanical stirrer with propeller blade and a hot plate, add the water, sodium chloride, and glycerin. Begin stirring at medium speed and begin heating to bring the batch temperature to 80-85° C. Slowly sift the colloidal oatmeal into the batch and mix until evenly dispersed and no lumps appear.

[0129] When the temperature reaches 60-65°C, the self-neutralizing AABC of Example 3 is added along with isopropyl palmitate, petrolatum, and dimethicone. After reaching 80-85°C, the batch is mixed at medium-high speed for 10-15 minutes to ensure that all ingredients are melted and evenly dispersed. The heat is removed and the batch is allowed to cool to about 70°C with continued stirring. At 70°C, the batch is homogenized at 3000 rpm for three minutes and then stirring is resumed at low-medium speed while cooling. Once the batch temperature is cooled to 55°C, caprylylhydroxamic acid (and) benzyl alcohol (and) glycerin are added. While stirring at low speed with an anchor blade, the mixture is cooled to 40-45°C.

[0130] The mixture was discharged into a suitable container for storage at about 40° C. The resulting formulation had a pH of 4.19 and a Brookfield viscosity (RVT(D), Lifting Rod TC, 10 rpm) of 12,400 cP at room temperature (about 21° C.).

[0131] Comparative Example 11

[0132] Comparative Example 11 was prepared using Comparative Example 3, a non-self-neutralizing AABC composition, in the same manner as Example 11. Compared to Example 11, the resulting emulsion exhibited an undesirably low pH (2.73) and an undesirably low viscosity (5,400 cP).

[0133] Example 12 and Comparative Example 12 - High Moisturizing Cream

[0134] Table 7 shows the relative amounts of ingredients used in the formulations of Example 12 and Comparative Example 12. The stated viscosity and pH value of each formulation are also shown in Table 7.

[0135]

[0136] Example 12

[0137] In an appropriately sized beaker equipped with an overhead mechanical stirrer with a propeller blade and a hot plate, an oil phase is prepared by combining helianthus annuus (sunflower) seed oil, caprylic / capric triglyceride, and isopropyl palmitate. While stirring at low to medium speed, the mixture is heated to 75-80° C. While heating, the self-neutralizing AABC composition of Example 3 is added and the oil phase is mixed until homogeneous.

[0138] The oil phase was maintained at 75-80°C with stirring to maintain a uniform dispersion without settling. In a separate beaker equipped with an overhead mechanical stirrer with propeller blade and hot plate, water and caprylhydroxamic acid (and) glyceryl caprylate (and) glycerin were combined and heated to 75-80°C while stirring at low-medium speed. At 75-80°C, the stirring speed was increased to medium-high speed and the hot oil phase was added to the main batch and mixed at 75-80°C until uniform.

[0139] Heating was stopped and the batch was allowed to cool to about 70°C and then homogenized at 3000 rpm for three minutes. While cooling, agitation was resumed at low to medium speed with an anchor blade. Once the batch temperature was cooled to about 45-50°C, the mixture was discharged into a suitable container for storage. The resulting formulation had a pH of 4.16 and a Brookfield viscosity (RVT(D), lifter TC, 10 rpm) of 69,400 cP at room temperature (about 21°C).

[0140] Comparative Example 12

[0141] Comparative Example 12 was prepared using Comparative Example 3, a non-self-neutralizing AABC composition, in the same manner as Example 12. Compared to Example 12, the resulting cream exhibited an undesirably low pH (2.55) and an undesirably low viscosity (21,800 cP).

[0142] Example 13 - Natural Shaving Lotion

[0143] Example 13 was prepared according to the same general procedure described in Example 12. Sweet orange (orange) peel oil and flavor were post-added to the batch during cooling when the temperature had cooled to <55° C. The resulting formulation had a pH of 4.03 and a Brookfield viscosity (RVT(D), Lifting rod TC, 10 rpm) of 50,400 cP at room temperature (about 21° C.).

[0144] Table 8 shows the ingredients used in Example 13 and their relative amounts.

[0145]

[0146]

[0147] Where applicable, chemicals are identified by INCI name in accordance with the guidelines of the International Nomenclature of Cosmetic Ingredients. Additional information, including supplier and trade names, can be found under the corresponding INCI monograph in the International Cosmetic Ingredient Dictionary and Manual, 16th Edition, published by the Personal Care Products Association, Washington, D.C., or on the Personal Care Products Association Online Information Library website ( http: / / online.personalcarecouncil.org ).

[0148] It should be understood that those skilled in the art may make changes to the above embodiments without departing from the broad concept of the present invention. Therefore, it is understood that the present invention is not limited to the specific embodiments disclosed, but is intended to cover modifications of the scope and essence of the present invention as defined in the appended claims.

Claims

1. A cationic composition based on a self-neutralizing amino acid, comprising: 10 wt % to 70 wt % of a cationic ester based on an amino acid, 2 wt % to 25 wt % of an anhydrous buffer and a nonionic amphiphilic molecule in an amount up to 100 wt % of the composition, wherein the amino acid-based cationic ester is selected from the group consisting of canola valine ester ethanesulfonate, cetyl valine ester ethanesulfonate, cetearyl valine ester ethanesulfonate, stearyl valine ester ethanesulfonate, isostearyl valine ester ethanesulfonate, behenyl valine ester ethanesulfonate, octyldodecanol valine ester ethanesulfonate, decyltetradecyl valine ester ethanesulfonate, canola isoleucinate ester ethanesulfonate, cetyl isoleucinate ester ethanesulfonate, cetearyl isoleucinate ester ethanesulfonate, stearyl isoleucinate ester ethanesulfonate, isostearyl isoleucinate ester ethanesulfonate, behenyl isoleucinate ester ethanesulfonate, octyldodecanol isoleucinate ester ethanesulfonate, decyltetradecyl isoleucinate ester ethanesulfonate and mixtures thereof; wherein the anhydrous buffer is calcium gluconate; wherein the nonionic amphiphilic molecule has 10 to 35 carbon atoms; wherein the composition is in anhydrous solid form and is a dispersion of particles of the anhydrous buffer in a mixture of the amino acid-based cationic ester and the nonionic amphiphilic molecule; and The pH value of a 10 wt % aqueous solution or dispersion of the composition is greater than 4.

2. The composition of claim 1, wherein the nonionic amphiphilic molecule is selected from the group consisting of fatty alcohols, fatty glycerides, fatty acid alcohol esters, fatty esters of polyglycerol, fatty esters of methyl glucose, fatty esters of sorbitan, and mixtures thereof.

3. The composition of claim 1, wherein the nonionic amphiphilic molecule is selected from the group consisting of brassicyl alcohol, cetyl alcohol, cetearyl alcohol, stearyl alcohol, behenyl alcohol, and mixtures thereof.

4. The composition according to claim 1, wherein the amino acid-based cationic ester comprises two or more amino acid-based cationic esters selected from the group consisting of brassicyl valine ester ethanesulfonate, cetyl valine ester ethanesulfonate, cetearyl valine ester ethanesulfonate, stearyl valine ester ethanesulfonate, isostearyl valine ester ethanesulfonate, behenyl valine ester ethanesulfonate, octyldodecanol valine ester ethanesulfonate, decyltetradecyl valine ester ethanesulfonate, brassicyl isoleucinate ethanesulfonate, cetyl isoleucinate ethanesulfonate, cetearyl isoleucinate ethanesulfonate, stearyl isoleucinate ethanesulfonate, isostearyl isoleucinate ethanesulfonate, behenyl isoleucinate ethanesulfonate, octyldodecanol isoleucinate ethanesulfonate, decyltetradecyl isoleucinate ethanesulfonate, and mixtures thereof.

5. The composition of claim 1, wherein the nonionic amphiphilic molecule comprises two or more nonionic amphiphilic molecules selected from the group consisting of fatty alcohols, fatty glycerides, fatty acid alcohol esters, fatty esters of polyglycerol, fatty esters of methyl glucose, fatty esters of sorbitan, and mixtures thereof.

6. The composition of claim 1, wherein the ratio of the anhydrous buffer to the amino acid-based cationic ester is 9.5:27.2, 9.6:36.0, or 11.0:31.4 by weight.

7. The composition of claim 1, wherein the average particle size of the particles of the anhydrous buffer is less than 100 μm.

8. The composition of claim 7, wherein the average particle size is less than 50 μm.

9. The composition of claim 4, wherein the amino acid-based cationic ester is brassinoyl valine ester ethanesulfonate or brassinoyl isoleucine ester ethanesulfonate.

10. The composition according to claim 1, wherein the amount of the amino acid-based cationic ester is 20 wt% to 50 wt%, and the amount of the anhydrous buffer is 6 wt% to 15 wt%.

11. An aqueous formulation comprising the self-neutralizing amino acid-based cationic composition of any one of claims 1 to 10, water, and at least one other additive, wherein the pH of the aqueous formulation is greater than 4.

12. A solid formulation comprising the self-neutralizing amino acid-based cationic composition of any one of claims 1 to 10 and at least one additive.

13. The solid formulation of claim 12, wherein the solid formulation is anhydrous.

14. The solid formulation of claim 12, wherein the solid formulation is in the form of a molded shape.

15. A cationic composition based on a self-neutralizing amino acid, include: 10 to 70 wt% of an amino acid-based cationic ester of formula (I): Wherein the amino acid is L-valine and R 1 isopropyl, or the amino acid is L-leucine and R 1 isobutyl, or the amino acid is L-isoleucine and R 1 is sec-butyl; R 2 is brassicyl, cetyl, cetearyl, stearyl, isostearyl, behenyl, octyldodecyl or decyltetradecyl, wherein X - represents the conjugate base, 2 wt% to 25 wt% of an anhydrous buffer selected from calcium gluconate, and Nonionic amphiphilic molecules, used in an amount such that the total amount of the composition reaches 100 wt%; wherein the nonionic amphiphilic molecule has 10 to 35 carbon atoms; wherein the composition is in anhydrous solid form and is a dispersion of particles of the anhydrous buffer in a mixture of the amino acid-based cationic ester and the nonionic amphiphilic molecule; and The pH value of a 10 wt % aqueous solution or dispersion of the composition is greater than 4.

16. The composition of claim 15, wherein the average particle size of the particles of the anhydrous buffer is less than 100 μm.

17. The composition of claim 16, wherein the average particle size is less than 50 μm.

18. The composition of claim 15, wherein the nonionic amphiphile is selected from the group consisting of brassicyl alcohol, cetyl alcohol, cetearyl alcohol, stearyl alcohol, behenyl alcohol, and mixtures thereof.

19. The composition according to claim 15, wherein the amount of the amino acid-based cationic ester is 20 wt% to 50 wt%, and the amount of the anhydrous buffer is 6 wt% to 15 wt%.

20. The composition of claim 15, wherein the ratio of the anhydrous buffer to the amino acid-based cationic ester is 9.5:27.2, 9.6:36.0, or 11.0:31.4 by weight.

21. An aqueous formulation comprising the self-neutralizing amino acid based cationic composition of any one of claims 15-20, water, and at least one other additive.

22. A solid formulation comprising the self-neutralizing amino acid based cationic composition of any one of claims 15-20 and at least one additive.

23. The solid formulation of claim 22, wherein the solid formulation is anhydrous.

24. The solid formulation of claim 22, wherein the solid formulation is in the form of a molded shape.

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