WO2020181276A1 - Self-neutralizing amino acid based cationic compositions - Google Patents

Self-neutralizing amino acid based cationic compositions Download PDF

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Publication number
WO2020181276A1
WO2020181276A1 PCT/US2020/021696 US2020021696W WO2020181276A1 WO 2020181276 A1 WO2020181276 A1 WO 2020181276A1 US 2020021696 W US2020021696 W US 2020021696W WO 2020181276 A1 WO2020181276 A1 WO 2020181276A1
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Prior art keywords
esylate
composition
valinate
aabc
amino acid
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PCT/US2020/021696
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English (en)
French (fr)
Inventor
Rocco V. Burgo
Mei Chen
Michael J. Fevola
Gary MOSSER
Brittany PEASE
Original Assignee
Inolex Investment Corporation
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Publication date
Application filed by Inolex Investment Corporation filed Critical Inolex Investment Corporation
Priority to EP20766131.5A priority Critical patent/EP3934638A4/en
Priority to JP2021552616A priority patent/JP7548925B2/ja
Priority to CA3132043A priority patent/CA3132043C/en
Priority to CN202080019230.6A priority patent/CN113677337B/zh
Priority to KR1020217032061A priority patent/KR102613882B1/ko
Priority to AU2020232853A priority patent/AU2020232853B2/en
Priority to BR112021017173-8A priority patent/BR112021017173B1/pt
Publication of WO2020181276A1 publication Critical patent/WO2020181276A1/en
Priority to JP2024076313A priority patent/JP2024105461A/ja

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    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
    • A61K8/44—Aminocarboxylic acids or derivatives thereof, e.g. aminocarboxylic acids containing sulfur; Salts; Esters or N-acylated derivatives thereof
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/02—Cosmetics or similar toiletry preparations characterised by special physical form
    • A61K8/0216—Solid or semisolid forms
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/34—Alcohols
    • A61K8/342—Alcohols having more than seven atoms in an unbroken chain
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/36—Carboxylic acids; Salts or anhydrides thereof
    • A61K8/365—Hydroxycarboxylic acids; Ketocarboxylic acids
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/37—Esters of carboxylic acids
    • A61K8/375—Esters of carboxylic acids the alcohol moiety containing more than one hydroxy group
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/64—Proteins; Peptides; Derivatives or degradation products thereof
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
    • A61K8/81—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds
    • A61K8/8141—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides or nitriles thereof; Compositions of derivatives of such polymers
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00—Preparations for care of the skin
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q5/00—Preparations for care of the hair
    • A61Q5/12—Preparations containing hair conditioners
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q9/00—Preparations for removing hair or for aiding hair removal
    • A61Q9/02—Shaving preparations
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
    • A61K2800/20—Chemical, physico-chemical or functional or structural properties of the composition as a whole
    • A61K2800/30—Characterized by the absence of a particular group of ingredients
    • A61K2800/31—Anhydrous
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
    • A61K2800/40—Chemical, physico-chemical or functional or structural properties of particular ingredients
    • A61K2800/48—Thickener, Thickening system
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
    • A61K2800/40—Chemical, physico-chemical or functional or structural properties of particular ingredients
    • A61K2800/52—Stabilizers
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
    • A61K2800/40—Chemical, physico-chemical or functional or structural properties of particular ingredients
    • A61K2800/54—Polymers characterized by specific structures/properties
    • A61K2800/542—Polymers characterized by specific structures/properties characterized by the charge
    • A61K2800/5426—Polymers characterized by specific structures/properties characterized by the charge cationic

Definitions

  • Non-petrochemically derived cationic emulsifiers that are neutralized amino acid esters are described and claimed in U.S. Patent No. 8,105,569 of Burgo and its related applications.
  • These amino acid-based cationic esters (hereinafter“AABC”s) of Burgo may be supplied as an anhydrous form, i.e., a form that does not contain water in any significant quantity, e.g, less than about 5% water by weight.
  • the AABC compositions of Burgo are comprised predominantly of amino acid esters where the amino groups are neutralized by strong organic acids, e.g., ethanesulfonic acid (ESA), which renders the amino acid esters cationically charged species.
  • ESA ethanesulfonic acid
  • the AABC compositions may also contain minor quantities, e.g., ⁇ 2 wt%, of unreacted amino acids, e.g, isoleucine or valine, which are also neutralized by the strong organic acids to yield strongly acidic salts, e.g, isoleucine esylate or valine esylate.
  • AABC compositions of Burgo When the AABC compositions of Burgo are dissolved or dispersed in aqueous media, they tend to yield aqueous compositions with rather low pH values, e.g, pH ⁇ 3.0.
  • pH ⁇ 3.0 e.g. pH ⁇ 3.0.
  • the AABC is the salt of a strong acid and a weak base.
  • the anion, i.e., the conjugate base of the strong acid will become a spectator ion and fail to attract protons, while the cation from the weak base will donate protons to the water forming hydronium ions (H 3 CC), thus lowering the solution pH value.
  • the strongly acidic amino acid salts e.g, isoleucine esylate or valine esylate, present as unreacted byproducts in the AABC composition, will also contribute to lowering the solution pH.
  • the invention described herein includes a self-neutralizing amino acid-based cationic composition that contains an amino acid-based cationic ester, a nonionic amphiphile, and an anhydrous buffering agent.
  • the composition when dispersed or dissolved in an aqueous solvent, provides a resultant solution/dispersion having a pH of greater than about 4.
  • the amino acid-based cationic ester may be a reaction product of (i) an amino acid having a non-polar side chain, and an amine group that has been neutralized with an acid; with (ii) a long chain fatty alcohol.
  • the resulting composition is in an anhydrous solid form.
  • Formulations containing the amino acid-based cationic ester and/or a composition that includes it, are also disclosed.
  • Fig. 1 shows the pH of aqueous compositions as a function of wt% AABC blend in the composition of Examples 4 to 6 and Comparative Examples 4 to 6;
  • Fig. 2 is a polarized light micrograph (400x magnification) of an exemplary formulation of the invention that includes 15% of the self-neutralizing AABC composition prepared in accordance with the invention;
  • Fig. 3 show SAXS data for lamellar LC systems comprising brassicyl valinate esylate.
  • Fig. 4 show SAXS data for lamellar LC systems comprising brassicyl isoleucinate esylate.
  • 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 a desirable pH value (about 3.5 to about 7) eliminating the need for pH adjustment via addition of base.
  • the present invention also provides methods for preparing self-neutralizing amino acid-based cationic compositions and methods for preparing compositions comprising self-neutralizing amino acid-based cationic compositions.
  • the self-neutralizing amino acid-based cationic compositions as described herein include an amino acid-based cationic ester, i.e ., a neutralized amino acid ester, a nonionic amphiphile and an anhydrous buffering agent (hereinafter“ABA”).
  • ABA an anhydrous buffering agent
  • Each component may be independently present in the composition in singular form (e.g ., one type of amino acid-based cationic) or as a mixture (e.g.., a mixture of two or more amino acid-based cationic esters). Details of the individual components of the composition are provided below.
  • an aqueous solvent such as water
  • the resultant solution/dispersion has a pH of 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.
  • AABC neutralized amino acid ester
  • AABC amino acid-based cationic ester
  • the contents of Burgo are imported herein by reference, and which is provided for convenience at Appendix A.
  • AABC may be prepared from the esterification of (i) an amino acid having a non-polar side chain wherein the amine group of the amino acid has been neutralized with an acid; with (ii) a long chain fatty alcohol.
  • the AABC may represented by the structure of formula (I):
  • R 1 represents an alkyl group, which may be branched or linear. It may have one to ten carbon atoms or two to six carbon atoms.
  • R 2 represents a carbon chain that may be linear or branched. It may contain ten to fifty carbon atoms or twenty-four to thirty-two carbon atoms. The chain of R 2 may contain at least one unsaturated carbon atom.
  • R 1 represents an alkyl group, which may be branched or linear. It may have one to ten carbon atoms or two to six carbon atoms.
  • R 2 represents a carbon chain that may be linear or branched. It may contain ten to fifty carbon atoms or twenty-four to thirty-two carbon atoms. The chain of R 2 may contain at least one unsaturated carbon atom.
  • R 2 is an alkyl group having eight to twenty-four carbon atoms.
  • X represents the conjugate base of the acid used to neutralize the amino acids ester.
  • Amino acids for the formation of the AABC include any that are neutral.
  • Other options may include any a,w-aminoalkylcarboxylic acid, e.g ., 11-aminoundecanoic acid or 12- aminododecanoic acid.
  • the amine group of the amino acid is neutralized with an acid and is reacted with a long chain fatty alcohol.
  • Suitable fatty alcohols may be linear and/or branched and may additionally be saturated and/or unsaturated. It may be preferred that the fatty alcohol contains about ten to about fifty or about twenty-four to about thirty -two carbon atoms. In an embodiment, linear and/or branched fatty alcohols containing from about twelve to about twenty -two carbon atoms may be preferred. In another embodiment, linear fatty alcohols containing about sixteen to about twenty-four carbon atoms are preferred.
  • 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 advisable that the fatty alcohols are derived from non-petrochemical sources.
  • the AABC is a reaction product of the amino acid and the fatty alcohol, where 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 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 the fatty alcohol produced from the seed oils derived from plants of the family Brassicaceae containing or primarily containing Ci8, C20, and C22 fatty alcohols.
  • AABC a fatty alcohol ester with the amino acid being L-valine or L-isoleucine, neutralized with ethanesulfonic acid and which is preferably solid at 25 °C.
  • Such AABCs may 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; brassicyl isoleucinate esylate, cetyl isoleucinate esylate, cetearyl isoleucinate esylate, stearyl isoleucinate esylate, isostearyl isoleucinate esylate, behenyl isoleucinate esylate, octyldodecyl isoleucinate esylate, decyltetrade
  • AABC may be synthesized by any methods known or developed in the art.
  • the composition also includes at least one nonionic amphiphile; it may be preferred that the selected nonionic amphiphile is one that is a solid 25 °C. It may, in some
  • exemplary nonionic amphiphiles may include:
  • Fatty alcohols such as, for example, straight chain or branched fatty alcohol comprising 12 or more carbon atoms, including, for example, lauryl, myristyl, cetyl, cetearyl, stearyl, isostearyl, oleyl, arachidyl, behenyl, octyldodecyl, decyltetradecyl, coconut alcohol, palm alcohol, palm kernel alcohol, brassica alcohol, hydrogenated rapeseed alcohol; preferably linear fatty alcohol comprising 16 or more carbon atoms; most preferably brassica, cetyl, cetearyl, stearyl, or behenyl;
  • Fatty glyceryl esters such as, for example, mono-, di-, or triester of glycerol or mixtures thereof that include esters of glycerol and one or more fatty acids comprising 12 or more carbon atoms, such as, for example, glyceryl laurate, glyceryl myristate, glyceryl palmate, glyceryl sesqui stearate, glyceryl stearate, glyceryl stearate se, glyceryl behenate, glyceryl distearate, brassica glycerides, hydrogenated rapeseed glycerides, hydrogenated coco glycerides, hydrogenated C12-18 glycerides, hydrogenated palm glycerides, hydrogenated soy glycerides; preferably brassica glycerides; [0030] Fatty glycol esters, such as, for example, mono- or diester of ethylene glycol or mixtures thereof; esters of g
  • Fatty esters of polyglycerol such as, for example, polyglyceryl esters are monoacyl or polyacyl esters ( e.g ., bearing an average of 1.5 to 10 ester groups per polyglyceryl chain) of polyglycerols having an average degree of polymerization of 2 to 10 glyceryl repeat units and having an acyl group of about 12 to about 24 carbon atoms, where acyl groups may include lauroyl, cocoyl, myristoyl, palmitoyl, stearoyl, arachidonoyl, behenoyl, and brassicoyl, such as, for example, polyglyceryl-3 stearate, polyglyceryl-3 stearate SE, polyglyceryl-4 stearate, polyglyceryl- 10 stearate, polyglyceryl-6 sesqui stearate, polyglyceryl-4 pentastearate, polyglyceryl-6 pentastearate, polyglyceryl-
  • Fatty esters of methyl glucose such as, for example, methyl glucose esters like monoacyl or polyacyl esters (e.g., bearing an average of 1.5 to 3 ester groups per methyl glucose unit) of methyl glucose when an acyl group of about 12 to about 24 carbon atoms, where the acyl groups may include lauroyl, cocoyl, myristoyl, palmitoyl, stearoyl,
  • arachidonoyl, behenoyl, and brassicoyl 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 sesqui stearate;
  • Fatty esters of sorbitan such as, for example, monoacyl or polyacyl esters (e.g, bearing an average of 1.5 to 4 ester groups per methyl glucose unit) of sorbitan and having an acyl group of about 12 to about 24 carbon atoms, including, for example, lauroyl, cocoyl, myristoyl, palmitoyl, stearoyl, arachidonoyl, behenoyl, and brassicoyl Examples include sorbitan cocoate, sorbitan dioleate, sorbitan distearate, sorbitan laurate, sorbitan oleate, sorbitan olivate, sorbitan palmitate, sorbitan palmate, sorbitan sesquioleate, sorbtian sesquisteatate, sorbitan stearate, sorbitan trioleate, and sorbitan tristearate.
  • monoacyl or polyacyl esters e.g, bearing an average of 1.5 to 4 ester
  • the composition further includes an anhydrous buffering agent (“ABA”).
  • ABA anhydrous buffering agent
  • anhydrous it is meant that the material is substantially free of added water, preferably containing less than about 5% water, more preferably less than about 4% water, even more preferably less than about 2% water, and most preferably less than about 1.5% water.
  • Anhydrous materials may contain minor amounts of incidental water, e.g ., from absorption of ambient humidity or processing conditions, e.g., washing followed by incomplete drying).
  • the ABA is in a particulate form or a powder form, for example, it is a finely divided solid having a small particle size, preferably less than about 100 pm.
  • ABAs suitable for use in the inventive composition include any known or to be developed in the art or combinations of the same.
  • the ABA is a material capable of maintaining the pH of the aqueous solution when the AABC composition is dissolved in water.
  • the ABA may be a free-flowing solid with average particle size of less than about 100 pm, preferably less than about 75 pm, more preferably less than about 50 pm, even more preferably less than about 25 pm, in certain embodiments, the average particle size will be less than about 20 pm.
  • a powder form of small particle size may be used to facilitate the maintenance of uniform dispersion of the ABA throughout the composition during processing in the molten state and during the process of cooling and solidification to yield a solid form with buffering agent dispersed homogeneously throughout.
  • the ABA selected may be a salt of a strong base and a weak organic acid, e.g. , where strong base is sodium hydroxide, potassium hydroxide, calcium hydroxide and the like, and the weak acid is gluconic acid, citric acid, lactic acid, and the like.
  • Exemplary ABAs for use in the composition of the invention include, for example, alkali metals or alkaline earth metal salts of gluconic acid, e.g. , sodium gluconate, calcium gluconate.
  • the composition of the invention may contain any of the two/three above-described components in any relative quantity; such relative quantities may vary depending on several factors, including, for example, manufacturing parameters, the contemplated end use of the composition, and the like as is appreciated in the art. Thus, the variation of the relative quantities is a matter of routine by a person of skill in the art.
  • the 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 reference to the weight of the total composition.
  • the balance of the composition may be made up of the selected nonionic amphiphile(s). If other ingredients at included in the composition of the invention, the selected nonionic amphiphile(s) may be present in amount of at least about 10 wt%, about 15 wt% to about 70 wt%, in some embodiments preferably about 20 wt% to about 40 wt%, each with reference to the total composition.
  • the ratio of AABC to ABA in the composition may be: (i) on a weight basis (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 1 :3; or (ii) on a molar basis: 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.
  • the molar ratio of AABC to anhydrous buffering agent may be 1 : 1 or 1 :2.
  • composition is, in many embodiments, in an anhydrous form, preferably an anhydrous solid form.
  • the self-neutralizing AABC compositions may include other ingredients. Such ingredients are preferably in a powder form and/or are also anhydrous. Examples include water-soluble polymers or gums, such as guar hydroxypropyltrimonium chloride,
  • hydroxypropyl guar polyquaternium-10, hydroxy ethyl cellulose, hydroxypropylmethyl cellulose, starch, guar gum, cassia gum, and the like; chelating agents, such as tetrasodium EDTA, disodium EDTA, tetrasodium glutamate diacetate, and the like; and zwitterionic surfactants, such as cocamidopropyl betaine, cocamidopropyl hydroxysultaine,
  • the self-neutralizing AABC compositions may also contain other solid or semi solid ingredients that are capable of being incorporated into the composition in the molten phase, such as, for example, plant derived triglycerides, i.e., oils and butters, and waxes and wax esters, preferably nonpetrochemically derived.
  • plant derived triglycerides i.e., oils and butters
  • waxes and wax esters preferably nonpetrochemically 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 compositions.
  • the self-neutralizing AABC compositions of the invention may be prepared by any process known or developed in the art. However, for illustrative purposes, a general process of manufacture is as follows: the AABC and nonionic amphiphiles are heated until completely melted and mixed to form a homogenous molten mixture. The anhydrous buffering agent is dispersed in the molten mixture to produce a uniform dispersion of the powder in the molten mixture, preferably under shear. This dispersion is maintained under heat and shear during processing to ensure it remains homogeneous while in the molten state.
  • a homogeneous mixture may be maintained by applying constant shear, e.g. , with a mechanical mixer.
  • recirculation of the contents via pumping and in-line shear mixing may be combined with mechanical mixing to maintain a homogeneous dispersion of the ABA in the molten mixture.
  • the molten mixture is then cooled. If desired a solid may be achieved to increase convenience of subsequent post-manufacture handling and processing, if such is desired.
  • the composition may be subject to various post manufacture processes, such as for example, flaking, pastillation, prilling, beading, extrusion and pelletizing, etc.
  • the mixture can be spread in a thin layer on a chilled surface and allowed to cool and solidify; the resulting solid sheet can be broken into small pieces (flakes) and stored for subsequent compounding into formulations.
  • the cooling and solidification processes are preferentially configured to ensure that a uniform homogeneous distribution of buffering agent is present in the solid form, e.g, from flake to flake or pastille to pastille, and from the beginning of a run to the end of a run when conducted on large scale continuously operating equipment; therefore, cooling and solidification must occur on a time scale that is much faster than the settling rate (i.e., sedimentation velocity) of the ABA particulate in the molten mixture.
  • settling rate i.e., sedimentation velocity
  • compositions of the invention may be incorporated into many consumer and industrial end formulations, for example, formulations for personal care, home & institutional care, pharmaceutical, veterinary care, oral care, textile care, metalworking, food processing, and industrial applications.
  • 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, humectants, conditioning agents for hair, skin or nails, chelating agents, active agents, beaching or whitening agents, additional pH adjusting agents, fragrances, colorants, exfoliating agents, antioxidants, botanical ingredients, e.g ., plant extracts, mica, smectite, thickeners, pharmaceuticals, cannabinoids, oils, dyes, waxes, amino acids, nucleic acids, vitamins, hydrolyzed proteins and derivatives thereof, glycerine and derivates thereof, enzymes, anti-inflammatory and other medicaments, microbiocides, antifungals, antiseptics, antioxidants, UV absorbers, dyes and pigments, preservatives, sunscreen active agents, sweat retardants, oxidizers, pH balancing agents, glyceryl monoesters, moisturizers, peptides and derivatives thereof, anti -aging actives, hair growth promoters, anti cellulite actives and the like acceptable for
  • Such formulations may have end use as, for example without limitation, a conditioner of hair, nails, skin or textile, shampoo, hair spray, mustache/beard oils or waxes, hair-styling preparation, permanent wave liquids, hair colorant, glaze, skin lotion, face & body wash, makeup remover, cleansing lotion, emollient lotion/cream bar soap, shaving creams, sunscreen, sunburn treatment, deodorants, moisture gel, moisture essence, UV exposure preventing essence, shaving foam, face powder, foundation, lipstick, blush, eyeliner, wrinkle and anti-aging cream, eye shadow, eyebrow pencils, mascara, mouthwash, toothpaste, an oral care composition, a skin cleansing composition, a textile cleansing compositions, a dish cleaning composition, a hair or fur cleansing composition, a deodorant or antiperspirant, a cosmetic, a hair styling composition, a skin moisturizer, a skin conditioner, a hair conditioner and a nail conditioner.
  • a conditioner of hair, nails, skin or textile shampoo, hair spray, mustache/beard oils or waxes,
  • formulations including the self-neutralizing AABC compositions of the invention may be prepared by any process known or developed in the art. However, for illustrative purposes, a general process is as follows: A water 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 allowed to disperse and melt into the water phase. The formulation is mixed until the buffering agent of the AABC is dissolved and a stable, uniform pH value is obtained throughout the resulting composition.
  • the self-neutralizing AABC composition is heated to form a liquid; the liquid is maintained under shear (mixing) to ensure homogenous distribution of the buffering agent.
  • a water phase is heated to about the same temperature as the molten self-neutralizing AABC composition.
  • the molten self-neutralizing AABC composition is combined with the heated water phase while heating and mixing; proper agitation is employed to ensure uniform mixing of the two phases.
  • the formulation is mixed until the buffering agent of the AABC is dissolved and a stable, uniform pH value is obtained throughout the resulting composition.
  • other ingredients may be added as appropriate to either the water phase or the molten self-neutralizing AABC phase before the combination of the two phases, or to the resulting composition after the two phases have been combined.
  • fatty alcohols may be mixed with the molten prior to combination with the water phase.
  • water- soluble ingredients such as humectants, chelating agents, viscosity increasing agents, e.g., water-soluble polymers, and the like, may be added to the water phase prior to combination with the molten self-neutralizing AABC phase.
  • aqueous formulations prepared using the self-neutralizing AABC composition of the present invention will exhibit lamellar liquid crystalline (LC) phase behavior.
  • LC phase behavior is readily characterized using techniques familiar to those skilled in the art, such as polarized light microscopy, small-angle X-ray scattering (SAXS), and cryo freeze-fracture scanning electron microscopy (cryo-SEM).
  • Lamellar LC systems may be characterized by the spacing of the lamellar bilayer sheets, known as the D-spacing.
  • the lamellar LC phases formed by the compositions of the present invention may have D-spacings as measured by SAXS from about 1 to about 100 nm, with certain embodiments having D- spacings from about 2 nm to about 25 nm, and preferred embodiments having D-spacings from about 3 nm to about 15 nm.
  • the D-spacing of the lamellar LC phases can be modulated by altering one or more variables, including the carbon chain lengths of the AABCs and/or the 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 amphiphile(s) in either the self-neutralizing AABC composition or in the formulation itself, e.g., additional AABC or nonionic amphiphile maybe be added to the formulation comprising the self-neutralizing AABC composition to affect the D-spacing of the lamellar LC phase.
  • additional AABC or nonionic amphiphile maybe be added to the formulation comprising the self-neutralizing AABC composition to affect the D-spacing of the lamellar LC phase.
  • the pH, ionic strength, or level of dispersed oil phase in the formulation may also be varied to influence lamellar D-spacing.
  • the lamellar LC phases of the present invention preferably have D-spacings that remain constant over the temperature range of 20 - 60°C.
  • the self-neutralizing AABC is heated to a molten state and mixed with appropriate agitation to maintain uniform distribution of the buffering agent in the mixture. Additional ingredients are added and mixed into the molten mixture. The mixture is cooled to yield a solid formulation that exhibits a pre- selected pH value upon use by the end consumer.
  • a 10% solution of the solid formulation will preferably have a pH value of about 3.5 - about 6.5, more preferably about 3.7 - about 6.0, even more preferably about 3.8 - about 5.5, and most preferably about 3.8 - about 5.0.
  • the solid formulation maybe further processed via milling, extrusion, or other processes to incorporate additional ingredients such as surfactants, conditioning agents, fragrances, colors, exfoliating agents, or other cosmetic or therapeutic benefit agents.
  • the solid formulation may be fabricated into a variety of forms such as bars, balls, sticks, and the like, by melting, casting into molds and allowing to solidify, or via extrusion and stamping with a press into a molded shape.
  • Examples 1 to 3 and Comparative Examples 1 to 3 The relative amounts of each ingredient used in Examples 1 to 3 and Comparative Examples 1 to 3 are shown below in Table 1 :
  • Example 1 Procedure to Prepare a Self-Neutralizing AABC Composition Using Brassicyl Valinate Esylate
  • Brassicyl valinate esylate (BVE) and brassica alcohol (BA) were charged to an appropriately sized beaker equipped with overhead mechanical stirrer and propeller blade and hotplate for heating. The mixture was gently heated while manually stirring with spatula to melt the solid ingredients; upon liquefication, mixing at medium-high speed was started and the temperature brought to 75 - 80 °C. Anhydrous calcium gluconate (CaG) powder having a D50 average particle size of 11 pm was slowly sifted into the molten BVE/BA blend and mixed until uniformly dispersed. Immediately upon stopping stirring, the mixture was poured onto a stainless steel tray, spread into a uniform thin layer, and allowed to cool to ambient temperature and solidify.
  • BVE brassicyl valinate esylate
  • BA brassica alcohol
  • the solidified layer was scrapped off the tray to yield the flakes of the self- neutralizing AABC composition.
  • Example 2 The amounts in Table 1 and the procedure of Example 1 were used to prepare a comparative AABC composition. However, the calcium gluconate was omitted from the composition in this example. Note that when the ABA is omitted from the AABC composition, additional nonionic amphiphile is added in q.s. in the example to achieve 100wt%.
  • Example 2- Procedure to Prepare Self-Neutralizing AABC Composition Using
  • Brassicyl Isoleucinate Esylate [0067] The amounts in Table 1 and the procedure of Example 1 were used to prepare an AABC composition. However, in Example 2, the ABC was brassicyl isoleucinate esylate.
  • Example 3 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 brassicyl valinate esylate and a secondary nonionic amphiphile, brassica glyceride, was added to the composition.
  • Examples 4 to 6 and Comparative Examples 4 to 6 The relative amounts of each ingredient used in Examples 4 to 6 and Comparative Examples 4 to are the same as those used in Examples 1 to 3 and Comparative Examples 1 to 3 (see Table 1). The pH data collected for each are shown below in Table 2:
  • Example 4 Preparation of a Formulation Including Self-Neutralizing AABC Composition
  • a formulation was prepared as follows: To a beaker equipped with overhead mechanical stirrer and propeller blade and hotplate for heating was charged deionized water (q.s. to 100 wt%), which was heated to 75 - 80 °C.
  • deionized water q.s. to 100 wt%
  • the Aself-neutralizing ABC composition of Example 1 in the specified amount (shown in Table 2) was slowly added to the hot water phase while mixing at medium speed and mixed until completely and uniformly dispersed.
  • the mixture was allowed to cool to ambient temperature while mixing as low-medium speed and was then discharged to a container for storage.
  • the formulation was 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 polarized light microscopy and observed to exhibit lamellar LC phase behavior, as evidenced by the characteristic Maltese cross pattern.
  • Figure 2 is a polarized light micrograph (400x magnification) of the Example 4 formulation comprising 15% of the self-neutralizing AABC composition of Example 1.
  • compositions of Examples 4 and 5 comprising 15% of the self-neutralizing AABC composition were analyzed via SAXS to characterize the D-spacings of the resulting lamellar LC systems over the temperature range of 20 - 70 °C.
  • Figures 3 and 4 show SAXS data for lamellar LC systems comprising brassicyl valinate esylate and brassicyl isoleucinate esylate, respectively.
  • the peaks observed are indicative of D-spacings of 75 A (7.5 nm) and 77 A (7.7 nm) for the respective formulations. Disappearance of the peaks at temperatures exceeding 60 °C is indicative of a phase change to a nonlamellar system.
  • Example 3 The process of Example 3 was repeated using the material prepared in Comparative Example 1 in the amount specified in Table 2.
  • Example 5 Preparation of a Formulation Including the Self-Neutralizing AABC Composition
  • Example 4 The process of Example 4 was repeated using the self-neutralizing AABC composition prepared in Example 2 in the amount specified in Table 2.
  • Comparative Example 5 [0084] The process of Example 4 was repeated using the material prepared in Comparative Example 2 in the amount specified in Table 2.
  • Example 6- Preparation of a Formulation Including a Self-Neutralizing AABC Composition
  • Example 4 The process of Example 4 was repeated using the self-neutralizing AABC composition prepared in Example 3 in the amount specified in Table 2.
  • Example 4 The process of Example 4 was repeated using the material prepared in Comparative Example 3 in the amount specified in Table 2.
  • aqueous compositions comprising Examples 1, 2, and/or 3 demonstrate nearly constant pH values of 4.3 - 4.5 at concentrations ranging from 5 wt% to 20 wt% of AABC blend, whereas the comparative examples without the buffering agent
  • the self-neutralizing AABC compositions of Examples 1, 2, and 3 provide the benefit of a pH value appropriate for the formulation of composition for hair care and skin care that is independent of use level and does not require further adjustment upon compounding in aqueous media.
  • Table 3 shows the relative amounts of ingredients used in the following exemplary formulation of a hair conditioner.
  • the temperature was brought to 80 - 85 °C and the mixture was stirred for 10-15 minutes at medium-high speed. Heating was stopped and the mixture was allowed to cool to 70 °C while stirring at medium-high speed. At 70 °C, the mixture was homogenized for three minutes at high speed, and then allowed to cool to 45 to 50 °C while stirring at slow speed with an anchor-type blade. At 50 °C the mixture was discharged to an appropriate container for storage.
  • the pH of the resulting formulation was 4.20 and the Brookfield viscosity (RVT (D), helipath spindle T-C, 10 rpm) was 53,500 cP at room temperature (about 21 °C).
  • Example 8 Natural Leave-In Split End Mender
  • Table 4 shows the relative amounts of ingredients used in the following exemplary formulation of a hair spilt end mender.
  • the oil phase mixture was added to the water phase mixture at 80 °C while mixing at medium-high speed.
  • the mixture was allowed to cool to 70 °C and then homogenized at high speed for three minutes. Following homogenization, the mixture was allowed to cool to 45 - 50 °C while stirring at slow speed with an anchor-type blade. At 45 - 50 °C the mixture was discharged to an appropriate container for storage.
  • Table 5 shows the relative amounts of ingredients used in the following exemplary formulations of hair conditioner bars.
  • Examples 9 and 10 were prepared by the“melt and pour” process known to those skilled in the art.
  • the ingredients were charged to an appropriately sized beaker and heated to 80 - 85 °C while mixing at medium speed to maintain uniform dispersion of the buffering agent in the mixture.
  • the fragrance was withheld from the mixture until the final 1-2 minutes of mixing.
  • the mixture was immediately discharged to cooled bar molds and cooled rapidly to maintain a uniform, homogenous solid form.
  • the pH values of a 10% solution of the bar compositions in water were 4.09 and 5.39 for Example 9 and Example 10, respectively.
  • Table 6 shows the relative amounts of ingredients used in the formulations of therapeutic lotion formulas of Example 11 and Comparative Example 11. The elucidated viscosity and pH of each formulation are also shown in Table 6.
  • the self-neutralizing AABC of Example 3 was added along with isopropyl palmitate, petrolatum, and dimethicone.
  • the batch was mixed at medium-high speed for 10 - 15 minutes to ensure all ingredients were melted and uniformly dispersed. Heating was stopped and the batch allowed to cool to ca. 70 °C with continued mixing.
  • the batch was homogenized at 3000 rpm for three minutes and then mixing was resumed at low-medium speed while allowing to cool.
  • caprylhydroxamic acid (and) benzyl alcohol (and) glycerin were added. The mixture was allowed to cool to 40 - 45 °C while stirring at slow speed with an anchor-type blade.
  • the pH of the resulting formulation was 4.19 and the Brookfield viscosity (RVT (D), helipath spindle T-C, 10 rpm) was 12,400 cP at room temperature (about 21 °C).
  • Comparative Example 11 was prepared using Comparative Example 3, a non self- neutralizing AABC composition, according to the same process as Example 11.
  • the resulting lotion exhibited an undesirably low pH value (2.73) and an undesirably low viscosity (5,400 cP) compared to Example 11.
  • Table 7 shows the relative amounts of ingredients used in the formulations Example 12 and Comparative Example 12. The elucidated viscosity and pH of each formulation are also shown in Table 7.
  • an oil phase was prepared by combining Helianthus Annus (sunflower) seed oil, caprylic/capric triglyceride, and isopropyl palmitate. The mixture was heated to 75 - 80 °C while mixing at low-medium speed. While heating, the self neutralizing AABC composition of Example 3 was added and the oil phase mixed until uniform.
  • the oil phase was held at 75 - 80 °C with mixing to maintain a uniform dispersion without sedimentation.
  • a separate beaker equipped with equipped with overhead mechanical stirrer and propeller blade and hotplate for heating, water and caprylhydroxamic acid (and) glyceryl caprylate (and) glycerin were combined and heated to 75 - 80 °C while mixing at low- medium speed.
  • mixing speed was increased to medium-high and the hot oil phase was added to the main batch and allowed to mix at 75 - 80 °C until uniform.
  • Comparative Examples 12 was prepared using Comparative Example 3, a nonself neutralizing AABC composition, according to the same process as Example 12. The resulting cream exhibited an undesirably low pH value (2.55) and an undesirably low viscosity (21,800 cP) compared to Example 12.
  • Example 13 was prepared according to the same general procedure described in Example 12. Citrus Aurantium Dulcis (orange) peel oil and fragrance were post-added to the batch during the cooling period when the temperature had cooled to ⁇ 55 °C. The pH of the resulting formulation was 4.03 and the Brookfield viscosity (RVT (D), helipath spindle T-C, 10 rpm) was 50,400 cP at room temperature (about 21 °C). [00122] Table 8 shows the ingredients and their relative amounts as used for Example 13.

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EP20766131.5A EP3934638A4 (en) 2019-03-07 2020-03-09 SELF-NEUTRALIZING AMINO ACID BASED CATIONIC COMPOSITIONS
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CA3132043A CA3132043C (en) 2019-03-07 2020-03-09 Self-neutralizing amino-acid based cationic compositions
CN202080019230.6A CN113677337B (zh) 2019-03-07 2020-03-09 基于自中和氨基酸的阳离子组合物
KR1020217032061A KR102613882B1 (ko) 2019-03-07 2020-03-09 자가 중화 아미노산 기반 양이온성 조성물
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BR112021017173-8A BR112021017173B1 (pt) 2019-03-07 2020-03-09 Composições catiônicas à base de aminoácidos autonutralizantes e formulação aquosa
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US8105569B2 (en) * 2009-06-29 2012-01-31 Inolex Investment Corporation Non-petrochemically derived cationic emulsifiers that are neutralized amino acid esters and related compositions and methods
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