WO2023078108A1 - Procédé d'amélioration de la stabilité de la p-hydroxyacétophénone dans une composition cosmétique - Google Patents

Procédé d'amélioration de la stabilité de la p-hydroxyacétophénone dans une composition cosmétique Download PDF

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Publication number
WO2023078108A1
WO2023078108A1 PCT/CN2022/126884 CN2022126884W WO2023078108A1 WO 2023078108 A1 WO2023078108 A1 WO 2023078108A1 CN 2022126884 W CN2022126884 W CN 2022126884W WO 2023078108 A1 WO2023078108 A1 WO 2023078108A1
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acid
cosmetic composition
hydroxyacetophenone
salts
mixture
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PCT/CN2022/126884
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English (en)
Chinese (zh)
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赵仕芝
娄菲
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养生堂（上海）化妆品研发有限公司
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Publication of WO2023078108A1 publication Critical patent/WO2023078108A1/fr

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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
    • A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/35—Ketones, e.g. benzophenone
    • 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
    • A61K8/19—Cosmetics or similar toiletry preparations characterised by the composition containing inorganic ingredients
    • A61K8/24—Phosphorous; Compounds 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
    • A61K8/30—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
    • A61K8/442—Aminocarboxylic acids or derivatives thereof, e.g. aminocarboxylic acids containing sulfur; Salts; Esters or N-acylated derivatives thereof substituted by amido group(s)
    • 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
    • A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
    • A61K8/4973—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with oxygen as the only hetero atom
    • A61K8/498—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with oxygen as the only hetero atom having 6-membered rings or their condensed derivatives, e.g. coumarin
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q1/00—Make-up preparations; Body powders; Preparations for removing make-up
    • A61Q1/02—Preparations containing skin colorants, e.g. pigments
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q17/00—Barrier preparations; Preparations brought into direct contact with the skin for affording protection against external influences, e.g. sunlight, X-rays or other harmful rays, corrosive materials, bacteria or insect stings
    • A61Q17/04—Topical preparations for affording protection against sunlight or other radiation; Topical sun tanning preparations
    • 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
    • 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
    • A61K2800/52—Stabilizers
    • A61K2800/524—Preservatives

Definitions

  • the present invention relates to a method for improving the stability of p-hydroxyacetophenone in a cosmetic composition, which comprises adding a pH stabilizer to a cosmetic composition containing p-hydroxyacetophenone, so that the pH of the composition Maintaining stability, thereby improving the stability of the p-hydroxyacetophenone in the cosmetic composition, which significantly alleviates the problem of discoloration (yellowing) of the cosmetic composition caused by the instability of the p-hydroxyacetophenone.
  • the pH stabilizer is a substance known in the art that can keep the pH of the cosmetic composition stable, including, for example, a pH buffer pair, a reagent that can slowly release acid through hydrolysis to keep the pH of the cosmetic composition stable, or a mixture of them.
  • 4-Hydroxyacetophenone is a natural plant extract, which naturally exists in the stems and leaves of Artemisia spp. Off-white flaky solid, the molecular formula is C 8 H 8 O 2 , and the structure is as follows:
  • p-Hydroxyacetophenone has the functions of clearing dampness and heat, promoting choleresis and reducing jaundice, and has good curative effect and auxiliary curative effect on eyeball yellowing caused by hepatitis and other diseases, so it is often used in the preparation of choleretic drugs.
  • p-Hydroxyacetophenone also has multiple functions such as anti-oxidation, anti-irritation and antibacterial properties, and is often used as a preservative synergist in cosmetics.
  • hydroxyl which is effective against fungi, has a strong ability to kill Aspergillus niger, and has a certain inhibitory effect on Pseudomonas aeruginosa.
  • p-hydroxyacetophenone is mild and safe, and has good compatibility with cosmetics, so its usage in cosmetics is increasing year by year.
  • p-hydroxyacetophenone When p-hydroxyacetophenone is used in cosmetics, it is usually heated and dissolved in alcohol solution, and then dissolved in water.
  • p-hydroxyacetophenone is unstable in an alcohol solution or an aqueous solution even at normal temperature, causing problems of discoloration of the solution and simultaneous upward drift of pH.
  • this instability phenomenon will be more significant, becoming a major problem in its application in cosmetics.
  • Figure 1 is a photograph of the appearance of compositions A-I initially and after 4 weeks of storage under various conditions.
  • Figure 2 is a photograph of the appearance of compositions N and O initially and after 4 weeks of storage under various conditions.
  • Figure 3 is a photograph of the appearance of compositions J-M initially and after 4 weeks of storage under various conditions.
  • the inventors have found through research that the use of pH stabilizers can improve the stability of p-hydroxyacetophenone in cosmetic compositions, thereby significantly alleviating the yellowing of cosmetic compositions caused by the instability of p-hydroxyacetophenone.
  • the present invention provides a method for improving the stability of p-hydroxyacetophenone in a cosmetic composition, which includes adding a pH stabilizer to a cosmetic composition containing p-hydroxyacetophenone, so that The pH of the composition remains stable throughout its shelf life (typically 3 years), and the method of the present invention does not cause significant pH changes in the cosmetic composition even when exposed to light or high temperature for a considerable period of time. Drift upwards.
  • the present invention relates to the use of a pH stabilizer for increasing the stability of para-hydroxyacetophenone in a cosmetic composition comprising para-hydroxyacetophenone.
  • the present invention provides a stable cosmetic composition comprising p-hydroxyacetophenone and a pH stabilizer that does not change over time throughout its shelf life (typically 3 years). yellow.
  • the pH stabilizer is a substance known in the art that can keep the pH of the cosmetic composition stable so as to avoid the pH of the composition system from drifting significantly with prolonged storage time, for example, a pH buffer pair, which can slowly release acid through hydrolysis Agents that thereby stabilize the pH of the cosmetic composition (abbreviated as "agents that slowly release acid by hydrolysis”).
  • the pH buffer pairs are those known in the art, including mixtures of weak acids and their salts. Described weak acid includes organic acid and inorganic acid, and organic acid includes such as acetic acid, levulinic acid, citric acid, lactic acid, phthalic acid etc., and inorganic acid includes such as carbonic acid, phosphoric acid, metaphosphoric acid, sulfurous acid, hydrofluoric acid, hydrogen Sulfuric acid, hypochlorous acid, etc.
  • the salt may be an alkali metal salt, for example, sodium salt, potassium salt.
  • Preferred examples of pH buffer pairs include, for example, levulinic acid-sodium levulinate, citric acid-sodium/potassium citrate, and lactic acid-sodium/potassium lactate, and the like.
  • the pH buffer pair can also be acid salts of polybasic weak acids and their corresponding secondary salts, including, for example, sodium dihydrogen phosphate-disodium hydrogen phosphate, sodium bicarbonate-sodium carbonate, and sodium dihydrogen citrate-lemon Disodium hydrogen acid, etc.
  • the molar ratio of the weak acid to its salt is about 0.5:1.0-3.0:1.0, preferably about 1:1
  • the molar ratio of the acid salt of the polybasic weak acid to its corresponding secondary salt is about 0.5:1.0-3.0:1.0, Preferably about 1:1.
  • the agents that can slowly release acid through hydrolysis to stabilize the pH of the cosmetic composition are those known in the art, including, for example, small molecule lactones and/or esters. Specific examples include, for example, gluconolactone, ⁇ -nonanolactone, pantolactone, glucoheptonolactone, triethyl citrate and the like.
  • each of the above-mentioned pH buffer pairs and each of the above-mentioned reagents that can slowly release acid through hydrolysis can be used alone or in combination.
  • the pH stabilizer is present in the cosmetic composition in such an amount that the pH of the cosmetic composition does not experience significant upward drift throughout the shelf life (typically 3 years).
  • the content of the pH stabilizer in the cosmetic composition is about 0.01-3%, preferably about 0.05-2%, more preferably about 0.1-1%, based on the total weight of the cosmetic composition.
  • the pH of cosmetic compositions is generally about 4-7, preferably about 5-7.
  • the pH of the cosmetic composition can be stabilized within the above range throughout the shelf life by using a pH stabilizer.
  • the shelf life of the cosmetic composition at normal temperature ie, room temperature, usually about 20-25° C. is about 3 years.
  • the pH of the cosmetic composition remains stable for a substantial period of time, for example under accelerated conditions of about 48°C and about 60°C, the pH of the cosmetic composition remains stable for 4 weeks without significant discoloration, as shown in the examples below .
  • the content of p-hydroxyacetophenone is usually about 0.01-1%, preferably about 0.05-0.8%, more preferably about 0.1-0.6%, based on the cosmetic composition gross weight.
  • Cosmetic compositions containing p-hydroxyacetophenone, in addition to p-hydroxyacetophenone and a pH stabilizer optionally include various ingredients commonly used in cosmetics, including active ingredients, vehicles, surfactants and adjuvants These are known to those skilled in the art, and their types and amounts can be specifically selected according to needs.
  • the vehicle can be a diluent, a dispersant or a carrier, etc. All vehicles are known in the art, and those skilled in the art can select their type and dosage according to needs, including but not limited to ethanol, dipropylene glycol, Propylene glycol, butylene glycol, pentylene glycol, etc.; in the compositions of the present invention, said vehicle constitutes about 1-20% of the total weight of said commonly used ingredients.
  • Such active ingredients include, for example, emollients, moisturizers, skin conditioners, and the like.
  • emollients include, but are not limited to, triglycerides (ethylhexanoate), caprylic/capric triglycerides, shea butter, cetyl alcohol, dimethicone, pentaerythritol tetra(ethylhexyl) Acid) Esters, Olive Oil, Grape Seed Oil, White Pond Seed Oil, avocado Oil, Corn Oil, Squalane, Dioctyl Carbonate, Isopropyl Myristate, Hydrogenated Polydecene, Sunflower Seed Oil, Isodeca One or more of hexane, jojoba seed oil, lanolin, paraffin, microcrystalline wax, beeswax, etc.; in the cosmetic composition of the present invention, the emollient accounts for the total weight of the commonly used ingredients 0-50%.
  • humectants include, but are not limited to, birch sap, glycerin, betaine, glyceryl-26, trehalose, sucrose, propylene glycol, 1,2-pentanediol, mannitol, rhamnose, raffinose, erythritol Britol, Xylitol, Urea, Macrogol-8, Macrogol-32, Methyl Gluceth-10, Methyl Gluceth-20, PEG/PPG-17/6 Copolymer, sodium polyglutamate, hydrolyzed sclerotin, pullulanase polysaccharide, tremella polysaccharide, sodium polyglutamate, glycerol glucoside, PPG-10 methyl glucose ether, PPG-20 methyl glucose One or more of ethers, etc.; in the cosmetic composition of the present invention, the moisturizing agent accounts for about 0.1-30% of the total weight of the commonly used ingredients.
  • Such skin conditioners include, but are not limited to, phytosterol/octyldodecanol lauroyl glutamate, hydrolyzed sodium hyaluronate, acetyl phytosphingosine, turmeric root extract, ceramide 2, ceramide 3, choleramide Sterols, kojic acid, ascorbic acid, ascorbyl glucoside, arbutin, tranexamic acid, niacinamide, birch bark extract, acetyl phytosphingosine, resveratrol, flower palm bark extract, forskolin Pistil flower root extract, pepper seed extract, ubiquinone, bisabolol, ascorbyl tetraisopalmitate, pyridoxine dicaprylate, pyridoxine dipalmitate, retinyl palmitate, etc.
  • the skin conditioning agent can be used for moisturizing, anti-wrinkle, freckle, acne, oil control and other effects, usually, in the cosmetic composition of the present invention, the skin conditioning agent accounts for about 0-50% of the total weight of the commonly used ingredients. %.
  • the surfactant may be any type of surfactant commonly used in cosmetics. It is used to reduce the surface tension of the interface to achieve the purpose of cleaning, emulsifying and stabilizing the system. It can be any type of surfactant commonly used in cosmetics. Those skilled in the art can choose its type and dosage according to needs.
  • the surfactant may include, but is not limited to, fatty acid soaps (such as sodium laurate, sodium palmitate, etc.), higher alkyl sulfates (such as sodium lauryl sulfate, etc.), N-acyl sarcosine (such as lauroyl sodium sarcosinate, etc.), higher fatty acid amide sulfonates (such as sodium lauryl methyl taurate, etc.), alkylbenzene sulfonates, higher fatty acid ester sulfates (such as hardened coconut oil fatty acid sodium glycerol sulfate, etc.) , N-acyl glutamate, betaine lauryldimethylaminoacetate, alkyl betaine, amido betaine, sorbitan fatty acid esters (e.g., sorbitan monooleate, sorbitan Alcohol monoisostearate, sorbitan monolaurate, sorbitan monopalmitate, sorb
  • the auxiliary materials include but are not limited to surfactants, emulsifiers, thickeners, preservatives, spices, pH regulators and the like.
  • emulsifiers include but are not limited to: PEG-60 hydrogenated castor oil, glyceryl stearate/PEG-100 stearate, sorbitan olive oil ester, steareth-21, PPG-13-decane Myristyl Tetraeth-24, Cetearyl Glucoside, Cetearyl Glucoside, Polyglyceryl-10 Stearate, Polyglyceryl-10 Myristate, Polyglyceryl-10 Dioleate One or more of esters, etc.; generally, in the cosmetic composition of the present invention, the emulsifier accounts for about 0-10% of the total weight of the commonly used ingredients.
  • the thickener includes but not limited to: carbomer, xanthan gum, SIMUGEL EG, gum arabic, polyethylene glycol-14M, polyethylene glycol-90M, succinoglycan, hydroxyethyl cellulose, hydroxy One or more of propyl cellulose, etc.; generally, in the composition of the present invention, the thickener accounts for about 0-10% of the total weight of the commonly used ingredients.
  • preservatives that can be used in the present invention, which are known in the art, including but not limited to methylparaben, propylparaben, phenoxyethanol, benzyl alcohol, phenylethyl alcohol, potassium sorbate, sodium benzoate
  • preservative synergists such as common preservatives such as pentylene glycol, hexylene glycol, caprylyl glycol; usually, in the composition of the present invention, the preservative About 0.01-2% of the total weight of the usual ingredients.
  • pH regulators that can be used in the present invention, which are known in the art, including but not limited to: one or more of citric acid, sodium citrate, arginine and the like. Those skilled in the art can specifically select its type and dosage according to needs.
  • Cosmetic compositions of the present invention may be prepared by any suitable method known in the art.
  • it can be prepared using containers such as dissolution tanks, emulsification pots, dispersers, and delivery pumps commonly used in the field of cosmetics.
  • containers such as dissolution tanks, emulsification pots, dispersers, and delivery pumps commonly used in the field of cosmetics.
  • When preparing first put the water-soluble substances into the water-phase dissolving kettle, put the oil-soluble substances into the oil-phase dissolving kettle, and heat the temperature of the two kettles to about 80°C respectively.
  • you can first use a disperser It is pre-dispersed. After the dissolution is complete, transfer the oil phase and water phase to the emulsification pot, and emulsify homogeneously for about 5-15 minutes.
  • the temperature of the material body is lowered to normal temperature, optional flavors, preservatives, etc. are added, and the pH of the product is adjusted as needed. Only after the relevant testing indicators are qualified can it be filled and shipped.
  • the above preparation methods can be deleted or adjusted according to the dosage form requirements, and various dosage forms such as water, emulsion, ointment, cream or gel can be prepared as required.
  • Example 1 Preparation and investigation of pH stability and color stability of cosmetic compositions A (no pH stabilizer added) and B-H (with different and/or different concentrations of pH stabilizer added) containing p-hydroxyacetophenone sex
  • compositions A-I are shown in Table 1 below.
  • levulinic acid (50% aqueous solution) comes from the supplier Shumei; sodium levulinate (powder) is purchased from Wuhan Lanabai Pharmaceutical Chemical.
  • Gluconolactone is sourced from the supplier Knaeo.
  • Disodium hydrogen phosphate and sodium dihydrogen phosphate are from Aladdin Biotechnology.
  • each cosmetic composition was subpackaged and placed at room temperature, window sill, light (25°C, visible light intensity 16000LX), high temperature (48°C and 60°C) for 2 and 4 weeks, respectively, to investigate the pH changes and The color change and the appearance after 4 weeks were photographed.
  • the results are shown in Table 2 below.
  • Embodiment 2 investigate pH stability and color stability of cosmetic composition N (add pH stabilizer) and cosmetic composition I (add antioxidant)
  • Example 3 Prepare and investigate the influence of different pH stabilizers on the pH stability and color stability of the cosmetic composition J-M containing p-hydroxyacetophenone
  • the technical scheme of the above-described embodiment is a preferred embodiment of the present invention.
  • the pH stabilizer of the present invention can be applied to various cosmetics such as essence, milk, cream, foundation, sunscreen and the like added with p-hydroxyacetophenone
  • the improvement of the color stability can also be improved and changed without departing from the principle of the present invention, and these improvements and changes should also be considered within the protection scope of the present invention.

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Abstract

L'invention concerne un procédé d'amélioration de la stabilité de la p-hydroxyacétophénone dans une composition cosmétique, comprenant : l'ajout d'un stabilisateur de pH à une composition cosmétique contenant de la p-hydroxyacétophénone de telle sorte que le pH de la composition est maintenu stable, ce qui permet d'améliorer la stabilité de la p-hydroxyacétophénone dans la composition cosmétique, et d'atténuer le problème de la décoloration ou du jaunissement de la composition cosmétique du fait de l'instabilité de la p-hydroxyacétophénone.
PCT/CN2022/126884 2021-11-05 2022-10-24 Procédé d'amélioration de la stabilité de la p-hydroxyacétophénone dans une composition cosmétique WO2023078108A1 (fr)

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CN202111305348.8A CN114010519A (zh) 2021-11-05 2021-11-05 一种提高对羟基苯乙酮在化妆品组合物中的稳定性的方法
CN202111305348.8 2021-11-05

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CN114010519A (zh) * 2021-11-05 2022-02-08 养生堂（上海）化妆品研发有限公司 一种提高对羟基苯乙酮在化妆品组合物中的稳定性的方法
CN115569088B (zh) * 2022-09-20 2024-05-31 上海肌本颜究生物科技发展有限公司 一种化妆品用预处理组合物及其制备方法和应用

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