WO2021034150A1 - 공융 혼합물을 포함하는 화장료 조성물 - Google Patents

공융 혼합물을 포함하는 화장료 조성물 Download PDF

Info

Publication number
WO2021034150A1
WO2021034150A1 PCT/KR2020/011202 KR2020011202W WO2021034150A1 WO 2021034150 A1 WO2021034150 A1 WO 2021034150A1 KR 2020011202 W KR2020011202 W KR 2020011202W WO 2021034150 A1 WO2021034150 A1 WO 2021034150A1
Authority
WO
WIPO (PCT)
Prior art keywords
eutectic mixture
cosmetic composition
parts
weight
acid
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Ceased
Application number
PCT/KR2020/011202
Other languages
English (en)
French (fr)
Korean (ko)
Inventor
권구철
권태근
박상욱
이소영
서지현
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
LG H&H Co Ltd
Original Assignee
LG Household and Health Care Ltd
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by LG Household and Health Care Ltd filed Critical LG Household and Health Care Ltd
Priority to CN202410327676.5A priority Critical patent/CN118217176A/zh
Priority to CN202410327679.9A priority patent/CN118217177A/zh
Priority to EP25189565.2A priority patent/EP4623891A3/en
Priority to US17/636,753 priority patent/US20220287938A1/en
Priority to EP20854144.1A priority patent/EP4018996B1/en
Priority to CN202080073446.0A priority patent/CN114555043B/zh
Priority to JP2022511298A priority patent/JP7601858B2/ja
Publication of WO2021034150A1 publication Critical patent/WO2021034150A1/ko
Anticipated expiration legal-status Critical
Priority to JP2024211600A priority patent/JP7842181B6/ja
Ceased legal-status Critical Current

Links

Images

Classifications

    • 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
    • A61K8/18—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
    • A61K8/02—Cosmetics or similar toiletry preparations characterised by special physical form
    • A61K8/0204—Specific forms not provided for by any of groups A61K8/0208 - A61K8/14
    • 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
    • A61K8/40—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
    • A61K8/447—Aminocarboxylic acids or derivatives thereof, e.g. aminocarboxylic acids containing sulfur; Salts; Esters or N-acylated derivatives thereof containing sulfur
    • 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
    • A61K8/4906—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with one nitrogen as the only hetero atom
    • A61K8/4913—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with one nitrogen as the only hetero atom having five membered rings, e.g. pyrrolidone carboxylic acid
    • 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
    • A61K8/4906—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with one nitrogen as the only hetero atom
    • A61K8/4913—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with one nitrogen as the only hetero atom having five membered rings, e.g. pyrrolidone carboxylic acid
    • A61K8/492—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with one nitrogen as the only hetero atom having five membered rings, e.g. pyrrolidone carboxylic acid having condensed rings, e.g. indol
    • 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
    • A61K8/494—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with more than one nitrogen as the only hetero atom
    • A61K8/4946—Imidazoles or their condensed derivatives, e.g. benzimidazoles
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P17/00—Drugs for dermatological disorders
    • A61P17/10—Anti-acne agents
    • 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
    • A61Q19/00—Preparations for care of the skin
    • A61Q19/08—Anti-ageing 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
    • A61Q19/10—Washing or bathing 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
    • A61K2800/28—Rubbing or scrubbing compositions; Peeling or abrasive compositions; Containing exfoliants
    • 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
    • A61K2800/59—Mixtures
    • A61K2800/592—Mixtures of compounds complementing their respective functions
    • A61K2800/5922—At least two compounds being classified in the same subclass of A61K8/18

Definitions

  • the present invention is a cosmetic composition
  • a cosmetic composition comprising a eutectic mixture containing alpha-hydroxy acid, amino acid and purified water; And a eutectic mixture containing a first amino acid and a second amino acid, and more particularly, a eutectic mixture of purified water, an amino acid and an alpha-hydroxy acid, or a eutectic mixture of a first amino acid and a second amino acid
  • a cosmetic composition that has excellent skin permeability and exfoliation effect and low temperature stability even under a pH condition with little irritation on the skin, and maintains the exfoliation effect even under severe conditions.
  • Alpha-hydroxy acid (hereinafter referred to as AHA) is one of the ingredients commonly used to soften or remove the hyperkeratinized skin layer, promoting keratin turnover, collagen synthesis, and skin moisturization. , Relieving fine wrinkles, treatment and prevention of acne, etc. (Korean Wellness Journal Vol. 10, No. 2, 2015, 161-169).
  • Most AHAs are excellent in skin permeability and skin improvement effect under low pH conditions, but due to low pH, skin irritation such as itching, tingling, and burning and various inflammatory irritation such as erythema and swelling are severe. It is difficult.
  • AHA has a disadvantage in that it is ionized when dissolved in water, which slows skin absorption.
  • AHA when formulated as a cosmetic, the pH of the formulation is lowered, resulting in lower formulation stability and may have a negative effect on the skin such as irritation. To compensate for this, if the pH of the formulation is increased with a neutralizing agent, there is a problem that the effect of AHA decreases.
  • amino acids that exhibit exfoliating effect on dry skin along with the AHA are also widely used in skin-applied cosmetics (Tatsuya Ozawa et al., The role of humectants in skin moisture retention. Skin Research 27, 276-288 (1985) ; And KR Patent No. 10-1508168).
  • the AHA and amino acids significantly decrease skin permeability at weak acidic or neutral pH.
  • it can cause discomfort, such as skin irritation, especially in people with sensitive skin.
  • eutectic phenomenon is a phenomenon in which the melting point decreases as two or more substances are mixed.
  • Each component in the mixture exhibits a solid state at room temperature, but when prepared as a mixture, van der Waals interactions between the components Or it becomes an anhydrous solution that does not crystallize due to hydrogen bonding and exists as a liquid at room temperature.
  • AHA is selected as one of the components included in the mixture, a liquid phase in which water is removed can be obtained.
  • AHA since AHA is not ionized, it does not exhibit the properties of acid, so it is possible to use AHA with little stimulation, and it is very advantageous for skin penetration because AHA is not charged.
  • this eutectic mixture has a problem that it does not stably exist in cosmetics.
  • a protic solvent capable of hydrogen bonding is added to the composition containing the eutectic mixture, the solvent interacts (hydrogen bonds) with each component of the eutectic mixture, thereby interfering with the bonding between the components of the eutectic mixture. It is difficult to maintain the properties of the mixture.
  • the anhydrous formulation is suitable for cosmetics containing eutectic mixtures, but the specific gravity of most eutectic mixtures is greater than water, so precipitation occurs when mixing with oil, making it difficult to evenly disperse on low viscosity oil.
  • the present inventors believe that the eutectic mixture is purified water, AHA and amino acids;
  • the present invention was completed by researching and developing a cosmetic composition containing two kinds of amino acids and improving the irritation problem and formulation stability due to low pH.
  • the present inventors have studied to develop a cosmetic composition that has improved the problem that AHA irritates at a low pH and has a low skin permeation effect when AHA or amino acids are applied at the skin pH.
  • the cosmetic composition contains purified water, AHA and amino acid; Two kinds of amino acids;
  • purified water and two kinds of amino acids in the form of a eutectic mixture, the skin permeability of AHA or amino acids can be improved without skin irritation at weakly acidic to neutral pH, and amino acids are not precipitated even at low temperatures and can be maintained stably and uniformly.
  • the exfoliation effect can be maintained even under severe conditions (eg, high temperature, high pressure, etc.), and the present invention was completed.
  • an object of the present invention is purified water, AHA and amino acids; Two kinds of amino acids; Alternatively, a cosmetic composition containing purified water and two kinds of amino acids in the form of a eutectic mixture in the cosmetic composition to provide excellent exfoliation effect even under weakly acidic to neutral conditions, low irritation, excellent low-temperature stability, and maintaining the exfoliating effect even under severe conditions. To provide.
  • the cosmetic composition of the present invention As a means for solving the above problems, the cosmetic composition of the present invention
  • Purified water, amino acids, and alpha-hydroxy acids (AHA); Or it provides a cosmetic composition comprising a eutectic mixture containing the first amino acid and the second amino acid.
  • the cosmetic composition of the present invention is purified water; amino acid; And a eutectic mixture containing alpha-hydroxy acid (hereinafter referred to as AHA).
  • the alpha-hydroxy acid (AHA) and amino acids may be included in the eutectic mixture as a use for skin improvement effects such as promoting exfoliation of skin, improving pores, improving fine wrinkles, improving acne or improving facial skin tone, respectively. have.
  • the alpha-hydroxy acid is a generic term for a compound in which an alcohol group or a hydroxyl group is added to the carbon at the ⁇ -position of a carboxylic acid, and the ionic binding energy of keratinocytes is It acts to improve skin by promoting skin cell activity by lowering it to remove hyperkeratin or by promoting the formation of new cells and shortening the cycle of the keratinization process that lengthens as the skin ages.
  • AHA promotes the production of collagen and elastin by fibroblasts to make the skin elastic and soft, and promotes skin moisturization by promoting the production of mucopolysaccharide, an important extracellular matrix component of the dermis. I can make it.
  • AHA helps to remove the link between the dead skin cells in the stratum corneum by the action of acids, and has the effect of gently dissolving the dead skin cells.
  • the AHA is lactic acid contained in sweetened milk or tomato juice; Citric acid contained in tangerines and oranges; Malic acid contained in apples and the like; Tartaric acid contained in wine, etc.; It may be at least one selected from the group consisting of glycolic acid and mandelic acid contained in sugar cane, but is not limited thereto.
  • the AHA may be lactic acid or malic acid.
  • the lactic acid has a fast skin penetration due to its low molecular weight among AHAs, so it can quickly realize the desired AHA effect
  • malic acid has a plurality of carboxyl groups in preparing a eutectic mixture, so that it binds stronger. It can induce and its molecular structure is similar to that of amino acids, especially serine, and thus can exhibit an advantageous advantage in preparing a structurally stable dimer or a eutectic mixture in the form of a multimer.
  • the AHA when AHA is contained in the eutectic mixture, the AHA is 1 to 50 parts by weight, such as 5 to 40 parts by weight, 10 to 30 parts by weight, 15 to 20 parts by weight based on 100 parts by weight of the eutectic mixture. It may be included in parts, 3 to 25 parts by weight, 5 to 20 parts by weight, and 6 to 18 parts by weight. If less than 1 part by weight of AHA is contained in the eutectic mixture, the desired effect cannot be exhibited, and if it is contained in more than 50 parts by weight, a problem of irritation to the skin may occur.
  • the eutectic mixture is mixed with an amino acid, which is a component that can be bonded to the AHA and polar intermolecular dipole-dipole attraction, dipole-induced dipole attraction, hydrogen bond or van der Waals interaction. Can be manufactured.
  • the AHA acts as a hydrogen bond donor (HBD)
  • the amino acid may act as a hydrogen bond acceptor (HBA).
  • the amino acids include alanine, cysteine, aspartic acid, glutamic acid, phenylalanine, glycine, histidine, and isoleucine.
  • lysine leucine, methionine, asparagine, pyrrolysine, proline, glutamine, arginine, serine, threonine (threonine), selenocysteine, valine, tryptophan, or tyrosine.
  • the total content of amino acids in the eutectic mixture is 1 to 75 parts by weight, 5 to 70 parts by weight, 10 to 60 parts by weight, 15 to 50 parts by weight, 20 to 47 parts by weight, based on 100 parts by weight of the total eutectic mixture. , 10 to 70 parts by weight, 20 to 65 parts by weight, 30 to 60 parts by weight, 35 to 55 parts by weight, 40 to 50 parts by weight, 42 to 47 parts by weight, but are not limited thereto.
  • the amino acid included in the eutectic mixture may be serine, proline, threonine, arginine or cysteine.
  • the eutectic mixture may be prepared from AHA and amino acids, preferably from purified water, AHA and amino acids.
  • the AHA and amino acid are in a eutectic mixture in a weight ratio of 1:0.1 to 1:10, such as a weight ratio of 1:0.3 to 1:5, a weight ratio of 1:0.5 to 1:3, and 1:0.7 to 1: It may be included in a weight ratio of 2, a weight ratio of 1:3 to 1:10, and a weight ratio of 1:5 to 1:8.
  • the eutectic mixture according to the present invention is not ionized even in the presence of purified water through a dipole-dipole attraction, a dipole-induced dipole attraction, hydrogen bonding or van der Waals interaction of AHA and amino acids. Can be safe from negative effects such as an increase in
  • the eutectic mixture according to the present invention contains purified water.
  • the eutectic mixture of the present invention has a low melting point of 0° C. or less by purified water including purified water, and can stably maintain amino acids in the composition.
  • purified water is included in the eutectic mixture, AHA and amino acids are gradually dissociated due to exposure to excess moisture, thereby improving skin improvement effect by promoting keratin peeling. Accordingly, the eutectic mixture of the present invention can uniformly and stably maintain a liquid phase without precipitation of amino acids even in various environmental changes.
  • the purified water may be included in an amount of 25 to 80 parts by weight based on 100 parts by weight of the total eutectic mixture.
  • the content of purified water in the eutectic mixture is less than 25 parts by weight, the melting point of the eutectic mixture cannot be reduced and amino acids cannot be stably present, and when the content exceeds 80 parts by weight, AHA and amino acids due to inhibition of the stability of hydrogen bonding It may be difficult to achieve the desired effect due to a decrease in skin permeability and a lower content of amino acids.
  • the eutectic mixture of the present invention may include 30 to 75 parts by weight, 35 to 70 parts by weight, 40 to 65 parts by weight, 50 to 55 parts by weight of purified water based on the total weight of the eutectic mixture, but is limited thereto. no.
  • the cosmetic composition of the present invention comprises a eutectic mixture containing a first amino acid and a second amino acid.
  • the first and second amino acids are alanine, cysteine, aspartic acid, glutamic acid, phenylalanine, glycine, and histidine.
  • the first amino acid and the second amino acid may be two selected from the group consisting of serine, arginine and glutamic acid.
  • the total content of amino acids in the eutectic mixture is 1 to 75 parts by weight, 5 to 70 parts by weight, 10 to 60 parts by weight, 15 to 50 parts by weight, 20 to 47 parts by weight, based on 100 parts by weight of the total eutectic mixture.
  • Parts, 10 to 70 parts by weight, 20 to 65 parts by weight, 30 to 60 parts by weight, 35 to 55 parts by weight, 40 to 50 parts by weight, 42 to 47 parts by weight but are not limited thereto.
  • the first amino acid may be included in an amount of 1 to 50 parts by weight, based on 100 parts by weight of the total eutectic mixture, and the second amino acid may be included in an amount excluding a part by weight of the first amino acid from 75 parts by weight.
  • the second amino acid may be 1 to 25 parts by weight.
  • the first amino acid may be 1 to 50 parts by weight, preferably 5 to 40 parts by weight, 10 to 35 parts by weight, and 15 to 30 parts by weight.
  • the eutectic mixture of the present invention may further contain purified water.
  • the purified water may be included in an amount of 25 to 80 parts by weight, based on 100 parts by weight of the total eutectic mixture. Purified water contained in the eutectic mixture can be applied as described above.
  • the eutectic mixture may be prepared from the first amino acid and the second amino acid, preferably purified water, the first amino acid and the second amino acid.
  • a eutectic mixture comprising purified water, a first amino acid, and a second amino acid as described above, based on 100 parts by weight of the total eutectic mixture, purified water 25 to 80 parts by weight, the first amino acid 1 to 50 parts by weight, and the second amino acid 1 to It may be included in 25 parts by weight.
  • the eutectic mixture consisting of two kinds of amino acids exhibited skin improvement effects such as reduction in the number of pores, improvement of wrinkles, promotion of skin regeneration, increase in the total amount of collagen, and enhancement of skin elasticity, and under severe conditions such as high temperature. It was confirmed that the skin improvement effect as described above was maintained even after storage. In addition, it was confirmed that the eutectic mixture containing no AHA and containing only two kinds of amino acids and purified water exhibited excellent skin permeability, exfoliation effect, low temperature stability, etc. even under weakly acidic or neutral acidity conditions.
  • eutectic mixture refers to a mixture of two or more solid or liquid substances, and two components having a high melting point are mixed to form a polar intermolecular dipole-dipole attraction, a dipole-induced dipole attraction, hydrogen bonds or semi-molecules.
  • the two components form a complex by the Derwals interaction.
  • the composite formed as described above has a lower melting point than the component having the lowest melting point among the components by interfering with the ability of each component to crystallize, that is, the ability to return to a solid state, thereby exhibiting a liquid state at room temperature. .
  • the eutectic mixture contains purified water, the lowest melting point is formed below zero, so that it is possible to maintain a stable form of the composition even in various environments.
  • the eutectic mixture may be combined with polar compounds to form a eutectic mixture.
  • the compound having the polarity may be a polar molecule or a charged molecule.
  • the pKa or pI value between the components constituting the eutectic mixture may have a difference of 1.0 or more, 2.0 or more, 3.0 or more, 4.0 or more, 5.0 or more, 6.0 or more, or 7.0 or more. In this case, when a component constituting the eutectic mixture is a component having several pKa values, it may be selected based on the pKa1 value.
  • the compound having polarity may be selected from AHA or amino acids (AA). More specifically, when one of the components constituting the eutectic mixture is AHA, the other compound may select an amino acid having a higher pI than the pKa1 value of this AHA. For example, the difference between the pKa1 value and the pI value between AHA and amino acids forming the eutectic mixture may be 1.0 or more, 2.0 or more, 3.0 or more, 4.0 or more, 5.0 or more, 6.0 or more, or 7.0 or more. More specifically, when one of the components constituting the eutectic mixture is an amino acid, the other compound may select an amino acid having a pI higher or lower than the pI value of the amino acid. For example, the difference between the pI values of the two amino acids forming the eutectic mixture may be 1.0 or more, 2.0 or more, 3.0 or more, 4.0 or more, 5.0 or more, 6.0 or more, or 7.0 or more.
  • the compound having polarity may be selected from polar amino acids (polar AA), positively charged amino acids (+ charged AA) and negatively charged amino acids (-charged AA).
  • polar AA polar amino acids
  • positively charged amino acids (+ charged AA) positively charged amino acids
  • -charged AA negatively charged amino acids
  • the ratio between substances required for the eutectic mixture may be determined according to the charge of the molecules of the components constituting the eutectic mixture, the type and number of functional groups of the molecule, and the polarity of the molecule or functional group.
  • the ratio between substances required for the eutectic mixture may be determined according to the size or similarity of the molecules. For example, arginine and glutamic acid, arginine and aspartic acid, lysine and glutamic acid, lysine and aspartic acid, arginine and asparagine, and arginine and glutamine may form a eutectic mixture in a molar ratio of 1:1.
  • arginine and serine, arginine and threonine, arginine and tyrosine, arginine and asparagine, and arginine and glutamine can form a eutectic mixture in a molar ratio of 1:2.
  • the eutectic mixture may be used interchangeably with terms having the same meaning as “eutectic solvent”, “eutectic mixture” or “eutectic mixture aqueous solution”.
  • A is 5% more than B, preferably May be as high as 10%, even more preferably 12%, most preferably 15% or more.
  • A is 5%, preferably, May be as high as 10%, even more preferably 12%, most preferably 15% or more.
  • the cosmetic composition that has elapsed for a certain period of time under high temperature conditions means that it has been stored at 50°C for 6 weeks, or at 60°C for 5 weeks or more.
  • the acidity may be adjusted to have a pH of 3.5 to 10 in order to improve discomfort such as skin irritation.
  • the eutectic mixture according to the present invention can be structurally prepared in a section in which both the amine group of the amino acid or the carboxyl group of the AHA are charged, and thus the section may have a pH of 3.5 or higher.
  • the eutectic mixture may be adjusted to have a weak acidity to neutral acidity such as pH 4 to pH 9, pH 5 to pH 8, and pH 6 to pH 7.
  • the eutectic mixture of the present invention is purified water, AHA and amino acids; Alternatively, by including two kinds of amino acids, the solubility is lowered at low temperatures due to the melting point lowering property of the eutectic mixture, thereby increasing the low temperature stability of the composition.
  • the solubility is lowered at low temperatures due to the melting point lowering property of the eutectic mixture, thereby increasing the low temperature stability of the composition.
  • the eutectic mixture of the present invention can reduce skin irritation that may occur at weak to neutral acidity while maintaining high skin permeability of AHA and/or amino acids as at low pH.
  • the eutectic mixture according to the present invention can be prepared by selecting an arbitrary method commonly used by those skilled in the art and then adding water to the method, and an exemplary method for preparing the eutectic mixture is as follows:
  • the solvent may be evaporated according to the need of the solvent.
  • the eutectic mixture of the present invention can be prepared by the method of ii).
  • a sample is prepared in a reaction tank requiring warming and a homo-disper.
  • a glass beaker or a reaction tank made of SUS may be used.
  • serine and arginine are prepared in a molar ratio of 2:1 for amino acid-amino acid
  • serine and malic acid are prepared in a molar ratio of 2:1 for amino acid-AHA.
  • the amount of purified water may be 25 to 99 parts by weight based on the total weight of the prepared amino acid-amino acid or amino acid-AHA.
  • the speed of the homodisper is preferably 600 to 4000 rpm, but may be higher or lower.
  • the speed of the homodisper may be 600 to 3000 rpm, 600 to 2000 rpm, 600 to 1500 rpm, 800 to 1200 rpm, 900 to 1100 rpm.
  • the heating may be performed under a temperature condition of 45 to 70°C, for example, 45 to 65°C, 45 to 60°C, and 45 to 55°C.
  • the reaction time is preferably at least 15 minutes, and when homogeneity is confirmed, heating can be stopped and natural cooling can be performed.
  • the resulting mixture When the AHA and/or amino acids are completely dissolved, the resulting mixture is transparent and homogeneous, and remains liquid and transparent even after cooling.
  • the eutectic mixture prepared as described above is uniformly present without separating the phase even at a very low temperature, such as a temperature of less than 0° C., thereby maintaining a transparent liquid phase.
  • the eutectic mixture may be maintained without breaking the bond even if the solidification and melting processes are repeated.
  • the cosmetic composition according to the present invention comprises 0.01 to 50 parts by weight, such as 0.05 to 40 parts by weight, 0.1 to 30 parts by weight, 0.5 to 25 parts by weight, 0.1 to 50 parts by weight, 1 to 35 parts by weight, based on the total weight of the cosmetic composition.
  • the content of the eutectic mixture may be appropriately adjusted to the formulation of the cosmetic composition.
  • the cosmetic composition comprising the eutectic mixture according to the present invention can exhibit excellent skin improvement effects such as exfoliation promoting effect, pore number reduction effect, elasticity enhancement and wrinkle improvement effect, and skin regeneration promoting effect. .
  • the cosmetic composition according to the present invention may further include an oily component.
  • the oily component is included in the composition and exists in the outer phase of the eutectic mixture, thereby helping the eutectic mixture to be stably present in the composition.
  • the oily component may be one or more of oil or wax.
  • the oils and waxes can be applied to all of those commonly used as components of cosmetics in the art.
  • silicone oil, ester oil, triglyceride oil, hydrocarbon oil, or vegetable oil may be used as the oil, and one or more of these components may be used in combination as necessary.
  • silicone oil a silicone fluid oil or a silicone crosspolymer dispersed in the oil may be used.
  • silicone-based fluid oils include cyclopentasiloxane, cyclohexasiloxane, cycloheptasiloxane, cyclomethicone, cyclophenylmethicone, cyclotetrasiloxane, cyclotrisiloxane, dimethicone, capryldimethicone, capryl Ryl trimethicone, caprylyl methicone, cetearyl methicone, hexadecyl methicone, hexyl methicone, lauryl methicone, myristyl methicone, phenyl methicone, stearyl methicone, stearyl dimethicone, tri Fluoropropylmethicone, cetyldimethicone, diphenylsiloxypheny
  • the silicone oil components may be used alone or in combination of two or more oils.
  • Dimethicone crosspolymer, dimethicone/vinyl dimethicone crosspolymer, dimethicone PEG-10/15 crosspolymer or PEG-12 dimethicone/PP-20 crosspolymer can be used as the silicone crosspolymer. However, it is not limited thereto.
  • Ester oils include ascorbyl palmitate, ascorbilinolate, ascorbyl stearate, diisostearylmaleate, benzylbenzoate, benzyllaurate, butylene glycol dicaprylate/dicaprate, butylene Glycol diisononanoate, butylene glycolate, butylene glycol stearate, butyl isostearate, cetearyl isononanoate, cetearyl nonanoate, cetyl caprylate, cetylethylhexanoate, Cetylisononanoate, ethylhexyl caprylate/caprate, ethylhexylisononanoate, ethylhexylisostearate, ethylhexyllaurate, hexyllaurate, octyldodecylisostearate, isopropylisostearate, Isostearyl isonon
  • Triglyceride oils include C8-C12 acid triglyceride, C12-C18 acid triglyceride, caprylic/capric/triglyceride, caprylic/capric/lauric triglyceride, and C10-C40 iso.
  • Alkyl acid triglyceride, C10-C18 triglyceride, glyceryl triacetylhydrostearate, soybean glyceride, tribehenin, tricaprine, triethylhexanoin, triheptanoin, triisostearin, tripalmitin or Tristearin can be used.
  • liquid paraffin liquid paraffin, mineral oil
  • paraffin paraffin
  • petrolatum paraffin
  • microcrystalline wax paraffin
  • squalene a paraffin that is used as the hydrocarbon-based oil.
  • Vegetable oils include avocado oil, wheat germ oil, rosehip oil, shea butter, almond oil, olive oil, macadamia oil, argan oil, meadowfoam oil, sunflower oil, castor oil, camellia oil, corn oil, safflower oil, soybean oil. , Rape blossom oil, macadamia nut oil, jojoba oil, palm oil, palm kernel oil, or coconut oil can be used.
  • wax all waxes, such as hydrocarbon wax, vegetable wax, or silicone wax, which are generally used in cosmetics may be used.
  • candelilla wax, carnauba wax, rice wax, bead wax, lanolin, ozokerite, ceresin wax, paraffin wax, microcrystalline wax, C30-C45 alkyldimethylsilylpolypropylsilsesquioxane, Ethylene/propylene copolymer or polyethylene wax may be included, but is not limited thereto.
  • the content of the oily component is not particularly limited, and may be included in the remaining content except for the eutectic mixture described above in the composition.
  • the cosmetic composition of the present invention includes all kinds of ingredients usable in conventional cosmetics, such as a moisturizing agent such as glycerin, butylene glycol, propylene glycol, hexanediol, methylgluces-20, diglycerin, and ethylhexyl glycerin; Sunscreens such as ethylhexylmethoxycinnamate, ethylhexyl salicylate, ethylhexyltriazone, octocrylene, bis-ethylhexyloxyphenol methoxyphenyltriazine; PH adjusting agents such as triethanolamine; Thickeners such as carbomer, xanthan gum, acrylate/C10-30 alkyl acrylate crosspolymer, and hyaluronic acid; Preservatives such as phenoxyethanol, methylparaben, and propyl paraben; Antioxidants such as BHT, Ethyl As
  • each of the above-described components included in the cosmetic composition according to the present invention may preferably be included in the cosmetic composition of the present invention within a range not exceeding the maximum amount stipulated in the "Cosmetic Safety and Technical Standard" established by the Chinese government.
  • the cosmetic composition according to the present invention can be prepared in any formulation conventionally prepared in the art.
  • the cosmetic composition may include a lotion such as a flexible lotion or a nutrient lotion, a spray type lotion, an emulsion such as a facial lotion, a body lotion, a cream such as a nourishing cream, a moisture cream, an eye cream, a stick, an essence, a cosmetic ointment, Spray, gel, pack, sunscreen, makeup base, liquid type or spray type foundation, powder, cleansing lotion, makeup remover such as cleansing oil, cleansing foam, soap, body wash, etc. , But is not limited thereto.
  • the formulation of the cosmetic composition may be balm, water-in-oil (W/O), oil-in-water (O/W), solubilized formulation, or oil formulation.
  • the "solubilized formulation” refers to a formulation in which a small amount of oil component is transparently dissolved in water, and the diameter of the oil drop is smaller than the wavelength of visible light, so it does not interfere with the straightness of light without scattering or reflection. It is a formulation showing a transparency phase.
  • the cosmetic composition having the solubilizing formulation may be a transparent skin, toner, hair tonic, or hair liquid, but the type is not limited thereto.
  • the cosmetic composition of the present invention may be used according to a conventional method of use, and the number of times of use thereof may be varied according to a user's skin condition or taste.
  • the present invention provides a method for producing the cosmetic composition.
  • the cosmetic composition comprises the steps of preparing a eutectic mixture by mixing purified water, amino acids and alpha-hydroxy acids;
  • purified water, amino acids and alpha-hydroxy acids, eutectic mixtures and cosmetic compositions may be applied as described above.
  • the step of preparing the eutectic mixture may be performed under a homogenization condition of 600 to 4000 rpm and 45 to 70°C.
  • the components constituting the eutectic mixture are uniformly mixed under the homogenizing conditions as described above, so that the skin improvement effect of the eutectic mixture, hypoallergenicity to the skin, and excellent formulation stability can be realized.
  • the cosmetic composition comprises the steps of preparing a eutectic mixture by mixing the first amino acid and the second amino acid;
  • the step of preparing the eutectic mixture may include further comprising purified water.
  • the first amino acid, the second amino acid, purified water, the eutectic mixture, and the cosmetic composition may be applied as described above.
  • the step of preparing the eutectic mixture may be performed under a homogenization condition of 600 to 4000 rpm and 45 to 70°C.
  • the components constituting the eutectic mixture are uniformly mixed under the homogenizing conditions as described above, so that the skin improvement effect of the eutectic mixture, hypoallergenicity to the skin, and excellent formulation stability can be realized.
  • the cosmetic composition according to the present invention includes alpha-hydroxy acid (AHA), amino acids and purified water; Or, by including two kinds of amino acids in the form of a eutectic mixture, the skin permeability of AHA and/or amino acids is improved without skin irritation at weakly acidic to neutral pH, resulting in excellent exfoliation effect, pore count reduction effect, skin elasticity enhancement effect, and skin regeneration. It can exhibit an accelerating effect and can be kept stable and uniform even at low temperatures without precipitation of amino acids.
  • AHA alpha-hydroxy acid
  • amino acids amino acids and purified water
  • purified water or, by including two kinds of amino acids in the form of a eutectic mixture, the skin permeability of AHA and/or amino acids is improved without skin irritation at weakly acidic to neutral pH, resulting in excellent exfoliation effect, pore count reduction effect, skin elasticity enhancement effect, and skin regeneration. It can exhibit an accelerating effect and can be kept stable and uniform even at low temperatures without precipitation of amino acids.
  • 3A shows the change in viscosity according to the molar ratio of serine and arginine
  • B shows the change in conductivity according to the molar ratio of serine and arginine.
  • FIG. 4A shows the results of NMR analysis of serine (Ser), and B shows the results of NMR analysis of arginine (Arg).
  • C in FIG. 4B shows the NMR analysis result of the eutectic mixture consisting of serine and arginine
  • D shows the NMR analysis result when citric acid is added to the eutectic mixture consisting of serine and arginine
  • E is composed of serine and arginine. It shows the results of NMR analysis after adding citric acid to the vacuum eutectic mixture and storing it under severe conditions (40°C) for 1 month.
  • 5A shows the IR spectrum analysis result of serine
  • B shows the IR spectrum analysis result of arginine (Arg)
  • C shows the IR spectrum analysis result of the eutectic mixture of serine and arginine.
  • the eutectic mixture aqueous solution was prepared in the following manner.
  • the eutectic mixture of Example 1 was prepared in a liquid form by preparing 18 parts by weight of malic acid (DL-malic acid, FUSO, Japan) having a melting point of about 130°C based on 100 parts by weight of the eutectic mixture, and heating the malic acid to the melting point. . After adding 20 parts by weight of serine (L-serine, EVONIK, Germany) to the liquid malic acid, it was completely dissolved by stirring at 1,300 rpm for 30 minutes while maintaining the temperature. The completely dissolved liquid phase was neutralized to a pH of 6.5 with NaOH.
  • malic acid DL-malic acid, FUSO, Japan
  • serine L-serine, EVONIK, Germany
  • the eutectic mixture of Example 2 was prepared by adding 25 parts by weight of the eutectic mixture of Example 1 prepared above to purified water based on 100 parts by weight of the total eutectic mixture. At this time, 5 parts by weight of serine and 4.5 parts by weight of malic acid were included in the aqueous solution.
  • Example 1 Example 2 Purified water 53 88.25 Malic acid 18 4.5 Serine 20 5 NaOH 9 2.25 total 100 100
  • an aqueous serine solution was prepared by mixing in purified water so that 20 parts by weight of serine (L-Serine, EVONIK, Germany) was included.
  • Serine and malic acid were mixed in purified water, and the pH was adjusted to 6.5 using NaOH.
  • the final mixture aqueous solution was prepared to contain 20 parts by weight of serine (L-Serine, EVONIK, Germany) and 18 parts by weight of malic acid (DL-Malic acid, FUSO, Japan) based on 100 parts by weight of the total mixture.
  • serine L-Serine, EVONIK, Germany
  • purified water so as to contain 5 parts by weight to prepare an aqueous serine solution.
  • Serine and malic acid were mixed in purified water, and the pH was adjusted to 6.5 using NaOH.
  • the final mixture aqueous solution was mixed with purified water to contain 5 parts by weight of serine (L-Serine, EVONIK, Germany) and 4.5 parts by weight of malic acid (DL-Malic acid, FUSO, Japan) based on 100 parts by weight of the total mixture.
  • An aqueous solution of malic acid was prepared.
  • an aqueous solution of malic acid was prepared by mixing in purified water to contain 4.5 parts by weight of malic acid (DL-Malic acid, FUSO, Japan).
  • An aqueous eutectic mixture composed of two amino acids was prepared in the following manner.
  • Example 4 The eutectic mixture of Example 4 was completely dissolved by adding 6 parts by weight of hydrated citric acid (Citric acid, CIBA SPECIALITY CHEMICALS, Switzerland) for pH control to the eutectic mixture of Example 3 and stirring at 1,300 rpm for 30 minutes while maintaining the temperature at 90°C. Was prepared. Thereafter, it was naturally cooled at room temperature, and water was added to the eutectic mixture of Examples 3 and 4 using the Karl Fischer titration method until the water content in the total eutectic mixture became 50 to 55 parts by weight, followed by stirring.
  • the pH values of Examples 3 and 4 were 8.7 and 6.5, respectively.
  • Example 3 Example 4 Purified water 53 52 Arginine 21 15 Serine 26 27 Function citric acid 0 6 total 100 100
  • Example 1 The properties of the eutectic mixture aqueous solution prepared in Example 1, the serine aqueous solution of Comparative Example 1, and the aqueous solution of serine and malic acid of Comparative Example 2 by lowering the melting point were compared.
  • the solutions of Example 1 and Comparative Examples 1 and 2 were allowed to stand at -20°C and the melting point was measured by checking the phase change.
  • FIG. 1 A, B, and C mean Comparative Example 1, Comparative Example 2, and Example 1 in sequence, respectively.
  • the aqueous serine solution of Comparative Example 1 and the aqueous eutectic mixture solution of Examples 1, 3 and 4 having the same serine content as in Example 1 were placed at room temperature (25° C.) and -20 in a 50 ml test tube. It was allowed to stand at °C for 12 hours each for 4 weeks. The stability of the solution was confirmed from the presence or absence of precipitation in the sample, and the results are shown in Table 3 below.
  • the aqueous solution was treated on the back skin of a pig. Specifically, a sample having a diameter of 6 mm was taken from skin such as a pig with a thickness of 1 mm using a biopsy tool. This was placed in a 96-well plate, washed once with phosphate buffered saline (PBS), and then 100 ⁇ l of the eutectic mixture aqueous solution of Example 2 was added. At this time, for comparison of the exfoliation effect, 100 ⁇ l of the serine-apple acid mixture of Comparative Example 4 was added to skin such as pigs in the same manner.
  • PBS phosphate buffered saline
  • the first positive control is applied as a criterion for comparing values between actual experimental examples, and the relative value (%) of exfoliation is [(result of sample)/(value of first positive control) ⁇ 100] It was calculated and described. The results are shown in Table 4.
  • pH Exfoliation Relative value (%) Aqueous solution of [Example 2]: serine-saperic acid eutectic mixture (serine 5 parts by weight, malic acid 4.5 parts by weight) 6.5 92.6 Composition of [Comparative Example 4]: A simple mixture of serine and apple acid (serine 5 parts by weight, malic acid 4.5 parts by weight) 6.5 82.3 [1st positive control] PHA (pH 4.0) 4.0 100 [2nd positive control] PHA (pH 6.0) 6.0 18.8 [Negative control] purified water - 7.1
  • Example 4 As shown in Table 4, it was confirmed that a high keratin peeling effect appeared in the results of Example 2 using the eutectic mixture aqueous solution of the present invention compared to the aqueous serine solution. In addition, despite having a higher pH value in the aqueous solution of Example 2 of the present invention as compared to 10% of gluconolactone (PHA) (first positive control), which is a keratin exfoliation component at pH 4 (pH 6.5 ) It was confirmed that a similar level of exfoliation effect was shown.
  • PHA gluconolactone
  • the aqueous solution of Example 2 of the present invention can achieve an excellent keratin exfoliation effect at a level similar to that of a conventional exfoliation component having a low pH even under weak acidic or neutral pH conditions with little irritation.
  • the eutectic mixture containing purified water had a better keratin peeling effect by increasing the keratin peeling effect in the eutectic mixture aqueous solution of the present invention compared to the aqueous malic acid solution and the simple mixture of serine-apple acid.
  • the skin permeability of the eutectic mixture aqueous solution was confirmed under weakly acidic conditions (pH 6.5).
  • Each of the aqueous solutions of Comparative Examples 1 and 2 and Example 1 was prepared by 10 ⁇ g, and guided to pig skin having a uniform area.
  • a tissue soaked with phosphate buffered saline (PBS) was placed on a 6-well plate, and the pig skin was placed on the tissue and stored for 12 hours at a temperature of 37°C and humidity of 50%. Thereafter, a sample that did not penetrate the skin was removed with a cotton swab and keratin tape, and the weight of the pig skin was measured.
  • PBS phosphate buffered saline
  • Example 2 As shown in Figure 2, under the condition of pH 6.5, compared to the aqueous solution of serine (L-serine in Figure 2), compared to the aqueous solution of the eutectic mixture of the present invention, in the result of Example 2 (eutectic body in Figure 2), higher pig skin It was confirmed that the transmittance appeared. In addition, as shown in Fig. 2 and references, comparison with lactic acid (lactic acid; Reference 1), which is a type of AHA, and salicylic acid (reference 2), which is a type of beta-hydroxy acid ( ⁇ -hydroxy acid, hereinafter referred to as BHA). Thus, it was confirmed that Example 2 exhibits excellent skin penetration efficacy.
  • lactic acid lactic acid
  • Reference 2 which is a type of AHA
  • salicylic acid reference 2
  • BHA beta-hydroxy acid
  • the eutectic mixture of the present invention containing purified water exhibited high pig skin permeability. That is, it can be seen from the high skin permeability of the eutectic mixture according to the present invention that it exhibits an excellent exfoliation effect as previously confirmed in Experimental Example 2.
  • the eutectic mixture aqueous solution of Examples 5 to 7 was prepared with the composition and contents shown in Table 5 below.
  • malic acid DL-Malic acid, FUSO, Japan
  • FUSO FUSO
  • Proline L-Proline, Sigma Aldrich, USA
  • threonine L-Threonine, Sigma Aldrich, USA
  • cysteine L-cystein, Sigma Aldrich, USA
  • Example 5 When the solution is completely dissolved, neutralize it to pH 6.5 with NaOH, cool it naturally at room temperature, measure the moisture content in the whole eutectic mixture using Karl Fischer titration method, and determine whether the eutectic mixture is formed or not, after storage for 4 weeks. It was confirmed whether the sample was precipitated.
  • Table 6 The results are shown in Table 6 below. At this time, the eutectic mixture aqueous solution to which proline was added was described as Example 5, the eutectic mixture aqueous solution to which threonine was added was described as Example 6, and the eutectic mixture aqueous solution to which cysteine was added was described as Example 7.
  • Example 5 Example 6
  • Example 7 Purified water 56 54
  • Malic acid 16 16 16 Proline 20 - - Threonine - 20 - Cysteine - - 20 NaOH 8
  • 10 12 total 100 100 100
  • Example 5 Example 6 Example 7 pH 6.5 6.5 6.5 Formation of eutectic mixture formation formation formation formation formation Formation Moisture content in the aqueous eutectic mixture (based on 100 parts by weight of the total aqueous solution) 56 parts by weight 54 parts by weight 52 parts by weight Sample precipitation after 4 weeks Not precipitated Not precipitated Not precipitated
  • aqueous solution in the composition of Table 7 below.
  • the aqueous phase purified water, 1,2-hexanediol, composition of Example 1
  • the oil phase excluding the aqueous phase of all components was uniformly dissolved at 90°C
  • the aqueous phase was mixed and cooled and coagulated at room temperature to prepare a cosmetic composition of a chestnut formulation.
  • Example 1 1,2-hexanediol 0.5 Cyclopentasiloxane 30 Dimethicone/Vinyl Dimethicone Cross Polymer 13 Ceresin 10 Hexyldecylethylhexanoate 15 Dimethicone/Polysilicon-11 10 PEG-10 Dimethicone 3 Sorbitansquioleate 0.5
  • Example 1 (serine-apple acid-water eutectic mixture aqueous solution) 18 Purified water - total 100
  • a cosmetic composition of an oil-in-water (O/W) formulation containing a eutectic mixture or an aqueous serine solution was prepared according to the composition of Table 8 below. Specifically, of the following components, the aqueous phase was uniformly dissolved at room temperature, and the oil phase was uniformly dissolved at 90°C. Thereafter, the oil phase was mixed in the dissolved water phase and cooled to prepare a cosmetic composition of an oil-in-water formulation.
  • O/W oil-in-water
  • Example 8 Comparative Example 6 Comparative Example 7 Purified water 47.3 67.1 72.1 1,2-hexanediol 2 2 2 glycerin 10 10 10 Butylene Glycol 2 2 2 Cyclopentasiloxane 7 7.2 7.2 Dimethicone 4.5 4.5 4.5 Polysorbate 60 1.5 1.5 1.5 Carbomer 0.35 0.35 0.35 Tromethamine 0.35 0.35 0.35 Example 1 (in parentheses is serine content parts by weight) 25 (5) - - Serine - 5 - total 100 100 100 100 100
  • Example 8 and Comparative Examples 6 and 7 were prepared and applied to pig skin having a uniform area.
  • a tissue soaked with phosphate buffered saline (PBS) was placed on a 6-well plate, and the pig skin was placed on the tissue and stored for 12 hours at a temperature of 37°C and humidity of 50%. Thereafter, a sample that did not penetrate the skin was removed with a cotton swab and keratin tape, and the weight of the pig skin was measured. After crushing the pig skin with a homogenizer, 1 ml of water was added to sufficiently dissolve the amino acid and eutectic mixture in the sample, followed by centrifugation at 12,000 rpm for 10 minutes.
  • PBS phosphate buffered saline
  • Example 8 Comparative Example 6 Comparative Example 7 Serine pigskin permeation per unit area [ ⁇ g/cm 2 ] 1.81 ⁇ 0.054 1.02 ⁇ 0.042 Not detected
  • Example 8 the skin permeability was improved by about 77% compared to Comparative Example 6 containing the same amount of serine.
  • a cosmetic composition of a water-in-oil (W/O) formulation including an aqueous eutectic mixture was prepared according to the composition of Table 10 below. Specifically, of the following components, the aqueous phase was uniformly dissolved at room temperature, and the oil phase was uniformly dissolved at 90°C. Thereafter, the aqueous phase was mixed with the dissolved oil phase and cooled to prepare a water-in-oil formulation cosmetic composition.
  • Example 2 Purified water 45.4
  • Example 1 saliva-apple acid-water eutectic mixture aqueous solution 15
  • Sodium chloride One 1,2-hexanediol 0.7 glycerin 17
  • Dipropylene glycol 5
  • Dimethicone 9.5
  • Diphenylsiloxyphenyltrimethicone One PEG-10 Dimethicone 0.2 Dimethicone, Dimethicone/PG-10/15 Crosspolymer 5.2 total 100
  • a cosmetic composition of an oil-in-water (O/W) formulation containing an aqueous eutectic mixture was prepared in the composition of Table 11 below. Specifically, the aqueous phase and the oil phase of the following components were uniformly dissolved at room temperature, respectively, and then, the oil-in-water formulation was prepared by mixing the oil phase in the dissolved aqueous phase.
  • Example 9 Comparative Example 8 Purified water 58.3 73.3
  • Example 1 serum-apple acid-water eutectic mixture aqueous solution
  • 15 1,2-hexanediol
  • Butylene Glycol 2 Cyclopentasiloxane 7 7 Dimethicone 4.5 4.5
  • Polysorbate 60 1.5 1.5 Acrylate/C10-30 alkyl acrylate crosspolymer 0.35 0.35 Tromethamine 0.35 0.35 total 100 100
  • a cosmetic composition of a solubilized formulation containing an aqueous eutectic mixture was prepared according to the composition of Table 12 below. Specifically, the aqueous phase and a small amount of the oil phase of the following components were uniformly dissolved at room temperature, respectively, and then, a small amount of the oil phase was mixed in the dissolved aqueous phase to prepare a solubilized cosmetic composition.
  • Example 10 Comparative Example 9 Purified water 79.7 87.7
  • Example 3 (serine-arginine eutectic mixture aqueous solution) 8 - Modified alcohol 2 2 glycerin 4 4 Butylene Glycol 2 2 1,2-hexanediol 2 2 PEG-40 Hydrogenated Castor Oil 0.6 0.6 Carbomer 0.8 0.8 Tromethamine 0.8 0.8 Spices 0.1 0.1 total 100 100
  • a cosmetic composition of an oil formulation containing an aqueous eutectic mixture solution in the composition of Table 13 below Specifically, a small amount of the aqueous phase and the oil phase of the following components were uniformly dissolved at room temperature, respectively, and then, a small amount of the dissolved aqueous phase was mixed with the oil phase to prepare a cosmetic composition in an oil formulation.
  • Example 11 Comparative Example 10
  • Example 3 (serine-arginine eutectic mixture aqueous solution) 0.5 - Mineral oil 8 8 Olive oil 10 10 Cetylethylhexanoate 76.6 76.6 PEG-30 Solbitan Tetraoleate 4.9 4.9 Purified water - 0.5 total 100 100
  • Example 9 and Comparative Example 8 prepared as described above were applied to the skin for 9 weeks to evaluate the skin improvement effect (skin tone, skin texture, number of pores and number of blackheads).
  • the subject's face was divided into half by a virtual line passing through the nose, and the cosmetic composition of Example 9 was applied to the right skin, respectively, and the cosmetic composition of Comparative Example 8 was applied to the left skin of the subject.
  • week 3 and week 9 the effect of improving the skin on the right and left was compared by looking at the mirror, and sensory evaluation was performed using a 5-point scale.
  • the results are shown in Table 14. In the case of week 0 in Table 14 below, the score of concern for each corresponding item was shown using a 5-point scale.
  • the efficacy of the eutectic mixture was evaluated by comparing only the left and right states at each time point without evaluating the change in satisfaction for each week in order to exclude external factors over time such as season, individual physical condition, and mood.
  • Example 10 and 11 and Comparative Examples 9 and 10 prepared as described above were applied to the skin and then wiped off with lukewarm water to evaluate the effect of improving sensation by short-term application in the wash-off type.
  • Experiment 1 by having the subject use one product randomly selected from Example 10 or Comparative Example 9 on the first day, and using another product not selected on the first day of Example 10 or Comparative Example 9 on the second day.
  • sensory evaluation was performed on a 5-point scale after the blind test for changes in haptic effects before applying the product and after wiping the product with lukewarm water, respectively.
  • the inventor who is the experimenter, knows which product the subject selected is, and the subject was subjected to a blind test until the survey was completed.
  • Example 11 or Comparative Example 10 it was evaluated in the same manner as above. Through the above experiment, it was confirmed whether consumers experience the short-term efficacy according to the presence or absence of the eutectic mixture in the solubilizing formulation (Example 10 and Comparative Example 9) and the oil formulation (Example 11 and Comparative Example 9), which are two different formulations. The results are shown in Tables 15 and 16, respectively.
  • Serine arginine as a component constituting the eutectic mixture was prepared in a molar ratio of 2:1, and purified water in an amount equal to the total weight was prepared. That is, the amount of purified water was such that the content of purified water was 50 wt% based on the total weight.
  • the homodisper was heated to maintain a speed of 1000 rpm and a temperature of 50°C. After reacting for 20 minutes, when homogeneity was confirmed, heating was stopped and natural cooling was performed.
  • sample Composition (molar ratio) characteristic stability Serine: Arginine 4: 1 Yellow fluidic liquid Not stable; Solid precipitation within 3 days 3: 1 Yellow viscous liquid Not stable; Solid precipitation within 21 days 2: 1 (form eutectic mixture) Yellow viscous liquid Stable; Not precipitated within 2 months 1: 1 Yellow viscous liquid Not stable; Solid precipitation within 21 days 1: 2 Yellow liquid Not stable; Solid precipitation within 14 days 1: 3 Yellow liquid Not stable; Solid precipitation within 3 days 1: 4 Yellow liquid Not stable; Solid precipitation within 1 day
  • NMR analysis of the eutectic mixture NMR analysis (A and B in Fig. 4A) of serine and arginine was performed.
  • NMR analysis of a eutectic mixture of serine and arginine C in FIG. 4B
  • adding citric acid as a pH adjuster that can make cosmetic formulations weakly acidic while having a strong surface charge that affects the binding in the formulation.
  • NMR analysis of the serine-arginine eutectic mixture (D in FIG. 4B) and NMR analysis results (E in FIG. 4B) after adding citric acid to the eutectic mixture and storing for 1 month under severe conditions (40°C) are shown in FIGS. 4A and 4B. Indicated.
  • the essence (emulsion) containing the serine and arginine eutectic mixture prepared in Example 12 was applied to the skin, and the number of pores was measured for 6 weeks to confirm the effect of reducing the number of pores.
  • the effect of reducing the number of pores is the number of pores recognized by the device, and it was determined that the size, color, and prominence of a single pore decreased, and if the device did not recognize it as a pore, the number of pores decreased.
  • the device used was an Antera 3D® CS skin analyzing camera (Miravex), and the same evaluator achieved the same skin condition through the subject's skin adaptation for 20 minutes in a constant temperature and humidity environment, and then measured and evaluated at the same point on the left and right cheeks.
  • the effect of reducing the number of pores means an effect of improving enlarged pores.
  • the results are divided by age group and shown in Fig. 6 and Table 18, respectively.
  • Example 12 The skin permeability of the eutectic mixture prepared in Example 12 was confirmed. A specific experimental method was performed in the same manner as in Experimental Example 3. Results for Example 12 are shown in Table 20.
  • Example 12 Serine-arginine eutectic mixture (serine 5 parts by weight, arginine 4.1 parts by weight) 9.1 96.4 Sample of the eutectic mixture of [Example 12] whose pH was adjusted to weakly acidic using citric acid (serine 5 parts by weight, arginine 4.1 parts by weight) 6.0 100 [Comparative Example 11]: Serine-arginine simple mixture (serine 5 parts by weight, arginine 4.1 parts by weight) 9.1 46.2 A simple mixture of [Comparative Example 11] whose pH was adjusted to weakly acidic using citric acid (serine 5 parts by weight, arginine 4.1 parts by weight) 6.0 82.4 Serine (5 parts by weight) 6.0 71.7
  • the eutectic mixture of Example 12 according to the present invention has excellent skin permeability even under the condition of pH 9.1 without adjusting the pH. I did.
  • the simple mixture of serine and arginine showed significantly lower skin permeability than that of Example 12, and even when the pH was adjusted to 6.0, the result was lower than that of the eutectic mixture according to the present invention.
  • Arginine glutamic acid as a component constituting the eutectic mixture was prepared in a molar ratio of 1:1, and purified water in an amount equal to the total weight was prepared. That is, the amount of purified water was such that the content of purified water was 50 wt% based on the total weight.
  • the homodisper was heated to maintain a speed of 1000 rpm and a temperature of 50°C. After reacting for 20 minutes, when homogeneity was confirmed, heating was stopped and naturally cooled to prepare a eutectic mixture in the same manner as in Example 12.
  • DMEM fetal bovine serum
  • penicillin 100 mg/ml penicillin
  • streptomycin 100 mg/ml streptomycin in HaCaT cells
  • a human-derived keratinocyte cell line It was cultured at 37° C. and 5% CO 2 using a medium (ADDEXBIO TECHNOLOGIES, SanDiego, CA, USA).
  • a medium ADEXBIO TECHNOLOGIES, SanDiego, CA, USA.
  • an arginine-glutamic acid eutectic mixture (Arg-Glu eutectic mixture) and 10% FBS-DMEM corresponding to the optimal growth conditions of the cell line as a negative control was used as a negative control.
  • the two amino acids, the Arg-Glu eutectic mixture 1 ppm treatment group showed better wound recovery rate than the FBS 10% treatment group (positive control).
  • the wound recovery rate of 10 ppm of the Arg-Glu eutectic mixture was 92.2%, and it was confirmed that most of the empty spaces due to scratches were covered with cells even on the microscope image.
  • This effect of 10 ppm of the Arg-Glu eutectic mixture is superior to the group treated with 10 ppm arginine/1 ppm glutamic acid (the maximum concentration of glutamic acid that can be produced is 1 ppm) and the group treated with 1 ppm arginine, which is a simple mixture of two amino acids. It was confirmed that the -Glu eutectic mixture can help in skin regeneration by promoting cell regeneration compared to when each is applied alone or when simply mixed.
  • the total amount of collagen was quantified using the PICP EIA kit (Procollagen Type I C-Peptide Enzyme ImmunoAssay KIT). Before the experiment, the cytotoxicity of the Arg-Glu eutectic mixture was varied by varying the concentration ( ⁇ g/ml) of human-derived fibroblasts, and the degree of increase in the total amount of collagen was determined by selecting a concentration without cytotoxicity (100 ⁇ g/ml). Evaluated.
  • each sample was added to the culture medium of human fibroblasts and cultured for 1 day, and then the culture solution was taken and the degree of increase in the total amount of collagen at each concentration was measured at 450 nm using a PICP EIA kit.
  • the increase in the total amount of collagen was confirmed by the same method for the culture medium of fibroblasts to which nothing was added (negative control) and the sample added so that the final concentration of TGF- ⁇ fmf was 10 mg/ml (positive control). I did.
  • the total amount of collagen was measured as UV absorbance, and the rate of increase of the total amount of collagen was calculated as the ratio of the total amount of collagen relative to the control, and the results are shown in Table 23 below.
  • the concentration of the Arg-Glu eutectic mixture and the Arg/Glu (1:10) simple mixture was based on the concentration of arginine.
  • the Arg-Glu eutectic mixture showed the effect of increasing the total amount of collagen by promoting collagen synthesis in a concentration-dependent manner, and at a concentration of 1 ppm or more, the same concentration of Arg/Glu (1:10) The collagen increase rate was better than that of the mixture. In addition, it was confirmed that the Arg-Glu eutectic mixture was also excellent in the increase rate of collagen compared to the single amino acids Arg and Glu.
  • B Arg-Glu eutectic mixture One 0 Purified water Balance Balance glycerin 8.0 8.0 Butylene glycol 4.0 4.0 Hyaluronic acid extract 5.0 5.0 Beta glucan 7.0 7.0 Carbomer 0.15 0.15 Caprylic/Capric Triglyceride 8.0 8.0 Squalane 5.0 5.0 Cetearyl glucoside 1.5 1.5 Sorbitan stearate 0.4 0.4 Cetearyl alcohol 2.0 2.0 antiseptic Appropriate amount Appropriate amount Pigment Appropriate amount Appropriate amount Triethanolamine 0.15 0.15 total 100 100 100
  • the eutectic mixture when forming a eutectic mixture in a specific solvent, the eutectic mixture is placed in an over-melted state above the solubility of each component species.
  • the bond of the eutectic mixture in the case of an overmelted solution forming a eutectic mixture using water as a solvent, it can be confirmed that the bond of the eutectic mixture is dissociated through the occurrence of irreversible precipitates under the following conditions:
  • the bonds between the eutectic materials in the eutectic mixture can be broken and broken through the occurrence of irreversible precipitates under the conditions i) to iii).
  • whether or not the eutectic mixture is dissociated can be determined using a substance that can break bonds between eutectic substances, such as EDTA, a protic solvent, a high concentration of urea, or a substance such as guanidyl HCl. I can.
  • the reversible precipitation refers to precipitation that returns to a transparent (homogeneous) solution state by simple mixing (hand shaking) about 10 to 20 times after the precipitate of the eutectic mixture is observed, and the dissociation conditions of i) to iii) above. It was confirmed that precipitation occurs temporarily when allowed to stand at a low temperature (-20 °C), but it was confirmed that it was homogenized through simple mixing. Irreversible precipitation means precipitation that is not homogenized when going through the above process.
  • the melting point was measured using a Perkin Elmer Diamond DSC (Differential Scanning Calorimeter; Perkin Elmer, Waltham, MA, USA).
  • the melting point is expressed as the heat flow for the sample in the DSC, and its accuracy is known to be 0.01 °C.
  • the melting point measurement was performed in a pure nitrogen atmosphere, supplied into the measurement chamber at a rate of 20 cc/min to maintain the nitrogen atmosphere, and the temperature of the chamber was set to increase by 10° C. per minute.
  • the mass of the measurement sample was confirmed by subtracting the weight of the pan for containing the sample in the DSC from the weight including the entire sample.
  • the pan was allowed to stand inside the DSC, and the heat flow was measured by heating by setting the temperature from -50°C to 90°C. After that, the results were confirmed through a data analysis program connected to the DSC.
  • the melting point of the cosmetic composition containing the simple mixture without forming the eutectic mixture was confirmed at 0°C, which is the melting point of water, but the melting point of the cosmetic composition containing the eutectic mixture was confirmed at -3.83°C due to the melting point drop phenomenon.
  • the melting point was observed at 0°C, indicating that the eutectic mixture was dissociated to form a simple mixture.
  • the essence containing the eutectic mixture of [Example 12] is the essence (including the dissociated product of the eutectic mixture) after storing the essence containing the eutectic mixture of [Example 12] at 50° C. for 6 weeks (severe conditions) Compared to that, about 20% higher exfoliation effect was observed.
  • the dissociated product of the eutectic mixture is similar to the essence containing the simple mixture. It was confirmed that the melting point and keratin peeling effect appeared. That is, it was proved that it is possible to confirm whether or not the eutectic mixture is dissociated.

Landscapes

  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Birds (AREA)
  • Epidemiology (AREA)
  • Dermatology (AREA)
  • Gerontology & Geriatric Medicine (AREA)
  • Emergency Medicine (AREA)
  • Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Organic Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Cosmetics (AREA)
  • Dispersion Chemistry (AREA)
PCT/KR2020/011202 2019-08-21 2020-08-21 공융 혼합물을 포함하는 화장료 조성물 Ceased WO2021034150A1 (ko)

Priority Applications (8)

Application Number Priority Date Filing Date Title
CN202410327676.5A CN118217176A (zh) 2019-08-21 2020-08-21 包含共晶混合物的化妆料组合物
CN202410327679.9A CN118217177A (zh) 2019-08-21 2020-08-21 包含共晶混合物的化妆料组合物
EP25189565.2A EP4623891A3 (en) 2019-08-21 2020-08-21 Cosmetic composition comprising eutectic mixture
US17/636,753 US20220287938A1 (en) 2019-08-21 2020-08-21 Cosmetic composition comprising eutectic mixture
EP20854144.1A EP4018996B1 (en) 2019-08-21 2020-08-21 Cosmetic composition comprising eutectic mixture
CN202080073446.0A CN114555043B (zh) 2019-08-21 2020-08-21 包含共晶混合物的化妆料组合物
JP2022511298A JP7601858B2 (ja) 2019-08-21 2020-08-21 共融混合物を含む化粧料組成物
JP2024211600A JP7842181B6 (ja) 2019-08-21 2024-12-04 共融混合物を含む化粧料組成物

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
KR10-2019-0102243 2019-08-21
KR20190102243 2019-08-21

Publications (1)

Publication Number Publication Date
WO2021034150A1 true WO2021034150A1 (ko) 2021-02-25

Family

ID=74660716

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/KR2020/011202 Ceased WO2021034150A1 (ko) 2019-08-21 2020-08-21 공융 혼합물을 포함하는 화장료 조성물

Country Status (6)

Country Link
US (1) US20220287938A1 (https=)
EP (2) EP4623891A3 (https=)
JP (1) JP7601858B2 (https=)
KR (4) KR102269121B1 (https=)
CN (3) CN118217176A (https=)
WO (1) WO2021034150A1 (https=)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN113233976A (zh) * 2021-05-08 2021-08-10 广州萃普生物科技有限公司 一种没食子酸和氨基乙酸共晶及含有该共晶的美白膏霜
CN114315565A (zh) * 2021-12-07 2022-04-12 河北科技大学 一种乙醇酸/丙氨酸天然低共熔离子液体及其制备方法和应用

Families Citing this family (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2022101490A1 (en) * 2020-11-13 2022-05-19 Universidade Do Minho Eutectic compositions, methods and uses thereof
CN115869209A (zh) * 2021-09-29 2023-03-31 株式会社Lg生活健康 包含维生素c的低共熔混合物的化妆料组合物
CN115645362B (zh) * 2022-10-24 2024-04-26 中国海洋大学 一种水杨酸天然低共熔溶剂及低共熔凝胶和应用
KR102894987B1 (ko) * 2022-12-23 2025-12-10 주식회사 잇츠한불 무화과 공융 용매 추출물을 포함하는 피부 세정용 또는 피부 상태 개선용 화장료 조성물
CN117229165B (zh) * 2022-12-30 2025-12-12 广州中妆美业化妆品有限公司 一种茶氨酸组合物及其制备方法、应用
KR20250090197A (ko) * 2023-12-12 2025-06-19 주식회사 엘지생활건강 피부 진정용 화장료 조성물

Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5420106A (en) * 1994-03-22 1995-05-30 Bristol-Myers Squibb Company Method and composition having enhanced alpha-hydroxy acid skin permeation and retention
US6410036B1 (en) * 2000-05-04 2002-06-25 E-L Management Corp. Eutectic mixtures in cosmetic compositions
KR101120660B1 (ko) * 2005-12-21 2012-03-16 주식회사 엘지생활건강 알파-하이드록시 에시드 및 에테르계 계면활성제를포함하는 화장료 조성물
JP2013112627A (ja) * 2011-11-28 2013-06-10 Goo Chemical Co Ltd 化粧料組成物及びその製造方法
KR101508168B1 (ko) 2011-08-03 2015-04-07 가부시키가이샤 시세이도 각전 재생 억제제, 각전 재생 억제 방법, 및 각전 재생 억제 키트
JP2019048771A (ja) * 2017-07-20 2019-03-28 ロレアル バイオサーファクタント、塩基性アミノ酸、及びアルファ−ヒドロキシ酸を含む、ケラチン物質を処置するための組成物
JP2019116421A (ja) * 2017-12-15 2019-07-18 ロレアル ヒドロキシ酸、塩基性アミノ酸、及びアミノ酸系界面活性剤を含む、ケラチン物質を処置するための組成物

Family Cites Families (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR100490212B1 (ko) * 2002-06-21 2005-05-17 주식회사 바이오랜드 피부 각질층의 아미노산 구성비율을 가지는 아미노산복합물과 그것을 함유한 노화방지 화장료 조성물
WO2011051974A1 (en) * 2009-10-29 2011-05-05 Nutracryst Therapeutics Private Limited Metformin and a-amino acids
EP2516016B1 (en) * 2009-12-23 2018-04-11 Colgate-Palmolive Company Anhydrous liquid antiperspirant/deodorant composition
JP2016538405A (ja) * 2013-09-24 2016-12-08 ネステク ソシエテ アノニム 深共晶溶媒及びフレーバー発生
EP3270701B1 (en) * 2015-03-19 2019-01-02 Nestec S.A. Process for producing creamer compositions
FR3034625A1 (fr) * 2015-04-10 2016-10-14 Naturex Solvant eutectique d'extraction, procede d'extraction par eutectigenese utilisant ledit solvant, et extrait issu dudit procede d'extraction.
FR3036618B1 (fr) * 2015-05-26 2018-11-02 Gattefosse S.A.S. Extraits vegetaux destines a la cosmetique, solvants et procedes pour les obtenir
CN107789264A (zh) * 2016-08-31 2018-03-13 张恒元 一种芦荟润肤霜
CN106389225A (zh) * 2016-11-22 2017-02-15 郑州兰茜生物工程有限公司 一种红酒补水保湿营养面膜及其制备方法
KR102021056B1 (ko) * 2018-11-22 2019-09-11 주식회사 비에스글로벌홀딩스 전기분해 해수 및 아미노산복합체를 함유하는 화장료 조성물
CN109464337A (zh) * 2018-12-23 2019-03-15 广州航美化妆品有限公司 紧致祛皱精华

Patent Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5420106A (en) * 1994-03-22 1995-05-30 Bristol-Myers Squibb Company Method and composition having enhanced alpha-hydroxy acid skin permeation and retention
US6410036B1 (en) * 2000-05-04 2002-06-25 E-L Management Corp. Eutectic mixtures in cosmetic compositions
KR101120660B1 (ko) * 2005-12-21 2012-03-16 주식회사 엘지생활건강 알파-하이드록시 에시드 및 에테르계 계면활성제를포함하는 화장료 조성물
KR101508168B1 (ko) 2011-08-03 2015-04-07 가부시키가이샤 시세이도 각전 재생 억제제, 각전 재생 억제 방법, 및 각전 재생 억제 키트
JP2013112627A (ja) * 2011-11-28 2013-06-10 Goo Chemical Co Ltd 化粧料組成物及びその製造方法
JP2019048771A (ja) * 2017-07-20 2019-03-28 ロレアル バイオサーファクタント、塩基性アミノ酸、及びアルファ−ヒドロキシ酸を含む、ケラチン物質を処置するための組成物
JP2019116421A (ja) * 2017-12-15 2019-07-18 ロレアル ヒドロキシ酸、塩基性アミノ酸、及びアミノ酸系界面活性剤を含む、ケラチン物質を処置するための組成物

Non-Patent Citations (4)

* Cited by examiner, † Cited by third party
Title
JOURNAL OF THE KOREAN SOCIETY FOR WELLNESS, vol. 10, no. 2, 2015, pages 161 - 169
S. E. COLI WOLVERTON: "Comprehensive Dermatologic Drug Therapy", 2012, ELSEVIER, article "a-Hydroxy acids", pages: 570
See also references of EP4018996A4
TATSUYA OZAWA ET AL.: "The role of humectants in skin moisture retention", SKIN RESEARCH, vol. 27, 1985, pages 276 - 288

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN113233976A (zh) * 2021-05-08 2021-08-10 广州萃普生物科技有限公司 一种没食子酸和氨基乙酸共晶及含有该共晶的美白膏霜
CN114315565A (zh) * 2021-12-07 2022-04-12 河北科技大学 一种乙醇酸/丙氨酸天然低共熔离子液体及其制备方法和应用
CN114315565B (zh) * 2021-12-07 2023-12-19 河北科技大学 一种乙醇酸/丙氨酸天然低共熔离子液体及其制备方法和应用

Also Published As

Publication number Publication date
CN118217177A (zh) 2024-06-21
EP4623891A3 (en) 2025-12-03
KR102411385B1 (ko) 2022-06-22
CN114555043A (zh) 2022-05-27
EP4018996A4 (en) 2023-09-20
CN118217176A (zh) 2024-06-21
KR20220088662A (ko) 2022-06-28
JP7842181B2 (ja) 2026-04-07
EP4018996A1 (en) 2022-06-29
EP4623891A2 (en) 2025-10-01
KR102269121B1 (ko) 2021-06-25
EP4018996B1 (en) 2025-09-17
JP2022544839A (ja) 2022-10-21
KR102526146B1 (ko) 2023-04-27
KR20210023770A (ko) 2021-03-04
JP7601858B2 (ja) 2024-12-17
JP2025028101A (ja) 2025-02-28
KR102626486B1 (ko) 2024-01-19
KR20230058360A (ko) 2023-05-03
US20220287938A1 (en) 2022-09-15
CN114555043B (zh) 2024-04-12
KR20210075949A (ko) 2021-06-23

Similar Documents

Publication Publication Date Title
WO2021034150A1 (ko) 공융 혼합물을 포함하는 화장료 조성물
WO2015088126A1 (ko) 카르보디이미드계 화합물을 포함하는 조성물
CN101522164A (zh) 用于治疗皮肤的化妆品组合物及其方法
WO2020204293A1 (ko) 자외선 차단용 화장료 조성물
WO2020040442A1 (ko) 수딩 크림 및 이의 제조 방법
WO2016200190A1 (ko) 칠엽담으로부터 분리된 지페노사이드를 포함하는 주름 개선용 화장료 조성물
WO2017146414A1 (ko) α-테르피네올을 유효성분으로 함유하는 피부 보습 및 피부 주름 개선용 조성물
WO2020204403A1 (ko) 자외선, 근적외선 및/또는 블루라이트 차단용 복합 분체 및 이를 포함하는 화장료 조성물
WO2023033414A1 (ko) 유효 성분의 포집력이 우수한 리포좀 화장료 조성물
WO2019240495A1 (ko) 가역적인 졸-겔 현상이 일어나는 박테리얼 셀룰로오스 겔의 용도
WO2018186640A1 (ko) 오시멘 또는 이의 염을 유효성분으로 함유하는 피부주름 개선, 보습, 탄력증진, 각질제거, 홍반억제 또는 피부광노화 개선용 조성물
WO2021112325A1 (ko) 해조류 유래 다당류를 유효성분으로 포함하는 피부 보습용 또는 진정용 인체 세정제 조성물
WO2019103194A1 (ko) 올레아놀릭산 및 살비아놀릭산을 포함하는 피부 미백 또는 주름 개선용 화장료 조성물
WO2018186641A1 (ko) 피페로날 또는 이의 염을 유효성분으로 함유하는 피부주름 개선, 보습, 탄력증진, 각질제거, 홍반억제 또는 피부광노화 개선용 조성물
WO2018186644A1 (ko) 자스몬 또는 이의 염을 유효성분으로 함유하는 피부주름 개선, 보습, 탄력증진, 각질제거, 홍반억제 또는 피부광노화 개선용 조성물
WO2023113431A1 (ko) 신규한 균주 및 이의 용도
WO2018186643A1 (ko) 신코닌 또는 이의 염을 유효성분으로 함유하는 피부주름 개선, 보습, 탄력증진, 각질제거, 홍반억제 또는 피부광노화 개선용 조성물
WO2025150661A1 (ko) 핑거루트 추출물을 함유한 핑거루트 리포좀 및 그 제조 방법
WO2021215574A1 (ko) 2,3-부탄다이올을 포함하는 분산제 또는 분산매 조성물, 및 이를 포함하는 화장료 조성물
WO2018186639A1 (ko) 요놀 또는 이의 염을 유효성분으로 함유하는 피부주름 개선, 보습, 탄력증진, 각질제거, 홍반억제 또는 피부광노화 개선용 조성물
WO2024232642A1 (ko) 세포배양배지 및 알부민을 포함하는 화장료 조성물 및 이의 용도
WO2017018847A1 (ko) 미리세틴 유도체를 함유하는 snare 복합체 형성 억제용 조성물
JP7842181B6 (ja) 共融混合物を含む化粧料組成物
WO2024106821A1 (ko) 피부 미백 활성을 갖는 펩타이드 및 이의 용도
WO2022250348A1 (ko) 시스테인 유도체의 피부 미백 용도

Legal Events

Date Code Title Description
121 Ep: the epo has been informed by wipo that ep was designated in this application

Ref document number: 20854144

Country of ref document: EP

Kind code of ref document: A1

ENP Entry into the national phase

Ref document number: 2022511298

Country of ref document: JP

Kind code of ref document: A

NENP Non-entry into the national phase

Ref country code: DE

ENP Entry into the national phase

Ref document number: 2020854144

Country of ref document: EP

Effective date: 20220321

WWG Wipo information: grant in national office

Ref document number: 2020854144

Country of ref document: EP