Composition for caring for keratinous materials

A stable anhydrous composition with nonionic surfactants and dipropylene glycol forms microemulsions with aqueous systems, addressing the degradation issues of ascorbic acid and ferulic acid, enhancing their bioavailability and penetration in cosmetic products.

JP7787200B2Active Publication Date: 2025-12-16LOREAL SA
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Patent Information

Application Number
JP2023560145
Authority / Receiving Office
JP · JP
Patent Type
Patents
Current Assignee / Owner
Filing Date
2021-03-30
Publication Date
2025-12-16
Estimated Expiration
2041-03-30

AI Technical Summary

Technical Problem

Formulating cosmetic products with ascorbic acid and ferulic acid is challenging due to their sensitivity to oxygen and water, leading to rapid degradation and loss of stability and bioavailability.

Method used

A composition comprising cosmetically active ingredients sensitive to oxygen and/or water, combined with nonionic surfactants like polyglyceryl fatty acid esters and ethoxylated/propoxylated fatty alcohols, and dipropylene glycol, forming stable anhydrous compositions that can be mixed with aqueous systems to create microemulsions for enhanced bioavailability.

Benefits of technology

The composition maintains stability for at least two months and enhances the bioavailability of active ingredients by forming microemulsions when mixed with water, allowing deeper penetration into keratinous materials.

✦ Generated by Eureka AI based on patent content.

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Abstract

The present invention relates to an anhydrous composition for caring for keratinous materials, comprising: a) at least one cosmetically active ingredient that is sensitive to water and / or oxygen; b) at least one nonionic surfactant selected from polyglyceryl fatty acid esters having an HLB value of 13 or more at a temperature of 25° C. and ethoxylated / propoxylated fatty alcohols; and c) dipropylene glycol, the composition being free of any cationic surfactant. The present invention also relates to a non-therapeutic method for caring for keratinous materials, comprising mixing the anhydrous composition with water or a water-containing system to form a microemulsion and applying the microemulsion to the keratinous materials.
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Description

[Technical Field]

[0001] The present invention relates to a composition for caring for keratinous materials. The present invention also relates to a non-therapeutic method for caring for keratinous materials. [Background technology]

[0002] Ascorbic acid (vitamin C) is a powerful antioxidant active ingredient that stimulates the synthesis of connective tissue, especially collagen, enhances the defense of skin tissue against damage caused by environmental factors such as UV radiation and pollution, compensates for any vitamin E deficiency in the skin, removes skin pigmentation, and has anti-free radical functions. These last two properties make ascorbic acid an excellent candidate as a cosmetic or dermatological active agent to combat and / or prevent skin aging.

[0003] Ferulic acid is an antioxidant active agent that can provide whitening / brightening, anti-inflammatory and UV protection benefits.

[0004] It is desirable in the cosmetic and dermatological fields to formulate products containing ascorbic acid or ferulic acid.

[0005] However, formulating such products faces significant challenges.

[0006] Due to its chemical structure (alpha-keto lactone), ascorbic acid is highly sensitive to certain environmental factors, such as oxygen and water, in whose presence rapid degradation of ascorbic acid occurs, which causes a decrease in potency and a change in color.

[0007] When ferulic acid comes into contact with water, it undergoes a decarboxylation reaction within several days, for example, 7 days if the ferulic acid content is 1.9% by mass or more, 15 days if the ferulic acid content is 1.5% by mass or more, and 30 days if the ferulic acid content is 1% by mass or more, resulting in a loss of stability of the ferulic acid and the generation of an unpleasant odor.

[0008] Some products focus on anhydrous cosmetic base to avoid contact with water.For example, there are some two-component products, in which cosmetic active ingredients, such as ascorbic acid and ferulic acid, are present in the form of anhydrous powder.However, for some products, the bioavailability of active ingredients is an issue.

[0009] There remains a need for cosmetic preparations containing active ingredients, such as ascorbic acid or ferulic acid, that are stable and provide bioavailability of the cosmetic active ingredient. [Prior art documents] [Non-patent literature]

[0010] [Non-Patent Document 1] J. Ploughshare. Cosm. Chem. 1954 (Vol. 5), pp. 249-256 [Non-patent document 2] Satoshi Tomomasa et al., Oil Chemistry, Vol. 37, No. 11 (1988), pp. 48-53 Summary of the Invention [Problem to be solved by the invention]

[0011] It is therefore an object of the present invention to provide a composition for caring for keratinous materials, comprising a cosmetically active ingredient that is sensitive to oxygen and / or water, that is stable, i.e., the cosmetically active ingredient therein does not substantially decompose.

[0012] It is therefore another object of the present invention to provide a composition for caring for keratinous materials that contains a cosmetically active ingredient that is sensitive to oxygen and / or water and that provides bioavailability of the cosmetically active ingredient.

[0013] Yet another object of the present invention is to provide a non-therapeutic method for caring for keratinous materials. [Means for solving the problem]

[0014] Thus, according to one aspect, the present invention provides a method for producing a cellular membrane comprising: a) at least one cosmetically active ingredient that is sensitive to water and / or oxygen; b) at least one nonionic surfactant selected from polyglyceryl fatty acid esters having an HLB value of 13 or greater at a temperature of 25°C and ethoxylated / propoxylated fatty alcohols; and c) Dipropylene glycol 1. An anhydrous composition for caring for keratinous materials, comprising: The composition is provided without any cationic surfactants.

[0015] Anhydrous compositions according to the present invention are stable for at least two months.

[0016] In this application, stability is assessed by testing the degradation of the cosmetically active ingredient.

[0017] Surprisingly, the inventors have found that, by gentle mixing, anhydrous compositions can be mixed with water or aqueous systems to form microemulsions, which enhance the bioavailability of cosmetically active ingredients.

[0018] The aqueous system may be any system that contains 40% or more by weight of water relative to the total weight of the system.

[0019] According to another aspect, the present invention provides a non-therapeutic method for caring for keratinous materials, comprising: i) mixing an anhydrous composition according to the present invention with water or an aqueous system to form a microemulsion; and ii) applying the microemulsion to the keratinous material; The present invention provides a method comprising:

[0020] Other objects, features, aspects and advantages of the present invention will become more clearly apparent from reading the following description and examples.

[0021] Implementations of the present invention will now be described, by way of example only, with reference to the accompanying drawings, in which: [Brief explanation of the drawings]

[0022] [Figure 1] FIG. 1 shows the Raman spectrum of ferulic acid from 400 to 2000 cm −1 . [Figure 2] FIG. 1 shows the Raman spectrum of tocopherol from 400 to 2000 cm −1 . [Figure 3] FIG. 1 shows the penetration profile of ferulic acid and tocopherol for the composition of Inventive Example 5 after mixing with 48% by weight of water relative to the total weight of the resulting mixture (FA stands for ferulic acid and VE stands for tocopherol). [Figure 4] FIG. 1 shows the permeation profile of ferulic acid and tocopherol for the composition of Comparative Example 4 (FA means ferulic acid, VE means tocopherol). DETAILED DESCRIPTION OF THE INVENTION

[0023] Unless otherwise defined, all technical and scientific terms used herein have the same meaning as commonly understood by one of ordinary skill in the art to which this invention belongs. In the event that a definition of a term in this description conflicts with a meaning commonly understood by one of ordinary skill in the art to which this invention belongs, the definition set forth herein shall apply.

[0024] Hereinafter, unless otherwise indicated, the limits of ranges of values ​​are included within the ranges, in particular in the expressions "between" and "from."

[0025] Furthermore, the phrase "at least one" as used in this description is equivalent to the phrase "one or more."

[0026] Throughout this application, the term "comprising" should be interpreted to encompass all specifically mentioned features as well as optional, additional, unspecified features. As used herein, use of the term "comprising" also discloses embodiments in which no features are present other than those specifically mentioned (i.e., "consisting of").

[0027] Unless otherwise specified, all numbers expressing quantities of ingredients and the like used in the present description and claims should be understood to be modified by the term "about." Accordingly, unless indicated to the contrary, the numbers and parameters set forth herein are approximate values ​​that can be modified, if necessary, for desired purposes.

[0028] All percentages in this invention refer to weight percentages unless otherwise specified.

[0029] For the purposes of the present invention, the term "keratinous materials" is intended to include human skin, mucous membranes, such as the lips. The skin of the face is most particularly considered by the present invention.

[0030] "Anhydrous" means that no water is intentionally added and that the oil content of the composition is less than 0.5% by weight, based on the total weight of the composition. In particular, there is no water present in the composition.

[0031] The anhydrous composition according to the present invention comprises a) at least one cosmetically active ingredient that is sensitive to water and / or oxygen; b) at least one nonionic surfactant selected from polyglyceryl fatty acid esters having an HLB value of 13 or greater at a temperature of 25°C and ethoxylated / propoxylated fatty alcohols; and c) Dipropylene glycol Including, It does not contain any cationic surfactants.

[0032] beauty active ingredients According to a first aspect, the anhydrous composition according to the invention comprises at least one cosmetic active ingredient that is sensitive to water and / or oxygen.

[0033] Examples of cosmetic active ingredients that are sensitive to water and / or oxygen include ferulic acid, vitamins such as ascorbic acid and tocopherol.

[0034] Ferulic acid Ferulic acid has the CAS number 1135-24-6, is also known as 4-hydroxy-3-methoxycinnamic acid, and has the formula:

[0035] [ka]

[0036] Ferulic acid can be widely found in ferulic acid, coffee, apple, artichoke, peanut and orange seeds, and both the seeds and cell walls of daylilies (e.g., rice, wheat, oats and pineapple). Like many natural phenols, ferulic acid is a powerful antioxidant that is highly reactive to free radicals and reduces oxidative stress. Many studies suggest that ferulic acid may have antitumor activity.

[0037] Such a product can be, for example, ORYZA FERULIX manufactured by ORYZA OIL & FAT CHEMICAL.

[0038] When present, ferulic acid is present in an amount ranging from 0.01% to 5% by weight, preferably from 0.1% to 1.9% by weight, relative to the total weight of the composition.

[0039] Ascorbic acid Ascorbic acid has the following structural formula:

[0040] [ka]

[0041] Ascorbic acid can be extracted from various plant sources in which it naturally occurs, such as rose hips, blackcurrants, citrus fruit juice, and the mature fruit of Capsicum annuum L.

[0042] A typical synthetic procedure involves hydrogenating D-glucose to D-sorbitol, followed by oxidation using Acetobacter suboxydans to form L-sorbose. A carboxyl group is then added to C1 by air oxidation of the diacetone derivative of L-sorbose, and the resulting diacetone-2-keto-L-gluconic acid is converted to L-ascorbic acid by heating with hydrochloric acid.

[0043] An example of a commercially available ascorbic acid product is a product sold under the trade name YSA-SALICYLIC ACID PHARMACEUTICAL GRADE manufactured by NOVACYL.

[0044] When present, ascorbic acid is present in an amount ranging from 1% to 15% by weight, preferably from 8% to 12% by weight, relative to the total weight of the composition.

[0045] Tocopherol Tocopherol, also known as vitamin E, has the following formula (I):

[0046] [ka]

[0047] (In the formula, R1 is selected from hydrogen and methyl; R2 is selected from hydrogen and a methyl group; R3 is methyl It has the following structure.

[0048] There are four types of tocopherols (α, β, γ and δ-tocotrienol).

[0049] Alpha-tocotrienol has the following structure:

[0050] [ka]

[0051] That is, in formula (I), R1 is methyl, R2 is methyl, and R3 is methyl.

[0052] β-Tocotrienol has the following structure:

[0053] [ka]

[0054] That is, in formula (I), R1 is methyl, R2 is hydrogen, and R3 is methyl.

[0055] Gamma-tocotrienol has the following structure:

[0056] [ka]

[0057] That is, in formula (I), R1 is hydrogen, R2 is methyl, and R3 is methyl.

[0058] δ-Tocotrienol has the following structure:

[0059] [ka]

[0060] That is, in formula (I), R1 is hydrogen, R2 is hydrogen, and R3 is methyl.

[0061] Alpha-tocopherol is the only form of vitamin E that remains active in the human body and is therefore the form of vitamin E found in greatest amounts in blood and tissues.

[0062] An example of a commercially available tocopherol product is a product sold under the trade name DL ALPHA TOCOPHEROL (0410276) manufactured by DSM NUTRITIONAL PRODUCTS.

[0063] When present, the tocopherol is present in an amount ranging from 0.1% to 10% by weight, preferably from 0.1% to 5% by weight, relative to the total weight of the composition.

[0064] When tocopherol is present as a cosmetically active ingredient, the anhydrous composition preferably further comprises an oil selected from undecane, tridecane, C15-19 alkanes, isohexadecane, dicaprylyl ether, hydrogenated polyisobutene, and squalane in an amount ranging from 0.1% to 5% by weight, preferably from 0.5% to 2% by weight, relative to the total weight of the composition.

[0065] Nonionic surfactants According to a first aspect, the composition according to the invention comprises at least one nonionic surfactant chosen from polyglyceryl fatty acid esters having an HLB value of 13 or more at a temperature of 25°C and ethoxylated / propoxylated fatty alcohols.

[0066] Polyglyceryl fatty acid esters with an HLB value of 13 or higher The HLB (hydrophilic-lipophilic balance) value is defined according to the method of Griffin in J. Ploughshare. Cosm. Chem. 1954 (Vol. 5), pp. 249-256. In particular, the "HLB" value is related to the ratio of hydrophilic groups to lipophilic groups in a surfactant, and is also related to the solubility of the surfactant. Surfactants with a higher HLB are more soluble in hydrophilic systems.

[0067] Preferably, the polyglyceryl fatty acid esters are chosen from mono-, di- and triesters of glycerin with saturated or unsaturated fatty acids containing from 8 to 12 carbon atoms, such as lauric acid, capric acid and caprylic acid.

[0068] Preferably, the polyglyceryl fatty acid ester is PG2 caprate, PG2 dicaprate, PG2 tricaprate, PG2 caprylate, PG2 dicaprylate, PG2 tricaprylate, PG2 laurate, PG2 dilaurate, PG2 trilaurate, PG3 caprate, PG3 dicaprate, PG3 tricaprate, PG3 caprylate, PG3 dicaprylate, PG3 tricaprylate, PG3 laurate, PG3 dilaurate, PG3 trilaurate, PG4 caprate, PG4 caprate, PG4 tricaprate, PG4 caprylate, PG4 dicaprylate, PG4 tricaprylate, PG4 laurate, PG4 dilaurate, PG4 trilaurate, PG5 caprate, PG5 dicaprate, PG5 tricaprate, PG5 caprylate, PG5 dicaprylate, PG5 tricaprylate, PG5 laurate, PG5 dilaurate, PG5 trilaurate, PG6 caprate, PG6 dicaprate, PG6 tricaprate, PG6 caprylate, dicaprylic acid PG6, PG6 tricaprylate, PG6 laurate, PG6 dilaurate, PG6 trilaurate, PG7 caprate, PG7 dicaprate, PG7 tricaprate, PG7 caprylate, PG7 dicaprylate, PG7 tricaprylate, PG7 laurate, PG7 dilaurate, PG7 trilaurate, PG8 caprate, PG8 dicaprate, PG8 tricaprate, PG8 caprylate, PG8 dicaprylate, PG8 tricaprylate, PG8 laurate, PG8 dilaurate , PG8 trilaurate, PG9 caprate, PG9 dicaprate, PG9 tricaprate, PG9 caprylate, PG9 dicaprylate, PG9 tricaprylate, PG9 laurate, PG9 dilaurate, PG9 trilaurate, PG10 caprate, PG10 dicaprate, PG10 tricaprate, PG10 caprylate, PG10 dicaprylate, PG10 tricaprylate, PG10 laurate, PG10 dilaurate and PG10 trilaurate.

[0069] More preferably, the polyglyceryl fatty acid ester is selected from polyglyceryl caprylate, which has a polyglyceryl moiety derived from 2 to 10 glycerol units.

[0070] An example of polyglyceryl caprylate having a polyglyceryl moiety derived from 2 to 10 glycerol units is polyglyceryl-6 caprylate, such as the product sold by Taiyo Kagaku Co., Ltd. under the name SUNSOFT Q-8H-C.

[0071] When present, the polyglyceryl fatty acid ester is present in an amount ranging from 0.5% to 10% by weight, preferably from 1% to 5% by weight, more preferably from 1% to 4% by weight, relative to the total weight of the composition.

[0072] Ethoxylated / Propoxylated Fatty Alcohols Ethoxylated / propoxylated fatty alcohols are ethers formed from the reaction of fatty alcohols with propylene oxide and ethylene oxide.

[0073] Advantageously, the fatty alcohol is chosen from linear or branched C8 to C30 fatty alcohols, preferably C14 to C22 fatty alcohols.

[0074] Preferably, the ethoxylated / propoxylated fatty alcohols are selected from ethoxylated / propoxylated C14 to C22 fatty alcohols.

[0075] Preferably, the ethoxylated / propoxylated fatty alcohol is selected from ethoxylated / propoxylated C14-C22 fatty alcohols having 1-40 EO (ethylene oxide) units and 1-40 PO (propylene oxide) units.

[0076] Examples of ethoxylated / propoxylated fatty alcohols include PPG-1 Beheneth-15, PPG-12 Capryleth-18, PPG-2-Ceteareth-9, PPG-4-Ceteareth-12, PPG-10-Ceteareth-20, PPG-1-Ceteth-1, PPG-1-Ceteth-5, PPG-1-Ceteth-10, PPG-1-Ceteth-20, PPG-2-Ceteth-1, PPG-2-Ceteth-5, PPG PG-2-ceteth-10, PPG-2-ceteth-20, PPG-4-ceteth-1, PPG-4-ceteth-5, PPG-4-ceteth-10, PPG-4-ceteth-20, PPG-5-ceteth-20, PPG-8-ceteth-1, PPG-8-ceteth-2, PPG-8-ceteth-5, PPG-8-ceteth-10, PPG-8-ceteth-20, PPG-2 C12-13 Palace-8, PPG-2 C12-15 Palace-6, PPG-4 C13-15 Palace-15, PPG-5 C9-15 Palace-6, PPG-6 C9-11 Palace-5, PPG-6 C12-15 Palace-12, PPG-6 C12-18 Palace-11, PPG-3 C12-14Sec-Palace-7, PPG-4 C12-14Sec-Palace-5, PPG-5 C12-14Sec-Palace-7, PPG-5C12-14Sec-Pace-9, PPG-1-Deces-6, PPG-2-Deces-3, PPG-2-Deces-5, PPG-2-Deces-7, PPG-2-Deces-10, PPG-2-Deces-12, PPG-2-Deces-15, PPG-2-Deces-20, PPG-2-Deces-30, PPG-2-Deces-40, PPG-2-Deces-50, PPG-2-Deces-60, PPG-4-Deces-4, PPG-4-Deces-6, PPG-6-Deces PPG-6-deceth-4, PPG-6-deceth-9, PPG-8-deceth-6, PPG-14-deceth-6, PPG-6-decyltetradeceth-12, PPG-6-decyltetradeceth-20, PPG-6-decyltetradeceth-30, PPG-13-decyltetradeceth-24, PPG-20-decyltetradeceth-10, PPG-2-isodeceth-4, PPG-2-isodeceth-6, PPG-2-isodeceth-8, PPG-2-isodeceth-9, PPG-2 -Isodeceth-10, PPG-2-Isodeceth-12, PPG-2-Isodeceth-18, PPG-2-Isodeceth-25, PPG-4-Isodeceth-10, PPG-12-Laureth-50, PPG-2-Laureth-5, PPG-2-Laureth-8, PPG-2-Laureth-12, PPG-3-Laureth-8, PPG-3-Laureth-9, PPG-3-Laureth-10, PPG-3-Laureth-12, PPG-4 Laureth-2, PPG-4 Laureth -5, PPG-4 laureth-7, PPG-4-laureth-15, PPG-5-laureth-5, PPG-6-laureth-3, PPG-25-laureth-25, PPG-3-myreth-3, PPG-3-myreth-11, PPG-23-steareth-34, PPG-30 steareth-4, PPG-34-steareth-3, PPG-38 steareth-6, PPG-1 trideceth-6, PPG-4 trideceth-6 and PPG-6 trideceth-8.

[0077] When present, the ethoxylated / propoxylated fatty alcohol is present in an amount ranging from 1% to 10% by weight, preferably from 2% to 8% by weight, relative to the total weight of the composition.

[0078] Dipropylene Glycol According to a first aspect, the composition according to the invention comprises dipropylene glycol.

[0079] In the compositions according to the invention, dipropylene glycol is used as a co-surfactant and solvent.

[0080] Advantageously, dipropylene glycol is present in an amount ranging from 5% to 30% by weight and preferably from 5% to 20% by weight relative to the total weight of the composition.

[0081] C3~C6 polyols In some embodiments, the composition according to the present invention further comprises a C3-C6 polyol other than dipropylene glycol. Preferably, the C3-C6 polyol is selected from C3-C6 glycol and glycerin.

[0082] Examples of C3 to C6 glycols other than dipropylene glycol include propylene glycol, butylene glycol, pentylene glycol, hexylene glycol, PEG-6 and PEG-8.

[0083] In the present invention, the definition of glycol includes all possible isomers. For example, propylene glycol includes 1,3-propylene glycol, 1,2-propylene glycol, and 1,1-propylene glycol. Butylene glycol includes 1,4-butylene glycol, 1,3-butylene glycol, 1,2-butylene glycol, etc.

[0084] Preferably, the anhydrous composition according to the present invention comprises propylene glycol.

[0085] When present, the C3-C6 polyol other than dipropylene glycol is present in an amount ranging from 1% to 50% by weight, preferably from 10% to 40% by weight, based on the total weight of the composition.

[0086] Additional cosmetic active agents Depending on the final purpose, the composition may contain additional cosmetic active agents.

[0087] Examples of additional cosmetic active agents that may be used in the compositions of the invention that may be mentioned include enzymes, flavonoids, moisturizers, anti-inflammatory agents, pigment removers, whitening agents (e.g., phenylethyl resorcinol), alpha-hydroxy acids, beta-hydroxy acids (e.g., capryloyl salicylic acid), retinoids, antibacterial active agents, tensioning agents, ceramides, essential oils, UV filters (i.e., sunscreens), and mixtures thereof.

[0088] It is easy for one skilled in the art to adjust the amount of additional cosmetic active agent based on the end use of the composition according to the present invention.

[0089] Additional adjuvants or additives The compositions according to the invention may also contain conventional cosmetic adjuvants or additives, such as fragrances, preservatives and disinfectants, opacifiers, dyes, emollients, buffers, electrolytes such as sodium chloride, or pH adjusters (e.g., citric acid or potassium hydroxide), and mixtures thereof.

[0090] Needless to say, the skilled person will carefully select the optional adjuvants to be added to the compositions according to the invention so that the advantageous properties inherently associated with the compositions according to the invention are not or substantially not adversely affected by the envisaged addition.

[0091] According to a preferred embodiment, the invention relates to an anhydrous composition for caring for keratinous materials, comprising, relative to the total weight of the composition: a) at least one cosmetically active ingredient selected from ferulic acid, ascorbic acid, and tocopherol; b) 1% to 4% by weight of at least one nonionic surfactant selected from polyglyceryl caprylate having polyglyceryl moieties derived from 2 to 10 glycerol units and ethoxylated / propoxylated C14 to C22 fatty alcohols having 1 to 40 EO units and 1 to 40 PO units; and c) 5% to 20% by mass of dipropylene glycol Including, The composition is provided without any cationic surfactants.

[0092] Galenic forms and uses The composition according to the invention can be an anhydrous product, which the consumer can mix with water or an aqueous system to obtain a microemulsion.

[0093] Alternatively, the composition according to the invention can be part of a dual chamber product, in which the composition according to the invention is in one chamber and a homogeneous aqueous formulation is in the other chamber, allowing the consumer to mix the composition in one chamber with the homogeneous aqueous formulation in the other chamber to obtain a microemulsion.

[0094] "Microemulsion" can be defined in two ways, that is, in the broad sense and the narrow sense. In one case ("narrow sense microemulsion"), microemulsion refers to a thermodynamically stable isotropic single liquid phase containing a three-component system having three components: an oil component, an aqueous component, and a surfactant. In the other case ("broad sense microemulsion"), microemulsion additionally includes emulsions that appear transparent or translucent due to smaller particle sizes among typical thermodynamically unstable emulsion systems (Satoshi Tomomasa et al., Oil Chemistry, Vol. 37, No. 11 (1988), pp. 48-53). "Microemulsion" as used herein refers to "broad sense microemulsion."

[0095] Advantageously, in the microemulsions formed by the compositions according to the invention, the droplets have a number average size of less than or equal to 120 nm, preferably between 20 nm and 80 nm, more preferably between 20 nm and 50 nm.

[0096] The volume-average droplet size can be determined by the well-known method of dynamic light scattering (DLS). A suitable instrument for this determination is the Malvern Zetasizer Nano ZS particle size analyzer, equipped with a standard laser at 633 nm wavelength with a power output of 4 mW. This instrument is also equipped with a correlator (25 ns to 8000 s, up to 4000 channels).

[0097] Microemulsions obtained by combining anhydrous compositions with water or aqueous systems can be used to care for keratinous materials.

[0098] Thus, according to a second aspect, the present invention provides a non-therapeutic method for caring for keratinous materials, comprising: i) mixing an anhydrous composition according to the present invention with water or an aqueous system to form a microemulsion; and ii) applying the microemulsion to the keratinous material; The present invention provides a method comprising:

[0099] The aqueous system may be any system that contains 40% or more by weight of water relative to the total weight of the system.

[0100] The following examples are intended to illustrate compositions according to the present invention, but are not intended to limit the scope of the invention in any way. [Example]

[0101] The main raw materials used, their trade names and suppliers are listed in Table 1.

[0102] [Table 1]

[0103] (Examples 1 to 5 and Comparative Examples 1 to 3 of the present invention) Compositions according to Examples (IE) 1 to 5 and Comparative Examples (CE) 1 to 3 of the present invention were prepared according to the contents given in Table 2 (Table 2) (the contents are expressed as mass percentages of the active material with respect to the total mass of each composition, unless otherwise indicated).

[0104] [Table 2]

[0105] Preparation procedure Taking the composition of Example 1 of the present invention as an example, the composition was prepared as follows. 1). Ferulic acid was introduced into dipropylene glycol and gently stirred until no visible particles remained to obtain a mixture. 2). Polyglyceryl-6 caprylate was introduced into the mixture and stirring was continued. 3). 1,3-Propylene glycol and 1,2-propylene glycol were introduced and stirred to obtain the composition.

[0106] Evaluation 1. Stability The stability of each composition obtained in Examples 1 to 5 and Comparative Examples 1 to 3 of the present invention was evaluated as follows.

[0107] After preparation, each composition was placed at room temperature (20 °C) for 2 months, and then the stability of each composition was determined by sensing the presence or absence of odor generation and observing the presence or absence of color change.

[0108] If there is no odor generation and no color change in the composition after the composition is placed at room temperature (20 °C) for 2 months, the composition passes the stability test. If there is odor generation and / or color change in the composition after the composition is placed at room temperature (20 °C) for 2 months, the composition fails the stability test.

[0109] The results were listed in Table 3 (Table 3).

[0110] 2. Particle size Each composition prepared in Examples 1 to 5 and Comparative Examples 1 to 3 of the present invention was mixed with water by gently mixing, and then the particle size of the droplets in the resulting mixture was determined through Brookhaven DLS at a scattering angle of 90 (°) and a counting rate of 355.1 kcps. The stability was evaluated using the following criteria.

[0111] When the particle size (average diameter by volume) is 120 nm or more, no microemulsion is formed.

[0112] When the particle size (average diameter by volume) is more than 10 nm and less than 120 nm, a microemulsion is formed.

[0113] Whether a microemulsion was formed or not was listed in Table 3 (Table 3).

[0114]

Table 3

[0115] It was found that the particle size of all the droplets in each composition of Examples 1 to 5 of the present invention was within 40 nm.

[0116] 3. Bioavailability The penetration of the beauty active ingredient in each composition prepared in Example 1 was characterized as follows.

[0117] i) Preparation of skin tissue samples 6 μl of each composition to be tested was uniformly applied to 0.8 cm × 0.8 cm porcine skin (skin of porcine ear from the food industry) (9 mg / cm 2(corresponding to 0.01g). The pig skin samples were then placed on an insert membrane with PBS underneath, followed by incubation at 37°C and 95% RH for 2 hours. The treated samples were embedded in OCT tissue freezing medium, then frozen and cryosectioned to a thickness of 20 μm. They were then mounted on CaF2 substrates for Raman confocal scanning. Three pig samples were prepared for each composition. Raman confocal mapping was obtained for each treated sample.

[0118] ii) Raman spectroscopy A LabRam HR Evolution (Horiba Jobin-Yvon, Villeneuve-d'Ascq, France) Raman confocal microscope was used. Raman spectra were obtained for the samples using a 532 nm DPSS laser with an 8 mW output power coupled with a ×50 LM Plan objective (Olympus, NA 0.75, Rungis, France). For all measurements, the confocal hole was set to a diameter of 100 μm. Prior to testing, the silicon 520.7 cm -1 The system was spectrally calibrated to the spectral lines of A 600 lines / mm grating was used to facilitate detection by dispersing the Raman-shifted radiation onto a charge-coupled device (CCD) detector.

[0119] For pure cosmetic active ingredients, 400-2000 cm was measured using 25% laser intensity and a 10-second acquisition time. -1 Single point spectra were acquired over a spectral range of .

[0120] For mapping in sample evaluation, the step size was 3 μm in both the X and Y directions. The acquisition area was 18 × 150 μm. For each spot, a laser intensity of 50% and an acquisition time of 5 seconds per spectrum were used. The spectral range was 400–2000 cm. -1 It was.

[0121] iii) Data analysis Non-negative constrained least squares (NCLS) analysis was performed using Matlab. Prior to statistical analysis, the Raman spectra were subjected to linear baseline correction. For analysis, the 400–2000 cm region of the cosmetic active ingredients was used. -1 The fingerprint spectrum was used.

[0122] Figure 1 shows the 400-2000 cm peak for ferulic acid. -1 4 shows the Raman spectrum of

[0123] Figure 2 shows the 400-2000 cm peak for tocopherol. -1 4 shows the Raman spectrum of

[0124] The simplified description of the NCLS results can be defined as follows: Ss= (SR1*C1)+(SR2*C2)+……+(SRi*Ci)+R*CR Ss: Raman signal of one pixel acquired for the treated pig skin sample SRi: Raman signals of each hypothetical component (PCA component) in untreated pigs R: Raman signal of pure cosmetic active ingredients Ci: Coefficients of each hypothesized component (PCA component) at the exact pixel CR: Coefficient of cosmetic active ingredients at exact pixel

[0125] The calculated coefficient index of the active ingredient can be used to generate a distribution profile of the active ingredient from the stratum corneum of the outer skin to the deeper dermal portion.

[0126] FIG. 3 shows the penetration profile of ferulic acid and tocopherol for the composition of Inventive Example 5 after mixing with 48% by weight of water relative to the total weight of the resulting mixture (FA stands for ferulic acid and VE stands for tocopherol).

[0127] FIG. 4 shows the permeation profile of ferulic acid and tocopherol for the composition of Comparative Example 4 (FA stands for ferulic acid and VE stands for tocopherol).

[0128] 3 and 4, it can be seen that in the case of the composition according to Example 5 of the present invention, tocopherol and ferulic acid penetrate deeper than in the composition according to Comparative Example 4.

Claims

1. a) at least one cosmetically active ingredient sensitive to water and / or oxygen selected from ferulic acid, ascorbic acid and tocopherol; b) at least one nonionic surfactant selected from polyglyceryl fatty acid esters having an HLB value of 13 or greater at a temperature of 25°C and ethoxylated / propoxylated fatty alcohols; c) dipropylene glycol, and d) C3-C6 glycols other than dipropylene glycol 1. An anhydrous composition for caring for keratinous materials, comprising: the polyglyceryl fatty acid ester is polyglyceryl caprylate, and the ethoxylated / propoxylated fatty alcohol is an ethoxylated / propoxylated C14-C22 fatty alcohol; When present, ferulic acid is present in an amount ranging from 0.01% to 5% by weight, relative to the total weight of the composition; When present, the ascorbic acid is present in an amount ranging from 1% to 15% by weight, relative to the total weight of the composition; When present, the tocopherol is present in an amount ranging from 0.1% to 10% by weight, relative to the total weight of the composition; When present, the polyglyceryl fatty acid ester is present in an amount ranging from 0.5% to 10% by weight, relative to the total weight of the composition; When present, the ethoxylated / propoxylated fatty alcohol is present in an amount ranging from 1% to 10% by weight, relative to the total weight of the composition; dipropylene glycol is present in an amount ranging from 5% to 30% by weight, relative to the total weight of the composition; the C3-C6 glycol other than dipropylene glycol is present in an amount ranging from 1% to 50% by weight, based on the total weight of the composition; A composition, wherein the composition does not contain any cationic surfactants.

2. 2. The composition according to claim 1, wherein the polyglyceryl fatty acid ester is selected from mono-, di-, and triesters of glycerin and caprylic acid.

3. 2. The composition of claim 1, wherein the polyglyceryl fatty acid ester is selected from polyglyceryl caprylate having a polyglyceryl moiety derived from 2 to 10 glycerol units.

4. 4. The composition according to claim 1, wherein the ethoxylated / propoxylated fatty alcohol is selected from ethoxylated / propoxylated C14-C22 fatty alcohols having 1 to 40 EO units and 1 to 40 PO units.

5. A composition described in any one of claims 1 to 4, wherein the C3 to C6 glycol other than dipropylene glycol is selected from propylene glycol, butylene glycol, pentylene glycol and hexylene glycol.

6. relative to the total mass of the composition, a) at least one cosmetically active ingredient selected from ferulic acid, ascorbic acid, and tocopherol; b) 1% to 4% by weight of at least one nonionic surfactant selected from polyglyceryl caprylate having polyglyceryl moieties derived from 2 to 10 glycerol units and ethoxylated / propoxylated C14 to C22 fatty alcohols having 1 to 40 EO units and 1 to 40 PO units; and c) 5% to 20% by weight of dipropylene glycol Including, 10. The composition of claim 1, which does not contain any cationic surfactants.

7. A non-therapeutic method for caring for keratinous materials, comprising: i) mixing the anhydrous composition according to any one of claims 1 to 6 with water or an aqueous system to form a microemulsion; and ii) applying the microemulsion to the keratinous material; A method comprising:

Citation Information

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