Composition including skin care active ingredient

JP2024010435A5Pending Publication Date: 2025-07-23LOREAL SA
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Patent Information

Application Number
JP2022111767
Authority / Receiving Office
JP · JP
Patent Type
Applications
Current Assignee / Owner
Filing Date
2022-07-12
Publication Date
2025-07-23

AI Technical Summary

Technical Problem

There is a need for compositions that enhance the penetration of skin care active ingredients into the skin, as the barrier function of the skin makes it difficult for these ingredients to be absorbed effectively.

Method used

A composition comprising at least one oil, at least one diol with a carbon chain of three or more carbon atoms, at least one skin care active ingredient, and water, which includes specific types of oils and diols to improve skin penetration.

Benefits of technology

The composition enhances the penetration of skin care active ingredients, providing better cosmetic effects such as enhanced skin brightness and a refreshing, less greasy texture, while maintaining stability and reducing skin irritation.

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Abstract

To provide a composition that can enhance or improve the permeation of a skin care active ingredient into the skin.SOLUTION: The present invention relates to a composition that contains (a) at least one oil, (b) at least one diol with at least one carbon chain including three or more carbon atoms, (c) at least one skin care active ingredient, and (d) water. The inventive composition can enhance or improve the permeation of the component (c) into the skin compared to when the component (b) is not used.SELECTED DRAWING: None
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Description

[Technical Field]

[0001] The present invention relates to a composition, preferably a cosmetic composition, more preferably a dermocosmetic composition, comprising at least one skin care active ingredient. [Background technology]

[0002] There is a wide variety of skin care active ingredients used in the field of cosmetic and dermatological compositions.

[0003] It is preferable that skin care active ingredient can be absorbed or penetrate into skin as much as possible.However, due to the barrier function of skin, the skin absorption or skin penetration of this skin care active ingredient is not easy.Therefore, one possible way to enhance the skin penetration of skin care active ingredient can be to use skin penetration enhancer together with skin care active ingredient.

[0004] For example, WO2018 / 097303 uses a combination of a single polyglyceryl fatty acid ester and niacinamide in a nanoemulsion or microemulsion containing ceramide to enhance the skin penetration of the ceramide. [Prior art documents] [Patent documents]

[0005] [Patent Document 1] WO2018 / 097303 [Patent Document 2] EP-A-0 487 404 [Patent Document 3] EP-A-0 425 066 [Patent Document 4] Japanese Patent Publication No. 05-213736 [Patent Document 5] EP 0 667 145 [Patent Document 6] EP 1 430 883 [Patent Document 7] WO 02 / 051 828 [Patent Document 8] U.S. Patent No. 4,131,576 [Non-patent literature]

[0006] [Non-Patent Document 1] Walter Noll, Chemistry and Technology of Silicones (1968), Academic Press. [Non-patent document 2] Cosmetics and Toiletries, Vol. 91, January 1976, pp. 27-32, Todd & Byers, Volatile Silicone Fluids for Cosmetics [Non-patent document 3] Meylan and Howard, Atom / Fragment contribution method for estimating octanol-water partition coefficients, J. Pharm. Sci., 84: 83-92, 1995 [Non-patent document 4] Exploring QSAR: hydrophobic, electronic and steric constants (ACS professional reference book, 1995) [Non-patent document 5] http: / / esc.syrres.com / interkow / kowdemo.htm Summary of the Invention [Problem to be solved by the invention]

[0007] There remains a need for compositions containing skin care actives that can enhance or improve the penetration of the skin care actives into the skin based on novel skin penetration enhancers.

[0008] It is an object of the present invention to provide a composition that can enhance or improve the penetration of skin care active ingredients into the skin. [Means for solving the problem]

[0009] The above object of the present invention is to (a) at least one oil; (b) at least one diol having at least one carbon chain containing three or more carbon atoms; (c) at least one skin care active ingredient; (d) Water and This can be achieved by a composition comprising:

[0010] (a) The oil may be selected from the group consisting of (i) fatty alcohols, (ii) fatty acids, (iii) monocarboxylic acid monoesters, (iv) dicarboxylic acid diesters, (v) N-acyl amino acid esters, and (vi) alkyl lactates, with the proviso that: - (i) the fatty alcohol and (ii) the fatty acid each contain a branched alkyl group or a linear or branched alkenyl group having from 4 to 30, preferably from 5 to 26, more preferably from 6 to 22 carbon atoms; - (iii) the monocarboxylic acid monoesters each contain a branched alkyl group or a linear or branched alkenyl group having 4 to 30, preferably 5 to 26, more preferably 6 to 22 carbon atoms, - (iv) the dicarboxylic acid diester comprises at least one branched alkyl group having 3 to 10, preferably 3 to 8, more preferably 3 to 6 carbon atoms, and an alkylene group having 6 to 18, preferably 6 to 14, more preferably 6 to 10 carbon atoms, (v) N-acylamino acid esters contain a branched alkyl group having 3 to 10, preferably 3 to 8, more preferably 3 to 6 carbon atoms, and a linear or branched acyl group having 4 to 30, preferably 5 to 26, more preferably 6 to 22 carbon atoms, - (vi) The alkyl lactate comprises a linear or branched alkyl group or a linear or branched alkenyl group, each having 4 to 30, preferably 5 to 26, more preferably 6 to 22 carbon atoms.

[0011] The (a) oil may comprise (v) an N-acylamino acid ester containing at least a branched alkyl group having 3 to 10, preferably 3 to 8, more preferably 3 to 6 carbon atoms, preferably a compound represented by the following general formula (5): R 2 -N(R 5 )-CH(R 6 )-(CH2) n -COO-R 3 (5) (In the formula, R 2 represents a linear or branched acyl group having 4 to 30, preferably 5 to 26, and more preferably 6 to 22 carbon atoms; R 3 represents a branched alkyl group having 3 to 10, preferably 3 to 8, more preferably 3 to 6 carbon atoms; R 5 represents a hydrogen atom or a linear or branched alkyl group having 1 to 4 carbon atoms; R 6 represents a hydrogen atom or a linear or branched alkyl group having 1 to 4 carbon atoms which may be substituted by a hydroxy group or a phenyl group; n represents an integer from 0 to 2. and the N-acyl amino acid ester may be selected from N-acyl amino acid esters represented by More preferably, the (a) oil is isopropyl lauroyl sarcosinate.

[0012] The amount of (a) oil in the composition according to the present invention may be in the range of 0.5% to 25% by mass, preferably 1% to 20% by mass, more preferably 2% to 15% by mass, relative to the total mass of the composition.

[0013] (b) The diol having at least one carbon chain containing three or more carbon atoms may be selected from the group consisting of propylene glycol, dipropylene glycol, polypropylene glycol, butylene glycol, dibutylene glycol, polybutylene glycol, pentylene glycol, dipentylene glycol, hexylene glycol, dihexylene glycol, and mixtures thereof.

[0014] The mass ratio of the amount of (b) diol having at least one carbon chain containing 3 or more carbon atoms to the amount of (a) oil can be 4 or more, preferably 5 or more, and more preferably 6 or more.

[0015] (c) The skin care active ingredient may have a Log P value of 4 or less, preferably from -4.5 to 4.0, more preferably from -4.0 to 3.5.

[0016] (c) The skin care active ingredient may be a skin care cosmetic active ingredient, preferably a skin whitening or anti-wrinkle ingredient, and more preferably may be selected from the group consisting of ascorbyl glucoside, 3-O-ethyl ascorbic acid, tranexamic acid, hydroxypropyltetrahydropyrantriol, niacinamide, salicylic acid, phenylethyl resorcinol, and mixtures thereof.

[0017] The amount of (c) skin care active ingredient in the composition according to the present invention may be in the range of 0.01% to 25% by weight, preferably 0.05% to 20% by weight, more preferably 0.1% to 15% by weight, relative to the total weight of the composition.

[0018] Compositions according to the present invention may have a turbidity of 120 NTU or less, preferably 90 NTU or less, more preferably 60 NTU or less.

[0019] The composition according to the present invention may be a cosmetic composition, preferably a skin cosmetic composition, more preferably a skin care cosmetic composition.

[0020] The present invention also relates to a cosmetic method for treating keratinous materials, preferably skin, comprising the step of applying a composition according to the invention. DETAILED DESCRIPTION OF THE INVENTION

[0021] After extensive research, the present inventors have discovered that by using a novel skin penetration enhancer, it is possible to provide a composition that can enhance or improve the penetration of skin care active ingredients into the skin.

[0022] Therefore, the present invention provides (a) at least one oil; (b) at least one diol having at least one carbon chain containing three or more carbon atoms; (c) at least one skin care active ingredient; (d) Water and The present invention relates to a composition comprising:

[0023] The compositions according to the present invention can enhance or improve the penetration of (c) a skin care active ingredient into the skin compared to when component (b) is not used.

[0024] (b) at least one diol having at least one carbon chain containing three or more carbon atoms can function as (c) a skin penetration enhancer for skin care active ingredients.

[0025] The composition according to the invention comprises at least one oil and is therefore capable of enhancing the brightness of the skin when applied to the skin.

[0026] The compositions according to the present invention can contain a relatively large amount of oil, and therefore can provide better cosmetic benefits derived from a relatively large amount of oil, such as enhanced skin lightening.

[0027] When the composition according to the present invention further comprises (e) at least one cellulose compound, the composition according to the present invention can further enhance skin lightening.

[0028] The composition according to the present invention can also provide a refreshing texture when used, and therefore a less greasy texture.

[0029] The composition according to the present invention can be stable over time even under temperature changes, for example from hot to cold and vice versa, so that it does not undergo any phase separation and maintains a uniform appearance.

[0030] Compositions according to the present invention may be transparent or slightly translucent, but are preferably transparent.

[0031] The composition according to the present invention does not need to contain any surfactant.Therefore, the amount of surfactant in the composition can be limited, for example, it can be 1% by weight or less, preferably 0.1% by weight or less, more preferably 0.01% by weight or less, based on the total weight of the composition.Most preferably, the composition according to the present invention does not contain surfactant.

[0032] It is well known that surfactants can provide a greasy texture and irritation to the skin.

[0033] Thus, when the composition according to the present invention comprises only limited amounts of surfactants, the composition according to the present invention can provide an even less greasy texture.

[0034] In addition, when the composition according to the present invention contains only a limited amount of surfactant, the composition according to the present invention can cause less irritation to the skin.

[0035] The compositions according to the invention are described in more detail below.

[0036] [oil] The composition according to the present invention may comprise (a) at least one oil. If two or more oils are used, they may be the same or different.

[0037] Here, "oil" means a fatty compound or substance in the form of a liquid or paste (non-solid) at atmospheric pressure (760 mmHg) and room temperature (25°C). As oils, those commonly used in cosmetics can be used alone or in combination. These oils can be volatile or non-volatile.

[0038] (a) The oil may be a non-polar oil such as a hydrocarbon oil or a silicone oil; a polar oil such as a vegetable oil or an animal oil, and an ester oil or an ether oil; or a mixture thereof.

[0039] (a) The oil may be selected from the group consisting of oils of vegetable or animal origin, synthetic oils, silicone oils, hydrocarbon oils, and fatty alcohols.

[0040] Examples of vegetable oils include linseed oil, camellia oil, macadamia nut oil, corn oil, mink oil, olive oil, avocado oil, camellia oil, castor oil, safflower oil, jojoba oil, sunflower oil, almond oil, rapeseed oil, sesame oil, soybean oil, peanut oil, and mixtures thereof.

[0041] Examples of animal oils include squalene and squalane.

[0042] Examples of synthetic oils include alkane oils such as isododecane and isohexadecane, ester oils, ether oils, and artificial triglycerides.

[0043] The ester oil is preferably a saturated or unsaturated, linear or branched C1-C 26 Aliphatic mono- or polyacids and saturated or unsaturated, linear or branched C1-C 26They are liquid esters with aliphatic monohydric or polyhydric alcohols, and the total number of carbon atoms in these esters is 10 or more.

[0044] Preferably, in the case of esters of monohydric alcohols, at least one of the alcohol and acid from which the esters of the present invention are derived is branched.

[0045] Among the monoesters of monoacids and monohydric alcohols, mention may be made of ethyl palmitate, ethylhexyl palmitate, isopropyl palmitate, dicaprylyl carbonate, alkyl myristates such as isopropyl myristate or ethyl myristate, isocetyl stearate, 2-ethylhexyl isononanoate, isononyl isononanoate, isodecyl neopentanoate and isostearyl neopentanoate.

[0046] C4~C 22 Dicarboxylic or tricarboxylic acids and C1-C 22 Esters of alcohols and monocarboxylic, dicarboxylic or tricarboxylic acids with non-sugar C4-C 26 Esters with dihydroxy, trihydroxy, tetrahydroxy or pentahydroxy alcohols may also be used.

[0047] Mention may especially be made of diethyl sebacate, isopropyl lauroyl sarcosinate, diisopropyl sebacate, bis(2-ethylhexyl) sebacate, diisopropyl adipate, di-n-propyl adipate, dioctyl adipate, bis(2-ethylhexyl) adipate, diisostearyl adipate, bis(2-ethylhexyl) maleate, triisopropyl citrate, triisocetyl citrate, triisostearyl citrate, glyceryl trilactate, glyceryl trioctanoate, trioctyldodecyl citrate, trioleyl citrate, neopentyl glycol diheptanoate, diethylene glycol diisononanoate.

[0048] As ester oil, C6-C 30 , preferably C 12 ~C22 Sugar esters and diesters of fatty acids can also be used. It should be remembered that the term "sugar" refers to an oxygen-bearing hydrocarbon-based compound containing several alcohol functional groups, with or without aldehyde or ketone functional groups, and containing at least four carbon atoms. These sugars can be monosaccharides, oligosaccharides, or polysaccharides.

[0049] Examples of suitable sugars that may be mentioned include sucrose (or saccharose), glucose, galactose, ribose, fucose, maltose, fructose, mannose, arabinose, xylose and lactose, as well as derivatives thereof, especially alkyl derivatives, such as methyl derivatives, e.g. methylglucose.

[0050] Sugar esters of fatty acids are, in particular, those made by esterifying the aforementioned sugars with linear or branched, saturated or unsaturated C6-C 30 , preferably C 12 ~C 22 They may be selected from the group comprising esters or mixtures of esters with fatty acids. When these compounds are unsaturated, they may have 1 to 3 conjugated or non-conjugated carbon-carbon double bonds.

[0051] The esters according to this variant may also be chosen from monoesters, diesters, triesters, tetraesters and polyesters, and mixtures thereof.

[0052] These esters may be, for example, oleate, laurate, palmitate, myristate, behenate, coconut, stearate, linoleate, linolenate, caprate and arachidonic acid esters, or mixtures thereof, such as, inter alia, mixed esters of oleopalmitate, oleostearate and palmitostearate, and pentaerythrityl tetraethylhexanoate.

[0053] More particularly, monoesters and diesters are used, especially the mono- or dioleate, stearate, behenate, oleopalmitate, linoleate, linolenate and oleostearate of sucrose, glucose or methylglucose.

[0054] An example that may be mentioned is the product sold under the name Glucate® DO by the company Amerchol, which is a methylglucose dioleate.

[0055] Examples of preferred ester oils include diisopropyl adipate, dioctyl adipate, 2-ethylhexyl hexanoate, ethyl laurate, cetyl octanoate, octyldodecyl octanoate, isodecyl neopentanoate, myristyl propionate, 2-ethylhexyl 2-ethylhexanoate, 2-ethylhexyl octanoate, 2-ethylhexyl caprylate / caprate, methyl palmitate, ethyl palmitate, isopropyl palmitate, dicarbonate, Examples of suitable glyceryl stearate include purilyl, isopropyl lauroyl sarcosine, isononyl isononanoate, ethylhexyl palmitate, isohexyl laurate, hexyl laurate, isocetyl stearate, isopropyl isostearate, isopropyl myristate, isodecyl oleate, glyceryl tri(2-ethylhexanoate), pentaerythrityl tetra(2-ethylhexanoate), 2-ethylhexyl succinate, diethyl sebacate, and mixtures thereof.

[0056] Examples of artificial triglycerides include caprylic / caprylyl glyceride, glyceryl trimyristate, glyceryl tripalmitate, glyceryl trilinolenate, glyceryl trilaurate, glyceryl tricaprate, glyceryl tricaprylate, capric / caprylic triglyceride, and capric / caprylic / linolenic triglyceride.

[0057] Examples of silicone oils include linear organopolysiloxanes such as dimethylpolysiloxane, methylphenylpolysiloxane, and methylhydrogenpolysiloxane, cyclic organopolysiloxanes such as cyclohexasiloxane, octamethylcyclotetrasiloxane, decamethylcyclopentasiloxane, and dodecamethylcyclohexasiloxane, and mixtures thereof.

[0058] Preferably, the silicone oil is chosen from liquid polydialkylsiloxanes, especially liquid polydimethylsiloxanes (PDMS), and liquid polyorganosiloxanes containing at least one aryl group.

[0059] These silicone oils may also be organically modified. The organically modified silicones that can be used according to the present invention are silicone oils as defined above, which contain one or more organic functional groups in their structure that are bonded via hydrocarbon-based groups.

[0060] Organopolysiloxanes are more fully defined in Walter Noll, Chemistry and Technology of Silicones (1968), Academic Press, Inc. They may be volatile or nonvolatile.

[0061] If volatile, the silicones are more particularly chosen from those having a boiling point between 60° C. and 260° C., and even more particularly chosen from: (i) Cyclic polydialkylsiloxanes containing 3 to 7, preferably 4 to 5, silicon atoms, such as octamethylcyclotetrasiloxane, sold in particular under the names Volatile Silicone® 7207 by Union Carbide or Silbione® 70045 V2 by Rhodia, decamethylcyclopentasiloxane, sold in particular under the names Volatile Silicone® 7158 by Union Carbide and Silbione® 70045 V5 by Rhodia, and dodecamethylcyclopentasiloxane, sold in particular under the name Silsoft 1217 by Momentive Performance Materials, and mixtures thereof. Cyclocopolymers of the dimethylsiloxane / methylalkylsiloxane type, such as those of the formula:

[0062] [ka]

[0063] Mention may also be made of Silicone Volatile® FZ 3109 sold by the company Union Carbide, of

[0064] Also included are mixtures of cyclic polydialkylsiloxanes and organosilicon compounds, such as a 50 / 50 mixture of octamethylcyclotetrasiloxane and tetratrimethylsilylpentaerythritol, and a mixture of octamethylcyclotetrasiloxane and oxy-1,1'-bis(2,2,2',2',3,3'-hexatrimethylsilyloxy)neopentane. (ii) Contains 2 to 9 silicon atoms and has a density of 5 × 10 at 25 °C -6 m 2Linear, volatile polydialkylsiloxanes with a viscosity of less than 1 / s. An example is decamethyltetrasiloxane, sold in particular by Toray Silicone under the name SH 200. Silicones belonging to this category are also described in an article published by Todd & Byers in Cosmetics and Toiletries, Vol. 91, January 1976, pp. 27-32, Volatile Silicone Fluids for Cosmetics. The viscosity of the silicones is measured at 25°C according to ASTM Standard 445, Appendix C.

[0065] Non-volatile polydialkylsiloxanes may also be used, these being more particularly chosen from polydialkylsiloxanes, among which mention may be made primarily of polydimethylsiloxanes containing trimethylsilyl end groups.

[0066] Among these polydialkylsiloxanes, mention may be made, but is not limited to, the following commercially available products: Silbione® oils of the 47 and 70 047 series or Mirasil® oils sold by the company Rhodia, for example oil 70 047 V 500 000, oils of the Mirasil® series sold by the company Rhodia; - Dow Corning 200 series oils, e.g. 60 000mm 2 DC200 having a viscosity of 1 / s, and Viscasil® oils manufactured by General Electric and certain oils of the SF series manufactured by General Electric (SF 96, SF 18).

[0067] Mention may also be made of polydimethylsiloxanes containing dimethylsilanol end groups, known under the name dimethiconol (CTFA), such as the 48 series oils from Rhodia.

[0068] Among the silicones containing aryl groups, mention may be made of polydiarylsiloxanes, especially polydiphenylsiloxanes, and polyalkylarylsiloxanes, such as phenylsilicone oils.

[0069] Phenylsilicone oils are those having the following formula:

[0070] [ka]

[0071] (In the formula, R1~R 10 are, independently of one another, saturated or unsaturated, linear, cyclic or branched C1-C 30 Hydrocarbon groups, preferably C1-C 12 a hydrocarbon group, more preferably a C1 to C6 hydrocarbon group, in particular a methyl, ethyl, propyl or butyl group; m, n, p, and q each independently represent an integer of 0 to 900 (inclusive), preferably an integer of 0 to 500 (inclusive), more preferably an integer of 0 to 100 (inclusive); However, the sum n+m+q is not 0.) The phenyl silicones may be selected from the following:

[0072] Examples that may be mentioned include products sold under the following names: Silbione® oils from Rhodia, 70 641 series; oils of the Rhodorsil® 70 633 and 763 series from the company Rhodia; - Dow Corning 556 Cosmetic Grade Fluid, - PK series silicones from Bayer, e.g. product PK20, Certain oils of the SF series manufactured by General Electric, such as SF 1023, SF 1154, SF 1250 and SF 1265.

[0073] Phenyl silicone oils include phenyl trimethicone (R1 to R2 in the above formula). 10 is methyl, p, q and n=0, and m=1).

[0074] The organically modified liquid silicones may contain, inter alia, polyethyleneoxy and / or polypropyleneoxy groups. Mention may therefore be made of silicone KF-6017 proposed by Shin-Etsu Chemical Co., Ltd., and the oils Silwet® L722 and L77 manufactured by Union Carbide.

[0075] The hydrocarbon oil may be selected from: - Linear or branched, optionally cyclic C6-C 16 Lower alkanes. Examples that may be mentioned include hexane, undecane, dodecane, tridecane and isoparaffins, such as isohexadecane, isododecane and isodecane. - linear or branched hydrocarbons containing more than 16 carbon atoms, such as liquid paraffin, liquid petroleum jelly, polydecene and hydrogenated polyisobutenes, such as Parleam®, and squalane.

[0076] Preferred examples of hydrocarbon oils include linear or branched hydrocarbons such as isohexadecane, isododecane, squalane, mineral oils (e.g., liquid paraffin), paraffin, Vaseline or petrolatum, and naphthalene; hydrogenated polyisobutene, isoeicosane, and decene / butene copolymers; and mixtures thereof.

[0077] The term "aliphatic" in aliphatic alcohols refers to a relatively large number of carbon atoms. Thus, alcohols having 4 or more, preferably 6 or more, and more preferably 12 or more carbon atoms are included within the scope of aliphatic alcohols. Fatty alcohols can be saturated or unsaturated. Fatty alcohols can be linear or branched.

[0078] The aliphatic alcohol may have the structure R-OH, where R is selected from saturated and unsaturated, linear and branched groups containing from 4 to 40 carbon atoms, preferably from 6 to 30 carbon atoms, and more preferably from 12 to 20 carbon atoms. In at least one embodiment, R is selected from C 12 ~C 20 Alkyl groups and C 12 ~C 20 R may be selected from the group consisting of alkyl, aryl ...

[0079] Examples of fatty alcohols include lauryl alcohol, cetyl alcohol, stearyl alcohol, isostearyl alcohol, behenyl alcohol, undecylenyl alcohol, myristyl alcohol, octyldodecanol, hexyldecanol, oleyl alcohol, linoleyl alcohol, palmitoleyl alcohol, arachidonyl alcohol, erucyl alcohol, and mixtures thereof.

[0080] Preferably, the fatty alcohol is a saturated fatty alcohol.

[0081] Thus, fatty alcohols are linear or branched, saturated or unsaturated C6-C 30 Alcohols, preferably linear or branched, saturated C6-C 30 Alcohols, more preferably linear or branched saturated C 12 ~C 20 The alcohol may be selected from:

[0082] The term "saturated fatty alcohol" as used herein means an alcohol having a long, saturated aliphatic carbon chain. A saturated fatty alcohol is any linear or branched, saturated C-C 30 Preferably, the alcohol is selected from linear or branched saturated C6-C aliphatic alcohols. 30 Among fatty alcohols, linear or branched saturated C 12 ~C20 Fatty alcohols may be preferably used. Any linear or branched saturated C 16 ~C 20 Fatty alcohols are more preferably used. 16 ~C 20 Aliphatic alcohols are even more preferably used.

[0083] Examples of saturated fatty alcohols include lauryl alcohol, cetyl alcohol, stearyl alcohol, isostearyl alcohol, behenyl alcohol, undecylenyl alcohol, myristyl alcohol, octyldodecanol, hexyldecanol, and mixtures thereof. In one embodiment, cetyl alcohol, stearyl alcohol, octyldodecanol, hexyldecanol, or mixtures thereof (e.g., cetearyl alcohol), and behenyl alcohol can be used as saturated fatty alcohols.

[0084] According to at least one embodiment, the fatty alcohols used in the compositions according to the invention are preferably chosen from cetyl alcohol, octyldodecanol, hexyldecanol and mixtures thereof.

[0085] It is also preferred that the (a) oil is selected from oils having a molecular weight of less than 600 g / mol.

[0086] Preferably, the (a) oil has a low molecular weight, such as less than 600 g / mol, and contains one or more short hydrocarbon chains (C1 to C 12 ester oils having methyl sarcosine, isopropyl lauroyl sarcosine, isopropyl myristate, isopropyl palmitate, isononyl isononanoate, and ethylhexyl palmitate, silicone oils (volatile silicones such as cyclohexasiloxane), hydrocarbon oils (e.g., isododecane, isohexadecane, and squalane), branched and / or unsaturated fatty alcohols (C 12 ~C 30) type oils, such as octyldodecanol and oleyl alcohol, and ether oils, such as dicaprylyl ether.

[0087] Preferred embodiments of (a) oil are described below.

[0088] The (a) oil is preferably selected from the group consisting of (i) fatty alcohols, (ii) fatty acids, (iii) monocarboxylic acid monoesters, (iv) dicarboxylic acid diesters, (v) N-acylamino acid esters, and (vi) alkyl lactates, under the following conditions: - (i) the fatty alcohol and (ii) the fatty acid each contain a branched alkyl group or a linear or branched alkenyl group having from 4 to 30, preferably from 5 to 26, more preferably from 6 to 22 carbon atoms; - (iii) the monocarboxylic acid monoesters each contain a branched alkyl group or a linear or branched alkenyl group having 4 to 30, preferably 5 to 26, more preferably 6 to 22 carbon atoms, - (iv) the divalent carboxylic acid diester comprises at least one, preferably two, branched alkyl groups having 3 to 10, preferably 3 to 8, more preferably 3 to 6 carbon atoms, and an alkylene group having 6 to 18, preferably 6 to 14, more preferably 6 to 10 carbon atoms, (v) N-acylamino acid esters contain a branched alkyl group having 3 to 10, preferably 3 to 8, more preferably 3 to 6 carbon atoms, and a linear or branched acyl group having 4 to 30, preferably 5 to 26, more preferably 6 to 22 carbon atoms, - (vi) The alkyl lactate comprises a linear or branched alkyl group or a linear or branched alkenyl group, each having 4 to 30, preferably 5 to 26, more preferably 6 to 22 carbon atoms.

[0089] As used herein, the term "alkyl group" refers to a linear or branched monovalent saturated aliphatic hydrocarbon group.

[0090] Examples of the linear alkyl group having 4 to 30 carbon atoms include an n-butyl group, an n-pentyl group, an n-hexyl group, an n-heptyl group, an n-octyl group, an n-nonyl group, an n-decyl group, an n-undecyl group, an n-dodecyl group, an n-tridecyl group, an n-tetradecyl group, an n-pentadecyl group, an n-hexadecyl group, an n-heptadecyl group, an n-octadecyl group, an n-nonadecyl group, and an n-eicosyl group.

[0091] Examples of branched alkyl groups having 4 to 30 carbon atoms include isobutyl, sec-butyl, tert-butyl, isopentyl, neopentyl, isohexyl, neohexyl, isoheptyl, neoheptyl, isooctyl, isononyl, isodecyl, isoundecyl, isododecyl, isotridecyl, isotetradecyl, isopentadecyl, isohexadecyl, isoheptadecyl, isooctadecyl, isononadecyl, and isoeicosyl groups.

[0092] Examples of branched alkyl groups having 3 to 10 carbon atoms include an isopropyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, an isopentyl group, a neopentyl group, an isohexyl group, a neohexyl group, an isoheptyl group, a neoheptyl group, an isooctyl group, an isononyl group, and an isodecyl group.

[0093] As used herein, the term "alkenyl group" refers to a straight-chain or branched, monovalent unsaturated aliphatic hydrocarbon group having at least one carbon-carbon double bond.

[0094] Examples of the linear alkenyl group having 4 to 30 carbon atoms include a butenyl group, a pentenyl group, a hexenyl group, a heptenyl group, a heptadienyl group, a heptatrienyl group, an octenyl group, an octadienyl group, an octatrienyl group, a nonenyl group, a nonadienyl group, a nonatrienyl group, a decenyl group, a decadienyl group, a decatrienyl group, an undecenyl group, an undecadienyl group, an undecatrienyl group, a dodecenyl group, a dodecadienyl group, a dodecatrienyl group, a tridecenyl group, a tridecadienyl group, and a tridecyl group. Examples of such an alkyl group include a trienyl group, a tetradecenyl group, a tetradecadienyl group, a tetradecadienyl group, a tetradecatrienyl group, a pentadecenyl group, a pentadecadienyl group, a pentadecatrienyl group, a hexadecenyl group, a hexadecadienyl group, a hexadecatrienyl group, a heptadecenyl group, a heptadecadienyl group, a heptadecatrienyl group, an octadecenyl group, an octadecadienyl group, an octadecatrienyl group, a nonadecenyl group, a nonadecadienyl group, a nonadecatrienyl group, and an eicosenyl group.

[0095] Examples of the branched alkenyl group having 4 to 30 carbon atoms include an isobutenyl group, a sec-butenyl group, an isopentenyl group, an isohexenyl group, an isoheptenyl group, an isooctenyl group, an isononenyl group, an isodecenyl group, an isodecadienyl group, an isodecatrienyl group, an isoundecenyl group, an isoundecadienyl group, an isoundectrienyl group, an isododecenyl group, an isododecadienyl group, an isododecatrienyl group, an isotridecenyl group, an isotridecadienyl group, an isotridecatrienyl group, an isotetradec ... Examples of such groups include a cadienyl group, an isotetradecadienyl group, an isotetradecatrienyl group, an isopentadecenyl group, an isopentadecadienyl group, an isopentadecatrienyl group, an isohexadecenyl group, an isohexadecadienyl group, an isohexadecatrienyl group, an isoheptadecenyl group, an isoheptadecadienyl group, an isoheptadecatrienyl group, an isooctadecenyl group, an isooctadecadienyl group, an isooctadecatrienyl group, an isonadecenyl group, an isonadecadienyl group, an isonadecatrienyl group, and an isoeicosenyl group.

[0096] As used herein, the term "acyl group" refers to the group R-CO-, where R is a linear or branched monovalent saturated aliphatic hydrocarbon group (alkyl group).

[0097] Examples of the linear or branched acyl group having 4 to 30 carbon atoms include butanoyl, isobutanoyl, sec-butanoyl, tert-butanoyl, n-pentanoyl, isopentanoyl, neopentanoyl, n-hexanoyl, isohexanoyl, neohexanoyl, n-heptanoyl, isoheptanoyl, neoheptanoyl, n-octanoyl, isooctanoyl, n-nonanoyl, isononanoyl, n-decanoyl, isodecanoyl, n-undecanoyl, isoundecanoyl, and n-dodecayl. Examples of the alkyl group include a hydroxyl group (lauroyl group), an isododecanoyl group, an n-tridecanoyl group, an isotridodecanoyl group, an n-tetradecanoyl group (myristoyl group), an isotetradecanoyl group, an n-pentadecanoyl group, an isopentadecanoyl group, an n-hexadecanoyl group (palmitoyl group), an isohexadecanoyl group, an n-heptadecanoyl group, an isohexadecanoyl group, an n-octadecanoyl group (stearoyl group), an isooctadecanoyl group, an n-nonadecanoyl group, an isononadecanoyl group, an n-eicosanoyl group, and an isoeicosanoyl group.

[0098] (i) The aliphatic alcohol has the following general formula (1): R 1 -OH (1) (In the formula, R 1 each represents a branched alkyl group or a linear or branched alkenyl group having 4 to 30, preferably 5 to 26, more preferably 6 to 22 carbon atoms. It can be expressed as:

[0099] Examples of branched alkyl groups and straight or branched alkenyl groups, each having 4 to 30 carbon atoms, include those listed above.

[0100] Examples of the (i) aliphatic alcohol represented by formula (1) include 2-ethylhexanol, palmitoleyl alcohol, isostearyl alcohol, elaidyl alcohol, oleyl alcohol, linoleyl alcohol, ricinoleyl alcohol, erucyl alcohol, and mixtures thereof.

[0101] (i) The fatty alcohol is preferably selected from the group consisting of isostearyl alcohol, oleyl alcohol, and mixtures thereof.

[0102] (ii) The fatty acid has the following general formula (2): R 1 -COOH (2) (In the formula, R 1 each represents a branched alkyl group or a linear or branched alkenyl group having 4 to 30, preferably 5 to 26, more preferably 6 to 22 carbon atoms. It can be expressed as:

[0103] Examples of branched alkyl groups and straight or branched alkenyl groups, each having 4 to 30 carbon atoms, include those listed above.

[0104] Examples of the (ii) fatty acids represented by formula (2) include isocaproic acid, isononanoic acid, crotonic acid, isolauric acid, myristoleic acid, isopalmitic acid, palmitoleic acid, isostearic acid, elaidic acid, oleic acid, linoleic acid, linolenic acid, arachidonic acid, eicosapentaenoic acid, tetracosapentaenoic acid, docosahexaenoic acid, nervonic acid, and mixtures thereof.

[0105] (ii) The fatty acid is preferably selected from the group consisting of isostearic acid, oleic acid, and mixtures thereof.

[0106] (iii) The monocarboxylic acid monoester is represented by the following general formula (3): R 2-COO-R 3 (3) (In the formula, R 2 each represents a branched alkyl group or a linear or branched alkenyl group having 4 to 30, preferably 5 to 26, and more preferably 6 to 22 carbon atoms; R 3 represents a branched alkyl group having 3 to 10, preferably 3 to 8, more preferably 3 to 6 carbon atoms. It can be expressed as:

[0107] Examples of branched alkyl groups and straight or branched alkenyl groups, each having 4 to 30 carbon atoms, include those listed above.

[0108] Examples of branched alkyl groups having 3 to 10 carbon atoms include those listed above.

[0109] Examples of the (iii) monocarboxylic acid monoester represented by formula (3) include isopropyl palmitate, isopropyl myristate, isocetyl stearate, 2-ethylhexyl isononanoate, isononyl isononanoate, isodecyl neopentanoate, isostearyl neopentanoate, and mixtures thereof.

[0110] (iii) The monocarboxylic acid monoester is preferably isopropyl isostearate.

[0111] (iv) The dicarboxylic acid diester is represented by the following general formula (4): R 2 -OC(=O)-R 4 -C(=O)OR 3 (4) (In the formula, R 2 and R 3 independently represent a branched alkyl group having 3 to 10, preferably 3 to 8, more preferably 3 to 6 carbon atoms; R 4represents a linear or branched alkylene group having 6 to 18, preferably 6 to 14, more preferably 6 to 10 carbon atoms. It can be expressed as:

[0112] Examples of branched alkyl groups having 3 to 10 carbon atoms include those listed above.

[0113] Examples of the linear or branched alkylene group having 2 to 10 carbon atoms include an ethylene group, a propylene group, a butylene group, a pentylene group, a hexylene group, a heptylene group, an octylene group, a nonylene group, and a decanylene group.

[0114] (iv) The divalent carboxylic acid diester is preferably selected from the group consisting of diisopropyl adipate, diisopropyl sebacate, and mixtures thereof.

[0115] (v) N-acyl amino acid esters are represented by the following general formula (5): R 2 -N(R 5 )-CH(R 6 )-(CH2) n -COO-R 3 (5) (In the formula, R 2 represents a linear or branched acyl group having 4 to 30, preferably 5 to 26, and more preferably 6 to 22 carbon atoms; R 3 represents a branched alkyl group having 3 to 10, preferably 3 to 8, more preferably 3 to 6 carbon atoms; R 5 represents a hydrogen atom or a linear or branched alkyl group having 1 to 4 carbon atoms; R 6 represents a hydrogen atom or a linear or branched alkyl group having 1 to 4 carbon atoms which may be substituted by a hydroxy group or a phenyl group; n represents an integer from 0 to 2. It can be expressed as:

[0116] Examples of the straight-chain or branched acyl group having 4 to 30 carbon atoms include those listed above.

[0117] Examples of branched alkyl groups having 3 to 10 carbon atoms include those listed above.

[0118] Examples of linear or branched alkyl groups having 1 to 4 carbon atoms include methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, sec-butyl and tert-butyl groups.

[0119] Examples of the N-acyl amino acid ester (v) represented by formula (5) include N-capryloyl sarcosine isopropyl ester, N-caprinoyl sarcosine isopropyl ester, N-lauroyl sarcosine isopropyl ester, N-coconut oil fatty acid acyl sarcosine isopropyl ester (N-cocoyl sarcosine isopropyl ester), N-myristoyl sarcosine isopropyl ester, N-palmitoyl sarcosine isopropyl ester, N-stearoyl sarcosine isopropyl ester, N -Capryloyl sarcosine isobutyl ester, N-caprinoyl sarcosine isobutyl ester, N-lauroyl sarcosine isobutyl ester, N-coconut oil fatty acid acyl sarcosine isobutyl ester (N-cocoyl sarcosine isobutyl ester), N-myristoyl sarcosine isobutyl ester, N-palmitoyl sarcosine isobutyl ester, N-stearoyl sarcosine isobutyl ester, N-capryloyl glycine isopropyl ester, N-caprinoyl glycine isopropyl ester, N Examples of the isopropyl ester include N-lauroylglycine isopropyl ester, N-coconut oil fatty acid acylglycine isopropyl ester (N-cocoylglycine isopropyl ester), N-myristoylglycine isopropyl ester, N-palmitoylglycine isopropyl ester, N-stearoylglycine isopropyl ester, N-capryloylalanine isopropyl ester, N-caprinoylalanine isopropyl ester, N-lauroylalanine isopropyl ester, N-coconut oil fatty acid acylalanine isopropyl ester (N-cocoylalanine isopropyl ester), N-myristoylalanine isopropyl ester, N-palmitoylalanine isopropyl ester, N-stearoylalanine isopropyl ester, N-lauroyl-β-alanine isopropyl ester, N-lauroyl-N-methyl-β-alanine isopropyl ester, and N-coconut oil fatty acid acyl-N-methyl-β-alanine isopropyl ester (N-cocoyl-N-methyl-β-alanine isopropyl ester).

[0120] (v) The N-acyl amino acid ester is preferably lauroyl sarcosine isopropyl. As lauroyl sarcosine isopropyl, commercially available products such as Eldew (registered trademark) S1-205 by Ajinomoto Co., Inc. can be used.

[0121] (vi) Alkyl lactate is represented by the following general formula (6): CH3-C(OH)-COO-R 7 (6) (In the formula, R 7 each represents a linear or branched alkyl group or a linear or branched alkenyl group having 4 to 30, preferably 5 to 26, and more preferably 6 to 22 carbon atoms. It can be expressed as:

[0122] Examples of the linear or branched alkyl group or linear or branched alkenyl group, each having 4 to 30 carbon atoms, include those listed above.

[0123] Examples of (vi) alkyl lactates represented by formula (6) include capryl lactate, caprylyl lactate, lauryl lactate, myristyl lactate, palmityl lactate, stearyl lactate, isostearyl lactate, oleyl lactate, and linoleyl lactate.

[0124] (vi) The alkyl lactate is preferably selected from the group consisting of lauryl lactate, isostearyl lactate, and mixtures thereof.

[0125] The amount of (a) oil in the composition according to the present invention may be 0.5% by weight or more, preferably 1% by weight or more, more preferably 2% by weight or more, relative to the total weight of the composition.

[0126] On the other hand, the amount of (a) oil in the composition according to the present invention may be 25% by weight or less, preferably 20% by weight or less, more preferably 15% by weight or less, relative to the total weight of the composition.

[0127] Therefore, the amount of (a) oil in the composition according to the present invention can be 0.5% to 25% by mass, preferably 1% to 20% by mass, more preferably 2% to 15% by mass, relative to the total mass of the composition.

[0128] [Diol] The composition according to the present invention comprises at least one (b) diol having at least one fatty chain containing three or more carbon atoms. Two or more (b) diols having at least one carbon chain containing three or more carbon atoms may be used.

[0129] The term "diol" as used herein refers to a compound having two alcohol functional groups. In other words, a diol is an alcohol having two hydroxy groups.

[0130] The number of carbon atoms in the carbon chain may be up to 10, preferably up to 8, more preferably up to 6. It may even be more preferred for the number of carbon atoms in the carbon chain to be 5 or 6.

[0131] The carbon chain containing three or more carbon atoms in component (b) may be linear or branched. The carbon chain must not be interrupted by heteroatoms, such as oxygen, sulfur, and nitrogen atoms. Thus, the carbon chain may contain consecutive carbon atoms.

[0132] The number of carbon chains containing three or more carbon atoms in component (b) may preferably be one or two.

[0133] The total number of carbon atoms in component (b) may be 5 or more. The total number of carbon atoms in component (b) may be 10 or less, preferably 8 or less, and more preferably 6 or less. It may even be more preferred that the total number of carbon atoms in component (b) is 5 or 6.

[0134] (b) The diol having at least one carbon chain containing 3 or more carbon atoms (preferably 8 or less, more preferably 6 or less) may have a divalent linear or branched hydrocarbon group. The divalent linear or branched hydrocarbon group that may be present in component (b) may be saturated or unsaturated. (b) The diol having at least one carbon chain containing 3 or more carbon atoms preferably contains a divalent linear or branched saturated hydrocarbon group, more preferably a linear or branched alkylene group, such as a propylene group, a butylene group, a pentylene group, or a hexylene group.

[0135] (b) The diol having at least one carbon chain containing three or more carbon atoms may have a linear, branched, or cyclic molecular structure, so long as it has a carbon chain containing three or more carbon atoms.

[0136] (b) a diol having at least one carbon chain containing three or more carbon atoms, containing two hydroxy groups, 3~10 Diols, preferably C 4~8 Diols, more preferably C 5~6 It may also be a diol.

[0137] (b) The diol having at least one carbon chain containing three or more carbon atoms is preferably selected from the group consisting of propylene glycol, dipropylene glycol, polypropylene glycol, butylene glycol, dibutylene glycol, polybutylene glycol, pentylene glycol, dipentylene glycol, hexylene glycol, dihexylene glycol, and mixtures thereof.

[0138] (b) More preferably, the diol having at least one carbon chain containing three or more carbon atoms is selected from the group consisting of propylene glycol, dipropylene glycol, butylene glycol, pentylene glycol, hexylene glycol, and mixtures thereof, with pentylene glycol being most preferred.

[0139] The amount of (b) diol having at least one carbon chain containing 3 or more carbon atoms in the composition according to the present invention may be 20% by weight or more, preferably 25% by weight or more, more preferably 30% by weight or more, relative to the total weight of the composition.

[0140] On the other hand, the amount of (b) diol having at least one carbon chain containing 3 or more carbon atoms in the composition according to the present invention may be 60% by mass or less, preferably 55% by mass or less, more preferably 50% by mass or less, based on the total mass of the composition.

[0141] Therefore, the amount of (b) diol having at least one carbon chain containing three or more carbon atoms in the composition according to the present invention can be 20% by mass to 60% by mass, preferably 25% by mass to 55% by mass, and more preferably 30% by mass to 50% by mass, relative to the total mass of the composition.

[0142] [Diol / oil mass ratio] The mass ratio of the amount of (b) diol having at least one carbon chain containing 3 or more carbon atoms to the amount of (a) oil can be 4 or more, preferably 5 or more, and more preferably 6 or more.

[0143] On the other hand, the mass ratio of the amount of (b) diol having at least one carbon chain containing 3 or more carbon atoms to the amount of (a) oil may be 20 or less, preferably 15 or less, and more preferably 10 or less.

[0144] Therefore, the mass ratio of the amount of (b) diol having at least one carbon chain containing 3 or more carbon atoms to the amount of (a) oil can be 4 to 20, preferably 5 to 15, and more preferably 6 to 10.

[0145] [Skin care active agent] The composition according to the present invention comprises at least one skin care active ingredient (c). A single type of skin care active ingredient (c) may be used, or two or more different types of skin care active ingredients (c) may be used in combination.

[0146] (c) It is preferred that the skin care active ingredient has a log P value of 4 or less, more preferably within the range of -4.5 to 4.0, and even more preferably -4.0 to 3.5.

[0147] The log P value is the base 10 logarithm of the apparent octanol / water partition coefficient. Log P values ​​are known and are determined by standard tests to determine the concentration of compound (c) in octanol and water. Log P can be calculated by the method described by Meylan and Howard in "Atom / Fragment contribution method for estimating octanol-water partition coefficients," J. Pharm. Sci., 84:83-92, 1995. This value may also be calculated using a number of commercially available software packages that determine log P as a function of the structure of the molecule. For example, Epiwin software from the U.S. Environmental Protection Agency can be mentioned.

[0148] This value can be calculated using, inter alia, ACD (Advanced Chemistry Development) Solaris software V4.67, and can also be obtained from Exploring QSAR: hydrophobic, electronic and steric constants (ACS professional reference book, 1995). There is also an internet site that provides approximate values ​​(address: http: / / esc.syrres.com / interkow / kowdemo.htm).

[0149] (c) The skin care active ingredient may be in the form of a salt. Salts of (c) the skin care active ingredient include conventional, non-toxic salts of such compounds, for example, formed from acids or bases.

[0150] (c) The skin care active ingredient is preferably a skin care cosmetic active ingredient, more preferably a skin whitening ingredient or a skin anti-aging ingredient, such as an anti-wrinkle ingredient.

[0151] (c) Skin care active ingredients include vitamin B3 and derivatives.

[0152] Vitamin B3, also known as vitamin PP, has the following formula (I):

[0153] [ka]

[0154] where R can be -CONH (niacinamide), -COOH (nicotinic acid or niacin), or CHOH (nicotinyl alcohol), -CO-NH-CH-COOH (nicotinuric acid), or -CO-NH-OH (nicotinyl hydroxamic acid). Niacinamide is preferred.

[0155] Vitamin B3 derivatives that may be mentioned include, for example, nicotinic acid esters such as tocopherol nicotinate, amides derived from niacinamide by substitution of the hydrogen group of -CONH, products from the reaction of carboxylic acids with amino acids, esters of nicotinyl alcohol with carboxylic acids, such as acetic acid, salicylic acid, glycolid acid or palmitic acid.

[0156] Mention may also be made of derivatives of the following: 2-chloronicotinamide, 6-methylnicotinamide, 6-aminonicotinamide, N-methylnicotinamide, N,N-dimethylnicotinamide, N-(hydroxymethyl)nicotinamide, quinolinic acid imide, nicotinanilide, N-benzylnicotinamide, N-ethylnicotinamide, nifenazone, nicotinaldehyde, isonicotinic acid, methylisonicotinic acid, thionicotinamide, nialamide, 2-mercaptonicotinic acid, nicomol and niaprazine, methyl nicotinate and sodium nicotinate.

[0157] Other vitamin B3 derivatives that may also be mentioned include its inorganic salts, such as the chlorides, bromides, iodides or carbonates, and its organic salts, such as those obtained by reaction with carboxylic acids, for example acetates, salicylates, glycolates, lactates, malates, citrates, mandelates, tartrates, etc.

[0158] (c) Skin care active ingredients include ascorbic acid and its derivatives.

[0159] Ascorbic acid is generally in the L form, as it is usually extracted from natural products.

[0160] Due to its chemical structure (α-keto lactone), which makes it highly sensitive to certain environmental parameters, such as light, heat and aqueous media, it may be advantageous to use ascorbic acid in the form of a derivative or analogue selected, for example, from sugar esters of ascorbic acid, or metal salts, alkali metal salts, esters and sugars of phosphoryl ascorbic acid.

[0161] Sugar esters of ascorbic acid that can be used in the present invention are, inter alia, glycosyl, mannosyl, fructosyl, fucosyl, galactosyl, N-acetylglucosamine and N-acetylmuramin derivatives of ascorbic acid, as well as mixtures thereof, more particularly ascorbyl glucosides, such as ascorbyl-2-glucoside, 2-O-α-D-glucopyranosyl L-ascorbic acid, or 6-O-β-D-galactopyranosyl L-ascorbic acid. The latter compounds and methods for their preparation are described, inter alia, in documents EP-A-0 487 404, EP-A-0 425 066, and JP-A-05-213 736.

[0162] As regards the metal salts of phosphoryl ascorbic acid, they can be chosen from alkali metal ascorbyl phosphates, especially sodium ascorbyl phosphate, alkaline earth metal ascorbyl phosphates and transition metal ascorbyl phosphates.

[0163] Ascorbic acid precursors can also be used, such as activator amides and activator sugar derivatives, which require proteases or peptidases and glycosidases, respectively, as enzymes to release ascorbic acid in situ. Such compounds are described in patent EP 0 667 145.

[0164] The active agent sugar derivative is especially selected from C3-C6 sugar derivatives, especially glucosyl, mannosyl, fructosyl, fucosyl, N-acetylglucosamine, galactosyl, and N-acetylgalactosamine derivatives, N-acetylmuramic acid derivatives, and sialic acid derivatives, and mixtures thereof.

[0165] The second ascorbic acid precursor may be selected from derivatives that are hydrolyzed by other enzymes, such as esterases, phosphatases, sulfatases, etc. According to the present invention, the second active agent precursor may be selected from, for example, phosphate esters, sulfate esters, palmitate esters, acetate esters, propionate esters, ferulate esters, and generally alkyl or acyl esters of the active agent; acyl or alkyl ethers. The acyl and alkyl groups contain, in particular, 1 to 30 carbon atoms. The skin care active ingredient may include 3-O-ethyl ascorbic acid.

[0166] In particular, the second precursor may be an ester derived from reaction with a mineral acid, such as a sulfate or phosphate ester, which reacts with sulfatases or phosphatases on contact with the skin, or the second precursor may be an acyl or alkyl ester derived from reaction with an organic acid, such as palmitic acid, acetic acid, propionic acid, nicotinic acid, 1,2,3-propanetricarboxylic acid, or ferulic acid, which reacts with specific skin esterases.

[0167] Other derivatives are described, for example, in patent EP 1 430 883.

[0168] Ascorbic acid analogues are more particularly salts thereof, especially alkali metal salts such as sodium ascorbate, esters thereof, especially acetate, propionate or palmitate esters, or sugars thereof, especially glycosyl ascorbic acids.

[0169] (c) Examples of skin care active ingredients include resorcinol derivatives.

[0170] The resorcinol derivative may be preferably a derivative substituted at the 4-position, such as a 4-alkylresorcinol, more preferably phenylethyl resorcinol, 4-n-butylresorcinol, and 4-(tetrahydro-2H-pyran-4-yl)benzene-1,3-diol, and particularly phenylethyl resorcinol due to its whitening effect. Phenylethyl resorcinol, also known as 4-(1-phenylethyl)-1,3-benzenediol, is represented by the following chemical formula: Phenylethyl resorcinol is available, for example, from Symrise Corp. (Product name: Symwhite 377®).

[0171] [ka]

[0172] Other examples of resorcinol derivatives include 2-methylresorcinol, 5-methylresorcinol, 4-methylresorcinol, 4-ethylresorcinol, 2,5-dimethylresorcinol, 4,5-dimethylresorcinol, 2,4-dimethyl-1,3-benzenediol, 3,5-dihydroxybenzylamine, 5-methoxyresorcinol, 3,5-dihydroxybenzyl alcohol, 2-methoxyresorcinol, 4-methoxyresorcinol, 3,5-dihydroxytoluene monohydrate, 4-chlororesorcinol, 2-chlororesorcinol, 2',4'-dihydro Dihydroxyacetophenone, 3',5'-dihydroxyacetophenone, 2,6-dihydroxy-4-methylbenzaldehyde, 4-propylresorcinol, 2,4-dihydroxy-1,3,5-trimethylbenzene, 3,5-dihydroxybenzamide, 2,6-dihydroxybenzamide, 2,4-dihydroxybenzamide, 2,4-dihydroxybenzoic acid, 2,6-dihydroxybenzoic acid, 3,5-dihydroxybenzoic acid, 2,6-dihydroxy-4-methylbenzyl alcohol, 3,5-dihydroxyanisole hydrate, 4-amino Resorcinol hydrochloride, 2-aminoresorcinol hydrochloride, 5-aminobenzene-1,3-diol hydrochloride, 2',4'-dihydroxypropiophenone, 2',4'-dihydroxy-3'-methylacetophenone, (2,4-dihydroxyphenyl)acetone, (3,5-dihydroxyphenyl)acetone, 2,6-dihydroxy-4'-methylacetophenone, 4-n-butylresorcinol, 2,4-diethyl-1,3-benzenediol, 3,5-dihydroxy-4-methylbenzoic acid, 2,6-dihydroxy-4-methylbenzoic acid Fragrance, 2,4-dihydroxy-6-methylbenzoic acid, 3,5-dihydroxyphenylacetic acid, 2-ethyl-5-methoxybenzene-1,3-diol, 4-amino-3,5-dihydroxybenzoic acid, 3,5-dihydroxyacetophenone monohydrate, 3,5-dihydroxybenzylamine hydrochloride, 4,6-dichlororesorcinol, 2',4'-dihydroxy-3'-methylpropiophenone, 1-(3-ethyl-2,6-dihydroxyphenyl)ethan-1-one, 2',6'-dihydroxy-4'-methoxyacetophenone, 1-(2,6-dihydroxy-3-methoxyphenyl)ethan-1-one, 3(2,4-dihydroxyphenylpropionic acid, and 2,4-dihydroxy-3,6-dimethylbenzoic acid.

[0173] (c) Skin care active ingredients include C-glycoside derivatives.

[0174] The C-glycoside derivatives that may be present in the composition according to the invention have the general formula (II) below:

[0175] [ka]

[0176] (In the formula, R represents an unsubstituted linear C1-C4, especially C1-C2 alkyl group, in particular methyl; S represents a monosaccharide selected from D-glucose, D-xylose, N-acetyl-D-glucosamine and L-fucose, in particular D-xylose; X represents a group selected from -CO-, -CH(OH)- and -CH(NH2)-, preferentially a -CH(OH)- group. The compound and also cosmetically acceptable salts thereof, solvates thereof, such as hydrates, and optical isomers thereof.

[0177] Non-limiting examples of C-glycoside derivatives that are particularly more suitable for use in the present invention include, inter alia, the following derivatives: C-beta-D-xylopyranoside-n-propan-2-one, C-alpha-D-xylopyranoside-n-propan-2-one, C-beta-D-xylopyranoside-2-hydroxypropane, C-alpha-D-xylopyranoside-2-hydroxypropane, 1-(C-beta-D-glucopyranosyl)-2-hydroxypropane, 1-(C-alpha-D-glucopyranosyl)-2-hydroxypropane, 1-(C-beta-D-glucopyranosyl)-2-aminopropane, 1-(C-alpha-D-glucopyranosyl)-2-aminopropane, 3'-(acetamido-C-beta-D-glucopyranosyl)propan-2'-one, 3'-(acetamido-C-alpha-D-glucopyranosyl)propan-2'-one, 1-(acetamido-C-beta-D-glucopyranosyl)-2-hydroxypropane, 1-(acetamido-C-beta-D-glucopyranosyl)-2-aminopropane, and also cosmetically acceptable salts thereof, solvates thereof, such as hydrates, and optical isomers thereof.

[0178] According to a particular embodiment, C-beta-D-xylopyranoside-2-hydroxypropane or C-alpha-D-xylopyranoside-2-hydroxypropane, and even better C-beta-D-xylopyranoside-2-hydroxypropane, may advantageously be used for the preparation of the composition according to the invention.

[0179] According to a particular embodiment, the C-glycoside derivative suitable for use in the present invention may advantageously be hydroxypropyltetrahydropyrantriol, also known as C-beta-D-xylopyranoside-2-hydroxypropane, sold in particular under the name Mexoryl SBB® by the company Chimex as a 30% by weight solution in a water / propylene glycol mixture (60 / 40). According to one embodiment, the C-glycoside derivative is in the form of a solution in which it is present in an amount of 30% by weight relative to the total weight of the solution, the remainder being a mixture of water and propylene glycol.

[0180] Salts of C-glycoside derivatives suitable for use in the present invention may include conventional physiologically acceptable salts of these compounds, such as salts formed with organic or mineral acids. Examples that may be mentioned include salts with mineral acids such as sulfuric acid, hydrochloric acid, hydrobromic acid, hydroiodic acid, phosphoric acid, and boric acid. Salts of organic acids may also be mentioned, which may contain one or more carboxylic, sulfonic, or phosphonic acid groups. These may be linear, branched, or cyclic aliphatic acids, or aromatic acids. These acids may also contain one or more heteroatoms selected from O and N, for example, in the form of hydroxyl groups. Among these, propionic acid, acetic acid, terephthalic acid, citric acid, and tartaric acid may be mentioned.

[0181] Acceptable solvates of the compounds mentioned above include conventional solvates, for example those formed during the final steps of the preparation of said compounds due to the presence of a solvent. Examples that may be mentioned include solvates resulting from the presence of water or linear or branched alcohols, such as ethanol or isopropanol.

[0182] C-glycoside derivatives suitable for use in the present invention can be obtained inter alia by the synthesis methods described in document WO 02 / 051 828, the contents of which are incorporated herein by reference.

[0183] (c) Skin care active ingredients include salicylic acid and its derivatives. Derivatives of salicylic acid are represented by the formula (III):

[0184] [ka]

[0185] (In the formula, the R group represents a linear, branched, or cyclic saturated aliphatic chain containing 2 to 22 carbon atoms; an unsaturated chain containing 2 to 22 carbon atoms containing one or more double bonds, which may be conjugated; an aromatic nucleus linked directly or via a saturated or unsaturated aliphatic chain containing 2 to 7 carbon atoms to a carbonyl group, said groups being optionally substituted with one or more substituents, which may be the same or different, selected from: (a) a halogen atom; (b) a trifluoromethyl group; (c) a hydroxyl group in free form or esterified with an acid containing 1 to 6 carbon atoms; or (d) a carboxyl function in free form or esterified with a lower alcohol containing 1 to 6 carbon atoms; where R' is a hydroxyl group. The salicylic acid derivatives may be in the form of salts derived from inorganic or organic bases.

[0186] (c) Skin care active ingredients can include tranexamic acid and its derivatives, such as esters and amides of tranexamic acid.

[0187] Examples of tranexamic acid derivatives include tranexamic acid dimers (e.g., trans-4-(trans-aminomethylcyclohexanecarbonyl)aminomethylcyclohexanecarboxylic acid hydrochloride), esters of tranexamic acid and hydroquinone (e.g., 4'-hydroxyphenyl trans-4-aminomethylcyclohexanecarboxylate), esters of tranexamic acid and gentisic acid (e.g., 2-(trans-4-aminomethylcyclohexanecarbonyloxy)-5-hydroxybenzoic acid and salts thereof), and tranexamic acid amides (e.g., trans-4-aminomethylcyclohexanecarboxylic acid methylamide and salts thereof, trans-4-(p-methoxybenzoyl)aminomethylcyclohexanecarboxylic acid and salts thereof, and trans-4-guanidinomethylcyclohexanecarboxylic acid and salts thereof).

[0188] Even more preferably, the (c) skin care active ingredient is selected from the group consisting of ascorbyl glucoside, 3-O-ethyl ascorbic acid, tranexamic acid, hydroxypropyl tetrahydropyrantriol, niacinamide, salicylic acid, phenylethyl resorcinol, and mixtures thereof.

[0189] The amount of (c) skin care active ingredient in the composition according to the present invention may be 0.01% by weight or more, preferably 0.05% by weight or more, more preferably 0.1% by weight or more, relative to the total weight of the composition.

[0190] On the other hand, the amount of (c) skin care active ingredient in the composition according to the present invention may be 25% by weight or less, preferably 20% by weight or less, more preferably 15% by weight or less, based on the total weight of the composition.

[0191] Therefore, the amount of (c) skin care active ingredient in the composition according to the present invention may be in the range of 0.01% to 25% by weight, preferably 0.05% to 20% by weight, more preferably 0.1% to 15% by weight, relative to the total weight of the composition.

[0192] [water] The composition according to the present invention comprises (d) water.

[0193] The amount of (d) water in the composition according to the present invention may be 30% by mass or more, preferably 35% by mass or more, more preferably 40% by mass or more, based on the total mass of the composition.

[0194] On the other hand, the amount of (d) water in the composition according to the present invention may be 60% by mass or less, preferably 55% by mass or less, and more preferably 50% by mass or less, based on the total mass of the composition.

[0195] The amount of (d) water in the composition according to the present invention can be within the range of 30% by mass to 60% by mass, preferably 35% by mass to 55% by mass, and more preferably 40% by mass to 50% by mass, relative to the total mass of the composition.

[0196] [Cellulose compounds] The composition according to the present invention may contain (e) at least one cellulose compound. Two or more (e) cellulose compounds may be used.

[0197] (e) The at least one cellulose compound can function as a skin lightening enhancer.

[0198] (e) The cellulose compounds can be anionic, cationic, amphoteric or nonionic polymers.

[0199] The term "cellulose" compound means, according to the present invention, any polysaccharide compound having in its structure a sequence of glucose residues linked together via β-1,4 bonds, and includes unsubstituted cellulose as well as anionic, cationic, amphoteric and nonionic cellulose derivatives.

[0200] Therefore, (e) the cellulose compound can be selected from, for example, unsubstituted cellulose, including microcrystalline cellulose, and cellulose ethers, cellulose esters, cellulose ester ethers, and mixtures thereof. Among cellulose esters, inorganic esters of cellulose (such as cellulose nitrate, sulfate, and phosphate esters), organic cellulose esters (such as cellulose monoacetate, triacetate, amidopropionate, acetate butyrate, acetate propionate, and acetate trimellitate), and mixed organic / inorganic esters of cellulose, such as cellulose acetate butyrate sulfate and cellulose acetate propionate sulfate. Among cellulose ester ethers, hydroxypropylmethylcellulose phthalate and ethylcellulose sulfate can be mentioned.

[0201] According to a particular embodiment of the present invention, the (e) cellulose compound is non-associative. A "non-associative" cellulose compound is one that does not contain any fatty chains in its structure, preferably no C 10 ~C 30 It is a chain-free cellulose polymer.

[0202] According to a first variant, the cellulose compound (e) is nonionic. Examples include (C1-C4) alkylcelluloses such as methylcellulose and ethylcellulose, for example Ethocel Standard 100 Premium from Dow Chemical; (poly)hydroxy(C1-C4) alkylcelluloses such as hydroxymethylcellulose, hydroxyethylcellulose, for example Natrosol 250 HHR from Aqualon, and hydroxypropylcellulose, for example Klucel EF from Aqualon; mixed (poly)hydroxy(C1-C4) alkyl-(C1-C4) alkylcelluloses such as hydroxypropylmethylcellulose, for example Methocel E4M from Dow Chemical; hydroxyethylmethylcellulose, hydroxyethylethylcellulose, for example Bermocoll E 481 FQ from Akzo Noble, and hydroxybutylmethylcellulose.

[0203] According to a second variant, the cellulose compound (e) is anionic. Among the anionic cellulose ethers, mention may be made of (poly)carboxy(C1-C4) alkylcelluloses and their salts. Examples that may be mentioned include carboxymethylcellulose, carboxymethylmethylcellulose, such as Blanose 7M from Aqualon, and carboxymethylhydroxyethylcellulose, as well as their sodium salts.

[0204] According to a third variant, the cellulose compound (e) is cationic. Among the cationic celluloses, mention may be made of cationic cellulose derivatives, such as cellulose copolymers or derivatives grafted with water-soluble quaternary ammonium monomers, as described in particular in U.S. Pat. No. 4,131,576, such as (poly)hydroxy(C1-C4) alkylcelluloses, such as hydroxymethyl, hydroxyethyl or hydroxypropyl celluloses, in particular grafted with methacryloylethyltrimethylammonium, methacrylamidepropyltrimethylammonium or dimethyldiallylammonium salts. Commercially available products corresponding to this definition are, more particularly, the products sold by National Starch under the names Celquat® L 200 and Celquat® H 100.

[0205] According to another detailed embodiment of the present invention, the (e) cellulose compound is associative. An "associative" cellulose compound is a cellulose compound that contains any fatty chain in its structure, preferably C 10 ~C 30 It is a cellulose polymer containing chains.

[0206] The associative cellulose compound may be cationic. Among these cationic associative cellulose compounds, preferred are quaternized (poly)hydroxyethylcelluloses modified with at least one fatty chain-containing group, such as an alkyl, arylalkyl, or alkylaryl group containing at least 8 carbon atoms, or mixtures thereof. The alkyl group of the quaternized cellulose or hydroxyethylcellulose preferably contains 8 to 30 carbon atoms. The aryl group preferably represents a phenyl, benzyl, naphthyl, or anthryl group. C8 to C 30 Examples of quaternized alkylhydroxyethylcelluloses having a fatty chain include the products Quatrisoft LM 200a, Quatrisoft LM-X 529-18-Aa, and Quatrisoft LM-X 529-18-Ba (C12 alkyl) and Quatrisoft LM-X 529-8a(C 18 alkyl), Crodacel QMa and Crodacel QLa (C 12 alkyl) and Crodacel QSa (C 18 alkyl), as well as the product Softcat SL 100a sold by the company Aqualon.

[0207] The associative cellulose compound may be non-ionic. Among these non-ionic associative cellulose compounds, preferred are those containing at least one fatty chain, such as an alkyl, arylalkyl or alkylaryl group, or a mixture thereof, where the alkyl group is C8 to C6. 30 cellulose or its derivatives modified with alkyl groups, in particular nonionic alkylhydroxyethylcelluloses, such as the products Natrosol Plus Grade 330 CS and Polysurf 67 (C 16 alkyl); nonionic nonoxynyl hydroxyethyl cellulose, such as the product Amercell HM-1500 sold by the company Amerchol; nonionic alkyl cellulose, such as the product Bermocoll EHM 100 sold by Berol Nobel.

[0208] The (e) cellulose compound may preferably be nonionic or anionic, and may be free of fatty chains (non-associative, nonionic or anionic alkyl cellulose polymers). Preferably, the (e) cellulose compound useful in the present invention is selected from nonionic cellulose ethers, such as (C1-C4) alkyl celluloses, (poly)hydroxy(C1-C4) alkyl celluloses, (poly)hydroxy(C1-C4) alkyl-(C1-C4) alkyl celluloses, such as hydroxypropyl methylcellulose, hydroxyethyl methylcellulose, hydroxyethyl ethyl cellulose, hydroxybutyl methylcellulose, hydroxymethyl cellulose, hydroxyethyl cellulose and hydroxypropyl cellulose, and anionic cellulose ethers, such as carboxymethylcellulose, in particular sodium carboxymethylcellulose.

[0209] (e) The cellulose compound is preferably selected from the group consisting of unmodified cellulose and nonionic or anionic cellulose ethers.

[0210] (e) More preferably, the cellulose compound is selected from the group consisting of cellulose, cellulose gum, hydroxymethyl cellulose, hydroxyethyl cellulose, hydroxypropyl methyl cellulose, sodium carboxymethyl cellulose, and mixtures thereof.

[0211] The amount of (e) the cellulose compound in the composition according to the present invention may be 0.01% by mass or more, preferably 0.05% by mass or more, more preferably 0.1% by mass or more, relative to the total mass of the composition.

[0212] On the other hand, the amount of (e) the cellulose compound in the composition according to the present invention may be 40% by mass or less, preferably 35% by mass or less, more preferably 30% by mass or less, based on the total mass of the composition.

[0213] Therefore, the amount of (e) the cellulose compound in the composition according to the present invention can be 0.01% by mass to 40% by mass, preferably 0.05% by mass to 35% by mass, and more preferably 0.01% by mass to 30% by mass, relative to the total mass of the composition.

[0214] [Optional ingredients] The composition according to the invention may further comprise at least one optional ingredient commonly used in the field of cosmetics, for example chosen from film-forming polymers, solvents, dyes, pigments, UV filters, antioxidants, preservatives, pH adjusters and mixtures thereof.

[0215] The compositions according to the invention may contain one or several cosmetically acceptable organic solvents, which may be alcohols, in particular monohydric alcohols such as ethyl alcohol, isopropyl alcohol, benzyl alcohol and phenylethyl alcohol; diols other than component (b), such as ethylene glycol; other polyols, such as glycerol, sugars and sugar alcohols; and ethers, such as ethylene glycol monomethyl, monoethyl and monobutyl ether, propylene glycol monomethyl, monoethyl and monobutyl ether, and butylene glycol monomethyl, monoethyl and monobutyl ether.

[0216] The amount of organic solvent in the composition according to the invention may be 0.01% by weight or more, preferably 0.1% by weight or more, more preferably 1% by weight or more, relative to the total weight of the composition.

[0217] On the other hand, the amount of organic solvent in the composition according to the invention may be 30% by weight or less, preferably 20% by weight or less, more preferably 10% by weight or less, relative to the total weight of the composition.

[0218] Therefore, the amount of organic solvent in the composition according to the present invention can be in the range of 0.01% by mass to 30% by mass, preferably 0.1% by mass to 20% by mass, and more preferably 1% by mass to 10% by mass, relative to the total mass of the composition.

[0219] (preparation) The composition according to the present invention can be prepared by mixing the essential ingredients described above and, if necessary, the optional ingredients described above.

[0220] The method and means for mixing the above essential components and optional components are not limited. Any conventional method and means can be used to mix the above essential components and optional components to prepare the composition according to the present invention.

[0221] [form] The form of the composition according to the present invention is not limited.

[0222] Compositions according to the present invention can be thermodynamically stable and may be considered as single-phase compositions.

[0223] The composition according to the present invention can be transparent.

[0224] Clarity can be measured by measuring turbidity (for example, turbidity can be measured using a 2100Q (commercially available from Hach Company) with a round cell (25 mm diameter and 60 mm height) and a tungsten filament lamp capable of emitting visible light (between 400 and 800 nm, preferably 400 to 500 nm). Measurements can be performed on the undiluted composition. A blank can be determined using distilled water.

[0225] The composition according to the present invention has a turbidity of 120 NTU or less, preferably 90 NTU or less, more preferably 60 NTU or less.

[0226] [Method and Use] The composition according to the invention is preferably a cosmetic or dermatological composition, preferably a skin cosmetic composition, more preferably a skin care cosmetic composition.

[0227] The compositions according to the invention can be used for non-therapeutic methods, such as cosmetic methods, for treating the skin by applying them to the skin.

[0228] The present invention therefore also relates to a cosmetic method for treating keratinous materials such as the skin, comprising the step of applying to the keratinous materials a composition according to the invention.

[0229] The present invention may also relate to the use of a composition according to the invention as or in a cosmetic preparation, such as a skin care product.

[0230] In other words, the composition according to the present invention can be used as a cosmetic by itself. Alternatively, the composition according to the present invention can be used as one component of a cosmetic. For example, the composition according to the present invention can be added to or combined with any other component to form a cosmetic.

[0231] The skin care product may be a lotion, cream, serum, or the like.

[0232] Another aspect of the present invention is also a method for preparing a composition, comprising the steps of: (a) at least one oil; (b) at least one diol having at least one carbon chain containing three or more carbon atoms; (c) at least one skin care active ingredient; (d) Water and The present invention also relates to a method comprising the step of mixing

[0233] The mixing step is preferably carried out by a so-called low-energy process that does not use a special mechanical agitator such as a homogenizer that uses a large amount of energy. The low-energy process can be carried out by simply gently stirring the components (a) to (d).

[0234] Another aspect of the present invention is a method for producing a semiconductor device comprising: (b) at least one diol having at least one carbon chain containing three or more carbon atoms; (a) at least one oil; (c) at least one skin care active ingredient, and (d) water (c) for enhancing or improving the penetration of a skin care active ingredient in a composition comprising:

[0235] The present invention also provides (a) at least one oil, and (d) water In a composition comprising (c) as a skin penetration enhancer for at least one skin care active ingredient, (b) The use of at least one diol having at least one carbon chain containing three or more carbon atoms.

[0236] Preferably, the above-mentioned composition in the uses and methods according to the invention is in the form of a microemulsion, more preferably an O / W microemulsion.

[0237] The above descriptions of components (a) to (d) and optional components of the compositions according to the invention are applicable to those components of the uses and methods according to the invention. The descriptions of the preparation and forms of the compositions according to the invention are also applicable to the preparation and forms of the compositions described in the uses and methods above. [Example]

[0238] The present invention will now be described in more detail by way of examples, which should not be construed as limiting the scope of the present invention.

[0239] (Examples 1 to 6 and Comparative Examples 1 to 12) The following compositions according to Examples 1 to 6 and Comparative Examples 1 to 12 shown in Tables 1 to 3 were prepared by mixing the components shown in Tables 1 to 3 below. The symbols "(a)," "(b)," "(c)," and "(d)" in Tables 1 to 3 correspond to the symbols in the claims. All numerical values ​​for the amounts of components shown in Tables 1 to 3 are based on "mass %" of the active ingredient.

[0240] [Table 1]

[0241] [Table 2]

[0242] [Table 3]

[0243] [evaluation] (Amount of active ingredient penetrated) Permeation experiments were performed in Franz diffusion cells (PermeGear) using a Strat-M membrane (Merck, surface area 1.77 cm). 2 The device consisted of a donor section and a receptor section, with a Strat-M membrane between the donor and receptor sections. The receptor section, having a predetermined volume, was filled with a receiving solution (0.25% by weight Tween 80 / deionized water) maintained at a temperature of 32°C, which was continuously stirred with a small magnetic bar. Each of the compositions according to Examples 1 to 6 and Comparative Examples 1 to 12 was applied to the receptor section at a concentration of 20 mg / cm using a spatula. 2The amount of the receptor solution was spread on the membrane of the donor section. After 1 hour, 200 μl of the receptor solution was removed from the receptor section, and the same amount of fresh receptor solution was supplied to the receptor section to maintain the same permeation conditions. The removed receptor solution was analyzed by HPLC to determine the amount of active ingredient in the receptor solution. The percentage of the active ingredient that passed through the membrane was calculated by dividing the detected amount of active ingredient in the receptor solution by the amount of active ingredient spread on the membrane.

[0244] The results are shown in the row of "Amount of permeated active ingredient" in Tables 1 to 3.

[0245] [summary] Tables 1-3 demonstrate that a composition comprising (a) at least one oil, (b) at least one diol having at least one carbon chain containing three or more carbon atoms, (c) at least one skin care active, and (d) water can enhance skin penetration of (c) the skin care active.

[0246] Tables 1-3 also demonstrate that the use of (b) at least one diol having at least one carbon chain containing three or more carbon atoms in a composition comprising (a) at least one oil, (c) at least one skin care active, and (d) water can enhance or improve the penetration of (c) the skin care active.

Claims

1. (a) At least one oil, and (b) at least one diol having at least one carbon chain containing 3 or more carbon atoms, (c) at least one skin care active ingredient, and (d) water A composition comprising.

2. (a) The oil is selected from the group consisting of (i) aliphatic alcohols, (ii) fatty acids, (iii) monoesters of monocarboxylic acids, (iv) diesters of dicarboxylic acids, (v) N-acyl amino acid esters, and (vi) alkyl lactates, provided that - (i) The aliphatic alcohol and (ii) the fatty acid each have a branched alkyl group, or a linear or branched alkenyl group having 4 to 30 carbon atoms, preferably 5 to 26 carbon atoms, more preferably 6 to 22 carbon atoms, - (iii) The monoesters of monocarboxylic acids each have a branched alkyl group, or a linear or branched alkenyl group having 4 to 30 carbon atoms, preferably 5 to 26 carbon atoms, more preferably 6 to 22 carbon atoms, - (iv) The diesters of dicarboxylic acids contain at least one branched alkyl group having 3 to 10 carbon atoms, preferably 3 to 8 carbon atoms, more preferably 3 to 6 carbon atoms, and an alkylene group having 6 to 18 carbon atoms, preferably 6 to 14 carbon atoms, more preferably 6 to 10 carbon atoms, - (v) The N-acyl amino acid esters contain a branched alkyl group having 3 to 10 carbon atoms, preferably 3 to 8 carbon atoms, more preferably 3 to 6 carbon atoms, and a linear or branched acyl group having 4 to 30 carbon atoms, preferably 5 to 26 carbon atoms, more preferably 6 to 22 carbon atoms, - (vi) The alkyl lactates each have a linear or branched alkyl group, or a linear or branched alkenyl group having 4 to 30 carbon atoms, preferably 5 to 26 carbon atoms, more preferably 6 to 22 carbon atoms, The composition according to claim 1.

3. (a) The oil is an N-acyl amino acid ester containing at least a branched alkyl group having 3 to 10 carbon atoms, preferably 3 to 8 carbon atoms, more preferably 3 to 6 carbon atoms, preferably the following general formula (5): R 2 -N(R 5 )-CH(R 6 )-(CH 2 ) n -COO-R 3 (5) (In the formula, R 2 represents a linear or branched acyl group having 4 to 30 carbon atoms, preferably 5 to 26 carbon atoms, more preferably 6 to 22 carbon atoms, R 3 represents a branched alkyl group having 3 to 10 carbon atoms, preferably 3 to 8 carbon atoms, more preferably 3 to 6 carbon atoms, R 5 represents a hydrogen atom or a linear or branched alkyl group having 1 to 4 carbon atoms, R 6 represents a linear or branched alkyl group having 1 to 4 carbon atoms, which may be substituted by a hydrogen atom, a hydroxy group or a phenyl group, n represents an integer from 0 to 2) Selected from N-acyl amino acid esters represented by, More preferably, (a) the oil is isopropyl lauroyl sarcosinate, The composition according to claim 1.

4. The composition according to claim 1, wherein the amount of (a) oil in the composition is in the range of 0.5% by mass to 25% by mass, preferably 1% by mass to 20% by mass, more preferably 2% by mass to 15% by mass, based on the total mass of the composition.

5. The composition according to claim 1, wherein the diol having at least one carbon chain containing 3 or more carbon atoms in (b) is selected from the group consisting of propylene glycol, dipropylene glycol, polypropylene glycol, butylene glycol, dibutylene glycol, polybutylene glycol, pentylene glycol, dipentylene glycol, hexylene glycol, dihexylene glycol, and mixtures thereof.

6. The composition according to claim 1, wherein the mass ratio of the amount of (b) diol having at least one carbon chain containing 3 or more carbon atoms to the amount of (a) oil is 4 or more, preferably 5 or more, more preferably 6 or more.

7. The composition according to claim 1, wherein the skin care active ingredient in (c) has a Log P value of 4 or less, preferably -4.5 to 4.0, more preferably -4.0 to 3.

5.

8. The composition according to claim 1, wherein the skin care active ingredient in (c) is a skin care cosmetic active ingredient, preferably a skin whitening or anti-wrinkle ingredient, and more preferably is selected from the group consisting of ascorbyl glucoside, 3-O-ethyl ascorbic acid, tranexamic acid, hydroxypropyltetrahydropyrantriol, niacinamide, salicylic acid, phenyl ethyl resorcinol, and mixtures thereof.

9. The composition according to claim 1, wherein the amount of (c) skin care active ingredient in the composition is in the range of 0.01% by mass to 25% by mass, preferably 0.05% by mass to 20% by mass, more preferably 0.1% by mass to 15% by mass, based on the total mass of the composition.

10. The composition according to claim 1, having a turbidity of 120 NTU or less, preferably 90 NTU or less, more preferably 60 NTU or less.

11. The composition according to claim 1, which is a cosmetic composition, preferably a skin cosmetic composition, more preferably a skin care cosmetic composition.

12. A keratinous substance, preferably a cosmetic method for treating the skin, the cosmetic method comprising the step of applying the composition according to any one of claims 1 to 11 to the keratinous substance.