COMPOSITION INCLUDING A BIOSURZAACTIVE AND SALICYLIC ACID
A composition combining glycolipids, salicylic acid derivatives, and cationic polymers addresses the drying issue of anti-acne products, providing hydration and cleansing benefits for acne-prone skin.
Patent Information
- Application Number
- FR2024006067
- Authority / Receiving Office
- FR · FR
- Patent Type
- Utility models
- Current Assignee / Owner
- Filing Date
- 2024-06-10
- Publication Date
- 2025-12-12
- Estimated Expiration
- 2034-06-10
AI Technical Summary
Anti-acne compositions often dry out the skin, lacking sensory and aesthetic benefits while providing inadequate hydration.
A composition comprising glycolipids, salicylic acid derivatives, cationic polymers, and thickeners, formulated to provide hydration and cleansing benefits for acne-prone skin.
The composition effectively moisturizes and cleanses acne-prone skin without drying, offering a unique paste-like texture and improved skin health.
Abstract
Description
Title of the invention: COMPOSITION COMPRISING A biosurfactant and salicylic acid technical field
[0001] The present invention relates to a composition comprising at least one biosurfactant and at least one salicylic acid or its derivatives, preferably a cosmetic composition comprising them. Context of the invention
[0002] Anti-acne cleansing compositions often have the undesirable effect of drying out the skin. Therefore, it is necessary to develop an effective anti-acne composition capable of offering sensory and aesthetic benefits to acne-prone skin and providing adequate hydration. Disclosure of the invention
[0003] An objective of the present invention is to provide a composition for hydrating and / or to cleanse acne-prone skin.
[0004] The above objective of the present invention can be achieved by a composition including: (a) at least one glycolipid; (b) at least one salicylic acid or its derivatives of formula (I): % OH (!) C O in which: - The radical R designates a saturated, linear, branched, or cyclic aliphatic chain containing from 2 to 22 carbon atoms; an unsaturated chain containing from 2 to 22 carbon atoms containing one or more double bonds that may be conjugated; an aromatic ring linked to the carbonyl radical directly or via saturated or unsaturated aliphatic chains containing from 2 to 7 carbon atoms; said groups may optionally be substituted with one or more substituents, which may be identical or different, chosen from halogen atoms, a trifluoromethyl group, hydroxyl groups in free form or esterified with an acid containing from 1 to 6 carbon atoms, or the groups
[0005]
[0006]
[0007]
[0008]
[0009]
[0010]
[0011]
[0012]
[0013]
[0014] carboxyl in free form or esterified with a lower alcohol containing 1 to 6 carbon atoms; - R' is a hydroxyl group or an ester group with the formula: —OC-Rj II O in which Ri denotes a linear or branched aliphatic chain, saturated or unsaturated, containing 1 to 18 carbon atoms; as well as their salts derived from a mineral or organic base; (c) at least one cationic polymer; and (d) at least one thickener. (a) glycolipid is selected from the group consisting of rhamnolipids, sophorolipids, glucolipids, trehalolipids, cellobiose lipids and mixtures thereof. The (b) salicylic acid derivatives are represented by formula (I) in which the radical R denotes a linear, branched or cyclic saturated aliphatic chain, containing from 2 to 22 carbon atoms. The (b) salicylic acid derivatives are represented by formula (I) in which the radical R denotes a linear or branched alkyl or alkenyl group, preferably an alkyl group, containing 2 or more, preferably 3 or more, more preferably 4 or more, even more preferably 5 or more, and in particular 6 or more carbon atoms, and / or 22 or less, preferably 18 or less, even more preferably 14 or less, preferably 12 or less, and in particular 10 or less carbon atoms. The (b) salicylic acid derivatives are represented by formula (I) in which R' denotes a hydroxyl group. The (c) cationic polymer is a polysaccharide derived from D-glucosamine and N-acetyl-D-glucosamine [3-linked. The (d) thickener is a thickener of vegetable origin. The quantity of the (a) glycolipid(s) may be from 0.1% to 10% by weight, preferably from 1% to 7% by weight, more preferably from 2% to 5% by weight, and in particular from 3% by weight, relative to the total weight of the composition. The quantity of (b) salicylic acid or its derivatives may be from 0.1% to 5% by weight, preferably from 1% to 3% by weight, more preferably from 2% by weight, relative to the total weight of the composition. The weight ratio of (a) glycolipid(s) to (b) salicylic acid or its derivatives in the composition may be from 3:1 to 1:3, more preferably from 2:1 to 1:2, most preferably from 3:2.
[0015] The composition according to the present invention may be in the form of a solution, a cream, a lotion, an emulsion or a gel, etc. Preferably, the composition of the present invention has a unique paste-like texture similar to wasabi.
[0016] The composition may further include water in an amount of 20% to 70% by weight, relative to the total weight of the composition.
[0017] The composition may be a cosmetic composition for moisturizing and / or cleansing acne-prone skin.
[0018] The present invention also relates to the use of a combination of (a) glycolipid, (b) salicylic acid or its derivative, (c) cationic polymer, and (d) thickener to moisturize and / or cleanse acne-prone skin. Best embodiment of the invention
[0019] After careful research, the inventors have discovered surprisingly that a composition comprising (a) at least one glycolipid and (b) at least one salicylic acid or its derivatives having the specific structure of formula (I), (c) at least one cationic polymer, and (d) at least one thickener can moisturize and / or cleanse acne-prone skin, thereby accomplishing the present invention.
[0020] Thus, the composition according to the present invention is a composition comprising: (a) at least one glycolipid; (b) at least one salicylic acid or its derivatives of formula (I): % .OH (D THAT .xR! TO in which: - the radical R designates a saturated, linear, branched, or cyclic aliphatic chain containing from 2 to 22 carbon atoms; an unsaturated chain containing from 2 to 22 carbon atoms containing one or more double bonds that may be conjugated; an aromatic ring linked to the carbonyl radical directly or via saturated or unsaturated aliphatic chains containing from 2 to 7 carbon atoms; said groups optionally being substituted with one or more substituents, which may be identical or different, selected from halogen atoms, a trifluoromethyl group, hydroxyl groups in free form or esterified with an acid containing from 1 to 6 carbon atoms, or the groups carboxyl in free form or esterified with a lower alcohol containing 1 to 6 carbon atoms; - R' is a hydroxyl group or an ester group with the formula: in which Ri denotes a linear or branched aliphatic chain, saturated or unsaturated, containing 1 to 18 carbon atoms; as well as their salts derived from a mineral or organic base; (c) at least one cationic polymer; and (d) at least one thickener.
[0021] The composition according to the present invention will be explained in more detail below. [Composition]
[0022] The composition may be a cosmetic composition, preferably a cosmetic composition for a keratinous substance, and more preferably a cosmetic composition for moisturizing and / or cleansing acne-prone skin. The keratinous substance here refers to a material containing keratin as its main constituent, and examples include facial or body skin, scalp, lips, and the like.
[0023] The form of the composition according to the present invention is not particularly limited. In general, the composition according to the present invention can be liquid, semi-liquid, or solid at room temperature (25 °C) and atmospheric pressure (105 Pa). The composition can take various forms, such as a solution, an aqueous solution, a lotion, a milky lotion, a cream, a gel, a liquid gel, a paste, a serum, a suspension, a dispersion, a fluid, a milk, an emulsion (O / W or W / H form), or the like. Preferably, the composition according to the present invention is in the form of a paste. In particular, the composition of the present invention has a unique paste-like texture similar to wasabi.
[0024] The composition according to the present invention can preferably be used as a cosmetic composition, in particular, a rinse-off cosmetic composition. The composition according to the present invention can be intended to be applied to a keratinous substance, preferably the skin, and in particular facial skin.
[0025] The composition according to the present invention comprises (a) at least one glycolipid; (b) at least one salicylic acid or its derivatives according to formula (I); (c) at least one cationic polymer; and (d) at least one thickener. The substances of the composition will be described in detail below.
[0026] (Glycolipid)
[0027] The composition according to the invention comprises one or more glycolipids.
[0028] The term "glycolipid" means a compound formed from a lipid to which one or more carbohydrate compounds are attached.
[0029] One or more glycolipids may be selected from rhamnolipids, sophorolipids, glucolipids, trehalolipids, cellobiose lipids and mixtures thereof.
[0030] The one or more glycolipids are preferably chosen from rhamnolipids, sophorolipids and their mixtures, more preferably rhamnolipids. Glucolipids:
[0031] The one or more glycolipids may be glucolipids, which contain a glucose fraction and may be represented by the general formula (I): P in which: - R1 represents a hydrogen atom or a cation, - p denotes an integer from 1 to 4, and - q denotes an integer from 4 to 10, preferably equal to 6.
[0032] Glycolipids can be produced by the bacterium Alcaligenes sp. MM1.
[0033] The appropriate fermentation processes are reviewed by Mr. Schmidt in his doctoral thesis (1990), Technical University of Braunschweig, and by Schulz et al. (1991) Z. Naturforsch., 46C, 197-203. The glucolipids are recovered from the fermentation broth by solvent extraction using diethyl ether or a dichloromethane:methanol or chloroform:methanol mixture. Sophorolipids
[0034] One or more glycolipids may be sophorolipids, which contain a sophorose fraction and may be represented by the general formula (II): in which: - R3 and R4 individually represent a hydrogen atom or an acetyl group, - R5 represents a saturated or unsaturated hydrocarbon group, hydroxylated or non-hydroxylated, having from 1 to 9 carbon atoms, preferably a methyl group, - R6 represents a saturated or unsaturated hydrocarbon group, hydroxylated or non-hydroxylated, having from 1 to 19 carbon atoms, provided that the total number of carbon atoms in groups R5 and R6 does not exceed 20 and is preferably from 14 to 18.
[0035] Sophorolipids can be incorporated into the composition according to the present invention either in the form of an open-chain free acid, where R7 represents a hydrogen atom and R8 represents a hydroxy group OH, or in its lactone form, where a lactone ring is formed between R7 and R8, as indicated by formula (III): (III) OH in which: - R3, R4, R5 and R6 are as defined above, provided that at least one of R3 and R4 represents an acetyl group.
[0036] Sophorolipids can be produced by yeast cells, for example, Torulopsis apicola and Torulopsis bombicola cells. The fermentation process generally uses sugars and alkanes as substrates.
[0037] Suitable fermentation processes are reviewed in AP Tulloch, JFT Spencer and PAJ Gorin, Can. J. Chem. (1962), 40, 1326, and U. Gobbert, S. Lang and F. Wagner, Biotechnology Letters (1984), 6 (4), 225. The resulting product is a mixture of various open-chain sophorolipids and sophorolipid lactones which can be used in mixtures, or the required form can be isolated.
[0038] It is possible to use as sophorolipids, for example that sold under the name Sopholiance S by Givaudan and that sold under the name BioToLife by BASF. Trehalolipids
[0039] One or more glycolipids may be trehalolipids, which contain a trehalose fragment and may be represented by the general formula (IV): o i i coûh in which: - R9, R10 and R11 individually represent a saturated or unsaturated hydrocarbon radical, hydroxylated or non-hydroxylated, having from 5 to 13 carbon atoms.
[0040] Trehalolipids can be produced by bacterial fermentation using the marine bacterium Arthrobacter sp. Ek 1 or the freshwater bacterium Rhodococcus erythropolis. Suitable fermentation processes are proposed by Ishigami et al. (1987), J. Jpn. Oil Chem. Soc., 36, 847-851, Schultz et al. (1991), Z. Naturforsch., 46C, 197-203, and Passeri et al. (1991), Z. Naturforsch., 46C, 204-209. Cellobiose lipids
[0041] One or more glycolipids may be cellobiose lipids, which contain a cellobiose fragment and may be represented by the general formula (V): R12 in which: - R1 represents a hydrogen atom or a cation, - R12 represents a saturated or unsaturated hydrocarbon radical, hydroxylated or non-hydroxylated, having 9 to 15 carbon atoms, preferably 13 carbon atoms, - R13 represents a hydrogen atom or an acetyl group; - R14 represents a saturated or unsaturated hydrocarbon radical, hydroxylated or non-hydroxylated, having from 4 to 16 carbon atoms.
[0042] Cellobiose lipids can be produced by fungal cells of the genus Ustilago. Suitable fermentation processes are proposed by Frautz, Lang and Wagner (1986), Biotech. Letts., 8, 757-762.
[0043] Rhamnolipids;
[0044] One or more glycolipids may be rhamnolipids.
[0045] The composition according to the invention preferably comprises one or more rhamnolipids.
[0046] Rhamnolipids are glycolipids produced by various bacterial species. They consist of one rhamnose fragment (mono-rhamnolipid) or two rhamnose fragments (di-rhamnolipid) linked by a glycosidic bond to one, two or three [3-hydroxylated] fatty acid chains linked together by an ester bond.
[0047] More specifically, these mono-rhamnolipids and di-rhamnolipids correspond to the following formula (VI): n in which: - m denotes an integer equal to 2, 1 or 0, - n denotes an integer equal to 1 or 0, and - Ri and R2 each independently represent identical or different hydrocarbon radicals having from 2 to 24 carbon atoms, preferably from 5 to 13 carbon atoms, which are branched or unbranched, substituted or unsubstituted, in particular hydroxy-substituted, saturated or unsaturated, preferably an alkyl radical that is simply, doubly or triply unsaturated.
[0048] Thus, when n is equal to 0, formula (VI) protects mono-rhamnolipids and, when n is equal to 1, it protects di-rhamnolipids.
[0049] The composition according to the invention preferably comprises at least one di-rhamnolipid.
[0050] The composition according to the invention preferably comprises at least one di-rhamnolipid of formula (VI) in which:
[0051] - m denotes an integer equal to 2, 1 or 0; - n denotes an integer equal to 1; and - Ri and R2 each independently represent identical or different hydrocarbon radicals, having from 2 to 24 carbon atoms, preferably from 5 to 13 carbon atoms, which are branched or unbranched, substituted or unsubstituted, in particular hydroxy-substituted, saturated or unsaturated, preferably a simply, doubly or triply unsaturated alkyl radical, as well as their salts, solvates and optical isomers.
[0052] The glycosidic linkage between the two rhamnose fragments can be of alpha or beta configuration and is preferably of alpha configuration.
[0053] In the context of the invention,
[0054] - the salts of di-rhamnolipids of formula (VI) are more particularly their salts carboxylates with an organic or inorganic cation, and in particular with a cation chosen from sodium, potassium, calcium and ammonium. - the solvated forms of di-rhamnolipids of formula (VI) are more particularly those solvated by one or more molecules of water or organic solvents, for example a hydrate or a solvate of a linear or branched alcohol, such as ethanol or isopropanol, the optically active carbon atoms of the fatty acids being preferably in the form of the R enantiomers, and - the radical term “alkyl” designates a saturated aliphatic group, linear or branched; for example, an alkyl group in Ci-C2o having a linear or branched hydrocarbon chain of 1 to 20 carbon atoms, more particularly a methyl, ethyl, propyl, isopropyl, butyl, isobutyl, tert-butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, undecyl, dodecyl, tridecyl, tetradecyl, pentadecyl, hexadecyl, heptadecyl, octadecyl, nonadecyl or eicosyl group.
[0055] The composition according to the invention preferably comprises at least one di-rhamnolipid of formula (VI) in which: - m denotes an integer equal to 2, 1 or 0; - n denotes an integer equal to 1; and - Ri and R2, which are identical or different, are chosen from the radicals pentenyl, hexenyl, heptenyl, octenyl, nonenyl, decenyl, undecenyl, dodecenyl, tridecenyl and the radicals of formula -(CH2)OCH3, o designating an integer from 1 to 23, in particular from 3 to 15 and more particularly from 4 to 12.
[0056] According to one embodiment of the invention, the composition according to the invention comprises at least one di-rhamnolipid of general formula (VI) in which m is equal to 1.
[0057] According to one embodiment of the invention, the composition according to the invention comprises a mixture of at least two, preferably at least three, di-rhamnolipids of general formula (VI) in which m is preferably equal to 1.
[0058] According to another embodiment of the invention, the composition according to the invention comprises a mixture comprising at least one mono-rhamnolipid.
[0059] More preferably, the composition according to the invention comprises at least one dirhamnolipid of the following formula (VII): O n in which: - m denotes an integer equal to 2, 1 or 0; preferably, m is equal to 1, - n denotes an integer equal to 1, - Ri is a radical -(CH2)P-CH3, where p is an integer ranging from 1 to 23, preferably from 4 to 12, - R2 is a radical -(CH2)q-CH3, q being an integer ranging from 1 to 23, preferably from 4 to 12, and also their salts, their solvates and their optical isomers.
[0060] By way of illustration and without limiting the di-rhamnolipides of formula (VII) which may be suitable for the invention, particular mention may be made of the compounds of formula di-RL-CXCY, as defined in Table 1 below.
[0061] The formula di-RL-CXCY is a variant of writing to represent a di-rhamnolipid (di-RL) functionalized by two radicals Ri and R2 respectively represented by the symbols CX and CY, the integers X and Y being respectively equal to p+4 and q+4.
[0062] [Tables 1] Compounds D;RL CXCY PQ 1 | dlRL-CSCS 4 4 2 | 4 0 3 «XJIOCS 4 4 m cwia 6 S 5 6 S 6 •^Rl. CIX10 8 6 7 4ihl C î 1 ' R § 8 «L-C12C14 g 10 9 | &RLCMCU 10 S 10 | ÆSL-C14C14 10 10 11 ï 10 12 12 «4» Î2 10 13 | dsRL-ClSC16 12 12
[0063] According to a preferred embodiment, the composition according to the invention comprises at least one di-rhamnolipid of formula (VII) in which p and q are identical and equal to 6 and m is equal to 1, also called di-RL-ClOCIO, or one of its salts, solvated and optical isomers.
[0064] Preferably, the di-rhamnolipid of formula (VII) in which p and q are identical and equal to 6 and m is equal to 1 is present in the composition according to the invention in a proportion of at least 50% by weight and preferably from 51% to 85% by weight, relative to the total weight of the rhamnolipids.
[0065] According to another embodiment, the composition according to the invention comprises at least one di-rhamnolipid of formula (VII) in which m is equal to 1, p is equal to 6 and q is equal to 8.
[0066] According to another embodiment, the composition according to the invention comprises at least one di-rhamnolipid of formula (VI) in which n and m are equal to 1, Ri represents a radical -(CH2)OCH3, with o being an integer ranging from 4 to 12, and R2 is selected from the pentenyl, hexenyl, heptenyl, octenyl, nonenyl, decenyl, undecenyl, dodecenyl and tridecenyl radicals; preferably, Ri represents a radical -(CH2)6CH3 and R2 a nonenyl radical.
[0067] According to another preferred embodiment, the composition according to the invention comprises a mixture of at least two, in particular at least three, di-rhamnolipids of formula (VI) or formula (VII) selected from: - a di-rhamnolipid of formula (VII) in which p and q are identical and equal to 6 and m is equal to 1; - a di-rhamnolipid of formula (VII) in which m is equal to 1, p is equal to 6 and q is equal to 8; and - at least one di-rhamnolipid of formula (VI) in which n and m are equal to 1, Ri represents a radical -(CH2)OCH3, o being an integer ranging from 4 to 12, and R2 is chosen from the pentenyl, hexenyl, heptenyl, octenyl, nonenyl, decenyl, undecenyl, dodecenyl and tridecenyl radicals; preferably, Ri represents a radical -(CH2)6CH3 and R2 a nonenyl radical.
[0068] Preferably, the composition according to the invention comprises a mixture of at least two, in particular at least three, di-rhamnolipids of formula (VI) or formula (VII) selected from: - at least 50% by weight and preferably from 51% to 85% by weight of a di-rhamnolipid of formula (VII) in which p and q are identical and equal to 6 and m is equal to 1, relative to the total weight of the rhamnolipids. - from 0.5% to 25% by weight, preferably from 5% to 15% by weight, of a di-rhamnolipid of formula (VII) in which p is equal to 6, q is equal to 8 and m is equal to 1, relative to the total weight of the rhamnolipids, and - from 0.5 to 15% by weight, preferably from 3% to 12% by weight, preferably from 5% to 10% by weight, of a di-rhamnolipid of formula (VI) in which n and m are equal to 1, Ri represents a -(CH2)6CH3 radical and R2 represents a nonenyl radical, relative to the total weight of rhamnolipids.
[0069] As specified above, rhamnolipids are usually prepared by processes known to those skilled in the art from bacterial producers, such as Pseudomonas.
[0070] Suitable fermentation processes are reviewed by D. Haferburg, R. Hommel, R. Claus and HP Kleber in Adv. Biochem. Ing. / Biotechnol. (1986), 33, 53-90, and by F. Wagner, H. Bock and A. Kretschmar in Fermentation (ed. RM Lafferty) (1981), 181-192, Springer Verlag, Vienna.
[0071] The rhamnolipide sold under the name Rheance One by Evonik (INCI name: glycolipids) can be used as a rhamnolipide.
[0072] The composition according to the invention preferably comprises an amount of glycolipid ranging from 0.1% to 10% by weight, preferably from 1% to 7% by weight and even better from 2% to 5% by weight, relative to the total weight of the cosmetic composition.
[0073]
[0074]
[0075]
[0076]
[0077]
[0078] The composition according to the invention preferably comprises an amount of rhamnolipid ranging from 0.1% to 10% by weight, preferably from 1% to 7% by weight and even better from 2% to 5% by weight, relative to the total weight of the cosmetic composition. (Salicylic acid or its derivatives) The composition according to the present invention comprises (b) at least one salicylic acid or its derivatives according to formula (I). Only one type of salicylic acid or its derivatives may be used, but two or more different types of salicylic acid or its derivatives may be used in combination. The salicylic derivatives according to the present invention correspond to the formula (I): OH (I) C" - R: I O in which: - the radical R designates a saturated, linear, branched or cyclic aliphatic chain containing from 2 to 22 carbon atoms; an unsaturated chain containing from 2 to 22 carbon atoms containing one or more double bonds which may be conjugated; an aromatic ring linked to the carbonyl radical directly or via saturated or unsaturated aliphatic chains containing from 2 to 7 carbon atoms; said groups may optionally be substituted with one or more substituents, which may be identical or different, chosen from halogen atoms, a trifluoromethyl group, hydroxyl groups in free form or esterified with an acid containing from 1 to 6 carbon atoms, or carboxyl groups in free form or esterified with a lower alcohol containing from 1 to 6 carbon atoms; - R' is a hydroxyl group or an ester group with the formula: —O—C—Rx II O in which Ri denotes a linear or branched aliphatic chain, saturated or unsaturated, containing 1 to 18 carbon atoms; as well as their salts derived from an inorganic or organic base. Preferably, the radical R in formula (I) denotes a saturated, linear, branched, or cyclic aliphatic chain containing from 3 to 11 carbon atoms; an unsaturated chain containing from 3 to 17 carbon atoms and comprising a or several conjugated or non-conjugated double bonds; knowing that said hydrocarbon chains may be substituted with one or more substituents, which may be identical or different, chosen from halogen atoms, a trifluoromethyl group, hydroxyl groups in free form or esterified with an acid containing 1 to 6 carbon atoms, or a carboxyl function in free form or esterified with a lower alcohol containing 1 to 6 carbon atoms.
[0079] In a preferred embodiment, the radical R in formula (I) designates a linear or branched alkyl or alkenyl group, preferably an alkyl group, containing 2 or more, preferably 3 or more, more preferably 4 or more, even more preferably 5 or more, and in particular 6 or more carbon atoms, and / or 22 or less, preferably 18 or less, even more preferably 14 or less, preferably 12 or less, and in particular 10 or less carbon atoms.
[0080] Preferably, R' in formula (I) is a hydroxyl group or an ester group of formula: — OC-Rj II O in which Ri denotes a -(CH2)n-CH3 radical where n is a number from 0 to 14.
[0081] Salicylic acid derivatives that are most particularly preferred are those according to formula (I) in which the radical R is a C3-Ci0 alkyl group and / or R' denotes a hydroxyl.
[0082] Other particularly advantageous compounds are those in which R represents a chain derived from caprylic, linoleic, linolenic or oleic acid.
[0083] Another group of particularly preferred salicylic acid derivatives consists of compounds in which the radical R denotes a C3-CiO alkyl group bearing a carboxyl function in free form or esterified with a lower alcohol containing 1 to 6 carbon atoms and R' denotes a hydroxyl.
[0084] Salicylic acid or its derivatives of formula (I) which can be used according to the present invention are described in particular in US patents 6,159,479 and US 5,558,871, FR 2,581,542, US 4,767,750, EP 378,936, US 5,267,407, US 5,667,789, US 5,580,549 and EP-A-570,230.
[0085] Among the particularly preferred salicylic acid derivatives of formula (I), 5-n-octanoylsalicylic acid (or capryloylsalicylic acid) may be mentioned; 5-n-decanoylsalicylic acid; 5-n-dodecanoylsalicylic acid; 5-n-heptyloxysalicylic acid, and their corresponding salts. The derivative in question is preferably 5-n-octanoylsalicylic acid.
[0086] For the purposes of the present invention, salts of salicylic acid or its derivatives are also considered. As salts derived from inorganic bases, one can In particular, those derived from hydroxylated bases of alkali metal or alkaline earth metal, such as sodium hydroxide or potassium hydroxide, and ammonia, should be mentioned. Regarding salts derived from organic bases, those derived from amine or alkanolamine bases are particularly noteworthy.
[0087] (b) Salicylic acid or its derivative(s) may be present in an amount of 0.1% to 5% by weight, preferably 1% to 3% by weight, relative to the total weight of the composition.
[0088] (Cationic Polymer)
[0089] The cationic polymer may be a polysaccharide derived from D-glucosamine and N-acetyl-D-glucosamine [3—linked]. Chitosan is a particularly preferred cationic polymer.
[0090] (Thickener)
[0091] In some cases, the hair cosmetic compositions of this disclosure include at least one stabilizer and / or a thickening agent. The stabilizer and / or the thickening agent(s) may be thickening polymers. Non-limiting examples include acacia, agar, algin, alginic acid, ammonium alginate, amylopectin, calcium alginate, sodium alginate, calcium carrageenan, carnitine, carrageenan, dextrin, gelatin, gellan gum, guar gum, tragacanth gum, acacia gum, gum arabic, hydroxypropyltrimonium guar chloride, hectorite, hyaluronic acid, hydrated silica, hydroxypropyl chitosan, hydroxypropyl guar, karaya gum, kelp, locust bean gum, natto gum, potassium alginate, carrageenan, propylene glycol acrylate, sodium carboxymethyl dextran, sodium carrageenan, tragacanth gum, xanthan gum, modified xanthan gum, biosaccharide gum, chitin, levane, elsinane, collagen, Gelatin, zein, gluten, soy protein, casein and mixtures thereof. In some cases, carrageenan is a particularly preferred stabilizer / thickening agent.
[0092] According to a preferred embodiment of the present invention, the weight ratio of (a) glycolipid(s) to (b) salicylic acid or its derivative(s) in the composition can be from 3:1 to 1:3, preferably from 2:1 to 1:2, more preferably from 3:2.
[0093] In a preferred embodiment of the present invention, the composition comprises: (a) at least one biosurfactant selected from rhamnolipids and sophorolipids; and (b) at least one salicylic acid or its derivatives according to formula (I): % ,0H (1) (Y R. 1* Y O in which the radical R in formula (B) denotes a linear or branched alkyl or alkenyl group, preferably an alkyl group, containing 2 or more, preferably 3 or more, more preferably 4 or more, even more preferably 5 or more, and in particular 6 or more carbon atoms, and / or 22 or less, preferably 18 or less, even more preferably 14 or less, preferably 12 or less, and in particular 10 or less carbon atoms, and R' is a hydroxyl group; (c) at least one cationic polymer which may be a polysaccharide derived from D-glucosamine and N-acetyl-D-glucosamine [3-linked]; and (d) at least one thickener.
[0094] (Cosmetically acceptable hydrophilic organic solvent)
[0095] The composition according to the present invention may comprise at least one cosmetically acceptable hydrophilic organic solvent. The term "hydrophilic" here refers to substances having a solubility of at least 1 g / L, preferably at least 10 g / L, and more preferably at least 100 g / L, in water at room temperature (25 °C) and atmospheric pressure (105 Pa).Cosmetically acceptable hydrophilic organic solvent(s) may include, for example, substantially linear or branched lower monoalcohols having 1 to 8 carbon atoms, such as ethanol, propanol, butanol, isopropanol and isobutanol; aromatic alcohols, such as benzyl alcohol and phenylethyl alcohol; polyols or polyol ethers, such as propylene glycol, dipropylene glycol, isoprene glycol, butylene glycol, pentylene glycol, glycerin, propanediol, caprylyl glycol, sorbitol, monomethyl, monoethyl and monobutyl ethers of ethylene glycol, propylene glycol ethers, such as monomethyl propylene glycol ether, alkyl diethylene glycol ethers, such as monoethyl or monobutyl diethylene glycol ether; Polyethylene glycols, such as PEG-4, PEG-6 and PEG-8, and their derivatives, and any combination thereof.
[0096] The amount of cosmetically acceptable hydrophilic organic solvent(s) in the composition according to the present invention may be 1% by weight or more, preferably 2% by weight or more, and more preferably 5% by weight or more, and may be 25% by weight or less, preferably 20% by weight or less, and more preferably 15% by weight or less, relative to the total weight of the composition.
[0097] (pH correcting agent)
[0098] The pH of the composition according to the present invention can be corrected to the desired value using at least one pH correcting agent, such as an acidifying agent or a basifying agent, for example, which are commonly used in cosmetic products.
[0099] The pH of the composition according to the present invention can be from 9 to 3, more preferably from 7 to 4 and most preferably from 6 to 5. In particular, the most preferred pH is 5.5.
[0100] Examples of acidifying agents include mineral or organic acids such as hydrochloric acid, orthophosphoric acid, sulfuric acid, carboxylic acids such as acetic acid, tartaric acid, citric acid, lactic acid and sulfonic acids.
[0101] Examples of alkalizing agents include hydroxides of an alkali or alkaline earth metal, for example sodium hydroxide or potassium hydroxide; quaternary ammonium hydroxides and guanidinium hydroxide; alkali metal silicates, such as sodium metasilicates; amino acids, preferably basic amino acids, such as arginine, lysine, omithine, citrulline, and histidine; carbonates and bicarbonates, in particular of a primary, secondary, or tertiary amine, of an alkali or alkaline earth metal, or of ammonium; and compounds of the following formula: Rx^ Rz X N WN X RT in which - W is an alkylene residue in Ci-C6 optionally substituted by a hydroxyl group or an alkyl group in Ci-C6; - Rx, Ry, Rz and Rt, which may be identical or different, represent a hydrogen atom or an alkyl group in Ci-C6, hydroxyalkyl in Ci-C6 or aminoalkyl in Ci-C6. Notable examples include 1,3-diaminopropane, 1,3-diamino-2-propanol, spermine and spermidine.
[0102] The pH correcting agent(s) may be used in an amount from 0.001% to 10% by weight, preferably from 0.01% to 5% by weight, and more preferably from 0.1% to 3% by weight, relative to the total weight of the composition.
[0103] (Water)
[0104] The composition according to the present invention preferably includes water.
[0105] The amount of water in the composition according to the present invention can be from 20% to 70% by weight, relative to the total weight of the composition.
[0106] (Optional Additions)
[0107] The composition according to the present invention may also include any optional additive(s) commonly used in the field of cosmetics, chosen, for example, from anionic, cationic, non-ionic or amphoteric polymers, anionic, cationic, non-ionic or amphoteric surfactants, oils, hydrophobic organic solvents, gums, resins, thickeners, dispersants, antioxidants, buffers, organic and inorganic fillers, preservatives, such as phenoxyethanol, perfumes, neutralizers, antiseptics, UV screens, cosmetic active agents, such as vitamins, moisturizers, emollients or collagen protectants, and mixtures thereof.
[0108] As antiseptics, those generally used for cosmetics can be used. Specific examples of antiseptics include, for instance, ethanol, triclosan, piroctone olamine, triclocarban, parabens, acrinol, an alkyldiaminoglycine or one of their salts, povidone-iodine, potassium iodide, iodine, 1,2-pentanediol, halocarban, 3,4,4-trichlorocarbanilide, triethyl citrate, resorcinol, hexachlorophene, silver-supported zeolite, silver-supported silica, gluconic acid, benzoic acid, sodium benzoate, undecylenic acid, salicylic acid, sorbic acid or one of its salts, dehydroacetic acid or one of its salts, methylparaben, ethylparaben, propyl paraoxybenzoate, isopropyl paraoxybenzoate, butyl paraoxybenzoate, isobutyl paraoxybenzoate, benzyl paraoxybenzoate;Phenols such as isopropylmethylphenol, chlorhexidine gluconate, cresol, timol, parachlorophenol, phenyl alcohol, phenylphenol, sodium phenylphenol, sodium phenoxyethanol, phenoxydiglycol, phenol, benzyl alcohol; tertiary ammonium salts such as stearyltrimethylammonium chloride, cetyltrimethylammonium chloride, cetylpyridinium chloride, benzalconium chloride, benzethonium chloride, methylbenzethonium chloride, lauryltrimethylammonium chloride, alkylisoquinolium bromide, domiphenone bromide; plant extracts such as tea extract, hinokithiol, apple extract; chloramine T, chlorhexidine, benzoic acid and mixtures thereof.
[0109] The antiseptic or antiseptics may be used in an amount ranging from 0.001% to 10% by weight, preferably from 0.01% to 5% by weight, and more preferably from 0.1% to 3% by weight, relative to the total weight of the composition.
[0110] The composition according to the present invention can be prepared by mixing the essential and optional ingredients described above in a conventional manner. If at least one of the above ingredients is solid at room temperature, the ingredient can be heated until it dissolves. It is further possible to include mixing any one of the optional ingredients and heating the composition until one of the ingredients dissolves.
[0111] (Method for hydrating and / or cleansing acne-prone skin)
[0112] The present invention also relates to a method of hydration and / or cleansing acne-prone skin including the scalp, lips, and especially facial skin, including: the application to the keratinous substance of a composition comprising: at least one glycolipid; at least one salicylic acid or its derivatives of formula (I) above; at least one cationic polymer; and at least one thickener.
[0113] The cleanability of acne-prone skin is calculated as follows: Cleanability = ^^iehaatittou cleaned'^^black reference ^^referred to clean black
[0114] I ô 2 7 De = pr+Da +D^ * From: color difference in a rectangular coordinate system * Black reference: biopeau with sebolution applied after the deep pore cleansing protocol * Proper reference: clean skin bio-skin without any sebum
[0115] The composition is generally applied to a keratinous substance, such as skin, using the hands or an applicator. The present invention may include an optional step of rinsing the composition from the keratinous substance after its application.
[0116] The same explanations on the composition
[0117] at least one glycolipid;
[0118] at least one salicylic acid or its derivatives of formula (I) above;
[0119] at least one cationic polymer; and
[0120] at least one thickener
[0121] as a composition according to the present invention can be applied to the composition,
[0122] at least one glycolipid;
[0123] at least one salicylic acid or its derivatives of formula (I) above;
[0124] at least one cationic polymer; and
[0125] at least one thickener
[0126] for the process
[0127] The composition used in the process according to the present invention may include any of the optional ingredients explained above for the composition according to the present invention. EXAMPLES
[0128] The present invention will be described in more detail by means of examples which, however, shall not be construed as limiting the scope of the present invention. [Examples 1 to 11 of the present invention]
[0129] Compositions of Examples 1 to 11 were prepared by mixing the ingredients as listed in Table 2 with a magnetic stirrer. The numerical values of the quantities of ingredients shown in Table 2 are all based on "% by weight" of active raw materials. The Rhamnolipids were obtained from EVONIK (trade name: RHEANCE One). [Results of the hydration study]
[0130] Examples 8-11 were evaluated against petroleum jelly (positive control) and bare skin for moisturizing properties. Subjects cleaned each palmar forearm with a wipe soaked in 70% isopropyl alcohol. The skin was allowed to air dry for thirty (30) minutes prior to baseline measurements, with the palmar forearms exposed in a room under controlled temperature and humidity conditions. Baseline measurements of each site were taken with the Comeometer 825. Additional measurements were taken at 15 minutes and one hour.
[0131] [Tables2 Ingredient Function Ex. 1 Ex. 2 Ex. 3 Ex. 4 Ex. 5 Ex. 6 Ex. 7 Ex. 8 Ex. 9 Ex. 10 Ex. 11 Sodium Hydroxide Active Compound 0.35 0 0.3 50 0.3 00 0.3 00 0.3 00 0.3 00 0.3 50 0.4 50 0.4 50 0.25 0 0.4 50 Tartaric Acid Active Compound 0.2 00 Lactic Acid Active Compound 0.05 0 0.0 50 0.0 50 0.0 50 0.0 50 0.0 50 0.05 0 0.0 50Ethylenedia mine disuccinate trisodi c Active compound 0.50 0 0.5 00 0.5 00 0.5 00 0.5 00 0.5 00 0.5 00 0.5 00 0.50 0 0.5 00 Sodium lauroyl lac tylate (and) Mixture of ceramides (and) of phyto-sphi ngosine (and) cholesterol (and) xan thane gum (and) carbomer Active compound 0.25 0 0.2 50 0.2 50 0.2 50 0.2 50 0.2 50 0.2 50 0.2 50 0.2 50 0.25 0 0.2 50 Cetyl alcohol Fatty compound 2.50 0 2.5 00 2.5 00 2.5 00 2.5 00 2.5 00 2.5 00 2.5 00 2.5 00 2.50 0 2.5 00 Kaolin Filler 15.0 15.0 15.0 15.0 15.0 15.0 15.0 10.0 15.0 15.0 15.0 Carrageena Polymer 1.0 1.0 1.0 1.0 1.0 1.0 1.0 0.8 1.0 1.0 1.0 Chitosan Polymer 0.10 0.10 0.10 0.10 0.10 0.10 0.10 0.10 0.1 0 0.10 0.10 Salicylic acid Active 2.0 2.0 2.0 2.0 2.0 2.0 2.0 2.0 2.0 2.0 2.0 Phenoxyethanol Preservative 0.30 0.30 Water Solvent 55.9 5 51.25 56.35 56.65 51.30 56.30 55.95 23.35 48.15 48.3 5 28.15 Glycerin Solvent 2.0 2.0 2.0 2.0 2.0 2.0 2.0 40.0 10.0 10.0 30.0 Glyceryl stearate SE Surfactant Active 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 , Sodium cocoyl iseth ionate Surfactant 10.0 10.0 10.0 10.0 10 .0 10.0 10.0 Sodium methyl coco yl taurate Surfactant 10.0 5.0 10.0 10.0 5.0 10.0 Rhamnolipi des Surfactant 3.0 3.0 3.0 3.0 3.0 3.0 3.0 3.0 3.0 3.0 3.0 Active Niacinamide 2.0 2.0 2.0 2.0 2.0 2.0 2.0 2.0 2.0 2.0 2.0
[0132] The results of the hydration study are provided in Table 3, with values indicating the hydration level at the reference, at 15 minutes, and at 1 hour. As shown in Table 3, Examples 8 to 11 were effective in hydrating the skin at 15-minute and one-hour intervals, relative to the reference, as well as evaluated against petroleum jelly (positive control) and bare skin.
[0133] [Tables3] Example Reference 15 min Ih Petrolatum 31.47 + 4.60 37.00 + 9.34 39.36 + 8.06 Naked (wet) 31.92 + 4.82 30.37 + 7.10 30.88 + 7.09 Ex. 8 31.54 + 5.40 45.47 + 9.30 45.71 + 10.23 Ex. 10 30.12 + 5.36 32.28 + 7.64 32.83 + 7.70 Ex. 9 29.16 + 4.94 36.07 + 8.14 35.38 + 8.35 Ex. 11 30.28 + 4.98 37.58 + 7.42 38.37 + 8.78 [Examples 12 to 16 of the present invention]
[0134] Compositions of Examples 12 to 19 were prepared by mixing the ingredients as listed in Table 4 with a magnetic stirrer. The numerical values of the quantities of ingredients shown in Table 4 are all based on the "% by weight" as active raw materials. The Rhamnolipids were obtained from EVONIK (trade name: RHEANCE One).
[0135] [Tables4] INCI name Type of cosmetic Ex 12 Ex 13 Ex 14 Ex 15 Ex 16 Ex 17 Ex 18 Ex 19 sodium hydroxide (sodium hydroxide) active compound 0.45 0.40 0.45 0.35 0.30 0.30 0.45 0.45 niacinamide active compound 2.00 2.00 2.00 2.00 2.00 2.00 2.00 2.00 glyceryl stearate SE (glyceryl stearate SE) surfactant 5.00 5.00 5.00 5.00 5.00 5.00 5.00 5.00 carrageenan (carrageenan) polymer 1.00 1.00 1.00 1.00 1.00 1.00 0.80 1.00 salicylic acid (salicylic acid) active compound 2.00 2.00 2.00 2.00 2.00 2.00 2.00 2.00 phenoxyethanol (preservative) 0.30 water (solvent) 28.15 47.70 48.15 55.95 51.30 56.30 23.35 38.15 glycerin (solvent) 30.00 10.00 10.00 2.00 2.00 2.00 40.00 20.00 lactic acid (active compound) 0.05 0.05 0.05 0.05 0.05 0.05 0.05 0.05 cetyl alcohol (fatty compound) 2.50 2.50 2.50 2.50 2.50 2.50 2.50 2.50 kaolin filler 15.00 15.00 15.00 15.00 15.00 15.00 10.00 15.00 sodium coco yl isethionate (sodium cocoyl iseth ionate) surfactant 10.00 10.00 10.00 10.00 10.00 10.00 10.00 trisodium ethylenodiamine disuccinate (trisodium ethylenediamine disuccinate) active compound 0.50 1.00 0.50 0.50 0.50 0.50 0.50 0.50 sodium lauroyl lactylate (and) ceramide np (and) ceramide de ap (and) phytosphingosine (and) cholesterol (and) xanthan gum (and) carbomer (and) ceramide eop active compound 0.25 0.25 0.25 0.25 0.25 0.25 0.25 0.25 glycolipids (glycolipids) surfactant 3.00 3.00 3.00 3.00 3.00 3.00 3.00 3.00 chitosan (chit osane) polymer 0.10 0.10 0.10 0.10 0.10 0.10 0.10 0.10 sodium methyl cocoyl taurate (sodium methyl cocoyl taurate) surfactant 10.00 5.00
[0136] [Results of the sebum control study]
[0137] Sebum control studies were carried out according to the following procedure:
[0138] Wash the face with water and acclimate it under standard conditions for 30 minutes
[0139] Measurement of the reference T0 on Lightcam
[0140] Application of the product according to randomization using a standard application technique
[0141] Subjects must wait for 10 minutes under standard conditions.
[0142] Measurement of T imm on Lightcam
[0143]
[0144]
[0145]
[0146]
[0147]
[0148]
[0149]
[0150]
[0151]
[0152]
[0153]
[0154] Subjects must wait for the next 4 hours under standard conditions for the following instrumental measurements The results of the sebum control study presented in Table 5 indicate that Examples 12 and 13 exhibited a significant reduction in sebum, which exceeded the performance of some of the best reference products on the market. [Tables 5] Gloss change Ex 13 -2.47 Ex 12 -2.48 [Results of the cleanability study] Cleanability studies were conducted according to the procedure illustrated below. In short, first apply the sebolution and take a photo at T0, then dilute the cleanser and apply it to the sebolution, and finally massage it in, taking another photo at TL The cleanability calculation is also illustrated below. The results are shown in Table 6. As shown in Table 6, Examples 17, 18, 14 and 12 achieved good cleanability, comparable to the cleanability of reference cleaning products on the markets. Pre-cleaning with 730327 27, 2 pg / cm2, Water product ~ 2:1 (weight), 18 circles, Wash mixture, 2 pg / cm2, Water product 2:1 (weight), mixture, Massage of skin; and massage with 5 circles, Use, etc. Wipe with a damp cotton ball, z times Wipe with damp cotton. twice Cleanability -n;--------:------------------------------- ^^own reference ^'^rcjcrence noire F — — —■ De^pl2+Da + Df * From: color difference in a rectangular coordinate system * Black reference: biopeau with sebolution applied after the protocol of deep pore cleansing * Proper reference: clean skin biopeau without any sebolution [Tables] % cleanability Ex 17 67 Ex 18 72 Ex 14 88 Ex 12 85 [Results of the C. acne study]
[0155] The C. acne studies were carried out according to the standard procedure of the Microbiology department I_M_ANA_006_01 “Activity of formulas against microorganisms of cosmetic interest”.
[0156] In summary, in a suitable culture medium, we evaluated the biocidal effect of the 10% formulations on the strain of interest after 2 h, 6 h, and 24 h contact times, compared to a control (medium without formulation). The reduction in the number of viable bacteria is measured over time. This assay is an antimicrobial efficacy or "Time Kill" test.
[0157] The results of C. acne for logarithmic reduction compared to the control are shown in Table 7. The results of the C. acne study for Examples 17, 18, 14 and 12 indicate a satisfactory level of reduction.
[0158] It should be noted that Examples 17, 18, 14, and 12 had a pH of approximately 5.5. We also observed that the pH of the samples had a significant effect on the reduction of C. acne. The results for C. acne for logarithmic reduction with pH effect are presented in Table 8. A lower pH of 5.5 significantly improved the reduction of C. acne compared to a pH of 7.2.
[0159] [Tables7] 2H 6H 24H Ex 17 Acne cleansing paste 2% glycerin 0.6 1 2.3 Ex 18 Acne cleansing paste 40% glycerin 0.4 0.8 2 Ex 14 Acne cleansing paste 10% glycerin 0.6 0.9 2 Ex 12 Acne cleansing paste 30% glycerin 0.6 1 2
[0160] [Tables8] Logarithmic reduction compared to the control 2H 6H 24H pH 5.5 Ex 16 Acne cleansing paste 2% glycerin + 10% sodium cocoyl isethionate 1.9 3.9 5 Ex 15 Acne cleansing paste 2% glycerin 1.5 1.4 4.1 pH 7.2 Ex 16 Acne cleansing paste 2% glycerin + 10% sodium cocoyl isethionate 0 0.2 0.6 Ex 15 Acne cleansing paste 2% glycerin 0 0 0
Claims
1. Demands Cosmetic composition including: (a) at least one glycolipid; (b) at least one salicylic acid or its derivatives of formula (I): % OH (D C'"
2. in which: - the radical R designates a saturated, linear, branched or cyclic aliphatic chain containing from 2 to 22 carbon atoms; an unsaturated chain containing from 2 to 22 carbon atoms containing one or more double bonds which may be conjugated; an aromatic ring linked to the carbonyl radical directly or via saturated or unsaturated aliphatic chains containing from 2 to 7 carbon atoms; said groups may optionally be substituted with one or more substituents, which may be identical or different, chosen from halogen atoms, a trifluoromethyl group, hydroxyl groups in free form or esterified with an acid containing from 1 to 6 carbon atoms, or carboxyl groups in free form or esterified with a lower alcohol containing from 1 to 6 carbon atoms; - R' is a hydroxyl group or an ester group with the formula: —OC-Rt II O in which Ri designates a linear or branched aliphatic chain, saturated or unsaturated, containing 1 to 18 carbon atoms; as well as their salts derived from a mineral or organic base; (c) at least one cationic polymer selected from a polysaccharide derived from D-glucosamine and N-acetyl-D-glucosamine [3-linked]; and (d) at least one thickener. Composition according to claim 1, wherein the glycolipid is selected from the group consisting of rhamnolipids, sophorolipids, glucolipids, trehalolipids, cellobiose lipids and mixtures thereof.
3.
4.
5.
6.
7.
8.
9. Composition according to claim 1, wherein the salicylic acid derivatives are represented by a formula (I) in which the radical R denotes a linear, branched or cyclic saturated aliphatic chain, containing from 2 to 22 carbon atoms. Composition according to claim 1, wherein salicylic acid or its derivatives are salicylic acid. Composition according to claim 1, wherein the amount of glycolipid(s) is from 2% by weight to 5% by weight, relative to the total weight of the composition. Composition according to claim 1, wherein the amount of salicylic acid or its derivatives is from 1% by weight to 3% by weight, relative to the total weight of the composition. Composition according to claim 1, wherein the cationic polymer is chitosan. Composition according to claim 1, wherein the composition is in the form of a paste. Composition according to claim 1, wherein the composition is a cosmetic composition for moisturizing and / or cleansing acne-prone skin.
Citation Information
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