WO2014098254A1 - Composition cosmétique anhydre - Google Patents

Composition cosmétique anhydre Download PDF

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Publication number
WO2014098254A1
WO2014098254A1 PCT/JP2013/084771 JP2013084771W WO2014098254A1 WO 2014098254 A1 WO2014098254 A1 WO 2014098254A1 JP 2013084771 W JP2013084771 W JP 2013084771W WO 2014098254 A1 WO2014098254 A1 WO 2014098254A1
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Prior art keywords
cosmetic composition
composition according
phase
anhydrous cosmetic
nonionic surfactant
Prior art date
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PCT/JP2013/084771
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English (en)
Inventor
Arno WAHLER
Maxime De Boni
Anne-Laure Bernard
Jinglan Li
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L'oreal
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Publication of WO2014098254A1 publication Critical patent/WO2014098254A1/fr

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Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/34—Alcohols
    • A61K8/345—Alcohols containing more than one hydroxy group
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/02—Cosmetics or similar toiletry preparations characterised by special physical form
    • A61K8/03—Liquid compositions with two or more distinct layers
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/31—Hydrocarbons
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/39—Derivatives containing from 2 to 10 oxyalkylene groups
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
    • A61K8/84—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions otherwise than those involving only carbon-carbon unsaturated bonds
    • A61K8/86—Polyethers
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q1/00—Make-up preparations; Body powders; Preparations for removing make-up
    • A61Q1/14—Preparations for removing make-up
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00—Preparations for care of the skin
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q5/00—Preparations for care of the hair
    • A61Q5/02—Preparations for cleaning the hair
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q5/00—Preparations for care of the hair
    • A61Q5/12—Preparations containing hair conditioners
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
    • A61K2800/20—Chemical, physico-chemical or functional or structural properties of the composition as a whole
    • A61K2800/30—Characterized by the absence of a particular group of ingredients
    • A61K2800/31—Anhydrous

Definitions

  • the present invention relates to an anhydrous cosmetic composition which can be separated into a plurality of liquid phases which are visually distinct.
  • Oils are commonly used in cosmetics in order to, for example, provide conditioning effects for skin or hair, or remove a make-up.
  • oils are well known to provide softness and brightness to the hair.
  • the feeling to touch provided by the application of oils onto hair may not be preferable.
  • hair cosmetics for conditioning the hair are often based on emulsions which include water and some conditioning agents such as oils, as well as, typically, cationic agents. Due to the anionic nature of the hair, some cationic agents are electrochemically adsorbed on the hair to provide softness to the hair.
  • hair cosmetic for deterging the hair includes emulsions which include water and some surfactants which can solublize sebum on the hair by incorporating it into micelles.
  • rinse-off skin care oils are often used for body to provide moisture to the skin.
  • rinse-off skin care oils are not always sufficient. Furthermore, they are expensive. Also, cleansing oils are used in particular in Asian countries to remove eye and face make-up.
  • At least one oil as a conditioner is combined with at least one surfactant as an emulsifier or detergent, and with a polar phase such as water.
  • a surfactant as an emulsifier or detergent
  • a polar phase such as water.
  • An objective of the present invention is to provide a cosmetic composition which can stimulate visually potential consumers while it can provide good cosmetic effects such as conditioning and cleansing effects, and can be easily rinsed off and very easily applied on skin or hair, with no dripping, because of its texture.
  • anhydrous cosmetic composition comprising:
  • the nonionic surfactant is selected from esters of polyols with fatty acids with a saturated or unsaturated chain containing for example from 8 to 24 carbon atoms, preferably 12 to 22 carbon atoms, and alkoxylated derivatives thereof with a number of alkyleneoxide of from 10 to 200.
  • the three phases i.e., the (a) oil phase, the (b) alcohol phase, and the (c) nonionic surfactant phase in the anhydrous cosmetic composition according to the present invention be visually distinct after coming in a state of rest.
  • the (c) nonionic surfactant phase in the anhydrous cosmetic composition according to the present invention be present between the (a) oil phase and the (b) alcohol phase.
  • the oil may be selected from the group consisting of aliphatic hydrocarbons, preferably mineral oils.
  • the amount of the (a) oil phase may range from 10 to 80% by weight, preferably from 20 to 70% by weight, and more preferably from 30 to 60% by weight, relative to the total weight of the composition.
  • the alcohol may be selected from polyols, preferably glycerins and derivatives thereof, and glycols and derivatives thereof. It is more preferable that the polyol be selected from the group consisting of glycerin, diglycerin, polyglycerin, ethyleneglycol, diethyleneglycol, propyleneglycol, dipropyleneglycol, butyleneglycol, pentyleneglycol, hexyleneglycol, 1,3 -propanediol, and
  • the amount of the (b) alcohol phase may range from 5 to 80% by weight, preferably from 8 to 70% by weight, and more preferably from 10 to 60% by weight, relative to the total weight of the composition.
  • the nonionic surfactant may have an HLB value of 18.0 or less, preferably from 4.0 to 18.0, more preferably from 6.0 to 15.0, and even more preferably from 9.0 to 13.0.
  • the nonionic surfactant may be selected from glyceryl esters of a C 8 -C24 fatty acid or acids and alkoxylated derivatives thereof with a number of alkyleneoxide of from 10 to 200, polyethylene glycol esters of a C 8 -C 24 fatty acid or acids and alkoxylated derivatives thereof with a number of alkyleneoxide of from 10 to 200, sorbitol esters of a Cs-C2 4 fatty acid or acids and alkoxylated derivatives thereof with a number of alkyleneoxide of from 10 to 200, sugar (sucrose, glucose, alkylglycose) esters of a C 8 -C 24 fatty acid or acids and alkoxylated derivatives thereof with a number of alkyleneoxide of
  • the nonionic surfactant be selected from the group consisting of PEG-20 methylglucoside sesquistearate, PEG-20 glyceryl tri-isostearate, PG-10 isostearate, and PEG-60 hydrogenated castor oil.
  • the amount of the (c) nonionic surfactant phase may range from 0.1 to 50% by weight, preferably from 0.5 to 40% by weight, and more preferably from 1 to 30% by weight, relative to the total weight of the composition.
  • the anhydrous cosmetic composition according to the present invention may further comprise water in an amount of 1% by weight or less relative to the total weight of the composition.
  • the present invention also relates to a cosmetic process for keratin substance comprising the step of applying the anhydrous cosmetic composition according to the present invention to dry or wet keratin substance such as hair and skin.
  • the cosmetic process for keratin substance according to the present invention comprise the step of mixing the (a) oil phase, the (b) alcohol phase and the (c) nonionic surfactant phase in the anhydrous cosmetic composition before the step of applying the anhydrous cosmetic composition to the keratin substance.
  • the cosmetic composition according to the present invention is anhydrous and comprises: (a) at least one oil phase including at least one oil;
  • the nonionic surfactant is selected from esters of polyols with fatty acids with a saturated or unsaturated chain containing for example from 8 to 24 carbon atoms, preferably 12 to 22 carbon atoms, and alkoxylated derivatives thereof with a number of alkyleneoxide of from 10 to 200.
  • the anhydrous cosmetic composition according to the present invention can have multiple liquid phases. Each liquid phase can provide any independent visual effect. Thus, the multi liquid phases can provide unique appearances to the anhydrous cosmetic composition according to the present invention.
  • the multiple liquid phases can disappear when mixing them by, for example, shaking the anhydrous cosmetic composition according to the present invention to form a uniform phase.
  • the uniform phase can separate into the multiple liquid phases again by leaving it, without any shear force, in a certain period of time such as from few minutes to several hours.
  • each of the phases constituting the anhydrous cosmetic composition according to the present invention will be described in a detailed manner.
  • the cosmetic composition according to the present invention includes at least one oil phase including at least one oil. Two or more oils may be used in combination.
  • the oil phase is in the form of a liquid at ambient temperature such as 25°C under atmospheric pressure (760 mmHg or 10 5 Pa).
  • the oil used in the present invention does not contain a polyalkylenated or
  • the oil may be selected from the group consisting of oils of animal or plant origin, mineral oils, synthetic glycerides, esters of fatty alcohols and/or fatty acids other than animal or plant oils and synthetic glycerides, fatty alcohols, non salified fatty acids, silicone oils and aliphatic
  • hydrocarbons These fatty materials may be volatile or non-volatile. It is preferable that the oil be selected from aliphatic hydrocarbons, plant oils, fatty alcohols, esters of fatty alcohols and/or fatty acids other than animal or plant oils and synthetic glycerides, or mixtures thereof. It is more preferable that the oil be selected from the group consisting of aliphatic hydrocarbons, in particular mineral oils.
  • aliphatic hydrocarbons examples include linear or branched hydrocarbons such as mineral oils (e.g., liquid paraffin), paraffin, vaseline or petrolatum, naphthalenes, and the like; hydrogenated polyisobutene, isoeicosan, polydecenes, hydrogenated polyisobutenes such as Parleam, and decene/butene copolymer; and mixtures thereof.
  • aliphatic hydrocarbons mention may also be made of linear or branched, or possibly cyclic C 6 -Ci 6 lower alkanes. Examples that may be mentioned include hexane, undecane, dodecane, tridecane and isoparaffins such as isohexadecane and isodecane.
  • silicone oils mention may be made of, for example, linear organopolysiloxanes such as dimethylpolysiloxane, methylphenylpolysiloxane, methylhydrogenpolysiloxane, and the like; cyclic organopolysiloxanes such as octamethylcyclotetrasiloxane,
  • decamethylcyclopentasiloxane dodecamethylcyclohexasiloxane, and the like; and mixtures thereof.
  • plant oils mention may be made of, for example, linseed oil, camellia oil, macadamia nut oil, sunflower oil, apricot oil, soybean oil, arara oil, hazelnut oil, corn oil, mink oil, olive oil, avocado oil, sasanqua oil, castor oil, safflower oil, jojoba oil, sunflower oil, almond oil, grapeseed oil, sesame oil, soybean oil, peanut oil, and mixtures thereof.
  • animal oils mention may be made of, for example, squalene, perhydrosqualene and squalane.
  • esters of fatty alcohols and/or of fatty acids which are advantageously different from the animal or plant oils as well as the synthetic glycerides mentioned above, mention may be made especially of esters of saturated or unsaturated, linear or branched -C26 aliphatic mono- or polyacids and of saturated or unsaturated, linear or branched Ci-C 26 aliphatic mono- or polyalcohols, the total carbon number of the esters being greater than or equal to 10.
  • dihydroabietyl behenate octyldodecyl behenate; isocetyl behenate; cetyl lactate; C 12 -C 15 alkyl lactate; isostearyl lactate; lauryl lactate; linoleyl lactate; oleyl lactate; (iso)stearyl octanoate; isocetyl octanoate; octyl octanoate; cetyl octanoate; decyl oleate; isocetyl isostearate; isocetyl laurate; isocetyl stearate; isodecyl octanoate; isodecyl oleate; isononyl isononanoate; isostearyl palmitate; methylacetyl ricinoleate; myristyl stearate;
  • octyldodecyl erucate oleyl erucate
  • ethyl and isopropyl palmitates 2-ethylhexyl palmitate, 2-octyldecyl palmitate
  • alkyl myristates such as isopropyl, butyl, cetyl, 2-octyldodecyl, myristyl or stearyl myristate, hexyl stearate, butyl stearate, isobutyl stearate
  • dioctyl malate hexyl laurate
  • 2-hexyldecyl laurate 2-hexyldecyl laurate.
  • esters of C4-C22 dicarboxylic or tricarboxylic acids and of C 1 -C 22 alcohols and esters of mono-, di- or tricarboxylic acids and of C2-C 26 di-, tri-, tetra- or pentahydroxy alcohols may also be used.
  • diethyl sebacate diisopropyl sebacate; diisopropyl adipate; di-n-propyl adipate; dioctyl adipate; diisostearyl adipate; dioctyl maleate; glyceryl undecylenate; octyldodecyl stearoyl stearate; pentaerythrityl monoricinoleate; pentaerythrityl tetraisononanoate; pentaerythrityl tetrapelargonate; pentaerythrityl tetraisostearate; pentaerythrityl tetraoctanoate; propylene glycol dicaprylate; propylene glycol dicaprate; tridecyl erucate;
  • triisopropyl citrate triisostearyl citrate; glyceryl trilactate; glyceryl trioctanoate; trioctyldodecyl citrate; trioleyl citrate; propylene glycol dioctanoate; neopentyl glycol diheptanoate; diethylene glycol diisononanoate; and polyethylene glycol distearates.
  • esters mentioned above it is preferred to use ethyl, isopropyl, myristyl, cetyl or stearyl palmitate, 2-ethylhexyl palmitate, 2-octyldecyl palmitate, alkyl myristates such as isopropyl, butyl, cetyl or 2-octyldodecyl myristate, hexyl stearate, butyl stearate, isobutyl stearate; dioctyl malate, hexyl laurate, 2-hexyldecyl laurate, isononyl isononanoate or cetyl octanoate.
  • alkyl myristates such as isopropyl, butyl, cetyl or 2-octyldodecyl myristate, hexyl stearate, butyl stearate, isobutyl stearate
  • the oil phase may also comprise, as fatty ester, sugar esters and diesters of C6-C30 and preferably Q2-C22 fatty acids.
  • sugar esters means oxygen-bearing hydrocarbon-based compounds containing several alcohol functions, with or without aldehyde or ketone functions, and which contain at least 4 carbon atoms. These sugars may be monosaccharides,
  • suitable sugars include sucrose (or saccharose), glucose, galactose, ribose, fructose, maltose, mannose, arabinose, xylose and lactose, and derivatives thereof, especially alkyl derivatives, such as methyl derivatives, for instance methylglucose.
  • the sugar esters of fatty acids may be chosen especially from the group comprising the esters or mixtures of esters of sugars described previously and of linear or branched, saturated or unsaturated C6-C30 and preferably Q2-C22 fatty acids. If they are unsaturated, these compounds may comprise one to three conjugated or non-conjugated carbon-carbon double bonds.
  • esters according to this variant may also be chosen from mono-, di-, tri-, tetraesters and polyesters, and mixtures thereof.
  • esters may be chosen, for example, from oleates, laurates, palmitates, myristates, behenates, cocoates, stearates, linoleates, linolenates, caprates and arachidonates, or mixtures thereof such as, especially, oleo-palmitate, oleo-stearate and palmito-stearate mixed esters.
  • monoesters and diesters and especially sucrose, glucose or methylglucose mono- or dioleates, stearates, behenates, oleopalmitates, linoleates, linolenates and oleostearates.
  • Glucate® DO is a methylglucose dioleate.
  • esters or mixtures of esters of sugar and of fatty acid examples include:
  • sucrose palmitostearates formed from 73% monoester and 27% diester and triester, from 61% monoester and 39% diester, triester and tetraester, from 52% monoester and 48% diester, triester and tetraester, from 45% monoester and 55% diester, triester and tetraester, from 39% monoester and 61% diester, triester and tetraester, and sucrose monolaurate;
  • the oil phase may include be at least one fatty acid.
  • Two or more fatty acids may be used.
  • the fatty acids should be in acidic form (i.e., unsalified, to avoid soaps) and may be saturated or unsaturated and contain from 6 to 30 carbon atoms and in particular from 9 to 30 carbon atoms, which is optionally substituted, in particular with one or more hydroxyl groups (in particular 1 to 4). If they are unsaturated, these compounds may comprise one to three conjugated or
  • non-conjugated carbon-carbon double bonds They are more particularly chosen from myristic acid, palmitic acid, stearic acid, behenic acid, oleic acid, linoleic acid, linolenic acid and isostearic acid.
  • the fatty material is not a fatty acid.
  • the oil phase may include at least one fatty alcohol, and two or more fatty alcohols may be used.
  • fatty alcohol here means any saturated or unsaturated, linear or branched C 8 -C 3 o fatty alcohol, which is optionally substituted, in particular with one or more hydroxyl groups (in particular 1 to 4). If they are unsaturated, these compounds may comprise one to three conjugated or non-conjugated carbon-carbon double bonds.
  • fatty alcohols are unsaturated and/or branched.
  • C 12 -C 22 fatty alcohols for example, are used. Mention may be made among these of, isostearyl alcohol, oleyl alcohol, linoleyl alcohol, undecylenyl alcohol, palmitoleyl alcohol, linolenyl alcohol, erucyl alcohol, and mixtures thereof.
  • cetyl alcohol, stearyl alcohol or a mixture thereof (e.g., cetearyl alcohol), as well as myristyl alcohol can be used as a solid fatty material.
  • isostearyl alcohol can be used as a liquid fatty material.
  • the oil phase may include at least one wax.
  • wax means a fatty compound substantially in the form of a solid at room temperature (25°C) under atmospheric pressure (760 rnmHg), and has a melting point generally of 35°C or more.
  • waxy fatty material waxes generally used in cosmetics can be used alone or in combination thereof.
  • the wax may be a fatty alcohol.
  • cetyl alcohol, stearyl alcohol or a mixture thereof (e.g., cetearyl alcohol), as well as myristyl alcohol can be used as the solid fatty material.
  • the wax may be also chosen from carnauba wax, microcrystalline waxes, ozokerites,
  • hydrogenated jojoba oil polyethylene waxes such as the wax sold under the name "Performalene 400 Polyethylene” by the company New Phase Technologies, silicone waxes, for instance poly(C 24 -C2 8 )alkylmethyldimethylsiloxane, such as the product sold under the name "Abil Wax 9810” by the company Goldschmidt, palm butter, the C 2 o-C 40 alkyl stearate sold under the name "Kester Wax K82H” by the company Kester Keunen, stearyl benzoate, shellac wax, and mixtures thereof.
  • polyethylene waxes such as the wax sold under the name "Performalene 400 Polyethylene” by the company New Phase Technologies
  • silicone waxes for instance poly(C 24 -C2 8 )alkylmethyldimethylsiloxane, such as the product sold under the name "Abil Wax 9810” by the company Goldschmidt, palm butter, the C 2 o-C 40 alkyl ste
  • a wax chosen from carnauba wax, candelilla wax, ozokerites, hydrogenated jojoba oil and polyethylene waxes is used.
  • the wax is preferably chosen from candelilla wax and ozokerite, and mixtures thereof.
  • the oil phase may include at least one colorant, but it is preferable that the oil phase be transparent or translucent.
  • the oil phase is free from silicone(s).
  • the term "free from” here means that the oil phase may contain only a small amount of silicone(s), preferably no silicone(s).
  • the amount of silicone(s) may be 5% by weight or less, preferably 3% by weight or less, more preferably 1 % by weight or less of silicone(s). It is particularly preferable that the oil phase contains no silicone(s).
  • the oil phase may include at least one lipophilic compound such as oil-soluble organic or inorganic compounds (e.g., some types of amino acids).
  • the amount of the lipophilic compound is 50% by weight or less relative to the total weight of the oil phase.
  • the amount of oil(s) in the oil phase may range from 50 to 100% by weight, preferably 60 to 100% by weight, and more preferably from 70 to 100% by weight, relative to the total weight of the oil phase.
  • the amount of the (a) oil phase may range from 10 to 80% by weight, preferably from 20 to 70% by weight, and more preferably from 30 to 60% by weight, relative to the total weight of the composition.
  • the cosmetic composition according to the present invention includes at least one alcohol phase including at least one liquid alcohol. Two or more alcohols may be used in combination. Thus, a single type of alcohol or a combination of different type of alcohols may be used.
  • the alcohol phase is in the form of a liquid at ambient temperature such as 25°C under atmospheric pressure (760 mmHg or 10 5 Pa).
  • alcohol here means an alcohol having one, two or more hydroxy groups, and does not encompass a saccharide or a derivative thereof.
  • the derivative of a saccharide includes a sugar alcohol which is obtained by reducing one or more carbonyl groups of a saccharide, as well as a saccharide or a sugar alcohol in which the hydrogen atom or atoms in one or more hydroxy groups thereof has or have been replaced with at least one substituent such as an alkyl group, a hydroxyalkyl group, an alkoxy group, an acylgroup or a carbonyl group.
  • Alcohols used in the present invention are liquid at ambient temperature such as 25 °C under atmospheric pressure (760 irrmHg or 10 5 Pa).
  • the alcohol When the alcohol has one hydroxy group, it is a monoalcohol.
  • the alcohol When the alcohol has two or more hydroxy groups, it is a polyol.
  • the monoalcohol is preferably a C 2 -C 24 monoalcohol, more preferably a C2-Q2 linear or branched monoalcohol, most preferably a C 2 -C 4 linear or branched monoalcohol.
  • Preferred monoalcohols are ethanol and isopropanol.
  • the polyol may be a C 2 -2 4 polyol, preferably a C2.9 polyol, comprising at least 2 hydroxy groups, and preferably 2 to 5 hydroxy groups.
  • the polyol may be a natural or synthetic polyol.
  • the polyol may have a linear, branched or cyclic molecular structure.
  • the polyol may be selected from glycerins and derivatives thereof, and glycols and derivatives thereof.
  • the polyol may be selected from the group consisting of glycerin, diglycerin, polyglycerin, ethyleneglycol, diethyleneglycol, propyleneglycol, dipropyleneglycol,
  • the alcohol phase may optionally include an alkylene oxide derivative represented by the following formula (I):
  • Z denotes a residue obtained by removing fully (or totally) hydroxyl group(s) from a compound having 3 to 9 hydroxyl groups;
  • AO denotes an oxyalkylene group having 3 to 4 carbon atoms
  • EO denotes an oxyethylene group
  • BO denotes an oxyalkylene group having 4 carbon atoms
  • a denotes 3 to 9;
  • 1, m, and n denote the average addition mole numbers of AO, EO and BO, respectively, and 1 ⁇ 1 ⁇ 50, 1 ⁇ m ⁇ 50 and 0.5 ⁇ n ⁇ 5;
  • a weight ratio of AO to EO ranges from 1/5 to 5/1;
  • AO and EO may have been added randomly or in the form of blocks.
  • the aforementioned alkylene oxide derivatives may be a single type thereof, or a mixture of plural types thereof.
  • Z denotes a residue obtained by fully removing hydroxyl groups from a compound having 3 to 9 hydroxyl groups, and a denotes the number of hydroxyl groups of the compound and is 3 to 9.
  • Z denotes a residue obtained by removing hydroxyl group(s) from a compound having 3 to 6 hydroxyl groups, and a satisfies 3 ⁇ a ⁇ 6.
  • the compound having 3 to 9 hydroxyl groups glycerin or trimethylolpropane is preferable, and in particular, glycerin is preferable.
  • a ⁇ 2 poor compatibility with oil components such as fats and oils is exhibited, and blending stability in an oil-based formulation tends to be impaired.
  • 10 ⁇ a stickiness occurs.
  • AO denotes an oxyalkylene group having 3 to 4 carbon atoms.
  • the oxypropylene group and oxybutylene group are preferable, and the oxypropylene group is more preferable.
  • 1 denotes the average addition mole number of AO, and satisfies 1 ⁇ 1 ⁇ 50, and preferably 2 ⁇ 1 ⁇ 20.
  • m denotes the average addition mole number of EO, and satisfies 1 ⁇ m ⁇ 50, and preferably
  • the weight ratio of AO to EO ranges from 1/5 to 5/1, and preferably ranges from 1/4 to 4/1. If AO/EO is below 1/5, stickiness occurs. On the other hand, if AO/EO exceeds 5/1 , the moisturizing sensation is decreased.
  • the order of adding AO and EO is not particularly specified. AO and EO can be added randomly or in the form of blocks. In order to obtain superior effects of preventing skin roughness, AO and EO are preferably added randomly.
  • BO denotes an oxyalkylene group having 4 carbon atoms.
  • an oxybutylene group an oxy-n-butylene group, an oxy-isobutylene group, or an oxy-t-butylene group
  • the oxybutylene group is preferable.
  • n denotes the average addition mole number of BO, and satisfies 0.5 ⁇ n ⁇ 5, preferably 0.8 ⁇ n ⁇ 3, and more preferably 1 ⁇ n ⁇ 3. If n is below 0.5, stickiness occurs. On the other hand, if n exceeds 5, moisturizing effects are decreased.
  • the alkylene oxide derivatives represented by formula (I) can be produced by means of known methods.
  • the alkylene oxide derivatives represented by formula (I) can be obtained by additive-polymerizing ethylene oxide and an alkylene oxide having 3 to 4 carbon atoms to a compound having 3 to 9 hydroxyl groups, and subsequently reacting with an alkylene oxide having 4 carbon atoms.
  • the ethylene oxide and alkylene oxide may be polymerized randomly or in the form of blocks.
  • alkylene oxide derivatives represented by formula (I) preferable examples of the aforementioned alkylene oxide derivatives include, for example, an alkylene oxide derivative (polyoxybutylene polyoxyethylene polyoxypropylene glycerol) represented by formula (II) shown below:
  • Gly denotes a residue obtained by removing hydroxyl groups from glycerin
  • PO denotes an oxypropylene group
  • EO denotes an oxyethylene group
  • s and t denote the average addition mole numbers of PO and EO, respectively, and have a value ranging from 1 to 50;
  • the weight ratio of PO to EO ranges from 1 /5 to 5/1 ;
  • BO denotes an oxyalkylene group having 4 carbon atoms
  • u denotes the average addition mole number of BO, and ranges from 0.5 to 5.
  • the aforementioned alkylene oxide derivative represented by formula (II) can be obtained by adding propylene oxide and ethylene oxide to glycerin, in the ratio of 3 to 150 mole equivalents of each of propylene oxide and ethylene oxide with respect to glycerin, and subsequently, adding the alkylene oxide having 4 carbon atoms in the ratio of 1.5 to 15 mole equivalents thereof with respect to glycerin.
  • the addition reactions are carried out with an alkali catalyst, a phase transfer catalyst, a Lewis acid catalyst, or the like.
  • an alkali catalyst such as potassium hydroxide is preferably employed.
  • alkylene oxide derivatives represented by formula (I) more preferable derivatives are obtained by adding 6 to 10 mol of ethylene oxide and 3 to 7 mol of propylene oxide to glycerin, and subsequently, adding 2 to 4 mol of butylene oxide.
  • a further more preferable derivative is polyoxybutylene polyoxyethylene polyoxypropylene glycerol, which is obtained by adding 8 mol of ethylene oxide and 5 mol of propylene oxide to glycerin, and subsequently, adding 3 mol of butylene oxide, and which has an INCI name of PEG/PPG/polybutylene glycol-8/5/3 glycerin.
  • PEG PPG/polybutylene glycol-8/5/3 glycerin is commercially available under the trade name of WILBRIDE S-753 from NOF Corporation.
  • the alcohol phase may include at least one colorant, but it is preferable that the alcohol phase be transparent or translucent.
  • the alcohol phase may include at least one compound which is soluble in the alcohol phase such as some types of amino acids, nonionic active ingredients such as Vitamin C, and nonionic surfactant with an HLB value of more than 13.0.
  • the amount of the alcohol-soluble compound is 50% by weight or less relative to the total weight of the alcohol phase.
  • the amount of the nonionic surfactant with an HLB value of more than 13.0 is preferably 3% by weight or less, and more preferably 2% by weigh or less, and furthermore preferably 1% by weight or less, relative to the total weight of the alcohol phase.
  • the amount of alcohol(s) in the alcohol phase may range from 50 to 100% by weight, preferably 60 to 100% by weight, and more preferably from 70 to 100% by weight, relative to the total weight of the alcohol phase.
  • the amount of the (b) alcohol phase may range from 5 to 80% by weight, preferably from 8 to 70% by weight, and more preferably from 10 to 60% by weight, relative to the total weight of the composition.
  • the cosmetic composition according to the present invention includes at least one nonionic surfactant phase including at least one specific nonionic surfactant. Two or more specific nonionic surfactants may be used in combination. Thus, a single type of specific nonionic surfactant or a combination of different type of specific nonionic surfactants may be used.
  • the nonionic surfactant phase is in the form of a liquid at ambient temperature such as 25 °C under atmospheric pressure (760 mmHg or 10 5 Pa).
  • the specific nonionic surfactant is selected from esters of polyols with fatty acids with a saturated or unsaturated chain containing for example from 8 to 24 carbon atoms, preferably 12 to 22 carbon atoms, and alkoxylated derivatives thereof with a number of alkyleneoxide of from 10 to 200.
  • the specific nonionic surfactant is selected from alkoxylated derivatives of esters of polyols with fatty acids with a saturated or unsaturated chain containing from 8 to 24 carbon atoms, preferably 12 to 22 carbon atoms, with a number of alkyleneoxide of from 10 to 200, preferably from 10 to 100.
  • nonionic surfactant polyols with fatty acids with a saturated or unsaturated chain containing for example from 8 to 24 carbon atoms, preferably 12 to 22 carbon atoms, and alkoxylated derivatives thereof with a number of alkyleneoxide of from 10 to 200
  • appropriate viscosity can be provide to the cosmetic composition according to the present invention in order to prevent for dripping down, when being used, of the cosmetic composition.
  • the specific nonionic surfactant may be selected from glyceryl esters of a C 8 -C 24 , preferably Ci 2 -C 22 , fatty acid or acids and alkoxylated derivatives thereof with a number of alkyleneoxide of from 10 to 200, preferably from 10 to 100; polyethylene glycol esters of a C 8 -C 24 , preferably C 12 -C 2 2, fatty acid or acids and alkoxylated derivatives thereof with a number of alkyleneoxide of from 10 to 200, preferably from 10 to 100; sorbitol esters of a Cg-C 2 4, preferably Ci 2 -C22, fatty acid or acids and alkoxylated derivatives thereof with a number of alkyleneoxide of from 10 to 200, preferably from 10 to 100; sugar (sucrose, glucose, alkylglycose) esters of a C 8 -C 24 , preferably Ci 2 -C 22 , fatty acid or acids and alkoxylated
  • ethoxylated fatty esters examples include the adducts of ethylene oxide with esters of lauric acid, palmitic acid, stearic acid or behenic acid, and mixtures thereof, especially those containing from 10 to 100 oxyethylene groups, such as PEG-10 to PEG-50 laurate (as the CTFAnames: PEG-10 laurate to PEG-50 laurate); PEG-10 to PEG-50 palmitate (as the CTFAnames: PEG-10 palmitate to PEG-50 palmitate); PEG-10 to PEG-50 stearate (as the CTFAnames: PEG-10 stearate to PEG-50 stearate); PEG-10 to PEG-50 palmitostearate; PEG-10 to PEG-50 behenate (as the CTFAnames: PEG-10 behenate to PEG-50 behenate); polyethylene glycol 100 EO monostearate (CTFAname: PEG-100 stearate); and mixtures thereof.
  • PEG-10 to PEG-50 laurate
  • glyceryl esters of fatty acids glyceryl stearate (glyceryl mono-, di- and/or tristearate) (CTFA name: glyceryl stearate) or glyceryl ricinoleate and mixtures thereof can in particular be cited.
  • polyethoxylated glyceryl stearate glyceryl mono-, di- and/or tristearate
  • PEG-20 glyceryl stearate PEG-20 glyceryl stearate
  • surfactants such as for example the product containing glyceryl stearate and PEG- 100 stearate, marketed under the name ARLACEL 165 by Uniqema, and the product containing glyceryl stearate (glyceryl mono- and distearate) and potassium stearate marketed under the name TEGIN by Goldschmidt (CTFA name: glyceryl stearate SE), can also be used.
  • the sorbitol esters of C8-C24 fatty acids and alkoxylated derivatives thereof can be selected from sorbitan palmitate, sorbitan trioleate and esters of fatty acids and alkoxylated sorbitan containing for example from 20 to 100 EO, such as for example polyethylene sorbitan trioleate (polysorbate 85) or the compounds marketed under the trade names Tween 20 or Tween 60 by Ubiqema.
  • esters of fatty acids and glucose or alkylglucose in particular glucose palmitate, alkylglucose sesquistearates such as methylglucose sesquistearate, alkylglucose palmitates such as
  • methylglucose or ethylglucose palmitate methylglucoside fatty esters and more specifically the diester of methylglucoside and oleic acid
  • CFA name Methyl glucose dioleate
  • CTFA name Methyl glucose dioleate/hydroxystearate
  • CTFA name Methyl glucose dioleate/hydroxystearate
  • CTFA name Methyl glucose isostearate
  • the ester of methylglucoside and lauric acid CFA name: Methyl glucose laurate
  • CTFA name Methyl glucose sesqui-isostearate
  • CTFA name Methyl glucose sesqui-isostearate
  • CTFA name Methyl glucose sesquistearate
  • Glucate SS methylglucoside and stearic acid
  • CTFA name Methyl glucose sesquistearate
  • Glucate SS methylglucoside and stearic acid
  • CTFA name PEG-20 methyl glucose distearate
  • Glucam E-20 distearate the polyethylene glycol ether of the mixture of monoester and diester of methyl-glucose and stearic acid with about 20 moles of ethylene oxide
  • glycerides of alkoxylated plant oils such as mixtures of ethoxylated (200 EO) palm and copra (7 EO) glycerides can also be cited.
  • Co-emulsifiers such as for example fatty alcohols having from 8 to 26 carbon atoms, such as cetyl alcohol, stearyl alcohol and the mixture thereof (cetearyl alcohol), octyl dodecanol, 2-butyloctanol, 2-hexyldecanol, 2-undecylpentadecanol or oleyl alcohol, or fatty acids, can be added to these nonionic surfactants.
  • the nonionic surfactant be selected from the group consisting of PEG-20 methylglucoside sesquistearate, PEG-20 glyceryl tri-isostearate, PG-10 isostearate, and PEG-60 hydrogenated castor oil.
  • the specific nonionic surfactant used in the present invention may be a nonionic surfactant with an HLB of 18.0 or less, such as from 4.0 to 18.0, more preferably from 6.0 to 15.0 and furthermore preferably from 9.0 to 13.0.
  • the HLB is the ratio between the hydrophilic part and the lipophilic part in the molecule. This term HLB is well known to those skilled in the art and is described in "The HLB system. A time-saving guide to emulsifier selection" (published by ICI Americas Inc., 1984).
  • the nonionic surfactant phase may contain at least one additional nonionic surfactant other than the above specific nonionic surfactant used in the present invention.
  • additional nonionic surfactant(s) may be selected from alpha-diols, alkylphenols , these compounds being ethoxylated, propoxylated or glycerolated and having at least one fatty chain comprising, for example, from 8 to 18 carbon atoms, it being possible for the number of ethylene oxide or propylene oxide groups to range from 2 to 9, and for the number of glycerol groups to range from 1 to 30, copolymers of ethylene oxide and/or of propylene oxide; condensates of ethylene oxide and/or of propylene oxide with fatty alcohols; polyethoxylated fatty amides comprising, for example, from 2 to 9 mol of ethylene oxide; polyglycerolated fatty amides comprising, for example, from 1;5 to 5 glycerol groups, such as from 1.5 to
  • the specific nonionic surfactant used in the present invention is soluble in the oil phase and/or the alcohol phase.
  • the amount of the (c) nonionic surfactant phase may range from 0.1 to 50% by weight, preferably from 0.5 to 40% by weight, more preferably from 1 to 30% by weight, and most preferably from 1 to 25% by weight, relative to the total weight of the composition.
  • the cosmetic composition according to the present invention is anhydrous.
  • anhydrous here means that the cosmetic composition according to the present invention may contain only a small amount of water, preferably no water.
  • the amount of water may be 2% by weight or less, preferably 1.5% by weight or less, more preferably 1% by weight or less relative to the total weight of the composition. It is particularly preferable that the cosmetic composition according to the present invention contains no water.
  • the (a) oil phase, the (b) alcohol phase, and the (c) nonionic surfactant phase in the anhydrous cosmetic composition can directly contact to each other.
  • the above three phases may be packaged in a single container.
  • the (a) oil phase, the (b) alcohol phase, and the (c) nonionic surfactant phase in the anhydrous cosmetic composition according to the present invention can be spontaneously separated from each other.
  • at least two of the three phases are visually distinct after coming in a sate of rest. More preferably, the three phases can be separated. This phase separation can visually stimulate the users of the anhydrous cosmetic composition according to the present invention.
  • the (c) nonionic surfactant phase in the anhydrous cosmetic composition according to the present invention can be present between the (a) oil phase and the (b) alcohol phase.
  • composition according to the present invention can be caused by leaving it without any shear force for a certain period of time such as 10 minutes to 24 hours.
  • the anhydrous cosmetic composition according to the present invention can form a homogeneous phase when being mixed by, for example, shaking the composition by hand. It is preferable that the homogeneous phase be in the lamellar form, and viscous such that it does not drip off.
  • the viscosity of the anhydrous cosmetic composition according to the present invention is not particularly limited.
  • the viscosity can be measured at 25 °C with viscosimeters or rheometers preferably with cone-plane geometry.
  • the viscosity of the anhydrous cosmetic composition according to the present invention can range, for example, from 1 to 2000 Pa.s, and preferably from 1 to 1000 Pa.s at 25°C and Is "1 .
  • the anhydrous cosmetic composition according to the present invention may also comprise an effective amount of cosmetic additives such as anionic, cationic or amphoteric surfactants, thickeners, sequestering agents, UV screening agents, preserving agents, vitamins or provitamins, opacifiers, fragrances, plant extracts, humectants, waxes, fillers, colouring materials, antioxydants, proteins, and so on. If any of the (a) oil phase, the (b) alcohol phase, and the (c) nonionic surfactant phase is colored, the anhydrous cosmetic composition according to the present invention may be more visually attractive for users.
  • cosmetic additives such as anionic, cationic or amphoteric surfactants, thickeners, sequestering agents, UV screening agents, preserving agents, vitamins or provitamins, opacifiers, fragrances, plant extracts, humectants, waxes, fillers, colouring materials, antioxydants, proteins, and so on. If any of the (a) oil phase
  • the anhydrous cosmetic composition according to the present invention can be prepared by mixing the above essential or optional components by using a conventional mixing means such as a mixer and a homogenizer.
  • the anhydrous cosmetic composition according to the present invention can be used as cosmetics for skin or hair, such as hair rinse-off or leave on products (e.g., shampoos and conditioners), make-up removers (e.g., cleansing products), make-up products (e.g., foundations), body wash products, and skin moisturizing products.
  • hair rinse-off or leave on products e.g., shampoos and conditioners
  • make-up removers e.g., cleansing products
  • make-up products e.g., foundations
  • body wash products e.g., body wash products, and skin moisturizing products.
  • the anhydrous cosmetic composition according to the present invention is constituted by not only oil(s) but also alcohol(s) and specific nonionic surfactant(s), it can be prepared by using a less amount of oils as compared to conventional oil-based cosmetic products, and therefore, this can reduce the cost to prepare the anhydrous cosmetic composition according to the present invention.
  • the anhydrous cosmetic composition according to the present invention can be used in a cosmetic process for keratin substance comprising the step of applying the anhydrous cosmetic composition according to the present invention to keratin substance.
  • the keratin substance here means a material containing keratin as a main constituent element, and examples thereof include skin, nails, lips, hair and the like.
  • the keratin substance can be in a dry state or in a wet state before application of the cosmetic composition according to the present invention.
  • the application of the cosmetic composition according to the invention to the keratin substance may or may not be followed by rinsing the keratin substance.
  • the cosmetic composition according to the present invention can be left in contact with the keratin substance, for example, from 30 seconds to 30 minutes.
  • the cosmetic process for keratin substance according to the present invention comprise the step of mixing the (a) oil phase, the (b) alcohol phase and the (c) nonionic surfactant phase in the anhydrous cosmetic composition, for example by hand, before the step of applying the anhydrous cosmetic composition to the keratin substance.
  • homogeneous phase is formed. Since the homogeneous phase includes oil(s), alcohol(s) and nonionic surfactant(s) equally, the cosmetic effects provided by these ingredients can be provided uniformly to the keratin substance, which will result in good balance of cosmetic effects provided by each of the phases (a) to (c).
  • the homogeneous phase is not in the form of an O/W emulsion, oil and/or alcohol (they are capable of forming a layer on keratin substance which can inhibit the evaporation of water from the keratin substance, while they can solubilize hydrophobic or hydrophilic substances used in, for example, make-up cosmetics) can directly contact the keratin substance, and therefore, the anhydrous cosmetic composition according to the present invention can provide superior moisturizing and/or cleansing effects. Furthermore, due to the presence of the nonionic surfactant(s), the anhydrous cosmetic
  • composition according to the present invention can be easily rinsed off.
  • the anhydrous cosmetic composition according to the present invention when used with water, it can easily form an emulsion, and can be smoothly removed from the keratin substance.
  • the alcohol can also be removed easily, when the anhydrous cosmetic composition according to the present invention is used with water, because of its hydrophilic nature.
  • nonionic surfactants are less irritative, and therefore, the anhydrous cosmetic composition according to the present invention can provide good feeling to use.
  • anhydrous cosmetic compositions were prepared by mixing the ingredients shown in Table 1. Each of the mixture was filled into a transparent glass tube container. After vigorous shaking by hand, the anhydrous cosmetic compositions according to Examples 1 and 2 were in the form of a homogeneous phase. About 10 minutes after the shaking, it was observed that each of the anhydrous cosmetic compositions separated into 3 phases.
  • An anhydrous cosmetic composition was prepared by mixing the ingredients shown in Table 1. The mixture was filled into a transparent glass tube container. After vigorous shaking by hand, the anhydrous cosmetic composition according to Comparative Example 1 was in the form of a homogeneous phase. About 10 minutes after the shaking, it was observed that the anhydrous cosmetic composition was separated into 3 phases.
  • compositions according to Examples 1 and 2, as well as Comparative Example 1 were evaluated as follows: They were applied on the make-up on the face, at room temperature (25 °C); then, they were rinsed with water stream.
  • the quantity of the make-up (liquid foundation) applied was 0.01 g/cm .
  • the cosmetic composition was applied with finger on the area of 2x2cm .
  • the quantity of the cosmetic composition was 0.2 g.
  • the rinsing was performed under tap water.
  • the compositions according to Examples 1 and 2 showed very good removability of the make-up on the skin, and very good rinsability. Furthermore, there was no dripping down when applying the composition according to Examples 1 and 2 on the face, while the composition according to Comparative Example 1 showed dripping down. [Examples 3 to 9]
  • the following haircare compositions were prepared by mixing the ingredients shown in Table 2 (% by weight).
  • compositions according to Examples 3 to 9 were evaluated as follows: They were applied on the tip and middle of wet hair just after being subjected to shampooing, as a rinse-off conditioner, at room temperature (25°C), followed by soft massaging the hair; then, they were rinsed with water stream. After the rinse step, the hair was dried with a drier or with a towel in the atmosphere at ambient temperature. The feeling to touch the hair was evaluated. During the rinse step, the compositions according to Examples 4, 5 and 6 was in the appearance of milk. In comparison with the use of pure oil on the same conditions, the feeling to touch of the hair treated with the compositions according to Examples 3 to 9 was not oily but moisture feel. [Examples 10 to 13]
  • the following skincare compositions were prepared by mixing the ingredients shown in Table 3 (% by weight).
  • compositions according to Examples 10 to 13 were evaluated as follows: They were applied on the make-up on the face, at room temperature (25°C); then, they were rinsed with water stream.
  • the quantity of the make-up (liquid foundation) applied was 0.01 g/cm .
  • the cosmetic composition was applied with finger on the area of 2x2cm .
  • the quantity of the cosmetic composition was 0.2 g.
  • the rinsing was performed under tap water.
  • the compositions according to Examples 10 to 13 showed good removability of the make-up on the skin, and good rinsability. Furthermore, there was no dripping down when applying the composition according to Examples 10 to 13 on the face. The above evaluations were performed on 12 women.
  • compositions according to Examples 10 to 13 were easy to homogenize and the resulting texture was gelified and translucent which makes the application of the compositions to the skin easy (no dripping). Further, waterproof mascara and foundation were easily removed, and rinsing was good. Furthermore, there was no eye discomfort.

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Abstract

La présente invention concerne une composition cosmétique anhydre comprenant : (a) au moins une phase huileuse comprenant au moins une huile ; (b) au moins une phase alcoolique comprenant au moins un alcool ; et (c) au moins une phase de tensioactif non ionique comprenant au moins un tensioactif non ionique, le tensioactif non ionique étant choisi parmi des esters de polyols avec des acides gras dotés d'une chaîne saturée ou non saturée contenant par exemple de 8 à 24 atomes de carbone, de préférence de 12 à 22 atomes de carbone, et leurs dérivés alcoxylés avec un certain nombre d'oxydes d'alkylène allant de 10 à 200. La composition cosmétique anhydre selon la présente invention peut offrir un aspect multiphasique et peut stimuler visuellement les utilisateurs de la composition cosmétique tout en maintenant de bons effets cosmétiques.
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CN111035583A (zh) * 2019-12-23 2020-04-21 广州市拉凯尔干细胞研究所 一种改善真表皮连接层的护肤品组合物
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WO2016202268A1 (fr) * 2015-06-18 2016-12-22 Rhodia Operations Composition d'émulsion présentant une teneur élevée en huile
US10744073B2 (en) 2016-03-01 2020-08-18 L'oreal Moldable solid cleansing compositions
IT201900006334A1 (it) * 2019-04-24 2020-10-24 Angela Lagana S R L Prodotto, in particolare un prodotto cosmetico, per il trattamento esterno o superficiale del corpo
WO2020217210A1 (fr) * 2019-04-24 2020-10-29 Angela Lagana' Srl Produit, en particulier produit cosmétique, pour le traitement externe ou de surface du corps
CN111035583A (zh) * 2019-12-23 2020-04-21 广州市拉凯尔干细胞研究所 一种改善真表皮连接层的护肤品组合物
US11357714B2 (en) 2020-07-21 2022-06-14 Chembeau LLC Diester cosmetic formulations and uses thereof
US11491092B2 (en) 2020-07-21 2022-11-08 Chembeau LLC Hair treatment formulations and uses thereof
US11801211B2 (en) 2020-07-21 2023-10-31 Chembeau LLC Hair treatment formulations and uses thereof
WO2022131141A1 (fr) 2020-12-14 2022-06-23 L'oreal Composition multiphase comprenant un alpha-hydroxyacide
FR3118872A1 (fr) 2021-01-15 2022-07-22 L'oreal Composition multiphasique comprenant un alpha-hydroxyacide

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