WO2023044666A1 - Composition for conditioning or caring for keratin materials - Google Patents

Composition for conditioning or caring for keratin materials Download PDF

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Publication number
WO2023044666A1
WO2023044666A1 PCT/CN2021/119901 CN2021119901W WO2023044666A1 WO 2023044666 A1 WO2023044666 A1 WO 2023044666A1 CN 2021119901 W CN2021119901 W CN 2021119901W WO 2023044666 A1 WO2023044666 A1 WO 2023044666A1
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composition
oil
surfactant
composition according
combination
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PCT/CN2021/119901
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English (en)
French (fr)
Inventor
Ya HU
Qingsheng Tao
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L'oreal
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Priority to PCT/CN2021/119901 priority Critical patent/WO2023044666A1/en
Priority to CN202180102673.6A priority patent/CN117979945A/zh
Priority to FR2111174A priority patent/FR3127132B1/fr
Publication of WO2023044666A1 publication Critical patent/WO2023044666A1/en

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    • 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
    • A61K8/0291—Micelles
    • 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
    • A61K8/04—Dispersions; Emulsions
    • A61K8/06—Emulsions
    • 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
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
    • A61K8/41—Amines
    • A61K8/416—Quaternary ammonium compounds
    • 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
    • A61K8/92—Oils, fats or waxes; Derivatives thereof, e.g. hydrogenation products thereof
    • 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
    • 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
    • A61K2800/26—Optical properties
    • A61K2800/262—Transparent; Translucent
    • 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 a composition for conditioning or caring for keratin materials, in particular human keratin materials such as the skin and the hair.
  • the present invention also relates to a cosmetic process for conditioning or caring for keratin materials.
  • the hair is generally damaged and weakened by the action of external atmospheric agents such as light, weather, and/or the action of mechanical or chemical treatments such as brushing, combing, dyeing, bleaching, permanent and/or straightening.
  • lipophilic active ingredients available for conditioning the hair.
  • hair oil products comprising lipophilic active ingredients.
  • WO 2000074644A1 discloses a composition containing at least one organic phospholipid capable of forming bilayers in aqueous solution; at least one amphoteric surfactant; at least one nonionic surfactant presents in an amount by weight equal to or greater than the amount of the phospholipid; at least one suspending agent present in an amount effective for maintaining a stable composition; and a lipophilic ingredient.
  • EP0966955A1 discloses a cosmetic composition for treating keratin materials, comprising at least one polyorganosiloxane and an acrylic terpolymer in an aqueous medium.
  • the terpolymer comprises: (1) a carboxylic acid (A) with alpha, beta-monoethylenic unsaturation (20-70, preferably 25-55 wt. %) ; (2) a monomer (B) with non-surfactant monoethylenic unsaturation other than (A) (20-80 wt. %, preferably 30-65 wt.
  • non-ionic urethane monomer (C) prepared by reacting monohydric non-ionic surfactant with a monoisocyanate with monoethylenic unsaturation (0.5-60 wt. %, preferably 10-50 wt. %) .
  • compositions for conditioning the hair or caring for the skin which has a transparent appearance and is stable over time, and optionally comprises an organic solvent soluble active ingredient for conditioning the hair or caring for the skin.
  • An object of the present invention is thus to develop compositions for conditioning or caring for keratin materials, in particular human keratin materials such as the skin and the hair, which has a transparent appearance and is stable over time, and optionally comprises an organic solvent soluble active ingredient for conditioning the hair or caring for the skin.
  • the present invention provides a transparent anhydrous composition for conditioning or caring for keratin materials comprising:
  • both the nonionic surfactant and the ionic surfactant are lipophilic.
  • the present invention provides a cosmetic process for conditioning or caring for keratin materials comprising applying the composition as described above onto the keratin fibres.
  • the inventors have found that there are reverse micelles formed in the composition according to the present invention so that the composition has a transparent appearance and is thermodynamically stable over time, and the composition is effective in conditioning or caring for keratin materials.
  • Fig. 1 shows the multimodal size distribution of leave-on oil of invention example 1.
  • Fig. 2 shows the multimodal size distribution of leave-on oil of invention example 2.
  • Fig. 3 shows the multimodal size distribution of leave-on oil of invention example 3.
  • Fig. 4 shows the multimodal size distribution of leave-on oil of invention example 4.
  • Fig. 5 shows the multimodal size distribution of leave-on oil of invention example 5.
  • Fig. 6 shows the multimodal size distribution of leave-on oil of invention example 6.
  • anhydrous it means that no water is added on purpose and the water content of the composition is less than 0.5 wt. %, particularly less than 0.1 wt. %, relative to the total weight of the composition. In particular, there is no water in the composition.
  • keratin materials includes human keratin materials such as the hair and the skin.
  • reverse micelles has the following definition: surfactants are dissolved in non-polar organic solvents; when their concentration exceeds the critical micelle concentration (CMC) , the micelles formed in the organic solvent, which are called reverse micelles.
  • CMC critical micelle concentration
  • the non-polar groups of the surfactant are externally in contact with non-polar organic solvents, while the polar groups are arranged inside to form a polar core. This polar core has the ability to dissolve polar substances.
  • Reverse micelle is a nano-scale aggregate, which is a transparent and thermodynamically stable W/O system.
  • lipophilic means a substance or material can be dissolved or dispersed in an oily phase at 25°C in order to obtain a macroscopically homogeneous phase.
  • a transparent anhydrous composition for conditioning or caring for keratin materials comprises:
  • a surfactant combination comprising at least one nonionic surfactant and at least one ionic surfactant
  • both the nonionic surfactant and the ionic surfactant are lipophilic.
  • the composition comprises a continuous oily phase comprising at least one oil.
  • oil means a fatty compound or substance which is in the form of a liquid or a paste (non-solid) at room temperature (25°C) under atmospheric pressure (760 mmHg) .
  • oils (s) those generally used in cosmetics can be used alone or in combination thereof. These oil (s) may be volatile or non-volatile, preferably non-volatile.
  • the oil may be a non-polar oil such as hydrocarbons, silicones, or the like; a polar oil such as esters, fatty alcohols and ethers; or a combination thereof.
  • the oil may be oils of plant or animal origin and synthetic oils.
  • plant oils examples include, for example, linseed oil, camellia oil, macadamia nut oil, corn oil, mink oil, olive oil, avocado oil, sasanqua oil, castor oil, safflower oil, jojoba oil, sunflower oil, almond oil, rapeseed oil, sesame oil, soybean oil, peanut oil, and a combination thereof.
  • alkane oils such as isododecane and isohexadecane
  • ester oils such as isododecane and isohexadecane
  • ether oils such as triglycerides
  • the ester oils are preferably liquid esters of saturated or unsaturated, linear or branched C 1 -C 26 aliphatic monoacids or polyacids and of saturated or unsaturated, linear or branched C 1 -C 26 aliphatic monoalcohols or polyalcohols, the total number of carbon atoms of the esters being greater than or equal to 10.
  • esters of monoalcohols Preferably, for the esters of monoalcohols, at least one from among the alcohol and the acid, from which the esters of the present invention are derived, is branched.
  • ethyl palmitate ethyl hexyl palmitate
  • isopropyl palmitate dicaprylyl carbonate
  • alkyl myristates such as isopropyl myristate or ethyl myristate
  • isocetyl stearate 2-ethylhexyl isononanoate
  • isononyl isononanoate isodecyl neopentanoate and isostearyl neopentanoate.
  • esters of C 4 -C 22 dicarboxylic or tricarboxylic acids and of C 1 -C 22 alcohols, and esters of monocarboxylic, dicarboxylic or tricarboxylic acids and of non-sugar C 4 -C 26 dihydroxy, trihydroxy, tetrahydroxy or pentahydroxy alcohols may also be used.
  • sugar esters and diesters of C 6 -C 30 and preferably C 12 -C 22 fatty acids.
  • sucrose means oxygen-bearing hydrocarbon-based compounds containing several alcohol functions, with or without aldehyde or ketone functions, and which comprise at least 4 carbon atoms. These sugars may be monosaccharides, oligosaccharides or polysaccharides.
  • suitable sugars include sucrose (or saccharose) , glucose, galactose, ribose, fucose, maltose, fructose, 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 selected especially from the group comprising the esters or mixtures of esters of sugars described previously and of linear or branched, saturated or unsaturated C 6 -C 30 and preferably C 12 -C 22 fatty acids. Ifthey are unsaturated, these compounds may have one to three conjugated or non-conjugated carbon-carbon double bonds.
  • esters according to this variant may also be selected from monoesters, diesters, triesters, tetraesters and polyesters, and a combination thereof.
  • esters may be, for example, oleates, laurates, palmitates, myristates, behenates, cocoates, stearates, linoleates, linolenates, caprates and arachidonates, or a combination thereof such as, especially, oleopalmitate, oleostearate and palmitostearate mixed esters, as well as pentaerythrityl tetraethyl hexanoate.
  • monoesters and diesters and especially sucrose, glucose or methylglucose monooleates or dioleates, stearates, behenates, oleopalmitates, linoleates, linolenates and oleostearates.
  • ester oils mention may be made of, for example, diisopropyl adipate, dioctyl adipate, 2-ethylhexyl hexanoate, ethyl laurate, cetyl octanoate, octyldodecyl octanoate, isodecyl neopentanoate, myristyl propionate, 2-ethylhexyl 2-ethylhexanoate, 2-ethylhexyl octanoate, 2-ethylhexyl caprylate/caprate, methyl palmitate, ethyl palmitate, isopropyl palmitate, dicaprylyl carbonate, isopropyl lauroyl sarcosinate, isononyl isononanoate, ethylhexyl palmitate, isohexyl laurate, hex
  • artificial triglycerides mention may be made of, for example, caprylic/capric triglyceride, glyceryl trimyristate, glyceryl tripalmitate, glyceryl trilinolenate, glyceryl trilaurate, glyceryl tricaprate, glyceryl tricaprylate, and glyceryl tri (caprate/caprylate/linolenate) .
  • the ether hydrocarbon-based oil also known as an ether oil, may be volatile or non-volatile and is preferably non-volatile.
  • An ether hydrocarbon-based oil is an oil of formula R 1 OR 2 in which R 1 and R 2 independently denote a linear, branched or cyclic C 4 -C 24 alkyl group, preferably a C 6 -C 18 alkyl group, and preferably a C 8 -C 12 alkyl group. It may be preferable for R 1 and R 2 to be identical.
  • Linear alkyl groups that may be mentioned include butyl group, pentyl group, hexyl group, heptyl group, octyl group, nonyl group, decyl group, undecyl group, dodecyl group, tridecyl group, tetradecyl group, pentadecyl group, hexadecyl group, heptadecyl group, octadecyl group, nonadecyl group, eicosyl group, behenyl group, docosyl group, tricosyl group and tetracosyl group.
  • Branched alkyl groups that may be mentioned include 1-methylpropyl group, 2-methylpropyl group, t-butyl group, 1, 1-dimethylpropyl group, 3-methylhexyl group, 5-methylhexyl group, ethylhexyl group, 2-ethylhexyl group, 5-methyloctyl group, 1 -ethylhexyl group, 1-butylpentyl group, 2-butyloctyl group, isotridecyl group, 2-pentylnonyl group, 2-hexyldecyl group, isostearyl group, 2-heptylundecyl group, 2-octyldodecyl group, 1, 3-dimethylbutyl group, l- (l-methylethyl) -2-methylpropyl group, 1, 1, 3, 3-tetramethylbutyl group, 3, 5, 5-trimethylhexyl group, l- (2-methylpropyl) -3
  • Cyclic alkyl groups that may be mentioned include cyclohexyl group, 3-methylcyclohexyl group and 3, 3, 5-trimethylcyclohexyl group.
  • the ether oil is chosen from dicaprylyl ether, dicapryl ether, dilauryl ether, diisostearyl ether, dioctyl ether, nonyl phenyl ether, dodecyl dimethylbutyl ether, cetyl dimethylbutyl ether, cetyl isobutyl ether, and a combination thereof.
  • dicaprylyl ether is chosen from dicaprylyl ether, dicapryl ether, dilauryl ether, diisostearyl ether, dioctyl ether, and a combination thereof.
  • Dicaprylyl ether is most particularly suitable for use.
  • silicone oils mention may be made of, for example, linear organopolysiloxanes such as dimethylpolysiloxane, methylphenylpolysiloxane, methylhydrogenpolysiloxane, and the like; cyclic organopolysiloxanes such as cyclohexasiloxane, octamethylcyclotetrasiloxane, decamethylcyclopentasiloxane, dodecamethylcyclohexasiloxane, and the like; and a combination thereof.
  • linear organopolysiloxanes such as dimethylpolysiloxane, methylphenylpolysiloxane, methylhydrogenpolysiloxane, and the like
  • cyclic organopolysiloxanes such as cyclohexasiloxane, octamethylcyclotetrasiloxane, decamethylcyclopentasiloxane, dodeca
  • silicone oil is selected from liquid polydialkylsiloxanes, especially liquid polydimethylsiloxanes (PDMS) and liquid polyorganosiloxanes comprising at least one aryl group.
  • PDMS liquid polydimethylsiloxanes
  • silicone oils may also be organomodified.
  • organomodified silicones that can be used in accordance with the present invention are silicone oils as defined above and comprise in their structure one or more organofunctional groups attached via a hydrocarbon-based group.
  • Organopolysiloxanes are defined in greater detail in Walter Noll’s Chemistry and Technology of Silicones (1968) , Academic Press. They may be volatile or non-volatile.
  • the silicones are more particularly selected from those having a boiling point of between 60°C and 260°C, and even more particularly from:
  • cyclic polydialkylsiloxanes comprising from 3 to 7 and preferably 4 to 5 silicon atoms.
  • cyclic polydialkylsiloxanes comprising from 3 to 7 and preferably 4 to 5 silicon atoms.
  • These are, for example, octamethylcyclotetrasiloxane sold in particular under the name Volatile 7207 by Union Carbide or 70045 V2 by Rhodia, decamethylcyclopentasiloxane sold under the name Volatile 7158 by Union Carbide, 70045 V5 by Rhodia, and dodecamethylcyclopentasiloxane sold under the name Silsoft 1217 by Momentive Performance Materials, and a combination thereof. Mention may also be made of cyclocopolymers of the type such as dimethylsiloxane/methylalkylsiloxane, such as Silicone FZ 3109 sold by the company Union Carbide, of formula:
  • Non-volatile polydialkylsiloxanes may also be used. These non-volatile silicones are more particularly selected from polydialkylsiloxanes, among which mention may be made mainly of polydimethylsiloxanes containing trimethylsilyl end groups.
  • oils of the 47 and 70 047 series or the oils sold by Rhodia for instance the oil 70 047 V 500 000;
  • oils of the 200 series from the company Dow Corning such as DC200 with a viscosity of 60 000 mm 2 /s;
  • CTFA dimethiconol
  • silicones containing aryl groups are polydiarylsiloxanes, especially polydiphenylsiloxanes and polyalkylarylsiloxanes. Examples that may be mentioned include the products sold under the following names:
  • oils of the SF series from General Electric such as SF 1023, SF 1154, SF 1250 and SF 1265.
  • the organomodified liquid silicones may especially contain polyethyleneoxy and/or polypropyleneoxy groups. Mention may thus be made of the silicone KF-6017 proposed by Shin-Etsu, and the oils L722 and L77 from the company Union Carbide.
  • Hydrocarbon oils may be selected from:
  • hydrocarbon oils As preferable examples of hydrocarbon oils, mention may be made of, for example, linear or branched hydrocarbons such as isohexadecane, isododecane, squalane, mineral oil (e.g., liquid paraffin) , paraffin, vaseline or petrolatum, naphthalenes, and the like; hydrogenated polyisobutene, isoeicosan, and decene/butene copolymer; and a combination thereof.
  • linear or branched hydrocarbons such as isohexadecane, isododecane, squalane, mineral oil (e.g., liquid paraffin) , paraffin, vaseline or petrolatum, naphthalenes, and the like; hydrogenated polyisobutene, isoeicosan, and decene/butene copolymer; and a combination thereof.
  • the oil is selected from branched alkane oils containing from 8 to 20 carbon atoms and better still from 10 to 16 carbon atoms such as isododecane, triglycerides such as caprylic/capric triglyceride, ether hydrocarbon-based oils having a C 8 -C 12 alkyl group such as dicaprylyl ether, polydimethylsiloxanes optionally containing dimethylsilanol end groups such as dimethicones, dimethiconols, and a combination thereof.
  • branched alkane oils containing from 8 to 20 carbon atoms and better still from 10 to 16 carbon atoms such as isododecane
  • triglycerides such as caprylic/capric triglyceride
  • ether hydrocarbon-based oils having a C 8 -C 12 alkyl group such as dicaprylyl ether
  • polydimethylsiloxanes optionally containing dimethylsilanol end groups
  • the oil is selected from isododecane, dicaprylyl ether, caprylic/capric triglyceride, dimethicones, dimethiconols, and a combination thereof.
  • the oil is present in amount ranging from 80 wt. %to 98.5 wt. %, preferably from 85 wt. %to 97.5 wt. %, more preferably from 88 wt. %to 94 wt. %, relative to the total weight of the composition.
  • the composition comprises a surfactant combination comprising at least one nonionic surfactant and at least one ionic surfactant.
  • the composition according to the present invention comprises at least one nonionic surfactant and at least one cationic surfactant, or comprises at least one nonionic surfactant and at least one anionic surfactant.
  • the composition according to the present invention comprises at least one nonionic surfactant and at least one cationic surfactant, or comprises at least one nonionic surfactant and at least one anionic surfactant, as the only surfactants.
  • the organic solvent comprised in the dispersed aqueous phases is relatively higher, and is sufficient to carry an effective amount of the organic solvent soluble active ingredient.
  • the surfactant combination of the present invention achieves synergistic effect.
  • the term “synergistic effect” means the amount of the organic solvent comprised in the dispersed aqueous phases from the action of the surfactants of the present invention is higher than the sum of the amounts of the organic solvent comprised in the dispersed aqueous phases from the actions of each single surfactant comprised in said surfactant combination.
  • the surfactant combination is present in an amount ranging from about 0.1 wt. %to about 20 wt. %, preferably from about 0.5 wt. %to about 10 wt. %, or from about 1 wt. %to about 5 wt. %, relative to the total weight of the composition.
  • ionic surfactant means a surfactant bearing at least one anion or cation in the molecule, and non-limiting examples that can be mentioned are anionic surfactant, cationic surfactant, amphoteric surfactant, and zwitterionic surfactant.
  • the ionic surfactant according to the present invention is preferably selected from anionic surfactants, cationic surfactants and a combination thereof.
  • the anionic surfactant and the cationic surfactant are not comprised in the composition of the present invention simultaneously, and even if they are comprised simultaneously, the amount of one of them is significantly lower or higher than the other one to avoid undesired interactions.
  • the ionic surfactant according to the present invention is lipophilic.
  • anionic surfactants As anionic surfactants, mention can be made of the anionic surfactant having at least one C 6 -C 22 alkyl chain, e.g. one or two C 6 -C 22 alkyl chains, and preferably two C 6 -C 22 alkyl chains.
  • the anionic surfactant is selected from alkyl sulfosuccinates, especially dialkyl sulfosuccinates in which the alkyl radicals have 6 to 22 carbon atoms, preferably 6 to 12 carbon atoms.
  • Different or identical alkyl radicals can be present in one molecule of dialkyl sulfosuccinates, with identical being preferred.
  • the alkyl radicals can be linear, branched or cyclic, saturated or unsaturated, and substituted or unsubstituted.
  • dialkyl sulfosuccinate is selected from dialkyl sulfosuccinates in which each alkyl has 6 to 22 carbon atoms and the counterion to the sulfonic acid group is selected from alkali metal cations and ammonium ions.
  • alkyl sulfosuccinates include diethylhexyl sodium sulfosuccinate, dinonyl sodium sulfosuccinate, diisononyl sodium sulfosuccinate, dioctyl sodium sulfosuccinate, diheptyl sodium sulfosuccinate, dihexyl sodium sulfosuccinate, dicapryl sodium sulfosuccinate, didecyl sodium sulfosuccinate, diundecyl sodium sulfosuccinate, dilauryl sodium sulfosuccinate, dicocoyl sodium sulfosuccinate, ditridecyl sodium sulfosuccinate, dipropylheptyl sodium sulfosuccinate, dicyclohexyl sodium sulfosuccinate, ammonium diethylhexyl sulfos
  • anionic surfactant examples include 1, 3-dioctyl glyceryl ether hydroxylpropyl sulfonates, 1, 3-didecyl glyceryl ether hydroxylpropyl sulfonates, 1, 3-didodecyl glyceryl ether hydroxylpropyl sulfonates, sodium distearyl phosphate, sodium dioleyl phosphate, 1, 2-dioleoyl-sn-glycero-3-phosphate (sodium salt) , sodium dilauramidoglutamide lysine, and ethylene bis (sodium N-dodecanoyl-asparatate) , etc.
  • the anionic surfactant is selected from dialkyl sulfosuccinates in which each alkyl has 6 to 22 carbon atoms, preferably 6 to 12 carbon atoms and the two alkyls are the same.
  • the anionic surfactant is diethylhexyl sodium sulfosuccinate.
  • fatty quaternary ammonium compounds As cationic surfactants, mention can be made of fatty quaternary ammonium compounds, and preferably, the fatty quaternary ammonium compounds having at least one C 6 -C 22 alkyl chain, e.g. one, two or three C 6 -C 22 alkyl chains, with two C 6 -C 22 alkyl chains being preferred.
  • Different or identical alkyl radicals can be present in one molecule of the fatty quaternary ammonium compounds having two or three C 6 -C 22 alkyl chains, with identical being preferred.
  • the alkyl radicals can be linear, branched or cyclic, saturated or unsaturated, and substituted or unsubstituted, and preferably the linear and saturated alkyl radicals.
  • the cationic surfactant is selected from alkyltrimonium, dialkyldimonium, trialkylmonium, and a combination thereof, with each alkyl containing from 6 to 22 carbon atoms, and preferably 12 to 22 carbon atoms.
  • the anion of the quaternary ammonium compound can be a common ion such as halide including chloride and bromide, ethosulfate, methosulfate, acetate, lactate, nitrate, phosphate, tosylate, and a combination thereof.
  • the anion of the quaternary ammonium compound is selected from chloride, methosulfate, and bromide, and especially chloride.
  • Non-limiting examples of the fatty quaternary ammonium compounds include cetrimonium chloride, stearimonium chloride, behentrimonium chloride, cetrimonium methosulfate, behentrimonium methosulfate, arachidtrimonium chloride, distearyldimonium chloride, dicetyldimonium chloride, tricetylmonium chloride, cetrimonium bromide, laurtrimonium chloride, myrtrimonium bromide, oleyltrimonium chloride, dimethyldidodecylammonium bromide, dibehenyldimonium chloride, dioleyldimethylammonium chloride, tristearylmonium chloride, dilauryldimonium chloride, cocotrimonium chloride, cethethyldimonium bromide, stearyl octyl dimonium methosulfate, 1, 2-dioleoyl-3-trimethylam
  • the cationic surfactant is selected from dialkyldimonium halides, with each alkyl containing from 6 to 22 carbon atoms, and preferably 12 to 22 carbon atoms, and the two alkyls are the same.
  • the cationic surfactant is dicetyldimonium chloride.
  • the ionic surfactant is present in an amount ranging from 0.01 wt. %to 5 wt. %, preferably from 0.1 wt. %to 2 wt. %, more preferably from 0.1 wt. %to 1 wt. %, relative to the total weight of the composition.
  • the nonionic surfactant according to the present invention is lipophilic.
  • nonionic surfactants mention can be made of the nonionic surfactant having at least one C 6 -C 22 alkyl chain, e.g. one, two or three C 6 -C 22 alkyl chains, and preferably the nonionic surfactant further has an HLB value ranging from about 0 to about 10.
  • ethoxylated fatty esters examples include the adducts of ethylene oxide with esters of lauric acid, palmitic acid, stearic acid or behenic acid, and a combination thereof, especially those containing from 9 to 100 oxyethylene groups, such as ethylene glycol dilaurate, ethylene glycol distearate, PEG-3 distearate, PEG-8 distearate, PEG-12 distearate, PEG-100 distearate, PEG-150 distearate, PEG-2 dilaurate, PEG-4 dilaurate, PEG-8 dilaurate, ethylene glycol dioleate, PEG-3 dioleate, PEG-4 dioleate, etc.
  • glyceryl esters of fatty acids glyceryl stearate (glyceryl di-and/or tristearate) such as glyceryl 1, 3-distearate, glycerol dioleate, glyceryl dilaurate, glyceryl 1, 3-dipalmitate and a combination thereof can in particular be cited.
  • glyceryl di-and/or tristearate such as glyceryl 1, 3-distearate, glycerol dioleate, glyceryl dilaurate, glyceryl 1, 3-dipalmitate and a combination thereof can in particular be cited.
  • the polyglycerol moiety may be derived from 2 to 10 glycerols, preferably 2 to 8 glycerols, or 2 to 6 glycerols, and/or the fatty acid may be C 6 -C 22 fatty acid, and preferably C 12 -C 22 fatty acid.
  • the polyglycerol esters of fatty acids may be selected from the mono-, di-, tri-or sesqui-esters of a linear or branched, saturated or unsaturated fatty acid, such as lauric acid, oleic acid, stearic acid, isostearic acid, capric acid, caprylic acid, palmitic acid, and myristic acid.
  • the polyglycerol esters of fatty acids may be selected from polyglyceryl mono-, di-, tri-or sesqui-caprylate comprising from 2 to 10 glycerol units, polyglyceryl mono-, di-, tri-or sesqui-caprate comprising from 2 to 10 glycerol units, polyglyceryl mono-, di-, tri-or sesqui-laurate comprising from 2 to 10 glycerol units, polyglyceryl mono-, di-, tri-or sesqui-myristate comprising from 2 to 10 glycerol units, polyglyceryl mono-, di-, tri-or sesqui-palmitate comprising from 2 to 10 glycerol units, polyglyceryl mono-, di-, tri-or sesqui-stearate comprising from 2 to 10 glycerol units, polyglyceryl mono-, di-, tri-or sesqui-isostearate comprising from 2 to 10 glycerol units, polyglyceryl mono
  • the sorbitol esters of C 6 -C 22 fatty acids and alkoxylated derivatives thereof can be selected from sorbitan tristearate, sorbitan trioleate and esters of fatty acids such as span 65,span 85 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 Croda.
  • 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 (methyl glucose dioleate) , the mixed ester of methylglucoside and the mixture oleic acid/hydroxystearic acid (methyl glucose dioleate/hydroxystearate) , the ester of methylglucoside and isostearic acid (methyl glucose isostearate) , the ester of methylglucoside and lauric acid (Methyl glucose laurate) , the mixture of monoester and diester of methylglucoside and isostearic acid (Methyl glucose sesqui-isostearate) , the mixture of monoester and mono
  • ethoxylated ethers of fatty acids and glucose or alkylglucose ethoxylated ethers of fatty acids and methylglucose, and in particular the polyethylene glycol ether of the diester of methylglucose and stearic acid with about 20 moles of ethylene oxide (PEG-20 methyl glucose distearate) such as the product marketed under the name GLUCAM E-20 DISTEARATE by Lubrizol, the polyethylene glycol ether of the mixture of monoester and diester of methyl-glucose and stearic acid with about 20 moles of ethylene oxide (PEG-20 methyl glucose sesquistearate) and in particular the product marketed under the name GLUCAMATE SSE-20 by Lubrizol, and a combination thereof, can for example be cited.
  • PEG-20 methyl glucose distearate the polyethylene glycol ether of the mixture of monoester and diester of methyl-glucose and stearic acid with about 20 moles of ethylene
  • sucrose esters sucrose dilaurate, sucrose trilaurate, sucrose dioleate, sucrose trioleate, sucrose tristearate can be cited.
  • the nonionic surfactant is selected from polyglycerol esters of fatty acids; especially polyglyceryl mono-, di-or tri-oleate comprising from 2 to 6 glycerol units, polyglyceryl mono-, di-or tri-isostearate comprising from 2 to 6 glycerol units, and a combination thereof.
  • the nonionic surfactant is selected from polyglyceryl-6 dioleate, polyglyceryl-2 oleate, polyglyceryl-2 triisostearate, and a combination thereof.
  • the nonionic surfactant is present in an amount ranging from 0.01 wt.%to 20 wt. %, preferably from 0.1 wt. %to 10 wt. %, more preferably from 0.1 wt. %to 5 wt. %, most preferably from 0.5 wt. %to 4 wt. %, relative to the total weight of the composition.
  • the composition comprises dispersed phases comprising an organic solvent.
  • the dispersed phase of the composition according to the present invention comprises an organic solvent selected from organic alcohols, for instance, ethanol, octyldodecanol, butylene glycol, dipropylene glycol, propanediol, and propylene glycol.
  • organic solvent selected from organic alcohols, for instance, ethanol, octyldodecanol, butylene glycol, dipropylene glycol, propanediol, and propylene glycol.
  • the organic solvent acts as the cores of the reverse micelles to encapsulate organic solvent soluble active ingredients.
  • the organic solvent is present in an amount ranging from 0.1 wt. %to 10 wt. %, preferably from 0.2 wt. %to 5 wt. %, more preferably from 0.3 wt. %to 2 wt. %, relative to the total weight of the composition.
  • the composition comprises a cosmetic active ingredient with the solubility in the organic solvent of no less than 10 g.
  • the cosmetic active ingredient can exist either inside the organic solvent-containing cores of the micelles or at the solvent-oil interface.
  • UV filters such as avobenzone, homosalate, ethylhexyl salicylate, octocrylene; ceramide, such as 2-oleamido-1, 3-octadecanediol, N-stearoyl-phytosphingosine, hydroxypalmitoyl sphinganine; tocopherol, and salicylic acid.
  • the cosmetic active ingredient is present in amount ranging from 0.001 wt. %to 5 wt. %, preferably from 0.01 wt. %to 2 wt. %, and more preferably from 0.1 wt. %to 1 wt. %, relative to the total weight of the composition.
  • composition according to the present invention may also comprise an effective amount of other ingredients, such as fragrances, preservatives and so on.
  • the present invention provides a transparent anhydrous composition for conditioning or caring for keratin materials comprising, relative to the total weight of the composition:
  • both the nonionic surfactant and the cationic surfactant are lipophilic.
  • composition according to the present invention can be prepared by mixing ingredients a) to c) , as essential ingredients, as well as additional ingredient (s) , as explained above.
  • the method and means to mix the above essential and optional ingredients are not limited. Any conventional method and means can be used to mix the above essential and optional ingredients to prepare the composition according to the present invention.
  • the preparing process of the composition according to the present invention does not require energy consuming step.
  • the presence of reverse micelles can be confirmed by measurement of the sizes of reverse micelles by Dynamic Light Scattering (DLS) .
  • DLS Dynamic Light Scattering
  • composition according to the present invention can be used as a conditioning leave-on or rinse-off product for haircare or skincare.
  • composition can potentially deliver the functions of the organic solvent soluble active ingredients to consumer perceivable benefits.
  • a cosmetic process for conditioning or caring for keratin materials comprising applying the composition as described above onto the keratin materials.
  • Leave-on oils according to invention formulas (IE. ) 1-3 and comparative formulas (CE. ) 1-3 were prepared with the ingredients listed in Table 2 (the contents are expressed as weight percentages of active material with regard to the total weight of each leave-on oil, unless otherwise indicated) :
  • Each leave-on oil was prepared as follows:
  • each leave-on oil obtained was evaluated by maintaining the leave-on oil at 4°C, room temperature (20°C) , or 45°C for 2 months and observing with naked eyes to check whether the leave-on oil was transparent. It will be evaluated as stable if the leave-on oil tested is transparent under all of 4°C, room temperature (20°C) , and 45°C for 2 months, otherwise, it will be evaluated as unstable.
  • Leave-on oils according to invention formulas (IE. ) 4-5 and comparative formula (CE. ) 4 were prepared with the ingredients listed in Table 4 (the contents are expressed as weight percentages of active material with regard to the total weight of each leave-on oil, unless otherwise indicated) :
  • Each leave-on oil was prepared as follows:
  • each leave-on oil obtained was evaluated by maintaining the leave-on oil at 4°C, room temperature (20°C) , or 45°C for 2 months and observing with naked eyes to check whether the leave-on oil was transparent. It will be evaluated as stable if the leave-on oil tested is transparent under all of 4°C, room temperature (20°C) , and 45°C for 2 months, otherwise, it will be evaluated as unstable.
  • Leave-on oils according to invention formula (IE. ) 6 and comparative formula (CE. ) 5 were prepared with the ingredients listed in Table 6 (the contents are expressed as weight percentages of active material with regard to the total weight of each leave-on oil, unless otherwise indicated) :
  • Each leave-on oil was prepared as follows:
  • each leave-on oil obtained was evaluated by maintaining the leave-on oil at 4°C, room temperature (20°C) , or 45°C for 2 months and observing with naked eyes to check whether the leave-on oil was transparent. It will be evaluated as stable if the leave-on oil tested is transparent under all of 4°C, room temperature (20°C) , and 45°C for 2 months, otherwise, it will be evaluated as unstable.
  • the sizes of the reverse micelles were characterized using a Brookhaven dynamic light scattering (DLS) equipment.
  • the main experimental parameters set for the DLS experiments were listed in Table 8.
  • the effective diameter and polydispersity index were obtained from at least three measurements.
  • the average effective diameter and average polydispersity index were summarized in Table 9.
  • Polydispersity Index was a dimensionless measure of the broadness of the size distribution calculated from the cumulants analysis. This value should range from 0 to 1. If this value was higher than 1, then the sample might not be suitable for measurement by DLS.
  • Figs. 1-6 show the multimodal size distribution of leave-on oils of invention examples 1-6.
  • each leave-on oil of invention examples 1-6 obtained an average polydispersity of lower than 1.
  • reverse micelles having the average effective diameters as shown in Table 9 were formed and were stable over time in the leave-on oils of invention examples 1-6.

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PCT/CN2021/119901 2021-09-23 2021-09-23 Composition for conditioning or caring for keratin materials WO2023044666A1 (en)

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PCT/CN2021/119901 WO2023044666A1 (en) 2021-09-23 2021-09-23 Composition for conditioning or caring for keratin materials
CN202180102673.6A CN117979945A (zh) 2021-09-23 2021-09-23 用于调理或护理角蛋白材料的组合物
FR2111174A FR3127132B1 (fr) 2021-09-23 2021-10-21 composition pour le conditionnement ou le soin des matières kératineuses

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Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20030103930A1 (en) * 2001-10-30 2003-06-05 The Procter & Gamble Company Anhydrous cosmetic compositions containing quaternary ammonium compounds
US20040022823A1 (en) * 2001-02-01 2004-02-05 The Procter & Gamble Company Anhydrous cosmetic compositions
CN1476320A (zh) * 2000-11-20 2004-02-18 �ź㴫 用于处理角蛋白纤维的含有阳离子缔合性聚氨酯聚合物和保护或调理剂的组合物
CN1977792A (zh) * 2005-10-28 2007-06-13 莱雅公司 含有阳离子、液体脂肪物质和失水山梨醇酯的化妆品组合物，以及美容处理方法
US20080131391A1 (en) * 2006-12-01 2008-06-05 L'oreal Compositions containing a quaternary ammonium polymer, a fatty quaternary agent and a nonionic surfactant

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Publication number Priority date Publication date Assignee Title
FR2779639B1 (fr) 1998-06-15 2000-08-04 Oreal Composition cosmetique contenant un polyorganosiloxane et un terpolymere acrylique et utilisation de cette composition pour le traitement des matieres keratiniques
US6440456B1 (en) 1999-06-09 2002-08-27 L'oreal S.A. Aqueous carrier systems for lipophilic ingredients
FR3015246B1 (fr) * 2013-12-24 2017-10-06 Oreal Composition cosmetique comprenant une huile, un tensioactif non ionique et un compose c-glycoside

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN1476320A (zh) * 2000-11-20 2004-02-18 �ź㴫 用于处理角蛋白纤维的含有阳离子缔合性聚氨酯聚合物和保护或调理剂的组合物
US20040022823A1 (en) * 2001-02-01 2004-02-05 The Procter & Gamble Company Anhydrous cosmetic compositions
US20030103930A1 (en) * 2001-10-30 2003-06-05 The Procter & Gamble Company Anhydrous cosmetic compositions containing quaternary ammonium compounds
CN1977792A (zh) * 2005-10-28 2007-06-13 莱雅公司 含有阳离子、液体脂肪物质和失水山梨醇酯的化妆品组合物，以及美容处理方法
US20080131391A1 (en) * 2006-12-01 2008-06-05 L'oreal Compositions containing a quaternary ammonium polymer, a fatty quaternary agent and a nonionic surfactant

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