WO2013150044A2 - Composition cosmétique comprenant une huile essentielle spécifique et un ester d'un acide aminé et d'un alcool gras - Google Patents

Composition cosmétique comprenant une huile essentielle spécifique et un ester d'un acide aminé et d'un alcool gras Download PDF

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Publication number
WO2013150044A2
WO2013150044A2 PCT/EP2013/056972 EP2013056972W WO2013150044A2 WO 2013150044 A2 WO2013150044 A2 WO 2013150044A2 EP 2013056972 W EP2013056972 W EP 2013056972W WO 2013150044 A2 WO2013150044 A2 WO 2013150044A2
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Prior art keywords
essential oil
weight
alcohol
composition
composition according
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PCT/EP2013/056972
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English (en)
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WO2013150044A3 (fr
Inventor
Olga Biganska
Céline VALENTIN-GOMARD
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L'oreal
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Publication of WO2013150044A3 publication Critical patent/WO2013150044A3/fr

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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
    • A61K8/18—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
    • A61K8/342—Alcohols having more than seven atoms in an unbroken chain
    • 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
    • A61K8/062—Oil-in-water 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
    • A61K8/37—Esters of carboxylic acids
    • 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
    • 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
    • A61K8/44—Aminocarboxylic acids or derivatives thereof, e.g. aminocarboxylic acids containing sulfur; Salts; Esters or N-acylated derivatives thereof
    • 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
    • A61K8/922—Oils, fats or waxes; Derivatives thereof, e.g. hydrogenation products thereof of vegetable origin
    • 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

Definitions

  • Cosmetic composition comprising a specific essential oil and an ester of an amino acid and of a fatty alcohol
  • the present invention relates to a cosmetic composition in the emulsion form comprising one or more specific essential oils and one or more esters of an amino acid and of a fatty alcoho l.
  • the present invention also relates to a method for the cosmetic treatment of keratinous substances using such a composition and to a cosmetic use of the said composition.
  • a recurring problem in the field of cosmetics consists in caring for keratinous substances, in particular keratinous fibres, subj ected to various external assaults. These fibres may be subj ected to assaults o f various origins, such as mechanical assaults, for example linked to disentangling or blow-drying, or also chemical assaults, for example subsequent to dyeing or permanent-waving.
  • Care products which can limit these phenomena. These products generally comprise one or more agents for conditioning keratinous fibres, such as po lymers, cationic surfactants or silicones .
  • natural compound is understood to mean a compound which is obtained directly from the earth or the soil, or from plants or animals, via, if appropriate, one or more physical processes, such as, for example, a milling, a refining, a distillation, a purification or a filtration.
  • compounds of natural origin is understood to mean a natural compound which has been subjected to one or more additional chemical or industrial treatments, giving rise to modifications which do not affect the essential qualities of this compound, and/or a compound predominantly comprising natural constituents which have or have not been subjected to transformations as indicated above.
  • a subject-matter of the present invention is thus a cosmetic composition in the emulsion form comprising one or more cationic emulsifiers chosen from esters of a neutral amino acid, the amine functional group of which is partially or completely neutralized, and of a C8-C50 fatty alcohol, and one or more essential oils chosen from sweet orange essential oil, lemongrass essential oil (citronella), lemon balm essential oil, clove essential oil, coriander essential oil, fennel essential oil, geranium essential oil, cinnamon essential oil, cedar essential oil, camomile essential oil, oregano essential oil, catnip essential oil, savory essential oil, thyme essential oil and their mixtures.
  • This specific combination has proven to be particularly appropriate for washing and/or caring for the hair and has made it possible to obtain good cosmetic properties .
  • this composition provides goo d conditioning o f the hair, for example in terms of disentangling, smoothing, bo dy, sheen, suppleness and coating .
  • a further subj ect-matter o f the present invention is a metho d for the treatment of keratinous substances , in particular human keratinous fibres, such as the hair, in which a cosmetic compositio n according to the invention is applied to the said keratinous substances .
  • a subj ect-matter o f the present invention is a use o f a cosmetic composition according to the invention in the treatment of keratinous substances, in particular in the conditioning o f keratinous fibres , in particular the hair.
  • the composition comprises one or more essential o ils chosen from sweet orange essential oil, lemongrass essential o il (citronella), lemon balm essential o il, clove essential o il, coriander essential o il, fennel essential oil, geranium essential o il, cinnamon essential oil, cedar essential oil, camomile essential o il, oregano essential o il, catnip essential o il, savory essential o il, thyme essential o il and their mixtures, and one or more cationic emulsifiers chosen from esters o f a neutral amino acid, the amine functional group o f which is partially or completely neutralized, and of a Cs -Cso fatty alcoho l.
  • one or more cationic emulsifiers chosen from esters o f a neutral amino acid, the amine functional group o f which is partially or completely neutralized, and of a Cs -Cso
  • the specific cationic emulsifiers present in the compositio ns according to the invention are neutralized amino acid ester cationic emulsifiers which are preferably of natural origin, given that they are not derived from petrochemicals , and can also be produced from non- animal-derived and non-GMO reactants, and be prepared by processes which use the princip les of green chemistry. Due to the cationic structure of the ester, it is well suited to personal care applications , in particular to compositions used in the conditioning o f the hair and skin.
  • the neutralized amino acid ester of use in the context o f the invention is derived from the esterification o f (i) a neutral amino acid with (ii) a fatty alcoho l comprising a long Cs -Cso chain, the amine functional group of the amino acid being partially or completely neutralized.
  • suitable amino acid esters are derived fro m the esterification o f a neutral amino acid having a hydro carbon side chain with a fatty alco ho l comprising a long Cs - Cso chain.
  • the cationic emulsifier or emulsifiers of use in the context o f the invention can be defined by the structure of fo llowing formula (I) , in which the amine functional group is completely or partially neutralized with an acid :
  • Ri represents a linear or branched alkyl group having from one to ten carbon atoms , preferably from two to six carbon atoms ;
  • R 2 represents a saturated or unsaturated and linear or branched hydro carbon chain comprising from 8 to 50 carbon atoms, preferab ly from 1 0 to 24 carbon atoms and more preferably still from 1 6 to 24 carbon atoms .
  • the amino acids for the formation of the ester comprise any acid from those which are neutral.
  • L-alanine, L- valine, L-leucine and L-isoleucine can be selected. Preference is in particular given, in some embodiments of the invention, to L- isoleucine.
  • the neutral amino acid selected not to be derived from animal sources or GMO sources.
  • the amino acid(s) may be synthetic and/or derived from plants, algae or other non-animal organisms. They can be obtained, for example, from plant matter by a fermentation process.
  • the amine group of the amino acid is neutralized with an acid and reacted with a fatty alcohol comprising a long Cs-Cso chain.
  • the fatty alcohol or alcohols used in the synthesis of the ester or esters constituting the cationic emulsifier or emulsifiers present in the composition according to the invention can be linear or branched and can in addition be saturated or unsaturated.
  • the fatty alcohol comprises from 8 to 50 carbon atoms. In one embodiment, the linear or branched fatty alcohol or alcohols comprising from 8 to 24 carbon atoms may be preferred.
  • Suitable fatty alcohols comprise lauryl alcohol, myristyl alcohol, palmityl alcohol, stearyl alcohol, oleyl alcohol, isostearyl alcohol, arachidyl alcohol, behenyl alcohol and mixtures or combinations of these. It is recommended for the fatty alcohols to be derived from non-petrochemical sources.
  • the amine group of the amino acid ester can be completely or partially neutralized by an acid, in order to facilitate its cationic behaviour.
  • Any acid can be used, including organic and inorganic acids.
  • Suitable inorganic (or mineral) acids comprise, without limitation, hydrochloric acid, phosphoric acid, sulphuric acid, boric acid and nitric acid.
  • Suitable organic acids can be citric acid, ethanesulphonic acid, acetic acid, formic acid and oxalic acid. Mention may also be made, among organic acids, of amino acids, for example glutamic acid and aspartic acid. In one embodiment, preference may be given to an ethanesulphonic acid which is derived from non-GMO ethano l.
  • An example of preferred neutralized amino acid ester can be brassicyl-L-iso leucine esylate (BLIE) or leucine isostearyl ester esylate (LIEE) .
  • the brassicyl-L-iso leucine esylate (BLIE) can be derived from the esterification o f brassica alcoho l with L-iso leucine esylate.
  • the L-iso leucine esylate can be prepared by reaction o f the amine group on the isoleucine with ethanesulphonic acid.
  • Brassica alcoho l is a fatty alcoho l which is derived from the separation o f rapeseed oil rich in erucic acid obtained from the Brassica genus o f plants, fo llowed by a hydrogenation.
  • Brassica alcoho l is composed mainly of stearyl (C 1 8 ), arachidyl (C 20 ) and behenyl (C 22 ) alcoho ls with minor amounts of alcoho ls comprising a shorter and longer alkyl chain length.
  • Emulsense which is a mixture o f 65 % Brassicyl Iso leucinate Esylate and 35 % Brassica Alcohol;
  • Emulsense SC which is a mixture of 50%> Brassica Alcohol, 25 % Brassicyl Isoleucinate Esylate and 25 % Brassica Glycerides;
  • Emulsense HC which is a mixture of 76% Brassica Alcoho l and 24% Brassicyl Isoleucinate Esylate.
  • the neutralized amino acid ester of the invention can be synthesized by processes well-known in the art.
  • the amount of cationic emulsifier(s) in the composition according to the invention is generally between 1 % and 20% by weight, preferably between 2% and 10% by weight, of the total weight of the composition.
  • composition according to the invention comprises one or more essential oils chosen from sweet orange essential oil, lemongrass essential oil (citronella), lemon balm essential oil, clove essential oil, coriander essential oil, fennel essential oil, geranium essential oil, cinnamon essential oil, cedar essential oil, camomile essential oil, oregano essential oil, catnip essential oil, savory essential oil, thyme essential oil and their mixtures.
  • essential oils chosen from sweet orange essential oil, lemongrass essential oil (citronella), lemon balm essential oil, clove essential oil, coriander essential oil, fennel essential oil, geranium essential oil, cinnamon essential oil, cedar essential oil, camomile essential oil, oregano essential oil, catnip essential oil, savory essential oil, thyme essential oil and their mixtures.
  • the composition according to the invention comprises at least one sweet orange essential oil, alone or as a mixture with one or more of the other essential oils listed.
  • the composition according to the invention comprises at least one sweet orange essential oil and one lemongrass essential oil.
  • composition can, in addition, optionally comprise one or more other additional essential oils, such as rosemary essential oil.
  • the composition according to the invention comprises at least one sweet orange essential oil, one lemongrass essential oil and one rosemary essential oil.
  • Essential oils are o ften used for their odour but also for their many other pharmaceutical and/or cosmetic activities, which have been known from a very early date (see in particular Aromatherapie by J. Valnet, published by Maloine, 1984) .
  • Essential oils differ from vegetable oils in that they cannot be decomposed by saponification into glycerol and fatty acid soap . Moreover, they are vo latile.
  • an essential oil is a product, generally of complex composition, obtained from a botanically defined plant starting material, either by steam distillation, or by dry distillation, or by extraction using liquid or gaseous solvents, or via an appropriate mechanical process without heating (co ld expression) .
  • the essential oil is generally separated from the aqueous phase via a physical process which does not result in any significant change in the composition.
  • These essential oils can also be prepared by synthesis.
  • the essential oil used according to the invention can be obtained from any plant material resulting from the whole plant or from any part of the said plant, such as, for example, the leaves, stems, flowers, petals, seeds, fruits, buds, roots, branches of plants and/or whole plants .
  • the essential oil in accordance with the invention can be prepared according to the abovementioned techniques and will preferably be obtained according to the conventional technique o f steam distillation or of co ld expression o f the peel and/or of the whole fruit (in the case o f citrus fruits in particular).
  • Citrus aurantium dulcis peel oil Mention may be made, as orange essential oil, of Citrus aurantium dulcis peel oil, so ld by Elixens under the reference Citrus Aurantium Dulcis Peel Oil.
  • the essential oil or oils are generally present in proportions o f 0.01 % to 20% by weight, preferably of 0.05 % to 1 5 % by weight, better still o f 0. 1 % to 10% by weight, even better still o f 0.2% to 5 % by weight and better still of 0.5 %> to 3 %> by weight, with respect to the total weight of the composition.
  • composition according to the invention can also comprise one or more additional surfactants chosen from anionic, non-ionic or amphoteric surfactants, in particular non-ionic surfactants, but only in so far as the presence of these surfactants does not affect the comfort (harmlessness) of the composition.
  • additional surfactants chosen from anionic, non-ionic or amphoteric surfactants, in particular non-ionic surfactants, but only in so far as the presence of these surfactants does not affect the comfort (harmlessness) of the composition.
  • the additional surfactants which can be used in the composition according to the invention are preferably surfactants o f natural origin, in which the compounds which may be present in nature and which are reproduced by chemical synthesis are included; they can in particular be chosen from esters of a sugar and of a fatty acid, soaps (salts o f fatty acids), soybean oil derivatives, lactic acid derivatives, amino acids, acylamino acids, their salts, alkyl polyglucosides (APG), hydrophobized gums and their mixtures.
  • surfactants o f natural origin in which the compounds which may be present in nature and which are reproduced by chemical synthesis are included; they can in particular be chosen from esters of a sugar and of a fatty acid, soaps (salts o f fatty acids), soybean oil derivatives, lactic acid derivatives, amino acids, acylamino acids, their salts, alkyl polyglucosides (APG), hydrophobized gums and their mixtures.
  • composition in accordance with the invention is provided in the emulsion form.
  • composition in accordance with the invention is provided in the oil-in- water emulsion form.
  • composition according to the invention comprises an aqueous phase comprising water and/or water-soluble solvents.
  • the water optionally used in the composition of the invention can be demineralized pure water but also mineral water and/or thermal water and/or seawater and/or floral waters (hydrolates), that is to say that the water of the composition can be partially or completely composed o f a water chosen from mineral waters, thermal waters, seawaters, floral waters (hydrolates) and their mixtures .
  • a mineral water is suitable for consumption, which is not always the case with a thermal water.
  • Each of these waters comprises, inter alia , trace elements and/or dissolved minerals.
  • These waters are known to be emp loyed for specific treatment purposes according to the particular trace elements and minerals which they contain, such as the moisturization and desensitization of the skin or the treatment of certain dermatoses.
  • mineral waters and “thermal waters” will denote not only natural mineral or thermal waters but also natural mineral or thermal waters enriched in additional mineral constituents and/or trace elements, and also aqueous mineral solutions and/or aqueous so lutions containing trace elements prepared from purified water (demineralized or distilled water) .
  • a natural thermal water or mineral water optionally used according to the invention can, for example, be chosen from water from Vittel, water from the Vichy basin, water from Uriage, water from La Roche-Posay, water from La Bourboule, water from Enghien- les-Bains, water from Saint Gervais-les-Bains, water from Neris- les- Bains, water from Allevard-les-Bains, water from Digne, water from Maizieres, water from Neyrac-les-Bains, water from Lons-le-Saunier, water from Eaux-Bonnes, water from Rochefort, water from Saint Christau, water from Les Fumades, water from Tercis-les-Bains and water from Avene.
  • the aqueous phase of the composition o f the invention can comprise a water-so luble organic solvent chosen, for example, from lower monoalcoho ls comprising from 1 to 8 carbon atoms and in particular from 1 to 6 carbon atoms, such as ethanol, isopropanol, propanol or butanol, polyols, such as, for example, glycerol, propylene glycol, butylene glycol, hexylene glycol, polyethylene glycols, such as PEG-8, or dipropylene glycol, and their mixtures.
  • a water-so luble organic solvent chosen, for example, from lower monoalcoho ls comprising from 1 to 8 carbon atoms and in particular from 1 to 6 carbon atoms, such as ethanol, isopropanol, propanol or butanol, polyols, such as, for example, glycerol, propylene glycol, butylene glycol, hexy
  • the polyol is glycerol, which gives better comfort on application.
  • Other polyols can be added to the glycerol, in so far as the qualities of the composition are maintained.
  • the amount of water in the aqueous phase is advantageously between 40% and 95% by weight, in particular 50% and 90% by weight, with respect to the total weight of the aqueous phase.
  • the amount of polyol(s) in the aqueous phase can range, for example, from 0% to 15% by weight, preferably from 0.5% to 10% by weight, better still from 1% to 10% by weight, even better still from 2%> to 10%) by weight and even better still from 2% to 8% by weight, with respect to the total weight of the aqueous phase.
  • the glycerol represents from 0% to 10% by weight of the total weight of the aqueous phase.
  • composition according to the invention also comprises a fatty phase.
  • the fatty phase of the composition according to the invention comprises all of the fat-soluble or fat-dispersible compounds present in the composition, including, preferably, the fatty substances which are liquid at ambient temperature (25°C) and ambient pressure or oils (which form the oily phase), fatty substances which are solid at ambient temperature, such as waxes, or also pasty compounds, fatty alcohols, fatty acids, and esters of an unsaturated C 6 -Ci 6 acid, in particular Cs-Ci4 acid, and of a C 6 -Cio alcohol, in particular C 6 -C8 alcohol, other than the neutral amino acid esters defined above.
  • oils which can be used in the composition of the invention for example, of:
  • hydrocarbon oils of vegetable origin such as squalane, liquid triglycerides of fatty acids comprising from 4 to 30 carbon atoms, such as heptanoic or octanoic acid triglycerides, or alternatively, for example, jojoba oil, babassu oil, sunflower oil, olive oil, coconut oil, Brazil nut oil, marula oil, maize oil, soybean oil, pumpkinseed oil, grape seed oil, linseed oil, sesame seed oil, hazelnut oil, apricot oil, macadamia oil, arara oil, coriander oil, castor oil, avocado oil, rapeseed oil, caprylic/capric acid triglycerides, such as those sold by Stearineries Dubois or those sold under the names Miglyol 8 1 0, 8 12 and 8 1 8 by Dynamit Nobel, or shea butter oil;
  • esters and ethers in particular of fatty acids, such as the oils o f formulae R' COOR 2 and R' OR 2 in which R 1 represents the residue of a fatty acid or of a fatty alcohol comprising from 8 to 29 carbon atoms and R 2 represents a branched or unbranched hydrocarbon chain comprising from 3 to 30 carbon atoms, such as, for example, purcellin oil, 2-octyldodecyl stearate, 2-octyldodecyl erucate or isostearyl isostearate; hydroxylated esters, such as isostearyl lactate, octyl hydroxystearate, octyldodecyl hydroxystearate, diisostearyl malate, triisocetyl citrate, and fatty alcohol heptanoates, octanoates and decanoates; polyo l esters, such as propylene glyco l dio
  • esters resulting from the reaction o f at least one fatty acid comprising at least 6 carbon atoms, preferably from 6 to 26 carbon atoms, better still from 6 to 20 carbon atoms and even better still from 6 to 16 carbon atoms and of at least one alcohol comprising from 1 to 17 carbon atoms and better still from 3 to 1 5 carbon atoms; mention may in particular be made o f isopropyl myristate, isopropyl palmitate, 2-ethylhexyl caprate/caprylate (or octyl caprate/caprylate), 2- ethylhexyl palmitate, isostearyl neopentanoate, isononyl isononanoate, hexyl laurate, lauryl laurate, esters of lactic acid and of fatty alcoho ls comprising 12 or 1 3 carbon atoms, or dicaprylyl carbonate, such as the product which is so ld under the name Cet
  • - ethers o f a fatty acid comprising from 6 to 20 carbon atoms, such as dicaprylyl ether (Cetio l OE from Cognis), - glycerol ethers comprising from 6 to 12 carbon atoms, such as the 2-ethylhexyl ether of glycerol (INCI name: ethylhexylglycerin), such as Sensiva SC 50 from Schulke & Mayr GmbH,
  • linear alkanes advantageously of vegetable origin, comprising from 7 to 17 carbon atoms, in particular from 9 to 15 carbon atoms and more particularly from 11 to 13 carbon atoms.
  • n-nonane C9
  • n-decane C 10
  • n- undecane Cn
  • n-dodecane C 12
  • n-tridecane C 13
  • n-tetradecane C14
  • n-pentadecane C 15
  • n-hexadecane C 16
  • n-heptadecane C 17
  • n-undecane (Cn) and n-tridecane (C 13 ) obtained in Examples 1 and 2 of Patent Application WO 2008/155059 from Cognis. Mention may also be made of n-dodecane (C 12 ) and n- tetradecane (C 14 ), such as those sold by Sasol under the references Parafol 12-97 and Parafol 14-97 respectively, and also of their mixtures,
  • polyesters obtained by condensation of an unsaturated fatty acid dimer and/or trimer and of a diol such as the polyesters of dilinoleic acid and of a diol sold by Biosynthis under the name Viscoplast and in particular the polymer carrying the INCI name dilinoleic acid/propanediol copolymer,
  • the oil is chosen from vegetable oils, such as mentioned above.
  • pasty compound is understood to mean a lipophilic fatty compound with a reversible solid/liquid change in state and comprising, at a temperature of 23°C, a liquid fraction and a solid fraction.
  • a pasty compound is, at a temperature of 23°C, in the form of a liquid fraction and of a solid fraction. In other words, the starting melting point of the pasty compound is less than 23°C.
  • the liquid fraction of the pasty compound, measured at 23°C, represents from
  • 23°C more preferably represents from 25% to 85% and better still from
  • the liquid fraction by weight of the pasty compound at 23°C is equal to the ratio of the enthalpy of fusion consumed at 23°C to the enthalpy of fusion of the pasty compound.
  • the enthalpy of fusion consumed at 23°C is the amount of energy absorbed by the sample to change from the solid state to the state which it exhibits at 23°C, consisting of a liquid fraction and a solid fraction.
  • the enthalpy of fusion of the pasty compound is the enthalpy consumed by the compound in order to change from the solid state to the liquid state.
  • the pasty compound is said to be in the solid state when all of its mass is in the solid form.
  • the pasty compound is said to be in the liquid state when all of its mass is in the liquid form.
  • the enthalpy of fusion of the pasty compound is equal to the area under the curve of the thermogram obtained using a differential scanning calorimeter (DSC), such as the calorimeter sold under the name MDSC 2920 by TA Instruments, with a temperature rise of 5°C or 10°C per minute, according to Standard ISO 11357-3:1999.
  • DSC differential scanning calorimeter
  • the enthalpy of fusion of the pasty compound is the amount of energy necessary to make the compound change from the solid state to the liquid state. It is expressed in J/g.
  • the liquid fraction of the pasty compound, measured at 32°C preferably represents from 40% to 100% by weight of the pasty compound, better still from 50%> to 100% by weight of the pasty compound.
  • the temperature of the end o f the melting range of the pasty compound is less than or equal to 32°C .
  • the liquid fraction of the pasty compound, measured at 32°C, is equal to the ratio of the enthalpy of fusion consumed at 32°C to the enthalpy o f fusion o f the pasty compound.
  • the enthalpy of fusion consumed at 32°C is calculated in the same way as the enthalpy o f fusion consumed at 23 ° C .
  • the pasty compound preferably has a hardness at 20°C ranging from 0.001 to 0.5 MPa and preferably from 0.002 to 0.4 MPa.
  • the hardness is measured according to a method of penetration of a probe into a compound sample, in particular using a texture analyser (for example the ⁇ - ⁇ 2 ⁇ from Rheo) equipped with a stainless steel cylinder with a diameter of 2 mm.
  • the hardness measurement is carried out at 20°C at the centre of 5 samp les.
  • the cylinder is introduced into each sample, the depth of penetration being 0.3 mm.
  • the value recorded for the hardness is that of the maximum peak.
  • the pasty compound is chosen from compounds o f vegetable origin.
  • a pasty compound can be obtained by synthesis from starting materials o f vegetable origin.
  • the pasty compound can be chosen in particular from isomerized jojoba oil, such as trans-isomerized partially hydrogenated jojoba oil manufactured or marketed by Desert Whale under the commercial reference Iso-Jojoba-50®, orange wax, such as, for example, that which is so ld under the reference Orange Peel Wax by Koster Keunen, cupuacu butter (Rain Forest RF34 10 from Beraca Sahara), murumuru butter (Rain Forest RF3710 from Beraca Sahara), shea butter, partially hydrogenated olive oil, such as, for example, the compound so ld under the reference Beurrolive by Soliance, cocoa butter, kokum butter, mango oil, such as, for example, Lipex 203 from AarhusKarlshamn, and their mixtures.
  • isomerized jojoba oil such as trans-isomerized partially hydrogenated jojoba oil manufactured or marketed by Desert Whale under the commercial reference Iso-Jojoba-50®
  • the term "wax” is understood to mean a lipophilic compound which is solid at ambient temperature (25 °C), which exhibits a reversible solid/liquid change in state and which has a melting point o f greater than or equal to 30°C and which can range up to 120°C .
  • the waxes exhibit a melting point o f greater than 30°C and better still of greater than 45 °C .
  • the melting point corresponds to the temperature of the most endothermic peak observed in thermal analysis (differential scanning calorimetry or DSC), as described in Standard ISO 1 1 357-3 ; 1999.
  • the melting point of the wax can be measured using a differential scanning calorimeter (DSC), for example the calorimeter sold under the name MDSC 2920 by TA Instruments .
  • DSC differential scanning calorimeter
  • the measurement protocol is as fo llows :
  • a sample of 5 mg of wax placed in a crucible is subj ected to a first temperature rise ranging from -20°C to 1 00°C, at a heating rate of 10°C/minute, it is then cooled from 100°C to -20°C at a cooling rate of 10°C/minute and it is finally subj ected to a second temperature rise ranging from -20°C to 100°C at a heating rate of 5 °C/minute.
  • the variation in the difference in power absorbed by the empty crucible and by the crucible containing the sample o f wax is measured as a function of the temperature.
  • the melting point o f the compound is the value of the temperature corresponding to the tip of the peak of the curve representing the variation in the difference in power absorbed as a function o f the temperature.
  • hard wax is understood to mean, within the meaning of the present invention, a wax exhibiting, at 20°C, a hardness o f greater than 5 MPa, in particular ranging from 5 to 30 MPa, preferably of greater than 6 MPa, better still ranging from 6 to 25 MPa.
  • the hardness of the wax is determined by measuring the compressive force, measured at 20°C using the texture analyser sold under the name TA-XT2 by Rheo, equipped with a stainless steel cylinder with a diameter of 2 mm, moving at a measurement rate of 0. 1 mm/s and penetrating the wax to a penetration depth of 0.3 mm.
  • the measurement protocol is as fo llows : the wax is melted at a temperature equal to the melting point of the wax + 10°C .
  • the mo lten wax is poured into a container with a diameter of 25 mm and a depth of 20 mm.
  • the wax is recrystallized at ambient temperature (25 °C) for 24 hours, so that the surface of the wax is flat and smooth, and then the wax is stored at 20°C for at least 1 hour before measuring the hardness or the tack.
  • the spindle o f the texture analyser is moved at the rate of 0. 1 mm/s and then penetrates the wax down to a penetration depth of 0.3 mm.
  • the spindle is kept stationary for 1 second (corresponding to the relaxation time) and is then withdrawn at the rate of 0.5 mm/s .
  • the value o f the hardness is the maximum compressive force measured divided by the surface area of the cylinder of the texture analyser in contact with the wax.
  • wax of waxes o f vegetable origin, such as carnauba wax, candelilla wax, hydrogenated jojoba wax, mimoza wax, sumac wax, the waxes obtained by hydrogenation o f o live oil esterified with fatty alcoho ls comprising C i 2 to C i 8 chains so ld by Sophim in the Phytowax range ( 12L44, 14L48 , 16L55 and 1 8L57), rice bran wax, cetyl, stearyl and behenyl alcoho ls, laurel wax or ouricury wax.
  • waxes o f vegetable origin such as carnauba wax, candelilla wax, hydrogenated jojoba wax, mimoza wax, sumac wax
  • Use may also be made o f at least one ester of behenic acid and of glycerol and in particular o f a mixture of esters o f behenic acid and of glycerol, such as, for examp le, the glyceryl dibehenate, tribehenin and glyceryl behenate mixture sold by Gattefosse under the reference Comprito l 888 CG ATO .
  • the fatty alcoho ls which can be used in the composition according to the invention are saturated or unsaturated and linear or branched and comprise from 6 to 30 carbon atoms and more particularly from 8 to 30 carbon atoms . Mention may be made, for example, of cetyl alcoho l, stearyl alcoho l and their mixture (cetearyl alcoho l), octyldodecanol, 2-butyloctanol, 2-hexyldecanol, 2- undecylpentadecanol, oleyl alcoho l or linoleyl alcoho l.
  • the fatty acids capable of being used in the composition can be saturated or unsaturated and comprise from 6 to 30 carbon atoms, in particular from 9 to 30 carbon atoms. They are more particularly chosen from myristic acid, palmitic acid, stearic acid, behenic acid, oleic acid, linoleic acid, linolenic acid and isostearic acid.
  • composition according to the invention can also comprise one or more esters of an unsaturated C 6 -Ci6 acid, in particular Cs-Ci4 acid, and of a C 6 -Cio alcohol, in particular C 6 -C8 alcohol, other than the neutral amino acid esters defined above. Mention may in particular be made of heptyl undecylenate. This compound is sold by Inolex under the commercial reference Lexfeel Natural.
  • the ester or esters of an unsaturated C 6 -Ci6 acid and of a C 6 - Cio alcohol other than the neutral amino acid esters defined above can represent from 0.1% to 10% by weight, preferably from 0.5%> to 6% by weight and better still from 1% to 5% by weight of the total weight of the composition.
  • the amount of fatty phase in the composition of the invention can range from 1% to 60% by weight, preferably from 1.5% to 30% by weight and indeed even from 2% to 15% by weight, with respect to the total weight of the composition.
  • the cosmetic compositions of the invention can additionally comprise adjuvants normal in the cosmetics field, such as pH agents, for example citric acid or arginine, antioxidants, preservatives, for example a benzyl alcohol/dehydroacetic acid mixture (sold under the reference Geogard 221 by Lonza), fragrances, peptizing agents for fragrances, colouring materials, fillers, or hydrophilic or lipophilic active agents.
  • adjuvants normal in the cosmetics field such as pH agents, for example citric acid or arginine, antioxidants, preservatives, for example a benzyl alcohol/dehydroacetic acid mixture (sold under the reference Geogard 221 by Lonza), fragrances, peptizing agents for fragrances, colouring materials, fillers, or hydrophilic or lipophilic active agents.
  • the nature of the adjuvants and their amounts must be such that they do not modify the properties of the composition according to the invention.
  • the amounts of these adjuvants are those conventionally used in the cosmetic
  • active agents which can be used in the composition of the invention, for example, of soothing agents, such as allantoin and bisabo lo l; floral waters, such as linden tree water or cornflower water; glycyrrhetinic acid and its salts; antibacterial agents, such as octopirox, triclo san and triclocarban; essential oils; vitamins, such as, for example, retino l (vitamin A), ascorbic acid (vitamin C), tocopherol (vitamin E), niacinamide (vitamin PP or B3), pantheno l (vitamin B5) and their derivatives, such as, for example, esters of these vitamins (palmitate, acetate, propionate), magnesium ascorbyl phosphate, glycosylated vitamin C or glucopyranosyl- ascorbic acid (ascorbyl glucoside); coenzymes, such as coenzyme Q 10 or ubiquinone and coen
  • soothing agents such as
  • mineral fillers such as talc or magnesium silicate (particle size : 5 microns)
  • kaolin or aluminium silicate such as
  • Fibres such as, for example, nylon fibres (Polyamide 0.9 Dtex 0.3 MM, sold by Etablatoriums Paul Bonte), or cellulo se or "Rayon” fibres (Rayon Flo ck RCISE N0003 M04®, sold by Claremont Flock Corporation), can also be added to the composition o f the invention.
  • compositions according to the invention are intended to be applied to keratinous substances, such as the skin (body, face, eyes, scalp) and/or keratinous fibres, and can constitute in particular care, make-up, make-up-removing or cleansing products for keratinous substances, or hair products.
  • Another subject-matter of the invention is a method for the cosmetic treatment of keratinous substances, in particular human keratinous fibres, such as the hair, in which a cosmetic composition as defined above is applied to the said keratinous substances.
  • Another subject-matter of the invention is the use o f a cosmetic composition as defined above in the treatment of keratinous substances, in particular in the conditioning o f keratinous fibres, in particular the hair.
  • compositions for the hair were prepared; their compositions are given in Table 1 .
  • the amounts are expressed as percentage by weight, with respect to the total weight of the composition.
  • composition 1 The conditioning properties on hair o f a composition according to the invention (composition 1 ) were compared in comparison with a composition not comprising an essential oil (composition 2).
  • composition was applied to 3 bleached blonde locks (SA 20), after a prior shampooing, in a proportion of 1 g of composition per lock of 2.7 g.
  • composition 1 according to the invention.
  • Table 3 An examp le o f a care composition for the hair according to the invention is given in Table 3. The amounts are expressed as percentage by weight, with respect to the total weight of the composition. Table 3
  • Emulsense HC sold by Inolex

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Abstract

L'invention a pour objet une composition cosmétique qui se présente sous la forme d'une émulsion comprenant : un ou plusieurs émulsifiants cationiques choisis entre les esters d'un acide aminé neutre dont le groupe fonctionnel amine est neutralisé partiellement ou complètement, et d'un alcool gras en C8-C50 ; et une ou plusieurs huiles essentielles choisies entre l'huile essentielle d'orange douce, l'huile essentielle de citronnelle, l'huile essentielle de mélisse, l'huile essentielle de clou de girofle, l'huile essentielle de coriandre, l'huile essentielle de fenouil, l'huile essentielle de géranium, l'huile essentielle de cannelle, l'huile essentielle de cèdre, l'huile essentielle de camomille, l'huile essentielle d'origan, l'huile essentielle de cataire, l'huile essentielle de sarriette, l'huile essentielle de thym et leurs mélanges. L'invention a également pour objet un procédé pour traiter des substances de kératine et une application cosmétique de la composition.
PCT/EP2013/056972 2012-04-05 2013-04-03 Composition cosmétique comprenant une huile essentielle spécifique et un ester d'un acide aminé et d'un alcool gras WO2013150044A2 (fr)

Applications Claiming Priority (4)

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FR1253148 2012-04-05
FR1253148A FR2988999B1 (fr) 2012-04-05 2012-04-05 Composition cosmetique comprenant une huile essentielle particuliere et un ester d'acide amine et d'alcool gras
US201261640187P 2012-04-30 2012-04-30
US61/640,187 2012-04-30

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EP3095437A1 (fr) * 2015-05-21 2016-11-23 Evonik Degussa GmbH Composition aqueuse contenant de l'acide amino-carboxylique oméga et de l'alcool gras
CN106572955A (zh) * 2014-05-09 2017-04-19 伊诺莱克斯投资公司 非石化衍生的阳离子乳化剂及相关组合物和方法
RU2680846C2 (ru) * 2014-11-04 2019-02-28 Джонсон энд Джонсон Консьюмер Инк. Очищающие композиции
FR3072290A1 (fr) * 2017-10-16 2019-04-19 Genialis Biotech Emulsion huile-dans-eau a base d’huiles essentielles et formulee sans tensio-actif
WO2019079313A1 (fr) * 2017-10-16 2019-04-25 Inolex Investment Corporation Compositions de conditionnement de tissu d'origine naturelle et procédés associés
CN109730963A (zh) * 2019-01-25 2019-05-10 泸州宇龙枳壳枳实研究院 一种枳壳挥发油微乳及其制备方法
WO2021195424A1 (fr) * 2020-03-27 2021-09-30 Stepan Company Compositions contenant des esters d'acides aminés neutralisés et des glycérides
US11633336B2 (en) 2020-08-11 2023-04-25 The Procter & Gamble Company Low viscosity hair conditioner compositions containing brassicyl valinate esylate
US11633338B2 (en) 2020-08-11 2023-04-25 The Procter & Gamble Company Moisturizing hair conditioner compositions containing brassicyl valinate esylate
US11672748B2 (en) 2020-12-01 2023-06-13 The Procter & Gamble Company Aqueous hair conditioner compositions containing solubilized anti-dandruff actives
US11696882B2 (en) 2020-08-11 2023-07-11 The Procter & Gamble Company Clean rinse hair conditioner compositions containing brassicyl valinate esylate
US11896693B2 (en) 2019-12-01 2024-02-13 The Procter & Gamble Company Hair conditioner compositions with a preservative system containing sodium benzoate and glycols and/or glyceryl esters

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AU2015255686B2 (en) * 2014-05-09 2020-08-13 Inolex Investment Corporation Non-petrochemically derived cationic emulsifiers, related compositions and methods
US11207249B2 (en) 2014-05-09 2021-12-28 Inolex Investment Corporation Non-petrochemically derived cationic emulsifiers and related compositions and methods
CN106572955A (zh) * 2014-05-09 2017-04-19 伊诺莱克斯投资公司 非石化衍生的阳离子乳化剂及相关组合物和方法
JP2017515824A (ja) * 2014-05-09 2017-06-15 イノレックス インベストメント コーポレイション 石油化学由来ではないカチオン性乳化剤、並びに関連する組成物及び方法
EP3139901A4 (fr) * 2014-05-09 2017-11-22 Inolex Investment Corporation Émulsifiants cationiques d'origine non pétrochimique et compositions et procédés associés
CN106572955B (zh) * 2014-05-09 2021-02-19 伊诺莱克斯投资公司 非石化衍生的阳离子乳化剂及相关组合物和方法
RU2680846C2 (ru) * 2014-11-04 2019-02-28 Джонсон энд Джонсон Консьюмер Инк. Очищающие композиции
AU2015343728B2 (en) * 2014-11-04 2021-02-18 Johnson & Johnson Consumer Inc. Cleansing compositions
WO2016184642A1 (fr) * 2015-05-21 2016-11-24 Evonik Degussa Gmbh Composition aqueuse contenant des esters de l'acide ω-aminocarboxylique et un alcool gras
EP3095437A1 (fr) * 2015-05-21 2016-11-23 Evonik Degussa GmbH Composition aqueuse contenant de l'acide amino-carboxylique oméga et de l'alcool gras
WO2019077258A1 (fr) * 2017-10-16 2019-04-25 Genialis Biotech Emulsion huile-dans-eau a base d'huiles essentielles et formulee sans tensio-actif
WO2019079313A1 (fr) * 2017-10-16 2019-04-25 Inolex Investment Corporation Compositions de conditionnement de tissu d'origine naturelle et procédés associés
FR3072280A1 (fr) * 2017-10-16 2019-04-19 Isabelle Desjardins-Lavisse Emulsion huile-dans-eau a base d’huiles essentielles et formulee sans tensio-actif
FR3072290A1 (fr) * 2017-10-16 2019-04-19 Genialis Biotech Emulsion huile-dans-eau a base d’huiles essentielles et formulee sans tensio-actif
CN109730963A (zh) * 2019-01-25 2019-05-10 泸州宇龙枳壳枳实研究院 一种枳壳挥发油微乳及其制备方法
US11896693B2 (en) 2019-12-01 2024-02-13 The Procter & Gamble Company Hair conditioner compositions with a preservative system containing sodium benzoate and glycols and/or glyceryl esters
US11957773B2 (en) 2019-12-01 2024-04-16 The Procter & Gamble Company Hair conditioner compositions containing behenamidopropyl dimethylamine
WO2021195424A1 (fr) * 2020-03-27 2021-09-30 Stepan Company Compositions contenant des esters d'acides aminés neutralisés et des glycérides
US11633336B2 (en) 2020-08-11 2023-04-25 The Procter & Gamble Company Low viscosity hair conditioner compositions containing brassicyl valinate esylate
US11633338B2 (en) 2020-08-11 2023-04-25 The Procter & Gamble Company Moisturizing hair conditioner compositions containing brassicyl valinate esylate
US11696882B2 (en) 2020-08-11 2023-07-11 The Procter & Gamble Company Clean rinse hair conditioner compositions containing brassicyl valinate esylate
US11672748B2 (en) 2020-12-01 2023-06-13 The Procter & Gamble Company Aqueous hair conditioner compositions containing solubilized anti-dandruff actives

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FR2988999A1 (fr) 2013-10-11
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