WO2019129683A1 - Composition cosmétique fouettée sous la forme d'une nanoémulsion comprenant au moins 20 % de substance grasse, au moins un tensioactif cationique, un gaz et de l'eau - Google Patents

Composition cosmétique fouettée sous la forme d'une nanoémulsion comprenant au moins 20 % de substance grasse, au moins un tensioactif cationique, un gaz et de l'eau Download PDF

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Publication number
WO2019129683A1
WO2019129683A1 PCT/EP2018/086485 EP2018086485W WO2019129683A1 WO 2019129683 A1 WO2019129683 A1 WO 2019129683A1 EP 2018086485 W EP2018086485 W EP 2018086485W WO 2019129683 A1 WO2019129683 A1 WO 2019129683A1
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WO
WIPO (PCT)
Prior art keywords
chosen
composition
oil
composition according
carbon atoms
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PCT/EP2018/086485
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English (en)
Inventor
Gérard Gabin
Aurore DION
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L'oreal
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Publication of WO2019129683A1 publication Critical patent/WO2019129683A1/fr

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Classifications

    • 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
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/02—Cosmetics or similar toiletry preparations characterised by special physical form
    • A61K8/04—Dispersions; Emulsions
    • A61K8/046—Aerosols; Foams
    • 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
    • A61K8/31—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
    • A61K8/34—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
    • 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
    • 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
    • A61K2800/21—Emulsions characterized by droplet sizes below 1 micron

Definitions

  • Whipped cosmetic composition in the form of a nanoemulsion comprising at least 20% of fatty substance, at least one cationic surfactant, a gas and water
  • the present invention relates to a whipped cosmetic composition in the form of an oil-in-water nanoemulsion comprising (i) one or more liquid fatty substances in a content ranging from 20% to 80% by weight relative to the total weight of the composition, (ii) one or more cationic surfactants, (iii) one or more gases and (iv) water.
  • the present invention also relates to a process for the cosmetic treatment of keratin materials, in particular keratin fibres, preferably human keratin fibres such as the hair, in which the composition is applied to said materials.
  • the invention relates to the use of the composition for the cosmetic treatment of keratin materials, in particular keratin fibres, preferably human keratin fibres such as the hair.
  • compositions in the form of nanoemulsions are well known in the cosmetics and dermatology domain, in particular for preparing cosmetic products such as lotions, creams, tonics, serums or eau de toilette to be applied to the skin and/or hair.
  • O/W oil-in-water type
  • US application US 2015/359728 discloses a pre aerated concentrated hair care composition further comprising fatty substances, non-ionic emulsifiers, and water. These compositions do not consist of whipped oil-in-water nanoemulsions, but of dispersions of fatty alcohols in the presence of microemulsified silicone. However, these compositions do not give complete satisfaction in terms of cosmetic properties on keratin fibres, in particular in term of uniform and effective deposit of the composition on the skin and/or hair, and of conditioning properties.
  • Compositions in nanoemulsion form generally have a number- average oil drop (or oily globule) size less than 100 nanometers, said oil drops being stabilized by a layer of amphiphilic molecules that can optionally form a liquid crystal phase of the lamellar type, located at the oil/aqueous phase interface.
  • amphiphilic molecule is intended to mean herein any molecule having a bipolar structure, i.e. including at least one hydrophobic part and at least one hydrophilic part and having the property of reducing the surface tension of water (g ⁇ 55mN/m) and of reducing the interface tension between water and an oily phase.
  • Amphiphilic molecules are for example surfactants, surface agents or emulsifiers.
  • compositions in the form of a nanoemulsion offer a certain number of advantages from a cosmetic or dermatological point of view leading in particular to a uniform and effective deposit of the composition on the skin and/or hair; in particular for the hair, a uniform deposit from the root to the end, while allowing satisfactory oil penetration and persistence.
  • compositions in nanoemulsion form confer improved cosmetic properties on keratin materials.
  • compositions in nanoemulsion form confer good disentangling, softness, feel, rinsability and also suppleness properties and have a very good conditioning effect, which usually prove to be better than those obtained with the conventional emulsions and dispersions used in the cosmetics field.
  • compositions in nanoemulsion form which have new innovative textures having improved usage qualities, while at the same time retaining the advantages offered by compositions of this type.
  • a whipped cosmetic composition in the form of a nanoemulsion comprising (i) at least 20% by weight relative to the total weight of the composition, of one or more fatty substances, (ii) one or more cationic surfactants, (iii) one or more gases and (iv) water makes it possible to meet the needs expressed above.
  • a subject of the invention is thus a whipped cosmetic composition in the form of an oil-in-water nanoemulsion comprising:
  • the cosmetic composition according to the invention is in the whipped form, that is to say in the form of an aerated composition, which brings about an improvement in the usage qualities, in particular during the application to keratin materials.
  • composition according to the invention has a light, creamy, luscious foam texture during its application to keratin fibres.
  • composition according to the invention can in particular be applied more accurately to the keratin materials, in particular the keratin fibres, i.e. in a more targeted manner at the point of application, while at the same time minimizing the risks of running and/or splashing, in particular into the eyes.
  • such an whipped texture advantageously results in a better localization of the composition on the keratin materials, in particular the keratin fibres, during its application, and also in uniform distribution and spreading.
  • the cosmetic composition according to the invention differs from the foams generated at the time of use by specific equipment, such as aerosol devices or any other pressurized container system comprising one or more propellants, or non-pressurized devices equipped with a foam-generating dispensing system.
  • specific equipment such as aerosol devices or any other pressurized container system comprising one or more propellants, or non-pressurized devices equipped with a foam-generating dispensing system.
  • the whipped composition according to the invention remains in aerated form, in particular in the form of a foam, which is stable over time, contrary to the foams obtained with the introduction of a gas at the time of use, which collapse very rapidly.
  • the cosmetic composition according to the invention is not dispensed by a pressurized or non-pressurized foam-generating device, in the whipped state at the time of use on the keratin materials.
  • the composition according to the invention is stable with respect to storage over time, both at ambient temperature (25 °C) and at higher temperatures, in particular 45°C.
  • stable with respect to storage over time is intended to mean that the following physical characteristics of the composition vary little, or even not at all, over time: appearance, pH, rheology (viscosity, consistency).
  • the composition does not give rise to any phase- separation or exudation phenomena over time, and at the intended storage temperature.
  • the whipped composition has a density that is stable over time within the meaning of the present invention, that is to say that it does not change over time, either at ambient temperature (25°C) or at higher temperatures, in particular 45°C .
  • the texture in the form of a foam of the composition does not collapse over time, either at ambient temperature (25°C) or at higher temperatures, in particular 45°C .
  • the whipped texture is preserved after 2 months of storage at 45°C .
  • composition above confers improved cosmetic properties on the keratin materials.
  • the composition according to the invention confers good rinsability properties, and good conditioning properties, in particular in terms of disentangling, softness, feel and suppleness.
  • the cosmetic composition according to the invention on contact with the keratin materials, is converted into a bluish-coloured milk, which makes it very easy and quick to rinse off.
  • Another subject of the present invention also relates to a process for the cosmetic treatment of keratin materials, in particular keratin fibres, preferably human keratin fibres such as the hair, in which the composition above is applied to said materials.
  • the invention relates to the use of the composition above for the cosmetic treatment of keratin materials, in particular keratin fibres, preferably human keratin fibres such as the hair.
  • keratin materials in particular keratin fibres, preferably human keratin fibres such as the hair.
  • the cosmetic composition according to the invention is preferably a cosmetic composition for treating keratin materials, preferably keratin fibres, in particular human keratin fibres such as the hair.
  • the term“whipped composition” is intended to mean a composition of which a portion of the volume is occupied by one or more gases, in particular air or an inert gas.
  • composition according to the invention generally has a lower density than the non-whipped conventional cosmetic compositions.
  • gas is intended to mean a compound that is gaseous at ambient temperature (25°C) and at atmospheric pressure ( 1 .013 c 10 5 Pa).
  • gases that can be used in the composition according to the invention are preferably air and/or an inert gas.
  • the inert gas is chosen from nitrogen, argon, helium and/or mixtures thereof.
  • the gas(es) that can be used in the composition according to the invention are preferably chosen from atmospheric air, inert gases and a mixture of these gases; more preferentially, from nitrogen, argon, helium, air, and a mixture of these gases; even more preferentially the gas is air.
  • the whipped compositions of the invention are stably formed in the form of a foam by means of a base composition and of one or more gases.
  • the gas(es) may represent in particular from 10% to 500% of the volume of the non-whipped composition, preferably from 30% to 200%, more preferentially from 35% to 150% and better still from 40% to 140%.
  • This volume may be calculated by comparing the density of the base composition and of the whipped composition.
  • This volume corresponds to the degree of expansion of the composition (or level of gas introduced into the composition), and may in particular be calculated by the following formula: .
  • this degree of expansion may in particular be measured on a composition which has already been whipped, using the following protocol:
  • the whipped composition is introduced into a 100 ml beaker so as to occupy the total beaker volume, while avoiding formation of air bubbles during the filling of the jar;
  • a turbine is introduced, and the beaker and the turbine are placed under a vacuum bell jar;
  • the vacuum is actuated and the blade of the turbine is rotated at a slow speed (500 rpm) for 10 min;
  • the amount of gas introduced into the base composition contributes to the adjustment in density of the whipped composition to the desired value.
  • the whipped composition of the invention may have a density less than 0.95 g/cm 3 , preferably a density ranging from 0.20 to 0.95 g/cm 3 , more preferably the density is less than 0.90 g/cm 3 , even more preferentially a density ranging from 0.30 to 0.90 g/cm 3 , in particular the density is less than 0.85 g/cm 3 , better ranging from 0.40 to 0.85 g/cm 3 , better still the density is less than 0.80 g/cm 3 , even better a density ranging from 0.50 to 0.80 g/cm 3 ; the density being measured at a temperature of 20°C and at atmospheric pressure ( l .0 l 3 x l 0 5 Pa), according to the following protocol.
  • the test is carried out on a composition volume of 25 ml, introduced into a 25 ml (Vi) smooth plexiglas® jar which defines a cylindrical filling space with a height of 15 mm and a base with a diameter of 46 mm.
  • the jar has a bottom wall 10 mm thick and a side wall 12 mm thick.
  • the composition to be characterized and the jar Prior to measurement, the composition to be characterized and the jar are maintained at a temperature of 20°C.
  • the jar is tared and the weight value is noted (Mi).
  • the whipped composition is subsequently introduced into the jar so as to occupy its total volume, while avoiding the formation of air bubbles during the filling of the jar.
  • the assembly is left to stand for 24 hours at 20°C.
  • the composition according to the invention comprises one or more gases, preferably in a content ranging from 1 % to 70%, in particular from 20% to 60%, and more particularly from 25 % to 40%, expressed by volume relative to the total volume of the whipped composition.
  • composition according to the invention does not come from an aerosol device or from any other pressurized container system, nor does it come from a non-pressurized device equipped with a foam generating dispensing system, that is to say that the gas(es) present in the composition according to the invention do not come from a gas or aerosol dispensing system, but are directly introduced into a base composition at ambient temperature and atmospheric pressure.
  • the base composition which serves to obtain the whipped composition according to the invention has a composition similar to the whipped composition, except for, on the one hand, its higher density since it is devoid of gas, in particular of air or inert gas, and on the other hand the higher fatty substance content.
  • the whipped composition according to the invention thus has the advantage of being very stable over time at ambient temperature and 45°C.
  • composition according to the invention comprises at least 20% by weight, relative to the total weight of the composition, of one or more fatty substances.
  • fatty substance is intended to mean an organic compound that is insoluble in water at ambient temperature (25°C) and at atmospheric pressure ( 1 .013 c 10 5 Pa), i.e. which has a solubility of less than 5% by weight, preferably less than 1 % by weight. They are generally soluble, under the same temperature and pressure conditions, in organic solvents such as chloroform, ethanol, benzene, liquid petroleum jelly or decamethylcyclopentasiloxane.
  • the fatty substance(s) are chosen from fatty substances that are liquid at 30°C and at atmospheric pressure ( 1 .013 10 5 Pa).
  • the fatty substance(s) of the composition according to the invention are non-silicone.
  • non-silicone fatty substance is intended to mean a fatty substance of which the structure does not comprise any silicon atoms, and which therefore especially does not comprise any siloxane groups. They generally bear in their structure a hydrocarbon-based chain comprising at least 6 carbon atoms. Advantageously, they are not oxyalkylenated and do not contain any -COOH functions.
  • the fatty substances that can be used in the invention preferably have a viscosity of less than or equal to 2 Pa.s, better still less than or equal to 1 Pa. s and even better still less than or equal to 0. 1 Pa.s at a temperature of 30°C and at a shear rate of 1 s 1 measured with a Rheomat RM 1800 (generally with spindle 1 or 2).
  • the fatty substances that can be used in the composition according to the invention may be chosen especially from liquid hydrocarbons, liquid fatty alcohols, liquid fatty esters and liquid fatty acids, and mixtures of these compounds.
  • liquid hydrocarbon is intended to mean a hydrocarbon composed solely o f carbon and hydrogen atoms, which is liquid at a temperature of 30°C and at atmospheric pressure (760 mmHg, i.e. 1 .013 c 10 5 Pa).
  • liquid hydrocarbons are chosen from:
  • C 6 -Ci 6 alkanes examples include hexane, undecane, dodecane, tridecane, and isoparaffins, for instance isohexadecane, isododecane and isodecane;
  • the liquid hydrocarbon(s) are chosen from liquid paraffins, isoparaffins, liquid petroleum jelly, undecane, tridecane and isododecane, and mixtures thereof.
  • liquid hydrocarbon(s) are chosen from liquid petroleum jelly, isoparaffins, isododecane and a mixture of undecane and tridecane.
  • liquid fatty alcohol is intended to mean a non-glycerolated and non- oxyalkylenated fatty alcohol, which is liquid at a temperature of 30°C and at atmospheric pressure (760 mmHg, i. e. 1 .013 c 10 5 Pa).
  • the liquid fatty alcohols of the invention comprise from 8 to 30 carbon atoms, especially from 10 to 24 carbon atoms, and may be saturated or unsaturated.
  • the saturated liquid fatty alcohols are preferably branched. They may optionally comprise in their structure at least one aromatic or non-aromatic ring, which is preferably acyclic.
  • saturated liquid fatty alcohols of the invention are chosen from octyldodecanol, 2-decyltetradecanol, isostearyl alcohol and 2-hexyldecanol.
  • Octyldodecanol and 2-decyltetradecanol are most particularly preferred.
  • the unsaturated liquid fatty alcohols contain in their structure at least one double or triple bond, and preferably one or more double bonds. When several double bonds are present, there are preferably 2 or 3 of them, and they may be conjugated or unconjugated.
  • These unsaturated fatty alcohols may be linear or branched.
  • They may optionally comprise in their structure at least one aromatic or non-aromatic ring. They are preferably acyclic.
  • the unsaturated liquid fatty alcohols that may be used in the invention are chosen from oleyl alcohol, linoleyl alcohol, linolenyl alcohol and undecylenyl alcohol.
  • Oleyl alcohol is most particularly preferred.
  • liquid fatty ester is intended to mean an ester derived from a fatty acid and/or from a fatty alcohol, which is liquid at a temperature of 30°C and at atmospheric pressure (760 mmHg, i.e. 1 .013 > ⁇ 10 5 Pa).
  • liquid esters are chosen from esters of saturated or unsaturated, linear or branched C1 -C26 aliphatic mono- or polyacids, which are optionally hydroxylated, and from saturated or unsaturated, linear or branched C1 -C26 aliphatic mono- or polyalcohols, the total number of carbon atoms in the esters being greater than or equal to 10.
  • the 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 invention are derived is branched.
  • the monoesters of monoacids and of monoalcohols mention may be made of alkyl palmitates, in particular of Ci -Ci s, especially ethyl palmitate and isopropyl palmitate, alkyl myristates in particular of Ci -Ci s, such as isopropyl myristate or ethyl myristate, alkyl stearates, in particular of Ci -Ci s, especially isocetyl stearate, 2- ethylhexyl isononanoate, isodecyl neopentanoate and isostearyl neopentanoate.
  • Esters of optionally hydroxylated C 3 -C 22 dicarboxylic or tricarboxylic acids and of C 1 -C 22 alcohols and esters of optionally hydroxylated monocarboxylic, dicarboxylic or tricarboxylic acids and of C 4 -C 26 dihydroxy, trihydroxy, tetrahydroxy or pentahydroxy non sugar alcohols may also be used.
  • esters mentioned above use is preferentially made of 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, propylene glycol dicaprylate, butyl stearate, isobutyl stearate; dioctyl malate, hexyl laurate, 2-hexyldecyl laurate, isononyl isononanoate, cetyl octanoate and bis(Ci 2 -Ci 3 )alkyl malate.
  • liquid fatty esters use may be made of sugar esters and diesters of C 6 - C 30 and preferably C12-C22 fatty acids.
  • sugar esters and diesters of C 6 - C 30 and preferably C12-C22 fatty acids.
  • the term “sugar” is intended to mean 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.
  • these said sugars are chosen from sucrose, 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 and fatty acid esters 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 C1 2-C22 fatty acids.
  • these compounds may comprise one to three conjugated or unconjugated carbon-carbon double bonds.
  • esters according to this variant may also be chosen from mono-, di-, tri- and tetraesters, and polyesters, and mixtures thereof.
  • esters may be, for example, oleates, laurates, palmitates, myristates, behenates, cocoates, stearates, linoleates, linolenates, caprates and arachidonates, and mixtures thereof, such as, especially, oleopalmitate, oleostearate or palmitostearate mixed esters.
  • Glucate® methylglucose dioleate
  • pentaerythrityl esters preferably pentaerythrityl tetraisostearate, pentaerythrityl tetraoctanoate, and caprylic and capric acid hexaesters as a mixture with dipentaerythritol.
  • said plant oil(s) or synthetic oil(s) are chosen from triglyceride oils of plant or synthetic origin, such as liquid fatty acid triglycerides containing from 6 to 30 carbon atoms, for instance heptanoic or octanoic acid triglycerides, or alternatively, for example, sesame oil, soybean oil, coffee oil, safflower oil, borage oil, sunflower oil, o live oil, apricot kernel oil, camellia oil, bambara pea oil, avocado oil, mango oil, rice bran oil, cottonseed oil, rose oil, kiwi seed oil, sea buckthorn pulp oil, blueberry seed oil, poppy seed oil, orange pip oil, sweet almond oil, palm oil, coconut oil (copra), vernonia oil, marjoram oil, baobab oil, rapeseed oil, ximenia oil, pracaxi oil, caprylic/capric acid triglycerides such as those sold by the company Stearineries
  • liquid esters that may be used according to the invention, use is preferably made of triglycerides of plant origin, in particular oils chosen from avocado oil, olive oil, camellia oil and apricot kernel oil, and mixtures thereof, and C4-C22 dicarboxylic or tricarboxylic acid esters of C1 -C22 alcohols, in particular 1 ,3 -propanediol dicaprylate.
  • oils chosen from avocado oil, olive oil, camellia oil and apricot kernel oil, and mixtures thereof
  • C4-C22 dicarboxylic or tricarboxylic acid esters of C1 -C22 alcohols in particular 1 ,3 -propanediol dicaprylate.
  • the composition according to the invention comprises at least one plant oil, as fatty substance.
  • fatty acid is intended to mean a non-salified fatty acid, i.e. the fatty acid must not be in the form of a generally soluble soap, i.e. it must not be salified with a base.
  • R is a C7-C29 alkyl or C7-C29 alkenyl group and better still a C1 2-C24 alkyl or C1 2-C24 alkenyl group.
  • R may be substituted with one or more hydroxyl groups and/or one or more carboxyl groups.
  • the liquid fatty acid(s) are chosen from oleic acid, linoleic acid and isostearic acid.
  • the composition according to the invention comprises one or more liquid fatty substances chosen from liquid hydrocarbons, liquid fatty esters and mixtures of these compounds, in particular chosen from those mentioned above.
  • the composition according to the invention comprises one or more fatty substances, more preferentially liquid fatty substances, chosen from linear or branched C 6 -Ci 6 alkanes, plant oils, in particular triglyceride oils, and a mixture of these compounds, and in particular chosen from undecane, tridecane, sunflower oil, shea oil, olive oil, avocado oil, jojoba oil, soybean oil, coconut oil (copra), rapeseed oil, and a mixture of these compounds.
  • fatty substances more preferentially liquid fatty substances, chosen from linear or branched C 6 -Ci 6 alkanes, plant oils, in particular triglyceride oils, and a mixture of these compounds, and in particular chosen from undecane, tridecane, sunflower oil, shea oil, olive oil, avocado oil, jojoba oil, soybean oil, coconut oil (copra), rapeseed oil, and a mixture of these compounds.
  • composition according to the invention comprises one or more liquid fatty substances in a content ranging from 20% to 80% by weight, preferably from 25% to 70% by weight and more preferentially from 30% to 60% by weight, or even from 40% to 55% by weight, relative to the total weight of the composition.
  • the composition according to the invention comprises one or more non-silicone liquid fatty substances in a content ranging from 20% to 80% by weight, more preferentially from 25 % to 70% by weight, and even more preferentially from 30% to 60% by weight, or even from 40% to 55% by weight, relative to the total weight of the composition.
  • the total content of fatty substances present in the composition according to the invention ranges from 20% to 80% by weight, more preferentially from 25% to 70% by weight, and even more preferentially from 30% to 60% by weight, or even from 40% to 55 % by weight, relative to the total weight of the composition.
  • composition according to the invention comprises one or more cationic surfactants.
  • cationic surfactant is intended to mean a surfactant that is positively charged when it is contained in the composition according to the invention. This surfactant may bear one or more positive permanent charges or may contain one or more cationizable functions in the composition according to the invention.
  • the cationic surfactant(s) are preferably chosen from primary, secondary or tertiary fatty amines, which are optionally polyoxyalkylenated, or salts thereof, and quaternary ammonium salts, and mixtures thereof.
  • the fatty amines generally comprise at least one C8-C30 hydrocarbon-based chain.
  • quaternary ammonium salts examples include:
  • the groups Ri to R 4 which may be identical or different, represent a linear or branched aliphatic group comprising from 1 to 30 carbon atoms, or an aromatic group such as aryl or alkylaryl, at least one of the groups Ri to R 4 denoting a linear or branched aliphatic radical comprising from 8 to 30 carbon atoms, preferably from 12 to 24 carbon atoms.
  • the aliphatic groups may comprise heteroatoms especially such as oxygen, nitrogen, sulfur and halogens.
  • the aliphatic groups are chosen, for example, from C 1 -C 30 alkyl, C1 -C 30 alkoxy, polyoxy(C 2 -C 6 )alkylene, C1 -C 30 alkylamide, (C i2-C22)alkylamido(C 2 -C6)alkyl, (Ci 2 -C 22 )alkyl acetate and C 1 -C 30 hydroxyalkyl groups;
  • X is an anion chosen from the group of the halides, phosphates, acetates, lactates, (Ci -C 4 )alkyl sulfates, (Ci - C 4 )alkyl- or (Ci -C 4 )alkylarylsulfonates.
  • quaternary ammonium salts of formula (I) are, on the one hand, tetraalkylammonium salts, for instance dialkyldimethylammonium or alkyltrimethylammonium salts in which the alkyl group comprises approximately from 12 to 22 carbon atoms, in particular behenyltrimethylammonium, distearyldimethylammonium, cetyltrimethylammonium or benzyldimethylstearylammonium salts, or, on the other hand, the palmitylamidopropyltrimethylammonium salts, the stearamidopropyltrimethylammonium salts, the stearamidopropyldimethylcetearylammonium salts, or the stearamidopropyldimethyl(myristyl acetate)ammonium salts sold under the name Ceraphyl® 70 by the company Van Dyk. It is preferred in particular to use the chloride salts of these compounds.
  • R 5 represents an alkenyl or alkyl group comprising from 8 to 30 carbon atoms, for example derived from tallow fatty acids
  • R 6 represents a hydrogen atom, a Ci -C 4 alkyl group or an alkenyl or alkyl group comprising from 8 to 30 carbon atoms
  • R 7 represents a Ci - C 4 alkyl group
  • R 8 represents a hydrogen atom or a Ci -C 4 alkyl group
  • X is an anion chosen from the group of the halides, phosphates, acetates, lactates, alkyl sulfates, alkylsulfonates or alkylarylsulfonates, the alkyl and aryl groups of which preferably comprise, respectively, from 1 to 20 carbon atoms and from 6 to 30 carbon atoms.
  • Rs and R 6 denote a mixture of alkenyl or alkyl groups comprising from 12 to 21 carbon atoms, for example derived from tallow fatty acids, R 7 denotes a methyl group and Rs denotes a hydrogen atom.
  • R 7 denotes a methyl group and Rs denotes a hydrogen atom.
  • R9 denotes an alkyl radical comprising approximately from 16 to 30 carbon atoms, which is optionally hydroxylated and/or optionally interrupted with one or more oxygen atoms
  • Rio is chosen from hydrogen or an alkyl radical comprising from 1 to 4 carbon atoms or a group (R9a)(Rio a )(Ri ia)N-(CH 2 ) 3 ,
  • R9a, Ri oa, Ri i a, Rn , R1 2, R1 3 and R1 4, which may be identical or different, are chosen from hydrogen or an alkyl radical comprising from 1 to 4 carbon atoms
  • X is an anion chosen from the group of halides, acetates, phosphates, nitrates, (Ci -C4)alkyl sulfates, (Ci - C4)alkyl sulfonates and (Ci -C4)alkylaryl sulfonates, and in particular methyl sulfate and ethyl sulfate.
  • Such compounds are, for example, Finquat CT-P, sold by the company Finetex (Quaternium 89), and Finquat CT, sold by the company Finetex (Quaternium 75),
  • R1 5 is chosen from C i -C 6 alkyl groups and C i -C 6 hydroxyalkyl or dihydroxyalkyl groups;
  • Ri 6 is chosen from:
  • R 20 which are linear or branched, saturated or unsaturated C 1 -C 22 hydrocarbon-based groups, - a hydrogen atom,
  • Ri 8 is chosen from: o I I
  • R1 7, R1 9 and R2 1 which may be identical or different, are chosen from linear or branched, saturated or unsaturated C7-C2 1 hydrocarbon-based groups;
  • r, s and t which may be identical or different, are integers ranging from 2 to 6;
  • y is an integer ranging from 1 to 10;
  • x and z which may be identical or different, are integers ranging from 0 to 10;
  • X is a simple or complex, organic or mineral anion
  • the alkyl groups R1 5 may be linear or branched, and more particularly linear.
  • R1 5 denotes a methyl, ethyl, hydroxyethyl or dihydroxypropyl group, and more particularly a methyl or ethyl group.
  • the sum x + y + z is from 1 to 10.
  • R i 6 is a hydrocarbon-based group R20 , it may be long and contain from 12 to 22 carbon atoms, or may be short and contain from 1 to 3 carbon atoms.
  • R i 8 is a hydrocarbon-based group R22 , it preferably contains 1 to 3 carbon atoms.
  • R 1 7 , R 1 9 and R2 1 which may be identical or different, are chosen from linear or branched, saturated or unsaturated C1 1 -C2 1 hydrocarbon-based groups, and more particularly from linear or branched, saturated or unsaturated C1 1 -C2 1 alkyl and alkenyl groups.
  • x and z which may be identical or different, are equal to 0 or 1 .
  • y is equal to 1 .
  • r, s and t which may be identical or different, are equal to 2 or 3 , and even more particularly are equal to 2.
  • the anion X is preferably a halide (chloride, bromide or iodide) or an alkyl sulfate, more particularly methyl sulfate.
  • halide chloride, bromide or iodide
  • alkyl sulfate more particularly methyl sulfate.
  • methanesulfonate, phosphate, nitrate, tosylate an anion derived from an organic acid, such as acetate or lactate, or any other anion that is compatible with the ammonium bearing an ester function.
  • the anion X is even more particularly chloride or methyl sulfate.
  • R1 5 denotes a methyl or ethyl group
  • x and y are equal to 1 ;
  • z is equal to 0 or 1 ;
  • r, s and t are equal to 2;
  • Ri 6 is chosen from:
  • Ri 8 is chosen from:
  • R 1 7 , R 1 9 and R 2 1 which may be identical or different, are chosen from linear or branched, saturated or unsaturated C 1 3 -C 1 7 hydrocarbon-based groups, and preferably from linear or branched, saturated or unsaturated C 13 -C 17 alkyl and alkenyl groups.
  • the hydrocarbon-based groups are linear.
  • Examples that may be mentioned include the compounds of formula (IV) such as the diacyloxyethyldimethylammonium, diacyloxyethylhydroxyethylmethylammonium,
  • acyl groups preferably contain from 14 to 18 carbon atoms and are derived more particularly from a plant oil such as palm oil or sunflower oil. When the compound contains several acyl groups, these groups may be identical or different.
  • These products are obtained, for example, by direct esterification of triethanolamine, triisopropanolamine, an alkyldiethanolamine or an alkyldiisopropanolamine, which are optionally oxyalkylenated, with C1 0-C30 fatty acids or with mixtures of C1 0-C30 fatty acids of plant or animal origin, or by transesterification of the methyl esters thereof.
  • This esterification is followed by a quaternization using an alkylating agent such as an alkyl halide (preferably a methyl or ethyl halide), a dialkyl sulfate (preferably a methyl or ethyl sulfate), methyl methanesulfonate, methyl para- toluenesulfonate, glycol chlorohydrin or glycerol chlorohydrin.
  • an alkylating agent such as an alkyl halide (preferably a methyl or ethyl halide), a dialkyl sulfate (preferably a methyl or ethyl sulfate), methyl methanesulfonate, methyl para- toluenesulfonate, glycol chlorohydrin or glycerol chlorohydrin.
  • composition according to the invention may contain, for example, a mixture of quaternary ammonium monoester, diester and triester salts with a weight majority of diester salts.
  • Use may also be made of the ammonium salts containing at least one ester function that are described in patents US-A-4 874 554 and US-A-4 137 1 80. Use may be made of behenoylhydroxypropyltrimethylammonium chloride sold by KAO under the name Quatarmin BTC 13 1 .
  • the ammonium salts containing at least one ester function contain two ester functions.
  • quaternary ammonium salts containing at least one ester function which may be used, it is preferred to use dipalmitoyl- ethylhydroxyethylmethylammonium salts.
  • the cationic surfactant(s) are preferably chosen from those of formula (I) and those of formula (IV) and even more preferentially from those of formula (I).
  • the cationic surfactant(s) that may be used according to the invention are chosen from those of formula (I), more preferentially from behenyltrimethylammonium salts, cetyltrimethylammonium salts, and a mixture of these compounds, and even more preferentially from behenyltrimethylammonium chloride, cetyltrimethylammonium chloride, and a mixture of these compounds.
  • the cationic surfactant(s) that can be used in the composition according to the invention are chosen from the cationic surfactants of formula (I).
  • the cationic surfactant(s) of the composition according to the invention advantageously represent from 0.01 % to 10% by weight, preferably from 0. 1 % to 8% by weight and more preferentially from 1 % to 5% by weight relative to the total weight of the composition.
  • composition according to the invention may also comprise one or more polyols.
  • polyol is intended to mean an organic compound constituted of a hydrocarbon- based chain optionally interrupted with one or more oxygen atoms and bearing at least two free hydroxyl groups (-OH) borne by different carbon atoms, this compound possibly being cyclic or acyclic, linear or branched, and saturated or unsaturated.
  • the polyol(s) that may be used according to the invention comprise from 2 to 30 hydroxyl groups, more preferentially from 2 to 10 hydroxyl groups and even more preferentially from 2 to 3 hydroxyl groups.
  • the polyol(s) that may be used according to the invention generally comprise at least three carbon atoms.
  • said polyol(s) that may be used according to the invention are chosen from polyols comprising at least three carbon atoms and ethylene glycol, and are preferably chosen from 1 ,3- propanediol, 1 , 3-butylene glycol, 1 ,2-pentanediol, dipropylene glycol, hexylene glycol, pentylene glycol, glycerol, ethylene glycol and sorbitol, and a mixture of these compounds.
  • the polyol(s) that can be used according to the invention are chosen from glycerol, sorbitol or a mixture of these compounds, and preferably the polyol is glycerol.
  • composition according to the invention does not comprise propylene glycol.
  • the polyol(s) represent from 0.5% to 20% by weight, better still from 1 % to 15% by weight and more preferentially from 2% to 10% by weight, relative to the total weight of the composition.
  • composition according to the invention comprises water.
  • Water advantageously represents from 5 % to 60% by weight, preferably from 10% to 50% by weight and more preferentially from 15% to 40% by weight relative to the total weight of the composition.
  • composition according to the invention may also comprise one or more organic solvents other than polyols.
  • the organic solvent(s) other than polyols are chosen from non-aromatic Ci -C 6 alcohols such as ethyl alcohol or isopropyl alcohol, or aromatic alcohols such as benzyl alcohol and phenylethyl alcohol.
  • the composition according to the invention comprises one or more organic solvents other than polyols, the organic solvent preferably being ethanol.
  • the organic solvent(s) other than polyols generally represent from 0. 1 % to 15% by weight and preferably from 0.5% to 10% by weight relative to the total weight of the composition.
  • the pH of the composition of the invention is generally between 3 and 8, preferably between 4 and 7, better still between 4.5 and 6.
  • the pH of the composition according to the invention may be adjusted to the desired value by means of acidifying or basifying agents usually used in cosmetic compositions, or alternatively using standard buffer systems.
  • acidifying agents examples that may be mentioned include mineral acids, for instance hydrochloric acid,
  • (ortho)phosphoric acid boric acid, nitric acid or sulfuric acid, or organic acids, for instance compounds comprising at least one carboxylic acid function such as acetic acid, tartaric acid, citric acid or lactic acid, a sulfonic acid function, a phosphonic acid function or a phosphoric acid function.
  • carboxylic acid function such as acetic acid, tartaric acid, citric acid or lactic acid, a sulfonic acid function, a phosphonic acid function or a phosphoric acid function.
  • phosphoric acid is used as acidifying agent.
  • the basifying agent(s) may be mineral, organic or hybrid.
  • the mineral alkaline agent(s) are preferably chosen from aqueous ammonia, alkali metal carbonates or bicarbonates such as sodium carbonate or bicarbonate, potassium carbonate or bicarbonate, sodium hydroxide or potassium hydroxide or mixtures thereof.
  • the organic alkaline agent(s) are preferably chosen from organic amines with a pK b at 25°C of less than 12, preferably of less than 10 and even more advantageously of less than 6. It should be noted that it is the pK b corresponding to the function of highest basicity.
  • the organic amines do not comprise any alkyl or alkenyl fatty chain comprising more than ten carbon atoms.
  • the organic alkaline agent(s) are chosen, for example, from alkanolamines, oxyethylenated and/or oxypropylenated ethylenediamines, amino acids and the compounds of formula (V) below: in which W is a divalent Ci to C 6 alkylene radical optionally substituted with one or more hydroxyl groups or a Ci to C 6 alkyl radical, and/or optionally interrupted with one or more heteroatoms such as O, or NR U ; R x , R y , Rz, Rt and R u , which may be identical or different, represent a hydrogen atom or a Ci to C 6 alkyl, Ci to C 6 hydroxyalkyl or Ci to C 6 aminoalkyl radical.
  • amines of formula (V) examples include 1 ,3-diaminopropane, 1 ,3-diamino-2-propanol, spermine and spermidine.
  • composition according to the invention may also comprise one or more additives.
  • additives that may be used in accordance with the invention, mention may be made of antidandruff agents, anti-seborrhoea agents, agents for preventing hair loss and/or for promoting hair regrowth, vitamins and provitamins including panthenol, sunscreens, mineral or organic pigments, sequestrants, plasticizers, solubilizers, opacifiers or pearlescent agents, antioxidants, fragrances, preservatives and pigments.
  • antidandruff agents include panthenol, sunscreens, mineral or organic pigments, sequestrants, plasticizers, solubilizers, opacifiers or pearlescent agents, antioxidants, fragrances, preservatives and pigments.
  • additives may be present in the composition according to the invention in an amount ranging from 0 to 50% by weight, relative to the total weight of the composition.
  • the composition according to the invention is in the form of an oil-in-water nanoemulsion of which the particles (or drops) of oil preferably have a volume-average size of less than 500 nm, preferentially of between 10 and 300 nm, and better still between 20 and 250 nm, and even better still between 25 and 200 nm.
  • the volume-average size of the particles (or oil drops) may be determined in particular according to the known laser diffraction method.
  • the particle size analyser of the brand Malvern, model Zetasizer Nano ZS, equipped with a standard laser having a power of 4 mW, and at a wavelength of 633 nm.
  • This device is also equipped with a correlator (25 ns to 8000 s, 4000 channels maxi.).
  • composition according to the invention has very low polydispersity, i.e. the particles have a very homogeneous size.
  • the particles present in the composition according to the invention are liquid oil (or oily phase) particles within the continuous aqueous phase.
  • composition according to the invention is generally prepared by means of a piece of equipment of whipping machine type which makes it possible to combine a stream of gas with that of a base composition in the form of a nanoemulsion through a dispersing tool.
  • the whipped texture of the composition according to the invention is thus obtained.
  • composition according to the invention can be obtained in the following way:
  • the process for preparing the whipped composition according to the invention comprises (i) at least one step of preparing the base composition containing at least 20% by weight of fatty substance relative to the total weight of the composition and (ii) at least one step of introducing one or more gases into said composition by means of a piece of equipment of whipping machine type making it possible in particular to provide the abovementioned stirring and the gas inlet pressure.
  • the gas can be introduced into the nanoemulsion by means of an equipment of whipping machine type comprising a mixing head comprising a rotor and a stator, for instance the Mondomixer device of Minimondo type supplied by the company Mondomix.
  • an equipment of whipping machine type comprising a mixing head comprising a rotor and a stator, for instance the Mondomixer device of Minimondo type supplied by the company Mondomix.
  • equipment of whipping machine type it is generally meant equipment comprising as major element, a mixing chamber consisting o f a static part, provided with a double envelope resistant to a pressure o f up to 5 bar (ie 5. 10 5 Pa), and a dynamic part (rotor type) which can have a speed ranging from 100 to 1500 revolutions / minute (rpm).
  • the nanoemulsion is transported by a pump into the whipping head, where the nanoemulsion and the gas are simultaneously injected and homogeneously mixed by virtue of the cutting action of the lugs o f the rotor and of the stator of the device, which ensure an equal distribution of the gas in the product.
  • the speed of the rotor of the device, the temperature of the tank and of the pipes and also the gas inlet pressure in the mixing head and the airflow rate are regulated appropriately.
  • the pressure of the mixing head is regulated by a pressure regulator.
  • the flow rate of the nanoemulsion at the outlet of the device depends on the frequency of the pump at the tank outlet.
  • the stirring speed during the introduction of the gas may in particular be 1000 rpm, the temperature from 25 °C to 50°C and the gas inlet pressure in the mixing chamber from 2 to 4 bars (ie of 2. 10 5 to 4. 10 5 Pa).
  • composition according to the invention is advantageously in the form of a foam.
  • the composition has a translucent to blueish colour, preferably a blueish colour, when spread in a thin layer.
  • composition according to the invention may have a viscosity ranging for example from 1 to 500 mPa.s (1 to 500 cPoises), and preferably from 1 to 200 mPa.s ( 1 to 200 cPoises), the viscosity being measured at ambient temperature (25°C) with a Rheomat RM 180 (generally using spindle 1 or 2).
  • the invention also relates to a process for the cosmetic treatment of keratin materials, in particular keratin fibres, preferably human keratin fibres such as the hair, in which the composition according to the invention is applied to said materials.
  • an effective quantity of the composition may be applied to the keratin materials, followed by an optional rinse after an optional leave-on time.
  • the treatment process comprises a rinsing step after the application of the composition according to the invention.
  • the invention also relates to the use of the composition according to the invention for the cosmetic treatment of keratin materials, in particular keratin fibres, preferably human keratin fibres such as the hair.
  • compositions according to the invention may be used, for example, as a cleaning composition, such as a pre-treatment or post treatment composition for shampoos, dyes, permanent waves, bleaches and straighteners.
  • a cleaning composition such as a pre-treatment or post treatment composition for shampoos, dyes, permanent waves, bleaches and straighteners.
  • the composition according to the invention is a rinse-off or leave-on conditioner care product.
  • composition according to the invention is a rinse-off conditioner care product.
  • the amounts are indicated as weight percentages of compound active material (MA) relative to the total weight of the composition, and the densities of the compositions have been measured according to the method as defined in the description above.
  • the granulometries have been measured according to a standard method using the particle size analyser of the brand Malvern, model Zetasizer Nano ZS, equipped with a standard laser having a power of 4 mW, and at a wavelength of 633 nm.
  • This device is also equipped with a correlator (25 ns to 8000 s, 4000 channels maxi.).
  • composition A is prepared according to the conventional methods:
  • composition A 70 ml of the composition A are mixed with 30 ml of compressed air by means of an equipment of whipping machine type, in particular the Mondomixer device of Minimondo type supplied by the company Mondomix, to form the whipped composition B according to the invention.
  • an equipment of whipping machine type in particular the Mondomixer device of Minimondo type supplied by the company Mondomix, to form the whipped composition B according to the invention.
  • the whipped composition B according to the invention has the appearance of a creamy, aerated composition (of chocolate mousse type).
  • composition A is equal to 0.92
  • density of whipped composition B is equal to 0.69.
  • composition B The stability of the composition B was evaluated visually: directly after its preparation (To) and after 2 months of storage at atmospheric pressure (To + 2 months), at room temperature (25°C) and at 45°C.
  • composition B according to the invention exhibits good stability over time, both at ambient temperature (25°C) and at a higher temperature of 45°C .

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Abstract

La présente invention concerne une composition cosmétique fouettée sous la forme d'une nanoémulsion huile-dans-eau comprenant (i) une ou plusieurs substances grasses liquides dans une teneur allant de 20 % à 80 % en poids par rapport au poids total de la composition, (ii) un ou plusieurs tensioactifs cationiques, (iii) un ou plusieurs gaz et (iv) de l'eau. L'invention a également pour objet un procédé de traitement cosmétique des matières kératiniques, en particulier des fibres kératiniques, de préférence des fibres kératiniques humaines telles que les cheveux, dans lequel la composition est appliquée sur lesdites matières. Enfin, l'invention concerne l'utilisation de la composition telle que définie ci-dessus pour le traitement cosmétique de matières kératiniques, en particulier des fibres kératiniques, de préférence des fibres kératiniques humaines telles que les cheveux.
PCT/EP2018/086485 2017-12-29 2018-12-21 Composition cosmétique fouettée sous la forme d'une nanoémulsion comprenant au moins 20 % de substance grasse, au moins un tensioactif cationique, un gaz et de l'eau WO2019129683A1 (fr)

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FR1763396A FR3076215B1 (fr) 2017-12-29 2017-12-29 Composition cosmetique foisonnee sous forme d'une nanoemulsion comprenant au moins 20% de corps gras, au moins un tensioactif cationique, un gaz et de l'eau

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Cited By (1)

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Publication number Priority date Publication date Assignee Title
US11357714B2 (en) 2020-07-21 2022-06-14 Chembeau LLC Diester cosmetic formulations and uses thereof

Citations (7)

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Publication number Priority date Publication date Assignee Title
US4137180A (en) 1976-07-02 1979-01-30 Lever Brothers Company Fabric treatment materials
US4874554A (en) 1986-07-10 1989-10-17 Henkel Kommanditgesellschaft Auf Aktien Quaternary ammonium compounds
FR2760970A1 (fr) * 1997-03-18 1998-09-25 Oreal Nanoemulsions a base de lipides amphiphiles non-ioniques et de silicones aminees et utilisations
EP1120101A2 (fr) * 2000-01-21 2001-08-01 L'oreal Nanoémulsion contenant des lipides amphiphiles et un ester de PEG et utilisation en cosmétologie
EP1120102A2 (fr) * 2000-01-21 2001-08-01 L'oreal Nanoémulsion contenant des lipides amphiphiles et un polymère non ionique et utilisation en cosmétologie
EP1129684A2 (fr) * 2000-01-21 2001-09-05 L'oreal Nanoémulsion à base de lipides amphiphiles et de polymères cationiques et utilisation en cosmétologie
US20150359728A1 (en) 2014-06-16 2015-12-17 The Procter & Gamble Company Method of Treating Hair with a Concentrated Conditioner

Patent Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4137180A (en) 1976-07-02 1979-01-30 Lever Brothers Company Fabric treatment materials
US4874554A (en) 1986-07-10 1989-10-17 Henkel Kommanditgesellschaft Auf Aktien Quaternary ammonium compounds
FR2760970A1 (fr) * 1997-03-18 1998-09-25 Oreal Nanoemulsions a base de lipides amphiphiles non-ioniques et de silicones aminees et utilisations
EP1120101A2 (fr) * 2000-01-21 2001-08-01 L'oreal Nanoémulsion contenant des lipides amphiphiles et un ester de PEG et utilisation en cosmétologie
EP1120102A2 (fr) * 2000-01-21 2001-08-01 L'oreal Nanoémulsion contenant des lipides amphiphiles et un polymère non ionique et utilisation en cosmétologie
EP1129684A2 (fr) * 2000-01-21 2001-09-05 L'oreal Nanoémulsion à base de lipides amphiphiles et de polymères cationiques et utilisation en cosmétologie
US20150359728A1 (en) 2014-06-16 2015-12-17 The Procter & Gamble Company Method of Treating Hair with a Concentrated Conditioner

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
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

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