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WO2025078046A1 - Emulsion e/h fluide comprenant un polyester particulier, un alcane volatil, au moins 50% de composant(s) liquide(s) de la phase aqueuse, et un tensioactif non ionique polyhydroxystéarique et/ou polyricinoléique - Google Patents

Emulsion e/h fluide comprenant un polyester particulier, un alcane volatil, au moins 50% de composant(s) liquide(s) de la phase aqueuse, et un tensioactif non ionique polyhydroxystéarique et/ou polyricinoléique Download PDF

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Publication number
WO2025078046A1
WO2025078046A1 PCT/EP2024/068758 EP2024068758W WO2025078046A1 WO 2025078046 A1 WO2025078046 A1 WO 2025078046A1 EP 2024068758 W EP2024068758 W EP 2024068758W WO 2025078046 A1 WO2025078046 A1 WO 2025078046A1
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weight
acid
polyglycerol
composition according
polyester
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Inventor
Nathalie GUILLIER
Boris COUTIN
Pascal Arnaud
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LOreal SA
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LOreal SA
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    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/02—Cosmetics or similar toiletry preparations characterised by special physical form
    • A61K8/04—Dispersions; Emulsions
    • A61K8/06—Emulsions
    • A61K8/064—Water-in-oil emulsions, e.g. Water-in-silicone 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
    • A61K8/39—Derivatives containing from 2 to 10 oxyalkylene groups
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
    • A61K8/84—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions otherwise than those involving only carbon-carbon unsaturated bonds
    • A61K8/85—Polyesters
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q1/00—Make-up preparations; Body powders; Preparations for removing make-up
    • A61Q1/02—Preparations containing skin colorants, e.g. pigments

Definitions

  • the present invention aims to propose, for the field of caring for and/or making up keratin materials, in particular the skin, lips, eyelashes or eyebrows, a fluid composition in the form of a water-in-oil emulsion comprising at least one particular polyester, at least one volatile hydrocarbon oil, at least 50% by weight of liquid component(s) of the aqueous phase, relative to the total weight of the composition, and at least one non-ionic surfactant with an HLB ⁇ 8.0, the chemical structure of which results from the reaction of at least one polyhydroxystearic acid and/or at least one polyricinoleic acid with a polyol containing at least two alcohol functions.
  • compositions for caring for and/or making up keratin materials may be in the form of numerous textures which condition their sensory properties. Mention may be made, for example, of oily or aqueous textures, gels, creams, foams, powders or sticks. These textures are more or less liquid or solid.
  • liquid textures are valued because they are light and easy to apply, and they also allow a more homogeneous distribution of pigments and pearlescent agents.
  • Emulsions may be defined as being heterogeneous systems comprising at least two liquid phases that are immiscible or that are very sparingly miscible with one another.
  • one of the phases is dispersed in the form of fine droplets in the other phase, so as to observe a mixture that is macroscopically homogeneous to the naked eye.
  • the formulator of cosmetic compositions uses emulsified systems that combine an aqueous phase for freshness and a fatty phase for comfort.
  • compositions of the inverse emulsion type have numerous advantages, with regard to the good level of coverage and the homogeneous appearance that they provide compared with direct emulsions (oil-in-water emulsions).
  • Their weak point is, on the other hand, that they give a pronounced greasy and tacky feeling, and thus a lack of lightness for the textures obtained.
  • HIPE High Internal Phase Emulsion
  • HIPE inverse emulsions have the drawback of increasing the viscosity because of the large amount of water.
  • water-in-oil emulsions intended for makeup most often contain synthetic film-forming polymers which provide wear properties, but which themselves also tend to increase the viscosity of the product, especially when they are present in the continuous oily phase.
  • polyesters obtained by condensation of dimer and/or trimer of an unsaturated fatty acid and of a diol is a polyester of dilinoleic acid and of 1,4-butanediol, such as the polymer sold by Biosynthis under the name Viscoplast 14436H® (INCI name: Dilinoleic Acid/Butanediol Copolymer).
  • polyesters of hydroxylated fatty acid triglyceride and of a saturated fatty diacid for providing the wear property to makeup compositions. Mention may in particular be made, by way of examples of polyesters, of those with the INCI name Hydrogenated Castor Oil/Sebacic Acid Copolymer, such as the product sold under the name Crodabond CSA® by Croda, and also the hydrogenated castor oil dimer dilinoleate with the INCI name: Hydrogenated Castor Oil Dimer Dilinoleate, such as the product sold under the names Risocast-DA-L® and Risocast DA-H® by Kokyu Alcohol Kogyo.
  • Patent application US2021/0259930A1 by Nouryon Chemicals discloses water-resistant, water-in-oil emulsions comprising at least one polyester which is the reaction product of the following components (i), (ii) and (iii): (i) at least one polyglycerol-3; (ii) at least one dimer acid; and (iii) at least one fatty monoacid having from 8 to 30 carbon atoms, the components (i), (ii) and (iii) reacted being in a molar ratio of 1 mole of polyglycerol-3, of 0.5 to 1 mole of dimer acid and of 0.1 to less than 2.0 moles of fatty monoacid and at least one water-in-oil emulsifier.
  • the single example of formulation comprises - 4% by weight of Tri(Polyglyceryl-3/Lauryl) Hydrogenated Trilinoleate sold under the trade reference Cithrol PGTL® by Croda, - 1.66% by weight of a mixture of 60% by weight of polyester and 40% by weight of Caprylic/Capric Triglyceride, i.e. 1% of polymer; - 44.62% by weight of liquid components of the aqueous phase.
  • the term “fluid product” means any composition having a viscosity at 25°C of less than or equal to 1500 mPa.s (1500 centipoise), measured using an RM 200® rotary rheometer from Lamy Rheology Instruments, after 10 minutes of rotation of spindle 3 at a speed of 200 rpm. After production, the samples are stored for 24 to 72 hours at ambient temperature (25°C). The viscosities are measured at a temperature of 25°C, kept constant by means of an EVA MS-R® temperature controller from Lamy Rheology Instruments.
  • a fluid water-in-oil emulsion for caring for and/or making up keratin materials such as the skin, the lips, the contour of the eyes, the eyelids, the eyelashes and the eyebrows, comprising, in particular, in a physiologically acceptable medium:
  • B) at least one continuous oily phase comprising: 1) at least one volatile hydrocarbon oil; and 2)
  • compositions according to the invention in the form of HIPE inverse emulsion are stable, have a fluid texture and have good wear properties.
  • the applicant has discovered, unexpectedly, that the combination of at least one polyester A) with at least one non-ionic surfactant D), as defined above, in the compositions according to the invention produces, after application to the keratin material, a notable sensation of softness to the touch.
  • the present invention relates to a fluid water-in-oil emulsion for caring for and/or making up keratin materials such as the skin, the lips, the contour of the eyes, the eyelids, the eyelashes and the eyebrows, comprising, in particular in a physiologically acceptable medium:
  • B) at least one continuous oily phase comprising: 1) at least one volatile hydrocarbon oil; and 2) optionally at least one non-vol
  • the invention also relates to a method for coating keratin materials, more particularly for making up and/or caring for keratin materials, such as the skin, the contour of the eyes, the eyelids, the eyelashes and the eyebrows, characterized in that it comprises at least the application to keratin materials of a composition as defined above.
  • the invention also relates to the use of at least one polyester A) and of at least one non-ionic surfactant D), as defined above, in a water-in-oil emulsion comprising at least 50% by weight of liquid component(s) of the aqueous phase relative to the total weight of the composition and at least one volatile hydrocarbon oil in the oily phase, in order to provide a soft feel after application.
  • keratin material is understood to mean in particular the skin, the lips, the contour of the eyes, the eyelids, the eyelashes and the eyebrows.
  • physiologically acceptable is understood to mean compatible with the skin, the lips, the contour of the eyes, the eyelids, the eyelashes and the eyebrows, having a pleasant colour, odour and feel and not generating unacceptable discomfort (tingling, tautness) likely to discourage the consumer from using this composition.
  • polyester is understood to mean any polymer obtained by a condensation reaction of polycarboxylic acids with alcohols or glycols. Its macromolecular backbone contains the repetition of its ester function.
  • the ester function denotes a characteristic group formed of an atom bonded simultaneously to an oxygen atom by a double bond and to an alkoxy group.
  • the bonded atom is a carbon atom, it is called a carboxylic ester, the general form of which is R-COO-R'.
  • polyglycerol-3 is understood to mean triglycerol alone or a mixture of polyglycerols comprising at least triglycerol, and preferably triglycerol is predominant in said mixture.
  • water-in-oil emulsion also known as inverse emulsion
  • inverse emulsion any composition constituted of a continuous oily phase in which the aqueous phase is dispersed in the form of droplets so as to observe a mixture which is macroscopically homogeneous to the naked eye.
  • liquid component of the aqueous phase is understood to mean any molecule present in the phase and which flows under its own weight at ambient temperature (20-25°C) and at atmospheric pressure (760 mmHg or 1.013 ⁇ 10 5 Pa).
  • the composition in accordance with the invention comprises at least one polyester which is the reaction product of the following components (i), (ii) and (iii): (i) at least one polyglycerol-3; (ii) at least one dimer acid; and (iii) at least one fatty monoacid having from 8 to 30 carbon atoms, the components (i), (ii) and (iii) reacted being in a molar ratio of 1 mole of polyglycerol-3, of 0.5 to 1 mole of dimer acid and of 0.1 to less than 2.0 moles of fatty monoacid.
  • polyesters of the invention are described in the patent applications US 2021/0259945, US 2021/0259946 and US 2021/0259930.
  • the amount, as active material, of polyester varies from 1% to 20% by weight, more preferentially from 2% to 8% by weight, relative to the total weight of the composition.
  • the polyester is a substantially or completely non-sequential reaction product.
  • product of substantially non-sequential reaction means the product obtained by a substantially non-sequential reaction of the reactive components (i)-(iii).
  • totally non-sequential reaction of the reactive components (i)-(iii) means that the total content of each of the reagents (i)-(iii) to be reacted is added to the reaction vessel before starting the reaction.
  • the total content of each of the reagents (i)-(iii) to be reacted is added to the reaction vessel before starting the reaction, that is to say that the reaction is totally non-sequential, and the polymer is a product of totally non-sequential reaction of the components (i)-(iii).
  • 70-100%, or 75-100%, or 80-100%, or 85-100%, or 90-100%, or 95-100%, or 97-100% of each of the reagents (i)-(iii) are added to the reaction vessel before starting the reaction.
  • the polyester is prepared by a one-step process which involves the introduction of all the reagents into a reaction vessel and subsequently the induction of an entirely random addition of the dimer acid and of the isostearic acid to the polyglycerol-3.
  • Triglycerol has the formula H-[-OGly] 3 -OH in which Gly designates a glycerol residue after removal of two hydroxyl groups.
  • a polyglycerol-3 according to the invention in the form of a mixture of polyglycerols containing at least triglycerol comprises polyglycerols which can be any product of oligocondensation of glycerol. They preferably correspond to the formula (I): [Chem 1]
  • each Gly is independently the residue of a glycerol molecule after removal of two hydroxyl groups; and n is a mean from 2 to 10.
  • Gly the majority of the Gly groups are of the formula: -CH 2 -CHOH-CH 2 -, although the residues comprising etherification at secondary or even tertiary hydroxyl groups are regarded as being within the scope of “Gly” and, consequently, may also be present.
  • polyglycerol-3 examples comprise diglycerol, triglycerol, tetraglycerol, pentaglycerol, hexaglycerol, heptaglycerol, octaglycerol, nonaglycerol, decaglycerol and mixtures of these.
  • preferential polyglycerols are those of formula (I) in which n in particular has a value from 2 to 7, more particularly from 2 to 5 and in particular 2, 3 or 4, or mixtures of oligoglycerols in these ranges.
  • polyglycerol-3 comprise a mixture of polyglycerols having the following distribution, in which all the percentages by weight are based relative to the total weight of the polyglycerol-3 in the form of a mixture: - glycerol: from 0% to 30% by weight, preferably from 0% to 20% by weight, particularly preferably from 0% to 15% by weight; - diglycerol: from 10% to 40% by weight, preferably from 15% to 35% by weight, particularly preferably from 20% to 32% by weight; - triglycerol: from 10% to 65% by weight, preferably from 15% to 60% by weight, particularly preferably from 18% to 55% by weight; - tetraglycerol: from 2% to 25% by weight, preferably from 5% to 20% by weight, particularly preferably from 8% to 20% by weight; - pentaglycerol: from 0% to 15% by weight, preferably from 0% to 10% by weight, particularly preferably from 0% to 5% by weight; - hexaglycerol
  • a polyglycerol-3 in the form of a mixture comprises the following distribution of polyglycerols: Glycerol: from 0% to 30% by weight; Diglycerol: from 15% to 40% by weight; Triglycerol: from 10% to 55% by weight; Tetraglycerol: from 2% to 25% by weight; Pentaglycerol and higher components: from 0% to 15% by weight, relative to the total weight of the polyglycerol-3 in the form of a mixture.
  • a polyglycerol-3 in the form of a mixture is composed of at least 40% by weight, or of at least 45% by weight, or of at least 50% by weight, of a combination of diglycerol and of triglycerol, relative to the total weight of the polyglycerol-3 in the form of a mixture.
  • a polyglycerol-3 in the form of a mixture is composed of at least 20% by weight, or of at least 25% by weight, of diglycerol; at least 15% by weight, or at least 18% by weight, of triglycerol; at least 10% by weight, or at least 12% by weight, of tetraglycerol; in which all the percentages by weight are relative to the total weight of the polyglycerol-3 in the form of a mixture.
  • a particularly preferred polyglycerol-3 in the form of a mixture comprises at least 25% by weight of diglycerol, at least 45% by weight of triglycerol and at least 10% by weight of tetraglycerol, relative to the total weight of the polyglycerol-3 in the form of a mixture.
  • polyglycerol-3 The analysis of such a polyglycerol-3 composition can be carried out in order to determine its median or “mean” polyglycerol number.
  • the examples of polyglycerols above with narrow and broad distributions can also be denoted as polyglycerol-3 because it is a matter of the integer closest to the mean and/or median.
  • the dimer acid can be any dicarboxylic acid having at least 4 carbon atoms. They can be linear or branched, such as, for example, the dimers prepared from malonic acid, succinic acid, fumaric acid, dimethylglutaric acid or trimethyladipic acid, and from their anhydrides.
  • Dimer fatty acids are particularly useful. As is known, these are mixtures of acyclic and cyclic dicarboxylic acids which are obtained by a catalyzed dimerization reaction of unsaturated fatty acids containing from 12 to 22 carbon atoms.
  • the dicarboxylic acids can also contain, to a lesser extent, tri- and polyfunctional carboxylic acids.
  • the functionality of the mixture must not exceed a mean molar value of 2.4.
  • Preferred dimer acids are typically derived from triglycerides rich in C 18 ester groups, which can be hydrolyzed to produce unsaturated fatty C 18 monoacids.
  • the starting materials can be derived from tallow oil and rapeseed oil but other natural sources, such as flax seeds, soybean, pumpkin and walnut, can be used.
  • the target monoacids used in the reaction are rich in forms of oleic and linoleic acids which are described in the list of fatty acids which is contained below. Dimerization results mainly in the dimerization of unsaturated fatty acids, but trimers are also formed.
  • the product can be stored in the form of a mixture of reaction products or it can be further distilled or otherwise separated into molecular weight fractions.
  • the dimerization reaction produces a predominance (at least 60% by weight, more preferably at least 75% by weight) of dimer acid (C 36 diacid) but also produces C 54 trimer acids (less than 30% by weight, more preferably less than 25% by weight).
  • a standard hydrogenated dimer acid from Oleon, Radiacid 0960® which contains 87% by weight of dimer and 10% by weight of trimer acid, is used.
  • the polymer as described is characterized by a higher molecular weight, a more hydrophobic nature and a higher viscosity than those which can be provided by pure diacids of lower molecular weight.
  • trimer acid further improves the molecular weight and the performance qualities of these polymers.
  • the copolymer of the present invention is prepared from at least one hydrogenated dimer acid.
  • the polymer is prepared from a hydrogenated dimer acid comprising hydrogenated dimerized C 18 fatty acids, which hydrogenated dimer acid is obtained by dimerization of unsaturated C 18 fatty acids and subsequent hydrogenation.
  • the hydrogenated dimer acid contains a content of trimer acid ranging from approximately 5% to 25% by weight, based on the total weight of hydrogenated dimer acid.
  • the hydrogenated dimer acid contains a predominance (at least 60% by weight, more preferentially at least 75% by weight, but at most 95% by weight, or better still at most 90% by weight, or even better still at most 85% by weight) of hydrogenated dimer acid (C 36 diacid) and also contains hydrogenated C 54 trimer acids (less than 30% by weight, more preferably less than 25% by weight, but more than 5% by weight, more preferably more than 10% by weight).
  • Fatty C 8 -C 30 monoacids can include natural or refined fatty acids, such as hydrolyzed rapeseed oil, sunflower oils, and the like, but these contain both lower and higher MW chains.
  • Useful fatty monoacids may be linear, branched, saturated, unsaturated and aromatic materials with an acidity provided by carboxylic acid fractions.
  • Acids suitable for the invention include caprylic acid (C 8 ), pelargonic acid (C 9 ), capric acid (C 10 ), undecylic acid (C 11 ), lauric acid (C 12 ), tridecylic acid (C 13 ), myristic acid (C 14 ), pentadecylic acid (C 15 ), palmitic acid (C 16 ), margaric acid (C 17 ), stearic acid (C 18 ), isostearic acid (C 18 ), nonadecylic acid (C 19 ), arachidic acid (C 20 ), behenic acid (C 22 ) and lignoceric acid (C 24 ).
  • Another way to obtain a liquid product consists in using unsaturated, linear and branched, fatty monoacids.
  • unsaturated acids can include palmitoleic acid (C16:1), vaccenic acid (C18:1), oleic acid (C18:1), elaidic acid (C18:1), linoleic acid (C18:2), linolelaidic acid (C18:2), ⁇ -linolenic acid (C18:3), g-linolenic acid (C18:3), stearidonic acid (C18:4), paullinic acid (C20:1), gondoic acid (C20:1), dihomolinolenic acid (C20:3), mead acid (C20:3), arachidonic acid (C20:4), eicosapentaenoic acid (C20:5), erucic acid (C22:1), docosatetraenoic acid (C22:4),
  • isostearic acid will be preferred.
  • the polyester of the invention is a product of substantially or totally non-sequential reaction of the following components: (i) at least one polyglycerol-3 comprising at least 25% by weight of diglycerol, at least 45% by weight of triglycerol and at least 10% by weight of tetraglycerol, in each case relative to the total weight of polyglycerol-3; (ii) at least one hydrogenated dimer acid containing at least 60% by weight of hydrogenated C 36 diacid and from 5% to 25% by weight of hydrogenated C 54 triacid, in each case relative to the total weight of hydrogenated acid; and iii) isostearic acid.
  • the polyester is prepared by a one-step process which involves the introduction of all the reagents into a reaction vessel and subsequently the induction of an entirely random addition of the dimer acid and of the isostearic acid to the polyglycerol-3.
  • a total degree of esterification of the available polyglycerol hydroxyl fragments (total esterification) of from 24% to 74% and a degree of esterification of the available polyglycerol hydroxyl fragments by a dimer acid alone (esterification with a dimer acid) of from 20% to 40%.
  • the degree of esterification by end-cap units (esterification with a monoacid) is also defined in this description and it is important to maintain the esterification with a monoacid from 4% to 40%.
  • the reacted components are in a molar ratio of 1 mole of polyglycerol-3, 0.5 to 1 mole of dimer acid and 0.2 to 1.7 moles of fatty acid.
  • the reacted components are in a molar ratio of 1 mole of polyglycerol-3, 0.5 to 0.75 mole of dimer acid and 0.4 to 1.35 moles of isostearic acid.
  • the reacted components are in a molar ratio of 1 mole of polyglycerol-3, 0.5 to 0.7 mole of dimer acid and 0.65 to 1 mole of isostearic acid.
  • the reacted components are in a molar ratio of 1 mole of polyglycerol-3, 0.5 to 1 mole of hydrogenated dimer acid and 0.2 to 1.7 moles of isostearic acid.
  • the reacted components are in a molar ratio of 1 mole of polyglycerol-3, 0.5 to 0.75 mole of hydrogenated dimer acid and 0.4 to 1.35 moles of isostearic acid.
  • the reacted components are in a molar ratio of 1 mole of polyglycerol-3, 0.5 to 0.7 mole of hydrogenated dimer acid and 0.65 to 1 mole of isostearic acid.
  • the reacted components are in a molar ratio of 1 mole of polyglycerol-3, 0.5 to 1 mole of hydrogenated dimer acid and 0.2 to 1.7 moles of isostearic acid.
  • the reacted components are in a molar ratio of 1 mole of polyglycerol-3, 0.5 to 0.75 mole of hydrogenated dimer acid and 0.4 to 1.35 moles of isostearic acid.
  • the reacted components are in a molar ratio of 1 mole of polyglycerol-3, 0.5 to 0.7 mole of hydrogenated dimer acid and 0.65 to 1 mole of isostearic acid.
  • the reacted components are in a molar ratio of 1 mole of polyglycerol-3, 0.67 mole of hydrogenated C 36 dimer acid and 0.67 mole of isostearic acid.
  • the reacted components are in a molar ratio of 1 mole of polyglycerol-3, 0.5 mole of hydrogenated C 36 dimer acid and 1 mole of isostearic acid.
  • the target viscosity of the pure polymer must be > 50 000 mPa.s and less than 5 000 000 mPa.s at 25°C.
  • the target viscosity is > 75 000 mPa.s and ⁇ 2 500 000 mPa.s at 25°C.
  • the target viscosity is > 100 000 mPa.s and ⁇ 2 000 000 mPa.s at 25°C.
  • the target viscosity is > 1 000 000 mPa.s and ⁇ 2 000 000 mPa.s at 25°C.
  • the viscosity is measured using an MCR3O2® rheometer from Anton Paar Inc. Rough or smooth twin flat plates 50 mm in diameter were used, covered with a polymer sample, adjusted to a gap of 0.5 to 1 mm, and temperature and shear rate scans were performed.
  • the polyesters of the invention have Newtonian behaviour and thus have a constant viscosity over a wide range of shear rates.
  • the polymers of the present description demonstrated a reduced viscosity with temperature.
  • the viscosity measurements are reported at a precisely controlled temperature and generally in the form of a shear rate of 1. The values are reported in mPa.s.
  • polyesters of the invention are characterized by weight-average molecular masses > 2500 Da and ⁇ 1 000 000 Da, measured by GPC using linear polystyrene standards.
  • the GPC column used for these tests was constituted of: Phenolgel, 300 x 4.6 mm; a continuous tetrahydrofuran (THF) phase was used and injected at 0.35 ml/min, column oven maintained at 40°C; a 50 ⁇ l injection and a Wyatt Ri refractive index detector.
  • the calibration standards used were strictly linear polystyrene intended to be monodispersed.
  • the narrow range polystyrene GPC calibrating standards were prepared as a mobile phase and had maximum molecular weights of 1 290 000 Da, 560 000 Da, 65 500 Da, 28 500 Da, 10 100 Da, 1680 Da, 580 Da and 208 Da. Using standard methodologies, the weight- and number-average molecular weight is automatically calculated by standard GPC software.
  • the polyesters described have a weight-average molecular weight > 4000 Da and ⁇ 250 000 Da, measured by GPC using linear polystyrene standards. In a most preferred embodiment, the polymers described have a weight-average molecular weight > 5000 Da and ⁇ 150 000 Da, measured by GPC using linear polystyrene standards.
  • the polyester of the invention exhibits a combination of weight-average molecular weight > 5000 Da and ⁇ 150 000 Da, measured by GPC using linear polystyrene standards, and of viscosity at 25°C > 100 000 mPa.s and ⁇ 2 000 000 mPa.s.
  • the polyester of the invention is a substantially or completely non-sequential reaction product of the following components: (i) at least one polyglycerol-3 in the form of a mixture comprising at least 25% by weight of diglycerol, at least 45% by weight of triglycerol and at least 10% by weight of tetraglycerol, in each case relative to the total weight of polyglycerol-3 in the form of a mixture; (ii) at least one hydrogenated dimer acid containing at least 60% by weight of hydrogenated C 36 diacid and from 5% to 25% by weight of hydrogenated C 54 triacid, in each case relative to the total weight of hydrogenated acid; and (iii) isostearic acid; in which the polymer exhibits a combination of weight-average molecular weight > 5000 Da and ⁇ 15 000 Da, measured with GPC using linear polystyrene standards, and of viscosity of the pure polymer > 100 000 MPa.s and ⁇ 2 000 000 MPa.s at
  • the above numbers can be adjusted using the actual (and not theoretical) hydroxyl fractions and carboxylic acid fractions, as are determined by methods such as mass spectrometry, NMR and liquid chromatography.
  • the above esterification ranges are based on the ideal structure of the polyglycerol-3 and of the C 36 dimer acid.
  • the actual ranges can thus be slightly different from the values indicated above and can be calculated based on these analytical values.
  • the initial acid values in the light of the distribution of the polyglycerol, monoacid and polyacid fractions present, can be reliably calculated using the actual acid value determined by the starting ingredient used.
  • the initial total acid number (“AV”, which is commonly defined in mg of KOH/g of total reagent) is 135 AV.
  • This comprises 68 AV for the dimer acid and 67 AV for the isostearic acid for a preferred embodiment containing 1 mole of polyglycerol-3, 0.5 mole of hydrogenated C 36 dimer acid and 1 mole of isostearic acid.
  • All the preferred ratio embodiments described above have a corresponding initial AV which can be calculated. When, during the polymerization reaction, the AV units are reduced, this ratio gives the percentage of conversion of the reaction from the total initial reactive acid fractions to the final residual acid fractions.
  • T ACH 1 - final AV/initial AV
  • the polyesters of the invention have final acid numbers of from 0.1 to ⁇ 10 mg of KOH/g of polymer.
  • the polyesters of the invention have final acid numbers of from 0.1 to ⁇ 5 mg of KOH/g of polymer.
  • the completion rate of the reaction is defined by the equation 1- final AV/initial AV, the completion rate of the reaction of such mixtures to give final polymer is > 80%.
  • the completion rate of the reaction of such mixtures to give final polymer is > 90%.
  • the completion rate of the reaction of such mixtures to give final polymer is > 95%.
  • the polyester of the invention is a reaction product of a polyglycerol-3, of a hydrogenated C 36 dimer acid and of isostearic acid in a molar ratio of 1/0.5/1, as described in Example 10 (copolymer) of document US 2021/0259945.
  • the non-volatile oil is a triglyceride of fatty acids containing from 4 to 24 carbon atoms, and more particularly a triglyceride of caprylic/capric acids (INCI name: Caprylic/Capric Triglyceride).
  • the oily solution of polyester of the invention can be obtained by mixing the polyester with the non-volatile oil or oils at approximately 80-100°C. The combined mixture is subsequently further cooled to 50-70°C to be discharged from the reactor and stored.
  • the oily solution of polyester of the invention preferably contains the polyester at a concentration of 10% to 99% by weight, more preferentially of 30% to 90% by weight, more particularly of 50% to 80% by weight, relative to the total weight of the oily solution.
  • the composition of the invention contains an oily solution comprising 40% by weight of triglyceride of caprylic/capric acids and 60% by weight of polyester of polyglycerol-3, of hydrogenated C 36 dimer acid and of isostearic acid, relative to the total weight of the oily solution, in a molar ratio of 1/0.5/1, as described in Example 10 (copolymer) and Example 28 (oily mixture) of document US 2021/0259945.
  • the composition comprises an oily solution comprising: a) a polyester obtained by reaction: (i) of polyglycerol-3, and (ii) of a hydrogenated C 36 dimer acid, and (iii) of isostearic acid; the components (i), (ii) and (iii) reacted being in a molar ratio of 1 mole of polyglycerol-3, of 0.5 to 1 mole of dimer acid and of 0.1 to 2.0 moles of fatty acids; and b) a triglyceride of caprylic/capric acids; said mixture having, as INCI name: Diisostearoyl Polyglyceryl-3 Dimer Dilinoleate (and) Caprylic/Capric Triglyceride.
  • Such an oily solution is sold under the name SolAmaze Natural® by Nouryon, comprising 60% by weight, as active material, of polyester and 40% by weight of a triglyceride of caprylic/capric acids, relative to the total weight of the oily solution.
  • composition of the invention comprises a continuous oily phase B).
  • Said phase is liquid (in the absence of structuring agent) at ambient temperature (20-25°C). It is organic and water-immiscible.
  • the oily phase B) of the composition of the invention comprises: 1) at least one volatile hydrocarbon oil; and 2) optionally at least one non-volatile oil; the ratio by weight of the total amount of non-volatile oil(s) to the amount of polyester being less than 8.0.
  • the total concentration of oily phase B) of the composition of the invention preferably varies from 20% to 50% by weight and more particularly ranges from 22% to 40% by weight, relative to the total weight of the composition.
  • composition in accordance with the present invention comprises at least one volatile hydrocarbon oil.
  • oil is understood to mean any fatty substance in the liquid form at ambient temperature (25°C) and at atmospheric pressure (760 mmHg or 10 5 Pa).
  • hydrocarbon oil is understood to mean an oil containing predominantly hydrogen and carbon atoms and optionally one or more functions chosen from hydroxyl, ester, ether and carboxyl functions.
  • volatile oil refers to any oil that is capable of evaporating on contact with the skin in less than one hour, at ambient temperature and atmospheric pressure.
  • the volatile oil is a volatile cosmetic compound, liquid at ambient temperature, having in particular a non-zero vapour pressure, at ambient temperature and atmospheric pressure, in particular having a vapour pressure ranging from 2.66 Pa to 40 000 Pa, especially ranging from 2.66 Pa to 13 000 Pa, and more particularly ranging from 2.66 Pa to 1300 Pa.
  • the volatile hydrocarbon oils which can be used in the compositions according to the invention can be chosen from branched C 8 -C 16 alkanes. Mention may in particular be made of C 8 -C 16 isoalkanes of petroleum origin (also known as isoparaffins), such as isododecane (also known as 2,2,4,4,6-pentamethylheptane), isodecane, isohexadecane and, for example, the oils sold under the Isopar® or Permethyl® trade names.
  • C 8 -C 16 isoalkanes of petroleum origin also known as isoparaffins
  • isododecane also known as 2,2,4,4,6-pentamethylheptane
  • isodecane isohexadecane
  • the oils sold under the Isopar® or Permethyl® trade names for example, the oils sold under the Isopar® or Permethyl® trade names.
  • branched C 8 -C 16 esters such as isohexyl neopentanoate.
  • Other volatile hydrocarbon oils such as petroleum distillates, in particular those sold under the name Shell Solt® by Shell, can also be used.
  • volatile hydrocarbon oils which can be used in the compositions according to the invention can be chosen from volatile linear alkanes comprising from 6 to 14 carbon atoms.
  • alkanes suitable for the invention Mention may be made, by way of examples of linear alkanes suitable for the invention, of the alkanes described in the patent applications WO2007/068371 and WO2008/155059 of Cognis (mixtures of different alkanes differing by at least one carbon). These alkanes are obtained from fatty alcohols, which are themselves obtained from coconut kernel oil or palm oil.
  • C 6 -C 14 alkanes suitable for the invention, of n-hexane (C 6 ), n-heptane (C 7 ), n-octane (C 8 ), n-nonane (C 9 ), n-decane (C 10 ), n-undecane (C 11 ), n-dodecane (C 12 ), n-tridecane (C 13 ), n-tetradecane (C 14 ) and mixtures thereof.
  • n-dodecane C 12
  • n-tetradecane C 14
  • n-dodecane and of n-tetradecane is used.
  • Use may in particular be made of the dodecane/tetradecane mixture in the 85/15 weight ratio sold by Biosynthis under the reference Vegelight 1214®.
  • a mixture of volatile linear C 9 -C 12 alkanes with the INCI name: C9-12 Alkane such as the product sold by Biosynthis under the reference Vegelight Silk®.
  • n-undecane C 11
  • n-tridecane C 13
  • the volatile hydrocarbon oil is isododecane.
  • the volatile oil(s) are preferably present in the composition of the invention at contents ranging from 10% to 30% by weight, preferably from 15% to 25% by weight, relative to the total weight of said composition.
  • non-volatile oil is understood to mean an oil remaining on the skin or the keratin fibre at ambient temperature and atmospheric pressure for at least several hours and having in particular a vapour pressure of less than 2.66 Pa, preferably of less than 0.13 Pa.
  • the vapour pressure can be measured according to the static method or by the effusion method by isothermal thermogravimetry as a function of the vapour pressure (standard OECD 104).
  • non-volatile oils in accordance with the invention can be chosen from the group constituted of hydrocarbon oils, silicone oils and mixtures thereof.
  • the composition of the invention comprises at least one non-volatile oil, the ratio by weight of the total amount of non-volatile oil(s) to the amount of polyester being less than 8.0.
  • the composition in accordance with the invention comprises at least one non-volatile oil; the ratio by weight of the total amount of non-volatile oil(s) to the amount of polyester is between 0 and 8, and more particularly from 1 to 3.
  • composition of the invention comprises an aqueous phase C) in which the liquid component(s) represent at least 50% by weight of the total weight of the composition.
  • the aqueous phase C) comprises water and optionally water-soluble or water-miscible ingredients, such as water-soluble solvents, water-soluble active agents and water-soluble antimicrobial agents.
  • a water that is suitable for use in the invention may be a demineralized water, a floral water such as cornflower water and/or a mineral water such as Vittel water, Lucas water or La Roche Posay water and/or a spring water.
  • water-soluble solvents that may be present in the aqueous phase
  • the composition of the invention additionally comprises at least one C 2 -C 6 monoalcohol, in particular ethanol.
  • the composition of the invention comprises one or more liquid components of the aqueous phase in a content ranging from 50% to 80% by weight, more preferentially ranging from 52% to 70% and even more preferentially ranging from 55% to 65% by weight relative to the total weight of the composition.
  • the liquid component(s) present in the aqueous phase C) are generally constituted in part or totally of water, preferably of water and one or more water-soluble solvents such as those indicated above, active agents in liquid form, antimicrobial agents in liquid form, and mixtures thereof.
  • the composition according to the invention comprises water in an amount of at least 50% by weight, preferably ranging from 50% to 70% by weight, more preferentially ranging from 50% to 62% by weight relative to the total weight of the composition.
  • the water-in-oil emulsions according to the invention comprise at least one non-ionic surfactant D) with an HLB of less than 8.0, the chemical structure of which results from the reaction of at least one polyhydroxystearic acid and/or of at least one polyricinoleic acid with a polyol containing at least two alcohol functions.
  • the polyol is a polyethylene glycol or a polyglycerol.
  • the term “surfactant” is understood to mean an amphiphilic compound, that is to say a compound exhibiting two parts of different polarities. Generally, one is lipophilic (soluble or dispersible in an oily phase). The other is hydrophilic (soluble or dispersible in water).
  • Emulsifying surfactants are characterized by the value of their HLB (Hydrophilic Lipophilic Balance), the HLB being the ratio of the hydrophilic part to the lipophilic part in the molecule.
  • HLB Hydrophilic Lipophilic Balance
  • the term “HLB” is well known to a person skilled in the art and is described, for example, in “The HLB System. A Time-Saving Guide to Emulsifier Selection” (published by ICI Americas Inc.; 1984).
  • the HLB is generally less than 8.0.
  • the HLB of the surfactant(s) used according to the invention can be determined by the Griffin method or the Davies method.
  • the content of the non-ionic surfactant(s) D) according to the invention preferably varies from 1% to 10% by weight, more preferentially from 1.5% to 7% by weight and even more preferentially from 2% to 5% by weight relative to the total weight of the composition.
  • the composition according to the invention additionally comprises at least one pulverulent dyestuff.
  • the pulverulent dyestuffs may be chosen from inorganic pigments, organic pigments, pearlescent agents and mixtures thereof.
  • pigments means white or coloured, mineral or organic particles, which are insoluble in an aqueous medium, and which are intended to colour and/or opacify the resulting composition and/or deposit. These pigments may be white or coloured, and mineral and/or organic.
  • the pigments used according to the invention are chosen from mineral pigments.
  • mineral pigment means any pigment that satisfies the definition in Ullmann’s encyclopedia in the chapter on inorganic pigments. Mention may be made, among the mineral pigments which are of use in the present invention, of zirconium oxide or cerium oxide, and also zinc oxide, iron oxide (black, yellow or red) or chromium oxide, manganese violet, ultramarine blue, chromium hydrate and ferric blue, titanium dioxide or metal powders, such as aluminium powder and copper powder.
  • the size of the pigment of use in the context of the present invention is generally greater than 100 nm and can range up to 10 ⁇ m, preferably from 200 nm to 5 ⁇ m and more preferentially from 300 nm to 1 ⁇ m.
  • D[50] represents the maximum size exhibited by 50% by volume of the particles.
  • the pigments can be coated according to the invention with an N-acylamino acid or one of its salts which can comprise an acyl group having from 8 to 22 carbon atoms, such as, for example, a 2-ethylhexanoyl, caproyl, lauroyl, myristoyl, palmitoyl, stearoyl or cocoyl group.
  • an N-acylamino acid or one of its salts which can comprise an acyl group having from 8 to 22 carbon atoms, such as, for example, a 2-ethylhexanoyl, caproyl, lauroyl, myristoyl, palmitoyl, stearoyl or cocoyl group.
  • the pigments which can be used according to the invention can also be organic pigments.
  • These pigments can also be in the form of composite pigments as are described in patent EP 1 184 426.
  • These composite pigments can be composed in particular of particles comprising an inorganic core at least partially covered with an organic pigment and at least one binder providing the fixing of the organic pigments to the core.
  • the pigment can also be a lake.
  • the term “lake” is understood to mean insolubilized dyes adsorbed onto insoluble particles, the assembly thus obtained remaining insoluble during use.
  • the inorganic substrates onto which the dyes are adsorbed are, for example, alumina, silica, calcium sodium borosilicate or calcium aluminium borosilicate, and aluminium.
  • Mention may be made, among the organic dyes, of cochineal carmine. Mention may also be made of the products known under the following names: D&C Red 21 (CI 45 380), D&C Orange 5 (CI 45 370), D&C Red 27 (CI 45 410), D&C Orange 10 (CI 45 425), D&C Red 3 (CI 45 430), D&C Red 4 (CI 15 510), D&C Red 33 (CI 17 200), D&C Yellow 5 (CI 19 140), D&C Yellow 6 (CI 15 985), D&C Green (CI 61 570), D&C Yellow 1 O (CI 77 002), D&C Green 3 (CI 42 053) or D&C Blue 1 (CI 42 090).
  • D&C Red 21 CI 45 380
  • D&C Orange 5 CI 45 370
  • D&C Red 27 CI 45 410
  • D&C Orange 10 CI 45 425
  • D&C Red 3 CI 45 430
  • D&C Red 4 CI 15 510
  • Mention may be made, by way of example of a lake, of the product known under the name D&C Red 7 (CI 15 850:1).
  • the composition according to the invention comprises at least one pulverulent dyestuff of inorganic pigment type, in particular chosen from metal oxides, and more particularly uncoated black iron oxides (CI 77499).
  • inorganic pigment type in particular chosen from metal oxides, and more particularly uncoated black iron oxides (CI 77499).
  • the pearlescent agents can be chosen from white pearlescent pigments, such as mica coated with titanium or with bismuth oxychloride, coloured pearlescent pigments, such as titanium oxide-coated mica with iron oxides, titanium oxide-coated mica with in particular ferric blue or chromium oxide, or titanium oxide-coated mica with an organic pigment of the abovementioned type, and also pearlescent pigments based on bismuth oxychloride.
  • white pearlescent pigments such as mica coated with titanium or with bismuth oxychloride
  • coloured pearlescent pigments such as titanium oxide-coated mica with iron oxides, titanium oxide-coated mica with in particular ferric blue or chromium oxide, or titanium oxide-coated mica with an organic pigment of the abovementioned type, and also pearlescent pigments based on bismuth oxychloride.
  • the pulverulent dyestuff(s) is (are) present, preferably, in the composition in a content ranging from 1% to 30% by weight, preferably from 2% to 15% by weight, relative to the total weight of the composition.
  • a composition according to the invention can comprise at least one water-soluble or fat-soluble dyestuff and preferably in a proportion of at least 0.01% by weight, relative to the total weight of the composition.
  • the additional dyestuffs suitable for the invention can be fat-soluble.
  • fat-soluble dyestuff is understood to mean any natural or synthetic, generally organic, compound which is soluble in an oily phase or solvents miscible with a fatty substance and which is capable of imparting colour.
  • fat-soluble dyes suitable for the invention of synthetic or natural fat-soluble dyes, such as, for example, DC Red 17, DC Red 21, DC Red 27, DC Green 6, DC Yellow 11, DC Violet 2, DC Orange 5, Sudan red, carotenes ( ⁇ -carotene, lycopene), xanthophylls (capsanthin, capsorubin, lutein), palm oil, Sudan brown, quinoline yellow, annatto or curcumin.
  • synthetic or natural fat-soluble dyes such as, for example, DC Red 17, DC Red 21, DC Red 27, DC Green 6, DC Yellow 11, DC Violet 2, DC Orange 5, Sudan red, carotenes ( ⁇ -carotene, lycopene), xanthophylls (capsanthin, capsorubin, lutein), palm oil, Sudan brown, quinoline yellow, annatto or curcumin.
  • the additional dyestuffs suitable for the invention can be water-soluble.
  • water-soluble dyestuff is understood to mean any natural or synthetic, generally organic, compound which is soluble in an aqueous phase or water-miscible solvents and which is capable of imparting colour.
  • water-soluble dyes suitable for the invention of synthetic or natural water-soluble dyes, such as, for example, FDC Red 4, DC Red 6, DC Red 22, DC Red 28, DC Red 30, DC Red 33, DC Orange 4, DC Yellow 5, DC Yellow 6, DC Yellow 8, FDC Green 3, DC Green 5, FDC Blue 1, betanin (beetroot), carmine, copper chlorophyllin, methylene blue, anthocyanins (enocyanin, black carrot, hibiscus or elder), caramel or riboflavin.
  • synthetic or natural water-soluble dyes such as, for example, FDC Red 4, DC Red 6, DC Red 22, DC Red 28, DC Red 30, DC Red 33, DC Orange 4, DC Yellow 5, DC Yellow 6, DC Yellow 8, FDC Green 3, DC Green 5, FDC Blue 1, betanin (beetroot), carmine, copper chlorophyllin, methylene blue, anthocyanins (enocyanin, black carrot, hibiscus or elder), caramel or riboflavin.
  • compositions in accordance with the invention can also comprise at least one filler which makes it possible in particular to confer on them additional properties of improved stability, wear property, coverage and/or mattness.
  • filler should be understood as meaning colourless or white solid particles of any shape which are provided in an insoluble form and dispersed in the medium of the composition. They make it possible to confer body or firmness on the composition and/or softness and uniformity on the make-up.
  • the fillers can be inorganic or organic.
  • they can be chosen from natural fillers or fillers of natural origin.
  • 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, milling, refining, distillation, purification or filtration.
  • compound of natural origin is understood to mean a natural compound which has undergone one or more additional chemical or industrial treatments, bringing about modifications which do not affect the essential qualities of this compound, and/or a compound predominantly comprising natural constituents which have or have not undergone transformations. Mention may be made, as non-limiting example of additional chemical or industrial treatment bringing about modifications which do not affect the essential qualities of a natural compound, of those permitted by the controlling bodies, such as Ecocert (Reference system for biological and ecological cosmetic products, January 2003), or defined in recognized handbooks in the field, such as “Cosmetics and Toiletries Magazine”, 2005, Vol. 120, 9: 10.
  • the fillers used in the compositions according to the present invention can be of lamellar, globular, spherical or fibrous forms or of any other form intermediate between these defined forms.
  • the fillers according to the invention may or may not be surface-coated, and in particular they may be surface-treated with amino acids or any other substance which promotes the dispersion and the compatibility of the filler in the composition.
  • inorganic fillers of talcs, natural or synthetic micas, such as synthetic fluorphlogopites, kaolin, calcium carbonate, magnesium carbonate, hydroxyapatite, boron nitride, bismuth oxychloride, glass or ceramic microcapsules, or composites of silica and of titanium dioxide, such as the TSG® series sold by Nippon Sheet Glass.
  • organic fillers of micronized natural waxes; metal soaps derived from organic carboxylic acids having from 8 to 22 carbon atoms, preferably from 12 to 18 carbon atoms, for example zinc, magnesium or lithium stearate, zinc laurate or magnesium myristate; lauroyl lysine; or cellulose powders, such as that sold by Daito in the Cellulobeads® range.
  • the filler(s) are present in the composition in a content ranging from 0.5% to 20% by weight, preferably from 1% to 15% by weight, more particularly from 3% to 10% by weight, relative to the total weight of the composition.
  • composition used according to the invention may be a care and/or makeup composition for keratin materials, such as the skin, the lips, the contour of the eyes, the eyelids, the eyelashes or the eyebrows.
  • composition according to the invention is a makeup product for the skin, such as foundations, face powders and eyeshadows.
  • composition according to the invention is a makeup product for the lips, such as a lipstick or a gloss.
  • composition according to the invention is a makeup product for the contour of the eyes, such as an eyeliner, or for the eyelashes or for the eyebrows, such as a mascara.
  • compositions are in particular prepared according to the general knowledge of a person skilled in the art.
  • the present invention also relates to an assembly, or kit, for packaging and applying a cosmetic composition for coating keratin materials, comprising: - a packaging device comprising said cosmetic composition for coating keratin materials, as described above, - an applicator for said composition.
  • the container can delimit one or more compartment(s).
  • the container may be, for example, in the form of a tube.
  • Such an applicator may be secured to a cap mounted reversibly on said container between a closure position of said container and a makeup position.
  • such an applicator can be irreversibly fitted to said container.
  • phase A The constituents of phase A were weighed together while dividing their respective amounts into two equal parts in two beakers, one being the main beaker and the other a supplementary beaker.
  • Each of the two beakers was homogenized at ambient temperature while stirring with a Rayneri stirrer equipped with a deflocculating blade for 3 minutes at 500 rpm.
  • the water was added very slowly to the main beaker for 4 to 5 minutes, while stirring with a Rayneri stirrer equipped with a stator rotor and gradually increasing the stirring speed from 800 to 1600 rpm in increments of 200 rpm every minute.
  • phase C the ingredients of phase C were added to the supplementary beaker and the mixture was stirred with a Rayneri stirrer equipped with a deflocculating blade for 5 minutes at 500 rpm.
  • the contents of the supplementary beaker were then added to the main beaker, stirring being maintained at 1600 rpm until the mixture was completely homogenized.
  • the viscosity at 25°C of each of the compositions was measured using an RM 200® rotary rheometer from Lamy Rheology Instruments, after 10 minutes of rotation of the spindle 3 at a speed of 200 rpm. After production, the samples are stored for 24 to 72 h at ambient temperature (25°C). The viscosities are measured at a temperature of 25°C, kept constant by means of an EVA MS-R® temperature controller from Lamy Rheology Instruments.
  • Example Viscosity (mPa.s) Peg 30 Dipolyhydroxystearate (CITHROL DPHS-SO-(MV)® from CRODA)
  • Example 1 (invention) 192 Polyglyceryl-2-Dipolyhydroxystearate (DEHYMULS PGPH® from BASF)
  • Example 2 (invention) 694 Polyglyceryl-6 Polyhydroxystearate (and) Polyglyceryl-6 Polyricinoleate (EMULIUM ILLUSTRO from GATTEFOSSE)
  • Example 3 820 Polyglyceryl-4 Diisostearate/Polyhydroxystearate/Sebacate (ISOLAN GPS® from EVONIK)
  • Example 4 (invention) 1150 Polyglyceryl-6 Polyricinoleate (SY-GLYSTER CRS-75 from SAKAMOTO YAKUHIN)
  • Example 5 (invention) 1405 Polyglyceryl-3 Diisostearate (LAMEFORM TGI® from BASF)
  • Example 6 (
  • Examples 1 to 5 of the invention comprising a non-ionic surfactant with an HLB of less than 8.0, which has a polyhydroxystearic and/or polyricinoleic chain in its chemical structure, exhibited a fluid texture for the purposes of the invention (viscosity ⁇ 1500 MPa.s) unlike Comparative Examples 6 to 10 comprising a non-ionic surfactant with an HLB of less than 8.0 having a different chemical structure.
  • Examples 1 to 5 of foundation, of the invention were characterized by their ease of application in connection with their fluidity and a film after very gentle drying.
  • Examples 11 to 13, outside the invention, of a common support were prepared with Example 4 of the invention as described above, but in which the non-ionic surfactant/polyester weight ratio was varied.
  • Examples 11 to 13 were prepared according to the same procedure as Examples 1 to 10.
  • Example 4 (invention) Example 11 (comparative) Example 12 (comparative) Example 13 (comparative) Isododecane 17.33 17.33 17.33 17.33 Polyglyceryl-4 Diisostearate/Polyhydroxystearate/Sebacate (ISOLAN GPS® - EVONIK) 2.50 2.50 2.50 2.50 Diisostearoyl Polyglyceryl-3 Dimer Dilinoleate (60%) (and) Caprylic/Capric Triglyceride (40%) (SolAmaze Natural® - Nouryon) 4.16 5.0 5.55 8.32 Caprylic/Capric Triglyceride 0.77 0.43 0.21 0 Water 58.02 57.52 57.19 54.63 Synthetic Fluorphlogopite 1.22 1.22 1.22 1.22 Titanium Dioxide (and) Disodium Stearoyl Glutamate (and) Aluminium Hydroxide/CI 77891 (and) Disodium Stearoyl Glutamate (and) Aluminium Hydroxide/
  • the viscosity at 25°C of each of the Compositions 4 and 11 to 13 was measured using an RM 200® rotary rheometer from Lamy Rheology Instruments, after 10 minutes of rotation of the spindle 3 at a speed of 200 rpm under the same conditions as above.
  • Example 14 outside the invention which is a foundation not containing a non-ionic surfactant with an HLB ⁇ 8.0 having a polyhydroxystearic and/or polyricinoleic structure, was prepared:
  • Example 14 Phase Isododecane 17.33 A Diisostearoyl Polyglyceryl-3 Dimer Dilinoleate (60%) (and) Caprylic/Capric Triglyceride (40%) (SolAmaze Natural® - Nouryon) 4.16 Caprylic/Capric Triglyceride 0.77 Water 60.52 B Synthetic Fluorphlogopite 1.22 C Titanium Dioxide (and) Disodium Stearoyl Glutamate (and) Aluminium Hydroxide/CI 77891 (and) Disodium Stearoyl Glutamate (and) Aluminium Hydroxide 8.71 Iron Oxides (and) Disodium Stearoyl Glutamate (and) Aluminium Hydroxide/CI 77499 (and) Disodium Stearoyl Glutamate (and) Aluminium Hydroxide 0.17 Iron Oxides (and) Disodium Stearoyl Glutamate (and) Aluminium Hydroxide/CI 77491 (and) Disodium Stearoyl Glutamate (and) Aluminium Hydroxide 0.17
  • the viscosity of the composition was measured at 25°C under the same conditions as those of Examples 1 to 13.
  • the viscosity of this foundation was 2995 mPa.s.

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Abstract

La présente invention concerne une émulsion eau-dans-huile fluide comprenant : A) au moins un polyester qui est le produit de la réaction des composants (i), (ii) et (iii) suivants : (i) au moins un polyglycérol-3 ; (ii) au moins un acide dimère ; et (iii) au moins un monoacide gras comportant de 8 à 30 atomes de carbone, les composants (i), (ii) et (iii) ayant réagi étant présents selon un rapport molaire de 1 mole de polyglycérol-3, de 0,5 à 1 mole d'acide dimère et de 0,1 à moins de 2,0 moles de monoacide gras ; et B) au moins une phase huileuse continue comprenant : 1) au moins une huile hydrocarbonée volatile ; et 2) éventuellement au moins une huile non volatile ; et C) au moins une phase aqueuse dispersée dans ladite phase huileuse, dans laquelle le ou les composants liquides de ladite phase aqueuse représentent au moins 50% en poids du poids total de la composition ; et D) au moins un tensioactif non ionique de HLB inférieur à 8,0 dont la structure chimique résulte de la réaction d'au moins un acide polyhydroxystéarique et/ou d'au moins un acide polyricinoléique avec un polyol contenant au moins deux fonctions alcool ; le rapport pondéral tensioactif(s) non ionique(s) D)/polyester A) est supérieur ou égal à 0,9 et de préférence supérieur ou égal à 1,0.
PCT/EP2024/068758 2023-10-11 2024-07-03 Emulsion e/h fluide comprenant un polyester particulier, un alcane volatil, au moins 50% de composant(s) liquide(s) de la phase aqueuse, et un tensioactif non ionique polyhydroxystéarique et/ou polyricinoléique Pending WO2025078046A1 (fr)

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FRFR2310864 2023-10-11
FR2310864A FR3153990A1 (fr) 2023-10-11 2023-10-11 Emulsion E/H fluide avec un polyester particulier, un alcane volatil, au moins 50% de composant(s) liquide(s) de la phase aqueuse, un tensioactif non-ionique polyhydroxystéarique et/ou polyricinoléique

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FR2679771A1 (fr) 1991-08-01 1993-02-05 Oreal Utilisation pour la teinture temporaire des fibres keratiniques d'un pigment insoluble obtenu par polymerisation oxydante de derives indoliques.
EP1184426A2 (fr) 2000-09-01 2002-03-06 Toda Kogyo Corporation Particules composites, procédé de préparation, pigment et peinte, et composition de résine les utilisants
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