WO2015014789A1 - Composition cosmétique anhydre comprenant de l'alkylcellulose, au moins un ester de dextrine ramifié et au moins un alcool gras - Google Patents

Composition cosmétique anhydre comprenant de l'alkylcellulose, au moins un ester de dextrine ramifié et au moins un alcool gras Download PDF

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Publication number
WO2015014789A1
WO2015014789A1 PCT/EP2014/066171 EP2014066171W WO2015014789A1 WO 2015014789 A1 WO2015014789 A1 WO 2015014789A1 EP 2014066171 W EP2014066171 W EP 2014066171W WO 2015014789 A1 WO2015014789 A1 WO 2015014789A1
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composition
composition according
alcohol
branched
dextrin
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PCT/EP2014/066171
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English (en)
Inventor
Roshanak Debeaud
Régine IMBERT
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L'oreal
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    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
    • A61K8/73—Polysaccharides
    • A61K8/731—Cellulose; Quaternized cellulose derivatives
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/34—Alcohols
    • A61K8/342—Alcohols having more than seven atoms in an unbroken chain
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
    • A61K8/73—Polysaccharides
    • 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
    • A61Q1/04—Preparations containing skin colorants, e.g. pigments for lips
    • A61Q1/06—Lipsticks
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
    • A61K2800/20—Chemical, physico-chemical or functional or structural properties of the composition as a whole
    • A61K2800/30—Characterized by the absence of a particular group of ingredients
    • A61K2800/31—Anhydrous

Definitions

  • This invention relates to an anhydrous cosmetic composition
  • an anhydrous cosmetic composition comprising alkylcellulose, at least one branched dextrin ester and at least one fatty alcohol.
  • cosmetic compositions must provide an aesthetic effect when applied to the skin and/or lips, and maintain this aesthetic effect over time. Once applied, they must in particular resist various external factors capable of modifying their aesthetic effect such as perspiration or tears for foundation, or saliva for lipstick.
  • the improvement in stability, in particular of the color of the deposit of cosmetic products over time, once applied to the skin and/or lips, is a constant concern for formulators practicing in the field of lipsticks, lip glosses and other skin and/or lip care products.
  • ethylcellulose makes it possible, when it is used in a sufficient amount in cosmetic and/or therapeutic compositions, to obtain deposits having improved adhesion and stability properties, in particular on the lips or skin. It has also been demonstrated that ethylcellulose, solubilized in a sufficient amount in the compositions, enables the formation of a film on the skin and/or lips to be facilitated, and the water resistance of this film to be improved.
  • mono-alcohols having 2 to 8 carbon atoms are preferred for solubilizing sufficient amounts of ethylcellulose in cosmetic or pharmaceutical compositions.
  • these volatile mono-alcohols have the disadvantage of being potentially uncomfortable (tautness, dryness), or even irritating for the skin and/or lips, and consequently may be detrimental when used repeatedly on the skin or lips.
  • compositions comprising a sufficient amount of alkylcellulose, that are homogeneous, and capable of forming a deposit on the skin and/or lips that is homogeneous, bright, non-tacky and that has satisfactory stability properties.
  • compositions comprising a sufficient amount of dispersed alkylcellulose, comfortable to apply and wear, in particular not having a tacky effect (or having only a slightly tacky effect), and enabling a deposit to be obtained that is homogeneous, bright and stable and that does not move into lines and wrinkles over the course of the day.
  • This invention is specifically intended to respond to these needs.
  • This invention is intended to provide a cosmetic composition, in particular in the form of a lipstick, having good brightness properties.
  • This invention is also intended to provide a cosmetic composition, in particular in the form of a lipstick, having very good brightness and color stability properties.
  • This invention is also intended to provide a cosmetic composition, in particular in the form of a lipstick, making it possible to prevent the transfer of said composition onto materials with which it may come into contact, such as, in particular, a cup.
  • This invention is also intended to provide a cosmetic composition, in particular in the form of a lipstick, that is comfortable to apply and wear, in particular not having a tacky effect.
  • this invention relates to an anhydrous cosmetic composition
  • an anhydrous cosmetic composition comprising, in a physiologically acceptable medium:
  • ROH at least one fatty alcohol ROH, R representing a saturated or unsaturated, linear or branched hydrocarbon radical, comprising at least 8 carbon atoms.
  • a cosmetic composition according to the invention enables a deposit to be obtained having good properties in terms of stability of color and brightness, comfort on application and over time, and brightness. It has also been observed by the inventors that the composition according to the invention makes it possible to prevent the transfer, for example onto a cup, of said composition.
  • anhydrous refers to a composition in which water is not deliberately added, but may be present in trace amounts in the various compounds used in the composition (for example, a water content of less than 2% by weight with respect to the total weight of the composition).
  • a cosmetic composition according to the invention can be in liquid or solid form at 20 ⁇ and at atmospheric pressure.
  • the composition according to the invention is in liquid form at 20 ⁇ €.
  • liquid refers to a fluid composition that is capable of flowing under its own weight, at 20 °C and at atmospheric pressure (760 mm Hg), by contrast with so-called solid compositions.
  • the cosmetic composition according to the invention is a liquid lipstick, also called gloss.
  • the composition is in solid form at 20 °C and at atmospheric pressure. It can, for example, be a lipstick.
  • solid characterizes the state of the composition at a temperature of 20 ' ⁇ .
  • a solid composition according to the invention has, at a temperature of 20 ⁇ and at atmospheric pressure (760 mm Hg), a hardness above 30 Nm 1 , and preferably above 40 Nm 1 .
  • the stick is preserved at 20 ⁇ for 24 hours before the hardness is measured.
  • the hardness can be measured at 20 °C by the so-called "butter cutter wire” method, which consists in transversally cutting a stick of product, preferably cylindrical, by means of a rigid tungsten wire having a diameter of 250 ⁇ while moving the wire with respect to the stick at a speed of 100 mm/min.
  • the hardness of the samples of compositions of the invention is measured by means of a DFGS2 dynamometer sold by the INDELCO- CHATILLON company. The measurement is reproduced three times, then averaged. The average of the three values read by means of the dynamometer mentioned above, denoted Y, is given in grams. This average is converted into Newton then divided by L, which represents the largest dimension passed through by the wire. In the case of a cylindrical stick, L is equal to the diameter (in meters).
  • the stick For a measurement at a different temperature, the stick is kept for 24 hours at this new temperature before the measurement.
  • the composition according to the invention has a hardness at 20 q C, greater than or equal to 30 Nm "1 , preferably greater than 40 Nm "1 , and preferably greater than 50 Nm "1 .
  • the composition according to the invention in particular has a hardness at 20 q C, below 500 Nm “1 , in particular below 400 Nm “1 , and preferably below 300 Nm “1 .
  • a composition of which the hardness is greater than 30 Nm "1 is a so-called “solid” composition at 20 ⁇ and at atmospheric pressure (760 mm Hg).
  • physiologically acceptable medium we mean a medium that is particularly suitable for the application of a composition of the invention on the skin and lips, such as the organic solvents or oils commonly used in cosmetic compositions.
  • the physiologically acceptable medium is generally suitable (acceptable tolerance, toxicology and feel) for the nature of the support to which the composition is to be applied, as well as the way in which the composition is to be packaged.
  • a composition according to the invention comprises at least alkylcellulose, the alkyl portion being in particular C 2 -C 4 .
  • the alkylcellulose is chosen from ethylcellulose, propylcellulose, and according to one particularly advantageous embodiment, the alkylcelluose is ethylcellulose.
  • the alkylcellulose is present in the composition according to the invention in a dry matter content greater than or equal to 2% by weight with respect to the total weight of said composition, preferably ranging from 2% to 30% by weight, preferably between 2% and 20% by weight, with respect to the total weight of said composition.
  • the alkylcellulose content expressed by dry matter content, varies from 5% to 20% by weight with respect to the total weight of the composition.
  • the alkylcellulose content expressed by dry matter content, varies from 2% to 10% by weight with respect to the total weight of the composition.
  • alkylcellulose is present in the stable and homogeneous dispersion state, i.e. in a dispersed form in the composition according to the invention.
  • the alkylcellulose is a C 2 -C 4 aliphatic ether of cellulose, in particular ethyl ether in the case of ethylcellulose, comprising a chain consisting of ⁇ - anhydroglucose units linked to one another by acetal bonds.
  • Each anhydroglucose unit has three replaceable hydroxyl groups, all or some of these hydroxyl groups being capable of reacting according to the following reaction:
  • R represents a cellulose radical and R' represents a C 2 -C 4 alkyl radical, preferably C 2 H 5 .
  • the total substitution of the three hydroxyl groups would lead, for each anhydroglucose unit, to a degree of substitution of 3, in other words, to an alkoxy group, in particular ethoxy group, content of 54.88%.
  • the alkylcellulose, in particular ethylcellulose, polymers used in a cosmetic composition according to the invention are preferably polymers having a degree of substitution of alkoxy groups, preferably ethoxy groups, ranging from 2.5 to 2.6 per anhydroglucose unit, in other words, comprising an alkoxy group, and preferably ethoxy group, content ranging from 44% to 50%.
  • the alkylcellulose used in the preparation of a composition according to the invention can be in powder form.
  • alkylcellulose polymers that may be used in a composition according to this invention, mention may be made very specifically of the products sold by the HERCULES, Inc. company (Wilmington, Del.), under the name "Aqualon ® Ethylcellulose”.
  • the different ethylcellulose polymers are also specified with regard to the measured viscosity of a 5% by weight solution of ethylcellulose in a toluene: ethanol mixture (80:20).
  • the product "Aqualon K100 Ethylcellulose” refers to the ethylcellulose polymer of type K, i.e. comprising 45 to 47.2% ethoxy groups (or a degree of substitution of ethoxy groups per anhydroglucose unit ranging from 2.22 to 2.41 ), and having, at 5% by weight in a toluene: ethanol mixture (80:20), an average viscosity of 100 mPa.s.
  • the alkylcellulose used in a composition according to the invention is an ethylcellulose polymer comprising a degree of substitution of ethoxy groups per anhydroglucose unit ranging from 2.46 to 2.57.
  • the ethylcellulose used in a composition according to the invention is an ethylcellulose polymer having, in particular, a viscosity at 5% by weight in a toluene: ethanol mixture (80:20) at 25 °C of between 3 and 350 mPa.s.
  • the ethylcellulose used in a composition according to the invention is an ethylcellulose polymer having, in particular, a viscosity at 5% by weight in a toluene: ethanol mixture (80:20) at 25 °C of between 3 and 105 mPa.s.
  • the ethylcellulose used in a composition according to the invention is an ethylcellulose polymer having, in particular, a viscosity at 5% by weight in a toluene: ethanol mixture (80:20) at 25 °C of between 3 and 24 mPa.s.
  • the ethylcellulose used in a composition according to the invention is an ethylcellulose polymer having, in particular, a viscosity at 5% by weight in a toluene: ethanol mixture (80:20) at 25 °C of between 3 and 8 mPa.s.
  • the ethylcellulose used in a composition according to the invention is an ethylcellulose polymer having, in particular, a viscosity at 5% by weight in a toluene: ethanol mixture (80:20) at 25 °C of between 3 and 5.5 mPa.s.
  • ethylcelluloses of type N or T are preferred, preferably type N, sold by the Aqualon company.
  • the ethylcellulose used in a composition according to the invention is the product sold by Aqualon under the name "Aqualon N4 Ethylcellulose”.
  • the ethylcellulose used in a composition according to the invention is an ethylcellulose polymer having, in particular, a viscosity at 5% by weight in a toluene: ethanol mixture (80:20) at 25 ⁇ of between 3 and 6 mPa.s.
  • compositions according to the invention comprise at least one branched dextrin ester. They can therefore comprise a single branched dextrin ester or a mixture of different branched dextrin esters.
  • branched dextrin ester refers to a dextrin modified by esterification by at least one branched chain fatty acid. It is also possible to designate this branched dextrin ester by the term "branched fatty acid and dextrin ester” or "branched fatty acid dextrin ester” or "dextrin esterified by at least one branched fatty acid”. According to one embodiment, the branched dextrin ester is a dextrin esterified by at least one fatty acid.
  • the dextrin more specifically has an average degree of glucose polymerization of 3 to 150, and preferably 10 to 100.
  • the fatty acid(s) comprise 50% to 100% in moles, preferably 55% to 100% in moles, on the basis of the total amount of fatty acid(s), one or more branched saturated fatty acids having 4 to 26 carbon atoms, more advantageously having 12 to 22 carbon atoms, and 0% to less than 50% in moles, preferably from 0 to 45% in moles, on the basis of the total amount of fatty acid(s), one or more other fatty acids chosen from the group consisting of the linear saturated fatty acids having 2 to 22 carbon atoms, the unsaturated linear or branched fatty acids having 6 to 30 carbon atoms, and the saturated or unsaturated cyclic fatty acids having 6 to 30 carbon atoms.
  • the degree of substitution of dextrin by the fatty acid(s) is 1 .0 to 3.0 per glucose unit.
  • saturated branched fatty acids having 4 to 26 carbon atoms mention may be made of isobutyric acid, isovaleric acid, 2-ethylbutyric acid, ethylmethylacetic acid, isoheptanoic acid, 2-ethylhexanoic acid, isononanoic acid, isodecanoic acid, isotridecanoic acid, isomyristic acid, isopalmitic acid, isostearic acid, isoarachic acid, and isohexacosanoic acid or mixtures thereof.
  • the acid chosen is isostearic acid.
  • saturated linear fatty acids having 2 to 22 carbon atoms mention may be made of the acetic, caprylic, capric, lauric, myristic, palmitic, stearic, arachidic, and behenic acids or mixtures thereof.
  • the linear fatty acids having 8 to 22 carbon atoms are preferable, and even more specifically those having 12 to 22 carbon atoms.
  • the unsaturated mono-acids such as cis-4- decenoic, 9-decenoic, cis-4-dodecenoic, cis-4-tetradecenoic, cis-5-tetradecenoic, cis-9-tetradecenoic, cis-6-hexadecenoic, cis-9-hexadecenoic, cis-9-octadecenoic, trans-9-octadecenoic, cis-1 1 -octadecenoic, cis-1 1 -eicosenoic, cis-17-hexacosenoic and cis-21 -triacontenoic acids; the polyunsaturated acids such as sorbic, linoleic, hiragonic, punicic, linolenic, stearidonic,
  • saturated or unsaturated acids having a cyclic structure in at least a portion of the base skeleton and having 6 to 30 carbon atoms are suitable, such as, for example, 9,10-methylene-9-octadecenoic, aleprylic, alepric, gorlic, [alpha] cyclopentylic, [alpha] cyclohexylic, [alpha] cyclopentylethylic, [alpha] cyclohexylmethylic, [omega] cyclohexylic, 5 (6)-carboxy-4-hexyl-2-cyclohexene-1 - octanoic, malvalic, sterculynic, hydnocarpic and chaulmoogric acids or mixtures thereof.
  • the branched dextrin ester used according to the invention can therefore comprise one esterified chain or a plurality of esterified chains, identical or different. It can, for example, be a dextrin esterified by a plurality of identical or different fatty acids.
  • dextrin esters can be prepared by using conventional esterification methods.
  • Dextrin having an average degree of glucose polymerization of 3 to 150 is reacted with one or more branched fatty acid derivatives as well as with, as the case may be, one or more derivatives of other fatty acids, in the proportions required for obtaining the dextrin ester described above.
  • Dextrin having an average degree of glucose polymerization of 3 to 150 is reacted in a first step, with one or more branched fatty acid derivatives, then in a second step, with one or more derivatives of one or more of the other fatty acids, in the proportions required for obtaining the dextrin ester described above.
  • acid anhydrides and halides are used as fatty acid derivatives.
  • dextrin is dispersed in a reaction solvent, and a catalyst is added to it, if necessary.
  • This mixture is reacted by adding the aforementioned fatty acid derivatives, preferably halides.
  • these derivatives are mixed and added simultaneously to the reaction mixture, and in method 2), the derivatives are introduced successively.
  • dimethylformamide As a common solvent, mention may be made of dimethylformamide, formamide, acetamide, ketones, aromatic compounds such as benzene, toluene, xylene, dioxane, or mixtures thereof.
  • the suitable catalysts are normally chosen from the tertiary amine compounds such as pyridine or picoline.
  • the reaction temperature is generally chosen on the basis of the starting derivatives of the fatty acid(s). It is generally between 0 and ⁇ ⁇ ' ⁇ .
  • the dextrin esters are then purified as usual.
  • the amount of branched dextrin ester in a composition according to the invention is between 5% and 25% by weight with respect to the total weight of said composition.
  • the percentage of branched dextrin ester is between 5% and 20% by weight with respect to the total weight of the composition, and more specifically between 10% and 15% by weight with respect to the total weight of said composition.
  • the branched dextrin ester content is advantageously between 15% and 25% by weight with respect to the total weight of said composition.
  • the branched dextrin ester is dextrin isostearate, dextrin isoarachidate, dextrin isopalmitate, dextrin isononanoate, as well as mixtures thereof.
  • the branched dextrin ester is dextrin isostearate.
  • compositions according to the invention also comprise at least one fatty alcohol as defined above. They can therefore comprise a single fatty alcohol or a mixture of different fatty alcohols.
  • the fatty alcohols used according to this invention can be represented by the formula ROH, R representing a saturated or unsaturated, linear or branched hydrocarbon radical comprising at least 8 carbon atoms, more specifically comprising 8 to 30 carbon atoms.
  • the radical R mentioned above is a saturated or unsaturated, linear or branched hydrocarbon radical comprising 8 to 30 and in particular 10 to 26, and preferably 14 to 22 carbon atoms.
  • fatty alcohols that may be used according to the invention, mention may be made of the linear or branched fatty alcohols, of synthetic or natural origin, such as, for example, alcohols obtained from plant matter (copra, oil palm, palmate) or animal matter (tallow).
  • long-chain alcohols can also be used, such as, for example, ether alcohols or so-called Guerbet alcohols.
  • the fatty alcohol is octyldodecanol.
  • the amount of fatty alcohol in the composition according to the invention is between 10% and 70% by weight with respect to the total weight of said composition, preferably between 15% and 30% by weight with respect to the total weight of said composition for a solid form.
  • this content is preferably between 40% and 60% by weight with respect to the total weight of said composition.
  • compositions according to the invention can also comprise, in addition to the compositions indicated above, namely alkylcellulose, and preferably ethylcellulose, a branched dextrin ester and a fatty alcohol, at least one non-volatile oil, different from the aforementioned fatty alcohol.
  • compositions according to the invention can comprise a non-volatile oil or a mixture of a plurality of non-volatile oils.
  • the non-volatile oil(s) are more specifically chosen from non-volatile phenylated or non-phenylated silicone oils, non-volatile polar or non-polar hydrocarbon oils, or mixtures thereof.
  • the non-volatile oil is chosen from the group consisting of silicone oils, phenylated silicone oils, hydrocarbon silicon oils, non-polar or polar, and mixtures thereof.
  • “Non-volatile” means an oil of which the vapor pressure at 25°C and atmospheric pressure is different from zero and below 0.02 mm Hg (2.66 Pa) and preferably below 10 ⁇ 3 mm Hg (0.13 Pa).
  • the non-volatile oil content is at least 5% by weight with respect to the total weight of the composition, and advantageously at least 8% by weight.
  • the non-volatile oil content is between 10% and 50% by weight, with respect to the weight of the composition, and even more specifically between 20% and 45% by weight, with respect to the weight of the composition.
  • Silicon oil refers to an oil containing at least one silicon atom, and in particular containing Si-0 groups.
  • non-phenylated silicone oil or “non-phenylated silicone oil” refers to a silicone oil not having a phenyl substituent.
  • non-phenylated non-volatile silicone oils examples include polydimethylsiloxanes, alkyldimethicones, vinylmethylmethicones, and also silicones modified with aliphatic groups and/or with functional groups such as hydroxyl, thiol and/or amine groups.
  • dimethylsiloxane (INCI name) corresponds to a polydimethylsiloxane (chemical name).
  • the non-phenylated non-volatile silicone oil is preferably chosen from the nonvolatile dimethicone oils.
  • oils can be chosen from the following non-volatile oils:
  • - PDMS comprising aliphatic groups, in particular alkyl, or alkoxy groups, that are pendant or at the end of the silicone chain; these groups each comprise 2 to 24 carbon atoms.
  • cetyl dimethicone sold under the trade name ABIL WAX 9801 of Evonik Goldschmidt,
  • - PDMS including aliphatic groups, or functional groups such as hydroxyl, thiol and/or amine groups,
  • these non-phenylated non-volatile silicone oils are chosen from polydimethylsiloxanes, alkyldimethicones and also PDMS including aliphatic groups, in particular C 2 -C 2 4 alkyl and/or functional groups such as hydroxyl, thiol and/or amine groups.
  • the non-phenylated silicone can be chosen in particular from silicones of formula (I):
  • Ri , R 2 , 5 and R 6 are, together or separately, an alkyl radical containing 1 to 6 carbon atoms,
  • R 3 and R 4 are, together or separately, an alkyl radical containing 1 to 6 carbon atoms, a vinyl radical, an amine radical or a hydroxyl radical,
  • X is an alkyl radical containing 1 to 6 carbon atoms, a hydroxyl radical or an amine radical,
  • n and p are integers chosen so as to have a fluid compound, in particular of which the viscosity at 25°C is between 9 centistokes (cSt) (9 x 10 ⁇ 6 m 2 /s) and 800,000 cSt.
  • non-phenylated non-volatile silicone oils that can be used according to the invention, mention may be made of those for which:
  • the substituents Ri to R 6 and X represent a methyl group
  • p and n are such that the viscosity is 500,000 cSt, for example the product sold under the name SE30 by the General Electric company, the product sold under the name AK 500,000 by the Wacker company, the product sold under the name Mirasil DM 500,000 by the Bluestar company, and the product sold under the name Dow Corning 200 Fluid 500,000 cSt by the Dow Corning company,
  • the substituents Ri to R 6 and X represent a methyl group
  • p and n are such that the viscosity is 60,000 cSt, for example the product sold under the name Dow Corning 200 Fluid 60,000 CS by the Dow Corning company, and the product sold under the name Wacker Belsil DM 60,000 by the Wacker company,
  • the substituents Ri to R 6 and X represent a methyl group, and p and n are such that the viscosity is 100 cSt, or 350 cSt, for example the products sold under the names, respectively, Belsil DM100, Dow Corning 200 Fluid 350 CS, by the Dow Corning company,
  • the substituents Ri to R 6 represent a methyl group
  • group X represents a hydroxyl group
  • n and p are such that the viscosity is 700 cSt, for example the product sold under the name Baysilone Fluid TO.7 by the Momentive company.
  • phenylated silicone oil or "phenyl silicone oil” refers to a silicone oil having at least one phenyl substituent.
  • non-volatile phenylated silicone oils can be chosen from those having, in addition, at least one dimethicone fragment, or from those not having one.
  • a dimethicone fragment corresponds to the following unit: -Si(CH 3 ) 2 -0-.
  • the non-volatile phenylated silicone oil can thus be chosen from: a) the phenyl silicone oils having or not having a dimethicone fragment corresponding to the following formula (I):
  • R groups monovalent or divalent, represent, independently of one another, a methyl or a phenyl, on the condition that at least one R group represents a phenyl.
  • the phenyl silicone oil comprises at least three phenyl groups, for example at least four, at least five or at least six groups.
  • the phenyl silicone oils having or not having a dimethicone fragment corresponding to the following formula (2) :
  • R I R I R I (II) wherein the R groups represent, independently of one another, a methyl or a phenyl, on the condition that at least one R group represents a phenyl.
  • the compound of formula (I I) comprises at least three phenyl groups, for example at least four or at least five groups.
  • Examples that may be mentioned include triphenyl-, tetraphenyl- or pentaphenyl-organopolysiloxane mixtures.
  • Such non-volatile phenyl silicone oils are preferably trimethylpentaphenyl- trisiloxane, or tetramethyl-tetraphenyl-trisiloxane. They are in particular sold by Dow Corning under the name PH-1 555 HRI or Dow Corning 555 Cosmetic Fluid (chemical name: 1 ,3,5-trimethyl-1 , 1 ,3,5,5-pentaphenyltrisiloxane; INCI name: trimethyl-pentaphenyltrisiloxane), or tetramethyl-tetraphenyl-trisiloxane sold under the name Dow Corning 554 Cosmetic Fluid by Dow Corning can also be used.
  • Me represents methyl and Ph represents phenyl.
  • compositions according to the invention include trimethylpentaphenyl-trisiloxane.
  • phenyl silicone oils having at least one dimethicone fragment corresponding to the following formula (IV):
  • - Ri to Rio independently of one another, are saturated or unsaturated, linear, cyclic or branched C C 30 hydrocarbon radicals,
  • n, p and q are, independently of one another, integers between 0 and 900, on the condition that the sum m+n+q is different from 0.
  • the sum m+n+q is between 1 and 100.
  • the sum m+n+p+q is between 1 and 900 and preferably between 1 and 800.
  • q is equal to 0.
  • Ri to Ri 0 independently of one another, represent a linear or branched, saturated or unsaturated, preferably saturated Ci-C 30 hydrocarbon radical, and in particular a preferably saturated Ci-C 20 , in particular C Ci 8 , hydrocarbon radical, or monocyclic or polycyclic C 6 -Ci 4 and in particular Ci 0 -Ci 3 aryl radical, or an aralkyl radical, preferably in which the alkyl portion is C C 3 .
  • Ri to R 0 can each represent a methyl, ethyl, propyl, butyl, isopropyl, decyl, dodecyl or octadecyl radical, or alternatively a phenyl, tolyl, benzyl or phenethyl radical.
  • Ri to R 0 can in particular be identical, and can also be a methyl radical. According to a more specific embodiment of formula (V), mention may be made of:
  • R 6 independently of one another, are saturated or unsaturated, linear, cyclic or branched CrC 30 hydrocarbon radicals, an aryl radical, preferably C 6 -Ci 4 , or an aralkyl radical of which the alkyl portion is CrC 3 ,
  • n and p are, independently of one another, integers between 0 and 100, on the condition that the sum n+m is between 1 and 100.
  • Ri to R 6 independently of one another, represent a hydrocarbon radical, preferably a Ci-C 20 , in particular Ci-Ci 8 alkyl, or a monocyclic (preferably C 6 ) or polycyclic C 6 -Ci 4 aryl radical, and in particular Ci 0 -Ci 3 , or an aralkyl radical (preferably the aryl portion is C 6 ; the alkyl portion is CrC 3 ).
  • a hydrocarbon radical preferably a Ci-C 20 , in particular Ci-Ci 8 alkyl, or a monocyclic (preferably C 6 ) or polycyclic C 6 -Ci 4 aryl radical, and in particular Ci 0 -Ci 3 , or an aralkyl radical (preferably the aryl portion is C 6 ; the alkyl portion is CrC 3 ).
  • Ri to R 6 can each represent a methyl, ethyl, propyl, butyl, isopropyl, decyl, dodecyl or octadecyl radical, or alternatively a phenyl, tolyl, benzyl or phenethyl radical.
  • Ri to R 6 can in particular be identical, and can also be a methyl radical.
  • m 1 or 2 or 3
  • the non-volatile phenylated silicone oil is chosen from the phenylated silicone oils having at least one dimethicone fragment.
  • oils correspond to compounds of formula (VI) wherein:
  • n and p are, independently of one another, integers between 1 and 100.
  • Ri to R 6 are methyl radicals.
  • the silicone oil is preferably chosen from a diphenyldimethicone such as KF-54 of Shin Etsu (400 cSt), KF54HV of Shin Etsu (5000 cSt), KF-50-300CS of Shin Etsu (300 cSt), KF-53 of Shin Etsu (175cSt), KF- 50-100CS of Shin Etsu (100 cSt).
  • a diphenyldimethicone such as KF-54 of Shin Etsu (400 cSt), KF54HV of Shin Etsu (5000 cSt), KF-50-300CS of Shin Etsu (300 cSt), KF-53 of Shin Etsu (175cSt), KF- 50-100CS of Shin Etsu (100 cSt).
  • phenyl silicone oils have or do not have at least one dimethicone fragment corresponding more specifically to formula (VII) below:
  • p is between 1 and 1000, and m is more specifically such that the compound (VII) is a non-volatile oil.
  • VII trimethylsiloxyphenyl dimethicone
  • p is equal to 0
  • m is between 1 and 1000, and in particular, is such that the compound (VII) is a non-volatile oil.
  • the Rs independently of one another, are saturated or unsaturated, linear, cyclic or branched Ci-C 30 hydrocarbon radicals, preferably R is a Ci-C 30 alkyl radical, an aryl radical, preferably C 6 -Ci 4 , or an aralkyl radical of which the alkyl portion is C C 3 ;
  • n are, independently of one another, integers between 0 and 100, on the condition that the sum n+m is between 1 and 100.
  • the Rs independently of one another, represent a saturated or unsaturated, linear or branched, preferably saturated C C 30 hydrocarbon radical, and in particular a preferably saturated CrC 20 , in particular C Ci 8 and more specifically C 4 -Ci 0 hydrocarbon radical, a monocyclic or polycyclic C 6 -C and in particular Ci 0 -Ci 3 aryl radical, or an aralkyl radical (preferably the aryl portion is C 6 and the alkyl portion is C C 3 ).
  • the Rs can each represent a methyl, ethyl, propyl, butyl, isopropyl, decyl, dodecyl or octadecyl radical, or alternatively a phenyl, tolyl, benzyl or phenethyl radical.
  • the Rs can in particular be identical, and in addition may be a methyl radical.
  • m 1 or 2 or 3
  • n is an integer between 0 and 100 and m is an integer between 1 and 100, on the condition that the sum n+m is between 1 and 100, in formula (VIII).
  • R is a methyl radical.
  • a phenyl silicone oil of formula (VIII) having a viscosity at 25 °C between 5 and 1500 mm 2 /s (i.e. 5 to 1500 cSt), and preferably having a viscosity between 5 and 1000 mm 2 /s (i.e. 5 to 1000 cSt) can be used.
  • diphenylsiloxy phenyl trimethicone oil when m and n are between 1 and 100
  • KF56 A of Shin Etsu the oil Silbione 70663V30 of Rhone-Poulenc (28 cSt).
  • the values between parentheses represent the viscosities at 25 ⁇ .
  • compositions according to the invention include phenyltrimethicone.
  • the phenyl silicone oils have or do not have at least one dimethicone fragment corresponding to the following formula, and mixtures thereof:
  • Ri , R 2 , R 5 and R 6 are, identical or not, an alkyl radical containing 1 to 6 carbon atoms,
  • R 3 and R 4 are, identical or not, an alkyl radical containing 1 to 6 carbon atoms or an aryl radical (preferably C 6 -Ci 4 ), on the condition that at least one of R 3 and R 4 is a phenyl radical,
  • X is an alkyl radical containing 1 to 6 carbon atoms, a hydroxyl radical or a vinyl radical,
  • n and p being an integer greater than or equal to 1 , chosen so as to give the oil a mean molar mass by weight below 200,000 g/mole, preferably below 150,000 g/mole and more preferably below 100,000 g/mole.
  • Fluorinated oil refers to an oil containing at least one fluorine atom.
  • fluorinated oils mention may be made of fluorosilicone oils, fluorinated polyethers, fluorinated silicones in particular as described in document EP-A-847752 and perfluorinated compounds.
  • Perfluorinated compounds are compounds of which all of the hydrogen atoms have been substituted with fluorine atoms.
  • the fluorinated oil is chosen from the perfluorinated oils.
  • perfluorinated oils mention may be made of perfluorodecalins and perfluoroperhydrophenanthrenes.
  • the fluorinated oil is chosen from the perfluoroperhydrophenanthrenes, and in particular the Fiflow ® products sold by the Creations Couelles company.
  • the fluorinated oil the INCI name of which is perfluoroperhydrophenanthrene, sold under the name FIFLOW 220 by the F2 Chemicals company.
  • Non-volatile polar hydrocarbon oils are non-volatile polar hydrocarbon oils.
  • Hydrocarbon oil refers to an oil essentially formed by, or consisting of, carbon and hydrogen atoms, and optionally oxygen and nitrogen atoms, and not containing silicon or fluorine atoms.
  • It may contain alcohol, ester, ether, carboxylic acid, amine and/or amide groups.
  • the hydrocarbon oils is free, aside from silicon, of fluorine, heteroatoms such as N, Si and P.
  • the hydrocarbon oil is therefore distinct from a silicon oil and a fluorinated oil.
  • the non-volatile hydrocarbon oil includes at least one oxygen atom.
  • this non-volatile hydrocarbon oil includes at least one alcohol function (it is thus an “alcohol oil”) and/or at least one ester function (it is thus an “ester oil”).
  • ester oils that may be used in the compositions according to the invention can in particular be hydroxylated.
  • composition can include one or more non-volatile hydrocarbon oils, in particular chosen from:
  • triesters of a C 2 -C 8 carboxylic triacid and a C 2 -C 8 alcohol optionally hydroxylated, such as citric acid esters, such as trioctyl citrate, triethylcitrate, acetyltributyl citrate, tributyl citrate and acetyltributyl citrate,
  • citric acid esters such as trioctyl citrate, triethylcitrate, acetyltributyl citrate, tributyl citrate and acetyltributyl citrate
  • esters of a C 2 -C 8 polyol and one or more C 2 -C 8 carboxylic acids such as glycol diesters, and monoacids, such as neopentyl glycol diheptanoate, or glycol triesters and monoacids such as triacetin.
  • ester oils in particular having between 18 and 70 carbon atoms.
  • the ester oils may or may not be hydroxylated.
  • the non-volatile ester oil can be chosen, for example, from:
  • Ri represents the radical of a linear or branched or aromatic fatty acid comprising 4 to 40 saturated or unsaturated carbon atoms
  • R 2 represents a hydrocarbon chain, in particular branched, containing 4 to 40 carbon atoms on the condition that Ri + R 2 is > 18, such as, for example, Purcellin oil (cetostearyl octanoate), isononyl isononanoate, Ci 2 to C15 alcohol benzoate, 2-ethylhexyl palmitate, octyldodecyl neopentanoate, 2- octyldodecyl stearate, 2-octyldodecyl erucate, isostearyl isostearate, 2-octyldodecyl benzoate, octanoates, decanoates or ricino
  • esters of formula RiCOOR 2 wherein represents the radical of a linear or branched fatty acid comprising 4 to 40 carbon atoms and R 2 represents a hydrocarbon chain, in particular branched, containing 4 to 40 carbon atoms, Ri and R 2 being such that Ri + R 2 is > 18.
  • the ester comprises between 18 and 40 carbon atoms in total.
  • monoesters mention may be made of isononyl isononanoate, oleyl erucate and/or 2-octyldodecyl neopentanoate; * fatty acid monoesters, in particular with 18 to 22 carbon atoms, and in particular lanolic acid, oleic acid, lauric acid, stearic acid, and diols, such as propylene glycol monoisostearate.
  • diesters in particular comprising between 18 and 60 carbon atoms in total, in particular between 18 and 50 carbon atoms in total. It is possible in particular to use dicarboxylic acid diesters and monoalcohols, such as, preferably, diisostearyl malate, or glycol diesters and monocarboxylic acid diesters, such as neopentylglycol diheptanoate, propylene glycol dioctanoate, diethyleneglycol diisononanoate, or polyglyceryl-2 diisostearate (in particular such as the compound sold under the trade name DERMOL DGDIS by the Alzo company);
  • dicarboxylic acid diesters and monoalcohols such as, preferably, diisostearyl malate, or glycol diesters and monocarboxylic acid diesters, such as neopentylglycol diheptanoate, propylene glycol dioctanoate, diethyleneglycol
  • hydroxylated monoesters and diesters preferably having a total carbon number ranging from 18 to 70, such as polyglyceryl-3 diisostearate, isostearyl lactate, octyl hydroxystearate, octyldodecyl hydroxystearate, diisostearyl malate, glycerine stearate;
  • triesters in particular comprising between 35 and 70 carbon atoms in total, in particular such as tricarboxylic acid triesters, such as triisostearyl citrate, or tridecyl trimellitate, or glycol and monocarboxylic acid triesters such as polyglycerol- 2 triisostearate;
  • tricarboxylic acid triesters such as triisostearyl citrate, or tridecyl trimellitate
  • glycol and monocarboxylic acid triesters such as polyglycerol- 2 triisostearate
  • tetraesters in particular having a total carbon number ranging from 35 to 70, such as pentaerythritol or polyglycerol tetraesterse and a monocarboxylic acid, for example such as pentaerythrityl tetrapelargonate, pentaerythrityl tetraisostearate, pentaerythrityl tetraisononanoate, glyceryl tri decyl-2 tetradecanoate, polyglyceryl-2 tetraisostearate or pentaerythrityl tetra decyl-2 tetradecanoate;
  • polyesters obtained by condensation of unsaturated fatty acid dimers and/or trimers and diol such as those described in patent application FR 0 853 634, such as, in particular dilinoleic acid and 1 ,4-butanediol. Mention may particularly be made in the respect of the polymer sold by Biosynthis under the name Viscoplast 14436H (INCI name: dilinoleic acid/butanediol copolymer), or the polyol and dimer diacid copolymers, and esters thereof, such as Hailucent ISDA ;
  • dimer diol and mono or dicarboxylic acid esters such as diol dimer and fatty acid esters and diol dimer and dicarboxylic acid dimer esters, in particular capable of being obtained from a dicarboxylic acid dimer derived in particular from the dimerization of an unsaturated fatty acid, in particular C 8 to C 34 , in particular C 12 to C 22 , in particular Ci 6 to C 20 , and more specifically Ci 8 , such as esters of dilinoleic diacid and dilinoleic diol dimers, for example those sold by the NIPPON FINE CHEMICAL company under the trade name LUSPLAN DD-DA5 ® and DD-DA7 ® ; * the polyesters resulting from the esterification of at least one hydroxylated carboxylic acid triglyceride by an aliphatic monocarboxylic acid and by an aliphatic dicarboxylic acid, optionally unsaturated, such as castor oil
  • hydrocarbon plant oils such as fatty acid triglycerides (liquid at room temperature), in particular fatty acids having 7 to 40 carbon atoms, such as heptanoic or octanoic acid triglycerides or jojoba oil, in particular, and mention may be made of saturated triglycerides such as caprylic/capric triglyceride and mixtures thereof, for example such as that sold under the name Myritol 318 of Cognis, glyceryl triheptanoate, glycerine trioctanoate, ⁇ 8 - 36 acid triglycerides such as those sold under the name DUB TGI 24 sold by Stearineries Dubois), and unsaturated triglycerides such as castor oil, olive oil, ximenia oil and pracaxi oil.
  • saturated triglycerides such as caprylic/capric triglyceride and mixtures thereof, for example such as that sold under the name Myritol
  • Ci 2 -C 26 preferably Ci 2 -C 22 , preferably unsaturated fatty acids, such as oleic acid, linoleic acid, linolenic acid and mixtures thereof.
  • dialkyl carbonates the 2 alkyl chains being capable of being identical or different, such as dicaprylyl carbonate sold under the name Cetiol CC®, by Cognis.
  • Non-volatile non-polar hydrocarbon oils
  • composition according to the invention can also comprise at least one non-volatile non-polar hydrocarbon oil.
  • oils can be of plant, mineral or synthetic origin.
  • non-polar oil in the sense of this invention, is an oil of which the solubility parameter at 25 °C, 5 a , is equal to 0 (J/cm 3 ) 1 ⁇ 2 .
  • solubility parameters in the HANSEN three- dimensional solubility space are described in the article of C. M. HANSEN: "The three dimensional solubility parameters” J. Paint Technol. 39, 105 (1967).
  • the parameters ⁇ ⁇ , 5 h , 5 D and 5 a are expressed in (J/cm 3 ) 1 ⁇ 2 .
  • hydrocarbon oil is an oil essentially formed by, or consisting of, carbon and hydrogen atoms, and optionally oxygen and nitrogen atoms, and not containing silicon or fluorine atoms. It may contain alcohol, ester, ether, carboxylic acid, amine and/or amide groups.
  • non-volatile non-polar hydrocarbon oil can be chosen from the linear or branched hydrocarbons, of mineral or synthetic origin, such as:
  • Parleam ® sold by the NIPPON OIL FATS company
  • PANALANE H-300 E sold or manufactured by the AMOCO company
  • VISEAL 20000 sold or manufactured by the SYNTEAL company
  • REWOPAL PIB 1000 sold or manufactured by the WITCO company
  • PARLEAM LITE sold by the NOF Corporation
  • PURESYN 6 sold by EXXONMOBIL CHEMICAL
  • compositions according to the invention can also include at least one compound chosen from waxes, pasty fats, lipophilic gelling agents, fillers and mixtures thereof.
  • composition according to the invention can include at least one wax.
  • the composition when in liquid form, it includes at least one wax.
  • a “wax”, in the sense of the invention, is a lipophilic compound, solid at room temperature (25 ' ⁇ ), with a reversible change in solid/liquid state, having a melting point greater than or equal to 30 ' ⁇ and capable of reaching up to 120°C.
  • the waxes that may be used in a composition according to the invention are chosen from solid waxes, deformable or non-deformable at room temperature, of animal, plant, mineral or synthetic origin, and mixtures thereof.
  • hydrocarbon waxes such as beeswax, lanolin wax, and Chinese insect waxes
  • montan wax, microcrystalline waxes, paraffins and ozokerite polyethylene waxes, waxes obtained by Fisher-Tropsch synthesis and waxy copolymers as well as esters thereof.
  • compositions according to the invention include microcrystalline wax.
  • compositions according to the invention include ozokerite.
  • compositions according to the invention include polyethylene wax.
  • waxes obtained by catalytic hydrogenation of animal or plant oils having linear or branched C 8 -C 32 fatty chains Mention may also be made of waxes obtained by catalytic hydrogenation of animal or plant oils having linear or branched C 8 -C 32 fatty chains.
  • hydrogenated jojoba oil hydrogenated sunflower oil, hydrogenated castor oil, hydrogenated coconut oil and hydrogenated lanolin oil
  • di-(trimethylol-1 ,1 ,1 propane) tetrastearate sold under the name "HEST 2T-4S” by the HETERENE company
  • di-(trimethylol-1 ,1 ,1 propane) tetrabehenate sold under the name HEST 2T-4B by the HETERENE company.
  • waxes obtained by transesterification and hydrogenation of plant oils such as castor or olive oil, such as waxes sold under the names Phytowax Castor 16L64 ® and 22L73 ® and Phytowax Olive 18L57 by the SOPHIM company.
  • plant oils such as castor or olive oil
  • Such waxes are described in the application FR-A-2792190.
  • silicone waxes which may advantageously be substituted polysiloxanes, preferably with a low melting point.
  • the silicone waxes that can be used may also be alkyl or alkoxy-dimethicones such as the following commercial products: Abilwax 2428, 2434 and 2440 (GOLDSCHMIDT), or VP 1622 and VP 1621 (WACKER), as well as (C 20 -C 60 ) alkyl- dimethicones, in particular (C30-C45) alkyl-dimethicones such as silicone wax sold under the name SF-1642 by the GE-Bayer Silicones company.
  • alkyl or alkoxy-dimethicones such as the following commercial products: Abilwax 2428, 2434 and 2440 (GOLDSCHMIDT), or VP 1622 and VP 1621 (WACKER), as well as (C 20 -C 60 ) alkyl- dimethicones, in particular (C30-C45) alkyl-dimethicones such as silicone wax sold under the name SF-1642 by the GE-Bayer Silicones company.
  • hydrocarbon waxes modified by silicone or fluorine groups such as, for example: siliconyl candelilla, siliconyl beeswax and Fluorobeeswax of Koster Keunen.
  • the waxes can also be chosen from the fluorinated waxes.
  • the wax or waxes may be present in an amount ranging from 1 % to 20% by weight, in particular from 1 % to 10% by weight, with respect to the total weight of the composition.
  • composition according to the invention can also comprise at least one pasty fat.
  • a “pasty fat”, in the sense of this invention, is a lipophilic fat compound with a reversible change in solid/liquid state, having, in the solid state, an anisotropic crystalline organization, and comprising, at a temperature of 23 °C a liquid fraction and a solid fraction.
  • the beginning melting point of the pasty compound may be below 23 °C.
  • the liquid fraction of the pasty compound measured at 23 °C may represent 9% to 97% by weight of the compound.
  • This liquid fraction at 23 ⁇ preferably represents between 15% and 85%, more preferably between 40% and 85% by weight.
  • the melting point corresponds to the temperature of the most endothermic peak observed in thermal analysis (DSC) as described in ISO standard 1 1357-3; 1999.
  • the melting point of a paste or a wax may be measured by means of a differential scanning calorimeter sold under the name "MDSC 2920" by the TA Instruments company.
  • the measurement protocol is as follows:
  • a sample of 5 mg of paste or wax (depending on the case) arranged in a crucible is subjected to a first temperature rise from -20 °C to 100°C, at a heating rate of 10 ⁇ /minute, then is cooled from l OO'C to -20 °C at a cooling rate of 10°C/minute and finally subjected to a second temperature rise from -20 ⁇ to l OO 'C at a heating rate of 5 ⁇ /minute.
  • the variation in the difference in power absorbed by the empty crucible and by the crucible containing the paste or wax sample is measured as a function of temperature.
  • the liquid fraction by weight of the pasty compound at 23 ⁇ is equal to the ratio of the enthalpy of fusion consumed at 23 ⁇ to the enthalpy of fusion of the pasty compound.
  • the enthalpy of fusion of the pasty compound is the enthalpy consumed by the compound in order to go from the solid sate to the liquid state.
  • the pasty compound is said to be in the solid state when its entire mass is in solid crystalline form.
  • the pasty compound is said to be in the liquid state when its entire mass is in liquid form.
  • the enthalpy of fusion of the pasty compound is equal to the area below the curve on the thermogram obtained by means of a differential scanning calorimeter (DSC), such as the calorimeter sold under the name MDSC 2920 by the TA Instrument company, with a temperature rise of 5 or 10 'C per minute, according to ISO standard 1 1357-3:1999.
  • DSC differential scanning calorimeter
  • the enthalpy of fusion of the pasty compound is the amount of energy necessary for causing the compound to change from the solid state to the liquid state. It is expressed in J/g.
  • the enthalpy of fusion consumed at 23 °C is the amount of energy absorbed by the sample in order to change from the solid state to its state at 23 ⁇ consisting of a liquid fraction and a solid fraction.
  • the liquid fraction of the pasty compound measured at 32 °C is preferably 30 to 100% by weight of the compound, preferably 50 to 100%, more preferably 60 to 100% by weight of the compound.
  • the temperature at the end of the melting range of the pasty compound is less than or equal to 32 °C.
  • the liquid fraction of the pasty compound measured at 32 ⁇ C is equal to the ratio of the enthalpy of fusion consumed at 32 ⁇ C to the enthalpy of fusion of the pasty compound.
  • the enthalpy of fusion consumed at 32 °C is calculated in the same way as the enthalpy of fusion consumed at 23 °C.
  • the pasty fat can be chosen from the synthetic compounds and the compounds of plant origin.
  • a pasty fat can be obtained by synthesis from starting products of plant origin.
  • lanolin and derivatives thereof such as lanolin alcohol, oxyethylenated lanonlins, acetylated lanoline, lanolin esters such as isopropyl lanolate, and oxypropylenated lanolins,
  • silicone polymer or non-polymer compounds such as high molecular weight polydimethylsiloxanes, polydimethysiloxanes with alkyl or alkoxy side chains having 8 to 24 carbon atoms, in particular stearyl dimethicones,
  • alkyl (meth)acrylate homo or copolymers preferably having a C 8 -C 3 o alkyl group
  • the pasty fat can be a polymer, in particular hydrocarbon.
  • a preferred silicone and fluorine-containing pasty fat is polymethyl-trifluoropropyl-methylalkyl-dimethylsiloxane, manufactured under the name X22-1088 by SHIN ETSU.
  • the composition advantageously includes a compatibilizing agent such as short-chain esters such as isodecyl neopentanoate.
  • liposoluble polyethers mention may be made in particular of ethylene oxide and/or propylene oxide copolymers with C 6 -C 30 alkylene oxides.
  • the weight ratio of ethylene oxide and/or propylene oxide with alkylene oxides in the copolymer is 5:95 to 70:30.
  • block copolymer comprising C 6 -C 3 o alkylene oxide blocks having a molecular weight ranging from 1000 to 10,000, for example a polyoxyethylene/polydodecylene glycol block copolymer such as ethers of dodecanediol (22 mol) and polyethylene glycol (45 oxyethylene or OE units) sold under the name ELFACOS ST9 by Akzo Nobel.
  • a polyoxyethylene/polydodecylene glycol block copolymer such as ethers of dodecanediol (22 mol) and polyethylene glycol (45 oxyethylene or OE units) sold under the name ELFACOS ST9 by Akzo Nobel.
  • esters the following are particularly preferred:
  • esters of a glycerol oligomer in particular the esters of diglycerol, in particular the condensates of adipic acid and of glycerol, for which a portion of the hydroxyl groups of the glycerols have reacted with a mixture of fatty acids such as stearic acid, capric acid, stearic acid, isostearic acid and 12-hydroxystearic acid, such as those in particular sold under the name Softisan 649 by the Sasol company;
  • Ci 6 - 4 o alcohol at least one Ci 6 - 4 o alcohol, at least one of the alcohols being a Guerbet alcohol, and
  • diacid dimer formed by at least one Ci 8 - 4 o unsaturated fatty acid, such as the ester of tall oil fatty acid dimer comprising 36 carbon atoms and a mixture i) of Guerbet alcohols comprising 32 carbon atoms and ii) behenyl alcohol; the ester of linoleic acid dimer and a mixture of two Guerbet alcohols, 2-tetradecyl- octadecanol (32 carbon atoms) and
  • a Guerbet alcohol is the reaction product of the Guerbet reaction, which is well known to a person skilled in the art. It is a reaction transforming a primary aliphatic alcohol into its ⁇ -alkylated dimer alcohol with loss of an equivalent of water.
  • the aliphatic carboxylic acids described above generally include 4 to 30 and preferably 8 to 30 carbon atoms.
  • hexanoic acid heptanoic acid, oxtanoic acid, 2-ethylhexanoic acid, nonanoic acid, decanoic acid, undecanoic acid, dodecanoic acid, tridecanoic acid, tetradecanoic acid, pentadecanoic acid, hexadecanoic acid, hexyldeconic acid, heptadecanoic acid, oxtadecanoic acid, isostearic acid, nonadecanoic acid, eicosanoic acid, isoarachidic acid, octyldodecanoic acid, heneicosanoic acid, docosanoic acid and mixtures thereof.
  • the aliphatic carboxylic acids are preferably branched.
  • the hydroxylated aliphatic carboxylic acid esters are advantageously obtained from a hydroxylated aliphatic carboxylic acid comprising 2 to 40 carbon atoms, preferably 10 to 34 carbon atoms and, better, 12 to 28 carbon atoms, and 1 to 20 hydroxyl groups, preferably 1 to 10 hydroxyl groups and, better, 1 to 6 hydroxyl groups.
  • the hydroxylated carboxylic acid esters are in particular chosen from:
  • esters partial or total, of saturated linear monohydroxylated aliphatic monocarboxylic acids
  • esters partial or total, of unsaturated monohydroxylated aliphatic monocarboxylic acids
  • esters partial or total, of saturated monohydroxylated aliphatic carboxylic polyacids
  • esters partial or total, of saturated polyhydroxylated aliphatic carboxylic polyacids
  • esters partial or total, of C 2 to Ci 6 aliphatic polyols having reacted with a mono- or polyhydroxylated aliphatic mono- or polycarboxylic acid
  • the pasty fat(s) may be present in an amount ranging from 0.5% to 30% by weight, in particular 1 % to 20% by weight, with respect to the total weight of the composition.
  • composition according to the invention may optionally comprise at least one volatile oil.
  • the volatile oil can in particular be a silicone oil, a fluorinated oil or a hydrocarbonated oil.
  • the volatile silicone oil can in particular be chosen from the silicone oils having a flash point ranging from 40 °C to 102 ⁇ ⁇ , preferably having a flash point greater than 55 ' ⁇ and less than or equal to ⁇ ' ⁇ , and preferably ranging from 65 °C to 95 ⁇ €.
  • cSt centistokes
  • a volatile silicone oil that may be used, mention may be made in particular of dimethicones with a viscosity of 5 and 6 cSt, octamethyl cyclotetrasiloxane, decamethyl cyclopentasiloxane, dodecamethyl cyclohexasiloxane, heptamethyl hexyltrisiloxane, heptamethyloctyl trisiloxane, hexamethyl disiloxane, octamethyl trisiloxane, decamethyl tetrasiloxane, dodecamethyl pentasiloxane, and mixtures thereof.
  • nonafluoromethoxybutane or perfluoromethylcyclopentane mention may be made of nonafluoromethoxybutane or perfluoromethylcyclopentane, and mixtures thereof.
  • non-polar volatile hydrocarbon oils are preferably used.
  • the additional non-polar volatile hydrocarbon oils can have a flash point ranging from 40 ⁇ to 102°C, preferably ranging from 40 °C to ⁇ ' ⁇ , and preferably ranging from 40 ⁇ € to 50 ⁇ €.
  • the additional volatile hydrocarbon oil(s) can in particular be chosen from the volatile hydrocarbon oils having 8 to 16 carbon atoms and mixtures thereof, in particular:
  • C 8 -Ci6 branched alkanes such as C 8 -Ci 6 iso-alkanes (also called isoparaffins), isododecane, isodecane, isohexadecane, and, for example, oils sold under the trade names Isopars or Permetyls,
  • n-dodecane C 12
  • CM n-tetradecane
  • PARAFOL 12-97 and PARAFOL 14-97 the mixture undecane-tridecane
  • Si 3 the mixtures of n-undecane
  • the volatile oil content is between 1 % and 15% by weight, with respect to the total weight of the composition, preferably between 2% and 8% by weight, with respect to the total weight of the composition.
  • the composition according to the invention is free of volatile oil.
  • compositions according to the invention can also include at least one dye.
  • a composition according to this invention can include at least one dye chosen from the water-soluble or non-water-soluble, liposoluble or non-liposoluble, organic or inorganic dyes, in particular such as pigments or nacres conventionally used in cosmetic compositions, materials with an optical effect, and mixtures thereof.
  • the dyes can be present in an amount of 0.1 % to 20% by weight, preferably 1 % to 1 5% by weight with respect to the total weight of the composition used according to the invention.
  • Pigments should be understood as meaning white or colored inorganic (mineral) or organic particles, insoluble in an aqueous solution, intended to color the resulting deposit.
  • mineral pigments that can be used in the invention, mention may be made of titanium, zirconium or cerium oxides, as well as zinc, iron or chromium oxides, ferric blue, manganese violet, ultramarine blue and chromium hydrate.
  • the pigment might also be a pigment having a structure that may be, for example, of the sericite/brown iron oxide/titanium dioxide/silica type.
  • a pigment is sold, for example, under the name "COVERLEAF NS” or "JS” by the CHEMICALS AND CATALYSTS company and has a contrast ratio of around 30.
  • the dye may also comprise a pigment having a structure that can be, for example, of the silica microsphere type containing iron oxide.
  • a pigment having this structure is that sold by the MIYOSH I company under the name "PC BALL PC-LL-100 P", this pigment consisting of silica microspheres containing yellow iron oxide.
  • PC BALL PC-LL-100 P this pigment consisting of silica microspheres containing yellow iron oxide.
  • calcium and sodium borosilicate in the form of a calcium and sodium borosilicate plate coated with titanium and tin dioxide (94.25/5.25/0.5).
  • DPP diketopyrrolopyrroles
  • Nacres should be understood as meaning iridescent or non-iridescent colored particles of any shape, in particular produced by certain mollusks in their shell or synthesized, and which have an effect on color due to optical interference.
  • Nacres can be chosen from pearlescent pigments such as titanium mica coated with iron oxide, titanium mica coated with bismuth oxychloride, titanium mica coated with chromium oxide, titanium mica coated with an organic dye as well as pearlescent pigments based on bismuth oxychloride. They may also be mica particles at the surface of which at least two successive layers of metal oxides and/or organic dyes are superimposed.
  • TIMICA "FLAMENCO” and “DUOCHROME” nacres (mica-based) sold by the ENGELHARD company
  • TIMIRON nacres sold by the MERCK company
  • mica-based nacres mica-based nacres
  • PRESTIGE mica-based nacres
  • SUNSHINE synthetic mica-based nacres
  • the nacres may more specifically have a yellow, pink, red, bronze, orange, brown and/or copper color or glint.
  • nacres that can be used in the context of this invention, mention may be made in particular of the gold-colored nacres in particular sold by the ENGELHARD company under the name Brilliant gold 212G (Timica), Gold 222C (Cloisonne), Sparkle gold (Timica), Gold 4504 (Chromalite) and Monarch gold 233X (Cloisonne); the bronzes nacres in particular sold by the MERCK company under the name Bronze fine (17384) (Colorona) and Bronze (17353) (Colorona) and by the ENGELHARD company under the name Super bronze (Cloisonne); the orange nacres in particular sold by the ENGELHARD company under the name Orange 363C (Cloisonne) and Orange MCR 101 (Cosmica) and by the MERCK company under the name Passion orange (Colorona) and Matte orange (17449) (Microna); the brown-hued nacres in particular sold by the ENGELHARD company under the name Nu-
  • a cosmetic composition used according to the invention may also contain at least one material with a specific optical effect.
  • this material can be chosen from particles with a metallic glint, goniochromatic coloring agents, diffracting pigments, thermochromatic agents, optical brighteners, and also fibers, in particular of the interference type.
  • the metallic-glint particles that can be used in the invention are in particular chosen from:
  • - particles comprising a single-substance or multi-substance, organic or mineral substrate, at least partially coated with at least one metallic glint layer comprising at least one metal and/or at least one metal derivative, and
  • metals that may be present in said particles, mention may, for example, be made of Ag, Au, Cu, Al, Ni, Sn, Mg, Cr, Mo, Ti, Zr, Pt, Va, Rb, W, Zn, Ge, Te, Se and mixtures or alloys thereof.
  • Ag, Au, Cu, Al, Zn, Ni, Mo, Cr, and mixtures or alloys thereof (for example bronzes and brasses) are preferred metals.
  • metal derivatives refers to compounds derived from metals, in particular oxides, fluorides, chlorides and sulfides. By way of illustration of these particles, mention may be made of aluminum particles, such as those sold under the names “STARBRITE 1200 EAC ® " by the SIBERLINE company and “METALURE ® “ by the ECKART company.
  • metal powders of copper or of alloy mixtures such as those under reference 2844 sold by the RADIUM BRONZE company, metal pigments such as aluminum or bronze, for instance those sold under the names "ROTOSAFE 700" of the ECKART company, silica-coated aluminum particles sold under the name “VISIONAIRE BRIGHT SILVER” of the ECKART company and metal alloy particles such as silica-coated bronze (copper and zinc alloy) sold under the name "VISIONAIRE BRIGHT NATURAL GOLD" of the ECKART company.
  • the particles may also be particles comprising a glass substrate, such as those sold by the NIPPON SHEET GLASS company under the name "MICROGLASS METASHINE".
  • the goniochromatic coloring agent may be selected, for example, from multilayer interference structures and liquid-crystal coloring agents.
  • Examples of symmetrical multilayer interference structures that may be used in compositions prepared in accordance with the invention are, for example, the following structures: Al/Si0 2 /Al/Si0 2 /Al, pigments having this structure being sold by the DUPONT DE NEMOURS company; Cr/MgF 2 /AI/MgF 2 /Cr, pigments having this structure being sold under the name "CHROMAFLAIR" by the FLEX company; MoS 2 /Si0 2 /AI/Si0 2 /MoS 2 ; Fe 2 0 3 /Si0 2 /Al/Si0 2 /Fe 2 0 3 , and
  • these pigments may be pigments with a silica/titanium oxide/tin oxide structure sold under the name "XIRONA MAGIC" by the MERCK company, pigments with a silica/brown iron oxide structure sold under the name “XIRONA INDIAN SUMMER” by the MERCK company and pigments with a silica/titanium oxide/mica/tin oxide structure sold under the name "XIRONA CARRIBEAN BLUE” by the MERCK company. Mention may also be made of the "INFINITE COLORS” pigments of the SHISEIDO company. Depending on the thickness and the nature of the different layers, different effects are obtained.
  • the color changes from green-gold to red-gray for Si0 2 layers from 320 to 350 nm; from red to golden for Si0 2 layers from 380 to 400 nm; from violet to green for Si0 2 layers from 410 to 420 nm; from copper to red for Si0 2 layers from 430 to 440 nm.
  • Pigments with a polymeric multilayer structure Mention may be made, by way of example of pigments with a polymeric multilayer structure, of those sold by the 3M company under the name "COLOR GLITTER”.
  • liquid-crystal goniochromatic particles examples include those sold by the CHENIX company as well as those sold under the name "HELICONE ® HC" by the WACKER company.
  • the liposoluble coloring agents are, for example, Sudan red, DC Red 17, DC Green 6, ⁇ -carotene, soybean oil, Sudan brown, DC Yellow 1 1 , DC Violet 2, DC orange 5, and quinoline yellow.
  • a cosmetic composition used according to the invention may also comprise at least one filler of organic or mineral origin.
  • Filler should be understood as meaning colorless or white solid particles of any shape, which are in an insoluble form and dispersed in the medium of the composition. Mineral or organic in nature, they make it possible to confer body or rigidity on the composition, and/or softness, and uniformity on the makeup. They are distinct from the dyes.
  • fillers that may be used in the compositions according to the invention, mention may be made of silica, kaolin, bentone, starch, lauroyl-lysine, pyrogenic silica particles, optionally hydrophilic or hydrophobic, and mixtures thereof.
  • a composition used according to the invention may include one or more fillers in a content ranging from 0.1 % to 15% by weight with respect to the total weight of the composition, in particular 1 % to 10% by weight with respect to the total weight of the composition.
  • a composition used according to the invention may also include any cosmetic ingredient normally used that may be chosen in particular from active cosmetic agents, antioxidants, fragrances, preservatives, neutralizing agents, surfactants, sunscreens, sweetening agents, vitamins, moisturizers, softeners, hydrophilic or lipophilic active agents, anti-free radical agents, sequestering agents, film-forming polymers and mixtures thereof.
  • a composition according to the invention may more specifically be a makeup and/or skin and/or lip care composition, in particular a lip care composition, and more specifically a lipstick.
  • a composition according to the invention may constitute a blush, an eye shadow, a foundation, an under-eye concealer, a lipstick, a liquid lipstick such as a gloss, for example, a body makeup product, a facial or body care product or a sunscreen product.
  • a composition of the invention is in solid form.
  • solid formulations mention may in particular be made of solid lipsticks, for example.
  • composition according to the invention may be produced by known methods, generally used in the cosmetic or dermatological field.
  • composition according to the invention makes it possible to provide a deposit having good cosmetic properties, in particular in terms of stability (and in particular stability of the brightness of the deposit on the skin or lips), and brightness and stability over time.
  • the brightness and stability may in particular be evaluated in vivo by means of a Chromasphere SEI-M-02232-CHRO-0 as described in the application FR 2 829 344.
  • the stability over time of a cosmetic composition results from its ability to withstand mechanical or physical stresses, such as friction or stretching of the surface to which the makeup is applied.
  • a composition according to the invention preferably has a color stability, measured according to the protocol described above, of greater than or equal to 50, and preferably greater than or equal to 60.
  • This invention also relates to a non-therapeutic method of cosmetic treatment of the skin and/or lips including a step of applying at least one layer of a composition according to the invention to the skin and/or lips.
  • This invention also relates to a non-therapeutic method of cosmetic makeup and/or skin and/or lip care, in particular lip care, including a step of applying at least one layer of a cosmetic composition according to the invention on the skin and/or lips.
  • compositions are prepared according to the usual methods for producing cosmetic compositions.
  • ethylcellulose is added to octyldodecanol, trimethyl pentaphenyl trisiloxane, phenyl trimethicone, dextrin ester (isostearate for the composition of example 1 , and dextrin palmitate for the composition of example 2) and it is all homogenized by means of a Rayneri at 100°C to obtain a homogeneous transparent mixture.
  • the product resulting from the grinding of waxes present in the medium is then added.
  • the nacres and pigments are added to it.
  • the mixture thus obtained once homogenized, is poured into a mold, cooled and removed from the mold.
  • composition 1 according to the invention, the mold removal is performed appropriately while the comparative composition of example 1 a is too soft for this to be possible.
  • a hardness of 79-80 Nm " is obtained (measured according to the protocol indicated in the description).
  • composition according to the invention is applied with a satisfactory slip, in a homogeneous, non-tacky and bright deposit.
  • the degree of transfer onto a cup is also very low (protocol used: 1 .
  • the lipstick is applied; 2. Wait 20 minutes ; 3. A cup is brought to the lips and the amount transferred is observed).
  • the comparative composition also produces a tacky deposit, with a significant degree of transfer (cup).
  • composition and the lipstick are prepared according to the method described in the previous example.
  • the brightness and stability are evaluated in vivo by means of a Chromasphere SEI-M-02232-CHRO-0 as described in the application FR 2 829 344.
  • composition according to the invention is therefore bright with a very good brightness stability.

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Abstract

La présente invention concerne une composition cosmétique anhydre comprenant, dans un milieu physiologiquement acceptable : •- de l'alkylcellulose, de préférence de l'éthylcellulose; • au moins un ester de dextrine ramifiée, de préférence de l'isostéarate de la dextrine; et • au moins un alcool gras ROH, R représentant un radical hydrocarboné saturé ou insaturé, linéaire ou ramifié, comprenant au moins 8 atomes de carbone, de préférence l'octyldodécanol.
PCT/EP2014/066171 2013-07-31 2014-07-28 Composition cosmétique anhydre comprenant de l'alkylcellulose, au moins un ester de dextrine ramifié et au moins un alcool gras WO2015014789A1 (fr)

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JP2016190810A (ja) * 2015-03-31 2016-11-10 株式会社コーセー 油性口唇化粧料
FR3045365A1 (fr) * 2015-12-21 2017-06-23 Oreal Composition comprenant d'alkylcellulose, des huiles hydrocarbonees et siliconees incompatibles et procede la mettant en oeuvre
FR3045364A1 (fr) * 2015-12-21 2017-06-23 Oreal Composition comprenant de l'alkylcellulose, des huiles hydrocarbonees et siliconees incompatibles, une cire et procede la mettant en oeuvre
WO2017108584A1 (fr) * 2015-12-21 2017-06-29 L'oreal Composition contenant de l'alkylcellulose, des huiles siliconées et hydrocarbonées incompatibles, et procédé l'utilisant
WO2018092175A1 (fr) * 2016-11-17 2018-05-24 株式会社 資生堂 Composition huileuse et cosmétique huileux
WO2020068261A1 (fr) 2018-09-28 2020-04-02 Massachusetts Institute Of Technology Molécules immunomodulatrices localisées dans le collagène et leurs procédés
WO2021123667A1 (fr) * 2019-12-20 2021-06-24 L V M H Recherche Composition cosmétique aux propriétés de brillance et de tenue
WO2021123669A1 (fr) * 2019-12-20 2021-06-24 L V M H Recherche Composition cosmétique liquide aux propriétés de brillance et de tenue
WO2021198258A1 (fr) 2020-03-31 2021-10-07 BioNTech SE Traitement impliquant un arn non immunogène pour la vaccination d'antigènes
WO2021209621A1 (fr) * 2020-04-17 2021-10-21 Total Marketing Services Monomères, oligomères et polymères de sucres fonctionnalisés avec des acides gras linéaires ou ramifiés et leurs dérivés, leurs compositions et leurs utilisations
WO2022218891A2 (fr) 2021-04-12 2022-10-20 BioNTech SE Compositions d'arn comprenant une substance tampon et procédés de préparation, de stockage et d'utilisation de celles-ci
WO2023083916A1 (fr) 2021-11-09 2023-05-19 BioNTech SE Arn codant pour la peptidoglycane hydrolase et son utilisation pour le traitement d'une infection bactérienne
WO2023126053A1 (fr) 2021-12-28 2023-07-06 BioNTech SE Formulations à base de lipides pour administration d'arn
WO2024027910A1 (fr) 2022-08-03 2024-02-08 BioNTech SE Arn pour la prévention ou le traitement de la tuberculose

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JP2016190810A (ja) * 2015-03-31 2016-11-10 株式会社コーセー 油性口唇化粧料
US11351105B2 (en) * 2015-12-21 2022-06-07 L'oreal Composition comprising alkylcellulose, incompatible hydrocarbon and silicone oils and method employing it
FR3045364A1 (fr) * 2015-12-21 2017-06-23 Oreal Composition comprenant de l'alkylcellulose, des huiles hydrocarbonees et siliconees incompatibles, une cire et procede la mettant en oeuvre
WO2017108584A1 (fr) * 2015-12-21 2017-06-29 L'oreal Composition contenant de l'alkylcellulose, des huiles siliconées et hydrocarbonées incompatibles, et procédé l'utilisant
KR20180086256A (ko) * 2015-12-21 2018-07-30 로레알 알킬셀룰로오스, 불상용성 탄화수소 및 실리콘 오일을 포함하는 조성물 및 이의 이용 방법
JP2018537489A (ja) * 2015-12-21 2018-12-20 ロレアル アルキルセルロースと、非相溶性である炭化水素およびシリコーン油とを含む組成物ならびにそれを用いる方法
US20190015314A1 (en) * 2015-12-21 2019-01-17 L'oreal Composition comprising alkylcellulose, incompatible hydrocarbon and silicone oils and method employing it
JP2020033383A (ja) * 2015-12-21 2020-03-05 ロレアル アルキルセルロースと、非相溶性である炭化水素およびシリコーン油とを含む組成物ならびにそれを用いる方法
FR3045365A1 (fr) * 2015-12-21 2017-06-23 Oreal Composition comprenant d'alkylcellulose, des huiles hydrocarbonees et siliconees incompatibles et procede la mettant en oeuvre
KR102108114B1 (ko) * 2015-12-21 2020-05-11 로레알 알킬셀룰로오스, 불상용성 탄화수소 및 실리콘 오일을 포함하는 조성물 및 이의 이용 방법
WO2018092175A1 (fr) * 2016-11-17 2018-05-24 株式会社 資生堂 Composition huileuse et cosmétique huileux
JPWO2018092175A1 (ja) * 2016-11-17 2019-10-10 株式会社 資生堂 油性組成物および油性化粧料
WO2020068261A1 (fr) 2018-09-28 2020-04-02 Massachusetts Institute Of Technology Molécules immunomodulatrices localisées dans le collagène et leurs procédés
FR3104991A1 (fr) * 2019-12-20 2021-06-25 L V M H Recherche Composition cosmétique aux propriétés de brillance et de tenue
FR3104986A1 (fr) * 2019-12-20 2021-06-25 L V M H Recherche Composition cosmétique liquide aux propriétés de brillance et de tenue
WO2021123669A1 (fr) * 2019-12-20 2021-06-24 L V M H Recherche Composition cosmétique liquide aux propriétés de brillance et de tenue
WO2021123667A1 (fr) * 2019-12-20 2021-06-24 L V M H Recherche Composition cosmétique aux propriétés de brillance et de tenue
CN114867459A (zh) * 2019-12-20 2022-08-05 Lvmh研究公司 具有光泽和持久特性的化妆品组合物
WO2021198258A1 (fr) 2020-03-31 2021-10-07 BioNTech SE Traitement impliquant un arn non immunogène pour la vaccination d'antigènes
WO2021209621A1 (fr) * 2020-04-17 2021-10-21 Total Marketing Services Monomères, oligomères et polymères de sucres fonctionnalisés avec des acides gras linéaires ou ramifiés et leurs dérivés, leurs compositions et leurs utilisations
WO2022218891A2 (fr) 2021-04-12 2022-10-20 BioNTech SE Compositions d'arn comprenant une substance tampon et procédés de préparation, de stockage et d'utilisation de celles-ci
WO2023083916A1 (fr) 2021-11-09 2023-05-19 BioNTech SE Arn codant pour la peptidoglycane hydrolase et son utilisation pour le traitement d'une infection bactérienne
WO2023126053A1 (fr) 2021-12-28 2023-07-06 BioNTech SE Formulations à base de lipides pour administration d'arn
WO2023126404A1 (fr) 2021-12-28 2023-07-06 BioNTech SE Formulations à base de lipides pour l'administration d'arn
WO2024027910A1 (fr) 2022-08-03 2024-02-08 BioNTech SE Arn pour la prévention ou le traitement de la tuberculose

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