WO2007054492A1 - Composition cosmétique comprenant un polymère de type silicone servant à structurer une phase grasse, caractérisée par une dureté - Google Patents

Composition cosmétique comprenant un polymère de type silicone servant à structurer une phase grasse, caractérisée par une dureté Download PDF

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Publication number
WO2007054492A1
WO2007054492A1 PCT/EP2006/068176 EP2006068176W WO2007054492A1 WO 2007054492 A1 WO2007054492 A1 WO 2007054492A1 EP 2006068176 W EP2006068176 W EP 2006068176W WO 2007054492 A1 WO2007054492 A1 WO 2007054492A1
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groups
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composition according
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chosen
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PCT/EP2006/068176
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Inventor
Xavier Blin
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L'oréal
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Priority claimed from FR0553394A external-priority patent/FR2892929B1/fr
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Publication of WO2007054492A1 publication Critical patent/WO2007054492A1/fr

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    • 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
    • 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
    • A61K8/89—Polysiloxanes
    • A61K8/891—Polysiloxanes saturated, e.g. dimethicone, phenyl trimethicone, C24-C28 methicone or stearyl dimethicone
    • A61K8/893—Polysiloxanes saturated, e.g. dimethicone, phenyl trimethicone, C24-C28 methicone or stearyl dimethicone modified by an alkoxy or aryloxy group, e.g. behenoxy dimethicone or stearoxy dimethicone
    • 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
    • A61K8/89—Polysiloxanes
    • A61K8/896—Polysiloxanes containing atoms other than silicon, carbon, oxygen and hydrogen, e.g. dimethicone copolyol phosphate
    • A61K8/898—Polysiloxanes containing atoms other than silicon, carbon, oxygen and hydrogen, e.g. dimethicone copolyol phosphate containing nitrogen, e.g. amodimethicone, trimethyl silyl amodimethicone or dimethicone propyl PG-betaine

Definitions

  • Cosmetic composition comprising a silicone polymer for structuring a fatty phase, characterized by a hardness
  • the present invention relates to a cosmetic composition for making up or caring for keratin materials, in particular the skin, the lips and keratin fibres, such as the eyelashes, the eyebrows or the hair, and preferably a makeup composition.
  • It may be a loose or compacted powder, a foundation, a makeup rouge, an eyeshadow, a concealer product, a blusher, a lipstick, a lip balm, a lip gloss, a lip or eye pencil, a mascara, an eyeliner, a body makeup product or a skin colouring product .
  • WO-A-02/17871 EP-A-I 177 784, WO-A- 99/06473 and US-A-6 353 076, which is a division of US-A-6 051 216, propose cosmetic compositions such as deodorant sticks or gels, comprising a silicone oily phase gelled with a polysiloxane/polyamide polymer.
  • the present invention more particularly results from the observation by the inventors that a composition comprising a fatty phase structured with a particular silicone polymer and obtained by means of a specific process allows access to a cosmetic composition of novel texture, namely a soft, fluid paste that shows good elasticity.
  • This texture allows the deposition of a smooth, uniform film on keratin fibres, which shows good staying power and/or sheen properties.
  • the fatty phase of the composition is subjected to a shear, which is preferably continuous, advantageously at a temperature greater than or equal to the temperature of transition from the solid state to the liquid state of the silicone polymer. This results in a particular organization of the fatty phase in the composition, which is characterized by this soft and elastic texture.
  • solid-liquid transition temperature the temperature of transition from the solid state to the liquid state.
  • composition obtained via such a process is distinguished by a particular change in its hardness when it is subjected to a new thermal cycle comprising a step of heating from a temperature of 2O 0 C to a temperature of HO 0 C followed by a step of cooling from HO 0 C to 2O 0 C.
  • composition obtained via the process according to the invention is again heated to a solid-liquid transition temperature greater than that of the silicone polymer according to a conventional process, and then cooled, the particular organization of the fatty phase within the composition is destroyed, which is reflected by a significant change in the hardness of the composition (characterized by a final hardness/initial hardness ratio, as defined later, of greater than 2 or by a variation in hardness of at least 10 g) .
  • the present invention relates to a cosmetic composition
  • a cosmetic composition comprising a fatty phase comprising at least one silicone polymer comprising at least one unit comprising: 1) polyorganosiloxanes comprising at least two groups capable of establishing hydrogen interactions, these two groups being located in the polymer chain, and/or
  • polyorganosiloxanes comprising at least two groups capable of establishing hydrogen interactions, these two groups being located on grafts or branches, the said composition being such that, after having been subjected to a temperature of HO 0 C, it shows a variation in hardness, written as ⁇ hardness, corresponding to the difference between the final hardness at 2O 0 C after heating to HO 0 C and the initial hardness at 2O 0 C before heating, of at least 10 g and preferably of at least 20 g.
  • a subject of the present invention is also a cosmetic composition
  • a cosmetic composition comprising a fatty phase comprising at least one silicone polymer comprising at least one unit comprising:
  • polyorganosiloxanes comprising at least two groups capable of establishing hydrogen interactions, these two groups being located in the polymer chain, and/or
  • polyorganosiloxanes comprising at least two groups capable of establishing hydrogen interactions, these two groups being located on grafts or branches, the said composition being such that, after having been subjected to a temperature of HO 0 C, the ratio of the final hardness at 2O 0 C after heating to the initial hardness at 2O 0 C before heating is greater than or equal to 2 and preferably greater than or equal to 3.
  • the hardness is measured according to the following protocol :
  • the samples of composition are prepared by introducing a sufficient amount of the test composition into, for example, a pretared 100 x 15 mm Petri dish, to obtain a sample about 1 cm thick.
  • the hardness of the composition is then measured using a texturometer, which makes it possible to obtain the variation in the resistance to deformation of the composition as a function of the displacement of a mobile into a sample of the said composition.
  • the texturometer measures the force of resistance to deformation of the composition as soon as the mobile comes into contact with the sample. After having reached a programmed maximum depth LO into the sample, the mobile returns to the initial point.
  • the hardness (expressed in grams or in newtons) is equal to the resistance value of the composition when the mobile is at the end of its course. The breaking of contact is reflected by cancellation of the force of resistance of the composition on the mobile.
  • the texturometer used may especially be a Stable Micro System TAX-T2i * texturometer equipped with operating software such as Texture Expert Exceed ® and fitted with a P/0.5 HS Rheo plastic hemispherical mobile.
  • the applied parameters are advantageously the following : - speed before contact: 0.1 mm.s "1 ,
  • At least three measurements are taken on each sample: one at the centre and others at points equidistant from the centre and from the edge of the dish.
  • the hardness value retained is equal to the mean of the measurements taken, of a minimum number of six.
  • the hardness of the composition is thus measured according to the following protocol at 2O 0 C, then a sample of the same composition is heated to a temperature of HO 0 C with stirring using a Rayneri blender for 45 minutes, and the mixture is then poured into a Petri dish, filling it to the brim. Once the mixture has set to a solid, the dish is stored at 2O 0 C for 24 hours and the measurement of the hardness of this composition is then performed as indicated above.
  • the ratio between the final hardness after heating to the initial hardness of greater than 2 is characteristic of the process for preparing the composition, which comprises at least one step of controlled and preferably continuous shear, of all or part of the fatty phase structured with the silicone compound, advantageously at a temperature greater than or equal to the solid-liquid transition temperature of the silicone polymer.
  • composition according to the invention comprises a cosmetically acceptable medium, i.e. a non-toxic medium that may be applied to human keratin materials and that is of pleasant appearance, odour and feel .
  • the present invention is also directed towards a process for caring for or making up keratin materials, characterized in that a composition in accordance with the invention is applied to the said fibres.
  • the soft and elastic textures obtained according to the invention are compatible with direct application to the lips by finger or using an applicator, for instance a foam tip.
  • the silicone polymers of the composition are preferably solid at room temperature (25 0 C) and atmospheric pressure (760 mmHg) .
  • polymer means a compound containing at least 2 repeating units, preferably at least 3 repeating units and better still 10 repeating units.
  • the silicone polymers used as structuring agents in the composition of the invention are polymers of the polyorganosiloxane type, for instance those described in documents US-A-5 874 069, US-A-5 919 441, US-A-6 051 216 and US-A-5 981 680.
  • the polymers used as structuring agent may belong to the following two families:
  • polyorganosiloxanes comprising at least two groups capable of establishing hydrogen interactions, these two groups being located in the polymer chain, and/or 2) polyorganosiloxanes comprising at least two groups capable of establishing hydrogen interactions, these two groups being located on grafts or branches.
  • the groups capable of establishing hydrogen interactions may be chosen from ester, amide, sulfonamide, carbamate, thiocarbamate, urea, urethane, thiourea, oxamido, guanidino and biguanidino groups, and combinations thereof.
  • the silicone polymers are polyorganosiloxanes as defined above in which the units capable of establishing hydrogen interactions are located in the polymer chain.
  • the silicone polymers may be more particularly polymers comprising at least one unit corresponding to the general formula I :
  • R 4 , R 5 , R 6 and R 7 which may be identical or different, represent a group chosen from: linear, branched or cyclic, saturated or unsaturated, Ci to C 40 hydrocarbon-based groups, possibly containing in their chain one or more oxygen, sulfur and/or nitrogen atoms, and possibly being partially or totally substituted with fluorine atoms,
  • Cio aryl groups optionally substituted with one or more Ci to C 4 alkyl groups, polyorganosiloxane chains possibly containing one or more oxygen, sulfur and/or nitrogen atoms,-
  • the groups X which may be identical or different, represent a linear or branched Ci to C 30 alkylenediyl group, possibly containing in its chain one or more oxygen and/or nitrogen atoms,-
  • Y is a saturated or unsaturated, Ci to C 50 linear or branched divalent alkylene, arylene, cycloalkylene, alkylarylene or arylalkylene group, possibly comprising one or more oxygen, sulfur and/or nitrogen atoms, and/or bearing as substituent one of the following atoms or groups of atoms: fluorine, hydroxyl , C 3 to C 8 cycloalkyl, Ci to C 40 alkyl, C 5 to Ci 0 aryl, phenyl optionally substituted with 1 to 3 Ci to C 3 alkyl , Ci to C 3 hydroxyalkyl and Ci to C 6 aminoalkyl groups ; or
  • Y represents a group corresponding to the formula:
  • T represents a linear or branched, saturated or unsaturated, C 3 to C 24 trivalent or tetravalent hydrocarbon-based group optionally substituted with a polyorganosiloxane chain, and possibly containing one or more atoms chosen from 0, N and S, or T represents a trivalent atom chosen from N, P and Al, and
  • R 8 represents a linear or branched Ci to C 50 alkyl group or a polyorganosiloxane chain, possibly comprising one or more ester, amide, urethane, thiocarbamate, urea, thiourea and/or sulfonamide groups, which may possibly be linked to another chain of the polymer; 5) the groups G, which may be identical or different, represent divalent groups chosen from:
  • R 9 represents a hydrogen atom or a linear or branched Ci to C 2 o alkyl group, on condition that at least 50% of the groups R 9 of the polymer represent a hydrogen atom and that at least two of the groups G of the polymer are a group other than:
  • n is an integer ranging from 2 to 500 and preferably from 2 to 200
  • m is an integer ranging from 1 to 1000, preferably from 1 to 700 and better still from 6 to 200.
  • 80% of the groups R 4 , R 5 , R 6 and R 7 of the polymer are preferably chosen from methyl, ethyl, phenyl and 3 , 3 , 3-trifluoropropyl groups.
  • Y can represent various divalent groups, furthermore optionally comprising one or two free valencies to establish bonds with other units of the polymer or copolymer.
  • Y represents a group chosen from: a) linear Ci to C 20 and preferably Ci to Ci 0 alkylene groups, b) C 30 to C 56 branched alkylene groups possibly comprising rings and unconjugated unsaturations, c) C 5 -C 6 cycloalkylene groups, d) phenylene groups optionally substituted with one or more Ci to C 40 alkyl groups, e) Ci to C 20 alkylene groups comprising from 1 to 5 amide groups, f) Ci to C 20 alkylene groups comprising one or more substituents chosen from hydroxyl , C 3 to C 8 cycloalkane, Ci to C 3 hydroxyalkyl and Ci to C 6 alkylamine groups, g) polyorganosiloxane chains of formula:
  • the polyorganosiloxanes may be polymers comprising at least one unit corresponding to formula (II) : (!) in which
  • R 4 and R 6 which may be identical or different, are as defined above for formula (I) ,
  • R 10 represents a group as defined above for R 4 and R 6 , or represents a group of formula -X-G-R 12 in which X and G are as defined above for formula (I) and R 12 represents a hydrogen atom or a linear, branched or cyclic, saturated or unsaturated, Ci to C 50 hydrocarbon- based group optionally comprising in its chain one or more atoms chosen from 0, S and N, optionally substituted with one or more fluorine atoms and/or one or more hydroxyl groups, or a phenyl group optionally substituted with one or more Ci to C 4 alkyl groups,
  • R 1 represents a group of formula -X-G-R in which X, G and R 12 are as defined above, mi is an integer ranging from 1 to 998, and m 2 is an integer ranging from 2 to 500.
  • the polymer used as structuring agent may be a homopolymer, that is to say a polymer comprising several identical units, in particular units of formula (I) or of formula (II) .
  • a polymer consisting of a copolymer comprising several different units of formula (I) that is to say a polymer in which at least one of the groups R 4 , R 5 , R 6 , R 7 , X, G, Y, m and n is different in one of the units.
  • the copolymer may also be formed from several units of formula (II) , in which at least one of the groups R 4 , R 6 , R 10 , R 11 , mi and m 2 is different in at least one of the units.
  • a polymer comprising at least one unit of formula (I) and at least one unit of formula (II) the units of formula (I) and the units of formula (II) possibly being identical to or different from each other.
  • a polymer furthermore comprising at least one hydrocarbon-based unit comprising two groups capable of establishing hydrogen interactions, chosen from ester, amide, sulfonamide, carbamate, thiocarbamate, urea, urethane, thiourea, oxamido, guanidino and biguanidino groups, and combinations thereof.
  • copolymers may be block polymers or grafted polymers .
  • the groups capable of establishing hydrogen interactions are amide groups of formulae -C(O)NH- and -HN-C(O) - .
  • the structuring agent may be a polymer comprising at least one unit of formula (III) or (IV) :
  • Such a unit may be obtained: either by a condensation reaction between a silicone containing ⁇ , ⁇ -carboxylic acid ends and one or more diamines, according to the following reaction scheme :
  • m is in the range from 1 to 700, in particular from 15 to 500 and especially from 50 to 200, and n is in particular in the range from 1 to 500, preferably from 1 to 100 and better still from 4 to 25,
  • - X is preferably a linear or branched alkylene chain containing from 1 to 30 carbon atoms, in particular 1 to 20 carbon atoms, especially from 5 to 15 carbon atoms and more particularly 10 carbon atoms, and
  • - Y is preferably an alkylene chain that is linear or branched or that possibly comprises rings and/or unsaturations, containing from 1 to 40 carbon atoms, in particular from 1 to 20 carbon atoms and better still from 2 to 6 carbon atoms, in particular 6 carbon atoms.
  • the alkylene group representing X or Y can optionally contain in its alkylene portion at least one of the following members:
  • alkylene groups may also be substituted with at least one member chosen from the group consisting of:
  • Y may also represent:
  • R 8 represents a polyorganosiloxane chain
  • a, b and c are, independently, integers ranging from 1 to 10
  • R 13 is a hydrogen atom or a group such as those defined for R 4 , R 5 , R 6 and R 7 .
  • R 4 , R 5 , R 6 and R 7 preferably represent, independently, a linear or branched Ci to C 4 o alkyl group, preferably a CH 3 , C 2 H 5 , n-C 3 H 7 or isopropyl group, a polyorganosiloxane chain or a phenyl group optionally substituted with one to three methyl or ethyl groups .
  • the polymer may comprise identical or different units of formula (III) or (IV) .
  • the polymer may be a polyamide containing several units of formula (III) or (IV) of different lengths, i.e. a polyamide corresponding to formula (V) : - [Fc(O)-X JH-SiO-J- *Si- - X --- C(O) — NH — Y— NH Lj L — C(O)X T 1 SiYOj-S'i 5 X C(O)- NH — Y— NH 1H
  • the units may be structured to form either a block copolymer, or a random copolymer or an alternating copolymer.
  • the units may be not only of different lengths, but also of different chemical structures, for example containing different groups Y.
  • the polymer may correspond to formula VI :
  • R 4 to R 7 , X, Y, mi, m 2 , n and p have the meanings given above and Y 1 is different from Y but chosen from the groups defined for Y.
  • the various units may be structured to form either a block copolymer, or a random copolymer or an alternating copolymer.
  • the structuring agent may also consist of a grafted copolymer.
  • the polyamide containing silicone units may be grafted and optionally crosslinked with silicone chains containing amide groups.
  • Such polymers may be synthesized with trifunctional amines.
  • the polymer may comprise at least one unit of formula (VII) :
  • - p is in the range from 1 to 25 and better still from 1 to 7 ,
  • R 14 to R 21 are methyl groups
  • R 22 is a hydrogen atom or a group chosen from the groups defined for R 4 to R 7
  • R 23 , R 24 and R 25 are, independently, linear or branched alkylene groups, and more preferably correspond to the formula: in particular with R 23 , R 24 and R 25 representing -CH 2 -CH 2 -,
  • - Hi 1 and m 2 are in the range from 15 to 500 and better still from 15 to 45,
  • - X 1 and X 2 represent - (CH 2 ) 10 -
  • - Y represents -CH 2 - .
  • polyamides containing a grafted silicone unit of formula (VII) may be copolymerized with polyamide- silicones of formula (II) to form block copolymers, alternating copolymers or random copolymers.
  • the weight percentage of grafted silicone units (VII) in the copolymer may range from 0.5% to 30% by weight.
  • the siloxane units may be in the main chain or backbone of the polymer, but they may also be present in grafted or pendent chains .
  • the siloxane units may be in the form of segments as described above.
  • the siloxane units may appear individually or in segments.
  • a copolymer of silicone polyamide and of hydrocarbon- based polyamide or a copolymer comprising units of formula (III) or (IV) and hydrocarbon-based polyamide units, may be used.
  • the polyamide- silicone units may be located at the ends of the hydrocarbon-based polyamide.
  • the composition comprises at least one polydimethylsiloxane block polymer of general formula (I) with an index m value of about 100.
  • the composition according to the invention comprises at least one polymer comprising at least one unit of formula (III) in which m ranges from 50 to 600, in particular from 60 to 400, especially from 75 to 200 and is more particularly about 100, and, preferably also, R 4 , R 5 , R 6 and R 7 independently represent, in formula (III) , a linear or branched Ci-C 40 alkyl group, preferably a CH 3 , C 2 H 5 , n- C 3 H 7 or isopropyl group.
  • X and Y independently represent a group chosen from linear Ci-C 2 O and preferably Ci-Ci 0 alkyl groups .
  • the polymer consists of a homopolymer or copolymer comprising urethane or urea groups.
  • urethane or urea groups are described in detail in patent application WO 2003/106 614 published on 24/12/2003, the content of which is incorporated into the present patent application by reference.
  • such a polymer may comprise polyorganosiloxane units containing two or more urethane and/or urea groups, either in the backbone of the polymer or on side chains or as pendent groups.
  • the polymers comprising at least two urethane and/or urea groups in the backbone may be polymers comprising at least one unit corresponding to the following formula (VIII) :
  • Y may be a linear or branched Ci to C 40 alkylene group, optionally substituted with a Ci to Ci 5 alkyl group or a C 5 to Ci 0 aryl group.
  • a -(CH 2 ) 6- group is used.
  • Y may also represent a C 5 to Ci 2 cycloaliphatic or aromatic group that may be substituted with a Ci to Ci 5 alkyl group or a C 5 to Ci 0 aryl group, for example a radical chosen from the methylene-4 , 4-biscyclohexyl radical, the radical derived from isophorone diisocyanate, 2,4- and 2 , 6-tolylenes, 1 , 5-naphthylene, p-phenylene and 4 , 4 ' -biphenylenemethane .
  • Y it is preferred for Y to represent a linear or branched Ci to C 40 alkylene radical or a C 4 to Ci 2 cycloalkylene radical .
  • Y may also represent a polyurethane or polyurea block corresponding to the condensation of several diisocyanate molecules with one or more molecules of coupling agents of the diol or diamine type.
  • Y comprises several urethane or urea groups in the alkylene chain.
  • B 1 is a group chosen from the groups given above for Y, U is -0- or -NH- and B 2 is chosen from:
  • Ci 2 cycloalkylene groups optionally bearing alkyl substituents, for example one to three methyl or ethyl groups, or alkylene, for example the diol radical: cyclohexanedimethanol ,
  • T is a hydrocarbon-based trivalent radical possibly containing one or more heteroatoms such as oxygen, sulfur and nitrogen and R 8 is a polyorgano- siloxane chain or a linear or branched Ci to C 5 o alkyl chain.
  • T can represent, for example: (CH 2 ) W CH CH,.
  • w being an integer ranging from 1 to 10 and R 8 being a polyorganosiloxane chain.
  • Y is a linear or branched Ci to C 40 alkylene group
  • the -(CH 2 ) 2- and - (CH 2 ) 6 - groups are preferred.
  • d may be an integer ranging from 0 to 5 , preferably from 0 to 3 and more preferably equal to 1 or 2.
  • B 2 is a linear or branched Ci to C 40 alkylene group, in particular - (CH 2 ) 2 - or - (CH 2 ) 6 - or a group :
  • R 8 being a polyorganosiloxane chain.
  • the silicone polymer may be formed from silicone urethane and/or silicone urea units of different length and/or constitution, and may be in the form of block or random copolymers .
  • the polymers of formula (VIII) comprising urea or urethane groups in the chain of the silicone polymer may be obtained by reaction between a silicone containing ⁇ , CO-NH 2 or -OH end groups, of formula:
  • Y may have the formula (IX) with d equal to 0 or d equal to 1 to 5.
  • the copolymer may correspond, for example, to the formula:
  • the silicone may also comprise urethane and/or urea groups no longer in the backbone but as side branches.
  • the polymer may comprise at least one unit of formula:
  • - U represents 0 or NH
  • R 26 represents a Ci to C 4 o alkylene group, optionally comprising one or more heteroatoms chosen from 0 and N, or a phenylene group, and
  • R 27 is chosen from linear, branched or cyclic, saturated or unsaturated Ci to C 5 o alkyl groups, and phenyl groups optionally substituted with one to three Ci to C 3 alkyl groups .
  • the polymers comprising at least one unit of formula (X) contain siloxane units and urea or urethane groups, and they may be used as structuring polymer in the compositions of the invention.
  • the siloxane polymers may have a single urea or urethane group by branching or may have branches containing two urea or urethane groups, or alternatively they may contain a mixture of branches containing one urea or urethane group and branches containing two urea or urethane groups .
  • They may be obtained from branched polysiloxanes, comprising one or two amino groups per branch, by reacting these polysiloxanes with monoisocyanates .
  • R represents a linear aliphatic group preferably containing 1 to 6 carbon atoms and better still 1 to 3 carbon atoms.
  • Such polymers containing branching may be formed by reacting a siloxane polymer, containing at least three amino groups per polymer molecule, with a compound containing only one monofunctional group (for example an acid, an isocyanate or an isothiocyanate) to react this monofunctional group with one of the amino groups and to form groups capable of establishing hydrogen interactions.
  • the amino groups may be on side chains extending from the main chain of the siloxane polymer, such that the groups capable of establishing hydrogen interactions are formed on these side chains, or alternatively the amino groups may be at the ends of the main chain, such that the groups capable of hydrogen interaction will be end groups of the polymer.
  • a procedure for forming a polymer containing siloxane units and groups capable of establishing hydrogen interactions mention may be made of the reaction of a siloxane diamine and of a diisocyanate in a silicone solvent so as to provide a gel directly.
  • the reaction may be performed in a silicone fluid, the resulting product being dissolved in the silicone fluid, at high temperature, the temperature of the system then being reduced to form the gel .
  • the polymers that are preferred for incorporation into the compositions according to the present invention are siloxane-urea copolymers that are linear and that contain urea groups as groups capable of establishing hydrogen interactions in the backbone of the polymer.
  • Ph is a phenyl group and n is a number from 0 to 300 and in particular from 0 to 100, for example 50.
  • This polymer is obtained by reacting the following polysiloxane containing amino groups:
  • Branched polyurethane or polyurea silicones may also be obtained by using, instead of the diisocyanate OCN-Y-NCO, a triisocyanate of formula:
  • a polyurethane or polyurea silicone containing branches comprising an organosiloxane chain with groups capable of establishing hydrogen interactions is thus obtained.
  • Such a polymer comprises, for example, a unit corresponding to the formula:
  • copolymers of polyurethane or polyurea silicone and of hydrocarbon- based polyurethane or polyurea may be used in the invention by performing the reaction for synthesizing the polymer in the presence of an ⁇ , ⁇ -difunctional block of non-silicone nature, for example a polyester, a polyether or a polyolefin.
  • the copolymers of the invention may contain siloxane units in the main chain of the polymer and groups capable of establishing hydrogen interactions, either in the main chain of the polymer or at the ends thereof, or on side chains or branches of the main chain. This may correspond to the following five arrangements:
  • the continuous line is the main chain of the siloxane polymer and the squares represent the groups capable of establishing hydrogen interactions.
  • the groups capable of establishing hydrogen interactions are located at the ends of the main chain.
  • two groups capable of establishing hydrogen interactions are located at each of the ends of the main chain.
  • the groups capable of establishing hydrogen interactions are located within the main chain in repeating units.
  • these are copolymers in which the groups capable of establishing hydrogen interactions are located on branches of the main chain of a first series of units that are copolymerized with units not comprising groups capable of establishing hydrogen interactions .
  • the polymers and copolymers used in the composition of the invention advantageously have a transition temperature from the solid state to the liquid state ranging from 45 0 C to 19O 0 C. They preferably have a transition temperature from the solid state to the liquid state ranging from 70 to 13O 0 C and better still from 8O 0 C to 105 0 C.
  • the silicone polymer (s) may be present in the composition according to the invention in a total content ranging from 0.5% to 50% of the total weight of the composition, preferably ranging from 2% to 40% and better still ranging from 5% to 30% by weight relative to the total weight of the composition.
  • compositions in accordance with the present invention comprise a fatty phase advantageously comprising a liquid fatty phase composed of one or more non-aqueous compounds that are liquid at room temperature (25 0 C) or oils.
  • the fatty phase may also comprise one or more nonaqueous compounds that are solid or pasty at room temperature (25 0 C) such as fatty-phase- structuring agents other than the silicone polymer, for instance waxes, pasty fatty substances, semi-crystalline polymers and lipophilic gelling agents, and mixtures thereof .
  • nonaqueous compounds that are solid or pasty at room temperature (25 0 C) such as fatty-phase- structuring agents other than the silicone polymer, for instance waxes, pasty fatty substances, semi-crystalline polymers and lipophilic gelling agents, and mixtures thereof .
  • the liquid fatty phase of the composition comprises at least one volatile silicone oil.
  • the volatile silicone oil may be chosen from linear or cyclic silicone oils with a flash point of greater than or equal to 4O 0 C and advantageously greater than the softening point of the silicone polymer and/or a viscosity of less than 8 cSt, such as linear or cyclic polydimethylsiloxanes (PDMS) containing from 3 to 7 silicon atoms.
  • PDMS linear or cyclic polydimethylsiloxanes
  • the flash point is the temperature at which a fuel catches fire on contact with a flame.
  • oils examples include the compounds cited in Table 1 below.
  • the volatile oil has a flash point of greater than 6O 0 C.
  • the non-volatile silicone oils may be polydimethylsiloxanes , polyalkylmethylsiloxanes , dimethicone copolyols, alkylmethicone copolyols, cetyldimethicone, silicones containing alkyl glyceryl ether groups, silicones containing amine side groups and dilauroyltrimethylolpropane siloxysilicate .
  • the alkyl groups of these oils especially contain from 2 to 24 carbon atoms.
  • the non-volatile silicone oils that may be used in the liquid fatty phase of the invention may in particular be non-volatile linear polydimethylsiloxanes (PDMS) that are liquid at room temperature; polydimethylsiloxanes comprising alkyl, alkoxy or phenyl groups, which are pendent and/or at the end of a silicone chain, these groups each containing from 2 to 24 carbon atoms,- phenylsilicones, for instance phenyl trimethicones, phenyl dimethicones, phenyltrimethyl- siloxydiphenylsiloxanes, diphenyl dimethicones, diphenylmethyldiphenyltrisiloxanes, 2-phenylethyl trimethylsiloxysilicates, fluorosilicones containing one or more group (s) that is (are) pendent or at the end of a chain, containing from 1 to 12 carbon atoms, all or some of the hydrogen atom
  • the composition may comprise at least one volatile silicone oil and at least one volatile non-silicone oil.
  • a silicone or non- silicone volatile oil has a flash point preferably of from 40 to 135 0 C or has no flash point.
  • the volatile oils have at room temperature (25 0 C) and atmospheric pressure (760 mmHg) a vapour pressure ranging from 0.02 mmHg to 300 mmHg (2.66 Pa to 40 000 Pa) and better still ranging from 0.1 to 90 mmHg (13 Pa to 12 000 Pa).
  • the non-volatile oils thus correspond to a vapour pressure of less than 0.02 mmHg (2.66 Pa) .
  • the silicone oils have a viscosity advantageously chosen in the range from 5 to 800 000 cSt, preferably from 10 to 500 000 cSt and better still from 10 to 5000 cSt at 25 0 C.
  • the volatile silicone oil(s) may be chosen, for example, from the group consisting of the compounds of Table 1, heptamethyloctyltrisiloxane and dodecamethylpentasiloxane, and mixtures thereof.
  • the volatile silicone oil may also be chosen from the group of fluorosilicone oils such as silicones containing alkyl and perfluoroalkyl groups, silicones containing oxyethylene/oxypropylene (OE/OP) side groups and perfluoro groups, silicones containing perfluoro side groups and glycerolated side groups, and perfluoroalkylmethylphenylsiloxanes, these oils having a vapour pressure of greater than or equal to 0.02 mmHg.
  • fluorosilicone oils such as silicones containing alkyl and perfluoroalkyl groups, silicones containing oxyethylene/oxypropylene (OE/OP) side groups and perfluoro groups, silicones containing perfluoro side groups and glycerolated side groups, and perfluoroalkylmethylphenylsiloxanes, these oils having a vapour pressure of greater than or equal to 0.02 mmHg.
  • the composition may advantageously comprise at least one silicone oil, which advantageously has a viscosity of less than 1000 cSt and better still less than 100 cSt.
  • the liquid fatty phase advantageously contains at least 5% and for example from 10% to 90% by weight of silicone oil(s).
  • the liquid fatty phase advantageously contains at least one silicone oil that advantageously has a viscosity of less than 1000 cSt and better still less than 100 cSt .
  • composition according to the invention may also contain one or more volatile or non-volatile non- silicone oils.
  • volatile non-silicone oils may be chosen from the group of volatile hydrocarbon-based oils, esters and ethers, such as volatile hydrocarbons, for instance isododecane and isohexadecane, and C 8 -Ci 6 isoparaffins .
  • the volatile non-silicone oil may also be chosen from fluoro oils such as perfluoropolyethers, perfluoroalkanes, for instance perfluorodecalin, perfluoroadamantanes, perfluoroalkyl phosphate monoesters, diesters and triesters, and fluoro ester oils .
  • fluoro oils such as perfluoropolyethers, perfluoroalkanes, for instance perfluorodecalin, perfluoroadamantanes, perfluoroalkyl phosphate monoesters, diesters and triesters, and fluoro ester oils .
  • the fatty phase comprises a volatile oil
  • it advantageously represents from 0.1% to 90% and better still from 0.5% to 60%, for example from 1% to 20%, of the total weight of the composition.
  • composition may also contain other non- silicone oils, for example polar oils such as:
  • oils with a high content of triglycerides consisting of fatty acid esters of glycerol in which the fatty acids may have varied chain lengths, these chains possibly being linear or branched, and saturated or unsaturated; these oils are in particular wheatgerm oil, corn oil, sunflower oil, shea oil, castor oil, sweet almond oil, macadamia oil, apricot oil, soybean oil, rapeseed oil, cottonseed oil, alfalfa oil, poppy seed oil, pumpkin seed oil, sesame seed oil, marrow oil, avocado oil, hazelnut oil, grapeseed oil, blackcurrant seed oil, evening primrose oil, millet oil, barley oil, quinoa oil, olive oil, rye oil, safflower oil, candlenut oil, passion flower oil and musk rose oil; or caprylic/capric acid triglycerides such as those sold by the company Stearines Dubois or those sold under the names Miglyol 810
  • fatty acids for instance oleic acid, linoleic acid or linolenic acid; and - mixtures thereof.
  • the composition may also contain apolar oils such as linear or branched, volatile or non-volatile hydrocarbons or fluorocarbons of synthetic or mineral origin, for instance volatile liquid paraffins (such as isoparaffins or isododecane) or non-volatile liquid paraffins and derivatives thereof, petroleum jelly, polydecenes, hydrogenated polyisobutene such as sesam, and squalane, and mixtures thereof.
  • apolar oils such as linear or branched, volatile or non-volatile hydrocarbons or fluorocarbons of synthetic or mineral origin, for instance volatile liquid paraffins (such as isoparaffins or isododecane) or non-volatile liquid paraffins and derivatives thereof, petroleum jelly, polydecenes, hydrogenated polyisobutene such as sesam, and squalane, and mixtures thereof.
  • composition may optionally comprise at least one oil known as an "ester oil", which is chosen from esters of monocarboxylic acids with monoalcohols and polyalcohols .
  • esters oil which is chosen from esters of monocarboxylic acids with monoalcohols and polyalcohols .
  • the said ester corresponds to the following formula:
  • R 1 -CO-O-R 2 where Ri represents a linear or branched alkyl radical of 1 to 40 carbon atoms and preferably of 7 to 19 carbon atoms, optionally comprising one or more ethylenic double bonds, and optionally substituted,
  • R 2 represents a linear or branched alkyl radical of 1 to 40 carbon atoms, preferably of 3 to 30 carbon atoms and better still of 3 to 20 carbon atoms, optionally comprising one or more ethylenic double bonds, and optionally substituted.
  • Ri and/or R 2 can bear one or more substituents chosen, for example, from groups comprising one or more heteroatoms chosen from 0, N and S, such as amino, amine, alkoxy and hydroxyl .
  • substituents chosen, for example, from groups comprising one or more heteroatoms chosen from 0, N and S, such as amino, amine, alkoxy and hydroxyl .
  • the total number of carbon atoms of Ri + R 2 is > 9.
  • the ester used according to the invention may be referred to as a "short" ester.
  • R 1 may represent the residue of a linear or, preferably, branched fatty acid, preferably a higher fatty acid, containing from 1 to 40 and even better from 7 to 19 carbon atoms
  • R 2 may represent a linear or, preferably, branched hydrocarbon-based chain containing from 1 to 40, preferably from 3 to 30 and even better from 3 to 20 (19 to 28, 8 to 27, 7 to 26 C) carbon atoms.
  • Examples of groups Ri are those derived from fatty acids chosen from the group consisting of acetic acid, propionic acid, butyric acid, caproic acid, caprylic acid, pelargonic acid, capric acid, undecanoic acid, lauric acid, myristic acid, palmitic acid, stearic acid, isostearic acid, arachidic acid, behenic acid, oleic acid, linolenic acid, linoleic acid, oleostearic acid, arachidonic acid and erucic acid, and mixtures thereof.
  • purcellin oil cetostearyl octanoate
  • isononyl isononanoate isopropyl myristate, 2-ethylhexyl palmitate
  • 2-octyldodecyl stearate 2-octyldodecyl erucate
  • the esters are chosen from the compounds of formula (I) above, in which R 1 represents an unsubstituted linear or branched alkyl group of 1 to 40 carbon atoms and preferably of 7 to 19 carbon atoms, optionally comprising one or more ethylenic double bonds, and R 2 represents an unsubstituted linear or branched alkyl group of 1 to 40 carbon atoms, preferably of 3 to 30 carbon atoms and even better of 3 to 20 carbon atoms, optionally comprising one or more ethylenic double bonds .
  • Ri is an unsubstituted branched alkyl group of 4 to 14 carbon atoms and preferably of 8 to 10 carbon atoms
  • R 2 is an unsubstituted branched alkyl group of 5 to 15 carbon atoms and preferably of 9 to 11 carbon atoms.
  • Ri-CO- and R 2 have the same number of carbon atoms and are derived from the same radical, preferably an unsubstituted branched alkyl, for example isononyl, i.e. the ester oil molecule is advantageously symmetrical.
  • the ester oil will preferably be chosen from the following compounds: - isononyl isononanoate, cetostearyl octanoate, isopropyl myristate, 2-ethylhexyl palmitate, 2-octyldodecyl stearate, - 2-octyldodecyl erucate, isostearyl isostearate.
  • the liquid fatty phase may comprise from 0.5% to 100% by weight, preferably from 1% to 80% by weight, more preferably from 2% to 50% by weight and better still from 2% to 40% by weight of ester oil(s) .
  • the liquid fatty phase may represent from 5% to 95%, preferably from 20% to 85% and better still from 40% to 80% of the total weight of the composition.
  • compositions according to the invention may also comprise at least one solid or pasty fatty substance, which may be chosen from waxes and pasty compounds .
  • compositions according to the invention may comprise from 0.1% to 30% by weight, especially from 0.1% to 20% by weight and more particularly from 0.1% to 15% by weight of solid fatty substance (s) relative to the total weight of the composition.
  • the term "wax” means a lipophilic compound that is solid at room temperature (25 0 C) , which undergoes a reversible solid/liquid change of state, and which has a melting point of greater than or equal to 3O 0 C, which may be up to 12O 0 C.
  • the melting point of the wax may be measured using a differential scanning calorimeter (DSC) , for example the calorimeter sold under the name DSC 30 by the company Mettler.
  • DSC differential scanning calorimeter
  • the wax may also have a hardness ranging from 0.05 MPa to 15 MPa and preferably ranging from 6 MPa to 15 MPa.
  • the hardness is determined by measuring the compressive force, measured at 2O 0 C using the texturometer sold under the name TA-TX2i by the company Rheo, equipped with a stainless-steel cylinder 2 mm in diameter travelling at a measuring speed of 0.1 mm/s, and penetrating into the wax to a penetration depth of 0.3 mm .
  • the waxes may be hydrocarbon-based waxes, fluoro waxes and/or silicone waxes, and may be of plant, mineral, animal and/or synthetic origin.
  • the waxes have a melting point of greater than 3O 0 C and better still greater than 45 0 C.
  • compositions may also contain a micronized wax, also known as a microwax.
  • microwaxes that may be used in the compositions according to the invention, mention may be made of carnauba microwaxes, such as the product sold under the name "MicroCare 350 ® " by the company Micro Powders, synthetic microwaxes, such as the product sold under the name “MicroEase 114S” 9 " by the company Micro Powders, microwaxes consisting of a mixture of carnauba wax and polyethylene wax, such as the products sold under the names "Micro Care 300 ® " and “310 ® " by the company Micro Powders, microwaxes consisting of a mixture of carnauba wax and of synthetic wax, such as the product sold under the name "Micro Care 325 " by the company Micro Powders, polyethylene microwaxes, such as the products sold under the names "Micropoly 20O 0 ", “22O 0 ", “22OL 0 " and “250S ® " by the company Micro Powders, and polytetrafluoroethylene microwaxes such
  • microwaxes mentioned above some of them, for instance carnauba microwax, the synthetic microwax “MicroEase 114S ® “ or the microwax consisting of a mixture of carnauba wax and of synthetic wax “MicroCare 325 ® ", have a starting melting point of greater than or equal to 45 0 C.
  • compositions may contain from 0.1% to 50% by weight and better still from 1% to 30% by weight of wax relative to their total weight.
  • compositions may also contain at least one pasty compound, which may be chosen advantageously from:
  • esters the following are especially preferred:
  • esters of a glycerol oligomer especially diglycerol esters, in particular condensates of adipic acid and of glycerol, for which some of the hydroxyl groups of the glycerols have reacted with a mixture of fatty acids such as stearic acid, capric acid, stearic acid and isostearic acid, and 12-hydroxystearic acid, especially such as those sold under the brand name Softisan 649 by the company Sasol, - the arachidyl propionate sold under the brand name Waxenol 801 by Alzo,
  • the gelling agents may be organic or mineral, polymeric or molecular lipophilic gelling agents.
  • Mineral lipophilic gelling agents that may be mentioned include optionally modified clays, for instance hectorites modified with a Ci 0 to C 22 fatty acid ammonium chloride, for instance hectorite modified with distearyldimethylammonium chloride, for instance the product sold under the name Bentone 38V ® by the company Elementis .
  • fumed silica optionally subjected to a hydrophobic surface treatment, the particle size of which is less than 1 ⁇ m.
  • a hydrophobic surface treatment the particle size of which is less than 1 ⁇ m.
  • the hydrophobic groups may be:
  • silica thus treated are known as "silica silylate" according to the CTFA (6th edition, 1995) . They are sold, for example, under the references Aerosil R812 ® by the company Degussa, and Cab-0-Sil TS- 53O 0 by the company Cabot; - dimethylsilyloxyl or polydimethylsiloxane groups, which are obtained especially by treating fumed silica in the presence of polydimethylsiloxane or dimethyldichlorosilane.
  • Silicas thus treated are known as "silica dimethyl silylate" according to the CTFA (6th edition, 1995) . They are sold, for example, under the references Aerosil R972 * and Aerosil R974 * by the company Degussa, and Cab-O-Sil TS-610 0 and Cab-O-Sil TS-72O 0 by the company Cabot.
  • the hydrophobic fumed silica preferably has a particle size that may be nanometric to micrometric, for example ranging from about 5 to 200 nm.
  • the polymeric organic lipophilic gelling agents are, for example, partially or totally crosslinked elastomeric organopolysiloxanes of three-dimensional structure, for instance those sold under the names KSG6 0 , KSG16 0 and KSG18 ® from Shin-Etsu, Trefil E-505C ® or Trefil E-5O6C 0 from Dow Corning, Gransil SR-CYC ® , SR DMF 10 ® , SR-DC556 0 , SR 5CYC gel ® , SR DMF 10 gel ® and SR DC 556 gel ® from Grant Industries and SF 12O4 0 and JK 113 ⁇ from General Electric; ethylcellulose, for instance the product sold under the name Ethocel ® by Dow Chemical; polycondensates of polyamide type resulting from condensation between ( ⁇ ) at least one acid chosen from dicarboxylic acids containing at least 32 carbon atoms, such as fatty acid dimers, and ( ⁇ ) an al
  • fatty acid esters of dextrin such as dextrin palmitates, especially the products sold under the name Rheopearl TL 0 or Rheopearl KL 0 by the company Chiba Flour.
  • composition may, where appropriate, comprise at least one aqueous phase, which may or may not consist essentially of water.
  • It may also comprise a mixture of water and of water- miscible organic solvent (water miscibility of greater than 50% by weight at 25 0 C) , for instance lower monoalcohols containing from 1 to 5 carbon atoms, such as ethanol or isopropanol, glycols containing from 2 to 8 carbon atoms, such as propylene glycol, ethylene glycol, 1,3-butylene glycol or dipropylene glycol, C 3 -C 4 ketones and C 2 -C 4 aldehydes.
  • water miscible organic solvent water miscibility of greater than 50% by weight at 25 0 C
  • lower monoalcohols containing from 1 to 5 carbon atoms, such as ethanol or isopropanol
  • glycols containing from 2 to 8 carbon atoms such as propylene glycol, ethylene glycol, 1,3-butylene glycol or dipropylene glycol, C 3 -C 4 ketones and C 2 -C 4 aldehydes.
  • the aqueous phase (water and optionally the water- miscible organic solvent) may be present in a content ranging from 1% to 95% by weight, especially ranging from 3% to 80% by weight and in particular ranging from 5% to 60% by weight relative to the total weight of the composition.
  • compositions according to the invention may also contain one or more surfactants.
  • they comprise at least one silicone surfactant.
  • the silicone surfactant (s) may be present in the composition in a content ranging from 0.1% to 50% by weight, in particular ranging from 0.1% to 40% by weight, more particularly ranging from 0.5% to 30% by weight, in particular ranging from 0.5% to 20% by weight, and even more particularly ranging from 1% to 10% by weight, relative to the total weight of the composition.
  • surfactants that may be used in the cosmetic compositions in accordance with the present invention, mention may be made more particularly of hydrophilic organopolysiloxanes other than the silicone polymer described hereinabove.
  • hydrophilic radical may correspond to the formula:
  • the units (C 2 H 4 O) and (C 3 H 6 O) may be distributed randomly or in blocks, and
  • - X is a hydrogen or a Ci-Ci 0 alkyl radical, where appropriate substituted with one or more functions of hydroxyl , thiol, amine, carboxylic, carboxylate, amide, phosphate, sulfate or sulfonate type.
  • p may range from 1 to 5 , q from 1 to 100 and r from 1 to 50.
  • X may more particularly feature a hydrogen atom.
  • the organopolysiloxane may comprise as hydrophilic radical at least one hydroxy-polyalkylenoxy radical and especially a hydroxy-polyethylenoxy radical .
  • the organopolysiloxane according to the invention may especially correspond to the formula:
  • R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 and R 10 represent, independently of each other, a linear, branched or cyclic, saturated or unsaturated Ci-C 6 alkyl radical,
  • - HP is a radical bearing at least one hydrophilic group as defined hereinabove
  • - LP is a lipophilic radical
  • - x ranges from 1 to 5000; y from 0 to 5000; z from 0 to 5000.
  • radical LP it may be chosen especially from linear, branched or cyclic Ci-C 40 alkyls, organosiloxane groups, fluorine atoms and aryl , aryloxy, Ci-C 40 hydrocarbyl acyl and hydroxypropylenoxy radicals .
  • the organopolysiloxane belongs to the family of dimethicone-polyethylene glycols and may be chosen especially from the group comprising dimethicone copolyols, in particular cetyldimethicone copolyol and derivatives thereof.
  • the hydrophilic organopolysiloxane according to the present invention may be the product sold under the brand name Abil WE 09 or Abil EM 90 by the company Degussa-Goldschmidt .
  • the hydrophilic organopolysiloxane according to the present invention may also be the product sold under the reference KF- 6017 by the company Shin-Etsu.
  • the organopolysiloxane compound may be totally or partially fluorinated.
  • the lower dialkyl siloxy groups may be substituted with one or more fluorine atoms.
  • the silicone surfactant that may be used in the cosmetic compositions in accordance with the present invention is chosen from dimethicone copolyol, dimethicone copolyol benzoate, dimethicone copolyol phosphates, polyoxyalkylenated silicone elastomers and the cyclomethicone/dimethicone mixture, and mixtures thereof .
  • Polyoxyalkylenated silicone elastomers such as those described in patents US 5 236 986, US 5 412 004, US 5 837 793 and US 5 811 487, the content of which is incorporated by reference, are also suitable according to the invention.
  • Polyoxyalkylenated silicone elastomers that may be used include those sold under the names “KSG-21”, “KSG-20”, “KSG-30”, “KSG-31”, “KSG-32”, “KSG-33”, “KSG-210”, “KSG-310”, “KSG-320”, “KSG-330”, “KSG-340” and “X- 226146” by the company Shin-Etsu, and "DC 9010” and “DC 9011” by the company Dow Corning.
  • compositions according to the invention may also comprise anionic and/or nonionic non-silicone surfactants.
  • the surfactants that may be used more particularly in the composition according to the invention are chosen from:
  • fatty acids fatty alcohols, polyethoxylated or polyglycerolated fatty alcohols such as polyethoxylated stearyl or cetylstearyl alcohol, fatty acid esters of sucrose, alkyl glucose esters, in particular polyoxyethylenated fatty esters of a Ci-C 6 alkyl glucose, and mixtures thereof ,
  • composition according to the invention may also contain at least one organic or mineral dyestuff, especially of the type such as pigments or nacres.
  • composition according to the invention may also contain at least one dyestuff chosen from lipophilic dyes, hydrophilic dyes, pigments, nacres and materials with a specific optical effect, and mixtures thereof.
  • This dyestuff may be present in a proportion of from 0.01% to 50% by weight relative to the total weight of the composition, in particular from 0.5% to 40% by weight, more particularly from 5% to 25%, especially from 0.01% to 20% and in particular from 0.1% to 10%, or even from 2% to 5% by weight, relative to the total weight of the composition.
  • pigments should be understood as meaning white or coloured, mineral or organic particles, which are insoluble in an aqueous solution and which are intended to colour and/or opacify the resulting film.
  • the pigments may be present in a proportion of from 0.01% to 20% by weight, especially from 0.01% to 5% by weight and in particular from 0.02% to 7% by weight relative to the total weight of the cosmetic composition.
  • mineral pigments that may be used in the invention, mention may be made of titanium oxide, zirconium oxide or cerium oxide, and also zinc oxide, iron oxide or chromium oxide, ferric blue, manganese violet, ultramarine blue and chromium hydrate.
  • pigments may also be pigments with a structure that may be, for example, of sericite/brown iron oxide/titanium dioxide/silica type.
  • a pigment is sold, for example, under the reference Coverleaf * NS or JS by the company Chemicals and Catalysts, and has a contrast ratio in the region of 30.
  • the dyestuff may also comprise a pigment with a structure that may be, for example, of silica microsphere type containing iron oxide.
  • a pigment having this structure is the product sold by the company Miyoshi under the reference PC Ball * PC-LL- 100 P, this pigment consisting of silica microspheres containing yellow iron oxide.
  • DPP diketopyrrolopyrroles
  • nacres should be understood as meaning iridescent or non-iridescent coloured particles of any form, especially produced by certain molluscs in their shell, or else synthesized, and which have a colour effect by optical interference.
  • the nacres may be chosen from nacreous pigments such as titanium mica coated with an iron oxide, mica coated with bismuth oxychloride, titanium mica coated with chromium oxide, titanium mica coated with an organic dye and also nacreous pigments based on bismuth oxychloride. They may also be mica particles at the surface of which are superposed at least two successive layers of metal oxides and/or of organic dyestuffs.
  • nacres examples include natural mica coated with titanium oxide, with iron oxide, with natural pigment or with bismuth oxychloride .
  • Timiron * nacres sold by the company Merck the Prestige * nacres on a mica base, sold by the company Eckart, and the Sunshine * nacres on a synthetic mica base, sold by the company Sun Chemical.
  • the nacres may more particularly have a yellow, pink, red, bronze, orange, brown, gold and/or coppery colour or glint.
  • the pigments may or may not be surface-coated, in particular surface-treated with silicones, amino acids, fluoro derivatives or any other substance that promotes the dispersion and compatibility of the pigment in the composition.
  • the pigments used in the compositions in accordance with the invention may be surface-coated with a lecithin coating.
  • This coating may be obtained by placing a solution of pigment in contact with a lecithin solution, in the presence of divalent or trivalent metal salts. Hydrogenated or non-hydrogenated lecithin may be used to obtain this coating.
  • the cosmetic composition according to the invention may also comprise water-soluble or liposoluble dyes in a content ranging from 0.01% to 10% by weight and especially ranging from 0.01% to 5% by weight relative to the total weight of the cosmetic composition.
  • the liposoluble dyes are, for example, Sudan red, DC Red 17, DC Green 6, ⁇ -carotene, soybean oil, Sudan brown, DC Yellow 11, DC Violet 2, DC Orange 5 and quinoline yellow.
  • compositions according to the invention comprise a water-soluble dye
  • this dye may be present in the composition in dispersed form.
  • the cosmetic composition according to the invention may also contain at least one material with a specific optical effect.
  • This effect is different from a simple conventional hue effect, i.e. a unified and stabilized effect as produced by standard dyestuffs, for instance monochromatic pigments.
  • stabilized means lacking an effect of variability of the colour as a function of the angle of observation or alternatively in response to a temperature change .
  • this material may be chosen from particles with a metallic glint, goniochromatic colouring agents, diffracting pigments, thermochromic agents, optical brighteners, and also fibres, especially interference fibres. Needless to say, these various materials may be combined so as to simultaneously afford two effects, or even a novel effect in accordance with the invention.
  • the particles with a metallic glint that may be used in the invention are chosen in particular from:
  • - particles comprising a mono-material or multi- material organic or mineral substrate, at least partially coated with at least one coat with a metallic glint comprising at least one metal and/or at least one metal derivative, and
  • Cu, Al, Zn, Ni, Mo and Cr and mixtures or alloys thereof are preferred metals.
  • metal derivatives is intended to denote compounds derived from metals, especially oxides, fluorides, chlorides and sulfides.
  • aluminium particles such as those sold under the names Starbrite 1200 EAC * by the company Siberline, and Metalure 0 by the company Eckart .
  • copper metal powders or alloy mixtures such as the reference 2844 sold by the company Radium Bronze, metallic pigments such as aluminium or bronze, such as those sold under the name Rotosafe 0 700 from the company Eckart, the silica- coated aluminium particles sold under the name Visionaire Bright Silver 0 from the company Eckart and metal alloy particles, for instance the silica-coated bronze (alloy of copper and zinc) powders sold under the name Visionaire Bright Natural Gold * from the company Eckart .
  • They may also be particles comprising a glass substrate, such as those sold by the company Nippon Sheet Glass under the name Microglass Metashine ® .
  • the goniochromatic colouring agent may be chosen, for example, from multilayer interference structures and liquid-crystal colouring agents.
  • symmetrical multilayer interference structures that may be used in the 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 company Dupont de Nemours,- Cr/MgF 2 /Al/MgF 2 /Cr, pigments having this structure being sold under the name Chromaflair by the company Flex,- MoS 2 /Si0 2 /Al/Si0 2 /MoS 2 ; Fe 2 0 3 /Si0 2 /Al/Si0 2 /Fe 2 0 3 , and Fe 2 O 3 /SiO 2 /Fe 2 O 3 /SiO 2 /Fe 2 O 3 , pigments having these structures being sold under the name Sicopearl by the company BA
  • these pigments may be the pigments of silica/titanium oxide/tin oxide structure sold under the name Xirona Magic * by the company Merck, the pigments of silica/brown iron oxide structure sold under the name Xirona Indian Summer * by the company Merck and the pigments of silica/titanium oxide/mica/tin oxide structure sold under the name Xirona Caribbean Blue 0 by the company Merck. Mention may also be made of the Infinite Colors * pigments from the company Shiseido. Depending on the thickness and the nature of the various layers, different effects are obtained.
  • the colour changes from green-golden to red- grey for SiO 2 layers of 320 to 350 nm; from red to golden for SiO 2 layers of 380 to 400 nm; from violet to green for SiO 2 layers of 410 to 420 nm; from copper to red for SiO 2 layers of 430 to 440 nm.
  • pigments with a polymeric multilayer structure examples include those sold by the company 3M under the name Color Glitter.
  • liquid-crystal goniochromatic particles that may be used include those sold by the company Chenix and also the products sold under the name Helicone * HC by the company Wacker.
  • composition of the invention may also comprise any ingredient usually used in the field under consideration.
  • composition according to the invention also comprises solid particles chosen from fillers.
  • composition according to the invention may be in the form of a dermatological or care composition for keratin materials such as the skin, the lips and/or the integuments, in the form of an antisun composition or a makeup-removing composition, in stick form or in cast form. It may especially be used as a care base for the skin, the integuments or the lips (lip balms, for protecting the lips against the cold and/or the sun and/or the wind, or a care cream for the skin, the nails or the hair) .
  • composition of the invention may also be in the form of a coloured makeup product for the skin, in particular a foundation, optionally having care or treatment properties, a blusher, a makeup rouge, an eyeshadow, a concealer product, an eyeliner, a body makeup product; a lip makeup product, for instance a lipstick, a lip gloss or a lip pencil, optionally having care or treatment properties; a makeup product for the integuments, for instance the nails, for the eyelashes, in particular in the form of a mascara, or for the eyebrows and the hair.
  • composition of the invention should be cosmetically or dermatologically acceptable, i.e. it should contain a non-toxic physiologically acceptable medium and should be able to be applied to human skin, integuments or lips.
  • cosmetically acceptable means a composition of pleasant appearance, odour and feel.
  • the invention also relates to a cosmetic assembly comprising: i) a container delimiting at least one compartment, the said container being closed by means of a closing member; and ii) a composition placed inside the said compartment, the composition being in accordance with the invention.
  • the container may be in any adequate form. It may especially be in the form of a bottle, a tube, a jar, a case, a box, a sachet or a carton.
  • the closing member may be in the form of a removable stopper, a lid, a cap, a tear-off strip or a capsule, especially of the type comprising a body attached to the container and a cover cap articulated on the body.
  • It may also be in the form of a member for selectively closing the container, especially a pump, a valve or a flap valve.
  • the container may be combined with an applicator, especially in the form of a brush comprising an arrangement of bristles maintained by a twisted wire.
  • a twisted brush is described especially in patent US 4 887 622. It may also be in the form of a comb comprising a plurality of application members, obtained especially by moulding. Such combs are described, for example, in patent FR 2 796 529.
  • the applicator may be in the form of a fine brush, as described, for example, in patent FR 2 722 380.
  • the applicator may be in the form of a block of foam or of elastomer, a felt or a spatula.
  • the applicator may be free (tuft or sponge) or securely fastened to a rod borne by the closing member, as described, for example, in patent US 5 492 426.
  • the applicator may be securely fastened to the container, as described, for example, in patent FR 2 761 959.
  • the product may be contained directly in the container, or indirectly.
  • the product may be arranged on an impregnated support, especially in the form of a wipe or a pad, and arranged (individually or in plurality) in a box or in a sachet.
  • an impregnated support especially in the form of a wipe or a pad, and arranged (individually or in plurality) in a box or in a sachet.
  • Such a support incorporating the product is described, for example, in patent application WO 01/03538.
  • the closing member may be coupled to the container by screwing.
  • the coupling between the closing member and the container is done other than by screwing, especially via a bayonet mechanism, by click- fastening, gripping, welding, bonding or by magnetic attraction.
  • click-fastening in particular means any system involving the crossing of a bead or cord of material by elastic deformation of a portion, especially of the closing member, followed by return to the elastically unconstrained position of the said portion after the crossing of the bead or cord.
  • the container may be at least partially made of thermoplastic material .
  • thermoplastic materials that may be mentioned include polypropylene or polyethylene.
  • the container is made of non- thermoplastic material, especially glass or metal (or al loy) .
  • the container may have rigid walls or deformable walls, especially in the form of a tube or a tubular bottle.
  • the container may comprise means for initiating or facilitating the distribution of the composition.
  • the container may have deformable walls so as to allow the composition to exit in response to a positive pressure inside the container, this positive pressure being caused by elastic (or non-elastic) squeezing of the walls of the container.
  • the product may be driven out by a piston mechanism.
  • the container may comprise a mechanism, especially a rack mechanism, a threaded-rod mechanism or a helical groove mechanism, and may be capable of moving a stick in the direction of the said aperture.
  • a mechanism is described, for example, in patent FR 2 806 273 or in patent FR 2 775 566.
  • Such a mechanism for a liquid product is described in patent FR 2 727 609.
  • the container may consist of a carton with a base delimiting at least one housing containing the composition, and a lid, especially articulated on the base, and capable of at least partially covering the said base.
  • a carton is described, for example, in patent application WO 03/018423 or in patent FR 2 791 042.
  • the container may be equipped with a drainer arranged in the region of the aperture of the container.
  • a drainer makes it possible to wipe the applicator and possibly the rod to which it may be securely fastened.
  • a drainer is described, for example, in patent FR 2 792 618.
  • the composition may be at atmospheric pressure inside the container (at room temperature) or pressurized, especially by means of a propellent gas (aerosol) . In the latter case, the container is equipped with a valve (of the type used for aerosols) .
  • compositions that are the subject of the present patent application, they should be prepared according to a process comprising at least one step of controlled, preferably continuous shear of all or part of the fatty phase structured with the silicone compound, advantageously at a temperature greater than or equal to the solid- liquid transition temperature of the silicone polymer.
  • the present patent application also relates to a process for preparing a composition according to the present invention, comprising at least one step of controlled, preferably continuous shear of all or part of the fatty phase structured with the silicone compound, advantageously at a temperature greater than or equal to the solid-liquid transition temperature of the silicone polymer.
  • the process comprises at least one step of controlled shear of all the ingredients of the composition, advantageously at a temperature greater than or equal to the solid-liquid transition temperature of the silicone polymer.
  • any equipment or combination of equipment allowing the management of a mechanical action for blending the product gradually as it is prepared such as processes functioning continuously of scraped- surface exchanger type, or preferably of twin-screw blender-extruder type (referred to as "extruder" for simplicity in the rest of this document) is suitable for performing the process according to the invention.
  • Extruders of twin-screw blender-extruder type are preferably used, these extruders being composed of the following components: - at least two sheaths independently thermally regulated to a temperature ranging from 1O 0 C to 300 0 C, two co-rotating axes composed of screw components, each component having a shape that affords the desired mixing function in the corresponding temperature region, devices for metering out and introducing the various phases,
  • variable-speed motor allowing the intensity of the shear to be modulated as a function of the spin speed of the screws.
  • the various ingredients may be incorporated at different temperatures in the course of the blending during cooling, at a temperature that is compatible with their stability.
  • the extruder consists of six independent barrels, each allowing the introduction of new phases and setting of the temperature. They are numbered from 1 to 6 starting from the inlet to the outlet of the product.
  • the spin speed is 50 rpm and the flow rate is 0.7 kg/hour.
  • the fatty phase is heated to HO 0 C in a heating pan with stirring, the preground pigments are then added and the mixture is heated for 45 minutes. The mixture is then introduced into the extruder.
  • the above lipstick composition (Example 1) is prepared according to the process of the invention in a twin-screw mixer-extruder (Prism Eurolab type from the company ThermoRheo) described above according to the following procedure: The silicone polymer, the silicone surfactant (cetyl dimethicone) , the oils (polyisobutene, polydimethyl- siloxane and phenyl trimethicone) and the wax are weighed out in a heating pan. The mixture is heated to HO 0 C with stirring using a Rayneri blender. When the mixture is molten, the preground pigments are introduced into the three-roll mill and heating of the resulting mixture is continued for 45 minutes. The fragrance is then added.
  • a twin-screw mixer-extruder Prism Eurolab type from the company ThermoRheo
  • the mixture is then placed on a stirring plate located close to the extruder and maintained at the required temperature by means of an oil bath (nominal temperature 12O 0 C) .
  • the mixture is introduced into the extruder using a pump: the spin speed of the screws is 50 rpm and the feed rate provided by the pump is 0.7 kg/hour.
  • a Petri dish comprising the composition collected at the extruder outlet is then prepared.
  • the initial and final hardnesses were measured at 2O 0 C according to the protocols described above, and the ⁇ hardness and the ratio between the final hardnesses at 2O 0 C after heating to HO 0 C and the initial hardness at 2O 0 C before heating, were calculated.

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  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Birds (AREA)
  • Epidemiology (AREA)
  • Cosmetics (AREA)

Abstract

L'invention concerne une composition cosmétique comprenant une phase grasse comprenant au moins un polymère de type silicone comprenant au moins une unité comprenant : 1) des polyorganosiloxanes comprenant au moins deux groupes capables de former des liaisons hydrogène, ces deux groupes étant situés dans la chaîne du polymère et/ou 2) des polyorganosiloxanes comprenant au moins deux groupes capables de former des liaisons hydrogène, ces deux groupes étant situés sur des parties greffées ou des ramifications, ladite composition étant telle que, après avoir été soumise à une température de 110°C, elle a une variation de dureté, correspondant à la différence entre la dureté finale à 20°C après chauffage et la dureté initiale à 20°C avant chauffage, d'au moins 10 g.
PCT/EP2006/068176 2005-11-09 2006-11-07 Composition cosmétique comprenant un polymère de type silicone servant à structurer une phase grasse, caractérisée par une dureté WO2007054492A1 (fr)

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
FR0553394A FR2892929B1 (fr) 2005-11-09 2005-11-09 Composition cosmetique comprenant un polymere silicone structurant de phase grasse caracterisee par une durete
FR0553394 2005-11-09
US73687405P 2005-11-16 2005-11-16
US60/736,874 2005-11-16

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WO2007054492A1 true WO2007054492A1 (fr) 2007-05-18

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Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2018165434A1 (fr) 2017-03-08 2018-09-13 Dow Silicones Corporation Composition cosmétique de longue durée comprenant un élastomère de silicone
US10780039B2 (en) 2016-06-10 2020-09-22 Conopco, Inc. Personal care composition
US10898428B2 (en) 2016-06-10 2021-01-26 Conopco, Inc. Personal care composition
US11253463B2 (en) 2018-01-08 2022-02-22 Conopco, Inc. Cosmetic compositions comprising silicone elastomer and emollient

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Publication number Priority date Publication date Assignee Title
EP0667146A1 (fr) * 1994-01-25 1995-08-16 L'oreal Composition cosmétique ou dermopharmaceutique sous forme de pâte souple et procédé de préparation
EP1177784A2 (fr) * 2000-08-04 2002-02-06 Unilever Plc Compositions antitranspiration
US20020051758A1 (en) * 2000-08-31 2002-05-02 Heng Cai Clear antiperspirants and deodorants made with siloxane-based polyamides
EP1266647A1 (fr) * 2001-06-14 2002-12-18 L'oreal Composition a base d'huile siliconée structurée sous forme rigide, notamment pour une utilisation cosmétique
EP1266648A1 (fr) * 2001-06-14 2002-12-18 L'oreal Composition à base d'huile siliconée structurée sous forme rigide, notamment pour une utilisation cosmétique
US20030232030A1 (en) * 2002-06-12 2003-12-18 L'oreal Compositions containing at least one oil structured with at least one silicone-polyamide polymer, and at least one gelling agent and methods of using the same
US20030235553A1 (en) * 2002-06-12 2003-12-25 L'oreal Cosmetic compositions containing at least one silicone-polyamide polymer, at least one oil and at least one film-forming agent and methods of using the same
US20040170586A1 (en) * 2002-06-12 2004-09-02 L'oreal Cosmetic composition containing a polyorganosiloxane polymer

Patent Citations (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0667146A1 (fr) * 1994-01-25 1995-08-16 L'oreal Composition cosmétique ou dermopharmaceutique sous forme de pâte souple et procédé de préparation
EP1177784A2 (fr) * 2000-08-04 2002-02-06 Unilever Plc Compositions antitranspiration
US20020051758A1 (en) * 2000-08-31 2002-05-02 Heng Cai Clear antiperspirants and deodorants made with siloxane-based polyamides
EP1266647A1 (fr) * 2001-06-14 2002-12-18 L'oreal Composition a base d'huile siliconée structurée sous forme rigide, notamment pour une utilisation cosmétique
EP1266648A1 (fr) * 2001-06-14 2002-12-18 L'oreal Composition à base d'huile siliconée structurée sous forme rigide, notamment pour une utilisation cosmétique
US20030232030A1 (en) * 2002-06-12 2003-12-18 L'oreal Compositions containing at least one oil structured with at least one silicone-polyamide polymer, and at least one gelling agent and methods of using the same
US20030235553A1 (en) * 2002-06-12 2003-12-25 L'oreal Cosmetic compositions containing at least one silicone-polyamide polymer, at least one oil and at least one film-forming agent and methods of using the same
US20040170586A1 (en) * 2002-06-12 2004-09-02 L'oreal Cosmetic composition containing a polyorganosiloxane polymer

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US10780039B2 (en) 2016-06-10 2020-09-22 Conopco, Inc. Personal care composition
US10898428B2 (en) 2016-06-10 2021-01-26 Conopco, Inc. Personal care composition
WO2018165434A1 (fr) 2017-03-08 2018-09-13 Dow Silicones Corporation Composition cosmétique de longue durée comprenant un élastomère de silicone
US10918587B2 (en) 2017-03-08 2021-02-16 Dow Silicones Corporation Long lasting cosmetic composition comprising silicone elastomer
US11253463B2 (en) 2018-01-08 2022-02-22 Conopco, Inc. Cosmetic compositions comprising silicone elastomer and emollient

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