WO2013190705A1 - Composition cosmétique comprenant un polymère supramoléculaire, une huile de silicone non volatile et une huile d'hydrocarbure non volatile - Google Patents

Composition cosmétique comprenant un polymère supramoléculaire, une huile de silicone non volatile et une huile d'hydrocarbure non volatile Download PDF

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Publication number
WO2013190705A1
WO2013190705A1 PCT/JP2012/066465 JP2012066465W WO2013190705A1 WO 2013190705 A1 WO2013190705 A1 WO 2013190705A1 JP 2012066465 W JP2012066465 W JP 2012066465W WO 2013190705 A1 WO2013190705 A1 WO 2013190705A1
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Prior art keywords
oil
composition
phenyl
radical
composition according
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PCT/JP2012/066465
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English (en)
Inventor
Momoko Shimizu
Romain TACHON
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L'oreal
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Priority to JP2014561202A priority Critical patent/JP2015523959A/ja
Priority to PCT/JP2012/066465 priority patent/WO2013190705A1/fr
Publication of WO2013190705A1 publication Critical patent/WO2013190705A1/fr

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Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/31—Hydrocarbons
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
    • A61K8/81—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds
    • A61K8/8105—Compositions of homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Compositions of derivatives of such polymers
    • A61K8/8111—Homopolymers or copolymers of aliphatic olefines, e.g. polyethylene, polyisobutene; Compositions of derivatives of such polymers
    • 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
    • A61K8/81—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds
    • A61K8/817—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a single or double bond to nitrogen or by a heterocyclic ring containing nitrogen; Compositions or derivatives of such polymers, e.g. vinylimidazol, vinylcaprolactame, allylamines (Polyquaternium 6)
    • A61K8/8182—Copolymers of vinyl-pyrrolidones. Compositions of derivatives of such polymers
    • 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
    • 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

Definitions

  • the present invention relates to a cosmetic composition, more particularly to a cosmetic composition for making up and/or caring for the skin and/or the lips, comprising at least one supramolecular polymer, a non volatile silicone oil and a non volatile hydrocarbonated oil.
  • the present invention also relates to the processes using such composition for making up and/or caring for the skin and/or the lips, comprising the application to the skin and/or the lips of such cosmetic composition.
  • compositions of this type include silicone resins, polyacrylates and latices.
  • the aim of the present invention is to overcome these drawbacks and to propose a cosmetic composition that is homogenous, stable (for example no separation into two phases, and/or exsudation, and/or sedimentation of the pigments, in particular after 24hours at room temperature, or even after 72 hours at room temperature), and capable, on the one hand, of affording good cosmetic properties such as glide and easiness to apply, in particular on the lips, good adhesion to the support (skin or lips) and thus good remanence of the deposit of the composition, in particular no or low level transfer of the color of the deposit, and forming a non-tacky or sparingly tacky deposit, having a good level of shine.
  • the invention relates to a cosmetic composition for making up and/or caring for the skin and/or the lips, comprising in a physiologically acceptable medium, at least one supramolecular polymer based on a functionalized polyalkene of formula HO-P-OH in which P represents a homopolymer or a copolymer that may be obtained by polymerization of one or more linear, cyclic and/or branched polyunsaturated C 2 -C 10 and preferably C 2 -C 4 alkenes, which may be derived from the reaction, especially the condensation, of the said functionalized polyalkene polymer with at least one junction group functionalized with at least one reactive group capable of reacting with the reactive group(s) of the functionalized polyalkene polymer, the said junction group being capable of forming at least 3 H (hydrogen) bonds, preferably at least 4 H bonds, preferentially 4 H bonds, at least one non volatile silicone oil, preferably phenylated, and at least one non volatile hydrocarbon
  • Such a composition is stable and homogenous, and are preferably makeup compositions, whose deposition on keratin materials, and in particular the lips and/or the skin, is easy, uniform, has a good level of shine and has good remanence (no embrittlement or fragmentation of the deposit) and good transfer resistance after application (in particular, no transfer or poor transfer of the color of the deposit, in particular on a cup or a glass while drinking for example) and/or sparingly tacky or non-tacky.
  • Such a deposit may especially afford a sensation of comfort to the wearer.
  • the present invention also relates to a cosmetic process for making up and/or caring for the skin and/or the lips, comprising at least the application to the said skin and/or the said lips of composition comprising, in a physiologically acceptable medium, at least one supramolecular polymer as defined above, at least one non volatile silicone oil, and at least one non volatile hydrocarbonated oil.
  • the composition under consideration according to the invention is an oil-in-oil type composition.
  • the non volatile silicone oil and the non volatile hydrocarbon oil is in a stable oil in oil state before application, without being separated from each other. After application, the non volatile silicone oil comes up to the surface of the deposit, and this separated non volatile silicone oil covers an adherent layer of the non volatile hydrocarbonated oil and the supramolecular polymer. Therefore, the resulting composition has good transfer resistance and offers a good level of shine. Rubbing t he lips again each other during application further enhance this separation.
  • composition under consideration according to the invention is anhydrous.
  • At least one said non volatile silicone oil is chosen from non volatile linear phenyl silicone oil.
  • At least one said non volatile hydrocarbonated oil is chosen from apolar non volatile hydrocarbonated oil.
  • physiologically acceptable medium is intended to denote a medium that is suitable for the application of a composition to the skin and/or the lips, for instance the oils or organic solvents commonly used in cosmetic compositions.
  • the physiologically acceptable medium (acceptable tolerance, toxicology and feel) is generally adapted to the nature of the support onto which the composition is to be applied, and also to the form in which the composition is to be conditioned.
  • the combination under consideration according to the invention proves to be most particularly effective for affording a composition whose deposit on the skin or the lips that simultaneously has improved gloss and non transfer properties.
  • the deposit also exibit remanence over time, in particular of remanence of the colour of the deposit (no embrittlement or fragmentation of the deposit, which remains homogeneous) and satisfactory comfort properties, both on application (especially glidance, breakdown, thickness and uniformity of the deposit formed, and reduction of the tack on drying) and during wearing, namely softness, absence of a tacky sensation or of a sensation of tautness or dryness.
  • the invention also preferably relates to a composition for making up and/or caring for the skin and/or the lips, comprising, in a physiologically acceptable medium, at least one supramolecular polymer, at least one non volatile silicone oil, at least one non volatile hydrocarbonated oil, and at least one colouring agent.
  • compositions under consideration according to the invention and used in the processes according to the invention may be in solid or liquid form at 20°C.
  • the composition used according to the invention is anhydrous or contains less than 3% by weight of water and preferably less than 1% by weight of water, relative to the total weight of the composition.
  • anhydrous especially means that water is preferably not deliberately added to the composition, but may be present in trace amount in the various compounds used in the composition.
  • composition according to the invention and/or that used according to the process according to the invention may be in the form of a composition for making up the skin and/or the lips, especially for facial or bodily skin; it may be a complexion product such as a foundation, a face powder or an eyeshadow; a lip product such as a lipstick or a lipcare product; a concealer product; a blusher; an eyeliner; a lip pencil or an eye pencil; a body makeup product; a gloss (lip gloss).
  • the composition is intended for making up the lips and it is more particularly a lipstick (lipstick wand) or a gloss (liquid lipstick).
  • the lipstick compositions according to the invention are anhydrous.
  • solid characterizes the state of the composition at a temperature of 20°C.
  • a solid composition according to the invention has, at a temperature of 20°C and at atmospheric pressure (760 mmHg), a hardness of greater than 30 Nm "1 and preferably greater than 35 Nm "1 .
  • Protocol for measuring the hardness The hardness of a composition especially of lipstick wand type is measured according to the following protocol:
  • the stick of lipstick is stored at 20°C for 24 hours before measuring the hardness.
  • the hardness may be measured at 20°C via the "cheese wire” method, which consists in transversely cutting a wand of product, which is preferably a circular cylinder, by means of a rigid tungsten wire 250 ⁇ in diameter, by moving the wire relative to the stick at a speed of 100 mm/minute.
  • the hardness of the samples of compositions of the invention is measured using a DFGS2 tensile testing machine from the company Indelco-Chatillon.
  • the measurement is repeated three times and then averaged.
  • the average of the three values read using the tensile testing machine mentioned above, noted Y, is given in grams. This average is converted into newtons and then divided by L which represents the longest distance through which the wire passes. In the case of a cylindrical wand, L is equal to the diameter (in metres).
  • a solid composition according to the invention has a hardness at 20°C of greater than or equal to 30 Nm "1 , preferably greater than 35 Nm '1 and preferably greater than 40 Nm "1 .
  • the composition according to the invention especially has a hardness at 20°C of less than 500 Nm '1 , especially less than 400 Nm "1 and preferably less than 300 Nm "1 .
  • composition whose hardness is greater than 30 Nm "1 is said to be "solid” at 20°C and at atmospheric pressure (760 mmHg).
  • the composition according to the invention is liquid at 20°C.
  • the viscosity measurement is generally performed at 25°C, using a Rheomat RM180 viscometer equipped with a No. 4 spindle, the measurement being performed after 10 minutes of rotation of the spindle in the composition (after which time stabilization of the viscosity and of the spin speed of the spindle are observed), at a shear rate of 200 rpm.
  • the composition has at 25°C a viscosity of between 1 and 25 Pa.s, preferably between 2 and 20 Pa.s and preferably between 4 and 17 Pa.s.
  • the viscosity at 25°C of a composition according to the invention is between 5 and 16 Pa.s.
  • the present invention also covers a cosmetic process for making up and/or caring for the lips, comprising at least the application to the said lips of a composition as defined above.
  • the cosmetic compositions according to the invention thus comprise a polyalkene-based polyolefin) supramolecular polymer.
  • polyalkene-based supramolecular polymer means a polymer derived from the reaction, especially the condensation, of at least one polyalkene polymer functionalized with at least one reactive group, with at least one junction group functionalized with at least one reactive group capable of reacting with the reactive group(s) of the functionalized polyalkene polymer, said junction group being capable of forming at least three H (hydrogen) bonds and preferably at least four H bonds, preferentially four H bonds.
  • polyalkene or "polyolefin” means a polymer derived from the polymerization of at least one monomer of alkene type, comprising an ethylenic unsaturation, the said monomer possibly being pendent or in the main chain of the said polymer.
  • polyalkene or “polyolefin” is thus directed towards polymers that may or may not comprise a double bond.
  • the supramolecular polymers used according to the invention are prepared from a polymer derived from the polymerization of an alkene comprising at least two ethylenic unsaturations.
  • the supramolecular polymer according to the invention is capable of forming a supramolecular polymer chain or network, by (self-)assembly of said polymer according to the invention with at least one other identical or different polymer according to the invention, each assembly involving at least one pair of paired junction groups, which may be identical or different, borne by each of the polymers according to the invention.
  • junction group means any group comprising groups that donate or accept H bonds, and capable of forming at least three H bonds and preferably at least four H bonds, preferentially four H bonds, with an identical or different partner junction group. These junction groups may be lateral to the polymer backbone (side branching) and/or borne by the ends of the polymer backbone, and/or in the chain forming the polymer backbone. They may be distributed in a random or controlled manner.
  • the polyalkene polymers are functionalized with at least one reactive group and preferably with at least two reactive groups.
  • the functionalization preferably occurs at the chain ends. They are then referred to as telechelic polymers.
  • the functionalization groups, or reactive groups may be attached to the polyalkene polymer via linkers, preferably linear or branched Ci-C 4 alkylene groups, or directly via a single bond.
  • the functionalized polyalkene polymers have a number-average molecular mass (Mn) of between 1000 and 8000.
  • the functionalized polyalkene polymer capable of forming all or part of the polymer backbone of the supramolecular polymer according to the invention (preferably, it forms all of the backbone of the polymer), is of formula HO-P-OH in which:
  • - P represents a homo- or copolymer that may be obtained by polymerization of one or more linear, cyclic and/or branched, polyunsaturated (preferably diunsaturated) C 2 -C 10 and preferably C 2 -C 4 alkenes.
  • P preferably represents a homo- or copolymer that may be obtained by polymerization of one or more linear, cyclic and/or branched, C 2 -C 4 diunsaturated alkenes.
  • P represents a polymer chosen from a polybutylene, a polybutadiene (such as a 1,4- polybutadiene or a 1,2-polybutadiene), a polyisoprene, a poly(l,3-pentadiene) and a polyisobutylene, and copolymers thereof.
  • P represents a poly(ethylene/butylene) copolymer.
  • the preferred poly(ethylene/butylenes) are copolymers of 1-butene and of ethylene. They may be represented schematically by the following sequence of units:
  • P is a polybutadiene homopolymer, preferably chosen from a 1,4-polybutadiene or a 1,2-polybutadiene.
  • the polybutadienes may be 1,4-polybutadienes or 1,2-polybutadienes, which may be represented schematically, respectively, by the following sequences of units:
  • they are 1,2-polybutadienes.
  • P is a 1,2-polybutadiene homopolymer.
  • P is a polyisoprene.
  • Polyisoprenes may be represented schematically by the following sequences of units:
  • a mixture of above units may obviously also be used, so as to form copolymers.
  • the functionalized polyalkene polymers may be totally hydrogenated to avoid the risks of crosslinking.
  • the functionalized polyalkene polymers used in the compositions according to the invention are hydrogenated.
  • the polyalkene polymers are hydrogenated and functionalized with at least two OH reactive groups, preferably at the ends of the polymers.
  • polydienes containing hydroxyl end groups are especially defined, for example, in FR 2782723. They may be chosen from polybutadiene, polyisoprene and poly(l,3-pentadiene) homopolymers and copolymers. Mention will be made in particular of the hydroxylated polybutadienes sold by the company Sartomer, for instance the Krasol® Resins and the Poly bd® Resins.
  • dihydroxylated hydrogenated 1,2-polybutadiene homopolymers such as the range Nisso-PB 1, GI3000, GI2000 and Gil 000 sold by the company Nisso, which may be represented schematically by the following formula:
  • n is between 14 and 105 and preferably between 20 and 85.
  • Length 150 mm - inside diameter: 7.5 mm
  • polystyrene resin with hydroxyl end groups
  • the supramolecular polymers according to the invention also have in their structure at least one residue of a junction group capable of forming at least three H bonds and preferably at least four H bonds, said junction group being initially functionalized with at least one reactive group.
  • junction group means in the present description the group without its reactive function.
  • the reactive groups are attached to the junction group via linkers L.
  • L is a single bond or a saturated or unsaturated -20 divalent carbon-based group chosen in particular from a linear or branched -C20 alkylene; a C 5 -C 20 (alkyl)cycloalkylene alkylene (preferably cyclohexylene methylene), a Cn-C 2 o alkylene-biscycloalkylene (preferably alkylene- biscyclohexylene), a C 6 -C 2 o (alkyl)arylene, an alkylene-bisarylene (preferably an alkylene- biphenylene), the linker L possibly being substituted with at least one alkyl group and/or possibly comprising 1 to 4 N and/or O heteroatoms, especially in the form of an N0 2 substituent.
  • the linker is a group chosen from phenylene; 1,4-nitrophenylene; 1,2-ethylene; 1,6- hexylene; 1,4-butylene; l,6-(2,4,4-trimethylhexylene); l,4-(4-methylpentylene); 1 ,5-(5- methylhexylene); l,6-(6-methylheptylene); l,5-(2,2,5-trimethylhexylene); l,7-(3,7-dimethyloctylene); -isophorone-; 4,4 '-methylene bis(cyclohexylene); tolylene; 2-methyl- 1,3 -phenylene; 4-methyl-l,3- phenylene; 4,4-biphenylenemethylene;
  • the linker is chosen from the groups:
  • - Cn-C 25 alkylene-biscycloalkylene such as 4,4'-methylene biscyclohexene, - C1-C20 alkylene, such as -(CH 2 )2-; -(CH 2 ) 6 -; -CH 2 CH(CH 3 )-CH 2 -C(CH 3 )2-CH2-CH2, and
  • L is chosen from: -isophorone-; -(CH 2 )2-; -(CH 2 ) 6 -; -CH 2 CH(CH 3 )-CH 2 -C(CH 3 )2-CH2- CH 2 ; 4,4'-methylenebis(cyclohexylene); 2-methyl-l,3-phenylene.
  • the linker is an alkylcycloalkylene alkylene.
  • the linker is an isophorone group.
  • isophorone means the following group:
  • the said reactive groups functionalizing the junction group must be capable of reacting with the -OH reactive group(s) borne by the functionalized polyalkene.
  • the functionalized junction groups capable of forming at least three H bonds may comprise at least three identical or different functional groups, and preferably at least four functional groups, chosen from:
  • junction groups capable of forming at least three H bonds form a basic structural element comprising at least three groups, preferably at least four groups and more preferentially four functional groups capable of establishing H bonds.
  • the said basic structural elements capable of establishing H bonds may be represented schematically in the following manner:
  • each structural element should be capable of establishing H bonds with one or more partner structural elements, which are identical (i.e. self-complementary) or different, such that each pairing of two partner structural elements takes place by formation of at least three H bonds, preferably at least four H bonds and more preferentially four H bonds.
  • a proton acceptor X will pair with a proton donor Y.
  • two donor bonds for example NH
  • junction groups capable of forming at least four H bonds are chosen from the following families, it being understood that all the tautomeric forms are included:
  • the radicals 3 ⁇ 4 are single bonds constituting the point of attachment of the junction group to the linker capable of forming at least three H bonds (preferably four H bonds) on the rest of the graft.
  • the said point of attachment is borne solely by R ls which is a single bond.
  • R 2 represents a divalent group chosen from a single bond or a Q-Q alkylene or a monovalent group chosen from a single bond, a hydrogen atom or a linear or branched - o saturated monovalent hydrocarbon-based group, which may contain one or more heteroatoms such as O, S or N, these groups being optionally substituted with a hydroxyl, amino and/or thio function.
  • the radical R 2 may be a single bond or a monovalent group chosen from H, CH 2 OH and (CH 2 )2-OH, CH 3 .
  • R 2 is H.
  • the radical R 3 represents a monovalent or divalent group, in particular, R 3 is chosen from a hydrogen atom or a linear or branched Q-Qo saturated monovalent hydrocarbon-based group, which may contain one or more heteroatoms such as O, S or N, these groups being optionally substituted with a hydroxyl, amino and/or thio function.
  • the radical R 3 may be a monovalent group chosen from H, CH 2 OH and (Cf ⁇ -OH, CH 3 .
  • R 3 is a methyl group.
  • the junction groups are chosen from 2-ureidopyrimidone and 6-methyl-2-ureidopyrimidone.
  • the preferred junction group is 6-methyl-2-ureidopyrimidone.
  • junction groups and especially the ureidopyrimidone junction groups, may be added directly or may be formed in situ during the process for preparing the supramolecular polymer.
  • the first and second preparation methods described below illustrate these two alternatives, respectively.
  • the functionalized junction groups capable of reacting with the functionalized polyalkene polymer to give the supramolecular polymer according to the invention are preferably of formula:
  • L is chosen from the groups:
  • alk l cycloalkylene alkylene, such as isophorone
  • - C!-C 20 alkylene such as -(CH 2 ) 2 -; -(CH 2 ) 6 -; -CH 2 CH(CH 3 )-CH 2 -C(CH 3 )2-CH 2 -CH 2 , and
  • L is chosen from: -isophorone- ; -(CH 2 ) 6 -; 4,4'-methylene biscyclohexylene.
  • the junction group is of formula
  • the supramolecular polymer of the invention corresponds to the formula:
  • L' and L" represent a saturated or unsaturated Ci-C 20 divalent carbon-based group, chosen in particular from a linear or branched Ci-C2 0 alkylene; a C 5 -C 20 (alkyl)cycloalkylene, an alkylene- biscycloalkylene and a C 6 -C 20 (alkyl)arylene.
  • L' and L" represent an -isophorone-; -(CH ⁇ - ; -(CH 2 ) 6 -; -CH 2 CH(CH 3 )-CH 2 -C(CH 3 )2-CH2-CH 2 ; 4,4'-methylene biscyclohexylene; 2-methyl-l,3- phenylene group.
  • L' and L" are identical.
  • L' and L" are an isophorone group.
  • P is hydrogenated and represents a polyethylene, a polybutylene, a polybutadiene, a polyisoprene, a poly(l,3-pentadiene), a polyisobutylene, or a copolymer thereof, especially a poly(ethylene/butylene).
  • P is a hydrogenated polybutadiene, preferably a hydrogenated 1 ,2-polybutadiene.
  • the supramolecular polymer of the invention corresponds to the formulf
  • n is preferably comprised between 2 and 200, preferably between 10 and 150, preferably between 15 and 100, and most preferably between 20 and 70.
  • the polymer according to the invention may be prepared via the processes usually used by a person skilled in the art, especially for forming a urethane bond between the free OH functions of a polyalkene, and the isocyanate functions borne by the junction group.
  • a first general preparation process consists in:
  • the polymer to be functionalized does not comprise any residual water, - heating the said polymer comprising at least two OH reactive functions to a temperature that may be between 60°C and 140°C; the hydroxyl number of the polymer being able to serve as reference in order to measure the degree of progress of the reaction;
  • the reaction may also be monitored by assaying the hydroxyl functions; it is also possible to add ethanol in order to ensure the total disappearance of the residual isocyanate functions.
  • the reaction may be performed in the presence of a solvent, especially methylteti ⁇ ydrofuran, tetrahydrofuran, toluene, propylene carbonate or butyl acetate. It is also possible to add a conventional catalyst for forming a urethane bond. An example that may be mentioned is dibutyltin dilaurate.
  • the polymer may finally be washed and dried, or even purified, according to the general knowledge of a person skilled in the art.
  • the reaction may comprise the following steps:
  • the diisocyanate may optionally be in excess relative to the polymer.
  • This first step may be performed in the presence of solvent, at a temperature of between 20°C and 100°C. This first step may be followed by a period of stirring under a controlled atmosphere for 1 to 24 hours. The mixture may optionally be heated. The degree of progress of this first step may be monitored by assaying the hydroxyl functions;
  • this second step may optionally be performed in the presence of a cosolvent such as toluene, butyl acetate or propylene carbonate.
  • a cosolvent such as toluene, butyl acetate or propylene carbonate.
  • the reaction mixture may be heated to between 80°C and 140°C for a time ranging between 1 and 24 hours.
  • the presence of a catalyst, especially dibutyltin dilaurate, may promote the production of the desired final product.
  • the reaction may be monitored by infrared spectroscopy, by monitoring the disappearance of the characteristic peak of isocyanate between 2200 and 2300 cm “1 .
  • ethanol may be added to the reaction medium in order to neutralize any residual isocyanate functions.
  • the reaction mixture may be optionally filtered.
  • the polymer may also be stripped directly in a cosmetic solvent.
  • the said supramolecular polymer is dissolved in a hydrocarbon- based oil, which is preferably volatile, in particular isododecane.
  • a hydrocarbon-based oil which is preferably volatile, in particular isododecane.
  • the composition of the invention will comprise at least one hydrocarbon-based oil, which is preferably volatile, in particular at least isododecane, especially provided by the supramolecular polymer solution.
  • composition for making up and/or caring for the lips may comprise at least 0,1 % by weight of at least one supramolecular polymer, preferably at least 1% by weight, relative to its total weight.
  • the supramolecular polymer(s) may be present in a composition according to the invention in an amount ranging from 0.1 % to 60% by weight of solids, relative to the total weight of the composition.
  • the supramolecular polymer(s) may be present in a composition according to the invention in an amount ranging from 1 % to 60% by weight, relative to the total weight of the composition.
  • the supramolecular polymer(s) may be present in a composition according to the invention in an amount ranging from 2,5% to 50% by weight, relative to the total weight of the composition.
  • the supramolecular polymer(s) may also be present in a composition according to the invention in an amount ranging from 4% to 40% by weight, relative to the total weight of the composition.
  • a composition according to the invention in particular in the case of a composition for making up the skin and/or the lips, comprises a content of supramolecular polymer of between 2,5% and 90% by weight relative to the weight of the composition excluding volatile compound(s) (in particular relative to the weight of the composition excluding volatile oil(s), for instance isododecane)
  • This content reflects the resulting content of supramolecular polymer(s) in a deposit made with a composition or according to the process of the invention, especially on keratin materials such as the skin and/or the lips, for example, after evaporation of the volatile compounds.
  • the composition according to the invention in particular in the case of a makeup composition, comprises a content of supramolecular polymer of between 3% and 80% by weight, preferably between 5% and 50% by weight, relative to the weight of the composition excluding volatile compound(s).
  • a content of supramolecular polymer of between 3% and 80% by weight, preferably between 5% and 50% by weight, relative to the weight of the composition excluding volatile compound(s).
  • composition according to the invention comprises at least one non volatile silicone oil.
  • oil means a water-immiscible non-aqueous compound that is liquid at room temperature (25°C) and at atmospheric pressure (760 mmHg).
  • silicone oils that may be used according to the invention are non-volatile.
  • non-volatile silicone oils that may be used in the invention preferably have a viscosity at 25°C comprised between 9cSt and 800 000 cSt, preferably less than or equal to 600 000 cSt and preferably less than or equal to 500 000 cSt.
  • the viscosity of these silicone oils may be measured according to standard ASTM D-445.
  • non-volatile oil means an oil whose vapour pressure at room temperature and atmospheric pressure is non-zero and less than 0.02 mmHg (2.66 Pa) and better still less than 10 "3 mmHg (0.13 Pa).
  • the non- volatile silicone oil that may be used in the invention may be chosen especially from silicone oils especially with a viscosity at 25°C of greater than or equal to 9 centistokes (cSt) (9 x lO ⁇ m s) and preferably less than 800 000 cSt, preferably between 50 and 600 000 cSt and preferably between 100 and 500 000 cSt.
  • the viscosity of this silicone oil may be measured according to standard ASTM D- 445.
  • silicone oils two types of oil may be distinguished, according to whether or not they contain phenyl.
  • the non-volatile silicone oil is a non-phenylated silicone oil.
  • non phenylated silicone oil or “non phenyl silicone oil” means a silicon oil having no phenyl substituent.
  • non-volatile non phenylated silicone oils include polydimethylsiloxanes; alkyl dimethicones; vinyl methyl methicones; and also silicones modified with optionally fluorinated aliphatic groups, or with functional groups such as hydroxyl, thiol and/or amine groups.
  • the non volatile silicon oil is a non phenylated oil, preferably chosen from polydimethylsiloxanes; alkyl dimethicones; vinyl methyl methicones; and also silicones modified with optionally fluorinated aliphatic groups, or with functional groups such as hydroxyl, thiol and/or amine groups.
  • the non volatile non phenylated silicon oil is preferably chosen from dimethicone oils, preferably chosen from polydimethylsiloxanes; alkyl dimethicones.
  • Non-phenylated non-volatile silicone oils can be chosen from:
  • alkyl or alkoxy groups which are pendent and/or at the end of the silicone chain, these groups each containing from 2 to 24 carbon atoms, such as cetyldimethicone sold under the commercial reference ABIL WAX 9801 from Evonik Goldschmidt,
  • - PDMSs comprising aliphatic and/or aromatic groups, or functional groups such as hydroxyl, thiol and/or amine groups,
  • polyalkylmethylsiloxanes such as cetyldimethicone sold under the commercial reference ABIL WAX 9801 from Evonik Goldschmidt, or polyalkylmethylsiloxane optionally substituted with a fluorinated group, such as polymemyltrifluoropropyldimethylsiloxanes,
  • a composition according to the invention contains at least one non- phenylated linear silicone oil.
  • non-volatile non phenylated linear silicone oils may be chosen from polydimethylsiloxanes; alkyl dimethicones; vinyl methyl methicones; and also silicones modified with optionally fluorinated aliphatic groups, or with functional groups such as hydroxyl, thiol and/or amine groups.
  • the non-phenylated linear silicone oil may be chosen especially from the silicones of formula (I):
  • R ls R 2 , R 5 and ⁇ are, together or separately, an alkyl radical containing 1 to 6 carbon atoms
  • R 3 and ; are, together or separately, an alkyl radical containing from 1 to 6 carbon atoms, a vinyl radical, an amine radical or a hydroxyl radical,
  • X is an alkyl radical containing from 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 whose viscosity at 25°C is between 9 centistokes (cSt) (9 x lOW/s) and 800 000 cSt.
  • non- volatile non phenylated silicone oils that may be used according to the invention, mention may be made of those for which:
  • the substituents Ri to 3 ⁇ 4 and X represent a methyl group
  • p and n are such that the viscosity is 500 000 cSt, such as the product sold under the name SE30 by the company General Electric, the product sold under the name AK 500000 by the company Wacker, the product sold under the name Mirasil DM 500 000 by the company Bluestar, and the product sold under the name Dow Corning 200 Fluid 500000 cSt by the company Dow Corning,
  • the substituents Ri to R and X represent a methyl group
  • p and n are such that the viscosity is 60 000 cSt, such as the product sold under the name Dow Corning 200 Fluid 60000 CS by the company Dow Corning, and the product sold under the name Wacker Belsil DM 60 000 by the company Wacker,
  • the substituents Ri to Re represent a methyl group
  • the group X represents a hydroxyl group
  • n and p are such that the viscosity is 700 cSt, such as the product sold under the name Baysilone Fluid T0.7 by the company Momentive.
  • the composition compositions comprises a polyalkylmethylsiloxanes, such as cetyldimethicone sold under the commercial reference ABIL WAX 9801 from Evonik Goldschmidt.
  • the composition comprises from 0,1 to 10% polyalkylmethylsiloxanes, such as cetyldimethicone.
  • a composition according to the invention contains at least one non-volatile phenylated silicone oil.
  • phenylated silicone oil or "phenyl silicone oil” means a silicone oil having at least one phenyl substituent.
  • the non volatile phenylated silicone oil may be chosen from :
  • the phenyl silicone oil comprises at least three phenyl groups, for example at least four, at least five or at least six. b) the phenyl silicone oils corresponding to the following formula ( ⁇ ):
  • the said organopolysiloxane comprises at least three phenyl groups, for example at least four or at least five.
  • Mixtures of the phenyl organopolysiloxanes described previously may be used. Examples that may be mentioned include mixtures of triphenyl, tetraphenyl or pentaphenyl organopolysiloxanes.
  • the phenyl silicone oils corresponding to the following formula (Tfl):
  • Such a phenyl silicone oil is preferably trimethyl pentaphenyl trisiloxane, or Tetramethyl Tetraphenyl Trisiloxane.
  • oils are especially manufactured by Dow Corning under the reference PH- 1555 HRI or Dow Corning 555 Cosmetic Fluid (chemical name: l,3,5-trimethyl-l,l,3,5,5-pentaphenyl trisiloxane; INCI name: trimethyl pentaphenyl trisiloxane), or Tetramethyl Tetraphenyl Trisiloxane sold under he reference Dow Corning 554 Cosmetic Fluid by Dow Corning may also be used.
  • the phenyl silicone oils corresponding to the following formula (TV):
  • y ranges between 1 and 1000.
  • Use may be made, for example, of trimethyl siloxyphenyl dimethicone, sold especially under the reference Belsil PDM 1000 sold by the company Wacker.
  • y is equal to 0.
  • Use may be made, for example, of phenyl trimethylsiloxy trisiloxane, sold especially under the reference Dow Corning 556 Cosmetic Grade Fluid (DC556), f) the phenyl silicone oils corresponding to formula (VI) below, and mixtures thereof:
  • R - R ⁇ to R 10 independently of each other, are saturated or unsaturated, linear, cyclic or branched Ci-C3 0 hydrocarbon-based radicals,
  • n, p and q are, independently of each other, integers between 0 and 900, with the proviso that the sum m+n+q is other than 0.
  • the sum m+n+q is between 1 and 100.
  • the sum m+n+p+q is between 1 and 900 and better still between 1 and 800.
  • q is equal to 0.
  • R 1 to R 10 independently of each other, represent a saturated or unsaturated linear or branched -C30, hydrocarbon radical, preferably saturated, and especially Ci-C 12 hydrocarbon-based radical, in particular C 3 -C 16 and more particularly C 4 -C 10 , or a monocyclic or polycyclic C 6 -C 14 and especially C 10 -C 13 aryl radical, or an aralkyl radical.
  • Ri to R 10 may each represent a methyl, ethyl, propyl, butyl, isopropyl, decyl, dodecyl or octadecyl radical, or alternatively a phenyl, tolyl, benzyl or phenethyl radical.
  • 3 ⁇ 4 to R 10 may especially be identical, and in addition may be a methyl radical thereof:
  • - Ri to Re independently of each other, are saturated or unsaturated, linear, cyclic or branched C1-C30 hydrocarbon-based radicals, preferably R ⁇ to Re are a -C30 alkyl radical, an aryl radical or an aralkyl radical
  • n and p are, independently of each other, integers between 0 and 100, with the proviso that the sum n+m is between 1 and 100.
  • Ri to Re independently of each other, represent a saturated or unsaturated linear or branched Q-C30, hydrocarbon radical, preferably saturated, and especially C1-C12 hydrocarbon-based radical, in particular C3-Q6 and more particularly C 4 -C 10 , or a monocyclic or polycyclic C 6 -C 14 and especially QO-C aryl radical, or an aralkyl radical.
  • Rl to R6 may each represent a methyl, ethyl, propyl, butyl, isopropyl, decyl, dodecyl or octadecyl radical, or alternatively a phenyl, tolyl, benzyl or phenethyl radical.
  • Ri to Re may especially be identical, and in addition may be a methyl radical.
  • m 1 or 2 or 3
  • h the phenyl silicone oils corresponding to the following formula, and mixtures thereof:
  • R 1; R 2 , R 5 and Re are, together or separately, an alkyl radical containing 1 to 6 carbon atoms,
  • R3 and R4 are, together or separately, an alkyl radical containing from 1 to 6 carbon atoms or an aryl radical, with the proviso that at least one from R3 and t is a phenyl radical, X is an alkyl radical containing from 1 to 6 carbon atoms, a hydroxyl radical or a vinyl radical,
  • n and p being integer superior or equal to 1, chosen so as to give the oil a weight- average molecular mass of less than 200000 g/mol, preferably less than 150000 g/mol and more preferably less than 100000 g mol. i) and mixture thereof.
  • silicone oils such as: - phenyl silicone oil, preferably chosen from : Tetramethyl Tetraphenyl Trisiloxane (such as as PH- 1554 HRI or Dow Corning 554 Cosmetic Fluid from Dow Corning), trimethylsiloxyphenyldimethicone (for instance Belsil PDM 1000 from the company Wacker (cf.
  • phenyl trimethicones such as the phenyl trimethicone sold under the trade name DC556 by Dow Corning
  • phenyl dimethicones such as the phenyl trimethicone sold under the trade name DC556 by Dow Corning
  • phenyl dimethicones such as the phenyl trimethicone sold under the trade name DC556 by Dow Corning
  • phenyl dimethicones such as the phenyl trimethicone sold under the trade name DC556 by Dow Corning
  • phenyl dimethicones such as the phenyl trimethicone sold under the trade name DC556 by Dow Corning
  • phenyl dimethicones such as the phenyl trimethicone sold under the trade name DC556 by Dow Corning
  • phenyl dimethicones such as the phenyl trimethicone sold under the trade name DC556 by Dow Corning
  • PDMS polydimethylsiloxanes
  • alkyl or alkoxy groups which are pendent and/or at the end of the silicone chain, these groups each containing from 2 to 24 carbon atoms
  • the phenyl silicones are more preferably chosen from :
  • phenyl silicones are chosen from :
  • the weight-average molecular weight of the non-volatile phenyl silicone oil according to the invention ranges from 500 to 10 000 g/mol.
  • Non Volatile Phenyl silicone oil having at least a dimethicone part is chosen from phenyl dimethicone oil(s), (which means a phenyl silicone oil having at least a dimethicone part).
  • n and p are independently of each other, integers between 1 and 100, in formula (VET).
  • Rl to R6 are methyl radicals.
  • the silicone oil is preferably chosen from diphenyl dimethicone such as KF-54 from Shin Etsu (400 cSt), KF54HV from Shin Etsu (5000 cSt), KF-50-300CS from Shin Etsu (300 cSt), KF-53 from Shin Etsu (175cSt), KF-50-100CS from Shin Etsu (100 cSt).
  • p is between 1 and 100 in formula (VET)
  • the sum n+m is between 1 and 100
  • n 0 , in formula (VH).
  • the silicon oil is a phenyl silicone oil having at least a dimethicone part, and is preferably chosen from :
  • diphenyl dimethicone such as KF-54 from Shin Etsu (400 cSt), KF54HV from Shin Etsu (5000 cSt), KF-50-300CS from Shin Etsu (300 cSt), KF-53 from Shin Etsu (175cSt), KF- 50-lOOCS from Shin Etsu (100 cSt);
  • trimethyl pentaphenyl trisiloxane such as PH-1555 HRI or Dow Corning 555 Cosmetic Fluid from Dow Corning,
  • the silicone oil is a phenyl silicone oil having no dimethicone part.
  • the non volatile phenylated silicone oil having no dimethicone part may be chosen from :
  • the phenyl silicone oil comprises at least three phenyl groups, for example at least four, at least five or at least six. b) the phenyl silicone oils corresponding to the following formula ( ⁇ ):
  • the groups R represent, independently of each other, a methyl or a phenyl, with the proviso that at least one group R represents a phenyl.
  • the said organopolysiloxane comprises at least three phenyl groups, for example at least four or at least five. Mixtures of the phenyl organopolysiloxanes described previously may be used. Examples that may be mentioned include mixtures of triphenyl, tetraphenyl or pentaphenyl organopolysiloxanes.
  • the phenyl silicone oils corresponding to the following formula ( ⁇ ):
  • phenyl silicone is especially manufactured by Dow Corning under the reference PH-1555 HRI or Dow Corning 555 Cosmetic Fluid (chemical name: l,3,5-trimethyl-l,l,3,5,5-pentaphenyl trisiloxane; INCI name: trimethyl pentaphenyl trisiloxane), or Tetramethyl Tetraphenyl Trisiloxane sold under the reference Dow Corning 554 Cosmetic Fluid by Dow Corning may also be used.
  • phenyl silicone oils corresponding to formula (V') below:
  • R independently of each other, are saturated or unsaturated, linear, cyclic or branched -C30 hydrocarbon-based radicals, preferably R is a -C30 alkyl radical, an aryl radical or an aralkyl radical,
  • n are, independently of each other, integers between 0 and 100, with the proviso that the sum n+m is between 1 and 100.
  • R independently of each other, represent a saturated or unsaturated linear or branched d- C 30 , hydrocarbon radical, preferably saturated, and especially Ci-C 12 hydrocarbon-based radical, in particular C 3 -C 16 and more particularly C 4 -C 10 , or a monocyclic or polycyclic C 6 -C 14 and especially C 1 0-C13 aryl radical, or an aralkyl radical.
  • R may each represent a methyl, ethyl, propyl, butyl, isopropyl, decyl, dodecyl or octadecyl radical, or alternatively a phenyl, tolyl, benzyl or phenethyl radical.
  • R may especially be identical, and in addition may be a methyl radical.
  • n is an integer between 0 and 100 and m is an integer between 1 and 100, with the proviso that the sum n+m is between 1 and 100, in formula (V S).
  • R is methyl radical.
  • a phenyl silicone oil of formula (Vni) with a viscosity at 25°C of between 5 and 1500 mm 2 /s (i.e. 5 to 1500 cSt), and preferably with a viscosity of between 5 and 1000 mm 2 /s (i.e. 5 to 1000 cSt) may be used.
  • the non volatile phenyl silicone oil is preferably chosen from phenyl trimethicones; such as DC556 from Dow Corning (22.5 cSt), the oil diphenylsiloxy phenyltrimethicone such as KF56 A from Shin Etsu, the oil Silbione 70663V30 from Rhone-Poulenc (28 cSt).
  • phenyl trimethicones such as DC556 from Dow Corning (22.5 cSt)
  • the oil diphenylsiloxy phenyltrimethicone such as KF56 A from Shin Etsu
  • the oil Silbione 70663V30 from Rhone-Poulenc (28 cSt).
  • the values in parentheses represent the viscosities at 25°C
  • non volatile phenylated silicone oil having no dimethicone part may be chosen from :
  • Tetramethyl Tetraphenyl Trisiloxane such as PH-1554 HRI or Dow Corning 554 Cosmetic Fluid from Dow Corning
  • diphenylsiloxy phenyltrimethicone such as KF56 A from Shin Etsu, the oil Silbione 70663V30 from Rhone-Poulenc ,
  • trimethyl pentaphenyl trisiloxane such as PH-1555 HRI or Dow Corning 555 Cosmetic Fluid from Dow Corning,
  • the composition according to the invention advantageously contains from 1% to 80% by weight, in particular from 2% to 70% by weight and preferably from 5% to 60% by weight in total of non volatile silicone oil(s), relative to the total weight of the composition.
  • the phenyl silicone oils prove to be particularly advantageous. They can especially impart a good level of gloss to the deposit on the skin or the lips made with the composition according to the invention, without generating any tack, and enable forming a non transfer deposit in association with the non volatile hydrocarbonated oil.
  • a composition according to the invention for caring for and/or making up the lips and more particularly of lipstick or lipgloss type may comprise from 1% to 80% by weight of non volatile silicone oil(s) according to the invention relative to the total weight of the composition.
  • a composition according to the invention for caring for and/or making up the lips and more particularly of lipstick or lipgloss type may comprise from 5% to 60% by weight of non volatile silicone oil(s) according to the invention relative to the total weight of the composition.
  • composition according to the invention for caring for and/or making up the lips and more particularly of lipstick or lipgloss type may comprise from 10% to 50% by weight of non volatile silicone oil(s) according to the invention relative to the total weight of the composition.
  • a lip makeup composition may comprise more than 10% by weight of silicone compound(s) according to the invention relative to the total weight of the composition.
  • composition according to the invention comprises at least one non volatile hydrocarbonated oil (also called “hydrocarbon-based” oil).
  • the said non-volatile hydrocarbon-based oil may be an apolar oil.
  • apolar oil means an oil whose solubility parameter at 25 °C, 5 a , is equal to 0 (J/cm 3 ) m .
  • the parameters 3 ⁇ 4, 3 ⁇ 4, ⁇ and 6 a are expressed in (J/cm 3 ) 1 ⁇ 2 .
  • hydrocarbon-based oil (or “hydrocarbonated oil”, or “hydrocarbon oil”) means an oil formed essentially from, or even constituted by, carbon and hydrogen atoms, and optionally oxygen and nitrogen atoms, and not containing any silicon or fluorine atoms. It may contain alcohol, ester, ether, carboxylic acid, amine and/or amide groups.
  • oils may be of plant, mineral or synthetic origin.
  • the non-volatile apolar hydrocarbon-based oil may be chosen from linear or branched hydrocarbons of mineral or synthetic origin.
  • said -volatile apolar hydrocarbon-based oil may be chosen from :
  • the composition according to the invention comprises at least one non volatile hydrocarbon-based apolar oil, preferably chosen from polybutenes, polyisobutenes, hydrogenated polyisobutenes, polydecenes and/or hydrogenated polydecenes, and mixtures thereof.
  • non volatile hydrocarbon-based apolar oil preferably chosen from polybutenes, polyisobutenes, hydrogenated polyisobutenes, polydecenes and/or hydrogenated polydecenes, and mixtures thereof.
  • a composition according to the invention may comprise a content of non volatile hydrocarbon oil ranging from 1% to 80%, for example from 2% to 70% by weight and preferably from 5% to 60% by weight, relative to the total weight of the composition.
  • said non volatile hydrocarbon oil comprise at least an apolar oil(s), preferably in a content ranging from 1 to 80%, preferably from 2 to 70% by weight, relative to the total weight of the composition.
  • said non volatile hydrocarbon oil comprise at least an apolar oil(s), preferably in a content ranging from 5 to 60%, preferably from 10 to 50% by weight, relative to the total weight of the composition.
  • said non volatile hydrocarbon-based oil may be a polar hydrocarbon-based oil.
  • polar oil means an oil whose solubility parameter at 25°C, 5 a , is other than 0 (J/cm 3 ) ⁇ .
  • oils may be of plant, mineral or synthetic origin.
  • hydrocarbon-based non-volatile polar oil may be chosen from the list of oils below, and mixtures thereof:
  • hydrocarbon-based plant oils such as liquid triglycerides of fatty acids containing from 4 to 10 carbon atoms, for instance heptanoic or octanoic acid triglycerides or jojoba oil;
  • - ester oils preferably chosen from: - fatty acid esters, in particular of 4 to 22 carbon atoms, and especially of octanoic acid, heptanoic acid, lanolic acid, oleic acid, lauric acid or stearic acid, for instance propylene glycol dioctanoate, propylene glycol monoisostearate or neopentyl glycol diheptanoate;
  • oils of formula RiCOC ⁇ in which R represents a linear or branched fatty acid residue comprising from 4 to 40 carbon atoms and R 2 represents a hydrocarbon-based chain, which is especially branched, containing from 4 to 40 carbon atoms, on condition that Ri + R 2 16, for instance purcellin oil (cetostearyl octanoate), isononyl isononanoate, C 12 to C 15 alkyl benzoate, 2- ethylhexyl palmitate, octyldodecyl neopentanoate, 2-octyldodecyl stearate, 2-octyldodecyl erucate, oleyl erucate, isostearyl isostearate, 2-octyldodecyl benzoate, alcohol or polyalcohol octanoates, decanoates or ricinoleates, isoprop
  • R 1 represents a diol dimer residue obtained by hydrogenation of dilinoleic diacid
  • R represents a hydrogenated dilinoleic diacid residue
  • h represents an integer ranging from 1 to 9
  • polyesters obtained by condensation of an unsaturated fatty acid dimer and/or trimer and of diol, such as those described in patent application FR O 853 634, in particular such as dilinoleic acid and 1,4- butanediol.
  • Viscoplast 14436H (INCI name: dilinoleic acid/butanediol copolymer), or copolymers of polyols and of diacid dimers, and esters thereof, such as Hailuscent ISDA; - fatty alcohols containing from 12 to 26 carbon atoms, which are preferably branched, for instance octyldodecanol, 2-butyloctanol, 2-hexyldecanol, 2-undecylpentadecanol and oleyl alcohol;
  • - 2-C22 higher fatty acids such as oleic acid, linoleic acid and linolenic acid, and mixtures thereof;
  • oils of plant origin such as sesame oil (820.6 g/mol);
  • dialkyl carbonates the two alkyl chains possibly being identical or different, such as dicaprylyl carbonate sold under the name Cetiol CC ® by Cognis; and
  • composition according to the invention comprises at least one non-volatile hydrocarbon oil chosen from :
  • vinylpyrrolidone copolymers preferably such as the vinylpyrrolidone/l-hexadecene copolymer
  • esters preferably with a total carbon number ranging from 35 to 70, preferably chosen from polyglyceryl-2 triisostearate, isosteaiyl lactate, octyl hydroxystearate, octyldodecyl hydroxystearate, diisostearyl malate, glyceryl stearate; diethylene glycol diisononanoate;
  • oils from plant origin preferably chosen from liquid triglycerides of fatty acids
  • pentaerythrityl tetraisononanoate
  • Rj represents a linear or branched fatty acid residue containing from 4 to 40 carbon atoms and R 2 represents a hydrocarbon-based chain mat is especially branched, containing from 4 to 40 carbon atoms, provided that R 1 + R 2 ⁇ 16;
  • said non volatile hydrocarbon oil comprise at least a polar oil(s), preferably in a content ranging from 1 to 80%, preferably from 2 to 70% by weight, relative to the total weight of the composition.
  • said non volatile hydrocarbon oil comprise at least a polar oil(s), preferably in a content ranging from 5 to 60%, preferably from 10 to 50% by weight, relative to the total weight of the composition.
  • the weight ratio of the total non volatile hydrocarbonated oil(s) to the total non volatile silicone oil(s) is comprised between 0,1 and 10, more preferably comprised between 0,1 and 5, and preferably comprised between 0,5 and 5.
  • the weight ratio of the total apolar non volatile hydrocarbonated oil(s) to the total non volatile silicone oil(s) is between 0,1 and 10, preferably between 0,1 and 5.
  • the weight ratio of the total apolar non volatile hydrocarbonated oil(s) to the total non volatile phenyl silicone oil(s) is between 0, 1 and 10, more preferably comprised between 0, 1 and 5.
  • a cosmetic makeup and/or care composition according to the invention also comprises a cosmetically acceptable medium that may comprise the usual ingredients, as a function of the intended use of the composition.
  • composition may also comprises at least one additional compound, preferably chosen from a hydrocarbonated polar oil, and/or a fatty pasty compound and/or a filler, and/or a colouring agent, and/or mixture thereof.
  • additional compound preferably chosen from a hydrocarbonated polar oil, and/or a fatty pasty compound and/or a filler, and/or a colouring agent, and/or mixture thereof.
  • the composition according to the invention may comprise, besides said non volatile silicone oil and said non volatile hydrocarbonated oil, an additional liquid fatty phase.
  • the additional liquid fatty phase may represent from 0.1% to 98% by weight relative to the total weight of the composition.
  • this weight percentage of liquid fatty phase takes into account the weight of oil used for the formulation of the associated supramolecular polymer, if present.
  • a composition according to the invention and/or used in a composition according to the invention may comprise from 0.1% to 95% by weight of an additional liquid fatty phase relative to its total weight. More particularly, a composition according to the invention and/or used in a composition according to the invention may comprise from 0.5% to 90% by weight of an additional liquid fatty phase relative to its total weight.
  • the composition according to the invention may comprise a volatile oil.
  • composition under consideration according to the invention may advantageously comprise one or more oils, which may be chosen especially from volatile hydrocarbon-based oils, volatile silicone oil and fluoro oils, and mixtures thereof.
  • volatile oil means an oil that is capable of evaporating on contact with keratin materials in less than one hour, at room temperature (25°C) and atmospheric pressure (760 mmHg).
  • the volatile oil is a volatile cosmetic oil, which is liquid at room temperature, especially having a non-zero vapour pressure, at room temperature and atmospheric pressure, in particular having a vapour pressure ranging from 0.13 Pa to 40 000 Pa (10 " to 300 mmHg), preferably ranging from 1.3 Pa to 13 000 Pa (0.01 to 100 mmHg) and preferentially ranging from 1.3 Pa to 1300 Pa (0.1 to 10 mmHg).
  • the oils may be of animal, plant, mineral or synthetic origin.
  • Volatile fluoro oil means an oil comprising at least one fluorine atom.
  • perfluoro compounds means compounds in which all the hydrogen atoms have been replaced with fluorine atoms.
  • the fluoro oil according to the invention is chosen from perfluoro oils.
  • perfluoro oils that may be used in the invention, mention may be made of perfluorodecalins and perfluoroperhydrophenanthrenes.
  • the fluoro oil is chosen from perfluoroperhydrophenanthrenes, and especially the Fiflow® products sold by the company Creations Couliv.
  • the fluoro oil whose INCI name is perfluoroperhydrophenanthrene, sold under the reference Fiflow 220 by the company F2 Chemicals.
  • the composition according to the invention further comprises a volatile hydrocarbonated oil such as isododecane and/or isohexadecane.
  • hydrocarbon-based oil means an oil formed essentially from, or even constituted by, carbon and hydrogen atoms, and optionally oxygen and nitrogen atoms, and not containing any silicon or fluorine atoms. It may contain alcohol, ester, ether, carboxylic acid, amine and or amide groups.
  • the volatile hydrocarbon-based oils may be chosen from hydrocarbon-based oils containing from 8 to 16 carbon atoms, and especially C 8 -C 16 branched alkanes (also known as isoparaffins), for instance isododecane (also called 2,2,4,4,6-pentamethylheptane), isodecane and isohexadecane, and mixture thereof.
  • the volatile hydrocarbon-based oil may also be a linear volatile alkane containing 7 to 17 carbon atoms, in particular 9 to 15 carbon atoms and more particularly 11 to 13 carbon atoms.
  • n-nonadecane Mention may be made especially of n-nonadecane, n-decane, n-undecane, n-dodecane, n-tridecane, n-tetradecane, n- pentadecane and n-hexadecane, and mixtures thereof.
  • hydrocarbon-based oil is intended to mean an oil formed essentially, or even constituted, of carbon and hydrogen atoms, and optionally of oxygen and nitrogen atoms, and containing no silicon or fluorine atoms. It may contain alcohol, ester, ether, carboxylic acid, amine and/or amide groups.
  • a composition according to the invention also comprises at least isododecane and/or isohexadecane.
  • the composition is free of additional volatile hydrocarbonated oil other than isododecane and/or isohexadecane.
  • composition according to the invention contains between 1% and 60% by weight of volatile oil, preferably isododecane and/or isohexadecane, relative to its total weight.
  • the composition according to the invention contains between 2% and 50% by weight of volatile oil, preferably of isododecane and/or isohexadecane, relative to its total weight.
  • the composition according to the invention contains between 5% and 40% by weight of volatile oil, preferably of isododecane and/or isohexadecane, relative to its total weight.
  • volatile hydrocarbon-based solvents oils
  • the volatile oil has a flash point of greater than 65°C, and better still greater than 80°C.
  • a flash point of greater than 65°C, and better still greater than 80°C.
  • the composition according to the invention comprises less than 5% and better still less than 2% by weight of volatile oil having a flash point of less than 80°C, relative to the total weight of the composition.
  • the composition according to the invention is free of volatile oil having a flash point of less than 80°C.
  • compositions according to the invention may comprise at least one volatile silicone oil.
  • silicone oil is intended to mean an oil comprising at least one silicon atom, and in particular comprising Si-0 groups.
  • volatile silicone oil that may be used in the invention may be chosen from silicone oils especially
  • cSt centistokes
  • silicon oil is intended to mean an oil comprising at least one silicon atom, and in particular comprising Si-0 groups.
  • the volatile silicone oil that can be used in the invention may be chosen from silicone oils having a flash point ranging from 40°C to 150°C, preferably having a flash point of greater than 55°C and less than or equal to 105°C, and preferentially ranging from 65°C to 95°C.
  • the flash point is in particular measured according to ISO standard 3679.
  • the volatile silicone oil may be chosen from linear or cyclic silicone oils such as linear or cyclic polydimethylsiloxanes (PDMSs) having from 3 to 7 silicon atoms.
  • Volatile silicone oils that may more particularly be mentioned include decamethylcyclopentasiloxane sold especially under the name DC-245 by the company Dow Corning, dodecamethylcyclohexasiloxane sold especially under the name DC-246 by the company Dow Corning, octamethyltrisiloxane sold especially under the name DC-200 Fluid 1 cSt by the company Dow Corning, polydimethylsiloxanes such as decamethyltetrasiloxane sold especially under the name DC-200 Fluid 1.5 cSt by the company Dow Corning and DC-200 Fluid 5 cSt sold by the company Dow Corning, octamethylcyclotetrasiloxane, heptamethylhexyltrisiloxane, heptamethylethyltrisiloxan
  • a composition according to the invention may preferably also comprise at least one solid fatty substance especially chosen from waxes and/or pasty fatty substances.
  • the composition is free of wax or contains less than 5% by weight of waxes, preferably less than 3%, relative to the total weight of the composition.
  • the composition is liquid at room temperature.
  • the composition can be a lipgloss.
  • the composition comprises at least one wax.
  • the amount of wax(es) in the makeup and/or care composition according to the invention is between 0.5% and 30% by weight, especially from 1% to 20% by weight or even 2% to 15% by weight, relative to the total weight of the composition.
  • the presence of waxes is preferred when the composition according to the invention is solid at room temperature.
  • the composition can be a lipsticks.
  • the term "wax" means a lipophilic compound that is solid at room temperature (25°C), with a reversible solid/liquid change of state, having a melting point of greater than or equal to 30°C, which may be up to 200°C.
  • the waxes may be chosen from waxes of animal, plant, mineral or synthetic origin, and mixtures thereof. Mention may be made especially of hydrocarbon-based waxes, for instance beeswax, lanolin wax and Chinese insect waxes; rice bran wax, carnauba wax, candelilla wax, ouricury wax, alfalfa wax, berry wax, shellac wax, Japan wax and sumach wax; montan wax, orange wax, lemon wax, microcrystalline waxes, paraffins and ozokerite; polyethylene waxes, the waxes obtained by Fisher-Tropsch synthesis and waxy copolymers, and also esters thereof.
  • hydrocarbon-based waxes for instance beeswax, lanolin wax and Chinese insect waxes
  • montan wax orange wax, lemon wax, microcrystalline waxe
  • waxes obtained by catalytic hydrogenation of animal or plant oils containing linear or branched Q-C32 fatty chains may also be made especially of hydrogenated sunflower oil, hydrogenated castor oil, hydrogenated coconut oil, hydrogenated lanolin oil and bis(l,l,l-trimethylolpropane) tetrastearate.
  • Mention may also be made of silicone waxes and fluoro waxes.
  • the waxes obtained by hydrogenation of castor oil esterified with cetyl alcohol may also be used.
  • a composition according to the invention may comprise at least one wax, especially a hydrocarbon-based wax.
  • the composition is free of pasty fatty substances.
  • the composition comprises at least one pasty fatty substance.
  • the amount of pasty fatty substance in the makeup and/or care composition according to the invention is between 0.5% and 60% by weight, especially from 1% to 50% by weight or even 2% to 40% by weight, relative to the total weight of the composition.
  • pasty within the meaning of the present invention, is understood to mean a lipophilic fatty compound with a reversible solid/liquid change of state exhibiting, in the solid state, an anisotropic crystalline arrangement and comprising, at a temperature of 23 °C, a liquid fraction and a solid fraction.
  • the term "pasty compound”, within the meaning of the invention, is understood to mean a compound having a hardness at 20°C ranging from 0.001 to 0.5 MPa, preferably from 0.002 to 0.4 MPa.
  • the hardness is measured according to a method of penetration of a probe into a sample of compound and in particular using a texture analyser (for example, the ⁇ - ⁇ 2 ⁇ from Rheo) equipped with a stainless steel cylinder with a diameter of 2 mm.
  • the hardness measurement is carried out at 20°C at the centre of 5 samples.
  • the cylinder is introduced into each sample at a pre-rate of 1 mm/s and then at a measuring rate of 0.1 mm/s, the depth of penetration being 0.3 mm.
  • this pasty compound is, at a temperature of 23 °C, in the form of a liquid fraction and of a solid fraction. In other words, the starting melting temperature of the pasty compound is less than 23 °C.
  • the liquid fraction of the pasty compound, measured at 23 °C, represents 9 to 97% by weight of the compound. This liquid fraction at 23 °C preferably represents between 15 and 85%, more preferably between 40 and 85%, by weight.
  • the liquid fraction by weight of the pasty compound at 23°C is equal to the ratio of the enthalpy of fusion consumed at 23°C to the enthalpy of fusion of the pasty compound.
  • the enthalpy of fusion of the pasty compound is the enthalpy consumed by the compound to change from the solid state to the liquid state.
  • the pasty compound is "in the solid state” when the whole of its mass is in the crystalline solid form.
  • the pasty compound is "in the liquid state” when the whole of its mass is in the liquid form.
  • the enthalpy of fusion of the pasty compound is equal to the area under the curve of the thermogram obtained using a differential scanning calorimeter (DSC), such as the calorimeter sold under the name MDSC 2920 by TA Instrument, with a rise in temperature of 5 or 10°C per minute, according to the ISO Standard 11357-3: 1999.
  • DSC differential scanning calorimeter
  • the enthalpy of fusion of the pasty compound is the amount of energy necessary to change the compound 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 to change from the solid state to the state which it exhibits at 23°C, composed of a liquid fraction and of a solid fraction.
  • the liquid fraction of the pasty compound measured at 32°C preferably represents from 30 to 100% by weight of the compound, preferably from 80 to 100%, more preferably from 90 to 100%, by weight of the compound.
  • the temperature of 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 compound is preferably chosen from synthetic compounds and compounds of plant origin.
  • a pasty compound may be obtained by synthesis from starting materials of plant origin. Mention may be made especially, alone or as a mixture, of:
  • lanolin - lanolin, and derivatives thereof, such as lanolin alcohol, oxyethylenated lanolins, acetylated lanolin, lanolin esters such as isopropyl lanolate, and oxypropylenated lanolins, petroleum jelly, in particular the product whose INCI name is petrolatum and which is sold under the name Ultima White PET USP by the company Penreco,
  • polyol ethers chosen from polyalkylene glycol pentaeiythrityl ethers, fatty alcohol ethers of sugars, and mixtures thereof, polyethylene glycol pentaerythrityl ether comprising five oxyethylene (5 OE) units (CTFA name: PEG-5 Pentaerythrityl Ether), polypropylene glycol pentaerythrityl ether comprising five oxypropylene (5 OP) units (CTFA name: PEG-5 Pentaerythrityl Ether) and mixtures thereof, and more especially the mixture PEG-5 Pentaerythrityl Ether, PPG-5 Pentaerythrityl Ether and soybean oil, sold under the name Lanolide by the company Vevy, which is a mixture in which the constituents are in a 46/46/8 weight ratio: 46% PEG-5 Pentaerythrityl Ether, 46% PPG-5 Pentaerythrityl Ether and 8% soybean oil;
  • esters ie pasty fatty substance comprising at least one ester function
  • liposoluble polyethers that are particularly preferred are copolymers of ethylene oxide and/or of propylene oxide with C 6 -C 30 long-chain alkylene oxides, more preferably such that the weight ratio of the ethylene oxide and/or of the propylene oxide to the alkylene oxides in the copolymer is from 5:95 to 70:30.
  • the pasty fatty substance comprises at least one ester function.
  • ester pasty fatty substances 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, preferably such as bis-diglyceryl polyacyladipate-2 sold under the brand name Softisan 649 by the company Sasol,
  • fatty acid triglycerides and derivatives thereof for instance triglycerides of fatty acids, which are especially Qo- s, and partially or totally hydrogenated such as those sold under the reference Softisan 100 by the company Sasol,
  • the aliphatic carboxylic acid comprises from 4 to 30 and preferably from 8 to 30 carbon atoms.
  • the aliphatic carboxylic acid is preferably branched.
  • the aliphatic hydroxycarboxylic acid ester is advantageously derived from a hydroxylated aliphatic carboxylic acid containing from 2 to 40 carbon atoms, preferably from 10 to 34 carbon atoms and better still from 12 to 28 carbon atoms, and from 1 to 20 hydroxyl groups, preferably from 1 to 10 hydroxyl groups and better still from 1 to 6 hydroxyl groups.
  • the aliphatic hydroxycarboxylic acid ester is chosen from:
  • esters of a diol dimer and of a diacid dimer where appropriate esterified on their free alcohol or acid function(s) with acid or alcohol radicals, especially dimer dilinoleate esters; such esters may be chosen especially from the esters having the following INCI nomenclature: bis- behenyl/isostearyl/phytosteryl dimer dilinoleyl dimer dilinoleate (commercialised under the references Plandool G and Plandool G7), phytosteryl/isostearyl/stearyVbehenyl dimer dilinoleate (Plandool H or Plandool S), and mixtures thereof,
  • hydrogenated oils of plant origin such as hydrogenated castor oil isostearate (sold as (SALACOS HCIS (V-L) Big par NISSFflN OIL), hydrogenated soybean oil, hydrogenated coconut oil, hydrogenated rape seed oil, mixtures of hydrogenated plant oils such as the mixture of hydrogenated soybean, coconut, palm and rape seed plant oil, for example the mixture sold under the reference Akogel® by the company Aarhuskarlshamn (TNCI name: Hydrogenated Vegetable Oil).
  • rosinate esters such as dilinoleyl dimers of hydrogenated rosinate (Lusplan DD-DHR or DD-DHR from Nippon Fine Chemical);
  • the pasty fatty substance is a hydrocarbon-based compound comprising at least one ester function.
  • the pasty fatty substance is chosen from hydrogenated castor oil isostearate (SALACOS HCIS (V-L) Big par NISSKN OIL), bis-behenyl/isostearyl/phytosteryl dimer dilinoleyl dimer dilinoleate, bis-diglyceryl polyacyladipate-2, hydrogenated castor oil dimer dilinoleate (Risocast-DA- L®, Risocast DA-H®, sold by Kokyu Alcohol Kogyo), polyvinyl laurate, mango butter, shea butter, hydrogenated soybean oil, hydrogenated coconut oil and hydrogenated rape seed oil, and mixtures thereof.
  • SALACOS HCIS V-L
  • NISSKN OIL hydrogenated castor oil isostearate
  • a makeup and/or care composition according to the invention may also comprise one or more filler(s). According to a first embodiment, the composition is free of fillers.
  • the composition comprises at least one or more filler(s).
  • fillers should be understood as meaning colorless or white, mineral or synthetic particles of any shape, which are insoluble in the medium of the composition, irrespective of the temperature at which the composition is manufactured. These fillers serve especially to modify the rheology or the texture of the composition.
  • the fillers may be mineral or organic and of any shape, platelet-shaped, spherical or oblong, irrespective of the crystallographic form (for example lamellar, cubic, hexagonal, orthorhombic, etc.). Mention may be made of talc, mica, silica, kaolin, clay, bentone, fumed silica particles, optionally hydrophilic- or hydrophobic-treated, polyamide (Nylon®) powder (Orgasol® from Atochem), poly- ⁇ - alanine powder and polyethylene powder, tetrafluoroethylene polymer (Teflon®) powder, lauroyllysine, starch, boron nitride, hollow polymer microspheres such as polyvinylidene chloride/acrylonitrile microspheres, for instance Expancel® (Nobel Industrie), acrylic acid copolymer microspheres (Polytrap® from the company Dow Corning) and silicone resin microbeads (for example Tospearls® from Toshiba
  • They may also be particles comprising a copolymer, said copolymer comprising trimethylol hexyl lactone.
  • it may be a copolymer of hexamethylene diisocyanate/trimethylol hexyl lactone.
  • Such particles are especially commercially available, for example, under the name Plastic Powder D- 400® or Plastic Powder D-800® from the company Toshiki.
  • the composition according to the invention comprises at least silica, preferably hydrophobic treated silica.
  • the composition comprises at least one filler, and in particular chosen from fumed silicas that have optionally been hydrophilic- or hydrophobic-treated, preferably hydrophobic-treated.
  • the composition comprises at least one JSller known as Silica Dimethyl Silylate (according to the CTFA).
  • the hydrophobic groups may especially be dimethylsilyloxyl or polydimethylsiloxane groups, which are especially obtained 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® and Cab-O-Sil TS-720® by the company Cabot.
  • the composition according to the invention is free of "nanosilica", preferably free of hydrophobic treated silica of INCI name Silica Dimethyl Silylate.
  • nanonosilica means silica having a nanometric size, or a least a fraction of nanometric size.
  • the composition contains between 0.01% and 25% by weight and in particular between 0.1% and 20% by weight of fillers relative to the total weight of the composition.
  • the composition when in liquid form, it comprises at least one filler, preferably chosen from silica, kaolin, bentone, fumed silica particles, which have preferably been hydrophobic-treated, lauroyllysine and starch.
  • filler preferably chosen from silica, kaolin, bentone, fumed silica particles, which have preferably been hydrophobic-treated, lauroyllysine and starch.
  • composition according to the invention may comprise a filler chosen from:
  • organomodified clays which are preferably clays treated with compounds chosen especially from quaternary amines and tertiary amines.
  • Organomodified clays that may be mentioned include organomodified bentonites, such as the product sold under the name Bentone 34 by the company Rheox, and organomodified hectorites such as the products sold under the names Bentone 27 and Bentone 38 by the company Rheox,
  • Such silicas are sold, for example, under the references Aerosil R812® by the company Degussa and Cab-O-Sil TS-530® by the company Cabot, and under the references Aerosil R972® and Aerosil R974® by the company Degussa and Cab-O-Sil TS-610® and Cab-O-Sil TS-720® by the company Cabot.
  • the filler may be present in a content ranging from 0.1% to 5% by weight and better still from 0.4% to 3% by weight relative to the total weight of the composition.
  • the composition comprise may comprised at least hydrophobic silica aerogel particles .
  • Such compound is a filler.
  • such compound is present when the composition is free of nanosilica and more particularly free of Silica Dimethyl Silylate.
  • the hydrophobic silica aerogel particles may be present in a content ranging from 0.1% to 15% by weight and better still from 0.1% to 10% by weight, relative to the total weight of the composition.
  • the hydrophobic silica aerogel particles may be present in a content ranging from 0.1% to 6% by weight and better still from 0.2% to 4% by weight, relative to the total weight of the composition.
  • the composition may comprise at least a additional filler, such as those described before for example.
  • the composition according to the invention comprises at least Hydrophobic silica aerogel particles, when the composition is free of nanometric silica particules as described before, such as Silica Dimethyl Silylate.
  • Silica aerogels are porous materials obtained by replacing (by drying) the liquid component of a silica gel with air.
  • sol-gel processes are generally synthesized via a sol-gel process in liquid medium and then dried, usually by extraction of a supercritical fluid, the one most commonly used being supercritical C0 2 . This type of drying makes it possible to avoid shrinkage of the pores and of the material.
  • the sol-gel process and the various drying processes are described in detail in Blinker CJ., and Scherer G.W., Sol-Gel Science: New York: Academic Press, 1990.
  • the hydrophobic silica aerogel particles that may be used in the present invention have a specific surface area per unit of mass (SM) ranging from 500 to 1500 m /g, preferably from 600 to 1200 m /g and better still from 600 to 800 m /g, and a size expressed as the mean volume diameter (D[0.5]), ranging from 1 to 1500 ⁇ , better still from 1 to 1000 ⁇ , preferably from 1 to 100 ⁇ , in particular from 1 to 30 ⁇ , more preferably from 5 to 25 ⁇ , better still from 5 to 20 ⁇ and even better still & ⁇ 5 ⁇ 15 ⁇ .
  • SM surface area per unit of mass
  • the hydrophobic silica aerogel particles that may be used in the present invention have a size expressed as the mean volume diameter (D[0.5]) ranging from 1 to 30 ⁇ , preferably from 5 to 25 ⁇ , better still from 5 to 20 ⁇ and even better still from 5 to 15 ⁇ .
  • the specific surface area per unit of mass may be determined via the BET (Brunauer-Emmett-Teller) nitrogen absorption method described in the Journal of the American Chemical Society, vol. 60, page 309, February 1938 and corresponding to the international standard ISO 5794/1 (appendix D).
  • the BET specific surface area corresponds to the total specific surface area of the particles under consideration.
  • the size of the hydrophobic silica aerogel particles may be measured by static light scattering using a commercial granulometer such as the MasterSizer 2000 machine from Malvern.
  • the data are processed on the basis of the Mie scattering theory.
  • This theory which is exact for isotropic particles, makes it possible to determine, in the case of non-spherical particles, an "effective" particle diameter. This theory is especially described in the publication by Van de Hulst, H.C., "Light Scattering by Small Particles," Chapters 9 and 10, Wiley, New York, 1957.
  • the hydrophobic silica aerogel particles used in the present invention have a specific surface area per unit of mass (SM) ranging from 600 to 800 m 2 /g and a size expressed as the mean volume diameter (D[0.5]) ranging from 5 to 20 um and better still from 5 to 15 ⁇ .
  • SM surface area per unit of mass
  • D[0.5] mean volume diameter
  • the hydrophobic silica aerogel particles used in the present invention may advantageously have a tamped density p ranging from 0.04 g/cm to 0.10 g/cm and preferably from 0.05 g/cm to 0.08 g/cm .
  • this density known as the tamped density, may be assessed according to the following protocol:
  • the hydrophobic silica aerogel particles that may be used in the present invention have a specific surface area per unit of volume Sv ranging from 5 to 60 m /cm , preferably from 10 to 50 m /cm and better still from 15 to 40 m /cm .
  • the hydrophobic silica aerogel particles according to the invention have an oil-absorbing capacity, measured at the wet point, ranging from 5 to 18 ml/g, preferably from 6 to 15 ml/g and better still from 8 to 12 ml/g.
  • the oil-absorbing capacity measured at the wet point, noted Wp corresponds to the amount of water that needs to be added to 100 g of particle in order to obtain a homogeneous paste.
  • the oil uptake corresponds to the ratio Vs/m.
  • hydrophobic silica aerogel particles that may be used according to the present invention are preferably of silylated silica type (TNCI name: silica silylate).
  • TNCI name silica silylate.
  • hydrophobic silica means any silica whose surface is treated with silylating agents, for example halogenated silanes such as alkylchlorosilanes, siloxanes, in particular dimethylsiloxanes such as hexamethyldisiloxane, or silazanes, so as to functionalize the OH groups with silyl groups Si-Rn, for example trimethylsilyl groups.
  • silylating agents for example halogenated silanes such as alkylchlorosilanes, siloxanes, in particular dimethylsiloxanes such as hexamethyldisiloxane, or silazanes, so as to functionalize the OH groups with silyl groups Si-Rn, for example trimethylsilyl groups
  • hydrophobic silica aerogels particles surface-modified with trimethylsilyl groups Use will be made in particular of hydrophobic silica aerogels particles surface-modified with trimethylsilyl groups.
  • hydrophobic silica aerogel particles that may be used in the invention, examples that may be mentioned include the aerogel sold under the name VM-2260 (TNCI name: Silica silylate), by the company Dow Corning, the particles of which have a mean size of about 1000 microns and a specific surface area per unit of mass ranging from 600 to 800 m 2 /g.
  • VM-2260 TNCI name: Silica silylate
  • Dow Corning the particles of which have a mean size of about 1000 microns and a specific surface area per unit of mass ranging from 600 to 800 m 2 /g.
  • Aerogel TLD 201 Mention may also be made of the aerogels sold by the company Cabot under the references Aerogel TLD 201, Aerogel OGD 201, Aerogel TLD 203, and ENOVA AEROGEL MT 1100.
  • aerogel sold under the name VM-2270 (TNCI name: Silica silylate), by the company Dow Corning, the particles of which have a mean size ranging from 5-15 microns and a specific surface area per unit of mass ranging from 600 to 800 m 2 /g (oil uptake equal to 1080 ml/100 g).
  • VM-2270 TNCI name: Silica silylate
  • Dow Corning the particles of which have a mean size ranging from 5-15 microns and a specific surface area per unit of mass ranging from 600 to 800 m 2 /g (oil uptake equal to 1080 ml/100 g).
  • the hollow particles in accordance with the invention are at least partly formed from hydrophobic silica aerogel particles, preferably those with a specific surface area per unit of
  • SM mass
  • D[0.5] mean volume diameter
  • composition according to the invention may comprise at least an ester of dextrin, preferably an ester of dextrin and a fatty acid, preferably a C 12 a C 24 .fatty acid.
  • the dextrin ester is an ester of dextrine and a C 14 -C 18 fatty acid.
  • the dextrin ester is dextrine palmitate, for example such as those commercialised under the references Rheopearl TL ® or Rheopearl KL ® by the society CHIBA FLOUR.
  • a composition according to the invention may comprise a content of dextrin ester ranging from 0, 1% to 15% by weight and preferably from 0, 5% to 10% by weight, relative to the total weight of the composition.
  • a composition according to the invention may comprise a content of dextrin ester ranging from 1% to 8% by weight and preferably from 2% to 6% by weight, relative to the total weight of the composition.
  • the composition according to the invention is free from dextrin ester.
  • compositions according to the invention may preferably comprise at least one dyestuff (also known as a colouring agent), which may be chosen from water-soluble or liposoluble dyes, pigments and nacres, and mixtures thereof.
  • dyestuff also known as a colouring agent
  • composition according to the invention may also comprise one or more dyestuffs chosen from water-soluble dyes and pulverulent dyestuffs, for instance pigments, nacres and glitter flakes that are well known to those skilled in the art.
  • dyestuffs chosen from water-soluble dyes and pulverulent dyestuffs, for instance pigments, nacres and glitter flakes that are well known to those skilled in the art.
  • the dyestuffs may be present in the composition in a content ranging from 0.01% to 30% by weight, relative to the weight of the composition, preferably from 0.1% to 20% by weight.
  • pigments should be understood as meaning white or coloured, mineral or organic particles that are insoluble in an aqueous solution, which are intended to colour and/or opacify the resulting film.
  • the pigments may be present in a proportion of from 0.01% to 30% by weight, especially from 0.1 % to 25% by weight and in particular from 0.2% to 15% 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.
  • the dyestuff may also comprise a pigment 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.
  • An example of 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.
  • organic pigments that may be used in the invention, mention may be made of carbon black, pigments of D&C type, lakes based on cochineal carmine or on barium, strontium, calcium or aluminium, or alternatively the diketopyrrolopyrroles (DPP) described in documents EP-A-542 669, EP-A-787730, EP-A-787731 and WO-A-96/08537.
  • DPP diketopyrrolopyrroles
  • nacres should be understood as meaning coloured particles of any form, which may or may not be iridescent, especially produced by certain molluscs in their shell, or alternatively synthesized, and which have a colour effect via 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. Examples of nacres that may also be mentioned include natural mica coated with titanium oxide, with iron oxide, with natural pigment or with bismuth oxychloride.
  • nacres available on the market, mention may be made of the nacres Timica, Flamenco and Duochrome (based on mica) sold by the company Engelhard, the Timiron nacres sold by the company Merck, the Prestige mica-based nacres, sold by the company Eckart, and the Sunshine synthetic mica- based nacres, 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 tint.
  • nacres that may be used in the context of the present invention, mention may be made especially of the gold-coloured nacres sold especially by the company Engelhard under the name Brilliant gold 212G (Timica), Gold 222C (Cloisonne), Sparkle gold (Timica), Gold 4504 (Chromalite) and Monarch gold 233X (Cloisonne); the bronze nacres sold especially by the company Merck under the name Bronze fine (17384) (Colorona) and Bronze (17353) (Colorona) and by the company Engelhard under the name Super bronze (Cloisonne); the orange nacres sold especially by the company Engelhard under the name Orange 363C (Cloisonne) and Orange MCR 101 (Cosmica) and by the company Merck under the name Passion orange (Colorona) and Matte orange (17449) (Microna); the brown nacres sold especially by the company Engelhard under the name Nu-antique copper 340XB (Cloisonne) and Brown CL4509 (Chromalite); the n
  • the term "dyes” should be understood as meaning compounds that are generally organic, which are soluble in fatty substances such as oils or in an aqueous-alcoholic phase.
  • the cosmetic composition according to the invention may also comprise water-soluble or liposoluble dyes.
  • the liposoluble dyes are, for example, Sudan red, DC Red 17, DC Green 6, ⁇ -carotene, Sudan brown, DC Yellow 11, DC Violet 2, DC Orange 5 and quinoline yellow.
  • the water-soluble dyes are, for example, beetroot juice or methylene blue.
  • the cosmetic composition according to the invention may also contain at least one material with a specific optical effect as dyestuff.
  • 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 tint, goniochromatic coloring 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 afford the simultaneous manifestation of two effects, or even of a novel effect in accordance with the invention.
  • a composition according to the invention may also comprise an aqueous phase, which may represent 1% to 80% by weight, especially 2% to 70% by weight or even 3% to 60% by weight relative to the total weight of the composition.
  • This aqueous phase may be formed essentially from water, or may comprise a mixture of water and of water-miscible solvent (miscibility in water of greater than 50% by weight at 25°C) chosen especially from monoalcohols containing 1 to 5 carbon atoms such as ethanol, isopropanol, glycols containing 2 to 8 carbon atoms such as propylene glycol, ethylene glycol, 1,3- butylene glycol, dipropylene glycol, C 3 -C 4 ketones and C 2 -C 4 aldehydes, and mixtures thereof.
  • compositions according to the invention are anhydrous.
  • anhydrous especially means that water is preferably not deliberately added to the compositions, but may be present in trace amounts in the various compounds used in the compositions.
  • a makeup and/or care composition according to the invention may also comprise at least one agent usually used in cosmetics, chosen, for example, from reducing agents, thickeners, film-fonning agents that are especially hydrophobic, silicone elastomers, softeners, antifoams, moisturizers, UV-screening agents, ceramides; cosmetic active agents; peptizers, fragrances, proteins, vitamins, propellants, hydrophilic or lipophilic, film-forming or non-film-forrning polymers; lipophilic or hydrophilic gelling agents.
  • the above additives are generally present in an amount for each of them of between 0.01 % and 10% by weight relative to the total weight of the composition. Needless to say, a person skilled in the art will take care to select the constituents of the composition such that the advantageous properties associated with the invention are not, or are not substantially, adversely affected.
  • a composition used according to the invention may also comprise any usual cosmetic ingredient, which may be chosen especially from antioxidants, film-forming polymers, fragrances, preserving agents, emollients, moisturizers, neutralizers, sunscreens, sweeteners, vitamins, free-radical scavengers and sequestrants, and mixtures thereof.
  • the amounts of each of these various ingredients are those conventionally used in the fields under consideration, and range, for example, from 0.01% to 10% by weight relative to the total weight of the composition.
  • composition in accordance with the invention may be in liquid form or in solid form.
  • the composition is in solid form.
  • it may be a cosmetic product chosen from a lip balm and/or a lipstick.
  • This product may preferably be in the form of a stick or cast in a dish.
  • it is a lipstick or a lip balm in stick form.
  • a composition according to the invention may constitute a liquid lipstick for the lips, a body makeup product, a facial or body care product or an antisun product.
  • a composition of the invention is in liquid form.
  • the composition according to the invention is homogeneous and stable and gives access to a deposit on the skin or the lips that has good cosmetic properties, in particular in terms of gloss, comfort (thickness deposit) and absence of transfer of the deposit.
  • compositions according to the invention enable forming a deposit exhibits no color transfer, in particular on a cup while drinking for a lip product, and when the composition contains one or more colouring agent(s).
  • the temperature of the mixture is reduced to 20 °C, under argon, followed by addition of 30 ml of isododecane and 11 g of isophorone diisocyanate (IPDi).
  • IPDi isophorone diisocyanate
  • the temperature of the rnixture is reduced to 20°C, under argon, followed by addition of 60 ml of isododecane and 11.6 g of 4,4'-dicyclohexylmethane diisocyanate.
  • the rnixture is stirred for 16 hours at 20 °C under a controlled atmosphere, and is then heated to 120 °C, followed by addition of 40 ml of propylene carbonate. 6.64 g of 6-methylisocytosine are added, resulting in a homogeneous white suspension. This suspension is heated to 140 °C and stirred at this temperature for 8 hours. The reaction is monitored by infrared spectroscopy, up to the total disappearance of the characteristic peak for isocyanates (2250 cm "1 ). The mixture is then cooled to 30°C, and 250 ml of isododecane and 500 ml of heptane are added, followed by filtration through Celite. The mixture is then stripped with isododecane.
  • the fillers and pigments were ground in a three-roll mill in part of the oily phase (in diisostearyl malate).
  • the supramolecular polymer according to the invention was mixed with the silicone oil and the ground pigmentary material in a beaker or heating pan.
  • the mixture was stirred in a Rayneri blender until homogeneous.
  • the ground pigmentary material was then incorporated into the mixture and stirring was continued until the mixture was homogeneous.
  • the composition was left for 24 hours at room temperature before being conditioned in heating bags.
  • Formula 1 and formula 2 form homogenous and stable compositions after 24 hours at room temperature, and after 72 hours at room temperature, as well as after 72 hours at 42°C. In particular, there is no phase separation, and no sedimentation. Evaluation of the compositions
  • compositions 1 and 2 at 25°C The viscosity of compositions 1 and 2 at 25°C was measured according to the protocol described previously.
  • the shine of the deposit obtained on the lips with the compositions was evaluated using a Polka SEI- M-0216-Polk-02 polarimetric camera and a Chromasphere SEI-M-02232-CHRO-0 as described in patent application FR 2 829 344.
  • Color transfer resistance The color transfer resistance is evaluated by applying the lips on a white cup as while drinking 5 minutes after applying the compositions on the lips
  • Tackiness The tacky nature of a deposit made on the lips with the formula to be evaluated was evaluated 5 minutes after application by rubbing the upper and the lower lips together and the tack was assessed by the person on removal of her upper and lower lips.
  • compositions in accordance with the invention allow the production of a glossy and sparingly or not tacky makeup deposit on the lips. Both compositions 1 and 2 are easy to apply (good glide) homogenous deposits. The deposits formed with compositions according to the invention also good color transfer-resistance properties, as well as a good level of shine immediately after application and after 1 hour.
  • composition 1 the transfer level of the deposit is very low; the deposit obtained for composition 2 is non tacky.

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Abstract

L'invention porte sur une composition cosmétique à base d'un polymère supramoléculaire, d'une huile d'hydrocarbure non volatile et d'une huile de silicone non volatile. La présente invention porte sur des compositions pour le maquillage et/ou le soin de la peau et/ou des lèvres, comprenant : au moins un polymère supramoléculaire à base de polyalcène fonctionnalisé de formule HO-P-OH dans laquelle P représente un homopolymère ou un copolymère qui peut être obtenu par polymérisation d'un ou plusieurs alcènes polyinsaturés linéaires, cycliques et/ou ramifiés en C2-C10 et de préférence en C2-C4, qui peut être dérivé de la réaction, en particulier de la condensation, dudit polymère polyalcène fonctionnalisé avec au moins un groupe de jonction fonctionnalisé par au moins un groupe réactif pouvant réagir avec le ou les groupes réactifs du polymère polyalcène fonctionnalisé, ledit groupe de jonction pouvant former au moins 3 liaisons H (hydrogène), de préférence au moins 4 liaisons H, préférentiellement 4 liaisons H ; au moins une huile de silicone non volatile, de préférence phénylée ; et au moins une huile d'hydrocarbure non volatile, de préférence une huile d'hydrocarbure apolaire.
PCT/JP2012/066465 2012-06-21 2012-06-21 Composition cosmétique comprenant un polymère supramoléculaire, une huile de silicone non volatile et une huile d'hydrocarbure non volatile WO2013190705A1 (fr)

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JP2014561202A JP2015523959A (ja) 2012-06-21 2012-06-21 超分子ポリマー、不揮発性シリコーン油及び不揮発性炭化水素化油を含む化粧用組成物
PCT/JP2012/066465 WO2013190705A1 (fr) 2012-06-21 2012-06-21 Composition cosmétique comprenant un polymère supramoléculaire, une huile de silicone non volatile et une huile d'hydrocarbure non volatile

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PCT/JP2012/066465 WO2013190705A1 (fr) 2012-06-21 2012-06-21 Composition cosmétique comprenant un polymère supramoléculaire, une huile de silicone non volatile et une huile d'hydrocarbure non volatile

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JP6012821B1 (ja) * 2015-07-22 2016-10-25 サンユレック株式会社 ポリウレタン樹脂組成物、封止材及び電気電子部品

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EP0787731A2 (fr) 1996-01-30 1997-08-06 Ciba SC Holding AG Dicétopyrrolopyrroles et leurs polymères
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WO2011148324A2 (fr) * 2010-05-26 2011-12-01 L'oreal Composition cosmétique basée sur un polymère supramoléculaire et un composé de silicone
WO2011148327A1 (fr) * 2010-05-26 2011-12-01 L'oreal Composition cosmétique à base d'un polymère supramoléculaire et d'un agent de remplissage absorbant
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Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP6012821B1 (ja) * 2015-07-22 2016-10-25 サンユレック株式会社 ポリウレタン樹脂組成物、封止材及び電気電子部品
JP2017025197A (ja) * 2015-07-22 2017-02-02 サンユレック株式会社 ポリウレタン樹脂組成物、封止材及び電気電子部品

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