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EP2049076A1 - Procédé de maquillage ou de soin de substances kératineuses avec des polyrotaxanes non réticulés - Google Patents

Procédé de maquillage ou de soin de substances kératineuses avec des polyrotaxanes non réticulés

Info

Publication number
EP2049076A1
EP2049076A1 EP07788201A EP07788201A EP2049076A1 EP 2049076 A1 EP2049076 A1 EP 2049076A1 EP 07788201 A EP07788201 A EP 07788201A EP 07788201 A EP07788201 A EP 07788201A EP 2049076 A1 EP2049076 A1 EP 2049076A1
Authority
EP
European Patent Office
Prior art keywords
composition
polyrotaxane
noncrosslinked
weight
chosen
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Withdrawn
Application number
EP07788201A
Other languages
German (de)
English (en)
Inventor
Timo Luukas
Nathalie Jager Lezer
Pascal Arnaud
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
LOreal SA
Original Assignee
LOreal SA
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Priority claimed from FR0653297A external-priority patent/FR2904534B1/fr
Application filed by LOreal SA filed Critical LOreal SA
Publication of EP2049076A1 publication Critical patent/EP2049076A1/fr
Withdrawn legal-status Critical Current

Links

Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00—Preparations for care of the skin
    • 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
    • A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
    • A61K8/4973—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with oxygen as the only hetero atom
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
    • A61K8/73—Polysaccharides
    • A61K8/738—Cyclodextrins
    • 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
    • A61K8/84—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
    • A61K8/86—Polyethers
    • 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
    • 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
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q1/00—Make-up preparations; Body powders; Preparations for removing make-up
    • A61Q1/02—Preparations containing skin colorants, e.g. pigments
    • A61Q1/04—Preparations containing skin colorants, e.g. pigments for lips
    • A61Q1/06—Lipsticks
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • 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
    • A61Q1/08—Preparations containing skin colorants, e.g. pigments for cheeks, e.g. rouge
    • 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
    • A61Q1/10—Preparations containing skin colorants, e.g. pigments for eyes, e.g. eyeliner, mascara
    • 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
    • A61Q1/12—Face or body powders for grooming, adorning or absorbing
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
    • A61K2800/20—Chemical, physico-chemical or functional or structural properties of the composition as a whole
    • A61K2800/24—Thermal properties
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
    • A61K2800/20—Chemical, physico-chemical or functional or structural properties of the composition as a whole
    • A61K2800/26—Optical properties
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
    • A61K2800/40—Chemical, physico-chemical or functional or structural properties of particular ingredients
    • A61K2800/54—Polymers characterized by specific structures/properties
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
    • A61K2800/80—Process related aspects concerning the preparation of the cosmetic composition or the storage or application thereof
    • A61K2800/88—Two- or multipart kits
    • A61K2800/884—Sequential application
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
    • A61K2800/80—Process related aspects concerning the preparation of the cosmetic composition or the storage or application thereof
    • A61K2800/95—Involves in-situ formation or cross-linking of polymers
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q17/00—Barrier preparations; Preparations brought into direct contact with the skin for affording protection against external influences, e.g. sunlight, X-rays or other harmful rays, corrosive materials, bacteria or insect stings
    • A61Q17/04—Topical preparations for affording protection against sunlight or other radiation; Topical sun tanning preparations
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00—Preparations for care of the skin
    • A61Q19/04—Preparations for care of the skin for chemically tanning the skin

Definitions

  • a subject-matter of the present invention is a method for making up or caring for keratinous substances which consist in applying to the said keratinous substances, at least one noncrosslinked polyrotaxane and at least one second noncrosslinked polyrotaxane which crosslink on the said keratinous substances.
  • compositions according to the invention can be compositions for making up or caring for keratinous substances, in particular the skin, nails, lips and keratinous fibres, especially the eyelashes, and preferably makeup compositions.
  • Each composition can be a free or compacted powder, a foundation, a face powder, an eyeshadow, a concealer, a blusher, a lipstick, a lip balm, a lip gloss, a lip pencil, an eye pencil, a mascara, an eyeliner, a nail varnish or also a product for making up the body or for colouring the skin.
  • the care composition can be a product for caring for the eyelashes, nails or lips, for caring for the skin of the body and face, in particular an antisun product, or a product for colouring the skin (such as a self-tanning product) .
  • an effective volume can be produced by applying a light tint and a dark tint side by side, the light tint being applied to the area which it is desired to enhance.
  • To produce this effect conventionally requires the use of two different compositions and depends on the fitness of the one who is applying them. This technique is furthermore difficult to employ in making up the lips.
  • compositions having a high solids content in order to contribute material to the keratinous fibres and thus to obtain a makeup result in which volume or loading are more or less bestowed.
  • the increase in the solids content of solids leads to an increase in the consistency of the product obtained and thus to an application to fibres which is problematic and difficult as the composition is thick and viscous, gives a granular and nonsmooth appearance to the deposited layer and is deposited with difficulty, in heterogeneous fashion and in clusters.
  • the aim of the present invention is to provide a novel route for the formulation of cosmetic compositions capable of crosslinking on keratinous substances and of generating, on the said keratinous substances, a body- bestowing deposited layer having good properties of hold over time and a comfortable deposition on the skin, lips or eyelashes.
  • the inventors have discovered that it is possible to obtain such properties by using a system comprising compounds which crosslink in situ, so as to adhere better to keratinous substances.
  • these compounds absorb water, thus bringing about an increase in the volume of the deposited layer.
  • the keratinous substances thus give the impression of being thicker, fuller or smoother by filling in their rough edges.
  • a subject-matter of the invention is a cosmetic method for making up or for the nontherapeutic care of keratinous substances chosen from the nails, skin, lips or eyelashes, the method consisting in: a. depositing on the said keratinous substances at least one layer of at least one first composition comprising at least one first noncrosslinked polyrotaxane and at least one second noncrosslinked polyrotaxane, b. subjecting the said composition, simultaneously with or subsequent to its application, to at least one chemical, physicochemical and/or mechanical stimulus.
  • This first noncrosslinked polyrotaxane and this second noncrosslinked polyrotaxane which are identical or different, are capable of polymerizing when they are subjected to a stimulus, that is to say an action, for example chemical, physicochemical or mechanical action, exerted on the composition or compositions comprising them.
  • the stimulus comprises at least one crosslinking agent.
  • a subject-matter of the invention is a cosmetic method for making up or for the nontherapeutic care of keratinous substances chosen from the nails, skin, lips or eyelashes, the method consisting in depositing, on the said keratinous substances : a. at least one layer of a first composition comprising at least one first noncrosslinked polyrotaxane, b. at least one layer of a second composition comprising a crosslinking agent, the first composition and/or the second composition comprising at least one second noncrosslinked polyrotaxane .
  • the second noncrosslinked polyrotaxane is present in the first composition.
  • a crosslinking agent is grafted to the first and/or to the second polyrotaxane .
  • a further subject-matter of the invention is a cosmetic method for making up or for the nontherapeutic care of keratinous substances chosen from the nails, skin, lips or eyelashes, the method consisting in depositing, on the said keratinous substances, at least one layer of a first composition comprising at least one first noncrosslinked polyrotaxane and at least one second noncrosslinked polyrotaxane, the first noncrosslinked polyrotaxane and/or the second noncrosslinked polyrotaxane being grafted with a crosslinking agent.
  • a further subject-matter of the invention is a cosmetic method for making up or for the nontherapeutic care of keratinous substances chosen from the nails, skin, lips or eyelashes, the method consisting in depositing, on the said keratinous substances: at least one layer of a first composition comprising at least one first noncrosslinked polyrotaxane, at least one layer of a second composition comprising at least one second noncrosslinked polyrotaxane , at least one of the first and/or second noncrosslinked polyrotaxanes being grafted with a crosslinking agent.
  • first and second compositions do not in any way condition the order of application of the said compositions to the keratinous substances.
  • the second composition can be applied to the first composition and vice versa.
  • At least one layer of the first composition is applied to the keratinous substances and then at least one layer of the second composition is applied to all or part of the first layer.
  • each first and second composition can also be applied alternately to the keratinous substances .
  • a further subject-matter of the invention is a cosmetic method for making up or for the nontherapeutic care of keratinous substances chosen from the nails, skin, lips and eyelashes, consisting in: a. mixing, at the time of use: - at least one first composition comprising a cosmetically acceptable medium and at least one first noncrosslinked polyrotaxane, and at least one second composition comprising a crosslinking agent, the first composition and/or the second composition comprising at least one second noncrosslinked polyrotaxane , then b. applying at least one layer of the said mixture to the nails, skin, lips or eyelashes .
  • another subject-matter of the present invention is a kit for making up or for the nontherapeutic care of keratinous substances chosen from the nails, skin, lips and eyelashes, comprising: i) at least one first composition comprising at least one first noncrosslinked polyrotaxane , ii) at least one second composition comprising a crosslinking agent, the first composition and/or the second composition comprising at least one second noncrosslinked polyrotaxane .
  • the makeup kit according to the invention comprises the first and second compositions in separate packaging.
  • Each composition can be packaged separately in the same article of packaging, for example in a two-compartment pen, the base composition being delivered via one end of the pen and the top composition being delivered via the other end of the pen, each end being closed in particular in leaktight fashion by a cap.
  • each of the compositions can be packaged in a different article of packaging.
  • the first and second polyrotaxanes crosslink together and a deposited layer possessing good hold is obtained on the keratinous substances; this deposited layer is capable of increasing in volume by formation of a gel in the presence of a fluid.
  • This fluid preferably hydrophilic, can, for example, be sweat, saliva, tears, residual water of the skin, lips, nails and/or eyelashes, ambient moisture or any other natural or artificial liquid. It can be contributed by an external source, for example by moistening the keratinous substances before or after application of the compositions (for example with a spray, natural or artificial tears) .
  • the fluid can also be a polar solvent, such as, for example, propylene glycol or ethylene glycol .
  • the fluid in particular water, can also be added directly to the composition or compositions comprising the noncrosslinked polyrotaxane or polyrotaxanes before application.
  • the fluid can be contributed via at least one additional layer of at least one third composition comprising an aqueous medium which is applied to the layer or layers of first and/or second composition in order to bring about the swelling of the crosslinked polyrotaxane.
  • compositions make it possible to lastingly conceal defects of appearance of keratinous substances (blemishes, shadows under the eyes, folds, hollows, thinness) and may possibly confer an increased volume on the nails, skin, eyelashes or lips.
  • the first and/or the second composition it is possible to incorporate a colouring material or an active principle in the first and/or the second composition, which makes it possible to efficiently trap said active principle or said colouring material in the gel which is formed on the keratinous substances after swelling of the deposited layer .
  • these compositions can have a particular application in the field of foundations or mattifying creams.
  • the water-swollen deposited layer (gel) makes it possible to prevent dehydration of the skin and feelings of discomfort and of tightness.
  • the deposited layer obtained on the keratinous substances after application of the first and/or second compositions and then swelling with water is subjected to a heat source.
  • the heating then brings about the partial or complete evaporation of the water present in the gel and the retraction of the film on the keratinous substances and thus a tensioning effect of the film. It is thus possible to obtain, in the case of mascaras, a curving effect on the eyelashes or, in the case of products for caring for or making up the skin, an effect of smoothing the skin and of reducing wrinkles and fine lines .
  • Polyrotaxanes form part of the chemical family of the inclusion compounds, which comprise a first molecular entity which forms a cavity of limited size in which is housed a molecular entity of a second chemical type.
  • JP09216815 of Noevir Co. Ltd (1997) and JP09315937 of Shiseido Co. Ltd (1997) have described cosmetic products comprising pseudopolyrotaxanes .
  • polyrotaxane is understood to mean a supramolecular edifice which comprises at least one linear molecule and at least two cyclic molecules strung along the said linear molecule, the linear molecule and the cyclic molecules not being bonded via covalent bonds, with the result that the cyclic molecules can move freely along the linear molecule.
  • the molecules described in these documents comprise a backbone on which cyclic molecules (cyclodextrins) are included.
  • cyclic molecules cyclodextrins
  • the compositions do not increase in volume sufficiently once applied to keratinous substances and their hold over time is poor.
  • the cyclic molecules have a tendency to become unstrung when the pseudopolyrotaxane is dissolved.
  • a “polyrotaxane” is obtained from a pseudopolyrotaxane, to which is attached, at each end of the linear molecule, a “blocking" molecular structure which prevents the cyclic molecules and the linear molecule from separating, if appropriate.
  • composition or compositions employed in the process according to the invention comprise at least one first noncrosslinked polyrotaxane and at least one second noncrosslinked polyrotaxane, that is to say compounds which are not bonded to one another and which, subjected to a stimulus, are capable of crosslinking with one another, by formation of at least one bond, which can be chemical or physical, between a cyclic molecule of the first polyrotaxane and at least one cyclic molecule of the second polyrotaxane, to form a crosslinked polyrotaxane.
  • the bond can in particular be a metallic bond, an ionic bond, a covalent bond, an interaction resulting from the formation of charge transfer complexes, a weak interaction of hydrogen bond, Van der Waal's bond or ⁇ - ⁇ bond type, or a mixture of these.
  • a polyrotaxane is thus a supramolecular assemblage in which cyclic molecules are "included" by a linear molecule. To prevent the cyclic molecules from becoming unstrung from the linear molecule, the ends of the linear molecule are functionalized by bulky or ionic groups (blocking molecular structures) .
  • linear molecule is intended to denote a substantially “linear” molecule. This means that a linear molecule can comprise one or more branch chains, provided that the cyclic molecules can be rotated about or moved along the linear molecule.
  • the length of the "linear" molecule is not limited to a specific length, provided that the linear molecule allows the cyclic molecules to turn round on themselves or to move along the said linear molecule.
  • the linear molecule of the first polyrotaxane and/or the linear molecule of the second polyrotaxane can be chosen independently of one another from polymers, in particular:
  • - hydrophilic polymers such as a poly (vinyl alcohol) , a polyvinylpyrrolidone, a poly ( (meth) acrylic acid), polymers derived from cellulose (carboxymethyl- cellulose, hydroxyethylcellulose, hydroxypropyl - cellulose and the like) , a polyacrylamide, polyalkylene glycols, such as polyethylene glycols and polypropylene glycols, polytetrahydrofurans, poly (vinyl acetal)s, a poly (vinyl methyl ether), polyamines, polyethylene- imine, casein, gelatin, starch, and their copolymers; - hydrophobic polymers, for example polyolefins, such as polyethylenes, polypropylenes, polyisoprenes, polyisobutylenes or polybutadienes ; copolymers of olefins, such as ethylene/butylene copolymers; polyesters, polydimethylsi
  • Polyethylene glycols are particularly preferred.
  • the linear molecules advantageously have, independently of one another, a weight-average molecular weight of greater than or equal to 350 g/mol, for example ranging from 350 to 2 000 000, preferably ranging from 1500 to 1 000 000, more preferably ranging from 2800 to 800 000, even better still ranging from 7000 to 700 000, for example ranging from 10 000 to 600 000 or from 10 000 to 500 000.
  • the linear molecules preferably carry reactive groups at each end.
  • the fact of carrying the reactive groups makes it possible to facilitate the reaction with the molecular structures intended to prevent separation between the linear molecules and the cyclic molecules which they carry.
  • the reactive groups depend on the blocking molecular structures to be employed. Mention may be made, as examples, of hydroxyl groups, amino groups, tosylate groups, polymerizable groups, activated ester groups, such as N-hydroxysuccinimide ester groups, carboxyl groups, thiol groups and the like.
  • a "cyclic molecule” denotes a molecule comprising at least one cyclic structure.
  • the cyclic molecule can comprise two or more cyclic structures or a double ring.
  • the cyclic molecule can be a macrocycle, such as a cyclodextrin.
  • the cyclic molecules of the first and second polyrotaxanes can be chosen, independently of one another, from:
  • - cyclodextrins for example ⁇ -cyclodextrin, ⁇ - cyclodextrin, ⁇ -cyclodextrin, dimethylcyclodextrin and glucosylcyclodextrin, and their derivatives, - crown ethers,
  • the size of the internal cavity or cavities of the cyclic molecules can vary according to the linear molecule chosen. In any case, cyclic molecules are chosen which can be strung along the linear molecule.
  • the cavity of the cyclic molecule will preferably have a diameter greater than the diameter of the cross section of a minimum imaginary cylinder in which the linear molecule can be included.
  • ⁇ -cyclodextrin is used as cyclic molecule and a polyethylene glycol is used as linear molecule.
  • the cyclic molecules preferably have groups capable of generating bonds which are not situated in their cavity. This makes it possible to subsequently bond the cyclic molecules to one another via a chemical or physical bond.
  • the reactive groups of the cyclic molecules can comprise, for example, hydroxyl , amino, carboxyl or thiol groups. Furthermore, it is preferable to choose cyclic molecules having reactive groups which do not react with the blocking structures during the blocking reaction between the said blocking structures and the linear molecules.
  • the ratio of the number of cyclic molecules strung along a linear molecule to the maximum amount of cyclic molecules of the same nature which could be strung along this linear molecule ranges from 0.001 to 0.6, preferably from 0.01 to 0.5 and better still from 0.05 to 0.4. This ratio may be referred to as "inclusion amount" .
  • the maximum inclusion amount is standardized as being equal to 1. It corresponds to the amount at which a linear molecule makes it possible to include a maximum of cyclic molecules.
  • the linear molecule it is preferable for the linear molecule not to exhibit a dense stack of cyclic molecules.
  • This dense stack state corresponding to the maximum inclusion amount equal to 1.
  • the fact of creating a non-dense stack of cyclic molecules makes it possible to retain molecular segments which can be moved, with the result that the crosslinked polyrotaxane exhibits a high fracture strength, a high entropic elasticity, a superior expandability and/or a superior restoring property, and, if desired, a high absorbability or a high hygroscopicity .
  • the cyclic molecules can be cyclized after inclusion of the linear molecules. More specifically, it is possible to use a precursor of the cyclic molecules having at least one open segment analogous to the letter "C" .
  • the "C” segments can be closed after the inclusion of the linear molecule or after the blocking of the linear molecule with a blocking group.
  • the molecules having a segment analogous to the letter "C” see M. Asakawa et al . , Angewandte Chemie International, 37(3), 333-337 (1998), and M. Asakawa et al . , European Journal of Organic Chemistry, 5, 985-994 (1999) , both being incorporated here by way of reference .
  • the blocking structures have to keep the cyclic molecules strung along the linear molecule.
  • These blocking structures can prevent the cyclic molecules from separating from the linear molecule due to their high steric volume.
  • the blocking structures situated at each end of each linear molecule can also prevent the cyclic molecules from decomplexing from the linear molecule by exhibiting specific ionic charges.
  • molecular structure denotes here a molecule, a macromolecule or a solid support.
  • a macromolecule or a solid support can include several blocking sites.
  • a blocking structure of a macromolecule can be present in the main chain or in a side chain.
  • the macromolecule A can constitute a matrix, a portion of which comprises pseudopolyrotaxanes, or conversely the pseudopolyrotaxane can constitute a matrix, a portion of which comprises the macromolecule A.
  • the blocking molecular structures can be chosen from:
  • - dinitrophenyl groups such as the 2,4- and 3,5- dinitrophenyl groups,- - cyclodextrins ;
  • the cyclic molecules can be chosen from ⁇ -cyclodextrin, dinitrophenyl groups, such as the 2,4- and 3 , 5 -dinitrophenyl groups, adamantane groups, trityl groups, fluoresceins, pyrenes and their combinations .
  • the first and/or second polyrotaxanes are capable of crosslinking by formation of at least one chemical bond or of at least one physical bond (preferably at least two physical bonds) between at least one cyclic molecule of the noncrosslinked polyrotaxanes, when they are subjected to a stimulus.
  • the stimulus can be an action, for example a chemical, physicochemical or mechanical action, exerted on the first composition and/or the second composition.
  • crosslinking can thus be carried out thermally, photochemically, chemically and/or mechanically, in the presence or absence of a crosslinking agent.
  • composition can, for example, be carried out at the temperature of the skin or by using means not specifically intended for heating, such as a hot body (cup or a hot drink) .
  • the composition can also be heated using a means specifically dedicated to heating, such as, for example, a means which propels hot air, such as a hairdryer, or a heating device, such as, for example, a heating applicator.
  • the first and second polyrotaxanes crosslink via a chemical or physical bond which can be formed by a simple bond or by a bond involving different atoms or molecules.
  • the said bond can be obtained by reaction of the said two cyclic molecules with a crosslinking agent or a photocrosslinking agent.
  • crosslinking agent is understood to mean a compound capable of creating at least one chemical bond (covalent bond) or physical bond (ionic bond, hydrogen bond, ⁇ - ⁇ interactions or Van der Waals forces) between two or more molecules .
  • a cyclic molecule preferably has one or more reactive groups on the outside of the nucleus, as described above.
  • This reaction can be carried out under the action of temperature or of a variation in pH .
  • the conditions of the crosslinking reaction must be conditions under which the blocking groups of the blocked polyrotaxane are not removed.
  • the first composition and/or the second composition comprises at least one crossing agent, alone or in combination with the noncrosslinked polyrotaxane or polyrotaxanes.
  • the crosslinking agent can be grafted to a filler or to a colouring material, such as those described later.
  • the crosslinking agent is grafted to the first and/or second noncrosslinked polyrotaxane, in particular to the cyclic segment of the said noncrosslinked polyrotaxane or polyrotaxanes.
  • the first composition or the second composition additionally comprises at least one crosslinking agent.
  • the composition comprising a crosslinking agent does not comprise noncrosslinked polyrotaxane; in particular, the first composition employed in the process according to the invention does not comprise crosslinking agent.
  • crosslinking agents Use may be made, as crosslinking agents, of crosslinking agents well known in the prior art.
  • Use may be made, for example, of: i) compounds having at least two polymerizable double bonds, such as, for example di- or polyvinyl compounds, such as divinylbenzene, divinyltoluene, divinylxylene, divinyl ether, divinyl ketone, divinyl sulphone or trivinylbenzene , di- or polyesters resulting from the reaction of unsaturated mono- or polycarboxylic acids with polyols, such as di- or triesters of (meth) acrylic acids and of polyols chosen, for example, from ethylene glycol, trimethylolpropane, glycerol, polyoxyethylene glycols, polyoxypropylene glycols and their mixtures; polyesters resulting from the reaction of any one of the abovementioned polyols with an unsaturated (or ethylenic) carboxylic acid, such as, for example, maleic acid; esters resulting from the reaction of a polyepoxide
  • carbamyl esters resulting from the reaction of polyisocyanates such as tolylene diisocyanate, hexamethylene diisocyanate, 4 , 4 ' -diphenylmethane diisocyanate, phenylene diisocyanates, 1,1'- carbonyldiimidazole or prepolymers comprising an NCO group obtained by reacting such diisocyanates with compounds comprising active hydrogen atoms) with monomers comprising hydroxyl groups
  • the dicarbamyl esters of (meth) acrylic acids obtained, for example, by reaction of the abovementioned diisocyanates with hydroxyethyl (meth) acrylates, di- or poly (meth) allyl ethers or polyols, such as alkylene glycols, glycerol, polyalkylene glycols, polyoxyalkylene polyols or carbohydrates, such as polyethylene glycol diallyl ether, allylated
  • glyoxal polycarboxylic acids, such as phthalic acid or adipic acid
  • polyols such as ethylene glycol
  • polyamines such as alkylenediamines (for example, ethylenediamine) or polyalkylenepolyamines
  • bis- or polyepoxides such as glycidyl epoxides, cycloaliphatic epoxides (for example, 3,4- epoxycyclohexylmethyl 3,4- epoxycyclohexanecarboxylate)
  • epoxidized vegetable oils such as epoxidized soybean or linseed oils
  • polyethylene oxide- succinimidyl glutarates such as polyethylene oxide-tetrasuccinimidyl glutarate, bisepoxybutane or glycidyl ethers, such as bisphenol A diglycidyl ether, bishydrazides, tris- or polyhydrazides, carbodiimi
  • cyanuric chloride trimesoyl chloride, terephthaloyl chloride, epichlorohydrin, dibromobenzene, glutaraldehyde, bis (acid chlorides) (for example, sebacoyl dichloride) , tri (acid chlorides) and the like.
  • the crosslinking agent can be chosen from coupling agents of silane type (for example, alkoxysilanes) and/or titanium-based coupling agents (for example alkoxytitanium compounds) .
  • crosslinking agents of crosslinking agents capable of forming, between them, at least two physical bonds (in particular hydrogen bonds) , it being possible for these crosslinking agents to be, independently of one another, carried by a noncrosslinked polyrotaxane or present in either of the first and/or second compositions. Mention may be made, as examples of such agents, of the 2 , 6-diaminopyridine and uracils pair, the barbituric acid and triaminopyridines pair, or also ureidopyrimidinones, ureidotriazines or cyanuric acid derivatives which crosslink with one another.
  • crosslinking agent capable of establishing one or more ionic bonds
  • polyvalent metallic compounds which form ionic crosslinkings, such as, for example, oxides, hydroxides and weak acid salts
  • alkaline earth metals for example, calcium or magnesium
  • alkaline earth metals for example, calcium or magnesium
  • zinc or of aluminium mention may be made, for example, of calcium oxide, zinc diacetate or aluminium sulphate .
  • crosslinking agents also known under the name of "synthons" are described, for example, in the following references: "Supramolecular Polymers", L. Brunsveld, B. J. B. Folmer, E. W. Meijer and R. P. Sijbesma, Chemical Reviews, 2001, 4071-4098 or Supramolecular Chemistry, JM Lehn, VCH, 1995.
  • photocrosslinking agents which are employed for materials designed for soft contact lenses
  • photocrosslinking agents based on stilbazolium salts such as formylstyrylpyridinium salts (see K. Ichimura et al . , Journal of Polymer Science, edition on the chemistry of polymers, 20, 1411-1432 (1982), incorporated here by way of reference)
  • photocrosslinking agents for example photocrosslinking agents by photodimerization, specifically cinnamic acid, anthracene, thymines and the like.
  • the crosslinking agents preferably have weight-average molecular weights of less than 2000, preferably of less than 1000, better still of less than 600 and very particularly of less than 400.
  • crosslinking agent of cyanuric chloride, tolylene 2,4- diisocyanate, 1 , 1 ' -carbonyldiimidazole, trimesoyl chloride, terephthaloyl chloride, alkoxysilanes , such as tetramethoxysilane and tetraethoxysilane, cycloaliphatic epoxides, such as 3,4- epoxycyclohexylmethyl 3 , 4-epoxycyclohexanecarboxylate, polyethylene oxide- succinimidyl glutarates, such as polyethylene oxide-tetrasuccinimidyl glutarate, bishydrazides, and the like, and their mixtures.
  • ⁇ -cyclodextrin it is preferable to use ⁇ -cyclodextrin as cyclic molecule and where a crosslinking agent is used to crosslink it, mention may be made, as examples of crosslinking agent, of cyanuric chloride
  • the cyclic molecules and the linear molecules are mixed in order to prepare the pseudopolyrotaxanes, in which the cyclic molecules are strung along the linear molecules.
  • the polyrotaxanes are prepared by blocking each end of the linear molecules with blocking groups, so as to prevent the removal of the cyclic molecules.
  • ⁇ -cyclodextrin is used as cyclic molecule
  • a polyethylene glycol is used as linear molecule
  • a 2 , 4-dinitrophenyl group is used as blocking group
  • cyanuric chloride is used as crosslinking agent.
  • each end of the polyethylene glycol is converted to an amino group, in order to be able subsequently to attach a blocking group to the end of the polyethylene glycol and to form the polyrotaxane.
  • a blocking group to the end of the polyethylene glycol and to form the polyrotaxane.
  • diamine- terminated PEG/PPO copolymers sold by Huntsman under the Jeffamine reference.
  • the ⁇ -cyclodextrin and the aminated polyethylene glycol derivative are mixed in order to prepare the pseudopolyrotaxane .
  • the duration of the mixing ranges from 1 to 48 hours and the mixing temperature ranges from 0 to 100 0 C, so that the inclusion amount of ⁇ -cyclodextrin with regard to the polyethylene glycol derivative ranges from 0.001 to 0.6.
  • a polyethylene glycol having an average molecular weight of 20 000 makes it possible to include at most 230 ⁇ -cyclodextrin molecules.
  • the maximum inclusion amount, corresponding to 230 molecules, is equal to 1.
  • 60 to 65 (63) ⁇ -cyclodextrin molecules are on average strung over one polyethylene glycol molecule, which corresponds to a degree of inclusion ranging from 0.26 to 0.29 (0.28) with respect to the maximum inclusion amount.
  • the ⁇ - cyclodextrin inclusion amount can be determined by NMR, light absorption or elemental analysis.
  • the pseudopolyrotaxane obtained is reacted with 2,4- dinitrofluorobenzene dissolved in DMF, which makes it possible to obtain the noncrosslinked polyrotaxane .
  • the polyrotaxane can be used as is or partially or completely prehydrated.
  • the first and second noncrosslinked polyrotaxanes can be present in a content ranging from 0.1 to 80% by weight, preferably from 1 to 50% by weight and more preferably from 2 to 30% by weight, with respect to the total weight of each first or second composition.
  • the first and/or second composition according to the invention comprises, in addition to the first nonerossiinked polyrotaxane and/or the second noncrosslinked polyrotaxane, at least one crosslinked polyrotaxane which has been obtained by crosslinking, prior to its introduction into the composition, at least one first noncrosslinked polyrotaxane and at least one second noncrosslinked polyrotaxane, as described above.
  • the first composition and/or the second composition advantageously comprises a liquid fatty phase.
  • liquid fatty phase is understood to mean, within the meaning of the patent application, a fatty phase which is liquid at ambient temperature (25 0 C) and atmospheric pressure (760 mmHg) and which is composed of one or more nonaqueous fatty substances which are liquid at ambient temperature, also known as oils or organic solvents.
  • the oil can be chosen from volatile oils and/or non- volatile oils, and their mixtures.
  • the oil or oils can be present in the composition according to the invention in a content ranging from 1% to 80% by weight, preferably from 5% to 50% by weight, with respect to the total weight of the composition.
  • volatile oil is understood to mean, within the meaning of the invention, an oil capable of evaporating on contact with keratinous substances in less than one hour at ambient temperature and atmospheric pressure.
  • volatile organic solvent or solvents and the volatile oils of the invention are volatile cosmetic organic solvents and oils which are liquid at ambient temperature and which have a nonzero vapour pressure, at ambient temperature and atmospheric pressure, ranging in particular from 0.13 Pa to 40 000 Pa (10 ⁇ 3 to 300 mmHg) , in particular ranging from 1.3 Pa to 13 000 Pa (0.01 to 100 mmHg) and more particularly ranging from 1.3 Pa to 1300 Pa (0.01 to 10 mmHg) .
  • nonvolatile oil is understood to mean an oil which remains on keratinous substances at ambient temperature and atmospheric pressure for at least several hours and which has in particular a vapour pressure of less than 10 "3 mmHg (0.13 Pa).
  • oils can be hydrocarbon oils, silicone oils, fluorinated oils or their mixtures.
  • hydrocarbon oil is understood to mean an oil comprising mainly hydrogen and carbon atoms and optionally oxygen, nitrogen, sulphur and phosphorus atoms.
  • Volatile hydrocarbon oils can be chosen from hydrocarbon oils having from 8 to 16 carbon atoms, in particular branched C 8 -Ci 6 alkanes, such as C 8 -Ci 6 isoalkanes of petroleum origin (also known as isoparaffins) , such as isododecane (also known as 2 , 2 , 4 , 4 , 6-pentamethylheptane) , isodecane or isohexa- decane, for example the oils sold under the Isopar or Permethyl tradenames, branched C 8 -Ci 6 esters, isohexyl neopentanoate, and their mixtures.
  • volatile hydrocarbon oils such as petroleum distillates, in particular those sold under the Shell SoIt name by Shell
  • the volatile solvent is chosen from volatile hydrocarbon oils having from 8 to 16 carbon atoms and their mixtures.
  • volatile oils such as, for example, volatile linear or cyclic silicone oils, in particular those having a viscosity ⁇ 8 centistokes (8 x 10 ⁇ 6 m 2 /s) and having in particular from 2 to 7 silicon atoms, these silicones optionally comprising alkyl or alkoxy groups having from 1 to 10 carbon atoms.
  • volatile silicone oil which can be used in the invention, of octamethylcyclotetrasiloxane, decamethyl- cyclopentasiloxane, dodecamethylcyclohexasiloxane, heptamethylhexyltrisiloxane, heptamethyloctyltri- siloxane, hexamethyldisiloxane, octamethyltrisiloxane, decamethyltetrasiloxane, dodecamethylpentasiloxane and their mixtures.
  • R represents an alkyl group comprising from 2 to 4 carbon atoms, one or more hydrogen atoms of which can be substituted by a fluorine or chlorine atom.
  • the first and/or second composition can also comprise at least one nonvolatile oil, chosen in particular from nonvolatile hydrocarbon oils and/or silicone oils and/or fluorinated oils.
  • nonvolatile hydrocarbon oil of: hydrocarbon oils of vegetable origin, such as triesters of fatty acids and of glycerol, the fatty acids of which can have varied chain lengths from C 4 to C 24 , it being possible for these chains to be linear or branched and saturated or unsaturated; these oils are in particular wheat germ, sunflower, grape seed, sesame, maize, apricot kernel, castor, shea, avocado, olive, soybean, sweet almond, palm, rapeseed, cottonseed, hazelnut, macadamia, jojoba, alfalfa, poppy, pumpkinseed, cucumber, blackcurrant seed, evening primrose, millet, barley, quinoa, rye, safflower, candlenut, passionflower or musk rose oil; or triglycerides of caprylic/capric acids, such as those sold by Stearineries Dubois or those sold under the names Miglyol 810, 812 and 8
  • the nonvolatile silicone oils which can be used in the composition according to the invention can be polydimethylsiloxanes (PDMSs) which are nonvolatile, polydimethylsiloxanes comprising pendent alkyl or alkoxy groups and/or alkyl or alkoxy groups at the end of the silicone chain, groups each having from 2 to 24 carbon atoms, phenylated silicones, such as phenyl trimethicones, phenyl dimethicones, phenyl (trimethyl - siloxy) diphenylsiloxanes, diphenyl dimethicones, diphenyl (methyldiphenyl) trisiloxanes or (2-phenyl- ethyl) trimethylsiloxysilicates .
  • PDMSs polydimethylsiloxanes
  • fluorinated oils which can be used in the invention are in particular fluorosilicone oils, fluorinated polyethers or fluorinated silicones, such as disclosed in the document EP-A-847 752.
  • the fatty phase advantageously comprises an ester oil.
  • This ester oil can be chosen from the esters of monocarboxylic acids with monoalcohols and polyalcohols .
  • the said ester corresponds to the following formula (I) : where Ri represents a linear or branched alkyl radical of 1 to 40 carbon atoms, preferably of 7 to 19 carbon atoms, optionally comprising one or more ethylenic double bonds and optionally substituted,
  • R 2 represents a linear or branched alkyl radical of
  • 1 to 40 carbon atoms preferably of 3 to 30 carbon atoms and better still of 3 to 20 carbon atoms, optionally comprising one or more ethylenic double bonds and optionally substituted.
  • Ri and/or R 2 can carry one or more substituents chosen, for example, from groups comprising one or more heteroatoms chosen from 0, N and S, such as amino, amine, alkoxy or hydroxyl .
  • the total number of carbon atoms of Ri + R 2 is > 9.
  • Ri can represent the residue of a linear or, preferably, branched fatty acid, preferably a higher fatty acid, comprising from 1 to 40 and better still from 7 to 19 carbon atoms and R 2 can represent a linear or, preferably, branched hydrocarbon chain comprising from 1 to 40, preferably from 3 to 30 and better still from 3 to 20 carbon atoms. Again, preferably, the number of carbon atoms of Ri + R 2 > 9.
  • Ri groups are those derived from the fatty acids chosen from the group consisting of acetic, propionic, butyric, caproic, caprylic, pelargonic, capric, undecanoic, lauric, myristic, palmitic, stearic, isostearic, arachidic, behenic, oleic, linolenic, linoleic, eleostearic, arachidonic and erucic acids and of their mixtures.
  • esters are, for example, Purcellin oil
  • cetearyl octanoate isononyl isononanoate, isopropyl myristate, 2-ethylhexyl palmitate, 2-octyldodecyl stearate, 2-octyldodecyl erucate, isostearyl isostearate and the heptanoates, octanoates, decanoates or ricinoleates of alcohols or of polyalcohols, for example of fatty alcohols.
  • the esters are chosen from the compounds of the above formula (I) in which Ri represents an unsubstituted linear or branched alkyl group of 1 to 40 carbon atoms, preferably of 7 to 19 carbon atoms, optionally comprising one or more ethylenic double bonds and R 2 represents an unsubstituted linear or branched alkyl group of 1 to 40 carbon atoms, preferably of 3 to 30 carbon atoms and better still of 3 to 20 carbon atoms, optionally comprising one or more ethylenic double bonds.
  • Ri represents an unsubstituted linear or branched alkyl group of 1 to 40 carbon atoms, preferably of 7 to 19 carbon atoms, optionally comprising one or more ethylenic double bonds
  • R 2 represents an unsubstituted linear or branched alkyl group of 1 to 40 carbon atoms, preferably of 3 to 30 carbon atoms and better still of 3 to 20 carbon atoms, optionally comprising one or more eth
  • Ri is an unsubstituted branched alkyl group of 4 to 14 carbon atoms, preferably of 8 to 10 carbon atoms
  • R 2 is an unsubstituted branched alkyl group of 5 to 15 carbon atoms, preferably of 9 to 11 carbon atoms.
  • Ri-CO- and R 2 have the same number of carbon atoms and derive from the same radical, preferably unsubstituted branched alkyl, for example isononyl, that is to say that, advantageously, the molecule of ester oil is symmetrical .
  • the ester oil will preferably be chosen from the following compounds: isononyl isononanoate, cetearyl octanoate, isopropyl myristate, - 2-ethylhexyl palmitate, 2-octyldodecyl stearate, 2-octyldodecyl erucate, isostearyl isostearate.
  • compositions are intended to be applied to the lips, use may in particular be made of a "viscous" oil, that is to say an oil having a viscosity at 25 0 C advantageously of greater than or equal to 200 cSt, in particular of greater than or equal to 500 cSt, indeed even of greater than or equal to 1000 cSt .
  • the viscous oil advantageously exhibits a molecular weight of greater than or equal to 600 g/mol, for example of greater than or equal to 700, indeed even 800, indeed even 900 g/mol.
  • the dynamic viscosity at 25 0 C of the viscous oil can be measured with a Mettler RM 180 rotational viscometer, the density of the oil being taken into consideration in carrying out the conversion to cSt .
  • the Mettler RM 180 device can be equipped with various spindles according to the order of magnitude of the viscosity which it is desired to measure.
  • the device For a viscosity of between 0.18 and 4.02 Pa- s, the device is equipped with a spindle 3.
  • the device For a viscosity of between 1 and 24 Pa- s, the device is equipped with a spindle 4 and, for a viscosity of between 8 and 122 Pa- s, the device is equipped with a spindle 5.
  • the viscosity is read on the device in deviation units (DU) . Reference is subsequently made to grafts supplied with the measurement device in order to obtain the corresponding value in poises and then to carry out the conversion to stokes.
  • DU deviation units
  • the rotational speed of the spindle is 200 revolutions/min.
  • the viscosity value of the oil can vary over time. Measurements are taken at regular time intervals until they become constant. The value of the viscosity which has become constant over time is the value selected as being the value of the dynamic viscosity of the viscous oil.
  • This oil can be chosen from: a) silicone oils, such as
  • polydimethylsiloxanes optionally comprising a C 3 -C 40 alkyl or C 3 -C 40 alkoxy chain or a phenyl radical; polydimethylsiloxanes comprising phenylated radicals can be chosen from phenyl trimethicones ;
  • polyalkylmethylsiloxanes such as polymethyltrifluoropropyldimethylsiloxanes, polyalkylmethylsiloxanes substituted by functional groups, such as hydroxyl, thiol and/or amine groups,- - polysiloxanes modified by fatty acids, fatty alcohols or polyoxyalkylenes,
  • nonpolar hydrocarbon oils such as squalene, linear or branched hydrocarbons, such as paraffin, petrolatum and naphthalene oils, hydrogenated or partially hydrogenated polyisobutene, isoeicosane, squalane, decene/butene copolymers, polybutene/polyisobutene copolymers, in particular Indopol L- 14, polydecenes, such as Puresyn 10, and their mixtures.
  • nonpolar hydrocarbon oils such as squalene, linear or branched hydrocarbons, such as paraffin, petrolatum and naphthalene oils, hydrogenated or partially hydrogenated polyisobutene, isoeicosane, squalane, decene/butene copolymers, polybutene/polyisobutene copolymers, in particular Indopol L- 14, polydecenes, such as Puresyn 10, and their mixtures.
  • the fatty phase can represent from 5 to 80% by weight, with respect to the total weight of the composition, preferably from 10 to 60% and more preferably still from 15 to 50% by weight.
  • the first composition and/or the second composition employed in the process according to the invention are anhydrous, that is to say devoid of water other than the residual water contributed by some compounds .
  • the first and/or the second composition can comprise an aqueous phase .
  • the aqueous phase can be composed essentially of water; it can also comprise a mixture of water and of water- miscible solvent (miscibility in water of greater the 50% by weight at 25 0 C) , such as lower monoalcohols having from 1 to 5 carbon atoms, for example ethanol or isopropanol, glycols having from 2 to 8 carbon atoms, such as propylene glycol, ethylene glycol, 1,3-butylene glycol or dipropylene glycol, C 3 -C 4 ketones, C 3 -C 4 aldehydes and their mixtures.
  • water- miscible solvent miscibility in water of greater the 50% by weight at 25 0 C
  • lower monoalcohols having from 1 to 5 carbon atoms
  • glycols having from 2 to 8 carbon atoms such as propylene glycol, ethylene glycol, 1,3-butylene glycol or dipropylene glycol, C 3 -C 4 ketones, C 3 -C 4 aldehydes and
  • the aqueous phase can, in this case, represent from 5 to 95% by weight, with respect to the total weight of the composition comprising it, preferably from 10 to 85% by weight.
  • composition according to the invention can also comprise at least one fatty substance which is solid at ambient temperature chosen in particular from waxes, pasty fatty substances and their mixtures.
  • fatty substances can be of animal, vegetable, mineral or synthetic origin.
  • composition according to the invention can comprise a wax or a mixture of waxes .
  • the wax under consideration in the context of the present invention is generally a lipophilic compound which is solid at ambient temperature (25 0 C) , which exhibits a reversible solid/liquid change in state and which has a melting point of greater than or equal to 3O 0 C which can range up to 12O 0 C.
  • the waxes suitable for the invention can exhibit a melting point of greater than approximately 45 0 C and in particular of greater than 55 0 C.
  • the melting point of the wax can be measured using a differential scanning calorimeter (DSC) , for example the calorimeter sold under the name DSC 30 by Mettler.
  • DSC differential scanning calorimeter
  • the measurement protocol is as followed: A 15 mg sample of the product placed in a crucible is subjected to a first rise in temperature ranging from O 0 C to 12O 0 C at a heating rate of 1O 0 C/ minute, is then cooled from 12O 0 C to O 0 C at a cooling rate of 10°C/minute and, finally, is subjected to a second rise in temperature ranging from O 0 C to 12O 0 C at a heating rate of 5°C/minute.
  • the variation in the difference in power absorbed by the empty crucible and by the crucible comprising the sample of product is measured as a function of the temperature.
  • the melting point of the compound is the value of the temperature corresponding to the tip of the peak of the curve representing the variation in the difference in powder absorbed as a function of the temperature.
  • the waxes capable of being used in the compositions according to the invention are chosen from waxes of animal, vegetable, mineral or synthetic origin, and their mixtures, which are deformable or nondeformable solids at ambient temperature.
  • the wax can also exhibit a hardness ranging from 0.05 MPa to 30 MPa and preferably ranging from 6 MPa to 15 MPa.
  • the hardness is determined by the measurement of the compressive force measured at 2O 0 C using a texture analyser sold under the name TA-TX2i by Rheo, equipped with a stainless steel cylinder with a diameter of 2 mm which is displaced at the measuring rate of 0.1 mm/s, and which penetrates the wax to a penetration depth of 0.3 mm.
  • the measurement protocol is as follows:
  • the wax is melted to a temperature equal to the melting point of the wax +2O 0 C.
  • the molten wax is cast in a receptacle with a diameter of 30 mm and a depth of 20 mm.
  • the wax is recrystallized at ambient temperature
  • the value of the hardness is the maximum compressive force measured divided by the surface area of the cylinder of the texture analyser in contact with the wax.
  • hydrocarbon waxes such as beeswax, lanolin wax and Chinese insect waxes,- rice wax, carnauba wax, candelilla wax, ouricury wax, esparto wax, cork fibre wax, sugarcane wax, Japan wax and sumac wax; montan wax, microcrystalline waxes, paraffin waxes and ozokerite,- polyethylene waxes, waxes obtained by the Fischer-Tropsch synthesis and waxy copolymers, and also their esters.
  • hydrocarbon waxes such as beeswax, lanolin wax and Chinese insect waxes,- rice wax, carnauba wax, candelilla wax, ouricury wax, esparto wax, cork fibre wax, sugarcane wax, Japan wax and sumac wax
  • montan wax microcrystalline waxes, paraffin waxes and ozokerite,- polyethylene waxes, waxes obtained by the Fischer-Tropsch synthesis and waxy copolymers, and also their est
  • waxes obtained by catalytic hydrogenation of animal or vegetable oils having linear or branched C 8 -C 32 fatty chains Mention may also be made of the waxes obtained by catalytic hydrogenation of animal or vegetable oils having linear or branched C 8 -C 32 fatty chains.
  • hydrogenated jojoba oil isomerized jojoba oil, such as the trans-isomerized partially hydrogenated jojoba oil manufactured or sold by Desert Whale under the commercial reference Iso-Jojoba-50 ® , hydrogenated sunflower oil, hydrogenated castor oil, hydrogenated coconut oil, hydrogenated lanolin oil, di (1,1,1- trimethylolpropane) tetrastearate, sold under the name "Hest 2T-4S" by Heterene, or di (1,1,1- trimethylolpropane) tetrabehenate, sold under the name "Hest 2T-4B" by Heterene.
  • isomerized jojoba oil such as the trans-isomerized partially hydrogenated jojoba oil manufactured or sold by Desert Whale under the commercial reference Iso-Jojoba-50 ®
  • hydrogenated sunflower oil hydrogenated castor oil
  • hydrogenated coconut oil hydrogenated lanolin oil
  • silicone waxes such as alkyl or alkoxy dimethicones having from 16 to 45 carbon atoms, or fluorinated waxes.
  • Use may also be made of the wax obtained by hydrogenation of olive oil esterified with stearyl alcohol sold under the name “Phytowax Olive 18 L 57” or else of the waxes obtained by hydrogenation of castor oil esterified with cetyl alcohol sold under the names "Phytowax castor 16L64" and “Phytowax castor 22L73” by Sophim.
  • Such waxes are described in Application FR-A-2 792 190.
  • the compositons according to the invention can comprise at least one wax known as "tacky wax", that is to say having a tack of greater than or equal to 0.7 N. s and a hardness of less than or equal to 3.5 MPa.
  • tacky wax that is to say having a tack of greater than or equal to 0.7 N. s and a hardness of less than or equal to 3.5 MPa.
  • tacky wax can in particular make it possible to obtain a cosmetic composition which is easily applied to keratinous fibres, which has good attachment to keratinous fibres and which results in the formation of a smooth, homogeneous and thickening makeup .
  • the tacky wax used can in particular have a tack ranging from 0.7 N. s to 30 N. s, in particular of greater than or equal to 1 N.s, in particular ranging from 1 N.s to 20 N.s, especially of greater than or equal to 2 N.s, in particular ranging from 2 N.s to 10 N.s, and especially ranging from 2 N.s to 5 N.s.
  • the tack of the wax is determined by the measurement of the change in the force (compressive force or stretching force) as a function of the time at 2O 0 C using the texture analyser sold under the name "TA-TX2i ® " by Rheo, equipped with a spindle made of acrylic polymer in the shape of a cone forming an angle of 45° .
  • the measurement protocol is as follows:
  • the wax is melted at a temperature equal to the melting point of the wax +1O 0 C.
  • the molten wax is cast in a receptacle with a diameter of 25 mm and a depth of
  • the spindle of the texture analyser is displaced at the rate of 0.5 mm/s and then penetrates the wax to a penetration depth of 2 mm.
  • the spindle is held stationary for 1 second (corresponding to the relaxation time) and is then withdrawn at the rate of 0.5 mm/s .
  • the tack corresponds to the integral of the curve of the force as a function of the time for the part of the curve corresponding to the negative values of the force (stretching force) .
  • the value of the tack is expressed in N. s .
  • the tacky wax which can be used generally has a hardness of less than or equal to 3.5 MPa, in particular ranging from 0.01 MPa to 3.5 MPa, especially ranging from 0.05 MPa to 3 MPa, indeed even also ranging from 0.1 MPa to 2.5 MPa.
  • the hardness is measured according to the protocol described above. Use may be made, as tacky wax, of a C 2 O-C 4 O alkyl
  • hydroxystearyloxy (the alkyl group comprising from 20 to 40 carbon atoms) , alone or as a mixture, in particular a C 20 -C 40 alkyl 12- (12'- hydroxystearyloxy) stearate .
  • Such a wax is sold in particular under the names “Kester Wax K 82 P ®” and “Kester Wax K 80 P ®” by Koster Keunen.
  • the abovementioned waxes generally exhibit a starting melting point of less than 45 0 C.
  • the wax or waxes can be present in the form of an aqueous wax microdispersion.
  • aqueous wax microdispersion is understood to mean an aqueous dispersion of wax particles in which the size of the said wax particles is less than or equal to approximately 1 ⁇ m.
  • Wax microdispersions are stable dispersions of colloidal wax particles and are described in particular in "Microemulsions Theory and Practice", edited by L. M. Prince, Academic Press (1977), pages 21-32.
  • these wax microdispersions can be obtained by melting the wax in the presence of a surfactant and optionally of a portion of the water and then gradually adding hot water with stirring. The intermediate formation of an emulsion of the water- in- oil type, followed by phase inversion, with a microemulsion of oil-in-water type finally being obtained, is observed. On cooling, a stable microdispersion of solid colloidal wax particles is obtained.
  • the wax microdispersions can also be obtained by stirring the mixture of wax, of surfactant and of water using stirring means, such as ultrasound, a high pressure homogenizer or turbine mixers.
  • the particles of the wax microdispersion preferably have mean sizes of less than 1 ⁇ m (in particular ranging from 0.02 ⁇ m to 0.99 ⁇ m) , preferably of less than 0.5 ⁇ m (in particular ranging from 0.06 ⁇ m to 0.5 ⁇ m) .
  • These particles are composed essentially of a wax or of a mixture of waxes. However, they can comprise a minor proportion of oily and/or pasty fatty additives, a surfactant and/or a conventional fat-soluble additive/active principle.
  • pasty fatty substances is understood to mean a lipophilic fatty compound comprising, at a temperature of 23 0 C, a liquid fraction and a solid fraction.
  • the said pasty compound preferably has a hardness at 2O 0 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 TA-XT2i from Rheo) equipped with a stainless steel cylinder with a diameter of 2 mm.
  • the hardness measurement is carried out at 2O 0 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.
  • the value recorded for the hardness is that of the maximum peak.
  • the liquid fraction of the pasty compound measured at 23 0 C preferably represents 9 to 97% by weight of the compound.
  • This liquid fraction at 23 0 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 0 C is equal to the ratio of the enthalpy of fusion consumed at 23 0 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 1O 0 C per minute, according to Standard ISO 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 0 C is the amount of energy absorbed by the sample to change from the solid state to the state which it exhibits at 23 0 C, composed of a liquid fraction and of a solid fraction.
  • the liquid fraction of the pasty compound measured at 32 0 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 0 C.
  • the liquid fraction of the pasty compound measured at 32 0 C is equal to the ratio of the enthalpy of fusion consumed at 32 0 C to the enthalpy of fusion of the pasty compound.
  • the enthalpy of fusion consumed at 32 0 C is calculated in the same way as the enthalpy of fusion consumed at 23 0 C.
  • the pasty substances are generally hydrocarbon compounds, such as lanolins and their derivatives, or also PDMSs.
  • each first or second composition can comprise from 0.1 to 70% by weight of waxes, with respect to the total weight of the composition, better still from 1 to 60% by weight and even better still from 5 to 40% by weight.
  • the first and/or second composition can comprise a film- forming polymer.
  • film-forming polymer is understood to mean a polymer capable of forming, alone or in the presence of an additional agent which is able to form a film, a continuous film which adheres to a support, in particular to keratinous substances.
  • the film- forming polymer can be present in each composition according to the invention in a content of dry matter (or active materials) ranging from 0.1% to 30% by weight, with respect to the total weight of the composition, preferably from 0.5% to 20% by weight and better still from 1% to 15% by weight.
  • film- forming polymers which can be used in the composition of the present invention, of synthetic polymers of radical type or of polycondensate type, polymers of natural origin, and their mixtures.
  • radical film- forming polymer is understood to mean a polymer obtained by polymerization of monomers possessing unsaturation, in particular ethylenic unsaturation, each monomer being capable of homopolymerizing (unlike polycondensates) .
  • the film- forming polymers of radical type can in particular be vinyl polymers or copolymers, in particular acrylic polymers.
  • the film- forming vinyl polymers can result from the polymerization of monomers possessing ethylenic unsaturation having at least one acid group and/or of the esters of these acidic monomers and/or of the amides of these acidic monomers.
  • Use may be made, as monomer carrying an acid group, of unsaturated ⁇ , ⁇ -ethylenic carboxylic acids, such as acrylic acid, methacrylic acid, crotonic acid, maleic acid or itaconic acid. Use is preferably made of
  • esters of acidic monomers are advantageously chosen from esters of (meth) acrylic acid (also known as (meth) acrylates) , in particular alkyl (meth) acrylates, especially Ci-C 30 alkyl (meth) acrylates, preferably
  • Ci-C 2 O alkyl (meth) acrylates aryl (meth) acrylates, in particular C 6 -Ci 0 aryl (meth) acrylates, hydroxyalkyl
  • (meth) acrylates in particular C 2 -C 6 hydroxyalkyl (meth) acrylates .
  • alkyl (meth) acrylates of methyl methacrylate, ethyl methacrylate, butyl methacrylate, isobutyl methacrylate, 2-ethylhexyl methacrylate, lauryl methacrylate or cyclohexyl methacrylate .
  • hydroxyalkyl (meth) acrylates of hydroxyethyl acrylate, 2-hydroxypropyl acrylate, hydroxyethyl methacrylate or 2 -hydroxypropyl methacrylate .
  • aryl (meth) acrylates Mention may be made, among aryl (meth) acrylates, of benzyl acrylate and phenyl acrylate.
  • Esters of (meth) acrylic acid which are particularly preferred are alkyl (meth) acrylates .
  • the alkyl group of the esters can be either fluorinated or perfluorinated, that is to say that a portion or all of the hydrogen atoms of the alkyl group are substituted by fluorine atoms .
  • amides of the acidic monomers for example, of (meth) acrylamides, in particular N-alkyl (meth) acrylamides, especially
  • N-(C 2 -Ci 2 alkyl) (meth) acrylamides Mention may be made, among N-alkyl (meth) acrylamides, of N-ethylacrylamide, N- (t-butyl) acrylamide, N- (t-octyl) acrylamide and N- undecylacrylamide .
  • the film- forming vinyl polymers can also result from the homopolymerization or from the copolymerization of monomers chosen from vinyl esters and styrene monomers . In particular, these monomers can be polymerized with acidic monomers and/or their esters and/or their amides, such as those mentioned above.
  • vinyl esters of vinyl acetate, vinyl neodecanoate, vinyl pivalate, vinyl benzoate and vinyl t-butylbenzoate .
  • styrene monomers of styrene and ⁇ -methylstyrene .
  • the polyurethanes can be chosen from anionic, cationic, nonionic or amphoteric polyurethanes, polyurethane- acrylics, polyurethane-polyvinylpyrrolidones, polyester-polyurethanes, polyether-polyurethanes, polyureas, polyurea-polyurethanes, and their blends.
  • polyesters can be obtained in a known way by polycondensation of dicarboxylic acids with polyols, in particular diols.
  • the dicarboxylic acid can be aliphatic, alicyclic or aromatic. Mention may be made, as examples of such acids, of oxalic acid, malonic acid, dimethylmalonic acid, succinic acid, glutaric acid, adipic acid, pimelic acid, 2 , 2-dimethylglutaric acid, azelaic acid, suberic acid, sebacic acid, fumaric acid, maleic acid, itaconic acid, phthalic acid, dodecanedioic acid, 1 , 3-cyclohexanedicarboxylic acid, 1 , 4-cyclohexane- dicarboxylic acid, isophthalic acid, terephthalic acid, 2, 5-norbornanedicarboxylic acid, diglycolic acid, thiodipropionic acid, 2 , 5-naphthalenedicarboxylic acid or 2, 6-naphthalenedicarboxylic acid. These dicarboxylic acid monomers can be used alone or as a
  • the diol can be chosen from aliphatic, alicyclic or aromatic diols. Use is preferably made of a diol chosen from ethylene glycol, diethylene glycol, triethylene glycol, 1 , 3 -propanediol , cyclohexanedimethanol or 1, 4-butanediol . Use may be made, as other polyols, of glycerol, pentaerythritol , sorbitol or trimethylol- propane .
  • the polyesteramides can be obtained in an analogous way to the polyesters, by polycondensation of diacids with diamines or aminoalcohols .
  • Use may be made, as diamine, of ethylenediamine, hexamethylenediamine, meta- phenylenediamine or para-phenylenediamine .
  • Use may be made, as aminoalcohol, of monoethanolamine .
  • the polyester can additionally comprise at least one monomer carrying at least one -SO 3 M group, with M representing a hydrogen atom, an NH 4 + ammonium ion or a metal ion, such as, for example, an Na + , Li + , K + , Mg 2+ , Ca 2+ , Cu 2+ , Fe 2+ or Fe 3+ ion.
  • M representing a hydrogen atom, an NH 4 + ammonium ion or a metal ion, such as, for example, an Na + , Li + , K + , Mg 2+ , Ca 2+ , Cu 2+ , Fe 2+ or Fe 3+ ion.
  • Use may in particular be made of a bifunctional aromatic monomer comprising such an -SO 3 M group.
  • the aromatic nucleus of the bifunctional aromatic monomer additionally carrying an -SO 3 M group as described above can be chosen, for example, from the benzene, naphthalene, anthracene, diphenyl, oxydiphenyl , sulphonyldiphenyl or methylenediphenyl nuclei. Mention may be made, as example of bifunctional aromatic monomer additionally carrying an -SO 3 M group, of sulphoisophthalic acid, sulphoterephthalic acid, sulphophthalic acid or 4-sulphonaphthalene-2 , 7- dicarboxylic acid.
  • copolymers based on isophthalate/sulphoisophthalate and more particularly to copolymers obtained by condensation of diethylene glycol, cyclohexanedimethanol , isophthalic acid and sulphoisophthalic acid.
  • the optionally modified polymers of natural origin can be chosen from shellac resin, gum sandarac, dammars, elemis, copals, cellulose polymers and their blends.
  • the film- forming polymer can be a water-soluble polymer and can be present in an aqueous phase of the composition; the polymer is thus dissolved in the aqueous phase of the composition.
  • the film- forming polymer can be a polymer dissolved in a liquid fatty phase comprising oils or organic solvents, such as those described above (the film-forming polymer is then described as a fat-soluble polymer) .
  • the liquid fatty phase comprises a volatile oil, optionally as a mixture with a non-volatile oil, it being possible for the oils to be chosen from the oils mentioned above.
  • fat-soluble polymer of copolymers of vinyl ester (the vinyl group being directly connected to the oxygen atom of the ester group and the vinyl ester having a saturated, linear or branched, hydrocarbon radical of 1 to 19 carbon atoms bonded to the carbonyl of the ester group) and of at least one other monomer which can be a vinyl ester (other than the vinyl ester already present) , an ⁇ -olefin (having from 8 to 28 carbon atoms) , an alkyl vinyl ether (the alkyl group of which comprises from 2 to 18 carbon atoms) or an allyl or methallyl ester
  • copolymers can be crosslinked using crosslinking agents which can be either of the vinyl type or of the allyl or methallyl type, such as tetraallyloxyethane, divinylbenzene, divinyl octanedioate, divinyl dodecane- dioate and divinyl octadecanedioate .
  • crosslinking agents which can be either of the vinyl type or of the allyl or methallyl type, such as tetraallyloxyethane, divinylbenzene, divinyl octanedioate, divinyl dodecane- dioate and divinyl octadecanedioate .
  • fat-soluble film-forming polymers of fat-soluble copolymers and in particular those resulting from the copolymerization of vinyl esters having from 9 to 22 carbon atoms or of alkyl acrylates or methacrylates, the alkyl radicals having from 10 to 20 carbon atoms.
  • Such fat-soluble copolymers can be chosen from copolymers of poly (vinyl stearate) , of poly (vinyl stearate) crosslinked using divinylbenzene, diallyl ether or diallyl phthalate, copolymers of poly(stearyl (meth) acrylate) , of poly(vinyl laurate) , of poly(lauryl
  • poly (meth) acrylate (meth) acrylate) , it being possible for these poly (meth) acrylates to be crosslinked using ethylene glycol dimethacrylate or tetraethylene glycol dimethacrylate .
  • the fat-soluble copolymers defined above are known and are disclosed in particular in Application FR-A-2 232 303; they can have a weight-average molecular weight ranging from 2000 to 500 000 and preferably from 4000 to 200 000.
  • fat-soluble homopolymers in particular of those resulting from the homopolymerization of vinyl esters having from 9 to 22 carbon atoms or of alkyl acrylates or methacrylates, the alkyl radicals having from 2 to 24 carbon atoms.
  • the first composition of the process according to the invention comprises at least one poly (vinyl laurate) film-forming polymer .
  • fat-soluble film-forming polymers which can be used in the invention, of polyalkylenes and in particular copolymers of C 2 -C 2 O alkenes, such as polybutene, alkylcelluloses with a saturated or unsaturated and linear or branched Ci to C 8 alkyl radical, such as ethylcellulose and propylcellulose, copolymers of vinylpyrrolidone (VP) and in particular copolymers of vinylpyrrolidone and of C 2 to C 40 alkene and better still C 3 to C 20 alkene .
  • polyalkylenes and in particular copolymers of C 2 -C 2 O alkenes such as polybutene
  • alkylcelluloses with a saturated or unsaturated and linear or branched Ci to C 8 alkyl radical such as ethylcellulose and propylcellulose
  • VP copolymer which can be used in the invention, of the VP/vinyl acetate, VP/ethyl methacrylate, VP/ethyl methacrylate/methacrylic acid, VP/eicosene, VP/hexadecene, VP/triacontene, VP/styrene or VP/acrylic acid/lauryl methacrylate copolymer or butylated polyvinylpyrrolidone (PVP) .
  • PVP polyvinylpyrrolidone
  • silicone resins generally soluble or swellable in silicone oils, which are crosslinked polyorganosiloxane polymers.
  • the nomenclature of silicone resins is known under the name of "MDTQ” , the resin being described according to the various siloxane monomer units which it comprises, each of the letters "MDTQ” characterizing one type of unit.
  • TMS trimethylsiloxysilicate
  • silicone resins such as those mentioned above
  • polydimethylsiloxanes such as the pressure-sensitive adhesive copolymers sold by Dow Corning under the reference BIO-PSA and disclosed in the document US 5 162 410 or the silicone copolymers resulting from the reaction of a silicone resin, such as those described above, and of a diorganosiloxane, such as are disclosed in the document WO 2004/073626.
  • silicone polyamides of the polyorganosiloxane type such as those described in the documents US-A-5 874 069, US-A-5 919 441, US-A-6 051 216 and US-A-5 981 680.
  • the film- forming polymer is a film- forming linear block ethylenic polymer which preferably comprises at least one first block and at least one second block having different glass transition temperatures (Tg) , the said first and second blocks being connected to one another via an intermediate block comprising at least one constituent monomer of the first block and at least one constituent monomer of the second block.
  • Tg glass transition temperatures
  • the first and second blocks of the block polymer are incompatible with one another.
  • Such polymers are disclosed, for example, in the documents EP 1 411 069 or WO04/028488.
  • the film- forming polymer can also be present in the composition in the form of particles in dispersion in an aqueous phase or in a nonaqueous solvent phase, generally known under the name of latex or pseudolatex.
  • the techniques for the preparation of these dispersions are well known to a person skilled in the art.
  • Neocryl XK-90 ® aqueous film- forming polymer dispersion
  • Neocryl A-1070 ® aqueous film-forming polymer dispersion
  • Neocryl A-1090 ® aqueous film-forming polymer dispersion
  • Neocryl BT-62 ® aqueous film-forming polymer dispersion
  • Neocryl A-523 ® avencia Neoresins
  • Dow Latex 432 ® by Dow Chemical
  • Daitosol 5000 AD ® or Daitosol 5000 SJ ® by Daito Kasey Kogyo aqueous dispersions of acrylic or styrene/acrylic polymers
  • Joncryl ® aqueous dispersions of polyurethane
  • Neorez R- 981 ® and Neorez R-974 Avecia-Neoresins
  • Nonaqueous dispersions of film-forming polymer of acrylic dispersions in isododecane, such as Mexomer PAP ® from Chimex, dispersions of particles of a grafted ethylenic polymer, preferably an acrylic polymer, in a liquid fatty phase, the ethylenic polymer advantageously being dispersed in the absence of additional stabilizer at the surface of the particles, such as disclosed in particular in the document WO 04/055081.
  • composition according to the invention can comprise a plasticizing agent favourable to the formation of a film with the film-forming polymer.
  • a plasticizing agent can be chosen from any compound known to a person skilled in the art as being capable of fulfilling the desired role.
  • the first and second compositions employed in the method according to the invention can comprise at least one colouring material chosen, for example, from pigments, pearlescent agents, dyes, effect materials and their mixtures.
  • colouring materials can be present in a content ranging from 0.01% to 50% by weight, preferably from 0.01% to 30% by weight, with respect to the weight of each first and second composition.
  • the pigments of use in the present invention can be provided in the form of a pigment paste or powder.
  • dyes should be understood as meaning compounds, generally organic compounds, which are soluble in at least one oil or in one aqueous/alcoholic phase .
  • pigments should be understood as meaning white or coloured and inorganic or organic particles which are insoluble in the aqueous or medium and which are intended to colour and/or opacify the resulting film.
  • pearlescent agents or “pearlescent pigments” should be understood as meaning coloured particles of any shape, iridescent or noniridescent , produced in particular by certain shellfish in their shells or synthesized and which exhibit an effect of colour optical interference.
  • the pigments can be dispersed in their product by virtue of a dispersing agent.
  • the dispersing agent serves to protect the dispersed particles from the agglomeration or flocculation thereof.
  • This dispersing agent can be a surfactant, an oligomer, a polymer or a mixture of several of them carrying one or more functionalities having a strong affinity for the surface of the particles to be dispersed. In particular, they can become attached physically or chemically to the surface of the pigments.
  • These dispersants additionally exhibit at least one functional group compatible or soluble in the continuous medium.
  • esters of 12-hydroxystearic acid in particular, and of C 8 to C 2 O fatty acid and of polyol, such as glycerol or diglycerol, for example the stearate of poly (12- hydroxystearic acid) with a molecular weight of approximately 750 g/mol, such as that sold under the name of Solsperse 21 000 by Avecia, polyglyceryl-2 dipolyhydroxystearate (CTFA name) , sold under the reference Dehymyls PGPH by Henkel, or polyhydroxystearic acid, such as that sold under the reference Arlacel PlOO by Uniqema, and their mixtures.
  • polyol such as glycerol or diglycerol
  • the polydihydroxystearic acid and the esters of 12- hydroxystearic acid are preferably intended for a hydrocarbon or fluorinated medium, while the oxyethylene/oxypropylenated dimethylsiloxane mixtures are preferably intended for a silicone medium.
  • inorganic pigments of titanium dioxide, optionally treated at the surface, zirconium or cerium oxides, and also zinc, iron (black, yellow or red) or chromium oxides, manganese violet, ultramarine blue, chromium hydrate and ferric blue, and metal powders, such as aluminium powder or copper powder.
  • effect pigments such as particles comprising an organic or inorganic and natural or synthetic substrate, for example glass, acrylic resins, polyester, polyurethane, polyethylene terephthalate, ceramics or aluminas, the said substrate being or not being covered with metal substances, such as aluminium, gold, silver, platinum, copper or bronze, or with metal oxides, such as titanium dioxide, iron oxide or chromium oxide, and their mixtures.
  • the pearlescent pigments can be chosen from mica covered with titanium oxide or with bismuth oxychloride, titanium oxide-coated mica covered with iron oxides, titanium oxide-coated mica covered with in particular ferric blue or chromium oxide, titanium oxide-coated mica covered with an organic pigment of the abovementioned type, and also pearlescent pigments based on bismuth oxychloride. Use may also be made of interference pigments, in particular liquid crystal or multilayer pigments.
  • compositions according to the invention can comprise at least one filler, in particular in a content ranging from 0.01% to 50% by weight, with respect to the total weight of each composition, preferably ranging from 0.01% to 30% by weight.
  • the fillers can be inorganic or organic and of any shape, platelet, spherical or oblong, whatever the crystallographic form (for example, sheet, cubic, hexagonal, orthorhombic, and the like) .
  • talc Mention may be made of talc, mica, silica, kaolin, powders formed of polyamide (Nylon ® ) (Orgasol ® from Atochem) , of poly- ⁇ - alanine and of polyethylene, powders formed of tetrafluoroethylene polymers (Teflon ® ) , lauroyllysine, starch, boron nitride, hollow polymer microspheres, such as those of poly (vinylidene chloride) /acrylonitrile, for example Expancel ® (Nobel Industry) or of acrylic acid copolymers (Polytrap ® from Dow Corning) and silicone resin microbeads (Tospearls ® from Toshiba, for example) , particles formed of polyorganosiloxane elastomers, precipitated calcium carbonate, magnesium carbonate, basic magnesium carbonate, hydroxyapatite, hollow silica microspheres
  • compositions according to the invention can also comprise ingredients commonly used in cosmetics, such as vitamins, thickeners, lipophilic or hydrophilic gelling agents, trace elements, softeners, sequestering agents, fragrances, basifying or acidifying agents, preservatives, sunscreens, surfactants, antioxidants, fibres, care agents or their mixtures.
  • ingredients commonly used in cosmetics such as vitamins, thickeners, lipophilic or hydrophilic gelling agents, trace elements, softeners, sequestering agents, fragrances, basifying or acidifying agents, preservatives, sunscreens, surfactants, antioxidants, fibres, care agents or their mixtures.
  • the gelling agents which can be used in the compositions according to the invention can be polymeric or molecular, organic or inorganic and hydrophilic or lipophilic gelling agents.
  • inorganic lipophilic gelling agent of optionally modified clays, such as hectorites modified by a Ci 0 to C 2 2 fatty acid ammonium chloride, such as hectorite modified by distearyldimethylammonium chloride, such as, for example, that sold under the name of "Bentone 38V ® " by Elementis.
  • optionally modified clays such as hectorites modified by a Ci 0 to C 2 2 fatty acid ammonium chloride, such as hectorite modified by distearyldimethylammonium chloride, such as, for example, that sold under the name of "Bentone 38V ® " by Elementis.
  • the hydrophobic groups can be :
  • Silicas thus treated are named “Silica silylate” according to the CTFA (6th edition, 1995) . They are, for example, sold under the references “Aerosil R812 ® “ by Degussa and "Cab-O-Sil TS-530 ® " by Cabot,
  • Silicas thus treated are named “Silica dimethyl silylate” according to the CTFA (6th edition, 1995) . They are, for example, sold under the references “Aerosil R972 ® “ and “Aerosil R974 ® “ by Degussa and "Cab-O-Sil TS-610 ® “ and “Cab-O-Sil TS-720 ® " by Cabot.
  • the hydrophobic pyrogenic silica exhibits in particular a particle size which can be nanometric to micrometric, for example ranging from approximately 5 to 200 nm.
  • the polymeric organic lipophilic gelling agents are, for example, partially or completely crosslinked organopolysiloxane elastomers of three-dimensional structure, such as those sold under the names of "KSG6 ® ", “KSG16 ® “ and “KSG18 ® “ by Shin-Etsu, of "Trefil E-505C ® “ and “Trefil E-506C ® “ by Dow Corning, of "Gransil SR-CYC ® “, "SR DMF10 ® “, “SR-DC556 ® “, “SR 5CYC gel ® “, “SR DMF 10 gel ® “ and “SR DC 556 gel ® “ by Grant Industries, of "SF 1204 ® “ and of "JK 113 ® “ by General Electric; ethylcellulose, such as that sold under the name of "Ethocel ® " by Dow Chemical; galactomannans comprising from one to six and in particular from two to four hydroxyl groups per monosaccharide which are
  • lipophilic gelling agents which can be used in the compositions according to the invention, of esters of dextrin and of fatty acid, such as dextrin palmitates, in particular such as those sold under the names of "Rheopearl TL ® " or “Rheopearl KL ®” by Chiba Flour.
  • the lipophilic gelling agents can be present in the compositions according to the invention in a content ranging from 0.05 to 40% by weight, with respect to the total weight of each composition, preferably from 0.5 to 20% by weight and better still from 1 to 15% by weight .
  • hydrophilic or water-soluble gelling agent of: - homo- or copolymers of acrylic acid or methacrylic acid or their salts and their esters and in particular the products sold under the names "Versicol F” or “Versicol K” by Allied Colloid, "Ultrahold 8" by Ciba-Geigy, poly (acrylic acid) s of Synthalen K type, copolymers of acrylic acid and of acrylamide, sold in the form of their sodium salts under the "Reten" names by Hercules, poly (sodium methacrylate) , sold under the name "Darvan No.
  • Vanderbilt sodium salts of poly (hydroxycarboxylic acid)s, sold under the name "Hydagen F” by Henkel, - copolymers of poly (acrylic acid) s and of alkyl acrylates of Pemulen type,
  • AMPS poly (acrylamidomethylpropanesulphonic acid) partially neutralized with aqueous ammonia and highly crosslinked
  • Clariant - AMPS/acrylamide copolymers of Sepigel or Simugel type, sold by Seppic
  • copolymers of AMPS and of alkyl methacrylates which are polyoxyethylenated (crosslinked or noncrosslinked) , and their mixtures.
  • water-soluble gelling polymers of: proteins, such as proteins of plant origin, such as wheat or soya proteins,- proteins of animal origin, such as keratins, for example keratin hydrolysates and sulphonic keratins; anion, cationic, amphoteric or nonionic chitin or chitosan polymers; cellulose polymers, such as hydroxyethylcellulose, hydroxypropylcellulose, methylcellulose, ethylhydroxyethylcellulose, carboxymethylcellulose and quaternized cellulose derivatives; vinyl polymers, such as polyvinylpyrrolidones, copolymers of methyl vinyl ether and of malic anhydride, the copolymer of vinyl acetate and of crotonic acid, copolymers of vinylpyrrolidone and of vinyl acetate, copolymers of vinylpyrrolidone and of caprolactam, or poly (vinyl alcohol) ; - as
  • Ci 6 -OEi 20 -Ci 6 from Servo Delden (sold under the name SER AD FXIlOO, molecule comprising a urethane functional group and with a weight-average molecular weight of 1300) , OE being an oxyethylene unit, Rheolate 205 comprising a urea functional group, sold by Rheox, or also Rheolate 208 or 204 (these polymers being sold in the pure form) or DW 1206B from Rohm & Haas comprising a C 2 O alkyl chain and comprising a urethane bond, sold at a solids content in water of 20%.
  • SER AD FXIlOO molecule comprising a urethane functional group and with a weight-average molecular weight of 1300
  • Use may also be made of solutions or dispersions of these associative polyurethanes, in particular in water or in an aqueous/alcoholic medium. Mention may be made, by way of example of such polymers, of SER AD FXlOlO, SER AD FX1035 and SER AD 1070 from Servo Delden and Rheolate 255, Rheolate 278 and Rheolate 244, sold by Rheox.
  • Use may also be made of the products DW 1206F and DW 1206J, and also Acrysol RM 184 or Acrysol 44, from Rohm & Haas or alternatively Borchigel LW 44 from Borchers, optionally modified polymers of natural origin, such as : - gums arabic, guar gum, xanthan derivatives or karaya gum; alginates and carrageenans,- glycoaminoglycans, hyaluronic acid and its derivatives; - shellac resin, gum sandarac, dammars, elemis or copals; deoxyribonucleic acid; mucopolysaccharides, such as hyaluronic acid, chondroitin sulphates, and their mixtures.
  • - gums arabic, guar gum, xanthan derivatives or karaya gum alginates and carrageenans,- glycoaminoglycans, hyaluronic acid and its derivatives
  • the hydrophilic gelling agents can be present in the compositions according to the invention in a content ranging from 0.05 to 20% by weight, with respect to the total weight of each composition, preferably from 0.5 to 10% by weight and better still from 0.8 to 5% by weight .
  • the compositions according to the invention can comprise emulsifying surface-active agents present in particular in a proportion ranging from 0.1 to 30% by weight, with respect to the total weight of each composition, better still from 1 to 15% by weight and better still from 2 to 10% by weight.
  • These surface- active agents can be chosen from anionic, cationic, nonionic, amphoteric or zwitterionic surface-active agents. Reference may be made to the document "Encyclopedia of Chemical Technology, Kirk-Othmer” , volume 22, pp. 333-432, 3rd edition, 1979, Wiley, for the definition of the properties and functions
  • the surfactants preferably used in the compositions according to the invention are chosen from: a) nonionic surface-active agents with an HLB of greater than or equal to 8 to 25 0 C, used alone or as a mixture; mention may in particular be made of: oxyethylenated and/or oxypropylenated ethers (which can comprise from 1 to 150 oxyethylene and/or oxypropylene groups) of glycerol; - oxyethylenated and/or oxypropylenated ethers (which can comprise from 1 to 150 oxyethylene and/or oxypropylene groups) of fatty alcohols (in particular of C 8 -C 2 4 and preferably Ci 2 -Ci 8 alcohols) , such as the oxyethylenated ether of cetearyl alcohol comprising 30 oxyethylene groups (CTFA name "Ceteareth-30" ) and the oxyethylenated ether of the mixture of Ci 2 -Ci 5 fatty alcohols
  • nonionic surface-active agents with an HLB of less than 8 at 25 0 C optionally in combination with one or more nonionic surface-active agents with an HLB of greater than 8 at 25 0 C, such as mentioned above, such as : esters and ethers of monosaccharides, such as sucrose stearate, sucrose cocoate, sorbitan stearate and their mixtures, such as Arlatone 2121, sold by ICI; esters of fatty acids (in particular of C 8 -C 24 and preferably Ci 6 -C 22 acid) and of polyol, in particular of glycerol or of sorbitol, such as glyceryl stearate, such as the product sold under the name Tegin M by Goldschmidt, glyceryl laurate, such as the product sold under the name Imwitor 312 by H ⁇ ls, polyglyceryl-2 stearate, sorbitan tristearate or glyceryl ricinoleate,- the
  • Use is preferably made of surfactants which make it possible to obtain an oil-in-water or wax-in-water emulsion.
  • fibre should be understood as meaning an object with a length L and a diameter D such that L is much greater than D, D being the diameter of the circle in which the cross section of the fibre is framed.
  • L/D ratio or aspect ratio
  • the L/D ratio is chosen within the range from 3.5 to 2500, preferably from 5 to 500 and better still from 5 to 150.
  • the fibres can in particular be fibres used in the manufacture of textiles and in particular silk, cotton, wool or flax fibres, fibres of cellulose, in particular extracted from wood, vegetables or algae, of rayon, of polyamide (Nylon ® ) , of viscose, of acetate, in particular of rayon acetate, of poly (p-phenylene terephthalamide) (or of aramid) , in particular Kevlar ® , of acrylic polymer, in particular of poly (methyl methacrylate) or of poly (2-hydroxyethyl methacrylate) , of polyolefin in particular of polyethylene or of polypropylene, of glass, of silica, of carbon, in particular in the graphite form, of polytetrafluoroethylene (such as Teflon ® ) , of insoluble collagen, of polyesters, of poly(vinyl chloride) , of poly (vinylidene chloride), of polyvinyl alcohol, of polyacrylonitrile, of chi
  • Each of the first, second and optionally additional compositions according to the invention can be provided in particular in the form of a suspension, dispersion, solution, gel, emulsion, in particular oil-in-water (0/W) , wax-in-water or water-in-oil (W/0) or multiple (W/O/W or polyol/0/W or 0/W/O) emulsion, cream, foam, dispersion of vesicles, in particular of ionic or non- ionic lipids, two-phase or multiphase emulsion, spray, powder or paste, in particular soft paste.
  • Each composition is preferably a leave-in composition.
  • the method according to the invention can advantageously be used for making up the nails and/or skin and/or lips and/or eyelashes, depending on the nature of the ingredients used.
  • the first, second and optionally third compositions can be provided, independently, in the form of a solid foundation, lipstick stick or paste, concealer or a product for the outline of the eyes, eyeliner, mascara, eyeshadow, product for making up the body or a product for colouring the skin.
  • the first, second and optionally third compositions are lipstick compositions .
  • the first, second and optionally third compositions are compositions for coating keratinous fibres, such as the eyelashes, eyebrows or nonhead hairs, and more particularly mascaras .
  • the first, second and optionally third compositions are foundation compositions .
  • a person skilled in the art can choose the appropriate formulation, and its method of preparation, on the basis of his general knowledge, taking into account, on the one hand, the nature of constituents used, in particular their solubility in the support, and, on the other hand, the application envisaged for each composition.
  • the product is dissolved in 170 ml of DMSO, precipitated from 800 ml of water and then washed by centrifuging twice with 500 ml of water. After washing, the product is dried under vacuum and 17.6 g of a white powder are obtained.
  • the paste was dried, an excess of 2,4- dinitrofluorobenzene (2.4 ml) was added, at the same time as 10 ml of dimethylformamide, and then the mixture was stirred overnight at ambient temperature under a nitrogen atmosphere.
  • the reaction mixture was dissolved in 50 ml of DMSO and precipitated twice from a 0.1% aqueous sodium chloride solution (800 ml) to give a yellow product.
  • the product was collected, washed with water and methanol (three times, respectively) and dried to produce the polyrotaxane (1.25 g) .
  • Example 3 Preparation of a polyrotaxane functionalized by a crosslinking agent
  • Example 4 Mascara
  • the polyrotaxane is placed in the water and then the other constituents of the phase A are added.
  • phase B The constituents of the phase B (waxes, emulsifiers and premilled pigments) are heated on a water bath with stirring and then the phase A is added with rapid stirring to produce the emulsion.
  • phase B The constituents of the phase B (waxes and emulsifiers) are heated on a water bath with stirring and then the phase A is added with rapid stirring to produce the emulsion.
  • a layer of the first composition is applied to the eyelashes and then a layer of the second composition, comprising the crosslinking agent (polyethylene oxide- tetrasuccinimidyl glutarate) , is subsequently applied to the first layer.
  • the crosslinking agent polyethylene oxide- tetrasuccinimidyl glutarate
  • phase B The polyrotaxane is dissolved in the water and then the other constituents of the phase A are added.
  • the pigments are passed through a triple roll mill (phase B) .
  • phase C The constituents of the phase C are heated on a water bath at 65-7O 0 C with stirring.
  • phase A and the phase B are subsequently mixed, the phase C, still at 65-7O 0 C, is then added with rapid stirring over 10 min, to produce the emulsion, and then cooling is allowed to take place to ambient temperature.
  • a layer of the first composition is applied to the skin and then a layer of the second composition, comprising the crosslinking agent (cyanuric chloride) , is subsequently applied to the first layer.
  • the crosslinking agent cyanuric chloride
  • phase B The polyrotaxane is dissolved in the water and then the other constituents of the phase A are added.
  • the pigments are passed through a triple roll mill (phase B) .
  • phase C The constituents of the phase C are heated on a water bath at 65-7O 0 C with stirring.
  • phase A and the phase B are subsequently mixed, the phase C, still at 65-7O 0 C, is then added with rapid stirring over 10 min, to produce the emulsion, and then cooling is allowed to take place to ambient temperature .
  • the polyrotaxane is dissolved in the water at ambient temperature and the other ingredients are added.
  • a layer of the first composition is applied to the skin and then a layer of the second composition, comprising the crosslinking agent (cyanuric chloride) , is subsequently applied to the first layer.
  • a deposited layer on the skin exhibiting good hold is obtained.
  • composition which comprises noncrosslinked polyrotaxanes functionalized with a crosslinking agent, is prepared.
  • the polyrotaxane is dissolved in water at ambient temperature and then the other constituents of the phase C are added.
  • phase A The constituents of the phase A are mixed at a temperature not exceeding 25 0 C with stirring and then the pigments, passed beforehand through the triple roll mill, are added (phase B), and also the phase C, with rapid stirring, to produce the emulsion while remaining at 25 0 C.
  • the polyrotaxanes crosslink at the temperature of the skin, which makes it possible to obtain a film possessing good hold.
  • the first composition and the second composition of Example 5 above can be mixed at the time of use in proportions of 50/50 and then at least one layer of the said mixture can be applied to the skin.

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

Abstract

La présente invention concerne un procédé cosmétique de maquillage ou de soin non thérapeutique de substances kératineuses choisies parmi les ongles, la peau, les lèvres ou les cils, le procédé comprenant les étapes consistant à : a) déposer sur lesdites substances kératineuses au moins une couche d'au moins une première composition comprenant au moins un premier polyrotaxane non réticulé et au moins un second polyrotaxane non réticulé, b) soumettre ladite composition, simultanément ou à la suite de son application, au moins à un stimulus chimique, physico-chimique et/ou mécanique.
EP07788201A 2006-08-04 2007-08-03 Procédé de maquillage ou de soin de substances kératineuses avec des polyrotaxanes non réticulés Withdrawn EP2049076A1 (fr)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
FR0653297A FR2904534B1 (fr) 2006-08-04 2006-08-04 Procede de maquillage ou de soin des matieres keratiniques avec polyrotaxanes non reticule
US83694706P 2006-08-11 2006-08-11
PCT/EP2007/058067 WO2008015272A1 (fr) 2006-08-04 2007-08-03 Procédé de maquillage ou de soin de substances kératineuses avec des polyrotaxanes non réticulés

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EP2049076A1 true EP2049076A1 (fr) 2009-04-22

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FR2908307B1 (fr) 2006-11-10 2009-05-01 Oreal Composition cosmetique comprenant un phosphate d'alkyle et un ether d'alcool gras et de polyethyleneglycol, procedes et utilisations.
JP5470246B2 (ja) * 2008-05-07 2014-04-16 アドバンスト・ソフトマテリアルズ株式会社 ポリロタキサン、及びポリロタキサンとポリマーとの架橋体、並びにこれらの製造方法
FR2947726A1 (fr) * 2009-07-07 2011-01-14 Oreal Procede de lissage de la peau par comblement de portions en creux
FR2947725A1 (fr) * 2009-07-07 2011-01-14 Oreal Procede de lissage de la peau par comblement de portions en creux
FR2954141B1 (fr) * 2009-12-18 2012-04-13 Oreal Procede pour capter des actifs dans la peau
FR2954142B1 (fr) * 2009-12-18 2012-04-13 Oreal Procede de traitement cosmetique impliquant un compose apte a condenser in situ
WO2018012484A1 (fr) * 2016-07-13 2018-01-18 積水化学工業株式会社 Particules composites et dispositif d'affichage à cristaux liquides

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JP3565975B2 (ja) * 1996-02-08 2004-09-15 株式会社ノエビア 皮膚外用剤
JPH09315937A (ja) * 1996-03-25 1997-12-09 Shiseido Co Ltd ゲル化組成物、乳化組成物及び皮膚外用剤
DE60139683D1 (de) * 2000-04-28 2009-10-08 Toudai Tlo Ltd Verbindung enthaltend vernetzte polyrotaxane

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See references of WO2008015272A1 *

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