WO2014095426A1 - Composition permettant la libération d'un agent bénéfique comprenant un polycondensat de cyclodextrine insoluble dans l'eau et au moins un agent bénéfique - Google Patents

Composition permettant la libération d'un agent bénéfique comprenant un polycondensat de cyclodextrine insoluble dans l'eau et au moins un agent bénéfique Download PDF

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Publication number
WO2014095426A1
WO2014095426A1 PCT/EP2013/075813 EP2013075813W WO2014095426A1 WO 2014095426 A1 WO2014095426 A1 WO 2014095426A1 EP 2013075813 W EP2013075813 W EP 2013075813W WO 2014095426 A1 WO2014095426 A1 WO 2014095426A1
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Prior art keywords
acid
cyclodextrin
polycondensate
carbon atoms
anhydride
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PCT/EP2013/075813
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English (en)
Inventor
Gérard Malle
Tiina Luukas
Laurent SABATIE
Julien PORTAL
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L'oreal
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Publication of WO2014095426A1 publication Critical patent/WO2014095426A1/fr

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    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q13/00—Formulations or additives for perfume preparations
    • 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
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00—Preparations for care of the skin
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08B—POLYSACCHARIDES; DERIVATIVES THEREOF
    • C08B11/00—Preparation of cellulose ethers
    • C08B11/02—Alkyl or cycloalkyl ethers
    • C08B11/04—Alkyl or cycloalkyl ethers with substituted hydrocarbon radicals
    • C08B11/08—Alkyl or cycloalkyl ethers with substituted hydrocarbon radicals with hydroxylated hydrocarbon radicals; Esters, ethers, or acetals thereof
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08B—POLYSACCHARIDES; DERIVATIVES THEREOF
    • C08B37/00—Preparation of polysaccharides not provided for in groups C08B1/00 - C08B35/00; Derivatives thereof
    • C08B37/0006—Homoglycans, i.e. polysaccharides having a main chain consisting of one single sugar, e.g. colominic acid
    • C08B37/0009—Homoglycans, i.e. polysaccharides having a main chain consisting of one single sugar, e.g. colominic acid alpha-D-Glucans, e.g. polydextrose, alternan, glycogen; (alpha-1,4)(alpha-1,6)-D-Glucans; (alpha-1,3)(alpha-1,4)-D-Glucans, e.g. isolichenan or nigeran; (alpha-1,4)-D-Glucans; (alpha-1,3)-D-Glucans, e.g. pseudonigeran; Derivatives thereof
    • C08B37/0012—Cyclodextrin [CD], e.g. cycle with 6 units (alpha), with 7 units (beta) and with 8 units (gamma), large-ring cyclodextrin or cycloamylose with 9 units or more; Derivatives thereof
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08B—POLYSACCHARIDES; DERIVATIVES THEREOF
    • C08B37/00—Preparation of polysaccharides not provided for in groups C08B1/00 - C08B35/00; Derivatives thereof
    • C08B37/0006—Homoglycans, i.e. polysaccharides having a main chain consisting of one single sugar, e.g. colominic acid
    • C08B37/0009—Homoglycans, i.e. polysaccharides having a main chain consisting of one single sugar, e.g. colominic acid alpha-D-Glucans, e.g. polydextrose, alternan, glycogen; (alpha-1,4)(alpha-1,6)-D-Glucans; (alpha-1,3)(alpha-1,4)-D-Glucans, e.g. isolichenan or nigeran; (alpha-1,4)-D-Glucans; (alpha-1,3)-D-Glucans, e.g. pseudonigeran; Derivatives thereof
    • C08B37/0012—Cyclodextrin [CD], e.g. cycle with 6 units (alpha), with 7 units (beta) and with 8 units (gamma), large-ring cyclodextrin or cycloamylose with 9 units or more; Derivatives thereof
    • C08B37/0015—Inclusion compounds, i.e. host-guest compounds, e.g. polyrotaxanes
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L5/00—Compositions of polysaccharides or of their derivatives not provided for in groups C08L1/00 or C08L3/00
    • C08L5/16—Cyclodextrin; Derivatives thereof
    • 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
    • A61K2800/10—General cosmetic use
    • 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
    • A61K2800/56—Compounds, absorbed onto or entrapped into a solid carrier, e.g. encapsulated perfumes, inclusion compounds, sustained release forms

Definitions

  • the present invention relates to a composition which makes possible the release of a beneficial agent comprising at least one beneficial agent and a support comprising at least one water-insoluble cyclodextrin polycondensate, it being possible for said cyclodextrin polycondensate to be obtained by esterification/polycondensation reaction:
  • Another subject-matter of the invention consists of a consumer product comprising at least one composition which makes possible the release of a beneficial agent as defined previously, in particular a cosmetic or dermatological composition comprising a physiologically acceptable medium.
  • the invention relates to a process for cosmetic treatment of a keratin material, consisting in applying, to the surface of said human keratin material, a consumer product comprising a composition as defined above containing, in a physiologically acceptable medium, at least one beneficial agent chosen from cosmetic active agents.
  • the objective of the present invention is to search for new materials which make it possible to trap at least one beneficial agent and to delay its time for release to the exterior for the purpose of:
  • fragrances fragranced essences, essential oils, bleaching agents, insecticides, colorants, lipids, silicones, waxes, flavourings, enzymes, oxidizing agents, microorganisms, phytosanitary active agents, food additives such as flavour enhancers, textile softeners, antibacterials, cooling agents, active ingredients of medicaments, and cosmetic or dermatological active agents.
  • Such beneficial agents are generally expensive and/or volatile and/or physicochemically unstable and/or effective over periods of time which are too short. There is therefore a need to optimize their amount in order to limit costs, to improve their stability, to protect them against their environment and/or to improve their effectiveness over time.
  • One of the means known from the prior art for achieving these objectives is the microencapsulation of these substances. In addition to the advantages previously mentioned, this encapsulation can also make it possible to render the material easier to use by diluting it and by promoting its homogeneous distribution within the support.
  • Microencapsulation groups together all the technologies for coating or trapping substances in solid, liquid or gas form within individualized particles, the size of which ranges between a few microns and a few millimetres. If these microparticles are hollow (vesicular) they are referred to as microcapsules, and if they are solid (matricial) they are referred to as microspheres. Their size ranges from 1 m to more than 1000 pm. These microparticles can be biodegradable or non-biodegradable and can contain between 5% and 90% (by weight) of encapsulated substance.
  • the encapsulated substances are very varied in origin: pharmaceutical active ingredients, cosmetic active ingredients, food additives, phytosanitary products, fragranced essences, microorganisms, cells, or else chemical reaction catalysts, etc.
  • microbeads consisting of hydrophobic polymeric materials which are generally prepared by phase separation techniques (coacervation or solvent extraction-evaporation) or by polymerization or polycondensation are also known.
  • phase separation techniques generally use organic solvents which have a certain number of drawbacks: elimination into the atmosphere, persistence within galenical systems, denaturation of certain microencapsulated molecules.
  • the methods by polymerization or polycondensation that are known to date have the drawback of using highly reactive materials capable of reacting with the substances encapsulated within the microbeads.
  • Microbeads formed from hydrophilic polymeric materials which are generally prepared by gelling or coacervation techniques are also known from the prior art. This technique which makes it possible to encapsulate molecules in liquid or solid form is based on the desolvation of macromolecules, resulting in phase separation within a solution.
  • encapsulation in lipid materials the technique of microencapsulation by thermal gelling is known. This process, known as hot melt, is based on melting the coating material. The substance to be encapsulated is dissolved or dispersed in this molten material. The mixture is emulsified in a dispersing phase, the temperature of which is kept above the melting point of the coating. The solidification of the dispersed globules is obtained by abruptly cooling the medium.
  • molecular encapsulation cyclodextrins
  • the latter constitutes an advantageous alternative to the conventional encapsulations described above.
  • Cyclodextrins have in fact been increasingly used for this purpose since the 1980s since they are cage molecules which can selectively and reversibly complex a large diversity of organic molecules in the form of "host-guest" inclusion complexes. Cyclodextrin inclusion complexes are particularly useful for transporting, protecting and releasing chemically and thermally sensitive ingredients. The release of the complexed ingredients is generally brought about via water or temperature.
  • Cyclodextrins are a family of natural cyclic oligosaccharides obtained by enzymatic degradation of starch. They consist of alpha-D-glucose units (6 to 12 units) linked to one another so as to form rings delimiting in their centre a frustum-shaped cavity.
  • hexamers a-cyclodextrin
  • heptamers ⁇ -cyclodextrin
  • octamers ⁇ -cyclodextrin
  • All the hydroxyl (OH) polar groups are located on the exterior, making the exterior hydrophilic and explaining their solubility in water. Since the interior of the cavity contains only the glycosidic oxygen atoms and the hydrogen atoms directly bonded to the carbons, said cavity is hydrophobic and considerably less polar.
  • cyclodextrins This amphiphilic nature enables cyclodextrins to include in their cavity lipophilic (hydrophobic) molecules, provided that the size and the geometric shape of the molecules lend themselves thereto, so as to form inclusion complexes which are generally water- soluble.
  • Their non-toxic and biodegradable nature predisposes them to important applications in the food-processing and pharmaceutical fields.
  • the encapsulation in cyclodextrins in fact makes it possible to protect fragile molecules or to provide the slow and controlled release thereof.
  • solubilization of water-insoluble medicaments in the form of inclusion complexes in cyclodextrins makes it possible to have injectable preparations.
  • Native cyclodextrins can be chemically modified, for example to give ethers or esters, which will modify the solubility both of the modified cyclodextrins and of the inclusion complexes. Many advantages follow from this and allow cyclodextrins to be widely used in various industrial fields.
  • Cyclodextrins are also commonly used as a formulation excipient in medicaments. They make it possible in particular to convert liquid compounds into solids (powders, tablets) by inclusion complex precipitation.
  • the complexation of the active ingredients makes it possible to have better control of their passage into the bloodstream or the progressivity of their diffusion. Another application is sublingual treatment.
  • the complexation of photosensitive or highly reactive active ingredients often makes it possible to protect them or to stabilize them.
  • cyclodextrins as taste enhancers, allowing easy addition of taste compounds, or for fixing molecules that are too volatile and prolonging, for example, the taste duration of chewing gums. They are also used, on the contrary, for removing certain undesirable molecules, in particular for reducing the levels of cholesterol or of bitter compounds of ready meals or else as masking agents against bad odours. Cyclodextrins are also used for stabilizing emulsions such as mayonnaise or margarines.
  • the inclusion will depend on the relative size of the cavity of the cyclodextrin relative to the size of the guest molecule; if said molecule is too large, it will not be able to penetrate inside the cavity of the cyclodextrin and if, on the other hand, its size is too small, it will have few interactions with the cyclodextrin.
  • the steric effect therefore plays an important role in the complexation phenomenon.
  • the cyclodextrin:guest molecule molar ratio of the inclusion complexes is generally 1:1 or higher; in other words, at most one molecule is transported per cyclodextrin molecule.
  • primary alcohols have been substituted with monosaccharide or oligosaccharide groups, on the one hand so as to improve their water-solubility and, on the other hand, so as to incorporate cell recognition signals into their structure (international applications PCT WO 95/19994, WO 95/21870 and WO 97/33919).
  • the cyclodextrin derivatives of the prior art can have certain limitations, in particular with respect to the substances that may be transported, to the substance load capacity per unit weight of the cyclodextrin derivative, to their capacity to complex certain families of molecules, in particular hydrophilic molecules, to their cost, to their toxicity, and to the ease with which they can be synthesized.
  • cyclodextrin polymers which have polymer- substrate complex stability constants that are often higher than those of native cyclodextrin-substrate complexes, and for which the hydrophobic and hydrophilic compounds and the supramolecules are more readily complexed and less readily released by the cyclodextrin polymers than by the native cyclodextrins.
  • cyclodextrin polymers can be categorized into two types depending on whether the cyclodextrin constitutes the backbone of the polymer or else is a side substituent of a polymer chain.
  • the methods for synthesizing these prior art cyclodextrin polymers, the cyclodextrin of which constitutes the backbone, are based on the use of generally bifunctional crosslinking agents, such as epichlorohydrin, dialdehydes, diacids, diesters, diisocyanates, dihalogenated derivatives, polyisocyanates, bis-epoxides, acid dihalides in an organic solvent or else phytic acid.
  • generally bifunctional crosslinking agents such as epichlorohydrin, dialdehydes, diacids, diesters, diisocyanates, dihalogenated derivatives, polyisocyanates, bis-epoxides, acid dihalides in an organic solvent or else phytic acid.
  • a process using a bifunctional agent such as a dialdehyde, a diacid, a diester, an acid dichloride, a diepoxide, a diisocyanate or a dihalogenated derivative has been described in document US 3 472 835.
  • This method envisages the activation of cyclodextrins via the action of sodium metal in liquid aqueous ammonia and then reaction with the bifunctional crosslinking agent.
  • the second type of polymer is that in which the cyclodextrin is a pendent group of a polymer chain; it is produced by grafting cyclodextrin(s) or cyclodextrin derivative(s) onto a pre-existing polymer chain.
  • DE19520989 describes the grafting of cyclodextrins onto cellulose polymers via halotriazine and halopyrimidine derivatives.
  • cyclodextrins have also been functionalized with aldehyde groups and then grafted onto chitosan via a reductive amination reaction; such a reaction is described by Tomoya T. et al. in J. Polym. Sci., Part A: Polym. Chem. 36 (11), 1965-1968 (1998).
  • These cyclodextrin-based polymers can also be synthesized by functionalization of said cyclodextrin with polymerizable functional groups such as acryloyl or methacryloyl.
  • WO0148025 Korean in the application WO0148025 (Kimberly Klarck) is a method of a preparation of a composition which consists to react a cyclodextrine on a polysaccharide for example cellulose fibers by crosslinking with a reactive anionic polymer in forming esters bounds between each other.
  • the reactive anionic polymer comprises functional anionic groups as a cyclic acid anhydride like maleic acid anhydride and may react with a catalyst in particular with sodium hypophosphite.
  • the reactive anionic polymer as used in the examples is a terpolymer of maleic anhydride/vinylacetate/ethylacetate BELCLENE DP80® (Durable Press 80).
  • the cyclodextrin polycondensate as formed has a weak encapsulation capacity of a beneficial active ingredient like a perfume and the time of release is insufficiently long.
  • the objective of the present invention is to immobilize cyclodextrins in a crosslinked polymeric network having absorbent properties and functioning like a sponge.
  • the present invention relates to a composition which makes possible the release of a beneficial agent comprising at least one beneficial agent and a support comprising at least one water-insoluble cyclodextrin polycondensate which can be obtained by esterification/polycondensation reaction:
  • Another subject of the invention consists of a consumer product comprising at least one composition which makes possible the release of a beneficial agent as defined previously.
  • the consumer product relates to a cosmetic or dermatological composition comprising a physiologically acceptable medium.
  • the invention relates to a process for cosmetic treatment of a keratin material, consisting in applying, to the surface of said human keratin material, a consumer product comprising a composition as defined above containing, in a physiologically acceptable medium, at least one beneficial agent chosen from cosmetic active agents.
  • polycondensate is intended to mean any polymer obtained by polymerization in steps where each step is a condensation reaction which is carried out with elimination of water or of an alcohol or of a halogenated acid in the case of an esterification.
  • Monomers with two or more functional groups react so as to first form dimers, then trimers and longer oligomers, then long-chain polymers.
  • water-insoluble cyclodextrin polycondensate is intended to mean any cyclodextrin polycondensate which has a solubility in water at 25°C of less than 1% by weight, even less than 0.5% by weight, or even less than 0.1% by weight.
  • physiologically acceptable medium is intended to mean a medium that is suitable for the topical administration of a composition.
  • a physiologically acceptable medium is preferably a cosmetically or dermatologically acceptable medium, that is to say a medium which is devoid of unpleasant odour or appearance and which is entirely compatible with the topical administration route.
  • keratin materials is intended to mean the skin, hides, the scalp, the lips, and/or the skin appendages such as the nails and keratin fibres, such as, for example, animal furs, body hair, wool, the eyelashes, the eyebrows and the hair.
  • human keratin materials is intended to mean the skin, the scalp, the lips, and/or the skin appendages such as the nails and human keratin fibres, such as, for example, body hair, the eyelashes, the eyebrows and the hair.
  • cosmetic composition is intended to mean any composition which has a non-therapeutic hygiene, care, conditioning or makeup effect contributing to improving the well- being and/or to making more attractive and/or modifying the appearance of the keratin material to which said composition is applied.
  • consumer product is intended to mean any manufactured product intended to be used or consumed in the form in which it is sold and which is not intended for subsequent manufacture or modification.
  • the consumer products according to the invention may be cosmetic products including both cosmetic formulations and application supports or articles comprising such formulations, such as patches, wipes, nonwoven supports; intimate hygiene products including care and hygiene formulations and also articles intended for this purpose, such as sanitary tampons, wipes, towels; products for oral hygiene, such as toothpastes, mouth care products, deodorants such as sprays, breath lozenges, chewing gums, sweets; cosmetic or dermatological products: creams, milks, lotions, balms, sticks, talcs; makeup products; hair products; babycare products including formulations and articles intended for this purpose, such as wipes, nappies; pharmaceutical products and also medical and paramedical articles such as dressings, patches, prostheses; products for veterinary use, such as animal litters; animal hygiene and/or care products; household products such as laundry care and/or
  • the term "beneficial agent” is intended to mean any chemical compound present in a consumer product which produces a beneficial effect noticed by the consumer during use thereof and/or obtained on the consumer product itself, it being possible for said beneficial effect to be a sensory improvement or a modification, in particular a visual and/or olfactory and/or gustative and/or tactile improvement, an improvement of the comfort and/or ease of application, an aesthetic effect, a hygiene effect, a feeling of cleanliness, a curative and/or prophylactic effect.
  • composition which makes possible the release of a beneficial agent is intended to mean a composition comprising at least one beneficial agent immobilized, captured and/or encapsulated, in part or completely, in the matrix of an encapsulating or trapping system, said beneficial agent being released towards the outside as the encapsulating or trapping system deteriorates when the degradation thereof occurs on contact with a medium with which it will react or under the effect of a stimulus, such as a rise in the temperature by contributing heat, a contribution of water or any other constituent or mixture of constituents capable of being complexed in a more stable fashion than the encapsulated beneficial agent.
  • the cyclodextrin polycondensates according to the invention can be easily prepared, in a single synthesis step, and without producing waste, at low cost, in particular by carrying out the reaction in an extruder. Moreover, it is easily possible to modify the structure and/or the properties of the cyclodextrin polycondensates according to the invention, by varying the chemical nature of the various constituents and/or the proportions thereof.
  • the cyclodextrin polycondensates according to the invention make it possible to generate a porous polymeric network which combines sponge- type superabsorbent properties with the capacity to form inclusion complexes in the cavities of cyclodextrins immobilized within the polymeric network.
  • the cyclodextrin polycondensates according to the invention can be obtained by esterification/polycondensation, according to methods known to those skilled in the art, of the constituents described hereinafter.
  • One of the constituents required for the preparation of the cyclodextrin polycondensates according to the invention is a cyclodextrin.
  • cyclodextrin is intended to mean any compound of general structure
  • cyclodextrins or derivatives thereof which are preferred, mention may be made of a-cyclodextrin, ⁇ -cyclodextrin, ⁇ -cyclodextrin, and methylated derivatives thereof such as TRIMEBs (heptakis(2,3,6- trimethyl)-3-CD), DIMEBs (heptakis(2,6-dimethyl)-3-CD) or else RAMEBs (Randomly Methylated ⁇ -Cyclodextrins); hydroxyalkylated derivatives thereof such as 2-hydroxypropyl-3-cyclodextrin ( ⁇ ; Kleptose® HPB), 3-hydroxypropyl-3-cyclodextrin, 2,3-dihydroxypropyl-3-cyclodextrin, 2-hydroxyethyl-3-cyclodextrin, 2-hydroxypropyl-Y-cyclodextrin and 2-hydroxyethyl-Y-cyclodextrin; sulfobutylated
  • the cyclodextrin is chosen from a-cyclodextrin, ⁇ -cyclodextrin, ⁇ -cyclodextrin and mixtures thereof, and even better still ⁇ -cyclodextrin.
  • the cyclodextrin(s) preferably represent(s) 10% to 70% by weight, in particular 20% to 65% by weight and better still 30% to 60% by weight of the total weight used in the synthesis of the cyclodextrin polycondensate.
  • Another constituent required for the preparation of the cyclodextrin polymers according to the invention is a saturated or unsaturated or aromatic, linear or branched or cyclic polycarboxylic acid comprising at least 2 carboxylic COOH groups, preferably 2 to 4 COOH groups.
  • Said polycarboxylic acid may in particular be chosen from saturated or unsaturated, or even aromatic, linear, branched and/or cyclic polycarboxylic acids containing 2 to 50 carbon atoms, especially 2 to 40, in particular 3 to 36 carbon atoms, or even 3 to 18 and even better still 4 to 12 carbon atoms, or even 4 to 10 carbon atoms; said acid comprises at least two carboxylic COOH groups and preferably from 2 to 4 COOH groups.
  • polycarboxylic acids that may be used, mention may be made, alone or as a mixture, of:
  • - icarboxylic acids such as oxalic acid, malonic acid, succinic acid, glutaric acid, adipic acid, pimelic acid, suberic acid, azelaic acid, sebacic acid, dodecanedioic acid, malic acid, tartaric acid, tartronic acid, citramalic acid, dioxymaleic acid, dioxymalonic acid, maleic acid, fumaric acid, glutaconic acid, itaconic acid, fatty acid (in particular C 3 6 fatty acid) dimers, such as the products sold under the names Pripol 1006, 1009, 1013 and 1017 by Uniqema, glutamic acid, aspartic acid, oxaloacetic acid, cyclopropanedicarboxylic acid, cyclohexanedicarboxylic acid, cyclobutanedicarboxylic acid, naphthalene-1 ,4-dicarboxylic acid, naphthalene-2,3-dica
  • - tricarboxylic acids such as citric acid, aconitic acid, isocitric acid, oxalosuccinic acid, 1 ,2,3-propanetricarboxylic acid, 1 ,2,5-pentane- tricarboxylic acid, 1 ,3,5-pentanetricarboxylic acid, transaconitic acid, 3-butene-1 ,2,3-tricarboxylic acid, 3-butene-1 , 1 ,3-tricarboxylic acid, 1,3,5- cyclohexanetricarboxylic acid, trimellitic acid, 1 ,2,3-benzenetricarboxylic acid or 1 ,3,5-benzenetricarboxylic acid;
  • - tetracarboxylic acids such as 1 ,2,3,4-butanetetracarboxylic acid, pyromellitic acid, oxydisuccinic acid, thiodisuccinic acid, N-[1,2- dicarboxyethyl]-L-aspartic acid, ethylenediaminetetraacetic acid, ethylenediaminetetrapropionic acid or N,N'-ethylenedi(L-aspartic) acid.
  • said polycarboxylic acid used alone or as a mixture, is aliphatic, saturated and linear and contains 2 to 36 carbon atoms, in particular 3 to 18 carbon atoms, or even 4 to 12 carbon atoms; or alternatively is aromatic and contains 8 to 12 carbon atoms. It preferably comprises 2 to 4 COOH groups.
  • citric acid aconitic acid, tartaric acid, 1 ,2,3-propanetricarboxylic acid and 1 ,2,3,4-butanetetracarboxylic acid, alone or as a mixture, preferably alone, and even better still citric acid alone.
  • aconitic acid tartaric acid
  • 1 ,2,3-propanetricarboxylic acid 1 ,2,3,4-butanetetracarboxylic acid
  • polycarboxylic acid ester derivatives mention may be made of the C1-C4 alkyl mono-, di-, tri- or tetraesters, in particular the methyl, ethyl, isopropyl or n-butyl esters and more preferentially the methyl or ethyl esters.
  • the preferred polycarboxylic acid esters are the methyl, ethyl, isopropyl or n-butyl esters and more preferentially the methyl or ethyl esters of aliphatic, saturated, linear polyacids (2 to 4 COOH groups) containing 2 to 36 carbon atoms, in particular 3 to 18 carbon atoms, or even 4 to 12 carbon atoms; or alternatively of an aromatic acid containing 8 to 12 carbon atoms.
  • methyl, ethyl, isopropyl or n-butyl esters and more preferentially the ethyl or butyl esters of citric acid, of aconitic acid, of tartaric acid, of 1 ,2,3-propanetricarboxylic acid and of 1 ,2,3,4-butanetetracarboxylic acid, alone or as a mixture, and even better still the ethyl or butyl esters of citric acid, such as triethyl citrate, triethyl acetylcitrate, tributyl citrate and tributyl acetylcitrate.
  • Polycarboxylic acid anhydrides such as triethyl citrate, triethyl acetylcitrate, tributyl citrate and tributyl acetylcitrate.
  • polycarboxylic acid-derived acid anhydrides mention may be made of mixed anhydrides with a C 2 -C 4 carboxylic acid (acetic, propionic or butyric acid), preferably acetic acid. Mention may also be made of cyclic anhydrides of polycarboxylic acids, such as phthalic anhydride, trimellitic anhydride, maleic anhydride, succinic anhydride or ⁇ , ⁇ , ⁇ ', ⁇ '- ethylenediaminetetraacetic acid dianhydride. Preferably, the polycarboxylic acid anhydride, alone or as a mixture, is chosen from maleic anhydride and succinic anhydride and more preferentially is maleic anhydride alone. d) Polycarboxylic acid halides
  • the acid halides derived from said polycarboxylic acids mention may be made of the acid chlorides or acid bromides of said polycarboxylic acids, preferably the polycarboxylic acid chlorides.
  • the acid halides used alone or as a mixture, are derivatives of aconitic acid, of tartaric acid, of 1 ,2,3-propanetricarboxylic acid and of 1 ,2,3,4-butanetetracarboxylic acid.
  • Said polycarboxylic acid(s) and/or ester, acid anhydride or acid halide derivatives thereof, used alone or as a mixture, preferably represent(s) 5% to 40% by weight, more preferentially from 7% to 35% by weight and better still 10% to 30% by weight, of the total weight used in the synthesis of the cyclodextrin polycondensate.
  • thermoplastic polyol polymer Another constituent required for the preparation of the cyclodextrin polycondensates according to the invention is a thermoplastic polyol polymer.
  • polyol polymer is intended to mean a polymer having an average molecular weight ranging from 1000 to 200 000 Daltons, containing at least two hydroxyl functions.
  • thermoplastic polyol polymer is intended to mean a polyol polymer which fluidifies (softens) in heat at a temperature between 100 and 250°C.
  • thermoplastic polyol polymers can be used according to the invention. Mention will be made of polyether-polyols, polyester- polyols, polycarbonate-polyols, polyamide-polyols, polyurethane-polyols, polyalkylene-polyols, polycaprolactone-polyols and polysaccharides.
  • polyether-polyols mention will be made of polyoxyethylene glycols, polyoxypropylene glycols, block or random copolymers of ethylene oxide and of propylene oxide, block or random copolymers of ethylene oxide and/or propylene oxide with tetrahydrofuran, and more particularly polytetramethylene glycols and polypropylene glycols.
  • polyester-polyols mention will in particular be made of those obtained by polycondensation of dicarboxylic or tricarboxylic acids with polyols (di-, tri- or tetraols), for instance poly(hexamethylene adipate), and also those obtained by polycondensation of hydroxy acids, such as polyhydroxyalkanoates and in particular polylactic acid, polyhydroxybutyrate (PHB) and polyhydroxybutyrate-valerate (PHBV).
  • polyols di-, tri- or tetraols
  • hydroxy acids such as polyhydroxyalkanoates and in particular polylactic acid, polyhydroxybutyrate (PHB) and polyhydroxybutyrate-valerate (PHBV).
  • polycarbonate-polyols examples include those prepared by reacting diols (propane-1 ,3-diol, butane-1 ,4-diol, hexane-1 ,6-diol, 1,9- nonanediol, 2-methyloctane-1 ,8-diol, diethylene glycol, etc.) with diaryl carbonates, such as diphenyl carbonate, or else with phosgene.
  • diols propane-1 ,3-diol, butane-1 ,4-diol, hexane-1 ,6-diol, 1,9- nonanediol, 2-methyloctane-1 ,8-diol, diethylene glycol, etc.
  • diaryl carbonates such as diphenyl carbonate, or else with phosgene.
  • polyamide-polyols mention will be made more particularly of those obtained by reacting a diamine and/or a polymeric diamine with a dicarboxylic or polycarboxylic acid and a hydroxy acid, such as, for example, 12-hydroxystearic acid.
  • a polyaddition process consisting in reacting polyisocyanates, preferably diisocyanates, with diols and/or polyols.
  • polycaprolactone-polyols obtained by polymerization of epsilon- caprolactone with ring opening via polyols such as ethylene glycol, 1,2- propanediol, 1 ,3-propanediol, glycerol or trimethylolpropane.
  • polyvinyl alcohol modified polyvinyl alcohol having a content of ethylene units of 4 mol% to 15 mol% and polybutadiene diols.
  • thermoplastic starches which are obtained by destructuring the native granule in the presence of a plasticizer under thermomechanical stresses; cellulose derivatives, such as cellulose acetate, cellulose acetobutyrate, cellulose acetopropionate, methylcellulose, ethylcellulose, hydroxypropylcellulose, hydroxyethylcellulose, hydroxy propyl methyl- cellulose, hydroxyethylmethylcellulose or carboxymethylcellulose, alone or as a mixture with alginates, gums such as guar gum, starches such as tapioca starch, modified starches such as starch octenyl succinate (E.1450), oxidized starches (E.1404), crosslinked starches (E.1412 or 1413), stabilized starches (E.1420 or E.1440), crosslinked/stabilized starches such as acetylated distarch adipate (E.1422) or hydroxypropylated dist
  • cellulose derivatives such as cellulose acetate,
  • thermoplastic polyol polymers which can be used for the preparation of the cyclodextrin polycondensates
  • the polysaccharides are particularly preferred since they have a renewable origin and are available at high tonnage and at low cost.
  • thermoplastic polyol polymer(s) preferably represent(s) 10% to 50% by weight, in particular 15% to 45% by weight and better still 17% to 40% by weight, of the total weight used in the synthesis of the cyclodextrin polycondensate.
  • At least one polycarboxylic acid cyclic anhydride chosen so as to be other than the first polycarboxylic acid anhydride previously mentioned is also used for the preparation of the cyclodextrin polycondensates according to the invention.
  • the polycarboxylic acid cyclic anhydride may in particular correspond to one of the following formulae:
  • a and B taken together, form a saturated or unsaturated, or even aromatic, ring containing in total 5 to 7 and in particular 6 carbon atoms.
  • a and B represent a hydrogen atom or together form an aromatic ring containing in total 6 carbon atoms.
  • polycarboxylic acid cyclic anhydrides which may be used, mention may be made of, alone or as a mixture, phthalic anhydride, trimellitic anhydride, maleic anhydride and succinic anhydride.
  • use may be made of maleic anhydride and succinic anhydride alone or as a mixture, and even better still maleic anhydride alone.
  • polycarboxylic acid cyclic anhydride When said polycarboxylic acid cyclic anhydride is present among the ingredients used, it preferably represents 0.1% to 10% by weight, in particular 0.5% to 5% by weight, or even 0.7% to 4% by weight, relative to the total weight used in the synthesis of the cyclodextrin polycondensate.
  • At least one esterification catalyst will be used for the preparation of the cyclodextrin polycondensates according to the invention.
  • the esterification catalyst may in particular be chosen from dihydrogen phosphates, hydrogen phosphates, phosphates, hypophosphites and phosphites of alkali metals, alkali metal salts of polyphosphoric acids, alkali metal or alkaline-earth metal carbonates, bicarbonates, acetates, borates and hydroxides, aliphatic amines and aqueous ammonia, optionally combined with an inorganic solid support such as alumina, silica gels, Al silicates, zeolites, titanium oxides or zirconium oxides.
  • the esterification catalyst may also be chosen from sulfonic acids or titanates.
  • Use may preferably be made of sodium hydrogen phosphate, sodium dihydrogen phosphate and sodium hypophosphite.
  • esterification catalyst when present among the ingredients used, it preferably represents 0.1% to 5% by weight, in particular 0.5% to 4% by weight, or even 0.5% to 3% by weight, relative to the total weight used in the synthesis of the cyclodextrin polycondensate.
  • At least one non- polymeric polyol comprising 3 to 6 hydroxyl groups will also be used for the preparation of the cyclodextrin polycondensates according to the invention.
  • a mixture of such polyols may obviously be used.
  • Said polyol may in particular be a linear, branched and/or cyclic, saturated or unsaturated carbon-based and in particular hydrocarbon-based compound containing 3 to 18 carbon atoms, in particular 3 to 12 or even 4 to 10 carbon atoms, and 3 to 6 hydroxyl (OH) groups, and also possibly comprising one or more oxygen atoms inserted in the chain (ether function).
  • Said polyol is preferably a linear or branched saturated hydrocarbon- based compound containing 3 to 18 carbon atoms, in particular 3 to 12 or even 4 to 10 carbon atoms, and 3 to 6 hydroxyl (OH) groups. It may be chosen, alone or as a mixture, from:
  • triols such as 1 ,2,4-butanetriol, 1 ,2,6-hexanetriol, trimethylolethane, trimethylolpropane or glycerol;
  • - tetraols such as pentaerythritol (tetramethylolmethane), erythritol, diglycerol or ditrimethylolpropane;
  • - hexols such as sorbitol and mannitol; or alternatively dipentaerythritol or triglycerol.
  • the polyol is chosen from glycerol, pentaerythritol, diglycerol and sorbitol, and mixtures thereof; and even better still the polyol is glycerol.
  • said polyol comprising 3 to 6 hydroxyl groups when present among the ingredients used, it preferably represents 1% to 30% by weight, in particular 2% to 25% by weight, or even 10% to 20% by weight, relative to the total weight used in the synthesis of the cyclodextrin polycondensate .
  • the ratio between the number of moles of polycarboxylic acid and the number of moles of the cyclodextrin preferably ranges from 0.5 to 5, especially from 0.6 to 4, in particular ranging from 0.7 to 3.
  • the cyclodextrin polycondensate according to the invention has an acid number, expressed in mg of potassium hydroxide per g of polycondensate, greater than or equal to 20, in particular ranging from 20 to 250 and even better still ranging from 40 to 180.
  • This acid number may be readily determined by those skilled in the art via the conventional analytical methods.
  • the amount of -COOH groups present is evaluated according to the number of milligrams of potassium hydroxide required to neutralize 1 g of cyclodextrin polycondensate, the dispersion being carried out in a mixture of solvents (1 part of water and 1 part of absolute ethanol).
  • the cyclodextrin polycondensate according to the invention exhibits a degree of swelling in water, measured at 20°C, greater than or equal to 100%, in particular ranging from 100% to 1000% and even better still ranging from 300% to 900%. This degree of swelling is measured in the manner described hereinafter.
  • cyclodextrin polycondensate according to the invention may be prepared via the esterification/polycondensation processes usually used by those skilled in the art.
  • cyclodextrins in mixing together one or more cyclodextrins, a polycarboxylic acid and/or a derivative thereof (esters, acid anhydrides or acid halides), at least one thermoplastic polyol polymer and optionally at least one polycarboxylic acid cyclic anhydride chosen so as to be other than the previous polycarboxylic acid anhydride and/or at least one esterification catalyst and/or at least one non-polymeric polyol comprising 3 to 6 hydroxyl groups,
  • Said preparation process may also comprise a step of adding at least one antioxidant to the reaction medium, in particular in a weight concentration of between 0.01% and 2% relative to the total weight of monomers, so as to limit the possible degradation associated with prolonged heating.
  • the antioxidant may be of primary type or secondary type and may be chosen from hindered phenols, aromatic secondary amines, organophosphorus compounds, sulfur compounds, lactones and bisphenols, and mixtures thereof.
  • antioxidants that are particularly preferred, mention may in particular be made of BHT, BHA, TBHQ, 1 ,3,5-trimethyl-2,4,6,tris(3,5-di- (te rt-b u ty I )-4-hydroxy benzyl) benzene, octadecyl 3,5,di-(tert-butyl)-4- hydroxycinnamate, tetra kis [methyl en e-3-(3,5-di-(te rt-b uty I )-4- hydroxyphenyl)propion ate] methane, octadecyl 3-(3,5-di-(tert-butyl)-4- hydroxyphenyl propionate, 2,5-di-(tert-butyl)hydroquinone, 2,2-methylene- bis(4-methyl-6-(tert-butyl)phenol), 2,2-methylenebis(4-ethyl-6-(
  • One particularly preferred mode of preparation of the cyclodextrin polycondensates of the present invention consists in mixing at least one cyclodextrin, at least one polycarboxylic acid and/or an ester, acid anhydride or acid halide derivative thereof, at least one thermoplastic polyol polymer and optionally at least one polycarboxylic acid cyclic anhydride chosen to be other than the previous polycarboxylic acid anhydride and/or optionally at least one esterification catalyst and/or optionally at least one non-polymeric polyol, in an apparatus which makes it possible to bring the mixture to a thermoplastic state by combining sufficient temperature and shear force conditions, thus making the various components compatible.
  • an extruder for instance of the Clextral BC 21® twin-screw type or any other apparatus which can meet these criteria, which preferably operates at a temperature ranging from 100 to 250°C and preferentially from 110 to 200°C.
  • the preferred mode of preparation of the cyclodextrin polycondensates according to the invention consists in incorporating, in a single step, all the ingredients in an extruder at a temperature ranging from 110 to 200°C, preferably ranging from 120 to 190°C and even better still from 150 to 180°C.
  • the residence time in an extruder preferably ranges from 1 to 10 minutes and even better still from 1 to 5 minutes.
  • said polycondensate may subsequently be ground if required.
  • the cyclodextrin polycondensates of the invention exhibit a porous network which combines superabsorbent properties of sponge type with the ability to form inclusion complexes in the cyclodextrin cavities immobilized within the polymeric network, thus making it possible to capture one or more beneficial agents having an affinity with said polymeric network and to release them, in particular on contact with an aqueous medium or with heat, such as, for example, the contact with the skin or hair and/or the contact with perspiration, with or without an additional stimulus.
  • compositions which make possible the release of a beneficial agent in accordance with the invention generally comprise some or all of said beneficial agent or agents captured and/or encapsulated in the polymeric network of the cyclodextrin polycondensate.
  • the amount of beneficial agent(s) present in the polycondensate will vary according to the nature of the cyclodextrin polycondensate chosen, according to the chemical nature and the affinity of the beneficial agent with regard to said polycondensate, according to the need or not to release the beneficial agent in a significant amount, according to the need or not to release the beneficial agent over a long period of time, according to the nature of the area to which the composition must be applied, indeed even according to the nature or the intensity of the stimulus, if a stimulus must be applied, and more generally according to the requirements of a person skilled in the art.
  • compositions which make possible the release of a beneficial agent according to the invention comprising one or more beneficial agents and a cyclodextrin polycondensate including them, it is possible to proceed in the following way:
  • the beneficial agent or the mixture of beneficial agents is impregnated (encapsulated) within the polycondensate by bringing said beneficial agents into static contact (blotter effect) or into contact with stirring for a time generally of between 1 hour and 24 hours (with the cyclodextrin polycondensate), which agents are pure or conveyed in a solvent or a mixture of solvents, such as water alone, an alcohol, such as ethanol or glycerol, a ketone, such as acetone, or their essentially aqueous mixtures or also in a fluid in a sub- or supercritical state, such as C0 2 or water.
  • a solvent or a mixture of solvents such as water alone, an alcohol, such as ethanol or glycerol, a ketone, such as acetone, or their essentially aqueous mixtures or also in a fluid in a sub- or supercritical state, such as C0 2 or water.
  • Either the amount of beneficial agent(s) which it is desired to encapsulate or an excess of the latter can be added to the cyclodextrin polycondensate. In the latter case, the excess is separated by any appropriate means, such as, for example, centrifugation or filtration.
  • the polycondensate, thus impregnated with beneficial agent(s) is generally left to dry in dry air before it is employed for the purpose of the release of the beneficial agents.
  • beneficial agents to be encapsulated in the polycondensate lends itself thereto, it is also possible to incorporate them during the stage of synthesis of the polycondensate, in particular when the synthesis is carried out, for example, in an extruder.
  • the beneficial agents to be encapsulated in the polycondensate have a specific affinity sufficient for the polycondensate
  • the amount of beneficial agent present in the cyclodextrin polycondensate preferably varies from 1% to 100% by weight and more preferably from 10% to 90% and better still from 20% to 80%, relative to the total weight of the polycondensate.
  • the time for release of the beneficial agent will also vary according to the nature of the cyclodextrin polycondensate chosen and according to the chemical nature and the affinity of the beneficial agent with regard to said polycondensate or according to the nature of the area to which the composition must be applied, indeed even according to the nature or the intensity of the stimulus, if a stimulus must be applied.
  • the total period of time for releasing the beneficial agent will be highly dependent on the nature, in particular chemical nature, of the beneficial agent, on the amount encapsulated in the polycondensate and on the nature and on the intensity of the stimulus to which the polycondensate containing the beneficial agent will be subjected. It is possible to vary this total period of time for release into a large range of times which can extend from a few minutes to a few weeks, which constitutes another advantage of the polycondensates including beneficial agents of the invention. For example, it has been found that, at 150°C, the total period of time for release was generally between 15 minutes and 2 hours. For example, it has also been found that, at a temperature of 37°C and with addition of water, the total period of time for release was greater than 24 hours and could even exceed 72 hours, indeed even reach or exceed a week.
  • flavouring substances and/or taste enhancers (ii) flavouring substances and/or taste enhancers
  • Fatty substances are commonly used in the formulation of pharmaceutical, cosmetic and/or food-processing compositions. They may be chosen from the group comprising:
  • natural oils of vegetable, animal or marine origin such as olive oil, sesame oil, argan oil, palm oil, soya bean oil, woad oil, turtle oil, babassu oil, aloe vera, avocado oil, allantoin, bisabol, grapeseed oil, apricot oil, wheat germ oil, almond oil, groundnut oil, macadamia nut oil, buckthorn oil, evening primrose oil, borage oil, ginger oil, geraniol, jujube oil, mink oil or lanolin,
  • natural oils of vegetable, animal or marine origin such as olive oil, sesame oil, argan oil, palm oil, soya bean oil, woad oil, turtle oil, babassu oil, aloe vera, avocado oil, allantoin, bisabol, grapeseed oil, apricot oil, wheat germ oil, almond oil, groundnut oil, macadamia nut oil, buckthorn oil, evening primrose oil, borage oil, ginger oil, geraniol,
  • mineral oils such as isohexadecane, para-isoparaffin, ceresin or petroleum jelly,
  • hydrocarbon-based compounds such as paraffin oil
  • fatty alcohols such as myristyl alcohol, cetyl alcohol, stearyl alcohol or myricyl alcohol,
  • butters such as shea butter or cocoa butter
  • One of the possible applications according to the invention is the conveying of fatty substances for cosmetic use or for food use or for dietary cosmetic use, such as nutritive supplements.
  • fatty substances for cosmetic use or for food use or for dietary cosmetic use such as nutritive supplements.
  • flavouring substances and/or of taste enhancers for food use or for dietary cosmetic use, such as nutritive supplements.
  • Flavouring substances for food use or for dietary cosmetic use, such as nutritive supplements.
  • flavouring substances mention may be made of those chosen:
  • the European Union defines flavour enhancers in the list of food additives via an E number. They are numbered from E620 (glutamic acid) to E641 (L-leucine).
  • flavour enhancers mention may be made of
  • glutamates such as glutamic acid (E620), monosodium glutamate (E621), monopotassium glutamate (E622), calcium diglutamate (E623), ammonium glutamate (E624) or magnesium diglutamate (E625);
  • guanylates such as guanylic acid or guanisine monophosphate
  • inosinates such as inosinic acid (E630), disodium inosinate (E631), dipotassium inosinate (E632) or calcium inosinate (E633).
  • E634 calcium 5'-ribonucleotide
  • E635 disodium 5'-ribonucleotide
  • E636 maltol
  • E637 ethylmaltol
  • E640 glycine
  • E641 L-leucine
  • lactic acid (acidifier) (E270), sweeteners such as acesulfame- K (E950), aspartame (E951), thaumatin (E957), neohesperidin dihydrochalcone (E959), neotame (E961) or erythritol (E968).
  • sweeteners such as acesulfame- K (E950), aspartame (E951), thaumatin (E957), neohesperidin dihydrochalcone (E959), neotame (E961) or erythritol (E968).
  • Fragrancing substances is intended to mean any fragrance or aroma capable of giving off a pleasant odour.
  • Fragrances are compositions in particular containing the starting materials described in S. Arctander, Perfume and Flavor Chemicals (Montclair, N.J., 1969), in S. Arctander, Perfume and Flavor Materials of Natural Origin (Elizabeth, N.J., 1960) and in Flavor and Fragrance Materials - 1991, Allured Publishing Co., Wheaton, III.
  • an essential oil is an odorous product generally of complex composition, obtained from a botanically defined plant starting material, either by steam distillation, or by dry distillation, or via an appropriate mechanical method without heating (cold pressing).
  • the essential oil is generally separated from the aqueous phase by a physical method which does not result in any significant change in the composition.
  • Abietaceae or Pinaceae conifers; Amaryllidaceae; Anacardaceae; Anonaceae: ylang ylang; Apiaceae (for example Umbelliferae): dill, angelica, coriander, sea fennel, carrot, parsley; Araceae; Aristolochiaceae; Asteraceae: yarrow, artemisia, camomile, helichrysum; Betulaceae; Brassicaceae; Burseraceae: frankincense; Carophyllaceae; Canellaceae; Cesalpiniaceae: copaifera (copaiba balsam); Chenopodaceae; Cistaceae: rock rose; Cyperaceae; Dipterocarpaceae; Ericaceae: gaultheria (wintergreen); Euphorbiaceae; Fabaceae; Geraniaceae: geranium; Guttiferae; Hamamelidaceae; Her
  • fragrancing substances are in particular: geraniol, geranyl acetate, farnesol, borneol, bornyl acetate, linolool, linalyl acetate, linalyl propionate, linalyl butyrate, tetrahydrolinolool, citronellol, citronellyl acetate, citronellyl formate, citronellyl propionate, dihydromyrcenol, dihydromyrcenyl acetate, tetrahydromyrcenol, terpineol, terpinyl acetate, nopol, nopyl acetate, nerol, neryl acetate, 2-phenylethanol, 2-phenylethyl acetate, benzyl alcohol, benzyl acetate, benzyl salicylate, styrallyl acetate, benzyl benzoate, amyl
  • Another of the possible applications is, for example, the conveying of fragrancing substances for the manufacture of perfumery products (fragrances, eaux de toilette, eaux de perfume, aftershave lotions), cosmetic products for caring for and/or cleansing keratin materials, in particular human keratin materials, makeup products, laundry cleaning and/or care products, household products, in the manufacture of clothing, shoes, soles and products for the maintenance thereof, in products intended for animal hygiene, such as litters, in inks, products resulting from the paper industry, in products intended for babycare (wipes, nappies), in products intended for intimate hygiene (tampons, wipes, towels), in products for sanitary use, and in food-processing products and products resulting from agriculture.
  • composition of a medicament is intended to mean a molecule which has a curative and/or prophylactic therapeutic effect.
  • it may be any molecule with therapeutic properties which is part of the composition of a medicament.
  • NSAIDs non-steroidal anti-inflammatory drugs
  • abortifacients alpha-blockers, alpha2-agonists, aminosides, analgesics, anaesthetics, local anaesthetics, anorexigenics, 5HT3 antagonists, calcium antagonists, anti-angina agents, antiarrhythmics, antibiotics, anticholinergics, anticholinesterases, antidiabetics, anti-diarrhoea agents, antidepressants, antihistamines, antihypertensives, antimycotics, antimalarials, antiparasitics, antipsychotics, antipyretics, antiretrovirals, antiseptics, antispasmodics
  • NSAIDs non-steroidal anti-inflammatory drugs
  • cosmetic active agent is intended to mean any molecule which has a hygiene, care, makeup or dyeing effect contributing to improving the well-being and/or to making more attractive or modifying the appearance of the human keratin material to which said composition is applied.
  • the cosmetic active agents can therefore be chosen from any of the substances which meet this definition and which are present in products such as
  • hygiene products makeup-removing products, toothpastes, deodorants, antiperspirants, shower gels, bath preparations (bubble bath, bath oil, bath salts), intimate cleansing gels, soaps, shampoos,
  • care products antiwrinkle cream, day cream, night cream, moisturizing cream, floral water, scrubbing product, milk, beauty mask, lip balm, tonic,
  • hair care and/or treatment products such as styling products, dyeing products, permanent-waving products, conditioning products: conditioner, hair relaxing product, hair straightening product; gel, oil, lacquer, mask, anti-dandruff agents,
  • makeup products concealer, eyeliner, face powder, foundation, khol, mascara, powder, skin whitening product, lipstick, nail varnish,
  • fragrances eau de Cologne, eau de toilette, perfume
  • suntan products self-tanning products, aftersun creams, milks, oils, sticks or lotions and anti-sun products,
  • shaving products and hair removal products aftershave, hair removal cream, shaving foam and gels.
  • active agents for caring for human keratin materials such as the skin, the lips, the scalp, the hair, the eyelashes or the nails
  • active agents for caring for human keratin materials such as the skin, the lips, the scalp, the hair, the eyelashes or the nails
  • examples that may be mentioned include:
  • - NO-synthase inhibitors - agents which stimulate the synthesis of dermal or epidermal macromolecules and/or which prevent degradation thereof;
  • cyclodextrin polycondensates according to the invention can be used very advantageously in a cosmetic or dermatological composition which comprises, moreover, a physiologically acceptable medium.
  • the amount of cyclodextrin polycondensate present in the compositions obviously depends on the type of composition and on the desired properties and may vary within a very wide range, generally ranging from 0.1% to 100% by weight, preferably from 0.5% to 95% by weight, in particular from 1% to 70% by weight, or even from 1.5% to 50% by weight and better still from 2% to 20% by weight, relative to the total weight of the composition.
  • composition may thus comprise, depending on the intended application, constituents that are common for this type of composition.
  • composition according to the invention may advantageously comprise at least one fatty phase which may comprise at least one compound chosen from volatile or non-volatile carbon-based, hydrocarbon-based, fluoro and/or silicone oils, waxes and/or solvents of mineral, animal, plant or synthetic origin, alone or as a mixture, provided that they form a stable, homogeneous mixture and are compatible with the intended use.
  • volatile is intended to mean any compound that is capable of evaporating on contact with keratin materials in less than one hour, at ambient temperature (25°C) and atmospheric pressure (1 atm).
  • this volatile compound has a non-zero vapour pressure, at ambient temperature and atmospheric pressure, ranging 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).
  • non-volatile is intended to mean a compound that remains on human keratin materials at ambient temperature and atmospheric pressure for at least one hour and that in particular has a vapour pressure of less than 10 "3 mmHg (0.13 Pa).
  • the fatty phase may represent from 1% to 99% by weight of the composition, especially from 5% to 95% by weight, in particular from 10% to 90% by weight, or even from 20% to 85% by weight, of the total weight of the composition.
  • the composition may also comprise other ingredients commonly used in cosmetic compositions.
  • Such ingredients may be chosen from antioxidants, fragrances, essential oils, preservatives, cosmetic active agents, moisturizers, vitamins, ceramides, sunscreens, surfactants, spreading agents, wetting agents, dispersants, antifoams, neutralizing agents, stabilizers, polymers and in particular liposoluble film-forming polymers, and mixtures thereof.
  • antioxidants fragrances, essential oils, preservatives, cosmetic active agents, moisturizers, vitamins, ceramides, sunscreens, surfactants, spreading agents, wetting agents, dispersants, antifoams, neutralizing agents, stabilizers, polymers and in particular liposoluble film-forming polymers, and mixtures thereof.
  • compositions according to the invention may be in any common acceptable form for a cosmetic or dermatological composition.
  • Those skilled in the art may select the appropriate galenical form, and also the method for preparing it, on the basis of their general knowledge, taking into account both the nature of the constituents used, in particular their solubility in the support, and also the intended use of the composition.
  • the ⁇ -cyclodextrin polycondensate 1 a was obtained after extrusion of the ⁇ -cyclodextrin (CD) in the presence of hydroxypropylcellulose (HPC), citric acid and sodium dihydrogen phosphate (DHPS).
  • HPC hydroxypropylcellulose
  • DHPS sodium dihydrogen phosphate
  • the polycondensate 1 a was obtained in the form of a cream-coloured powder with an average particle size of 10 ⁇ .
  • the cyclodextrin polycondensate 1 a has an acid number of 150 mg of potassium hydroxide per g of polycondensate and a degree of swelling in water of 805%.
  • the solid obtained was detached from the crystallizing dish and then finely milled using a knife mill of coffee mill type. It was analyzed by 2D DOSY NMR which made it possible to demonstrate the covalent grafting of the citric acid onto the ⁇ -cyclodextrin so as to form an oligomer, the diffusion coefficient of which is 173 ⁇ " ⁇ 2 /8, which corresponds to a molecular weight estimated at approximately 3800 g/mol. Its acid number is 195 mg of potassium hydroxide per g of polycondensate and its degree of swelling in water is 0% since it is entirely soluble at ambient temperature (solubility greater than 30%). Encapsulation of a fragrancing substance and time of release
  • the ⁇ -cyclodextrin polycondensate 1 a according to the invention exhibits a level of fragrance encapsulation which is 3.7 times greater than that of ⁇ -cyclodextrin, than that of the comparative ⁇ -cyclodextrin polycondensate A and than that of the comparative ⁇ -cyclodextrin polycondensate B.
  • ⁇ -cyclodextrin polycondensate 1 a results in a longer fragrance release time than that obtained with ⁇ -cyclodextrin, than that obtained with the comparative ⁇ -cyclodextrin polycondensate A and than that obtained with the comparative ⁇ -cyclodextrin polycondensate B.
  • ⁇ -cyclodextrin polycondensate 1 c exhibits a level of fragrance encapsulation which is 3.4 times greater than that of the comparative ⁇ -cyclodextrin polycondensate 3a.

Abstract

La présente invention concerne une composition qui rend possible la libération d'un agent bénéfique et qui comprend au moins un agent bénéfique et un support comprenant au moins un polycondensat de cyclodextrine insoluble dans l'eau qui peut être obtenu par réaction d'estérification/de polycondensation : A) d'au moins une cyclodextrine et B) d'au moins un acide polycarboxylique saturé, insaturé ou aromatique, linéaire, ramifié ou cyclique et/ou d'au moins un ester ou un anhydride d'acide ou un halogénure d'acide dudit acide polycarboxylique et C) d'au moins un polymère de polyol thermoplastique et D) éventuellement d'au moins un catalyseur d'estérification et/ou E) éventuellement d'au moins un anhydride cyclique d'un acide polycarboxylique choisi de sorte à être autre que l'anhydride d'acide polycarboxylique du paragraphe B), et/ou F) éventuellement d'au moins un polyol non polymère comprenant de 3 à 6 groupes hydroxyle. L'invention concerne également un produit de consommation comprenant au moins une composition qui rend possible la libération d'un agent bénéfique tel que défini précédemment, en particulier une composition cosmétique ou dermatologique comprenant un milieu physiologiquement acceptable. L'invention concerne en outre un procédé pour le traitement cosmétique d'un tissu à base de kératine, et qui consiste à appliquer, sur la surface dudit tissu à base de kératine humaine, un produit de consommation comprenant une composition telle que susmentionnée et qui contient, dans un milieu physiologiquement acceptable, au moins un agent bénéfique choisi parmi des agents actifs cosmétiques.
PCT/EP2013/075813 2012-12-20 2013-12-06 Composition permettant la libération d'un agent bénéfique comprenant un polycondensat de cyclodextrine insoluble dans l'eau et au moins un agent bénéfique WO2014095426A1 (fr)

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Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2017134250A1 (fr) * 2016-02-05 2017-08-10 Bertrand Duval Utilisation d'un polycondensat de cyclodextrine ou d'une composition comprenant un tel polycondensat, comme agent de capture
CN110921632A (zh) * 2019-12-19 2020-03-27 河南金丹乳酸科技股份有限公司 不改变通气控制策略而促进乳酸菌快速消耗糖的供氧剂制备方法
CN112877383A (zh) * 2021-01-21 2021-06-01 大连大学 一种固定化脂肪酶催化柠檬酸功能化β-环糊精及其制备方法
CN114602434A (zh) * 2022-03-08 2022-06-10 中国地质大学（武汉） 环糊精基吸附材料及其制备方法和应用
CN114945599A (zh) * 2020-02-17 2022-08-26 易希提卫生与保健公司 层纤维产品
CN115429731A (zh) * 2022-10-09 2022-12-06 广州阿基米德生物科技有限公司 一种含超分子聚合物的美白祛斑组合物及其制备方法和应用

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP4076348A1 (fr) * 2019-12-20 2022-10-26 L V M H Recherche Produit cosmétique de type émulsion huile dans l'eau

Citations (21)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3420788A (en) 1964-04-29 1969-01-07 Afico Sa Inclusion resins of cyclodextrin and methods of use
US3472835A (en) 1964-02-12 1969-10-14 American Mach & Foundry Schardinger dextrins
JPS58171404A (ja) 1982-03-31 1983-10-08 Agency Of Ind Science & Technol ポリシクロデキストリンビ−ズの製法
JPS61283601A (ja) 1985-06-10 1986-12-13 Nippon Junyaku Kk ポリシクロデキストリンビ−ズの製造方法
US4902788A (en) 1988-09-29 1990-02-20 Uop Crosslinked cyclodextrins supported on porous refractory inorganic oxides
US4917956A (en) 1988-07-11 1990-04-17 Uop Method of preparing cyclodextrin-coated surfaces
US4958015A (en) 1988-09-30 1990-09-18 Uop Preparation of crosslinked cyclodextrin resins with enhanced porosity
DE4009825A1 (de) 1990-03-27 1991-10-02 Consortium Elektrochem Ind Wasserunloesliche cyclodextrin-polymerisate und verfahren zu deren herstellung
WO1995019994A1 (fr) 1994-01-25 1995-07-27 Commissariat A L'energie Atomique Procede de solubilisation dans un milieu aqueux d'agents antitumoraux de la famille du taxol, et cyclodextrines ramifiees utilisables pour cette solubilisation
WO1995021870A1 (fr) 1994-02-11 1995-08-17 Commissariat A L'energie Atomique Procede de preparation de cyclomaltooligosaccharides ramifies, en particulier de cyclodextrines ramifiees
DE19520989A1 (de) 1995-06-08 1996-12-12 Consortium Elektrochem Ind Cyclodextrinmodifizierte Polymere
EP0780401A1 (fr) 1995-12-21 1997-06-25 Basf Aktiengesellschaft Procédé de préparation de polymères par polymérisation en émulsion
WO1997033919A1 (fr) 1996-03-14 1997-09-18 Centre National De La Recherche Scientifique Thioureido-cyclodextrines, utilisables en particulier pour solubiliser des agents antitumoraux et antiparasitaires et leurs procedes de preparation
US5734031A (en) 1995-09-25 1998-03-31 The United States Of America As Represented By The Secretary Of Agriculture Cation exchange resin
WO1998022197A1 (fr) 1996-11-22 1998-05-28 The Regents Of The University Of California Matieres de separation en polymeres de cyclodextrine
WO2000047630A1 (fr) * 1999-02-15 2000-08-17 Universite Des Sciences Et Technologies De Lille Polymeres de cyclodextrine(s) et/ou derives de cyclodextrine(s) presentant des proprietes complexantes et echangeuses d'ions et leur procede de fabrication
WO2000076472A1 (fr) * 1999-06-14 2000-12-21 The Procter & Gamble Company Compositions de creme desodorisante anhydre ayant une duree de vie plus longue du parfum
WO2001048025A1 (fr) 1999-12-28 2001-07-05 Kimberly-Clark Worldwide, Inc. Cyclodextrines liees de maniere covalente a des polysaccharides
WO2010070235A2 (fr) 2008-12-19 2010-06-24 L'oreal Composition de maquillage des matieres keratiniques comprenant au moins un polysaccharide oxyde non cationique
FR2944967A1 (fr) 2009-04-30 2010-11-05 Oreal Utilisation d'un polysaccharide oxyde pour proteger la couleur de fibres keratiniques ; procedes de coloration
WO2011161020A1 (fr) 2010-06-21 2011-12-29 L'oreal Composition cosmétique comprenant au moins un polysaccharide oxydé non cationique et une huile, préférentiellement une huile non polaire

Patent Citations (22)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3472835A (en) 1964-02-12 1969-10-14 American Mach & Foundry Schardinger dextrins
US3420788A (en) 1964-04-29 1969-01-07 Afico Sa Inclusion resins of cyclodextrin and methods of use
JPS58171404A (ja) 1982-03-31 1983-10-08 Agency Of Ind Science & Technol ポリシクロデキストリンビ−ズの製法
JPS61283601A (ja) 1985-06-10 1986-12-13 Nippon Junyaku Kk ポリシクロデキストリンビ−ズの製造方法
US4917956A (en) 1988-07-11 1990-04-17 Uop Method of preparing cyclodextrin-coated surfaces
US4902788A (en) 1988-09-29 1990-02-20 Uop Crosslinked cyclodextrins supported on porous refractory inorganic oxides
US4958015A (en) 1988-09-30 1990-09-18 Uop Preparation of crosslinked cyclodextrin resins with enhanced porosity
DE4009825A1 (de) 1990-03-27 1991-10-02 Consortium Elektrochem Ind Wasserunloesliche cyclodextrin-polymerisate und verfahren zu deren herstellung
WO1995019994A1 (fr) 1994-01-25 1995-07-27 Commissariat A L'energie Atomique Procede de solubilisation dans un milieu aqueux d'agents antitumoraux de la famille du taxol, et cyclodextrines ramifiees utilisables pour cette solubilisation
WO1995021870A1 (fr) 1994-02-11 1995-08-17 Commissariat A L'energie Atomique Procede de preparation de cyclomaltooligosaccharides ramifies, en particulier de cyclodextrines ramifiees
DE19520989A1 (de) 1995-06-08 1996-12-12 Consortium Elektrochem Ind Cyclodextrinmodifizierte Polymere
US5734031A (en) 1995-09-25 1998-03-31 The United States Of America As Represented By The Secretary Of Agriculture Cation exchange resin
EP0780401A1 (fr) 1995-12-21 1997-06-25 Basf Aktiengesellschaft Procédé de préparation de polymères par polymérisation en émulsion
WO1997033919A1 (fr) 1996-03-14 1997-09-18 Centre National De La Recherche Scientifique Thioureido-cyclodextrines, utilisables en particulier pour solubiliser des agents antitumoraux et antiparasitaires et leurs procedes de preparation
WO1998022197A1 (fr) 1996-11-22 1998-05-28 The Regents Of The University Of California Matieres de separation en polymeres de cyclodextrine
WO2000047630A1 (fr) * 1999-02-15 2000-08-17 Universite Des Sciences Et Technologies De Lille Polymeres de cyclodextrine(s) et/ou derives de cyclodextrine(s) presentant des proprietes complexantes et echangeuses d'ions et leur procede de fabrication
EP1165621B1 (fr) 1999-02-15 2002-10-02 Universite Des Sciences Et Technologies De Lille Polymeres de cyclodextrine(s) et/ou derives de cyclodextrine(s) presentant des proprietes complexantes et echangeuses d'ions et leur procede de fabrication
WO2000076472A1 (fr) * 1999-06-14 2000-12-21 The Procter & Gamble Company Compositions de creme desodorisante anhydre ayant une duree de vie plus longue du parfum
WO2001048025A1 (fr) 1999-12-28 2001-07-05 Kimberly-Clark Worldwide, Inc. Cyclodextrines liees de maniere covalente a des polysaccharides
WO2010070235A2 (fr) 2008-12-19 2010-06-24 L'oreal Composition de maquillage des matieres keratiniques comprenant au moins un polysaccharide oxyde non cationique
FR2944967A1 (fr) 2009-04-30 2010-11-05 Oreal Utilisation d'un polysaccharide oxyde pour proteger la couleur de fibres keratiniques ; procedes de coloration
WO2011161020A1 (fr) 2010-06-21 2011-12-29 L'oreal Composition cosmétique comprenant au moins un polysaccharide oxydé non cationique et une huile, préférentiellement une huile non polaire

Non-Patent Citations (15)

* Cited by examiner, † Cited by third party
Title
"Flavor and Fragrance Materials", 1991, ALLURED PUBLISHING CO.
"Flavouring substances and natural sources of flavouring materials", vol. 1, 1992
ASANUMA H. ET AL., CHEM. COMMUN, 1997, pages 1971 - 1972
B. MARTEL ET AL., JOURNAL OF APPLIED POLYMER SCIENCE, vol. 97, 2005, pages 433 - 442
FENYVESI E. ET AL.: "Ann. Univ. Sci. Budapest, Rolando Eotvos Nominatae", SECT. CHIM., vol. 15, 1979, pages 13 - 22
HARADA A. ET AL., MACROMOLECULES, vol. 9, no. 5, 1976, pages 701 - 704
HOFFMAN J.L., J. MACROMOL. SCI.-CHEM, vol. A7, no. 5, 1973, pages 1147 - 1157
J.L. ATWOOD ET AL.,: "Comprehensive Supramolecular Chemistry", vol. 3, 1996, PERGAMON PRESS
S. ARCTANDER: "Perfume and Flavor Chemicals", 1969
S. ARCTANDER: "Perfume and Flavor Materials of Natural Origin", 1960
SOLMS; EGI, HELV. CHIM. ACTA, vol. 48, 1965, pages 1225
SUGIURA I. ET AL., BULL. CHEM. SOC. JPN., vol. 62, 1989, pages 1643 - 1651
TOMOYA T. ET AL., J. POLYM. SCI., PART A: POLYM. CHEM., vol. 36, no. 11, 1998, pages 1965 - 1968
WIEDENHOF N. ET AL., DIE STARKE, vol. 21, no. 5, 1989, pages 119 - 123
WIMMER T. ET AL.: "Minutes Int. Symp. Cyclodextrins 6th 106-109", 1992, pages: 106 - 109

Cited By (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2017134250A1 (fr) * 2016-02-05 2017-08-10 Bertrand Duval Utilisation d'un polycondensat de cyclodextrine ou d'une composition comprenant un tel polycondensat, comme agent de capture
FR3047484A1 (fr) * 2016-02-05 2017-08-11 Bertrand Duval Polycondensat de cyclodextrine, composition comprenant un tel polycondensat et leurs utilisations comme agent de capture
CN109071882A (zh) * 2016-02-05 2018-12-21 伯特兰德.杜瓦尔 环糊精缩聚物或包括该缩聚物的组合物作为俘获试剂的用途
US10851223B2 (en) 2016-02-05 2020-12-01 Biostart Use of a cyclodextrin polycondensate or a composition comprising such a polycondensate, as a capturing agent
CN109071882B (zh) * 2016-02-05 2022-11-15 伯特兰德.杜瓦尔 环糊精缩聚物或包括该缩聚物的组合物作为俘获试剂的用途
CN110921632A (zh) * 2019-12-19 2020-03-27 河南金丹乳酸科技股份有限公司 不改变通气控制策略而促进乳酸菌快速消耗糖的供氧剂制备方法
CN114945599A (zh) * 2020-02-17 2022-08-26 易希提卫生与保健公司 层纤维产品
CN112877383A (zh) * 2021-01-21 2021-06-01 大连大学 一种固定化脂肪酶催化柠檬酸功能化β-环糊精及其制备方法
CN114602434A (zh) * 2022-03-08 2022-06-10 中国地质大学（武汉） 环糊精基吸附材料及其制备方法和应用
CN115429731A (zh) * 2022-10-09 2022-12-06 广州阿基米德生物科技有限公司 一种含超分子聚合物的美白祛斑组合物及其制备方法和应用
CN115429731B (zh) * 2022-10-09 2023-09-12 阿基米德(广州)化妆品研究有限公司 一种含超分子聚合物的美白祛斑组合物及其制备方法和应用

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