WO2024017930A1 - Fragranced cosmetic composition comprising at least one flavonoid compound, ethanol, a water-soluble colorant and a fragrancing substance - Google Patents

Fragranced cosmetic composition comprising at least one flavonoid compound, ethanol, a water-soluble colorant and a fragrancing substance Download PDF

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Publication number
WO2024017930A1
WO2024017930A1 PCT/EP2023/069984 EP2023069984W WO2024017930A1 WO 2024017930 A1 WO2024017930 A1 WO 2024017930A1 EP 2023069984 W EP2023069984 W EP 2023069984W WO 2024017930 A1 WO2024017930 A1 WO 2024017930A1
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group
weight
composition
chosen
water
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PCT/EP2023/069984
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French (fr)
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Christophe BOBIN
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L'oreal
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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
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/34—Alcohols
    • 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
    • A61K8/498—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with oxygen as the only hetero atom having 6-membered rings or their condensed derivatives, e.g. coumarin
    • 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
    • A61K2800/52—Stabilizers
    • A61K2800/522—Antioxidants; Radical scavengers

Definitions

  • Fragranced cosmetic composition comprising at least one flavonoid compound, ethanol, a water-soluble colorant and a fragrancing substance
  • the present invention is targeted at providing a novel fragranced cosmetic composition, for the field of fragrancing keratin materials and/or clothing, but also for the cosmetic treatment or care of keratin materials.
  • a fragrance is the result of a combination of different odorous substances which each provide a specific diffusing odour or also “note” and which respectively evaporate at different periods. More specifically, each fragrance has what is known as a “top note”, which is the odour which diffuses first when the fragrance is applied or when the receptacle containing it is opened, a “middle or heart note”, which corresponds to the full fragrance (given off for a few hours after the “top note”) and a “base note”, which is the most persistent odour (given off for several hours after the “middle note”). The persistence of the base note corresponds to the holding of the fragrance.
  • fragrance in a certain number of products or compositions, in particular cosmetic and dermatological products or compositions, such as eaux fraiches, eaux de toilette, eaux de perfume, fragrance elixirs or extracts, aftershave lotions, eaux de soin or also two-phase lotions.
  • fragrancing compositions such as fragrances or eaux de toilette
  • the use of ethanol as solvent is very widespread.
  • Ethanol makes it possible to fully dissolve the fragrancing ingredients resorted to by the perfumer. It is a very good solvent which evaporates quickly, thus giving a feeling of freshness. Ethanol additionally exhibits the advantage of being inexpensive and of making possible the formulation of transparent compositions.
  • fragrancing compositions contain ethanol, generally present in high contents, typically in contents of greater than 15% by weight of the total weight of these compositions.
  • fragrances are coloured by adding an effective amount of colorant to the support of the formulation (which is generally alcoholic or aqueous/alcoholic) rather than tinting or lacquering the bottle, which is a more expensive industrial operation.
  • Mention may more particularly be made, as colorants, of water-soluble dyes, in particular which are natural or of natural origin, which, in a form diluted in aqueous media, provide the chromatic colouration which is most intense and therefore particularly advantageous for the field of cosmetics.
  • fragranced compositions including in particular dyes, comprising combinations of UV screening agents as stabilizer, in particular of alkyl P,P’- diphenylacrylate or alkyl a-cyano-P,P’ -diphenylacrylate type, such as octocrylene, dibenzoylmethane derivatives, cinnamates or also camphor derivatives and triazines.
  • Synthetic screening agents such as ethylhexyl methoxycinnamate, are also unsatisfactory for stabilizing fragrancing solution colorants. In particular, they prove to be less efficient in terms of preserving the intensity of the colour and/or the chromaticity of the coloured solution with respect to light and/or over time.
  • piperidinol derivatives used in some of these compositions exhibit the disadvantage of generating yellowing in eaux de toilette and also a spurious odour with a “chemical” connotation.
  • sunscreens provided to date such as ethylhexyl methoxy cinnamate, are synthetic.
  • coloured fragranced compositions which are "less chemical” and more environmentally friendly. These users may perceive synthetic compounds negatively, in particular as compounds which are harmful to their health and to the environment.
  • coloured fragranced compositions comprising synthetic sunscreens are not entirely satisfactory for consumers favouring natural compounds or compounds of natural origin over synthetic compounds.
  • the document WO 2017/162599 describes the stabilization of water-soluble natural dyes or dyes of natural origin using specific polymeric surfactants or fillers. Also, the document WO 2009/031051 provides for the stabilization of anthocyanin extracts with a stabilizing compound comprising a thiol group, in the field of food compositions.
  • a need remains to have available coloured fragranced cosmetic compositions, the change in the organoleptic properties, namely the odour and/or the colour, in particular at least the colour, of which is controlled over time, and this being achieved, if possible, by means of compounds which observe at least one of the twelve principles of green chemistry.
  • the formulation of which observes at least one of the twelve principles of green chemistry, in particular comprising ingredients resulting from green chemistry are provided.
  • the present invention is specifically targeted at meeting these needs.
  • the present invention relates to a fragranced composition, in particular cosmetic composition, comprising: a) at least one compound corresponding to the formula (I), or one of its geometrical isomers, in particular optical isomers, of its tautomers, and also its organic or inorganic acid or base salts, or of its solvates, in particular hydrates: [Chem 1] in which formula (I): represents a double bond or a single bond, ⁇ R 1 represents an atom or a group chosen from: - a hydrogen atom, - a hydroxyl, - a (C1-C6)alkyl group, - a (C 1 -C 6 )alkoxy group, - a monoglycoside or diglycoside sugar group, such as a glycosyl group, or an -O- monoglycoside or -diglycoside sugar group, such as an -O-glycosyl group; ⁇ R 2 represents
  • the inventors have found, surprisingly, that the combination of a compound of formula (I) as defined above, within a fragranced composition comprising a high ethanol content, with at least one fragrancing substance and at least one water-soluble colorant, makes possible efficient stabilization of said composition, in particular of its colour.
  • the composition according to the invention is stable, in the sense that the change in the colour of the composition remains low over time, even under conditions simulating an accelerated ageing of the composition, in particular in an aqueous/alcoholic medium having a high ethanol content, and to light.
  • the invention also relates, according to another of its aspects, to the use of a compound of formula (I) as stabilizer in a fragranced composition, in particular a cosmetic composition, additionally comprising ethanol in a content strictly greater than 15% by weight, with respect to the total weight of the composition, and also at least one water-soluble colorant and at least one fragrancing substance.
  • a composition according to the invention is intended in particular for the cosmetic treatment of keratin materials.
  • the invention relates, according to another of its aspects, to a method for the cosmetic treatment of keratin materials, in particular of the skin, comprising at least one stage of application, to said keratin materials, of a composition according to the invention.
  • the invention also relates to a method for the cosmetic treatment of keratin materials, in particular of the skin, or of clothing, comprising at least one stage of application, to said keratin materials and/or said clothing, of a fragranced composition according to the invention.
  • a composition according to the invention is intended in particular to be employed in order to fragrance keratin materials and/or clothes.
  • the invention also relates, according to another of its aspects, to a method for the fragrancing of keratin materials, and in particular of the skin, and/or of clothing, comprising the application, to said keratin materials and/or said clothing, of the composition as defined above.
  • the content of water-soluble colorant(s) in the fragranced coloured composition can be less than or equal to 300 ppm.
  • fragmented composition or “fragrancing composition” is understood to denote any composition which leaves a fragrance after application on keratin materials.
  • keratin materials is understood in particular to denote the skin, the lips, the hair, the scalp, the eyelashes and the eyebrows or also the nails, in particular the skin and/or the lips, and preferably the skin.
  • colorant is understood to denote any compound capable of colouring the fragranced composition, that is to say any compound which absorbs in the visible spectrum, in particular so as to appear to the human eye to have a colour such as yellow, orange, red, purple, blue or green, in particular orange, red, purple or blue.
  • a fragranced composition according to the invention is said to be “coloured” .
  • the term “coloured composition” is understood to mean a composition which appears to the human eye to have a colour in the visible spectrum, that is to say which to the eye is distinct from white or colourless, namely a composition which absorbs in the yellow, orange, red, crimson, purple, blue and green ranges.
  • Such a composition can be opaque or clear, preferably clear.
  • the term “ clear ' is understood to mean that the composition is transparent, that is to say that it allows light to pass through and allows objects which are located behind to appear in sharp definition.
  • water-soluble is understood to mean that the natural or synthetic, generally organic, colorant is soluble in an aqueous phase or water-miscible solvents.
  • a fragranced coloured composition can be in any form suitable for its application to keratin materials and/or clothing. It can in particular be in liquid or solid form, for example in powder form.
  • the term “powder” is understood to mean a composition in pulverulent form, which is preferably essentially devoid of dust.
  • the particle size distribution of the particles is such that the content by weight of the particles which have a size of less than or equal to 50 micrometres (dust content), preferably of less than or equal to 10 micrometres (dust content), is advantageously less than or equal to 5%, preferably less than 2% and more particularly less than 1% (size of the particles evaluated using a Retsch AS 200 Digit particle size analyser; oscillation height: 1.25 mm/sieving time: 5 minutes).
  • the size of the particles is between 10 pm and 500 pm.
  • the “powder” of solid material(s) can be sieved in order to obtain particles with upper limit sizes corresponding to the orifices or sizes of the meshes of the sieve of particularly between 35 and 80 mesh (US).
  • the size of the particles of the powder of solid natural material(s) is fine. According to the invention, this more particularly means a size of particles of less than or equal to 900 pm.
  • the powder is constituted of fine particles with a size of between 7 pm and 700 pm and better still between 100 nm and 500 pm.
  • fragmentrancing substance is understood to denote any fragrance, odorous starting material or aroma which is capable of giving off a pleasant odour, in particular as defined in the continuation of the text.
  • fragmentrancing , “odorous” or “odoriferous” substances are synonymous.
  • a composition according to the invention is generally suitable for application to keratin materials, in particular topical application to the skin, and thus generally comprises a physiologically acceptable medium, that is to say a medium compatible with the skin.
  • a cosmetically acceptable medium that is to say a medium which exhibits a pleasant colour, odour and feel and which does not cause any unacceptable discomfort, that is to say stinging, tautness or redness, liable to dissuade the user from applying this composition.
  • a “stabilizer” is understood to denote a compound which is capable of stabilizing the fragranced composition comprising it, in particular in terms of preservation of its organoleptic properties with respect to external attacking factors, in particular light or temperature differences, in particular the colour and/or the odour of said composition, and more particularly still the colour of said composition.
  • a (Cx-Cz)alkyl group represents a linear or branched hydrocarbon chain comprising from x to z carbon atoms.
  • a (C 1 -C 6 )alkyl group represents a linear or branched hydrocarbon chain comprising from 1 to 6 carbon atoms.
  • a (Cx-Cz)alkoxy group represents an -O-(Cx-Cz)alkyl radical in which the (Cx-Cz)alkyl group is as defined above.
  • a “sugar” radical is understood to denote a monosaccharide, oligosaccharide or polysaccharide radical, in particular constituted of from 1 to 5 saccharide units, more particularly from 2 to 3 and preferably of 2 saccharide units, bonded via a covalent bond to the compound carrying the group. Mention may be made, as sugar radical, of sucrose, glucose, galactose, ribose, fucose, maltose, fructose, mannose, arabinose, xylose or lactose.
  • glycosyl group is understood to denote a monovalent radical obtained from a mono- or oligosaccharide by replacement of one of the hemiacetal hydroxyl groups of said mono- or oligosaccharide by a covalent bond with the compound carrying the group.
  • the compound of formula (I) is chosen from natural compounds or compounds of natural origin.
  • the term “natural” is understood to mean that the colorant is obtained directly from the earth or the soil, or from plants or animals, via, if appropriate, one or more physical processes, such as, for example, milling, refining, distillation, purification or filtration, or else results from a biotechnological process, in particular results from microbiological or cell cultures, for example of fungi or of bacteria.
  • Natural dyes or pigments include compounds which are present in nature and which can be reproduced by chemical (semi)synthesis.
  • the term “of natural origin” is understood to mean that the colorant is obtained from a natural substance which has undergone one or more additional chemical or industrial treatments bringing about modifications which do not affect the essential qualities of this substance. Mention may be made, as non-limiting example of additional chemical or industrial treatment bringing about modifications which do not affect the essential qualities of a natural compound, of those authorized by the controlling bodies, such as Ecocert (Reference system for biological and ecological cosmetic products, January 2003), or defined in recognized handbooks in the field, such as “Cosmetics and Toiletries Magazine”, 2005, Vol. 120, 9 (10).
  • a compound is considered to be natural or of natural origin when it is predominantly composed of natural constituents, that is to say when the ratio by weight of natural constituents to non-natural constituents which make up the compound is greater than 1.
  • the compound of formula (I) is a “green” compound, namely that it observes at least one of the twelve principles of green chemistry.
  • geometrical isomer is understood to denote any molecule of identical constitution to the formula (I) defined above but the spatial organization of the atoms of which is different.
  • they can be conformational stereoisomers, that is to say compounds which differ by rotation around a single bond, or configurational stereoisomers, in particular enantiomers or diastereoisomers (or optical isomers), or also constitutional isomers, that is to say compounds which differ in the sequence of the atoms, in particular tautomers in the case of tautomeric equilibrium.
  • organic or inorganic acid or base salt is understood to denote a salt obtained between an ionic form of a compound of formula (I) and a corresponding counterion.
  • a salt is obtained by addition of an organic or inorganic acid or base, which is in particular cosmetically acceptable, to the compound of formula (I).
  • inorganic bases of hydroxides or carbonates of alkali or alkaline earth metals, such as sodium, potassium, calcium, ammonium, magnesium, lithium or sodium.
  • organic bases of amines or alkanolamines.
  • acids of hydrochloric acid, hydrobromic acid, sulfuric acid, alkylsulfonic acids, arylsulfonic acids, citric acid, succinic acid, tartaric acid, lactic acid, alkoxysulfinic acids, aryloxysulfinic acids, phosphoric acid or acetic acid.
  • solvate is understood to denote the form of the compound of formula (I) when it is associated with a solvent.
  • the solvates include conventional solvates formed during the process of preparation of the compound of formula (I). Examples of solvates are those obtained in the presence of water or of a linear or branched alcohol, in particular ethanol or isopropanol.
  • flavone is understood to denote any compound comprising a 2-phenylchromen-4-one (2-phenyl-l-benzopyran-4-one) structural backbone corresponding to the following formula:
  • flavonol is understood to denote any compound comprising a flavone backbone as defined above and substituted by a hydroxyl group in the 3 position, namely a backbone corresponding to the following formula: [Chem 3]
  • flavonone is understood to denote any compound comprising a flavone backbone as defined above but not comprising an unsaturation in the 2,3 position, namely a backbone corresponding to the following formula: [Chem 4]
  • a fragranced composition according to the invention comprises at least one compound of formula (I), or one of its geometrical isomers, in particular optical isomers, of its tautomers, and also its organic or inorganic acid or base salts, or its solvates, in particular hydrates:
  • ⁇ R 1 represents an atom or a group chosen from: - a hydrogen atom, - a hydroxyl, - a (C 1 -C 6 )alkyl group, - a (C 1 -C 6 )alkoxy group, - a monoglycoside or diglycoside sugar group, such as a glycosyl group, or an -O- monoglycoside or -diglycoside sugar group, such as an -O-glycosyl group;
  • ⁇ R 2 represents a hydrogen atom, a (C 1 -C 6 )alkyl group or a monoglycoside or diglycoside sugar group, such as a glycosyl group,
  • ⁇ R 3 represents a hydrogen atom or a (C1-C6)alkyl group, ⁇ n represents an integer of between 1 and 3 and m represents an integer of between 0 and 3, it being understood that
  • the -OR 2 group(s) is (are) carried by any one of the carbon atoms in the 5 to 8 positions of the flavone, flavonol or flavanone backbone and that the -OR 3 group(s) is (are) carried by any one of the carbon atoms in the 2' to 6' positions of the flavone, flavonol or flavanone backbone.
  • the -OR 2 group(s) is (are) carried by either one of the carbon atoms in the 5 and/or 7 positions.
  • m has the value 2 and the two -OR 2 groups are carried respectively by the carbon atoms in the 5 and 7 positions.
  • the -OR 3 group(s) is (are) carried by any one of the carbon atoms in the 3', 4' and/or 5' positions.
  • n has the value 2 and the two -OR 3 groups are carried respectively by the carbon atoms in the 3' and 4' positions, or n has the value 3 and the three -OR 3 groups are carried respectively by the carbon atoms in the 3', 4' and 5' positions.
  • R 1 represents an atom or a group chosen from: i) hydrogen, ii) a hydroxyl and iii) a glycosyl or -O-glycosyl group.
  • each R 2 independently represents a hydrogen atom or a glycosyl group, preferably a hydrogen atom.
  • each R 3 independently represents a hydrogen atom or a methyl, preferably a hydrogen atom.
  • n and m which are identical or different, independently represent an integer ranging from 1 to 3.
  • the compounds corresponding to the formula (I) belong generically to the family of the flavonoids, more specifically to the families of the flavones, flavonols and flavanones.
  • a composition according to the invention comprises a compound of formula (I) chosen from luteolin, quercetin, myricetin, rutin, hesperidin, narirutin, ⁇ -glycosylrutin, quercitrin, isoquercitrin, morin, hesperetin, chrysin, apigenin, luteolin-7-O-glucoside, 6- hydroxyflavone, 7,8-dihydroxyflavone or tropoflavin, and their mixtures.
  • formula (I) chosen from luteolin, quercetin, myricetin, rutin, hesperidin, narirutin, ⁇ -glycosylrutin, quercitrin, isoquercitrin, morin, hesperetin, chrysin, apigenin, luteolin-7-O-glucoside, 6- hydroxyflavone, 7,8-dihydroxyflavone or tropoflavin
  • the compound of formula (I) is of formula (I') below, or one of its geometrical isomers, of its tautomers, and also its organic or inorganic acid or base salts, or its solvates, in particular hydrates: [Chem 6] in which formula (I'): R represents an atom or a group chosen from: i) a hydrogen atom, ii) a hydroxyl, iii) a monoglycoside or diglycoside sugar group, such as a glycosyl group, or an -O- monoglycoside or -diglycoside sugar group, such as an -O-glycosyl group, preferably a glycosyl group or an -O-glycosyl group, iv) a (C1-C6)alkyl group, and v) a (C 1 -C 6 )alkoxy group, n and m representing, independently of each other, an integer of between 1 and 3, preferably equal
  • m has the value 2 and the two -OH groups are carried respectively by the carbon atoms in the 5 and 7 positions.
  • the -OH group(s) is (are) carried by any one of the carbon atoms in the 3', 4' and/or 5' positions.
  • n has the value 2 and the two -OH groups are carried respectively by the carbon atoms in the 3' and 4' positions, or n has the value 3 and the three -OH groups are carried respectively by the carbon atoms in the 3', 4' and 5' positions.
  • the compounds of formulae (I) and (I') in accordance with the invention are preferably chosen from natural compounds or compounds of natural origin.
  • the composition according to the invention comprises a compound of formula (I) or (I 1 ) chosen from luteolin, quercetin, myricetin, rutin, a-glycosylrutin and their mixtures, more preferentially still chosen from rutin, a-glycosylrutin and their mixtures.
  • the compound of formula (I) is rutin.
  • the compound of formula (I) is a-glycosylrutin.
  • the compounds of formula (I) or (I') can be found in numerous plant extracts, in particular grapes, berries, nuts, the peel of citrus fruits, capers, olives, buckwheat, asparagus, raspberry, blackcurrant, plum, mango, green beans, rhubarb, bilberry, onion, quince, apple, cherry, broccoli, green or black tea leaves, and also plants, such as plants of the genus Citrus, Sophora japonica, Eucalyptus macrorhyncha, wild pansy, white mulberry, parsley, Ginkgo biloba, lovage, elder or Vitis vinifera.
  • the compounds of formulae (I) and (I') can be obtained by any method known to a person skilled in the art, for example by extraction from a plant extract.
  • the compounds of formula (I) or (I') defined above can optionally be introduced into a fragranced composition according to the invention in the form of a plant extract.
  • rutin can be employed in the form of an extract of buds of the plant Sophora japonica.
  • a certain number of compounds of formula (I) or (I') are also available commercially, such as, for example, a-glycosylrutin sold by Qingdao Taitong Pharmaceutical.
  • a fragranced composition according to the invention can comprise from 0.01% to 5.0% by weight of compound(s) of formula (I), in particular from 0.03% to 2.0% by weight, preferably from 0.05% to 1.0% by weight, more preferentially from 0.05% to 0.2% by weight, with respect to the total weight of said composition.
  • a fragranced composition according to the invention can comprise from 0.01% to 0.1% by weight of compound(s) of formula (I), in particular from 0.03% to 0.1% by weight, preferably from 0.05% to 0.1% by weight, with respect to the total weight of said composition.
  • a fragranced composition according to the invention can comprise from 0.05% to 10% by weight of plant extract containing at least one compound of formula (I), with respect to the total weight of said composition.
  • said plant extract(s) is (are) rich in compound(s) of formula (I), namely that they can comprise a content of compound(s) of formula (I) ranging from 80% to 99% by weight, in particular from 85% to 95% by weight, with respect to their total weight.
  • a fragranced composition according to the invention comprises ethanol in a content strictly greater than 15% by weight, with respect to the total weight of the composition.
  • ethanol is commonly used in the field of fragranced compositions as solvent.
  • ethanol can be introduced into the composition in the form of absolute ethanol, namely comprising less than 1% by weight of water, in particular less than 0.5% by weight of water, for example comprising 0.2% by weight of water, with respect to its total weight.
  • the ethanol can be 95° ethanol.
  • the ethanol is of natural origin, in particular of plant origin, namely that it is produced from biomass.
  • Ethanol of natural origin is known as “bioethanol”.
  • a composition according to the invention can comprise a content of (bio)ethanol varying from 16% to 99.5% by weight, in particular from 25% to 97% by weight, more particularly from 35% to 95% by weight, more particularly still from 45% to 90% by weight, with respect to the total weight of the composition.
  • a composition according to the invention can comprise a content of (bio)ethanol ranging from 65% to 80% by weight, for example of 68%, of 70% or of 78% by weight, with respect to the total weight of the composition.
  • a fragranced composition according to the invention comprises at least one water-soluble colorant, also called “ water -soluble dye” .
  • a colorant is capable of colouring the fragranced composition by absorbing in the visible spectrum.
  • the water-soluble colorant is distinct from the compound of formula (I) as defined above.
  • a dye is water-soluble when its solubility in water, measured at 25°C, is at least equal to 0.01 gd.
  • the water-soluble colorant is chosen from water-soluble colorants which are natural or of natural origin.
  • the water-soluble dyes suitable for the invention result from extracts of animals, bacteria, fungi, algae or plants, used in their entirety or partially.
  • the water-soluble dye(s) suitable for the invention preferentially result from extracts of plants or plant parts, such as fruits, including citrus fruits, vegetables, trees or shrubs. Mixtures of these extracts can also be used.
  • the water-soluble colorant can be introduced into a fragranced composition according to the invention in the form of a natural extract.
  • Such extracts can be obtained by extraction of various plant parts, such as, for example, the root, the wood, the bark, the leaf, the flower, the fruit, the pip, the pod or the peel.
  • Mention may be made, among the plant extracts, of extracts of leaves of roses, of gardenias, of Clitoria tematea or blue pea flowers, of turmeric rhizomes or else carrot, sweet potato or radish peelings.
  • Mention may be made, among the extracts of fruits, of extracts of apple, extracts of grape or extracts of cacao tree beans and/or pods.
  • Mention may be made, among the extracts of vegetables, of extracts of potato, of onion peel and of beetroot.
  • Mention may be made, among the extracts of tree wood, of extracts of pine bark or extracts of logwood.
  • water-soluble colorants more particularly suitable for the invention, of water-soluble dyes which are natural or of natural origin, in particular dyes derived from natural ortho -diphenol.
  • the ortho-diphenols which can be used according to the invention are chosen from: flavanols, in particular catechin and epicatechin gallate, pyrans, in particular anthocyanidins, in particular cyanidin, delphinidin and petunidin, anthocyanins or anthocyans, in particular myrtillin or anthocyanosides; ortho-hydroxybenzoates, for example gallic acid salts, hydroxystilbenes, for example 3,3',4,5'-tetrahydroxystilbene, optionally oxylated
  • proanthocyanidins and in particular proanthocyanidins Al, A2, Bl, B2, B3 and Cl proanthocyanidins
  • proanthocyanidins in particular proanthocyanidins Al, A2, Bl, B2, B3 and Cl
  • proanthocyanins proanthocyanins
  • tannic acid gallic acid
  • ellagic acid neoflavanols and neoflavanones
  • haematoxylin of haematin, of brazilin and of brazilein
  • the ortho-diphenols which can be used according to the invention are chosen from anthocyanidins, in particular cyanidin, delphinidin and petunidin; anthocyanins or anthocyans, in particular myrtillin; proanthocyanidins and in particular the proanthocyanidins Al, A2, Bl, B2, B3 and Cl; proanthocyanins; and the mixtures of the preceding compounds.
  • water-soluble colorants more particularly suitable for the invention, of those chosen from: pyran or pyranium dyes, in particular anthocyans and anthocyanosides, preferably extracts of red radish or extracts of sweet potato, in particular purple sweet potato; and - polyene dyes in particular chosen from jasminoids, especially those, the coloured active principles of which have the following formula: [Chem 7] n which: R 11 and R 16 , which are identical or different, represent: ) a cycloalkyl group which is optionally unsaturated and/or optionally substituted by one or more groups chosen from a) oxo, b) hydroxyl and c) (C1-C6)alkyl, preferably (C1- C4)alkyl, in particular methyl; i) a cycloalkylcarbonyl group, the cycloalkyl group of which is optionally unsaturated and/or optionally substituted by one or more groups a)
  • R 8 and R 10 represent a hydroxyl group
  • R 7 represents a hydrogen atom or a (C1- C4)alkoxy group, in particular a methoxy group
  • R 9 represents a hydrogen atom or a (C1- C 4 )alkoxy group, in particular a methoxy group.
  • the water-soluble colorant is chosen from: - pyran or pyranium dyes, in particular anthocyans and anthocyanosides, preferably extracts of red radish or extracts of sweet potato, in particular purple sweet potato; - polyene dyes in particular chosen from jasminoids, especially those, the coloured active principles of which have the following formula: [Chem 9] in which: R 11 and R 16 , which are identical or different, represent: i) a cycloalkyl group which is optionally unsaturated and/or optionally substituted by one or more groups chosen from a) oxo, b) hydroxyl and c) (C1-C6)alkyl, preferably (C1- C 4 )alkyl, in particular methyl; ii) a cycloalkylcarbonyl group, the cycloalkyl group of which is optionally unsaturated and/or optionally substituted by one or more groups a) to c) as
  • phthalocyanins and porphyrins in particular complexed with a metal, preferably a transition metal (such as titanium, manganese, iron, cobalt, nickel, copper or zinc, in particular magnesium or copper), such as chlorophyll, chlorophyllin and their metal complexes, in particular their transition metal complexes, especially of titanium, manganese, iron, cobalt, nickel, copper or zinc, in particular magnesium or copper, preferably copper.
  • a transition metal such as titanium, manganese, iron, cobalt, nickel, copper or zinc, in particular magnesium or copper
  • a water-soluble colorant suitable for the invention can be chosen from: i) paprika, in particular that sold under the name Capsanthin/Capsorubin by Vitiva; ii) ⁇ -carotene, in particular that sold under the name Beta-Carotene by Vitiva; iii) extract of red radish, in particular that sold under the name Raphanus sativus Root Extract by Vitiva, the colouring active principle of which is enocyanin; iv) extract of purple sweet potato, in particular that sold under the name Anthocyanins/Ipomoeia batatas Root Extract by Vitiva, which is an extract of the roots of Ipomoea batatas, Convolvulacaea; v) yellow gardenia, in particular that sold under the name Gardenia Yellow - Gardenia jasminoides Fruit Extract by Henan Zhongda Biological; vi) red gardenia, in particular that sold under the name Gardenia Fruit Extract For Water So
  • the water-soluble colorant is chosen from pyran dyes, polyene dyes, red, blue or yellow gardenia extracts, carotenes, paprika, curcumin and their mixtures, in particular from paprika, ⁇ -carotene, red radish extract, purple sweet potato extract, yellow, red or blue gardenia, curcumin, blue pea extract and their mixtures.
  • the colorant(s) of the invention is (are) chosen from organic pigments.
  • the organic pigments of the invention Mention may be made, among the organic pigments of the invention, of carbon black, pigments of D & C type (in particular of azo, anthraquinone, nitro and triarylmethane form) and lakes based on cochineal carmine of barium, strontium, calcium and aluminium, preferably pigments of D & C type.
  • the colorant(s) of the invention is (are) chosen from water-soluble anionic, cationic, zwitterionic or neutral dyes and more particularly anionic dyes (i.e., commonly referred to as "acid" direct dyes for their affinity with alkaline substances).
  • anionic dyes is understood to mean any dye comprising, in its structure, at least one CO 2 R' or SO 3 R' substituent with R' denoting a hydrogen atom or a cation originating from a metal or from an amine, or an ammonium ion.
  • the anionic dyes can be chosen from acid nitro direct dyes, acid azo dyes, acid azine dyes, acid triarylmethane dyes, acid indoamine dyes, acid anthraquinone dyes, indigoids and acid natural dyes.
  • anionic dyes suitable for the invention of the dyes chosen from those of following formulae (G), (G'), (J), (J'), (K), (K'), (L) and (M) and their mixtures, in particular of formulae (G), (J) and (L) and their mixtures: a) the anionic azo dyes of formulae (G) and (G') below: [Chem 11] in which formulae R 7 , R 8 , R 9 , R 10 , R' 7 , R' 8 , R' 9 and R' 10 , which are identical or different, represent a hydrogen or halogen atom or a group chosen from: - alkyl; - alkoxy, alkylthio; - hydroxyl, mercapto; - nitro, nitroso; - R°-C(X)-X'-, R°-X'-C(X)- or R°-X'-C(X)-X''- with R° representing
  • Ar-N N- with Ar representing an optionally substituted aryl group; preferentially a phenyl optionally substituted by one or more alkyl, M + (0')S(0)2- or phenylamino groups; or else two contiguous groups R7 with Rs or Rs with R9 or R9 with Rio together form a fused benzo group A'; and R'7 with R's or R's with R'9 or R'9 with R'10 together form a fused benzo group B'; with A' and B' optionally substituted by one or more groups chosen from nitro; nitroso; M + (0')S(0)2-; hydroxyl; mercapto; (di)(alkyl)amino; R°-C(X)-X'-; R°- X'-C(X)-; R°-X'-C(X)-X"-;
  • Ar-N N- and ary l(alkyl) amino which is optionally substituted; with M + , R°, X, X', X" and Ar as defined above; and in which:
  • W represents a sigma c bond, an oxygen or sulfur atom, or a divalent -NR- radical with R as defined above or methylene -C(Ra)(Rb)- radical with Ra and Rb, which are identical or different, representing a hydrogen atom or an aryl group, or else Ra and Rb form, together with the carbon atom which carries them, a spiro cycloalkyl; preferentially, W represents a sulfur atom or Ra and Rb together form a cyclohexyl; it being understood that the formulae (G) and (G') comprise at least one sulfonate M + (O" )S(O)2- radical or one carboxylate M + (O')CO- radical on one of the rings A, A', B, B' or C; preferentially sodium sulfonate.
  • dyes of formula (G) Mention may be made, as examples of dyes of formula (G), of: Acid Red 1, Acid Red 4, Acid Red 13, Acid Red 14, Acid Red 18, Acid Red 27, Acid Red 28, Acid Red 32, Acid Red 33, Acid Red 35, Acid Red 37, Acid Red 40, Acid Red 41, Acid Red 42, Acid Red 44, Pigment Red 57, Acid Red 68, Acid Red 73, Acid Red 135, Acid Red 138, Acid Red 184, Food Red 1, Food Red 13, Orange 4, Acid Orange 6, Acid Orange 7, Acid Orange 10, Acid Orange 19, Acid Orange 20, Acid Orange 24, Yellow 6, Acid Yellow 9, Acid Yellow 36, Acid Yellow 199, Food Yellow 3; Acid Violet 7, Acid Violet 14, Acid Blue 113, Acid Blue 117, Acid Black 1, Acid Brown 4, Acid Brown 20, Acid Black 26, Acid Black 52, Food Black 1, Food Black 2; Food Yellow 3 or Sunset Yellow; and mention may be made, as examples of dyes of formula (G'), of: Acid Red 111, Acid Red 134, Acid Yellow 38; b) the anthraquinone dyes of formulae (J) and (J'
  • Z' represents a hydrogen atom or an NR28R29 group with R28 and R29, which are identical or different, representing a hydrogen atom or a group chosen from: alkyl; polyhydroxyalkyl, such as hydroxyethyl; aryl optionally substituted by one or more groups, particularly i) alkyl, such as methyl, n-dodecyl or n-butyl; ii) M + (0')S(0)2- with M + as defined above; iii) R°-C(X)-X'-, R°-X'-C(X)-, R°-X'-C(X)-X"- with R°, X, X' and X" as defined above; preferentially, R° represents an alkyl group; cycloalkyl; in particular cyclohexyl;
  • Z represents a group chosen from hydroxyl and NR'28R'29 with R'28 and R'29, which are identical or different, representing the same atoms or groups as R28 and R29 as defined above; it being understood that the formulae (J) and (J') comprise at least one sulfonate M + (O" )S(O)2- radical or one carboxylate M + (O')CO- radical; preferentially sodium sulfonate.
  • dyes of formula (J) of: Acid Blue 25, Acid Blue 43, Acid Blue 62, Acid Blue 78, Acid Blue 129, Acid Blue 138, Acid Blue 140, Acid Blue 251, Acid Green 25, Acid Green 41, Acid Violet 42, Acid Violet 43, Mordant Red 3; EXT Violet No. 2; and mention may be made, as an example of a dye of formula (J'), of: Acid Black 48; d) the nitro dyes of formulae (K) and (K') below:
  • R30, R31 and R32 which are identical or different, represent a hydrogen or halogen atom or a group chosen from: alkyl; alkoxy optionally substituted by one or more hydroxyl groups, alkylthio optionally substituted by one or more hydroxyl groups; hydroxyl, mercapto; nitro, nitroso; polyhaloalkyl;
  • Rc and Rd which are identical or different, represent a hydrogen atom or an alkyl group
  • W is as defined above; W particularly represents an -NH- group;
  • ALK represents a linear or branched divalent Ci-Ce alkylene group; in particular, ALK represents a -CH2-CH2- group; n has the value 1 or 2; p represents an integer of between 1 and 5 inclusive; q represents an integer of between 1 and 4 inclusive; u has the value 0 or 1 ; when n has the value 1, J represents a nitro or nitroso group; particularly a nitro group; when n has the value 2, J represents an oxygen or sulfur atom or a divalent - S(O) m — radical with m representing an integer 1 or 2; preferentially, J represents an -SO2- radical;
  • M' represents a hydrogen atom or a cationic counterion
  • [Chem 17] which is present or absent, represents a benzo group optionally substituted by one or more R30 groups as defined above; it being understood that the formulae (K) and (K') comprise at least one sulfonate M + (O" )S(O)2- radical or one carboxylate M + (O')CO- radical; preferentially sodium sulfonate.
  • dyes of formula (K), of: Acid Brown 13 and Acid Orange 3 Mention may be made, as examples of dyes of formula (K'), of: Acid Yellow 1, the sodium salt of 2,4-dinitro-l-naphthol-7-sulfonic acid, 2-piperidino-5- nitrobenzenesulfonic acid, 2-(4'-N,N-(2"-hydroxyethyl)amino-2'- nitro)anilineethanesulfonic acid, 4-P-hydroxyethylamino-3-nitrobenzenesulfonic acid; EXT D&C Yellow 7; e) the triarylmethane dyes of formula (L) below:
  • R33, R34, R35 and R36 which are identical or different, represent a hydrogen atom or a group chosen from alkyl, optionally substituted aryl and optionally substituted arylalkyl; particularly an alkyl and benzyl group optionally substituted by an M + (O')S(O) m - group with M + and m as defined above;
  • R37, R38, R39, R40, R41, R42, R43 and R44 which are identical or different, represent a hydrogen atom or a group chosen from: alkyl; alkoxy, alkylthio;
  • X, X' and X" which are identical or different, representing an oxygen or sulfur atom or NR, with R representing a hydrogen atom or an alkyl group;
  • R41 with R42 or R42 with R43 or R43 with R44 together form a fused benzo group: I'; with I' optionally substituted by one or more groups chosen from nitro; nitroso; M + (O')S(O)2-; hydroxyl; mercapto; (di)(alkyl)amino; R°-C(X)-X'-; R°- X'-C(X)- and R°-X'-C(X)-X"-; with M + , R°, X, X' and X" as defined above; in particular, R37 to R40 represent a hydrogen atom, and R41 to R44, which are identical or different, represent a hydroxyl or M + (O')S(O)2- group; and when R43 with R44 together form a benzo group, it is preferentially substituted by an (O')S(O)2- group; it being understood
  • G represents an oxygen or sulfur atom or an NRe group with Re representing a hydrogen atom or an alkyl group; in particular, G represents an oxygen atom;
  • L represents an alkoxide M + O"; a thioalkoxide M + S" or an NRf group, with Rf representing a hydrogen atom or an alkyl group, and M + as defined above; M + is particularly sodium or potassium;
  • L' represents an oxygen or sulfur atom or an ammonium group: N + RfRg, with Rf and Rg, which are identical or different, representing a hydrogen atom or an optionally substituted alkyl or aryl group; L' particularly represents an oxygen atom or a phenylamino group optionally substituted by one or more alkyl or M + (O')S(O) m - groups with m and M + as defined above;
  • Q and Q' which are identical or different, represent an oxygen or sulfur atom; in particular, Q and Q' represent an oxygen atom;
  • colorants suitable for the invention of synthetic or natural water-soluble dyes, such as, for example, FDC Red 4, DC Red 6, DC Red 22, DC Red 28, DC Red 30, DC Red 33, DC Orange 4, DC Yellow 5, DC Yellow 6, DC Yellow 8, FDC Green 3, DC Green 5, FDC Blue 1 and their mixtures, more preferentially chosen from FDC Red 4, DC Red 33, DC Orange 4, DC Yellow 5, DC Green 5 and FDC Blue 1, and also their mixtures.
  • water-soluble dyes suitable for the invention of synthetic or natural water-soluble dyes, such as, for example, FDC Red 4, DC Red 6, DC Red 22, DC Red 28, DC Red 30, DC Red 33, DC Orange 4, DC Yellow 5, DC Yellow 6, DC Yellow 8, FDC Green 3, DC Green 5, FDC Blue 1, betanin (beetroot), carmine, copper chlorophyllin, methylene blue, ortho -diphenol derivatives, in particular anthocyanins (red radish, red cabbage, purple sweet potato, purple maize, black carrot, hibiscus, blue pea or elder), caramel, sandalwood, gardenia, spirulina and riboflavin.
  • synthetic or natural water-soluble dyes such as, for example, FDC Red 4, DC Red 6, DC Red 22, DC Red 28, DC Red 30, DC Red 33, DC Orange 4, DC Yellow 5, DC Yellow 6, DC Yellow 8, FDC Green 3, DC Green 5, FDC Blue 1, betanin (beetroot), carmine, copper chlorophyllin, methylene blue, ortho -diphenol derivatives
  • the water-soluble colorants suitable for the invention can be in the form of salts of acids or of bases, in particular inorganic or organic acids, in particular hydrochloric acid, or inorganic or organic bases, such as alkali metal hydroxides, including sodium hydroxide.
  • the water-soluble colorants suitable for the invention can be glycosylated, that is to say comprise one or more glycosyl groups.
  • the water-soluble colorant, in particular resulting from natural extract(s), suitable for the invention can be provided in any form which makes possible its dissolution in the fragranced composition, in particular in an aqueous, alcoholic or aqueous/alcoholic medium. It can in particular be in powder or liquid form, preferably in powder form.
  • the amount of water-soluble colorants(s) present in a composition according to the invention is liable to vary significantly from the viewpoint of the tint or the chromatic intensity sought by its presence.
  • the water-soluble colorant(s) present in the composition according to the invention represent(s) from 0.0001% to 20% by weight of the total weight of the composition(s) containing the colorant(s) or the extract(s) containing them.
  • the content in the fragrancing composition containing them preferably varies from 0.0001% to 5% by weight, preferably from 0.001% to 3.0% by weight, more preferentially from 0.01% to 1.0% by weight and more preferentially still from 0.1% to 0.5% by weight of water-soluble colorant(s), with respect to the total weight of said composition.
  • the total amount of water-soluble colorant(s) contained in the composition varies from 1 to 300 ppm (part(s) per million) and more particularly from 1 to 200 ppm.
  • a content of water-soluble colorant(s) of less than or equal to 300 ppm in the fragranced coloured composition makes it possible to prevent the formation of marks during its application, in particular on clothing, this being the case whatever the colorant employed.
  • the water-soluble colorant can be introduced into the fragranced composition of the invention in the form of a natural extract.
  • a fragranced composition according to the invention can comprise from 0.05% to 15% by weight of natural extract comprising a water-soluble colorant, with respect to the total weight of said composition.
  • a composition according to the invention comprises from 0.0001% to 20% by weight of the water-soluble colorant(s), with respect to the total weight of the composition containing the colorant(s) or the extract(s) containing them, preferably:
  • the content in the fragrancing composition varies from 0.0001% to 5% by weight, preferably from 0.001% to 3.0% by weight, more preferentially from 0.01% to 1.0% by weight and more preferentially still from 0.1% to 0.5% by weight of the water-soluble colorant(s), with respect to the total weight of said composition;
  • the content of extract(s) in the composition varies from 0.01% to 20% by weight, particularly from 0.1% to 10% by weight, particularly from 0.2% to 8.0% by weight, preferentially from 0.3% to 3.0% by weight and more preferentially from 0.4% to 2.0% by weight, better still from 0.5% to 1% by weight, of extract(s) in said composition, with respect to the total weight of said composition.
  • a fragranced composition according to the invention comprises at least one fragrancing substance.
  • Fragrances are compositions containing in particular 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.
  • a fragranced composition according to the invention preferably comprises at least one fragrancing substance chosen from essential oils, fragrances and aromas of synthetic or natural origin, and their mixtures.
  • They can be natural products, such as essential oils, absolutes, resinoids, resins, concretes and/or synthetic products, such as terpene or sesquiterpene hydrocarbons, alcohols, phenols, aldehydes, ketones, ethers, acids, esters, nitriles or peroxides, which are saturated or unsaturated, aliphatic or cyclic.
  • 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 by an appropriate mechanical process without heating (cold expression).
  • the essential oil is generally separated from the aqueous phase by a physical process which does not result in any significant change in the composition.
  • the choice of the method for obtaining the essential oils depends mainly on the starting material: its original state and its characteristics, its intrinsic nature.
  • the “ essential oil/plant starting material” yield can be extremely variable depending on the plants: 15 ppm to more than 20%. This choice determines the characteristics of the essential oil, in particular viscosity, colour, solubility, volatility, and enrichment or depletion in certain constituents.
  • Steam distillation corresponds to the vaporization, in the presence of steam, of a sparingly water-miscible substance. The starting material is placed in contact with boiling water or steam in a still.
  • the steam entrains the essential oil vapour, which is condensed in the condenser in order to be recovered as liquid phase in a Florentine flask (or essence jar), where the essential oil is separated from the water by settling.
  • the aqueous distillate which remains in the steam distillation, once the essential oil has been separated, is known as the “aromatic water” or “hydrolate” or “distilled floral water”.
  • Production by dry distillation consists in obtaining the essential oil by distillation of wood, bark or roots, without addition of water or steam, in a closed chamber designed in order for the liquid to be recovered in its bottom part.
  • Cade oil is the most well known example of this method of production.
  • the cold expression production method is applied only to citrus fruits (Citrus spp.) by mechanical processes at ambient temperature.
  • the principle of the method is as follows: the peel is shredded and the contents of the secretory cavities which have been ruptured are recovered by a physical process.
  • the conventional process consists in exerting an abrasive action over the entire surface of the fruit under a stream of water. After removal of the solid waste, the essential oil is separated from the aqueous phase by centrifugation.
  • the majority of industrial plants in fact allow the simultaneous or sequential recovery of the fruit juices and of the essential oil.
  • Essential oils are generally volatile and liquid at ambient temperature, which differentiates them from “fixed” oils. They are more or less coloured and their density is generally lower than that of water. They have a high refractive index and the majority deviate polarized light. They are soluble in fats and in standard organic solvents, can be steam distilled and exhibit a very low solubility in water.
  • John’s wort Iridaceae; Juglandaceae; Lamiaceae, for example thyme, oregano, Monarda, savory, basil, marjorams, mints, patchouli, lavenders, sages, catnip, rosemary, hyssop or balm; Lauraceae, for example Ravensara, bay, rosewood, cinnamon, Litsea; Liliaceae, for example garlic; Magnoliaceae, for example magnolia; Malvaceae; Meliaceae; Monimiaceae; Moraceae, for example hemp or hop; Myricaceae; Myristicaceae, for example nutmeg; Myrtaceae, for example eucalyptus, tea tree, Melaleuca quinquenervia, cajuput, Backhousia, clove, myrtle; Oleaceae; Piperaceae, for example pepper; Pittosporaceae; Poaceae, for example citronella grass
  • fragrancing substances are in particular: geraniol, geranyl acetate, farnesol, borneol, bornyl acetate, linalol, linalyl acetate, linalyl propionate, linalyl butyrate, tetrahydrolinalol, 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 salicylate, di
  • the fragranced composition comprises at least 1% by weight of a mixture of fragrancing substances, in particular of at least two distinct fragrancing substances, with respect to the total weight of the composition, and preferably of at least three distinct fragrancing substances.
  • the fragrancing substances will preferably be chosen so that they produce notes (top, middle and base) in the following families: hesperidic, aromatic, floral notes, in particular pink flowers and white flowers, spicy, woody, investigating, chypre, fougere, leather and musk.
  • the amount of fragrancing substance(s) present in a composition according to the invention is liable to vary significantly from the viewpoint of the odour or of the odorous intensity sought by its presence.
  • a fragranced composition according to the invention can comprise from 0.0001% to 10% by weight, particularly from 0.001% to 8.0% by weight, more particularly from 0.01% to 5.0% by weight, preferentially from 0.1% to 1.0% by weight, of fragrancing substance(s), with respect to the total weight of said composition.
  • the fragrancing substances can be introduced into a fragranced composition in accordance with the invention in the form of a fragrance concentrate.
  • the fragrance concentrate can be a concrete or an absolute, preferably an absolute.
  • a fragranced composition according to the invention comprises in particular from 1.0% to 50% by weight of fragrance concentrate, more particularly from 2.0% to 40% by weight, preferentially from 5.0% to 30% by weight, more preferentially from 10% to 20% by weight, for example 15% by weight, with respect to the total weight of the composition.
  • a fragranced composition according to the invention can be provided in any presentation form conventionally used for a topical application and in particular in the form of an alcoholic or aqueous/alcoholic solution or suspension, of an emulsion of liquid or semiliquid consistency of the milk type, which are obtained by dispersion of a fatty phase in an aqueous phase (O/W) or vice versa (W/O), or of a suspension or emulsion of soft consistency of (O/W) or (W/O) cream type, or of an anhydrous gel, or of any other cosmetic form.
  • an alcoholic or aqueous/alcoholic solution or suspension of an emulsion of liquid or semiliquid consistency of the milk type, which are obtained by dispersion of a fatty phase in an aqueous phase (O/W) or vice versa (W/O), or of a suspension or emulsion of soft consistency of (O/W) or (W/O) cream type, or of an anhydrous gel, or of any other cosmetic form.
  • a fragranced composition according to the invention is an alcoholic composition, namely a composition comprising an alcohol or a mixture of alcohols as solvent(s), or an aqueous/alcoholic composition, namely a composition comprising a mixture of water and of alcohol as solvents.
  • a fragranced composition according to the invention is an alcoholic or aqueous/alcoholic composition; preferably, the composition comprises as solvent(s) ethanol, optionally as a mixture with water and/or pentylene glycol.
  • the composition according to the invention is aqueous/alcoholic.
  • composition according to the invention can additionally comprise other alcohols distinct from ethanol, referred to as “additional alcohols”.
  • the additional alcohols very particularly suitable for the invention are chosen from i) monoalcohols having from 3 to 6 carbon atoms, such as isopropanol, and ii) glycols having from 2 to 8 carbon atoms, such as ethylene glycol, propylene glycol, 1,3 -butylene glycol, pentylene glycol and dipropylene glycol.
  • a fragranced composition according to the invention comprises, as solvent(s), water and (bio)ethanol, optionally as a mixture with pentylene glycol.
  • the composition of the invention comprises a content of additional alcohols ranging from 0.01% to 80% by weight, particularly from 0.01% to 50% by weight.
  • a composition according to the invention is preferably aqueous/alcoholic.
  • An aqueous/alcoholic fragranced composition according to the invention can comprise, besides water and ethanol, one or more water-soluble solvents distinct from the additional alcohols defined above.
  • water-soluble solvent denotes a compound which is liquid at ambient temperature and miscible with water (miscibility in water of greater than 50% by weight at a temperature ranging from 20°C to 25°C and atmospheric pressure).
  • the water-soluble solvents which can be used in the composition of the invention can additionally be volatile. Mention may in particular be made, among the water-soluble solvents which can be used in the composition in accordance with the invention, of C3 and C4 ketones and C2-C4 aldehydes.
  • a fragranced composition according to the invention can be anhydrous, namely that it comprises less than 2% by weight of water, preferably less than 1% by weight of water, preferentially less than 0.5% by weight of water, indeed even is totally devoid of water.
  • a fragranced composition according to the invention can also comprise at least one C2-C32 polyol.
  • polyol should be understood as meaning any organic molecule comprising at least three free hydroxyl (-OH) groups.
  • a polyol in accordance with the present invention is present in liquid form at ambient temperature.
  • a polyol suitable for the invention can be a compound of saturated or unsaturated and linear, branched or cyclic alkyl type carrying, on the alkyl chain, at least three -OH functions, in particular at least four -OH functions.
  • the polyols advantageously suitable for the formulation of a composition according to the present invention are those exhibiting in particular from 2 to 32 carbon atoms, preferably from 3 to 16 carbon atoms.
  • the polyol can, for example, be chosen from pentaerythritol, trimethylolpropane, glycerol, polyglycerols, in particular glycerol oligomers, preferably diglycerol, and their mixtures.
  • a fragranced composition according to the invention can comprise one or more fatty substances which are liquid at ambient temperature and/or a fatty substance which is solid at ambient temperature, such as waxes, pasty fatty substances, gums and their mixtures.
  • ambient temperature is understood to mean a temperature equal to 25°C.
  • the fatty substances suitable for the present invention are liquid at ambient temperature and at atmospheric pressure.
  • the oils can be polar or non-polar, of different chemical natures, alone or as a mixture.
  • polar oils of: hydrocarbon vegetable oils having a high content of triglycerides constituted of esters of fatty acids and of glycerol, for example like wheat germ oil, maize oil, sunflower oil, shea oil, castor oil and sweet almond oil; synthetic esters and ethers; saturated C12 to C26 fatty alcohols; and their mixtures.
  • non-polar oils can be chosen in particular from silicone oils, such as volatile or non-volatile, linear or cyclic, polydimethylsiloxanes which are liquid at ambient temperature (20°C ⁇ 5°C) and atmospheric pressure, and linear or branched hydrocarbons of synthetic or mineral origin.
  • the fatty substances are vegetable oils. Mention may be made, as vegetable oils, of sunflower oil, virgin olive oil, refined sesame oil, and the like.
  • a fragranced composition according to the invention can also comprise one or more anionic, cationic, non-ionic, zwitterionic or amphoteric surfactants.
  • esters of fatty acid and of sugars in particular those chosen from the group consisting of esters or mixtures of esters of C8-C22 fatty acid and of sucrose, of maltose, of glucose or of fructose, and esters or mixtures of esters of C14-C22 fatty acid and of methyl glucose.
  • esters or of mixtures of esters of fatty acid and of sucrose of maltose, of glucose or of fructose, of sucrose monostearate, sucrose distearate, sucrose tristearate and their mixtures, and, as examples of esters or of mixtures of esters of fatty acid and of methyl glucose, of Polyglyceryl-3 Methylglucose Distearate, sold by Goldschmidt under the name Tego-Care 450.
  • the fragranced composition according to the invention can comprise one or more co-emulsifiers.
  • This or these co-emulsifiers can be chosen, for example, from C16-C22 fatty alcohols or esters of C3-C6 polyols with C14-C22 fatty acids, and their mixtures. Mention may be made, as co-emulsifiers, for example, of cetyl alcohol, stearyl alcohol, cetearyl alcohol (mixture of cetyl alcohol and of stearyl alcohol), glyceryl stearate and their mixtures, and preferably cetyl alcohol.
  • a fragranced composition can comprise from 0.01% to 10% by weight, more particularly from 0.1% to 5% by weight, and preferentially comprises from 1% to 3% by weight, of surfactant(s), with respect to the total weight of the fragranced composition.
  • a fragranced composition according to the invention can additionally comprise at least one preservative.
  • preservative or “preserving agent” is understood to mean any cosmetically or pharmaceutically acceptable compound which makes it possible to prevent microbial growth (or the growth of microorganisms) which can take place in cosmetic or pharmaceutical compositions, from the moment of their preparation, while they are in storage and up to the time of their conventional use by consumers. Mention may in particular be made, as preservatives, of the preservatives described in Cosmetics, Kirk-Othmer Encyclopedia of Chemical Technology, John Wiley & Sons Inc., Martin M. Rieger; 5.2 Preservatives & Table 3, 04/12/2000, https://doi.org/10.1002/all0471238961.0315191318090507.a01.
  • the preservative(s) are chosen from organic preservatives having an aromatic group.
  • a fragranced composition according to the invention can additionally comprise at least one preservative, in particular chosen from i) benzenecarboxylic acids optionally substituted on the phenyl group by one or more groups chosen from hydroxyl, (Ci-Cio)alkyl and (Ci- Cio)alkylcarbonyl, and also their salts of bases, in particular of alkali metals and alkaline earth metals, ii) hydroxybenzoic acid esters optionally substituted on the phenyl group by one or more groups chosen from (Ci-Cio)alkyl, such as parabens, in particular methylparaben and ethylparaben and propylparaben, and iii) aromatic alcohols.
  • preservative in particular chosen from i) benzenecarboxylic acids optionally substituted on the phenyl group by one or more groups chosen from hydroxyl, (Ci-Cio)alkyl and (Ci- Cio)alkyl
  • the preservative(s) other than a) are chosen from i) and in particular benzoic acid [CAS No. 65-85-0] and also its salts of bases, in particular of alkali metals and alkaline earth metals; and also salicylic acid optionally substituted by a (Ci-Cs)alkylcarbonyl group, preferably salicylic acid.
  • the preservative(s) are in particular chosen from aryl(Ci-C6)alkanols and aryloxy(Ci-C6)alkanols, such as phenylethanol, parabens, such as propylparaben, methylparaben, butylparaben, ethylparaben or isobutylparaben, benzyl alcohol and/or chlorophenesin.
  • a fragranced composition according to the invention can also comprise at least one organic or inorganic alkaline agent, for example an amine, in particular a (C2-C6)alkanolamine, in particular 2-amino-2-methyl-l -propanol, or an inorganic alkaline agent, such as, for example, alkali metal or alkaline earth metal hydroxides, such as sodium hydroxide.
  • organic or inorganic alkaline agent for example an amine, in particular a (C2-C6)alkanolamine, in particular 2-amino-2-methyl-l -propanol
  • an inorganic alkaline agent such as, for example, alkali metal or alkaline earth metal hydroxides, such as sodium hydroxide.
  • the composition comprises one or more chelating agents.
  • chelating agent is understood to mean a ligand or chelating agent which makes it possible to form a metal complex, referred to as chelate, with a metal cation or atom.
  • the chelating agent is electron-donating and the chelated entity is electrondeficient.
  • a “chelate” differs from a simple “complex” in that the metal cation is attached to the chelating ligand or chelating agent via at least two coordination bonds. The metal is thus “gripped” between the chemical functions of the ligand.
  • the number of metal-ligand bonds of a ligand molecule defines the “denticity”: such coordinates or ligands are referred to as being bidentate, tridentate or tetradentate.
  • the central atom is bonded to the neighbouring atoms via at least two bonds, forming a ring structure, a chelate ring.
  • the most stable chelate rings are 5- and 6-membered chelate rings.
  • the chelating agent(s) are chosen from aminocarboxylic acids, for example ethylenediaminetetraacetic acid (EDTA), aminotriacetic acid, diethylenetriaminepentaacetic acid, and their salts, in particular alkaline salts, such as disodium EDTA or dipotassium EDTA, aminopoly carboxy lie acids, such as ethylenediaminedisuccinic acid (EDDS), and their salts, in particular alkaline salts, or else one or more phosphate -based chelating agents, such as alkali metal metaphosphates, such as sodium metaphosphate, alkali metal hexametaphosphates, such as sodium hexametaphosphate, tetra-alkaline pyrophosphates, such as tetrapotassium pyrophosphate, phosphorus-containing acids, such as phytic acid, and their salts, in particular alkaline or alkaline earth salts, such as ethylenediaminetet
  • the composition of the invention comprises one or more metal salts, metal complexes, metal oxides, metal oxoanions, the hydrates and their supported forms.
  • composition according to the invention comprises one or more metal salts.
  • the metal(s) are of oxidation state I or II, more particularly II, preferably chosen from 1) Cu, 2) Fe, 3) Zn, 4) Mg and 5) Mn.
  • metal salt is understood to mean a compound other than alloys, i.e. the salt is constituted of a metal combined with certain non-metal elements.
  • metal salts derives from an oxidative attack.
  • the metal is oxidized to give a cationic entity and then combines with an anionic entity to give a salt.
  • This formation takes place by applying redox principles and the redox reaction (chemical reaction during which an electron transfer takes place in which the atom which captures the electrons is known as the “oxidizing agent”; the atom that gives up the electrons is known as the “reducing agent”); or via chemical exchange reactions between one salt and another salt or an acid, in the presence or absence of atmospheric oxygen. These reactions are known to a person skilled in the art.
  • the salts according to the invention are soluble in water at a proportion of at least 0.0001 gd.
  • the metal salts according to the invention can be introduced in solid form into the compositions or else originate from a mineral or thermal natural water which is rich in these ions, or also from seawater (in particular Dead Sea water). They can also originate from mineral compounds, such as plant extracts containing them (cf., for example, the document FR 2 814 943).
  • metal complex or “coordination compounds'” is understood to mean systems in which the metal ion, the central atom, is chemically bonded to one or more electron donors (ligands).
  • a ligand comprising various coordinating groups (groups capable of coordinating with a metal) gives metal compounds corresponding to principles of a coordination sphere having a predetermined number of electrons (internal complexes or chelates), as described in Ullmann’s Encyclopedia of Industrial Chemistry, “Metal complex dyes”, 2005, pages 1- 42.
  • metal complex is understood to mean: i) metal dyes or “metal-complex dyes”, which are complexed dyes resulting from azo, azomethine, hydrazono or formazan dyes (free, bidentate, tridentate, tetradentate), such as those described in Ullmann’s Encyclopedia of Industrial Chemistry, “Metal complex dyes”, 2005, pages 1-42, which preferentially comprise Cu and Mg; ii) compounds of “aza[18]annulene” type, also known as “(metallo)porphyrins” and “phthalocyanines” , which contain 4 and 8 nitrogen atoms respectively included in the perimeter of the macrocycle, as described in the work “Color Chemistry”, H.
  • the metal ion is then found at the centre of said macrocycle bonded by coordination with two hydrogen atoms to the nitrogen atoms of pyrroles, it also being possible for the metal to be stabilized by one or more bidentate or non-bidentate ligands, the metal ion preferentially being Mg 2+ or Cu 2+ ; the metal complex is particularly:
  • a “metalloporphyrin” constituted of a backbone having 4 pyrrole groups that are connected at their a, a’ positions via 4 methine groups and contain 16 sp 2 hybridized atoms, complexing a metal such as Cu or Mg, or
  • metal oxide(s) is understood to mean compounds of generic formula A A O V with A representing a metal element, x being greater than or equal to 1 and less than or equal to 4, and y being greater than or equal to 1 and less than or equal to 12.
  • metal oxoanion(s) is understood to mean compounds of generic formula Z Z AAOI with A representing a metal element, Z representing an alkali metal, such as Li, Na or K, or a hydrogen atom or an ammonium ion, z being greater than or equal to 1 and less than or equal to 6, x being greater than or equal to 1 and less than or equal to 4, and y being greater than or equal to 1 and less than or equal to 12.
  • supported form(s) is understood to mean the forms where the metal derivative b) is impregnated onto a material known as a “support”.
  • the optional supports of these metal derivatives can be chosen from charcoal, silica, alumina, optionally charged polymers comprising counter-anions or counter-cations (counter-cation or counter-anion of the metal entity).
  • the polymers can be polyethylene glycol (PEG).
  • the metal salt(s) are chosen from the (poly)hydroxy(Ci-Ci6)alkylcarboxylates of metals of oxidation state II, in particular Fe(II), Cu(II), Zn(II), Mg(II) and Mn(II) (poly)hydroxy(Ci-Ci6)alkylcarboxylates.
  • the metal salt(s) are chosen from Cu gluconate, Fe gluconate, Zn gluconate or Mg gluconate, gluconates of metals of oxidation state II, such as Fe, Cu, Zn or Mg gluconates, or lactates of metals of oxidation state II, such as Fe, Cu, Zn or Mg lactates.
  • the metal salts are Fe, Cu, Mg or Zn gluconate, preferably Fe gluconate and Cu gluconate.
  • a fragranced composition according to the invention can also comprise at least one aqueous pH buffer, namely at least one compound which makes it possible to maintain a constant pH in aqueous solution.
  • the aqueous pH buffer(s) particularly suitable for the invention can be chosen from benzoic acid, maleic acid, fumaric acid, succinic acid and their salts, in particular alkali metal or alkaline earth metal salts, for example sodium benzoate.
  • a fragranced composition according to the invention can also comprise one or more additional colorants, distinct from the water-soluble dyes defined above.
  • This (or these) colorant(s) is (or are) preferably chosen from fat-soluble dyes, particulate colorants and their mixtures.
  • 'fat-soluble dye is understood to denote any natural or synthetic, generally organic, dye soluble in an oily phase or solvents miscible with a fatty substance.
  • the particulate colorants can be coloured pigments (i.e., other than the pigment UV screening agents), pearlescent agents and/or particles having metallic glints.
  • pigments is understood to denote white or coloured and inorganic or organic solid particles.
  • Pigments are naturally insoluble in the liquid hydrophilic and lipophilic phases usually employed in cosmetics. Alternatively, they can be rendered insoluble by formulation in lake form, if appropriate.
  • the pigment has little or no solubility in aqueous/alcoholic media.
  • the pigments can be white or coloured, inorganic and/or organic, and coated or uncoated. Mention may be made, among the inorganic pigments, of metal oxides, in particular titanium dioxide, optionally surface-treated, zirconium oxide, zinc oxide or cerium oxide, and also iron oxide, titanium oxide or chromium oxide, manganese violet, ultramarine blue, chromium hydrate and ferric blue.
  • metal oxides in particular titanium dioxide, optionally surface-treated, zirconium oxide, zinc oxide or cerium oxide, and also iron oxide, titanium oxide or chromium oxide, manganese violet, ultramarine blue, chromium hydrate and ferric blue.
  • These additional colorants can be present in a content ranging from 0.01% to 30% by weight, with respect to the total weight of the composition, in particular from 0.05% to 20% by weight, with respect to the total weight of the composition.
  • a fragranced composition according to the invention can additionally comprise any adjuvant usually used in the field of fragrances, such as, for example, emollients or softeners, in particular sweet almond oil or apricot kernel oil, moisturizing agents, in particular glycerol, soothing agents, in particular a-bisabolol, allantoin and Aloe vera; vitamins and their derivatives, essential fatty acids, propellants, peptizing agents, fillers, cosolvents, UV screening agents, stabilizers or preservatives distinct from the compounds of formula (I) as are defined according to the invention, and their mixtures.
  • emollients or softeners in particular sweet almond oil or apricot kernel oil
  • moisturizing agents in particular glycerol
  • soothing agents in particular a-bisabolol, allantoin and Aloe vera
  • vitamins and their derivatives essential fatty acids, propellants, peptizing agents, fillers, cosolvents, UV screening agents, stabilizers
  • these adjuvants can be present in an amount ranging from 0.001% to 10% by weight and better still from 0.01% to 5% by weight, with respect to the total weight of the composition.
  • a composition according to the invention can be obtained by any method known to a person skilled in the art for the formulation of coloured fragranced compositions.
  • a fragranced composition according to the invention can be obtained by simple mixing, at ambient temperature, namely at a temperature ranging from 20°C to 25°C, of the compounds constituting the composition.
  • a fragranced composition according to the invention results from the mixing between a colouring solution, on the one hand, and a fragranced solution comprising the compound of formula (I), on the other hand.
  • Said colouring solution thus comprises at least one colorant, in particular as defined above, in a physiologically acceptable medium, in particular an aqueous or aqueous/alcoholic medium.
  • Said fragranced solution comprises, for its part, at least one fragrancing substance, in particular as defined above, at least one compound of formula (I) as defined above, and ethanol in a content sufficient for the final composition to comprise strictly more than 15% by weight of ethanol, with respect to its total weight, in a physiologically acceptable medium.
  • Said fragranced solution can itself result from mixing between an intermediate fragranced solution, comprising at least one fragrancing substance, in particular as defined above, in a physiologically acceptable medium, in particular in an aqueous or aqueous/alcoholic medium, and a compound of formula (I) as defined above, directly or which is in solution in a physiologically acceptable medium, in particular in an aqueous or aqueous/alcoholic medium.
  • the compound(s) of formula (I) can be introduced, directly or in solution, into a fragranced composition, additionally comprising at least one fragrancing substance, at least one colorant, and ethanol in a content sufficient for the final composition to comprise strictly more than 15% by weight of ethanol, with respect to its total weight, in a physiologically acceptable medium.
  • the invention applies not only to fragrancing products but also to cosmetic treatment or care products for keratin materials, in particular the skin, including the scalp, and the lips, containing an odorous substance.
  • a composition according to the invention can thus constitute a cosmetic treatment, care or fragrancing composition for keratin materials, and in particular be provided in the form of an eau fraiche, an eau de toilette, an eau de perfume, an aftershave lotion, an eau de soin or a silicone or hydrosilicone care oil. It can also be provided in the form of a fragranced two- phase lotion (eau de toilette phase/hydrocarbon oil and/or silicone oil phase), a body milk or a shampoo.
  • compositions according to the invention can be packaged in the form of bottles.
  • a fragrancing composition according to the invention can be diffused according to various systems, such as sprays, aerosols or piezoelectric devices.
  • the devices in accordance with the invention are well known to a person skilled in the art and comprise pump-action sprays, aerosol containers comprising a propellant and also aerosol pumps using compressed air as propellant. The latter are in particular described in Patents US 4 077 441 and US 4 850 517.
  • compositions packaged as aerosols in accordance with the invention generally contain conventional propellants, such as, for example, dimethyl ether, isobutane, n-butane or propane.
  • propellants such as, for example, dimethyl ether, isobutane, n-butane or propane.
  • the compositions according to the invention are lotions and preferably have a viscosity ranging from 10 to 120 DU, more preferentially from 30 to 120 DU and more preferentially still from 40 to 80 DU; the viscosity being measured using a Rheomat TVe-05 device, at 25 °C, rotational speed 200 revolutions/min, spindle 1, 10 minutes.
  • compositions of the invention by means of mechanical or propellant gas pressurization devices so as to be applied in the form of fine particles (vaporization).
  • a fragranced composition according to the invention can also be in the form of a body milk or also in the form of a shampoo.
  • compositions The stability of the compositions is evaluated by observation of the change in the colour over time, visually and using a Konica Minolta CM 3600A spectrocolorimeter (L*, a*, b*).
  • compositions are poured into 50 ml bottles pots made of borosilicate glass and are then observed after storage for 2 months, at atmospheric pressure and under various conditions: a) in the refrigerator, at a temperature of 4 °C; b) at ambient temperature, namely of between 20°C and 25 °C, with the exclusion of light; c) in an oven, at a temperature of 37°C; d) in an oven, at a temperature of 45°C; or e) in natural light and at ambient temperature, namely of between 20°C and 25°C, and then, in addition: e.l) 16 hours in a SunTest CPS+ ageing device of the Atlas trade name, equipped with a xenon lamp, an irradiating light source, the spectral distribution of which is close to that of sunlight, delivering an energy of 765 W/m 2 , simulating exposure to neon lights in a shop; or e.2) 2 weeks in an oven at a temperature of 55°C, simulating an
  • the intensity difference DL between a reference composition and a composition tested after storage under the conditions mentioned above can be calculated from the L*a*b values according to the following formula:
  • Li* is the intensity of the colour of the reference composition
  • L2* is the intensity of the colour of the composition tested after storage.
  • the colouring solutions Cl to C13 are prepared using the proportions by weight as described in detail in Tables 1 and 2 below. The values are expressed as percentages by weight, with respect to the total weight of the colouring solution.
  • the colouring compositions are prepared by dissolving the dyes in the appropriate solvent or mixture of solvents.
  • the required amount of dye is weighed out in a beaker.
  • the amount of solvents ethanol, water and/or propylene glycol
  • the mixture is left stirring by magnetic stirring for 20 minutes.
  • Fragranced compositions Pl, P2, P3, P4 and P5 according to the invention and a fragranced composition P6 outside the invention are prepared using the proportions by weight as described in detail in Table 3 below.
  • the values are expressed as percentages by weight, with respect to the total weight of the fragranced composition.
  • composition Pl 0.1 g of extract containing at least 85% of rutin (Sophora Japonica Bud Extract) is added and then the mixture is left under magnetic stirring for 10 minutes, in order to obtain a fragranced solution. 0.05 g of the colouring solution is subsequently added using a pipette.
  • rutin Sophora Japonica Bud Extract
  • compositions P2 to P5 are prepared according to the same protocol, the extract containing rutin being replaced by a-glycosylrutin, luteolin, myricetin or quercetin respectively.
  • the composition P6, outside the invention is prepared according to the same protocol, except for the addition of compound corresponding to the formula (I).
  • Stability tests The stability of the coloured fragranced compositions is evaluated visually according to the protocol described in detail above.
  • composition P6 not comprising compound corresponding to the formula (I) as defined according to the invention, becomes colourless after ageing.
  • the composition according to the invention preserves its colouration for a significantly longer time. Furthermore, no significant change in odour was noticed over time.
  • the compound of formula (I) employed in the composition according to the invention is of natural origin.
  • the fragranced composition according to the invention is more stable over time than a composition not in accordance with the invention.

Abstract

The present invention relates to a fragranced composition comprising: a) at least one compound corresponding to the formula (I), or one of its geometrical isomers, in particular optical isomers, of its tautomers, and also its organic or inorganic acid or base salts, or its solvates, in particular hydrates, b) ethanol in a content strictly greater than 15% by weight, with respect to the total weight of the composition, c) at least one water-soluble colorant, and d) at least one fragrancing substance. It also relates to the use of a compound of formula (I) as stabilizer in a fragranced composition and to a method for the cosmetic treatment of keratin materials or of clothing.

Description

Description
Title: Fragranced cosmetic composition comprising at least one flavonoid compound, ethanol, a water-soluble colorant and a fragrancing substance
Technical field
The present invention is targeted at providing a novel fragranced cosmetic composition, for the field of fragrancing keratin materials and/or clothing, but also for the cosmetic treatment or care of keratin materials.
In general, the formulation of environmentally friendly cosmetic products is becoming a major challenge for meeting new consumer expectations, in particular those regarding natural and/or eco-friendly products, that is to say products, the design and development of which take into account their environmental impacts.
It is thus common practice to seek to replace synthetic compounds present in cosmetic compositions with natural ingredients and/or ingredients of natural origin.
These environmental problems concern all cosmetic products, in particular fragranced compositions.
A fragrance is the result of a combination of different odorous substances which each provide a specific diffusing odour or also “note” and which respectively evaporate at different periods. More specifically, each fragrance has what is known as a “top note”, which is the odour which diffuses first when the fragrance is applied or when the receptacle containing it is opened, a “middle or heart note”, which corresponds to the full fragrance (given off for a few hours after the “top note”) and a “base note”, which is the most persistent odour (given off for several hours after the “middle note”). The persistence of the base note corresponds to the holding of the fragrance.
Human beings have always sought to fragrance themselves and to fragrance the objects surrounding them or their environments, both to mask strong and/or unpleasant odours and to give a nice odour.
It is common practice to incorporate the fragrance in a certain number of products or compositions, in particular cosmetic and dermatological products or compositions, such as eaux fraiches, eaux de toilette, eaux de parfum, fragrance elixirs or extracts, aftershave lotions, eaux de soin or also two-phase lotions. In the preparation of fragrancing compositions, such as fragrances or eaux de toilette, the use of ethanol as solvent is very widespread. Ethanol makes it possible to fully dissolve the fragrancing ingredients resorted to by the perfumer. It is a very good solvent which evaporates quickly, thus giving a feeling of freshness. Ethanol additionally exhibits the advantage of being inexpensive and of making possible the formulation of transparent compositions.
For such reasons, the majority of fragrancing compositions contain ethanol, generally present in high contents, typically in contents of greater than 15% by weight of the total weight of these compositions.
For reasons of aesthetics and manufacturing cost, fragrances are coloured by adding an effective amount of colorant to the support of the formulation (which is generally alcoholic or aqueous/alcoholic) rather than tinting or lacquering the bottle, which is a more expensive industrial operation.
Mention may more particularly be made, as colorants, of water-soluble dyes, in particular which are natural or of natural origin, which, in a form diluted in aqueous media, provide the chromatic colouration which is most intense and therefore particularly advantageous for the field of cosmetics.
Unfortunately, the use of dyes in the aqueous solute state presents difficulties, in particular in terms of colour stability, concerning the fragranced compositions dedicated to incorporating them, in particular when the ethanol content is high, namely greater than 15% by weight.
With this, there should also be mentioned degradations conventional for water-soluble dyes, in particular due to oxidation by atmospheric oxygen, or thermal or photochemical reactions, in particular during prolonged storage, which can further detrimentally affect the colouring of the composition.
Thus, there is great advantage in managing to stabilize the colour developed in fragranced cosmetic formulations and in particular in an alcoholic or aqueous/alcoholic medium, starting from water-soluble dyes, in particular which are natural or of natural origin, this being the case not only over time but also when exposed to light and/or to heat and/or to atmospheric oxygen. In addition, it is necessary to prevent the scent of the fragrancing products from changing over time, whether or not in the presence of heat and/or of light. Prior art
In order to ensure the stability of fragranced formulations, it has already been proposed to incorporate therein a screening system and/or an antioxidant system.
Thus, a certain number of documents in the field of cosmetics, in particular EP 1 897 592 and WO 2005/042828, provide fragranced compositions, including in particular dyes, comprising combinations of UV screening agents as stabilizer, in particular of alkyl P,P’- diphenylacrylate or alkyl a-cyano-P,P’ -diphenylacrylate type, such as octocrylene, dibenzoylmethane derivatives, cinnamates or also camphor derivatives and triazines.
However, certain screening agents, such as alkyl P,P’ -diphenylacrylate or alkyl a-cyano- P,P’ -diphenylacrylate compounds, such as octocrylene, are not always satisfactory for stabilizing the tints while preserving the odour of the fragrances.
This is because certain screening agents can leave an unpleasant odour in the formula. Synthetic screening agents, such as ethylhexyl methoxycinnamate, are also unsatisfactory for stabilizing fragrancing solution colorants. In particular, they prove to be less efficient in terms of preserving the intensity of the colour and/or the chromaticity of the coloured solution with respect to light and/or over time.
Moreover, the piperidinol derivatives used in some of these compositions exhibit the disadvantage of generating yellowing in eaux de toilette and also a spurious odour with a “chemical” connotation.
Also, certain specific benzotriazole and/or triazine compounds have already been described for stabilizing cosmetic compositions, such as eaux de toilette. Combinations of these benzotriazole compounds with other specific sunscreens have also been defined for purposes of stabilization of fragrances. However, these benzotriazole compounds, in particular Bumetrizole, are difficult to dissolve in eaux de toilette and have a tendency to recrystallize over time, in addition to having low stabilizing power.
Besides the potential problems mentioned above associated with their presence, generally speaking, the sunscreens provided to date, such as ethylhexyl methoxy cinnamate, are synthetic.
However, as mentioned above, more and more users are looking for coloured fragranced compositions which are "less chemical” and more environmentally friendly. These users may perceive synthetic compounds negatively, in particular as compounds which are harmful to their health and to the environment. Thus, coloured fragranced compositions comprising synthetic sunscreens are not entirely satisfactory for consumers favouring natural compounds or compounds of natural origin over synthetic compounds.
What is more, these coloured fragranced compositions generally do not respect the principles of green chemistry.
There is thus great advantage in finding a means for stabilizing the colour of fragrancing compositions comprising a high content of ethanol, if possible with natural products or products of natural origin.
Moreover, it has already been sought to specifically stabilize water-soluble natural dyes or dyes of natural origin in cosmetic or food compositions.
On this account, the document WO 2017/162599 describes the stabilization of water-soluble natural dyes or dyes of natural origin using specific polymeric surfactants or fillers. Also, the document WO 2009/031051 provides for the stabilization of anthocyanin extracts with a stabilizing compound comprising a thiol group, in the field of food compositions.
Nevertheless, these documents do not in any way relate to the formulation of fragrancing compositions, even less comprising a high ethanol content.
Disclosure of the invention
A need thus remains to seek novel coloured fragranced formulations, in particular aqueous or aqueous/alcoholic formulations, which remain stable over time and under the effects of light.
In particular, a need remains to have available coloured fragranced cosmetic compositions, the change in the organoleptic properties, namely the odour and/or the colour, in particular at least the colour, of which is controlled over time, and this being achieved, if possible, by means of compounds which observe at least one of the twelve principles of green chemistry. In addition, there exists a need for such compositions, the formulation of which observes at least one of the twelve principles of green chemistry, in particular comprising ingredients resulting from green chemistry.
Finally, there remains a need to provide coloured fragranced cosmetic compositions which leave few, indeed even no, traces, in particular on clothing, during their use.
The present invention is specifically targeted at meeting these needs.
Summary of the invention Thus, according to a first of its aspects, the present invention relates to a fragranced composition, in particular cosmetic composition, comprising: a) at least one compound corresponding to the formula (I), or one of its geometrical isomers, in particular optical isomers, of its tautomers, and also its organic or inorganic acid or base salts, or of its solvates, in particular hydrates: [Chem 1]
Figure imgf000006_0001
in which formula (I): represents a double bond or a single bond, ^ R1 represents an atom or a group chosen from: - a hydrogen atom, - a hydroxyl, - a (C1-C6)alkyl group, - a (C1-C6)alkoxy group, - a monoglycoside or diglycoside sugar group, such as a glycosyl group, or an -O- monoglycoside or -diglycoside sugar group, such as an -O-glycosyl group; ^ R2 represents a hydrogen atom, a (C1-C6)alkyl group or a monoglycoside or diglycoside sugar group, such as a glycosyl group, ^ R3 represents a hydrogen atom or a (C1-C6)alkyl group, ^ n represents an integer of between 1 and 3 and m represents an integer of between 0 and 3, it being understood that: when m represents an integer greater than or equal to 2, the R2 radicals can be identical or different, and when n represents an integer greater than or equal to 2, the R3 radicals can be identical or different, b) ethanol in a content strictly greater than 15% by weight, with respect to the total weight of the composition, c) at least one water-soluble colorant, and d) at least one fragrancing substance.
The inventors have found, surprisingly, that the combination of a compound of formula (I) as defined above, within a fragranced composition comprising a high ethanol content, with at least one fragrancing substance and at least one water-soluble colorant, makes possible efficient stabilization of said composition, in particular of its colour.
Specifically, as emerges from the examples appearing below, the composition according to the invention is stable, in the sense that the change in the colour of the composition remains low over time, even under conditions simulating an accelerated ageing of the composition, in particular in an aqueous/alcoholic medium having a high ethanol content, and to light. Thus, the invention also relates, according to another of its aspects, to the use of a compound of formula (I) as stabilizer in a fragranced composition, in particular a cosmetic composition, additionally comprising ethanol in a content strictly greater than 15% by weight, with respect to the total weight of the composition, and also at least one water-soluble colorant and at least one fragrancing substance.
Certain compounds corresponding to the formula (I) have already been proposed in order to stabilize the colour in food compositions, in particular in Application US 2004/091589 Al or also in the documents Cortez et al., Comprehensive Reviews in Food Science and Food Safety, 16(1), 2016, pp. 180-198, and Hocine et al., RUDN Journal or Agronomy and Animal Industries, 13(4), 2018, pp. 257-286.
Nevertheless, these documents do not in any way relate to fragranced compositions, even less containing more than 15% by weight of ethanol, whereas such specific compositions are precisely the cause of an increased destabilization of the water-soluble dyes which are incorporated therein.
A composition according to the invention is intended in particular for the cosmetic treatment of keratin materials.
Thus, the invention relates, according to another of its aspects, to a method for the cosmetic treatment of keratin materials, in particular of the skin, comprising at least one stage of application, to said keratin materials, of a composition according to the invention.
The invention also relates to a method for the cosmetic treatment of keratin materials, in particular of the skin, or of clothing, comprising at least one stage of application, to said keratin materials and/or said clothing, of a fragranced composition according to the invention.
It is understood that the cosmetic treatment methods targeted in the present patent application are non-therapeutic.
A composition according to the invention is intended in particular to be employed in order to fragrance keratin materials and/or clothes.
Thus, the invention also relates, according to another of its aspects, to a method for the fragrancing of keratin materials, and in particular of the skin, and/or of clothing, comprising the application, to said keratin materials and/or said clothing, of the composition as defined above.
Advantageously, the content of water-soluble colorant(s) in the fragranced coloured composition can be less than or equal to 300 ppm.
This is because the inventors have found that, by virtue of the claimed combination, even a low content of water-soluble colorant(s) makes it possible to achieve a satisfactory chromatic intensity, while reducing the risks of formation of stains on the clothes during its application, in comparison with compositions comprising higher contents of colorant(s).
In the context of the present invention, and unless otherwise indicated, the definitions below apply:
Within the meaning of the present invention, the term “fragranced composition" or “fragrancing composition" is understood to denote any composition which leaves a fragrance after application on keratin materials.
Within the meaning of the present invention, the term “keratin materials" is understood in particular to denote the skin, the lips, the hair, the scalp, the eyelashes and the eyebrows or also the nails, in particular the skin and/or the lips, and preferably the skin.
The term “colorant" is understood to denote any compound capable of colouring the fragranced composition, that is to say any compound which absorbs in the visible spectrum, in particular so as to appear to the human eye to have a colour such as yellow, orange, red, purple, blue or green, in particular orange, red, purple or blue.
In other words, a fragranced composition according to the invention is said to be “coloured" . The term “coloured composition” is understood to mean a composition which appears to the human eye to have a colour in the visible spectrum, that is to say which to the eye is distinct from white or colourless, namely a composition which absorbs in the yellow, orange, red, crimson, purple, blue and green ranges. Such a composition can be opaque or clear, preferably clear.
Within the meaning of the present invention, the term “ clear ' is understood to mean that the composition is transparent, that is to say that it allows light to pass through and allows objects which are located behind to appear in sharp definition.
Within the meaning of the present invention, the term “water-soluble” is understood to mean that the natural or synthetic, generally organic, colorant is soluble in an aqueous phase or water-miscible solvents.
A fragranced coloured composition can be in any form suitable for its application to keratin materials and/or clothing. It can in particular be in liquid or solid form, for example in powder form.
The term “powder” is understood to mean a composition in pulverulent form, which is preferably essentially devoid of dust. In other words, the particle size distribution of the particles is such that the content by weight of the particles which have a size of less than or equal to 50 micrometres (dust content), preferably of less than or equal to 10 micrometres (dust content), is advantageously less than or equal to 5%, preferably less than 2% and more particularly less than 1% (size of the particles evaluated using a Retsch AS 200 Digit particle size analyser; oscillation height: 1.25 mm/sieving time: 5 minutes). Advantageously, the size of the particles is between 10 pm and 500 pm. The “powder” of solid material(s) can be sieved in order to obtain particles with upper limit sizes corresponding to the orifices or sizes of the meshes of the sieve of particularly between 35 and 80 mesh (US). According to a specific mode of the invention, the size of the particles of the powder of solid natural material(s) is fine. According to the invention, this more particularly means a size of particles of less than or equal to 900 pm. Preferentially, the powder is constituted of fine particles with a size of between 7 pm and 700 pm and better still between 100 nm and 500 pm.
Within the meaning of the present invention, the term “fragrancing substance” is understood to denote any fragrance, odorous starting material or aroma which is capable of giving off a pleasant odour, in particular as defined in the continuation of the text. Within the meaning of the present invention, “fragrancing” , “odorous” or “odoriferous” substances are synonymous. A composition according to the invention is generally suitable for application to keratin materials, in particular topical application to the skin, and thus generally comprises a physiologically acceptable medium, that is to say a medium compatible with the skin. It is preferably a cosmetically acceptable medium, that is to say a medium which exhibits a pleasant colour, odour and feel and which does not cause any unacceptable discomfort, that is to say stinging, tautness or redness, liable to dissuade the user from applying this composition. Within the meaning of the present invention, a “stabilizer” is understood to denote a compound which is capable of stabilizing the fragranced composition comprising it, in particular in terms of preservation of its organoleptic properties with respect to external attacking factors, in particular light or temperature differences, in particular the colour and/or the odour of said composition, and more particularly still the colour of said composition. A (Cx-Cz)alkyl group represents a linear or branched hydrocarbon chain comprising from x to z carbon atoms. For example, a (C1-C6)alkyl group represents a linear or branched hydrocarbon chain comprising from 1 to 6 carbon atoms. A (Cx-Cz)alkoxy group represents an -O-(Cx-Cz)alkyl radical in which the (Cx-Cz)alkyl group is as defined above. A “sugar” radical is understood to denote a monosaccharide, oligosaccharide or polysaccharide radical, in particular constituted of from 1 to 5 saccharide units, more particularly from 2 to 3 and preferably of 2 saccharide units, bonded via a covalent bond to the compound carrying the group. Mention may be made, as sugar radical, of sucrose, glucose, galactose, ribose, fucose, maltose, fructose, mannose, arabinose, xylose or lactose. The term “glycosyl” group is understood to denote a monovalent radical obtained from a mono- or oligosaccharide by replacement of one of the hemiacetal hydroxyl groups of said mono- or oligosaccharide by a covalent bond with the compound carrying the group. Preferentially, the compound of formula (I) is chosen from natural compounds or compounds of natural origin. Within the meaning of the present invention, the term “natural” is understood to mean that the colorant is obtained directly from the earth or the soil, or from plants or animals, via, if appropriate, one or more physical processes, such as, for example, milling, refining, distillation, purification or filtration, or else results from a biotechnological process, in particular results from microbiological or cell cultures, for example of fungi or of bacteria. “Natural” dyes or pigments include compounds which are present in nature and which can be reproduced by chemical (semi)synthesis.
Within the meaning of the present invention, the term “of natural origin” is understood to mean that the colorant is obtained from a natural substance which has undergone one or more additional chemical or industrial treatments bringing about modifications which do not affect the essential qualities of this substance. Mention may be made, as non-limiting example of additional chemical or industrial treatment bringing about modifications which do not affect the essential qualities of a natural compound, of those authorized by the controlling bodies, such as Ecocert (Reference system for biological and ecological cosmetic products, January 2003), or defined in recognized handbooks in the field, such as “Cosmetics and Toiletries Magazine”, 2005, Vol. 120, 9 (10).
According to the invention, a compound is considered to be natural or of natural origin when it is predominantly composed of natural constituents, that is to say when the ratio by weight of natural constituents to non-natural constituents which make up the compound is greater than 1.
More advantageously, the compound of formula (I) is a “green” compound, namely that it observes at least one of the twelve principles of green chemistry.
Within the meaning of the present invention, the term “geometrical isomer” is understood to denote any molecule of identical constitution to the formula (I) defined above but the spatial organization of the atoms of which is different. In particular, they can be conformational stereoisomers, that is to say compounds which differ by rotation around a single bond, or configurational stereoisomers, in particular enantiomers or diastereoisomers (or optical isomers), or also constitutional isomers, that is to say compounds which differ in the sequence of the atoms, in particular tautomers in the case of tautomeric equilibrium.
Within the meaning of the present invention, the term “organic or inorganic acid or base salt” is understood to denote a salt obtained between an ionic form of a compound of formula (I) and a corresponding counterion. In particular, such a salt is obtained by addition of an organic or inorganic acid or base, which is in particular cosmetically acceptable, to the compound of formula (I). Mention may be made, as examples of inorganic bases, of hydroxides or carbonates of alkali or alkaline earth metals, such as sodium, potassium, calcium, ammonium, magnesium, lithium or sodium. Mention may be made, as examples of organic bases, of amines or alkanolamines. Mention may be made, as examples of acids, of hydrochloric acid, hydrobromic acid, sulfuric acid, alkylsulfonic acids, arylsulfonic acids, citric acid, succinic acid, tartaric acid, lactic acid, alkoxysulfinic acids, aryloxysulfinic acids, phosphoric acid or acetic acid.
Within the meaning of the present invention, the term “solvate” is understood to denote the form of the compound of formula (I) when it is associated with a solvent. The solvates include conventional solvates formed during the process of preparation of the compound of formula (I). Examples of solvates are those obtained in the presence of water or of a linear or branched alcohol, in particular ethanol or isopropanol.
Within the meaning of the present invention, the term “flavone” is understood to denote any compound comprising a 2-phenylchromen-4-one (2-phenyl-l-benzopyran-4-one) structural backbone corresponding to the following formula:
[Chem 2]
Figure imgf000012_0001
Within the meaning of the present invention, the term “flavonol” is understood to denote any compound comprising a flavone backbone as defined above and substituted by a hydroxyl group in the 3 position, namely a backbone corresponding to the following formula: [Chem 3]
Figure imgf000012_0002
Within the meaning of the present invention, the term “flavanone” is understood to denote any compound comprising a flavone backbone as defined above but not comprising an unsaturation in the 2,3 position, namely a backbone corresponding to the following formula: [Chem 4]
Figure imgf000013_0001
The expression “at least one" is equivalent to “one or more".
The expression ''inclusive'' for a range of concentrations means that the limits of the range form part of the defined interval.
The expressions “of between ... and “comprises from ... to “formed from ... to ...” and “ranging from ... to ...” should be understood as being inclusive of the limits, unless otherwise specified.
Other characteristics, alternative forms and advantages of the compositions according to the invention will emerge more clearly on reading the description and the examples which will follow.
Detailed description
Compounds of formula (I)
As mentioned above, a fragranced composition according to the invention comprises at least one compound of formula (I), or one of its geometrical isomers, in particular optical isomers, of its tautomers, and also its organic or inorganic acid or base salts, or its solvates, in particular hydrates:
[Chem 5]
Figure imgf000013_0002
in which formula (I): represents a double bond or a single bond, ^ R1 represents an atom or a group chosen from: - a hydrogen atom, - a hydroxyl, - a (C1-C6)alkyl group, - a (C1-C6)alkoxy group, - a monoglycoside or diglycoside sugar group, such as a glycosyl group, or an -O- monoglycoside or -diglycoside sugar group, such as an -O-glycosyl group; ^ R2 represents a hydrogen atom, a (C1-C6)alkyl group or a monoglycoside or diglycoside sugar group, such as a glycosyl group, ^ R3 represents a hydrogen atom or a (C1-C6)alkyl group, ^ n represents an integer of between 1 and 3 and m represents an integer of between 0 and 3, it being understood that: when m represents an integer greater than or equal to 2, the R2 radicals can be identical or different, and when n represents an integer greater than or equal to 2, the R3 radicals can be identical or different. In the formula (I) defined above, it is furthermore understood that the -OR2 group(s) is (are) carried by any one of the carbon atoms in the 5 to 8 positions of the flavone, flavonol or flavanone backbone and that the -OR3 group(s) is (are) carried by any one of the carbon atoms in the 2' to 6' positions of the flavone, flavonol or flavanone backbone. Preferably, the -OR2 group(s) is (are) carried by either one of the carbon atoms in the 5 and/or 7 positions. Advantageously, in the formula (I), m has the value 2 and the two -OR2 groups are carried respectively by the carbon atoms in the 5 and 7 positions. According to one embodiment, the -OR3 group(s) is (are) carried by any one of the carbon atoms in the 3', 4' and/or 5' positions. Advantageously, in the formula (I), n has the value 2 and the two -OR3 groups are carried respectively by the carbon atoms in the 3' and 4' positions, or n has the value 3 and the three -OR3 groups are carried respectively by the carbon atoms in the 3', 4' and 5' positions. Advantageously, in the formula (I), R1 represents an atom or a group chosen from: i) hydrogen, ii) a hydroxyl and iii) a glycosyl or -O-glycosyl group. Advantageously, in the formula (I), each R2 independently represents a hydrogen atom or a glycosyl group, preferably a hydrogen atom. Advantageously, in the formula (I), each R3 independently represents a hydrogen atom or a methyl, preferably a hydrogen atom. Advantageously, in the formula (I), n and m, which are identical or different, independently represent an integer ranging from 1 to 3. The compounds corresponding to the formula (I) belong generically to the family of the flavonoids, more specifically to the families of the flavones, flavonols and flavanones. Preferably, a composition according to the invention comprises a compound of formula (I) chosen from luteolin, quercetin, myricetin, rutin, hesperidin, narirutin, α-glycosylrutin, quercitrin, isoquercitrin, morin, hesperetin, chrysin, apigenin, luteolin-7-O-glucoside, 6- hydroxyflavone, 7,8-dihydroxyflavone or tropoflavin, and their mixtures. According to a particularly preferred embodiment, the compound of formula (I) is of formula (I') below, or one of its geometrical isomers, of its tautomers, and also its organic or inorganic acid or base salts, or its solvates, in particular hydrates: [Chem 6]
Figure imgf000015_0001
in which formula (I'): R represents an atom or a group chosen from: i) a hydrogen atom, ii) a hydroxyl, iii) a monoglycoside or diglycoside sugar group, such as a glycosyl group, or an -O- monoglycoside or -diglycoside sugar group, such as an -O-glycosyl group, preferably a glycosyl group or an -O-glycosyl group, iv) a (C1-C6)alkyl group, and v) a (C1-C6)alkoxy group, n and m representing, independently of each other, an integer of between 1 and 3, preferably equal to 1 or 2. Preferably, the -OH groups are carried by any one of the carbon atoms in the 5 and/or 7 and 3', 4' and/or 5' positions.
Advantageously, in the formula (I'), m has the value 2 and the two -OH groups are carried respectively by the carbon atoms in the 5 and 7 positions.
According to one embodiment, the -OH group(s) is (are) carried by any one of the carbon atoms in the 3', 4' and/or 5' positions.
Advantageously, in the formula (I'), n has the value 2 and the two -OH groups are carried respectively by the carbon atoms in the 3' and 4' positions, or n has the value 3 and the three -OH groups are carried respectively by the carbon atoms in the 3', 4' and 5' positions.
The compounds of formulae (I) and (I') in accordance with the invention are preferably chosen from natural compounds or compounds of natural origin.
They are preferably “green” compounds.
Preferably, the composition according to the invention comprises a compound of formula (I) or (I1) chosen from luteolin, quercetin, myricetin, rutin, a-glycosylrutin and their mixtures, more preferentially still chosen from rutin, a-glycosylrutin and their mixtures.
According to one embodiment, the compound of formula (I) is rutin.
According to another embodiment, the compound of formula (I) is a-glycosylrutin.
The compounds of formula (I) or (I') can be found in numerous plant extracts, in particular grapes, berries, nuts, the peel of citrus fruits, capers, olives, buckwheat, asparagus, raspberry, blackcurrant, plum, mango, green beans, rhubarb, bilberry, onion, quince, apple, cherry, broccoli, green or black tea leaves, and also plants, such as plants of the genus Citrus, Sophora japonica, Eucalyptus macrorhyncha, wild pansy, white mulberry, parsley, Ginkgo biloba, lovage, elder or Vitis vinifera.
The compounds of formulae (I) and (I') can be obtained by any method known to a person skilled in the art, for example by extraction from a plant extract.
The compounds of formula (I) or (I') defined above can optionally be introduced into a fragranced composition according to the invention in the form of a plant extract. For example, rutin can be employed in the form of an extract of buds of the plant Sophora japonica.
A certain number of compounds of formula (I) or (I') are also available commercially, such as, for example, a-glycosylrutin sold by Qingdao Taitong Pharmaceutical. A fragranced composition according to the invention can comprise from 0.01% to 5.0% by weight of compound(s) of formula (I), in particular from 0.03% to 2.0% by weight, preferably from 0.05% to 1.0% by weight, more preferentially from 0.05% to 0.2% by weight, with respect to the total weight of said composition.
Advantageously, the content of compound(s) of formula (I) is less than or equal to 0.1% by weight, with respect to the total weight of the composition. Thus, a fragranced composition according to the invention can comprise from 0.01% to 0.1% by weight of compound(s) of formula (I), in particular from 0.03% to 0.1% by weight, preferably from 0.05% to 0.1% by weight, with respect to the total weight of said composition.
As mentioned above, the compound of formula (I) can be employed in the form of a plant extract also known as “crude starting material”, comprising one or more compounds of formula (I) as defined above. Thus, a fragranced composition according to the invention can comprise from 0.05% to 10% by weight of plant extract containing at least one compound of formula (I), with respect to the total weight of said composition.
In particular, said plant extract(s) is (are) rich in compound(s) of formula (I), namely that they can comprise a content of compound(s) of formula (I) ranging from 80% to 99% by weight, in particular from 85% to 95% by weight, with respect to their total weight.
Ethanol
As mentioned above, a fragranced composition according to the invention comprises ethanol in a content strictly greater than 15% by weight, with respect to the total weight of the composition.
As already mentioned above, ethanol is commonly used in the field of fragranced compositions as solvent.
In particular, ethanol can be introduced into the composition in the form of absolute ethanol, namely comprising less than 1% by weight of water, in particular less than 0.5% by weight of water, for example comprising 0.2% by weight of water, with respect to its total weight. Alternatively, the ethanol can be 95° ethanol.
Advantageously, the ethanol is of natural origin, in particular of plant origin, namely that it is produced from biomass. Ethanol of natural origin is known as “bioethanol”.
Advantageously, a composition according to the invention can comprise a content of (bio)ethanol varying from 16% to 99.5% by weight, in particular from 25% to 97% by weight, more particularly from 35% to 95% by weight, more particularly still from 45% to 90% by weight, with respect to the total weight of the composition.
In particular, a composition according to the invention can comprise a content of (bio)ethanol ranging from 65% to 80% by weight, for example of 68%, of 70% or of 78% by weight, with respect to the total weight of the composition.
Water-soluble colorant
As mentioned above, a fragranced composition according to the invention comprises at least one water-soluble colorant, also called “ water -soluble dye” .
As mentioned above, a colorant is capable of colouring the fragranced composition by absorbing in the visible spectrum.
Mention may be made, as visual colour and absorption wavelength associated with said colour, of the following colours: “yellow” = Xmax greater than 400 nm up to 440 nm, limit included, “orange” = Xmax greater than 440 nm up to 490 nm, limit included, “red” = Xmax greater than 490 nm up to 520 nm, limit included, “crimson” = Amas greater than 520 nm up to 560 nm, limit included, “purple” = Xmax greater than 560 nm up to 580 nm, limit included, “blue” = Xmax greater than 580 nm up to 620 nm, limit included, “blue-green” = Xmas greater than 620 nm up to 650 nm, limit included, and “green” = Amas greater than 650 nm up to 780 nm, limit included.
Advantageously, the water-soluble colorant suitable for the invention is capable of colouring the fragranced composition by absorption of the following colours: “orange” = Xmax greater than 440 nm up to 490 nm, limit included, “red” = Xmax greater than 490 nm up to 520 nm, limit included, “crimson” = Xmas greater than 520 nm up to 560 nm, limit included, “purple” = dmas greater than 560 nm up to 580 nm, limit included, and “blue” = Xmax greater than 580 nm up to 620 nm, limit included.
Preferably, the water-soluble colorant is distinct from the compound of formula (I) as defined above.
In particular, a dye is water-soluble when its solubility in water, measured at 25°C, is at least equal to 0.01 gd.
Preferably, the water-soluble colorant is chosen from water-soluble colorants which are natural or of natural origin. According to a specific embodiment, the water-soluble dyes suitable for the invention result from extracts of animals, bacteria, fungi, algae or plants, used in their entirety or partially. The water-soluble dye(s) suitable for the invention preferentially result from extracts of plants or plant parts, such as fruits, including citrus fruits, vegetables, trees or shrubs. Mixtures of these extracts can also be used.
Thus, the water-soluble colorant can be introduced into a fragranced composition according to the invention in the form of a natural extract.
Such extracts can be obtained by extraction of various plant parts, such as, for example, the root, the wood, the bark, the leaf, the flower, the fruit, the pip, the pod or the peel.
Mention may be made, among the plant extracts, of extracts of leaves of roses, of gardenias, of Clitoria tematea or blue pea flowers, of turmeric rhizomes or else carrot, sweet potato or radish peelings.
Mention may be made, among the extracts of fruits, of extracts of apple, extracts of grape or extracts of cacao tree beans and/or pods.
Mention may be made, among the extracts of vegetables, of extracts of potato, of onion peel and of beetroot.
Mention may be made, among the extracts of tree wood, of extracts of pine bark or extracts of logwood.
Use may also be made of mixtures of plant extracts.
Mention may be made, as examples of water-soluble colorants more particularly suitable for the invention, of water-soluble dyes which are natural or of natural origin, in particular dyes derived from natural ortho -diphenol.
More particularly, the ortho-diphenols which can be used according to the invention are chosen from: flavanols, in particular catechin and epicatechin gallate, pyrans, in particular anthocyanidins, in particular cyanidin, delphinidin and petunidin, anthocyanins or anthocyans, in particular myrtillin or anthocyanosides; ortho-hydroxybenzoates, for example gallic acid salts, hydroxystilbenes, for example 3,3',4,5'-tetrahydroxystilbene, optionally oxylated
(for example glucosylated),
3,4-dihydroxyphenylalanine and its derivatives, 2,3-dihydroxyphenylalanine and its derivatives, 4,5-dihydroxyphenylalanine and its derivatives, dihydroxy cinnamate s , ortho-polyhydroxycoumarins, ortho-polyhydroxyisocoumarins, ortho-poly hydroxycoumarones; ortho-polyhydroxyisocoumarones, ortho-polyhydroxychalcones, ortho-poly hydroxychromones, quinones, hydroxy xanthone s ,
1,2-dihydroxybenzene and its derivatives,
1.2.4-trihydroxybenzene and its derivatives,
1,2,3-trihydroxybenzene and its derivatives,
2.4.5-trihydroxytoluene and its derivatives, proanthocyanidins and in particular proanthocyanidins Al, A2, Bl, B2, B3 and Cl, proanthocyanins, tannic acid, gallic acid, ellagic acid, neoflavanols and neoflavanones, in particular derivatives of haematoxylin, of haematin, of brazilin and of brazilein; and the mixtures of the preceding compounds.
Preferably, the ortho-diphenols which can be used according to the invention are chosen from anthocyanidins, in particular cyanidin, delphinidin and petunidin; anthocyanins or anthocyans, in particular myrtillin; proanthocyanidins and in particular the proanthocyanidins Al, A2, Bl, B2, B3 and Cl; proanthocyanins; and the mixtures of the preceding compounds.
Mention may be made, as examples of water-soluble colorants more particularly suitable for the invention, of those chosen from: pyran or pyranium dyes, in particular anthocyans and anthocyanosides, preferably extracts of red radish or extracts of sweet potato, in particular purple sweet potato; and - polyene dyes in particular chosen from jasminoids, especially those, the coloured active principles of which have the following formula: [Chem 7]
Figure imgf000021_0001
n which: R11 and R16, which are identical or different, represent: ) a cycloalkyl group which is optionally unsaturated and/or optionally substituted by one or more groups chosen from a) oxo, b) hydroxyl and c) (C1-C6)alkyl, preferably (C1- C4)alkyl, in particular methyl; i) a cycloalkylcarbonyl group, the cycloalkyl group of which is optionally unsaturated and/or optionally substituted by one or more groups a) to c) as defined above; ii) -C(O)-O-R17 with R17 representing a hydrogen atom or a (C1-C6)alkyl, preferably C1-C4)alkyl, group, in particular a methyl group; v) sugar, in particular glycosyl or glycosyloxy; or v) sugar-C(O)-, and R12 to R15, which are identical or different, preferably identical, represent a hydrogen atom or a (C1-C6)alkyl group; preferably, R12 to R15 represent a (C1-C4)alkyl group, for example a methyl group, and also its geometrical isomers, its salts of organic or inorganic bases and its solvates, such as its hydrates. Mention may also be made, as examples of water-soluble colorants suitable for the invention, of extracts of red, blue or yellow gardenia, carotenes, such as β-carotene, paprika and curcumin, the coloured active principles of which have the following formula, or one of its geometrical isomers, of its salts of organic or inorganic bases or of its solvates, in particular ts hydrates: Chem 8]
Figure imgf000022_0001
in which R7, R8, R9 and R10 represent, independently of one another, a hydrogen atom, a hydroxyl group or a (C1-C6)alkoxy, preferably (C1-C4)alkoxy, group, in particular a methoxy group, it being understood that at least one of the R7 to R10 groups represents a hydroxyl group. Preferably, R8 and R10 represent a hydroxyl group, R7 represents a hydrogen atom or a (C1- C4)alkoxy group, in particular a methoxy group, and R9 represents a hydrogen atom or a (C1- C4)alkoxy group, in particular a methoxy group. According to a preferred embodiment, the water-soluble colorant is chosen from: - pyran or pyranium dyes, in particular anthocyans and anthocyanosides, preferably extracts of red radish or extracts of sweet potato, in particular purple sweet potato; - polyene dyes in particular chosen from jasminoids, especially those, the coloured active principles of which have the following formula: [Chem 9]
Figure imgf000022_0002
in which: R11 and R16, which are identical or different, represent: i) a cycloalkyl group which is optionally unsaturated and/or optionally substituted by one or more groups chosen from a) oxo, b) hydroxyl and c) (C1-C6)alkyl, preferably (C1- C4)alkyl, in particular methyl; ii) a cycloalkylcarbonyl group, the cycloalkyl group of which is optionally unsaturated and/or optionally substituted by one or more groups a) to c) as defined above; iii) -C(O)-O-R17 with R17 representing a hydrogen atom or a (C1-C6)alkyl, preferably (C1-C4)alkyl, group, in particular a methyl group; iv) sugar, in particular glycosyl or glycosyloxy; or v) sugar-C(O)-; and R12 to R15, which are identical or different, preferably identical, represent a hydrogen atom or a (C1-C6)alkyl group; preferably, R12 to R15 represent a (C1-C4)alkyl group, for example a methyl group; and also its geometrical isomers, its salts of organic or inorganic bases and its solvates, such as its hydrates; and - curcumin, the coloured active principles of which have the following formula: [Chem 10]
Figure imgf000023_0001
in which R7, R8, R9 and R10 represent, independently of one another, a hydrogen atom, a hydroxyl group or a (C1-C6)alkoxy, preferably (C1-C4)alkoxy, group, in particular a methoxy group, it being understood that at least one of the R7 to R10 groups represents a hydroxyl group; preferably, R8 and R10 represent a hydroxyl group, R7 represents a hydrogen atom or a (C1-C4)alkoxy group, in particular a methoxy group, and R9 represents a hydrogen atom or a (C1-C4)alkoxy group, in particular a methoxy group, and also its geometrical isomers, its salts of organic or inorganic bases and its solvates, such as its hydrates. Mention may be made, as other examples of water-soluble colorants suitable for the invention, of phthalocyanins and porphyrins, in particular complexed with a metal, preferably a transition metal (such as titanium, manganese, iron, cobalt, nickel, copper or zinc, in particular magnesium or copper), such as chlorophyll, chlorophyllin and their metal complexes, in particular their transition metal complexes, especially of titanium, manganese, iron, cobalt, nickel, copper or zinc, in particular magnesium or copper, preferably copper. More preferentially, a water-soluble colorant suitable for the invention can be chosen from: i) paprika, in particular that sold under the name Capsanthin/Capsorubin by Vitiva; ii) β-carotene, in particular that sold under the name Beta-Carotene by Vitiva; iii) extract of red radish, in particular that sold under the name Raphanus sativus Root Extract by Vitiva, the colouring active principle of which is enocyanin; iv) extract of purple sweet potato, in particular that sold under the name Anthocyanins/Ipomoeia batatas Root Extract by Vitiva, which is an extract of the roots of Ipomoea batatas, Convolvulacaea; v) yellow gardenia, in particular that sold under the name Gardenia Yellow - Gardenia jasminoides Fruit Extract by Henan Zhongda Biological; vi) red gardenia, in particular that sold under the name Gardenia Fruit Extract For Water Soluble Red by Henan Zhongda Biological; vii) blue gardenia, in particular that sold under the name Gardenia Blue - Hydrolyzed Gardenia florida Extract With Maltodextrin by Henan Zhongda Biological; viii) curcumin, in particular that sold under the name Curcuma longa Extract TBC by Naturex; ix) extract of blue pea, in particular that sold under the name Clitoria ternatea Flower Extract by Naturalsolution. According to a preferred embodiment, the water-soluble colorant is chosen from pyran dyes, polyene dyes, red, blue or yellow gardenia extracts, carotenes, paprika, curcumin and their mixtures, in particular from paprika, β-carotene, red radish extract, purple sweet potato extract, yellow, red or blue gardenia, curcumin, blue pea extract and their mixtures. According to a specific embodiment of the invention, the colorant(s) of the invention is (are) chosen from organic pigments. Mention may be made, among the organic pigments of the invention, of carbon black, pigments of D & C type (in particular of azo, anthraquinone, nitro and triarylmethane form) and lakes based on cochineal carmine of barium, strontium, calcium and aluminium, preferably pigments of D & C type. According to a specific embodiment of the invention, the colorant(s) of the invention is (are) chosen from water-soluble anionic, cationic, zwitterionic or neutral dyes and more particularly anionic dyes (i.e., commonly referred to as "acid" direct dyes for their affinity with alkaline substances). The term “anionic dyes” is understood to mean any dye comprising, in its structure, at least one CO2R' or SO3R' substituent with R' denoting a hydrogen atom or a cation originating from a metal or from an amine, or an ammonium ion. The anionic dyes can be chosen from acid nitro direct dyes, acid azo dyes, acid azine dyes, acid triarylmethane dyes, acid indoamine dyes, acid anthraquinone dyes, indigoids and acid natural dyes. Mention may be made, as anionic dyes suitable for the invention, of the dyes chosen from those of following formulae (G), (G'), (J), (J'), (K), (K'), (L) and (M) and their mixtures, in particular of formulae (G), (J) and (L) and their mixtures: a) the anionic azo dyes of formulae (G) and (G') below: [Chem 11]
Figure imgf000025_0001
in which formulae R7, R8, R9, R10, R'7, R'8, R'9 and R'10, which are identical or different, represent a hydrogen or halogen atom or a group chosen from: - alkyl; - alkoxy, alkylthio; - hydroxyl, mercapto; - nitro, nitroso; - R°-C(X)-X'-, R°-X'-C(X)- or R°-X'-C(X)-X''- with R° representing a hydrogen atom or an alkyl or aryl group; X, X' and X'', which are identical or different, representing an oxygen or sulfur atom or NR, with R representing a hydrogen atom or an alkyl group; - M+(O-)S(O)2- with M+ representing a hydrogen atom or a cationic counterion; - M+(O-)CO- with M+ as defined above; - R''-S(O)2- with R'' representing a hydrogen atom or an alkyl, aryl, (di)(alkyl)amino or aryl(alkyl)amino group; preferentially a phenylamino or phenyl group; R"'-S(0)2-X'- with R'" representing an alkyl or aryl group which is optionally substituted, X' being as defined above;
(di) (alky 1) amino ; aryl(alkyl)amino optionally substituted by one or more groups chosen from i) nitro; ii) nitroso; iii) M+(0')S(0)2- and iv) alkoxy with M+ as defined above; optionally substituted heteroaryl; preferentially a benzothiazolyl group; cycloalkyl; in particular cyclohexyl;
Ar-N=N- with Ar representing an optionally substituted aryl group; preferentially a phenyl optionally substituted by one or more alkyl, M+(0')S(0)2- or phenylamino groups; or else two contiguous groups R7 with Rs or Rs with R9 or R9 with Rio together form a fused benzo group A'; and R'7 with R's or R's with R'9 or R'9 with R'10 together form a fused benzo group B'; with A' and B' optionally substituted by one or more groups chosen from nitro; nitroso; M+(0')S(0)2-; hydroxyl; mercapto; (di)(alkyl)amino; R°-C(X)-X'-; R°- X'-C(X)-; R°-X'-C(X)-X"-;
Ar-N=N- and ary l(alkyl) amino which is optionally substituted; with M+, R°, X, X', X" and Ar as defined above; and in which:
W represents a sigma c bond, an oxygen or sulfur atom, or a divalent -NR- radical with R as defined above or methylene -C(Ra)(Rb)- radical with Ra and Rb, which are identical or different, representing a hydrogen atom or an aryl group, or else Ra and Rb form, together with the carbon atom which carries them, a spiro cycloalkyl; preferentially, W represents a sulfur atom or Ra and Rb together form a cyclohexyl; it being understood that the formulae (G) and (G') comprise at least one sulfonate M+(O" )S(O)2- radical or one carboxylate M+(O')CO- radical on one of the rings A, A', B, B' or C; preferentially sodium sulfonate.
Mention may be made, as examples of dyes of formula (G), of: Acid Red 1, Acid Red 4, Acid Red 13, Acid Red 14, Acid Red 18, Acid Red 27, Acid Red 28, Acid Red 32, Acid Red 33, Acid Red 35, Acid Red 37, Acid Red 40, Acid Red 41, Acid Red 42, Acid Red 44, Pigment Red 57, Acid Red 68, Acid Red 73, Acid Red 135, Acid Red 138, Acid Red 184, Food Red 1, Food Red 13, Orange 4, Acid Orange 6, Acid Orange 7, Acid Orange 10, Acid Orange 19, Acid Orange 20, Acid Orange 24, Yellow 6, Acid Yellow 9, Acid Yellow 36, Acid Yellow 199, Food Yellow 3; Acid Violet 7, Acid Violet 14, Acid Blue 113, Acid Blue 117, Acid Black 1, Acid Brown 4, Acid Brown 20, Acid Black 26, Acid Black 52, Food Black 1, Food Black 2; Food Yellow 3 or Sunset Yellow; and mention may be made, as examples of dyes of formula (G'), of: Acid Red 111, Acid Red 134, Acid Yellow 38; b) the anthraquinone dyes of formulae (J) and (J') below: [Chem 13]
Figure imgf000027_0001
in which formulae (J) and (J') R22, R23, R24, R25, R26 and R27, which are identical or different, represent a hydrogen or halogen atom or a group chosen from: alkyl; hydroxyl, mercapto; alkoxy, alkylthio; optionally substituted aryloxy or arylthio, preferentially substituted by one or more groups chosen from alkyl and M+(O')S(O)2- with M+ as defined above; aryl(alkyl)amino optionally substituted by one or more groups chosen from alkyl and M+(O')S(O)2- with M+ as defined above;
(di) (alky 1) amino ;
(di) (hydroxy alky 1) amino ; Z1
M+(0')S(0)2- with M+ as defined above; and in which:
Z' represents a hydrogen atom or an NR28R29 group with R28 and R29, which are identical or different, representing a hydrogen atom or a group chosen from: alkyl; polyhydroxyalkyl, such as hydroxyethyl; aryl optionally substituted by one or more groups, particularly i) alkyl, such as methyl, n-dodecyl or n-butyl; ii) M+(0')S(0)2- with M+ as defined above; iii) R°-C(X)-X'-, R°-X'-C(X)-, R°-X'-C(X)-X"- with R°, X, X' and X" as defined above; preferentially, R° represents an alkyl group; cycloalkyl; in particular cyclohexyl;
Z represents a group chosen from hydroxyl and NR'28R'29 with R'28 and R'29, which are identical or different, representing the same atoms or groups as R28 and R29 as defined above; it being understood that the formulae (J) and (J') comprise at least one sulfonate M+(O" )S(O)2- radical or one carboxylate M+(O')CO- radical; preferentially sodium sulfonate.
Mention may be made, as examples of dyes of formula (J), of: Acid Blue 25, Acid Blue 43, Acid Blue 62, Acid Blue 78, Acid Blue 129, Acid Blue 138, Acid Blue 140, Acid Blue 251, Acid Green 25, Acid Green 41, Acid Violet 42, Acid Violet 43, Mordant Red 3; EXT Violet No. 2; and mention may be made, as an example of a dye of formula (J'), of: Acid Black 48; d) the nitro dyes of formulae (K) and (K') below:
[Chem 15]
Figure imgf000028_0001
in which R30, R31 and R32, which are identical or different, represent a hydrogen or halogen atom or a group chosen from: alkyl; alkoxy optionally substituted by one or more hydroxyl groups, alkylthio optionally substituted by one or more hydroxyl groups; hydroxyl, mercapto; nitro, nitroso; polyhaloalkyl;
R°-C(X)-X'-, R°-X'-C(X)-, R°-X'-C(X)-X"- with R°, X, X' and X" as defined above;
M+(0')S(0)2- with M+ as defined above;
M+(O')CO- with M+ as defined above;
(di) (alky 1) amino ;
(di) (hydroxy alky 1) amino ; heterocycloalkyl, such as piperidino, piperazino or morpholino; in particular, R30, R31 and R32 represent a hydrogen atom; and in which:
Rc and Rd, which are identical or different, represent a hydrogen atom or an alkyl group;
W is as defined above; W particularly represents an -NH- group;
ALK represents a linear or branched divalent Ci-Ce alkylene group; in particular, ALK represents a -CH2-CH2- group; n has the value 1 or 2; p represents an integer of between 1 and 5 inclusive; q represents an integer of between 1 and 4 inclusive; u has the value 0 or 1 ; when n has the value 1, J represents a nitro or nitroso group; particularly a nitro group; when n has the value 2, J represents an oxygen or sulfur atom or a divalent - S(O)m— radical with m representing an integer 1 or 2; preferentially, J represents an -SO2- radical;
M' represents a hydrogen atom or a cationic counterion; [Chem 17]
Figure imgf000030_0001
which is present or absent, represents a benzo group optionally substituted by one or more R30 groups as defined above; it being understood that the formulae (K) and (K') comprise at least one sulfonate M+(O" )S(O)2- radical or one carboxylate M+(O')CO- radical; preferentially sodium sulfonate.
Mention may be made, as examples of dyes of formula (K), of: Acid Brown 13 and Acid Orange 3; mention may be made, as examples of dyes of formula (K'), of: Acid Yellow 1, the sodium salt of 2,4-dinitro-l-naphthol-7-sulfonic acid, 2-piperidino-5- nitrobenzenesulfonic acid, 2-(4'-N,N-(2"-hydroxyethyl)amino-2'- nitro)anilineethanesulfonic acid, 4-P-hydroxyethylamino-3-nitrobenzenesulfonic acid; EXT D&C Yellow 7; e) the triarylmethane dyes of formula (L) below:
[Chem 18]
Figure imgf000030_0002
in which formula (L):
R33, R34, R35 and R36, which are identical or different, represent a hydrogen atom or a group chosen from alkyl, optionally substituted aryl and optionally substituted arylalkyl; particularly an alkyl and benzyl group optionally substituted by an M+(O')S(O)m- group with M+ and m as defined above;
R37, R38, R39, R40, R41, R42, R43 and R44, which are identical or different, represent a hydrogen atom or a group chosen from: alkyl; alkoxy, alkylthio;
(di) (alky 1) amino ; hydroxyl, mercapto; nitro, nitroso;
R°-C(X)-X'-, R°-X'-C(X)- or R°-X'-C(X)-X"- with R° representing a hydrogen atom or an alkyl or aryl group; X, X' and X", which are identical or different, representing an oxygen or sulfur atom or NR, with R representing a hydrogen atom or an alkyl group;
M+(O')S(O)2- with M+ representing a hydrogen atom or a cationic counterion;
M+(0')C0- with M+ as defined above; or else two contiguous groups R41 with R42 or R42 with R43 or R43 with R44 together form a fused benzo group: I'; with I' optionally substituted by one or more groups chosen from nitro; nitroso; M+(O')S(O)2-; hydroxyl; mercapto; (di)(alkyl)amino; R°-C(X)-X'-; R°- X'-C(X)- and R°-X'-C(X)-X"-; with M+, R°, X, X' and X" as defined above; in particular, R37 to R40 represent a hydrogen atom, and R41 to R44, which are identical or different, represent a hydroxyl or M+(O')S(O)2- group; and when R43 with R44 together form a benzo group, it is preferentially substituted by an (O')S(O)2- group; it being understood that at least one of the rings G, H, I or I' comprises at least one sulfonate (O')S(O)2- radical or one carboxylate (O')CO- radical; preferentially sulfonate.
Mention may be made, as examples of dyes of formula (L), of: Acid Blue 1, Acid Blue 3, Acid Blue 7, Acid Blue 9, Acid Violet 49, Acid Green 3, Acid Green 5, Acid Green 50. f) the xanthene-derived dyes of formula (M) below:
[Chem 19]
Figure imgf000031_0001
in which formula (M) R45, R46, R47 and R48, which are identical or different, represent a hydrogen atom or a halogen atom and R49, R50, R51 and R52, which are identical or different, represent a hydrogen or halogen atom or a group chosen from: alkyl; alkoxy, alkylthio; hydroxyl, mercapto; nitro, nitroso;
M+(0')S(0)2- with M+ representing a hydrogen atom or a cationic counterion; M+(O')CO- with M+ as defined above; in particular, R49, R50, R51 and R52 represent a hydrogen or halogen atom; and in which:
G represents an oxygen or sulfur atom or an NRe group with Re representing a hydrogen atom or an alkyl group; in particular, G represents an oxygen atom;
L represents an alkoxide M+O"; a thioalkoxide M+S" or an NRf group, with Rf representing a hydrogen atom or an alkyl group, and M+ as defined above; M+ is particularly sodium or potassium;
L' represents an oxygen or sulfur atom or an ammonium group: N+RfRg, with Rf and Rg, which are identical or different, representing a hydrogen atom or an optionally substituted alkyl or aryl group; L' particularly represents an oxygen atom or a phenylamino group optionally substituted by one or more alkyl or M+(O')S(O)m- groups with m and M+ as defined above;
Q and Q', which are identical or different, represent an oxygen or sulfur atom; in particular, Q and Q' represent an oxygen atom;
M+ is as defined above.
Mention may in particular be made, as colorants suitable for the invention, of synthetic or natural water-soluble dyes, such as, for example, FDC Red 4, DC Red 6, DC Red 22, DC Red 28, DC Red 30, DC Red 33, DC Orange 4, DC Yellow 5, DC Yellow 6, DC Yellow 8, FDC Green 3, DC Green 5, FDC Blue 1 and their mixtures, more preferentially chosen from FDC Red 4, DC Red 33, DC Orange 4, DC Yellow 5, DC Green 5 and FDC Blue 1, and also their mixtures.
Mention may be made, among the natural direct dyes which can be used according to the invention as colorant, of lawsone, juglone, alizarin, purpurin, carmine and carminic acid, kermesic acid, purpurogallin, protocatechualdehyde, indigo, isatin, curcumin, spinulosin, apigenidin, orceins, betanin (beetroot), chlorophyllin metal complexes, in particular copper chlorophyllin, methylene blue, caramel, sandalwood, gardenia, spirulina and riboflavin.
Preferably, mention may in particular be made, as water-soluble dyes suitable for the invention, of synthetic or natural water-soluble dyes, such as, for example, FDC Red 4, DC Red 6, DC Red 22, DC Red 28, DC Red 30, DC Red 33, DC Orange 4, DC Yellow 5, DC Yellow 6, DC Yellow 8, FDC Green 3, DC Green 5, FDC Blue 1, betanin (beetroot), carmine, copper chlorophyllin, methylene blue, ortho -diphenol derivatives, in particular anthocyanins (red radish, red cabbage, purple sweet potato, purple maize, black carrot, hibiscus, blue pea or elder), caramel, sandalwood, gardenia, spirulina and riboflavin.
The water-soluble colorants suitable for the invention can be in the form of salts of acids or of bases, in particular inorganic or organic acids, in particular hydrochloric acid, or inorganic or organic bases, such as alkali metal hydroxides, including sodium hydroxide.
The water-soluble colorants suitable for the invention can be glycosylated, that is to say comprise one or more glycosyl groups.
All the enantiomers of the colorants defined above may be suitable as colorant, as well as the racemic mixtures.
The water-soluble colorant, in particular resulting from natural extract(s), suitable for the invention can be provided in any form which makes possible its dissolution in the fragranced composition, in particular in an aqueous, alcoholic or aqueous/alcoholic medium. It can in particular be in powder or liquid form, preferably in powder form.
For obvious reasons, the amount of water-soluble colorants(s) present in a composition according to the invention is liable to vary significantly from the viewpoint of the tint or the chromatic intensity sought by its presence.
Preferably, the water-soluble colorant(s) present in the composition according to the invention represent(s) from 0.0001% to 20% by weight of the total weight of the composition(s) containing the colorant(s) or the extract(s) containing them.
As regards the pure water-soluble colorant(s) b), the content in the fragrancing composition containing them preferably varies from 0.0001% to 5% by weight, preferably from 0.001% to 3.0% by weight, more preferentially from 0.01% to 1.0% by weight and more preferentially still from 0.1% to 0.5% by weight of water-soluble colorant(s), with respect to the total weight of said composition.
According to a specific embodiment of the invention, the total amount of water-soluble colorant(s) contained in the composition varies from 1 to 300 ppm (part(s) per million) and more particularly from 1 to 200 ppm.
Advantageously, a content of water-soluble colorant(s) of less than or equal to 300 ppm in the fragranced coloured composition makes it possible to prevent the formation of marks during its application, in particular on clothing, this being the case whatever the colorant employed.
As mentioned above, the water-soluble colorant can be introduced into the fragranced composition of the invention in the form of a natural extract.
Thus, a fragranced composition according to the invention can comprise from 0.05% to 15% by weight of natural extract comprising a water-soluble colorant, with respect to the total weight of said composition.
Preferably, a composition according to the invention comprises from 0.0001% to 20% by weight of the water-soluble colorant(s), with respect to the total weight of the composition containing the colorant(s) or the extract(s) containing them, preferably:
- when the water-soluble colorant(s) is (are) pure, the content in the fragrancing composition varies from 0.0001% to 5% by weight, preferably from 0.001% to 3.0% by weight, more preferentially from 0.01% to 1.0% by weight and more preferentially still from 0.1% to 0.5% by weight of the water-soluble colorant(s), with respect to the total weight of said composition;
- when the water-soluble colorant(s) is (are) in the form of extract(s), the content of extract(s) in the composition varies from 0.01% to 20% by weight, particularly from 0.1% to 10% by weight, particularly from 0.2% to 8.0% by weight, preferentially from 0.3% to 3.0% by weight and more preferentially from 0.4% to 2.0% by weight, better still from 0.5% to 1% by weight, of extract(s) in said composition, with respect to the total weight of said composition.
Fragrancing substance
As mentioned above, a fragranced composition according to the invention comprises at least one fragrancing substance.
Fragrances are compositions containing in particular 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.
A fragranced composition according to the invention preferably comprises at least one fragrancing substance chosen from essential oils, fragrances and aromas of synthetic or natural origin, and their mixtures. They can be natural products, such as essential oils, absolutes, resinoids, resins, concretes and/or synthetic products, such as terpene or sesquiterpene hydrocarbons, alcohols, phenols, aldehydes, ketones, ethers, acids, esters, nitriles or peroxides, which are saturated or unsaturated, aliphatic or cyclic.
According to the definition given in International Standard ISO 9235 and adopted by the European Pharmacopoeia Commission, 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 by an appropriate mechanical process without heating (cold expression). The essential oil is generally separated from the aqueous phase by a physical process which does not result in any significant change in the composition.
The choice of the method for obtaining the essential oils depends mainly on the starting material: its original state and its characteristics, its intrinsic nature. The “ essential oil/plant starting material” yield can be extremely variable depending on the plants: 15 ppm to more than 20%. This choice determines the characteristics of the essential oil, in particular viscosity, colour, solubility, volatility, and enrichment or depletion in certain constituents. Steam distillation corresponds to the vaporization, in the presence of steam, of a sparingly water-miscible substance. The starting material is placed in contact with boiling water or steam in a still. The steam entrains the essential oil vapour, which is condensed in the condenser in order to be recovered as liquid phase in a Florentine flask (or essence jar), where the essential oil is separated from the water by settling. The aqueous distillate which remains in the steam distillation, once the essential oil has been separated, is known as the “aromatic water” or “hydrolate” or “distilled floral water”.
Production by dry distillation consists in obtaining the essential oil by distillation of wood, bark or roots, without addition of water or steam, in a closed chamber designed in order for the liquid to be recovered in its bottom part. Cade oil is the most well known example of this method of production.
The cold expression production method is applied only to citrus fruits (Citrus spp.) by mechanical processes at ambient temperature. The principle of the method is as follows: the peel is shredded and the contents of the secretory cavities which have been ruptured are recovered by a physical process. The conventional process consists in exerting an abrasive action over the entire surface of the fruit under a stream of water. After removal of the solid waste, the essential oil is separated from the aqueous phase by centrifugation. The majority of industrial plants in fact allow the simultaneous or sequential recovery of the fruit juices and of the essential oil.
Essential oils are generally volatile and liquid at ambient temperature, which differentiates them from “fixed” oils. They are more or less coloured and their density is generally lower than that of water. They have a high refractive index and the majority deviate polarized light. They are soluble in fats and in standard organic solvents, can be steam distilled and exhibit a very low solubility in water.
Mention may be made, among the essential oils which can be used according to the invention, of those obtained from plants belonging to the following botanical families: Abietaceae or Pinaceae, for example conifers; Amaryllidaceae; Anacardiaceae; Annonaceae, for example ylang-ylang; Apiaceae, for example umbellifers, in particular dill, angelica, coriander, sea fennel, carrot or parsley; Araceae; Aristolochiaceae; Asteraceae, for example Achillea, Artemisia, camomile, Helichrysum; Betulaceae; Brassicaceae; Burseraceae, for example frankincense; Caryophyllaceae; Canellaceae; Caesalpiniaceae, for example Copaifera (copaiba); Chenopodiaceae; Cistaceae, for example Cistus; Cyperaceae; Dipterocarpaceae; Ericaceae, for example gaultheria (wintergreen); Euphorbiaceae; Fabaceae; Geraniaceae, for example geranium; Guttiferae; Hamamelidaceae; Hemandiaceae; Hypericaceae, for example St. John’s wort; Iridaceae; Juglandaceae; Lamiaceae, for example thyme, oregano, Monarda, savory, basil, marjorams, mints, patchouli, lavenders, sages, catnip, rosemary, hyssop or balm; Lauraceae, for example Ravensara, bay, rosewood, cinnamon, Litsea; Liliaceae, for example garlic; Magnoliaceae, for example magnolia; Malvaceae; Meliaceae; Monimiaceae; Moraceae, for example hemp or hop; Myricaceae; Myristicaceae, for example nutmeg; Myrtaceae, for example eucalyptus, tea tree, Melaleuca quinquenervia, cajuput, Backhousia, clove, myrtle; Oleaceae; Piperaceae, for example pepper; Pittosporaceae; Poaceae, for example citronella grass, lemon grass, vetiver; Polygonaceae; Ranunculaceae; Rosaceae, for example roses; Rubiaceae; Rutaceae, for example the whole citrus family; Salicaceae; Santalaceae, for example sandalwood; Saxifragaceae; Schisandraceae; Styracaceae, for example benzoin; Thymelaeaceae, for example agarwood; Tiliaceae; Valerianaceae, for example valerian, nard; Verbenaceae, for example lantana, verbena; Violaceae; Zingiberaceae, for example galangal, turmeric, cardamom, ginger; Zygophyllaceae. Mention may also be made of essential oils extracted from flowers (lily, lavender, rose, jasmine, ylang-ylang, neroli), from stalks and leaves (patchouli, geranium, bitter orange), from fruits (coriander, anise, cumin, juniper berry), from fruit peels (bergamot, lemon, orange), from roots (angelica, celery, cardamom, iris, sweet flag, ginger), from wood (pinewood, sandalwood, guaiac, pink cedar, camphor), from grasses and graminae (tarragon, rosemary, basil, lemon grass, sage, thyme), from needles and branches (spruce, fir, pine, dwarf pine) or from resins and balms (galbanum, elemi, benzoin, myrrh, olibanum, opopanax).
Examples of fragrancing substances are in particular: geraniol, geranyl acetate, farnesol, borneol, bornyl acetate, linalol, linalyl acetate, linalyl propionate, linalyl butyrate, tetrahydrolinalol, 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 salicylate, dimethylbenzylcarbinol, trichloromethylphenylcarbinyl acetate, p-tert-butylcyclohexyl acetate, isononyl acetate, vetiveryl acetate, vetiverol, a-hexylcinnamaldehyde, 2-methyl-3- (p-tert-butylphenyl)propanal, 2-methyl-3-(p-isopropylphenyl)propanal, 3-(p-tert- butylphenyl)propanal, 2,4-dimethylcyclohex-3-enylcarboxaldehyde, tricyclodecenyl acetate, tricyclodecenyl propionate, 4-(4-hydroxy-4-methylpentyl)-3- cyclohexenecarboxaldehyde, 4-(4-methyl-3-pentenyl)-3-cyclohexenecarboxaldehyde, 4- acetoxy-3-pentyltetrahydropyran, 3-carboxymethyl-2-pentylcyclopentane, 2-(n- heptyl)cyclopentanone, 3-methyl-2-pentyl-2-cyclopentenone, menthone, carvone, tagetone, geranylacetone, n-decanal, n-dodecanal, 9-decen-l-ol, phenoxyethyl isobutyrate, phenylacetaldehyde dimethyl acetal, phenylacetaldehyde diethyl acetal, geranonitrile, citronellonitrile, cedryl acetate, 3-isocamphylcyclohexanol, cedryl methyl ether, isolongifolanone, anisonitrile, anisaldehyde, heliotropin, coumarin, eugenol, vanillin, diphenyl ether, citral, citronellal, hydroxycitronellal, damascene, ionones, methylionones, isomethylionones, solanone, irones, cis-3-hexenol and its esters, indane musk compounds, tetralin musk compounds, isochroman musk compounds, macrocyclic ketones, macrolactone musk compounds, aliphatic musk compounds, ethylene brassylate and their mixtures. A fragranced composition according to the invention preferably comprises a fragrancing substance chosen from essential oils, fragrances and aromas of synthetic or natural origin, and their mixtures.
According to a preferred embodiment of the invention, use is made of a mixture of different fragrancing substances which generate in common a note which is pleasant to the user.
Thus, according to a preferred embodiment, the fragranced composition comprises at least 1% by weight of a mixture of fragrancing substances, in particular of at least two distinct fragrancing substances, with respect to the total weight of the composition, and preferably of at least three distinct fragrancing substances.
The fragrancing substances will preferably be chosen so that they produce notes (top, middle and base) in the following families: hesperidic, aromatic, floral notes, in particular pink flowers and white flowers, spicy, woody, gourmand, chypre, fougere, leather and musk.
For obvious reasons, the amount of fragrancing substance(s) present in a composition according to the invention is liable to vary significantly from the viewpoint of the odour or of the odorous intensity sought by its presence.
By way of illustration, a fragranced composition according to the invention can comprise from 0.0001% to 10% by weight, particularly from 0.001% to 8.0% by weight, more particularly from 0.01% to 5.0% by weight, preferentially from 0.1% to 1.0% by weight, of fragrancing substance(s), with respect to the total weight of said composition.
As mentioned above, the fragrancing substances can be introduced into a fragranced composition in accordance with the invention in the form of a fragrance concentrate.
The fragrance concentrate can be a concrete or an absolute, preferably an absolute.
Thus, a fragranced composition according to the invention comprises in particular from 1.0% to 50% by weight of fragrance concentrate, more particularly from 2.0% to 40% by weight, preferentially from 5.0% to 30% by weight, more preferentially from 10% to 20% by weight, for example 15% by weight, with respect to the total weight of the composition.
Composition
A fragranced composition according to the invention can be provided in any presentation form conventionally used for a topical application and in particular in the form of an alcoholic or aqueous/alcoholic solution or suspension, of an emulsion of liquid or semiliquid consistency of the milk type, which are obtained by dispersion of a fatty phase in an aqueous phase (O/W) or vice versa (W/O), or of a suspension or emulsion of soft consistency of (O/W) or (W/O) cream type, or of an anhydrous gel, or of any other cosmetic form.
Preferably, a fragranced composition according to the invention is an alcoholic composition, namely a composition comprising an alcohol or a mixture of alcohols as solvent(s), or an aqueous/alcoholic composition, namely a composition comprising a mixture of water and of alcohol as solvents.
According to a preferred embodiment, a fragranced composition according to the invention is an alcoholic or aqueous/alcoholic composition; preferably, the composition comprises as solvent(s) ethanol, optionally as a mixture with water and/or pentylene glycol.
Preferably, the composition according to the invention is aqueous/alcoholic.
Besides the ethanol present in a content strictly greater than 15% by weight, a composition according to the invention can additionally comprise other alcohols distinct from ethanol, referred to as “additional alcohols”.
Additional alcohols
The additional alcohols very particularly suitable for the invention are chosen from i) monoalcohols having from 3 to 6 carbon atoms, such as isopropanol, and ii) glycols having from 2 to 8 carbon atoms, such as ethylene glycol, propylene glycol, 1,3 -butylene glycol, pentylene glycol and dipropylene glycol.
In particular, a fragranced composition according to the invention comprises, as solvent(s), water and (bio)ethanol, optionally as a mixture with pentylene glycol.
Preferably, the composition of the invention comprises a content of additional alcohols ranging from 0.01% to 80% by weight, particularly from 0.01% to 50% by weight.
Water-soluble solvents
A composition according to the invention is preferably aqueous/alcoholic.
An aqueous/alcoholic fragranced composition according to the invention can comprise, besides water and ethanol, one or more water-soluble solvents distinct from the additional alcohols defined above. In the present invention, the term “water-soluble solvent” denotes a compound which is liquid at ambient temperature and miscible with water (miscibility in water of greater than 50% by weight at a temperature ranging from 20°C to 25°C and atmospheric pressure).
The water-soluble solvents which can be used in the composition of the invention can additionally be volatile. Mention may in particular be made, among the water-soluble solvents which can be used in the composition in accordance with the invention, of C3 and C4 ketones and C2-C4 aldehydes.
Alternatively, a fragranced composition according to the invention can be anhydrous, namely that it comprises less than 2% by weight of water, preferably less than 1% by weight of water, preferentially less than 0.5% by weight of water, indeed even is totally devoid of water.
Polyols
A fragranced composition according to the invention can also comprise at least one C2-C32 polyol. Within the meaning of the present invention, the term “polyol” should be understood as meaning any organic molecule comprising at least three free hydroxyl (-OH) groups. Preferably, a polyol in accordance with the present invention is present in liquid form at ambient temperature. A polyol suitable for the invention can be a compound of saturated or unsaturated and linear, branched or cyclic alkyl type carrying, on the alkyl chain, at least three -OH functions, in particular at least four -OH functions.
The polyols advantageously suitable for the formulation of a composition according to the present invention are those exhibiting in particular from 2 to 32 carbon atoms, preferably from 3 to 16 carbon atoms.
Preferably, the polyol can, for example, be chosen from pentaerythritol, trimethylolpropane, glycerol, polyglycerols, in particular glycerol oligomers, preferably diglycerol, and their mixtures.
Fatty substance
A fragranced composition according to the invention can comprise one or more fatty substances which are liquid at ambient temperature and/or a fatty substance which is solid at ambient temperature, such as waxes, pasty fatty substances, gums and their mixtures. Within the meaning of the invention, the term “ ambient temperature" is understood to mean a temperature equal to 25°C.
Preferably, the fatty substances suitable for the present invention are liquid at ambient temperature and at atmospheric pressure.
The oils can be polar or non-polar, of different chemical natures, alone or as a mixture.
In particular, mention may be made, as polar oils, of: hydrocarbon vegetable oils having a high content of triglycerides constituted of esters of fatty acids and of glycerol, for example like wheat germ oil, maize oil, sunflower oil, shea oil, castor oil and sweet almond oil; synthetic esters and ethers; saturated C12 to C26 fatty alcohols; and their mixtures.
Moreover, the non-polar oils can be chosen in particular from silicone oils, such as volatile or non-volatile, linear or cyclic, polydimethylsiloxanes which are liquid at ambient temperature (20°C ± 5°C) and atmospheric pressure, and linear or branched hydrocarbons of synthetic or mineral origin.
Mention may be made, as examples of solid fatty substances, of waxes, in particular hydrocarbon or silicone waxes, of natural or synthetic origin, in so far as they are compatible with the other components of the composition and in so far as they do not detrimentally affect the properties, in particular olfactory and colour properties, of the fragranced composition.
Preferably, the fatty substances are vegetable oils. Mention may be made, as vegetable oils, of sunflower oil, virgin olive oil, refined sesame oil, and the like.
Surfactants
A fragranced composition according to the invention can also comprise one or more anionic, cationic, non-ionic, zwitterionic or amphoteric surfactants.
Mention may very particularly be made, as non-ionic surfactants, of esters of fatty acid and of sugars, in particular those chosen from the group consisting of esters or mixtures of esters of C8-C22 fatty acid and of sucrose, of maltose, of glucose or of fructose, and esters or mixtures of esters of C14-C22 fatty acid and of methyl glucose. Mention may be made, as examples of esters or of mixtures of esters of fatty acid and of sucrose, of maltose, of glucose or of fructose, of sucrose monostearate, sucrose distearate, sucrose tristearate and their mixtures, and, as examples of esters or of mixtures of esters of fatty acid and of methyl glucose, of Polyglyceryl-3 Methylglucose Distearate, sold by Goldschmidt under the name Tego-Care 450.
In addition, the fragranced composition according to the invention can comprise one or more co-emulsifiers. This or these co-emulsifiers can be chosen, for example, from C16-C22 fatty alcohols or esters of C3-C6 polyols with C14-C22 fatty acids, and their mixtures. Mention may be made, as co-emulsifiers, for example, of cetyl alcohol, stearyl alcohol, cetearyl alcohol (mixture of cetyl alcohol and of stearyl alcohol), glyceryl stearate and their mixtures, and preferably cetyl alcohol.
A fragranced composition can comprise from 0.01% to 10% by weight, more particularly from 0.1% to 5% by weight, and preferentially comprises from 1% to 3% by weight, of surfactant(s), with respect to the total weight of the fragranced composition.
Preservatives
A fragranced composition according to the invention can additionally comprise at least one preservative.
The term “preservative” or “preserving agent” is understood to mean any cosmetically or pharmaceutically acceptable compound which makes it possible to prevent microbial growth (or the growth of microorganisms) which can take place in cosmetic or pharmaceutical compositions, from the moment of their preparation, while they are in storage and up to the time of their conventional use by consumers. Mention may in particular be made, as preservatives, of the preservatives described in Cosmetics, Kirk-Othmer Encyclopedia of Chemical Technology, John Wiley & Sons Inc., Martin M. Rieger; 5.2 Preservatives & Table 3, 04/12/2000, https://doi.org/10.1002/all0471238961.0315191318090507.a01.
According to a specific embodiment, the preservative(s) are chosen from organic preservatives having an aromatic group.
A fragranced composition according to the invention can additionally comprise at least one preservative, in particular chosen from i) benzenecarboxylic acids optionally substituted on the phenyl group by one or more groups chosen from hydroxyl, (Ci-Cio)alkyl and (Ci- Cio)alkylcarbonyl, and also their salts of bases, in particular of alkali metals and alkaline earth metals, ii) hydroxybenzoic acid esters optionally substituted on the phenyl group by one or more groups chosen from (Ci-Cio)alkyl, such as parabens, in particular methylparaben and ethylparaben and propylparaben, and iii) aromatic alcohols. Preferably, the preservative(s) other than a) are chosen from i) and in particular benzoic acid [CAS No. 65-85-0] and also its salts of bases, in particular of alkali metals and alkaline earth metals; and also salicylic acid optionally substituted by a (Ci-Cs)alkylcarbonyl group, preferably salicylic acid. The preservative(s) are in particular chosen from aryl(Ci-C6)alkanols and aryloxy(Ci-C6)alkanols, such as phenylethanol, parabens, such as propylparaben, methylparaben, butylparaben, ethylparaben or isobutylparaben, benzyl alcohol and/or chlorophenesin.
Alkaline agents
A fragranced composition according to the invention can also comprise at least one organic or inorganic alkaline agent, for example an amine, in particular a (C2-C6)alkanolamine, in particular 2-amino-2-methyl-l -propanol, or an inorganic alkaline agent, such as, for example, alkali metal or alkaline earth metal hydroxides, such as sodium hydroxide.
Chelating agents
According to a specific embodiment of the invention, the composition comprises one or more chelating agents.
The term “chelating agent” is understood to mean a ligand or chelating agent which makes it possible to form a metal complex, referred to as chelate, with a metal cation or atom. Generally, the chelating agent is electron-donating and the chelated entity is electrondeficient. A “chelate” differs from a simple “complex” in that the metal cation is attached to the chelating ligand or chelating agent via at least two coordination bonds. The metal is thus “gripped” between the chemical functions of the ligand. The number of metal-ligand bonds of a ligand molecule defines the “denticity”: such coordinates or ligands are referred to as being bidentate, tridentate or tetradentate. The central atom is bonded to the neighbouring atoms via at least two bonds, forming a ring structure, a chelate ring. The most stable chelate rings are 5- and 6-membered chelate rings. By virtue of this effect, chelates are more stable complexes than the complexes of monodentate ligands comprising the same chemical functions. In particular, the chelating agent(s) are chosen from aminocarboxylic acids, for example ethylenediaminetetraacetic acid (EDTA), aminotriacetic acid, diethylenetriaminepentaacetic acid, and their salts, in particular alkaline salts, such as disodium EDTA or dipotassium EDTA, aminopoly carboxy lie acids, such as ethylenediaminedisuccinic acid (EDDS), and their salts, in particular alkaline salts, or else one or more phosphate -based chelating agents, such as alkali metal metaphosphates, such as sodium metaphosphate, alkali metal hexametaphosphates, such as sodium hexametaphosphate, tetra-alkaline pyrophosphates, such as tetrapotassium pyrophosphate, phosphorus-containing acids, such as phytic acid, and their salts, in particular alkaline or alkaline earth salts, such as ethylenediaminetetramethylenephosphonic acid salts, alkali metal phytates, such as sodium phytate or potassium phytate, and their mixtures, preferably chosen from EDTA as defined above and alkali metal phytates, such as sodium phytate.
Metal salts
According to a specific embodiment of the invention, the composition of the invention comprises one or more metal salts, metal complexes, metal oxides, metal oxoanions, the hydrates and their supported forms.
Preferably, a composition according to the invention comprises one or more metal salts.
More particularly, the metal(s) are of oxidation state I or II, more particularly II, preferably chosen from 1) Cu, 2) Fe, 3) Zn, 4) Mg and 5) Mn.
The term “metal salt” is understood to mean a compound other than alloys, i.e. the salt is constituted of a metal combined with certain non-metal elements.
The formation of metal salts derives from an oxidative attack. The metal is oxidized to give a cationic entity and then combines with an anionic entity to give a salt. This formation takes place by applying redox principles and the redox reaction (chemical reaction during which an electron transfer takes place in which the atom which captures the electrons is known as the “oxidizing agent”; the atom that gives up the electrons is known as the “reducing agent”); or via chemical exchange reactions between one salt and another salt or an acid, in the presence or absence of atmospheric oxygen. These reactions are known to a person skilled in the art.
Preferentially, the salts according to the invention are soluble in water at a proportion of at least 0.0001 gd. The metal salts according to the invention can be introduced in solid form into the compositions or else originate from a mineral or thermal natural water which is rich in these ions, or also from seawater (in particular Dead Sea water). They can also originate from mineral compounds, such as plant extracts containing them (cf., for example, the document FR 2 814 943).
The term “metal complex’" or “coordination compounds'” is understood to mean systems in which the metal ion, the central atom, is chemically bonded to one or more electron donors (ligands). A ligand comprising various coordinating groups (groups capable of coordinating with a metal) gives metal compounds corresponding to principles of a coordination sphere having a predetermined number of electrons (internal complexes or chelates), as described in Ullmann’s Encyclopedia of Industrial Chemistry, “Metal complex dyes”, 2005, pages 1- 42.
More particularly, the term “metal complex” is understood to mean: i) metal dyes or “metal-complex dyes”, which are complexed dyes resulting from azo, azomethine, hydrazono or formazan dyes (free, bidentate, tridentate, tetradentate), such as those described in Ullmann’s Encyclopedia of Industrial Chemistry, “Metal complex dyes”, 2005, pages 1-42, which preferentially comprise Cu and Mg; ii) compounds of “aza[18]annulene” type, also known as “(metallo)porphyrins” and “phthalocyanines” , which contain 4 and 8 nitrogen atoms respectively included in the perimeter of the macrocycle, as described in the work “Color Chemistry”, H. Zollinger, 3rd Ed., Wiley-VCH, 2003, chapter 5, Aza[ 18] annulenes, pages 123-160. The metal ion is then found at the centre of said macrocycle bonded by coordination with two hydrogen atoms to the nitrogen atoms of pyrroles, it also being possible for the metal to be stabilized by one or more bidentate or non-bidentate ligands, the metal ion preferentially being Mg2+ or Cu2+; the metal complex is particularly:
- a “metalloporphyrin” constituted of a backbone having 4 pyrrole groups that are connected at their a, a’ positions via 4 methine groups and contain 16 sp2 hybridized atoms, complexing a metal such as Cu or Mg, or
- a “chlorine” (corresponding to a porphyrin, an external C=C double bond of a pyrrole group of which has been reduced) complexed to a metal, preferentially Mg2+, such as the chromophore of chlorophyll: chlorophyllin; - “phthalocyanines", which are tetraaza analogues of tetrabenzoporphyrins, such as Monastral Fast Blue B (C.I. Pigment Blue 15); Monastral Fast Blue G (C.I. Pigment Blue 16) (see “ Color Chemistry" , H. Zollinger, 3rd Ed., Wiley -VCH, 2003, chapter 5, Aza[18]annulenes, page 140); the sulfonylated derivatives Sirius Light Turquoise Blue G (C.I. Direct Blue 86, copper phthalocyanine tetrasulfonic acid) and the ''Phthalocyanines'' as described in Ullmann’s Encyclopedia of Industrial Chemistry, ''Phthalocyanines ', 2005, pages 1-34, which comprise Cu and Si.
The term “ metal oxide(s)" is understood to mean compounds of generic formula AAOV with A representing a metal element, x being greater than or equal to 1 and less than or equal to 4, and y being greater than or equal to 1 and less than or equal to 12.
The term “metal oxoanion(s)" is understood to mean compounds of generic formula ZZAAOI with A representing a metal element, Z representing an alkali metal, such as Li, Na or K, or a hydrogen atom or an ammonium ion, z being greater than or equal to 1 and less than or equal to 6, x being greater than or equal to 1 and less than or equal to 4, and y being greater than or equal to 1 and less than or equal to 12.
The term “ supported form(s)” is understood to mean the forms where the metal derivative b) is impregnated onto a material known as a “support”. The optional supports of these metal derivatives can be chosen from charcoal, silica, alumina, optionally charged polymers comprising counter-anions or counter-cations (counter-cation or counter-anion of the metal entity). By way of example, the polymers can be polyethylene glycol (PEG).
According to one embodiment of the invention, the metal salt(s) are chosen from the (poly)hydroxy(Ci-Ci6)alkylcarboxylates of metals of oxidation state II, in particular Fe(II), Cu(II), Zn(II), Mg(II) and Mn(II) (poly)hydroxy(Ci-Ci6)alkylcarboxylates. In particular, the metal salt(s) are chosen from Cu gluconate, Fe gluconate, Zn gluconate or Mg gluconate, gluconates of metals of oxidation state II, such as Fe, Cu, Zn or Mg gluconates, or lactates of metals of oxidation state II, such as Fe, Cu, Zn or Mg lactates. Preferably, the metal salts are Fe, Cu, Mg or Zn gluconate, preferably Fe gluconate and Cu gluconate.
Aqueous pH buffers
A fragranced composition according to the invention can also comprise at least one aqueous pH buffer, namely at least one compound which makes it possible to maintain a constant pH in aqueous solution. The aqueous pH buffer(s) particularly suitable for the invention can be chosen from benzoic acid, maleic acid, fumaric acid, succinic acid and their salts, in particular alkali metal or alkaline earth metal salts, for example sodium benzoate.
Additional colorants
A fragranced composition according to the invention can also comprise one or more additional colorants, distinct from the water-soluble dyes defined above.
This (or these) colorant(s) is (or are) preferably chosen from fat-soluble dyes, particulate colorants and their mixtures.
Within the meaning of the invention, the term "'fat-soluble dye” is understood to denote any natural or synthetic, generally organic, dye soluble in an oily phase or solvents miscible with a fatty substance.
The particulate colorants can be coloured pigments (i.e., other than the pigment UV screening agents), pearlescent agents and/or particles having metallic glints.
Within the meaning of the present invention, the term "pigments” is understood to denote white or coloured and inorganic or organic solid particles.
Pigments are naturally insoluble in the liquid hydrophilic and lipophilic phases usually employed in cosmetics. Alternatively, they can be rendered insoluble by formulation in lake form, if appropriate.
More particularly, the pigment has little or no solubility in aqueous/alcoholic media.
The pigments can be white or coloured, inorganic and/or organic, and coated or uncoated. Mention may be made, among the inorganic pigments, of metal oxides, in particular titanium dioxide, optionally surface-treated, zirconium oxide, zinc oxide or cerium oxide, and also iron oxide, titanium oxide or chromium oxide, manganese violet, ultramarine blue, chromium hydrate and ferric blue.
These additional colorants can be present in a content ranging from 0.01% to 30% by weight, with respect to the total weight of the composition, in particular from 0.05% to 20% by weight, with respect to the total weight of the composition.
Adjuvants
A fragranced composition according to the invention can additionally comprise any adjuvant usually used in the field of fragrances, such as, for example, emollients or softeners, in particular sweet almond oil or apricot kernel oil, moisturizing agents, in particular glycerol, soothing agents, in particular a-bisabolol, allantoin and Aloe vera; vitamins and their derivatives, essential fatty acids, propellants, peptizing agents, fillers, cosolvents, UV screening agents, stabilizers or preservatives distinct from the compounds of formula (I) as are defined according to the invention, and their mixtures.
It is a matter of routine operations for a person skilled in the art to adjust the nature and the amount of the adjuvants present in the compositions in accordance with the invention so that the cosmetic properties desired for the compositions are not thereby affected.
When they are present in the composition of the invention, these adjuvants can be present in an amount ranging from 0.001% to 10% by weight and better still from 0.01% to 5% by weight, with respect to the total weight of the composition.
Preparation of the composition
A composition according to the invention can be obtained by any method known to a person skilled in the art for the formulation of coloured fragranced compositions.
In particular, a fragranced composition according to the invention can be obtained by simple mixing, at ambient temperature, namely at a temperature ranging from 20°C to 25°C, of the compounds constituting the composition.
According to a specific embodiment, a fragranced composition according to the invention results from the mixing between a colouring solution, on the one hand, and a fragranced solution comprising the compound of formula (I), on the other hand.
Said colouring solution thus comprises at least one colorant, in particular as defined above, in a physiologically acceptable medium, in particular an aqueous or aqueous/alcoholic medium.
Said fragranced solution comprises, for its part, at least one fragrancing substance, in particular as defined above, at least one compound of formula (I) as defined above, and ethanol in a content sufficient for the final composition to comprise strictly more than 15% by weight of ethanol, with respect to its total weight, in a physiologically acceptable medium. Said fragranced solution can itself result from mixing between an intermediate fragranced solution, comprising at least one fragrancing substance, in particular as defined above, in a physiologically acceptable medium, in particular in an aqueous or aqueous/alcoholic medium, and a compound of formula (I) as defined above, directly or which is in solution in a physiologically acceptable medium, in particular in an aqueous or aqueous/alcoholic medium.
Alternatively, the compound(s) of formula (I) can be introduced, directly or in solution, into a fragranced composition, additionally comprising at least one fragrancing substance, at least one colorant, and ethanol in a content sufficient for the final composition to comprise strictly more than 15% by weight of ethanol, with respect to its total weight, in a physiologically acceptable medium.
It is within the competence of a person skilled in the art to adapt the conditions of preparation of a fragranced composition according to the invention.
Purpose of the composition
The invention applies not only to fragrancing products but also to cosmetic treatment or care products for keratin materials, in particular the skin, including the scalp, and the lips, containing an odorous substance.
A composition according to the invention can thus constitute a cosmetic treatment, care or fragrancing composition for keratin materials, and in particular be provided in the form of an eau fraiche, an eau de toilette, an eau de parfum, an aftershave lotion, an eau de soin or a silicone or hydrosilicone care oil. It can also be provided in the form of a fragranced two- phase lotion (eau de toilette phase/hydrocarbon oil and/or silicone oil phase), a body milk or a shampoo.
The compositions according to the invention can be packaged in the form of bottles.
A fragrancing composition according to the invention can be diffused according to various systems, such as sprays, aerosols or piezoelectric devices.
It can also be applied in the form of fine particles by means of mechanical or propellant gas pressurization devices. The devices in accordance with the invention are well known to a person skilled in the art and comprise pump-action sprays, aerosol containers comprising a propellant and also aerosol pumps using compressed air as propellant. The latter are in particular described in Patents US 4 077 441 and US 4 850 517.
The compositions packaged as aerosols in accordance with the invention generally contain conventional propellants, such as, for example, dimethyl ether, isobutane, n-butane or propane. According to a specific form of the invention, the compositions according to the invention are lotions and preferably have a viscosity ranging from 10 to 120 DU, more preferentially from 30 to 120 DU and more preferentially still from 40 to 80 DU; the viscosity being measured using a Rheomat TVe-05 device, at 25 °C, rotational speed 200 revolutions/min, spindle 1, 10 minutes.
These low viscosities make it possible to package the compositions of the invention by means of mechanical or propellant gas pressurization devices so as to be applied in the form of fine particles (vaporization).
A fragranced composition according to the invention can also be in the form of a body milk or also in the form of a shampoo.
The invention is illustrated in greater detail by the examples presented below. Unless otherwise indicated, the amounts indicated are expressed as percentages by weight.
Examples
Measurement and evaluation methods
The stability of the compositions is evaluated by observation of the change in the colour over time, visually and using a Konica Minolta CM 3600A spectrocolorimeter (L*, a*, b*).
In particular, the compositions are poured into 50 ml bottles pots made of borosilicate glass and are then observed after storage for 2 months, at atmospheric pressure and under various conditions: a) in the refrigerator, at a temperature of 4 °C; b) at ambient temperature, namely of between 20°C and 25 °C, with the exclusion of light; c) in an oven, at a temperature of 37°C; d) in an oven, at a temperature of 45°C; or e) in natural light and at ambient temperature, namely of between 20°C and 25°C, and then, in addition: e.l) 16 hours in a SunTest CPS+ ageing device of the Atlas trade name, equipped with a xenon lamp, an irradiating light source, the spectral distribution of which is close to that of sunlight, delivering an energy of 765 W/m2, simulating exposure to neon lights in a shop; or e.2) 2 weeks in an oven at a temperature of 55°C, simulating an extreme condition for the fragrance. Storage of the compositions for 2 months at 45°C simulates an accelerated ageing of the product corresponding to a shelf life of 3 years.
The intensity difference DL between a reference composition and a composition tested after storage under the conditions mentioned above can be calculated from the L*a*b values according to the following formula:
[Math 1]
DL = L*2 - L\ in which Li* is the intensity of the colour of the reference composition and L2* is the intensity of the colour of the composition tested after storage.
Example 1
Preparation of the colouring solutions
The colouring solutions Cl to C13 are prepared using the proportions by weight as described in detail in Tables 1 and 2 below. The values are expressed as percentages by weight, with respect to the total weight of the colouring solution.
[Table 1]
Figure imgf000051_0001
Figure imgf000052_0001
Table 1
[Table 2]
Figure imgf000052_0002
Table 2 Protocol for preparation of the colouring solutions
The colouring compositions are prepared by dissolving the dyes in the appropriate solvent or mixture of solvents. In particular, for a colouring solution of 100 g, the required amount of dye is weighed out in a beaker. The amount of solvents (ethanol, water and/or propylene glycol) is subsequently added and the mixture is left stirring by magnetic stirring for 20 minutes.
Example 2 Preparation of the coloured fragranced compositions
Fragranced compositions Pl, P2, P3, P4 and P5 according to the invention and a fragranced composition P6 outside the invention are prepared using the proportions by weight as described in detail in Table 3 below.
The values are expressed as percentages by weight, with respect to the total weight of the fragranced composition.
[Table 3]
Figure imgf000053_0001
Figure imgf000054_0001
- its top notes of peach, coriander, plum, green notes type,
- its middle notes of peony, lily, freesia, lily of the valley, jasmine, ylang-ylang, rose, coffee type, and - its base notes of tonka bean, musk, vanilla, sandalwood, cedar type; and/or
(**) Fragrance of the hesperidic type, characterized by:
- its top notes of green lemon, citron, mint, eucalyptus type, and
- its middle notes of coconut type.
Table 3
Protocol for preparation of the coloured fragranced compositions Pl to P6
15 g of fragrance concentrate are weighed out in a beaker.
95° Ethanol is added to the fragrance concentrate, and then the water is subsequently added.
For the composition Pl, 0.1 g of extract containing at least 85% of rutin (Sophora Japonica Bud Extract) is added and then the mixture is left under magnetic stirring for 10 minutes, in order to obtain a fragranced solution. 0.05 g of the colouring solution is subsequently added using a pipette.
The compositions P2 to P5 are prepared according to the same protocol, the extract containing rutin being replaced by a-glycosylrutin, luteolin, myricetin or quercetin respectively. The composition P6, outside the invention, is prepared according to the same protocol, except for the addition of compound corresponding to the formula (I).
Example 3
Stability tests The stability of the coloured fragranced compositions is evaluated visually according to the protocol described in detail above.
The change in the colour of the compositions according to the invention (Pl, P2, P3, P4 and P5) and outside the invention (P6), as a function of the colouring solution used, is observed visually after 16 hours in the SunTest ageing device. The results are described in detail in Table 4 below.
[Table 4]
Figure imgf000055_0001
Figure imgf000056_0001
Table 4
The study was carried out with various fragrance concentrates of different olfactory families, similar results being obtained for each fragrance concentrate. For the fragranced compositions Pl to P5 according to the invention, the colouration is always visible, whatever the colouring solution tested, after ageing in the SunTest device. In addition, no olfactory difference was noticed after the SunTest.
On the contrary, the composition P6, not comprising compound corresponding to the formula (I) as defined according to the invention, becomes colourless after ageing. Thus, the composition according to the invention preserves its colouration for a significantly longer time. Furthermore, no significant change in odour was noticed over time.
In addition, the compound of formula (I) employed in the composition according to the invention is of natural origin.
In conclusion, the fragranced composition according to the invention is more stable over time than a composition not in accordance with the invention.

Claims

Claims 1. Fragranced composition, in particular a cosmetic composition, comprising: a) at least one compound corresponding to the formula (I), or one of its geometrical isomers, in particular optical isomers, of its tautomers, and also its organic or inorganic acid or base salts, or its solvates, in particular hydrates:
Figure imgf000057_0001
in which formula (I): represents a double bond or a single bond, ^ R1 represents an atom or a group chosen from: - a hydrogen atom, - a hydroxyl, - a (C1-C6)alkyl group, - a (C1-C6)alkoxy group, - a monoglycoside or diglycoside sugar group, such as a glycosyl group, or an - O-monoglycoside or -diglycoside sugar group, such as an -O-glycosyl group; ^ R2 represents a hydrogen atom, a (C1-C6)alkyl group or a monoglycoside or diglycoside sugar group, such as a glycosyl group, ^ R3 represents a hydrogen atom or a (C1-C6)alkyl group, ^ n represents an integer of between 1 and 3 and m represents an integer of between 0 and 3, it being understood that: when m represents an integer greater than or equal to 2, the R2 radicals can be identical or different, and when n represents an integer greater than or equal to 2, the R3 radicals can be identical or different, b) ethanol in a content strictly greater than 15% by weight, with respect to the total weight of the composition, c) at least one water-soluble colorant, and d) at least one fragrancing substance. 2. Composition according to the preceding claim, said compound of formula (I) being chosen from luteolin, quercetin, myricetin, rutin, hesperidin, narirutin, α- glycosylrutin, quercitrin, isoquercitrin, morin, hesperetin, chrysin, apigenin, luteolin-7-O- glucoside, 6-hydroxyflavone, 7,8-dihydroxyflavone or tropoflavin, and their mixtures. 3. Composition according to either one of the preceding claims, said compound of formula (I) being of formula (I'), or one of its geometrical isomers, of its tautomers, and also its organic or inorganic acid or base salts, or its solvates, in particular hydrates:
Figure imgf000058_0001
in which formula (I'): R represents an atom or a group chosen from: i) a hydrogen atom, ii) a hydroxyl, iii) a monoglycoside or diglycoside sugar group, such as a glycosyl group, or an -O-monoglycoside or -diglycoside sugar group, such as an -O-glycosyl group, preferably a glycosyl group or an -O-glycosyl group, iv) a (C1-C6)alkyl group, v) a (C1-C6)alkoxy group, n and m representing, independently of each other, an integer of between 1 and 3, said compound preferably being chosen from luteolin, quercetin, myricetin, rutin, α-glycosylrutin and their mixtures. 4. Composition according to any one of the preceding claims, said compound of formula (I) or (I') being chosen from natural compounds or compounds of natural origin. 5. Composition according to any one of the preceding claims, comprising from 0.01% to 5.0% by weight of compound(s) of formula (I), in particular from 0.03% to 2.0% by weight, preferably from 0.05% to 1.0% by weight, more preferentially from 0.05% to 0.2% by weight, with respect to the total weight of said composition. 6. Composition according to any one of the preceding claims, said water- soluble colorant being chosen from water-soluble colorants which are natural or of natural origin. 7. Composition according to any one of the preceding claims, said colorant being chosen from: - pyran or pyranium dyes, in particular anthocyans and anthocyanosides, preferably extracts of red radish or extracts of sweet potato, in particular purple sweet potato; - polyene dyes in particular chosen from jasminoids, especially those, the coloured active principles of which have the following formula:
Figure imgf000059_0001
in which: R11 and R16, which are identical or different, represent: i) a cycloalkyl group which is optionally unsaturated and/or optionally substituted by one or more groups chosen from a) oxo, b) hydroxyl and c) (C1-C6)alkyl, preferably (C1-C4)alkyl, in particular methyl; ii) a cycloalkylcarbonyl group, the cycloalkyl group of which is optionally unsaturated and/or optionally substituted by one or more groups a) to c) as defined above; iii) -C(O)-O-R17 with R17 representing a hydrogen atom or a (C1-C6)alkyl, preferably (C1-C4)alkyl, group, in particular a methyl group; iv) sugar, in particular glycosyl or glycosyloxy; or v) sugar-C(O)-; and R12 to R15, which are identical or different, preferably identical, represent a hydrogen atom or a (C1-C6)alkyl group; preferably, R12 to R15 represent a (C1-C4)alkyl group, for example a methyl group; and also its geometrical isomers, its salts of organic or inorganic bases and its solvates, such as its hydrates; and - curcumin, the coloured active principles of which have the following formula:
Figure imgf000060_0001
in which R7, R8, R9 and R10 represent, independently of one another, a hydrogen atom, a hydroxyl group or a (C1-C6)alkoxy, preferably (C1-C4)alkoxy, group, in particular a methoxy group, it being understood that at least one of the R7 to R10 groups represents a hydroxyl group; preferably, R8 and R10 represent a hydroxyl group, R7 represents a hydrogen atom or a (C1-C4)alkoxy group, in particular a methoxy group, and R9 represents a hydrogen atom or a (C1-C4)alkoxy group, in particular a methoxy group, and also its geometrical isomers, its salts of organic or inorganic bases and its solvates, such as its hydrates. 8. Composition according to any one of the preceding claims, said colorant being chosen from organic pigments, in particular chosen from carbon black, pigments of D & C type and lakes based on cochineal carmine of barium, strontium, calcium and aluminium, preferably pigments of D&C type, more preferentially chosen from synthetic or natural water-soluble dyes, such as, for example, FDC Red 4, DC Red 6, DC Red 22, DC Red 28, DC Red 30, DC Red 33, DC Orange 4, DC Yellow 5, DC Yellow 6, DC Yellow 8, FDC Green 3, DC Green 5, FDC Blue 1 and also their mixtures, more preferentially still chosen from FDC Red 4, DC Red 33, DC Orange 4, DC Yellow 5, DC Green 3, DC Green 5, FDC Blue 1 and also their mixtures. 9. Composition according to any one of the preceding claims, comprising from 0.0001% to 20% by weight of the water-soluble colorant(s), with respect to the total weight of the composition containing the colorant(s) or the extract(s) containing them, preferably: - when the water-soluble colorant(s) is (are) pure, the content in the fragrancing composition varies from 0.0001% to 5% by weight, preferably from 0.001% to 3.0% by weight, more preferentially from 0.01% to 1.0% by weight and more preferentially still from 0.1% to 0.5% by weight of the water-soluble colorant(s), with respect to the total weight of said composition; - when the water-soluble colorant(s) is (are) in the form of extract(s), the content of extract(s) in the composition varies from 0.01% to 20% by weight, particularly from 0.1% to 10% by weight, particularly from 0.2% to 8.0% by weight, preferentially from 0.3% to
3.0% by weight and more preferentially from 0.4% to 2.0% by weight, better still from 0.5% to 1% by weight, of extract(s) in said composition, with respect to the total weight of said composition.
10. Composition according to any one of the preceding claims, said fragrancing substance being chosen from essential oils, fragrances and aromas of synthetic or natural origin, and their mixtures.
11. Composition according to any one of the preceding claims, comprising from 0.0001% to 10% by weight of fragrancing substance(s), particularly from 0.001% to 8.0% by weight, more particularly from 0.01% to 5.0% by weight and preferentially from 0.1% to 1.0% by weight, with respect to the total weight of said composition.
12. Composition according to any one of the preceding claims, the content of (bio)ethanol varying from 16% to 99.5% by weight, in particular from 25% to 97% by weight, more particularly from 35% to 95% by weight, more particularly still from 45% to 90% by weight, with respect to the total weight of the composition.
13. Composition according to any one of the preceding claims, which is provided in the form of an eau fraiche, an eau de toilette, an eau de parfum, an aftershave lotion, an eau de soin, a silicone or hydrosilicone care oil, a fragranced two-phase lotion, a body milk or a shampoo.
14. Use of a compound of formula (I) as defined according to any one of Claims 1 to 4 as stabilizer in a fragranced composition, in particular a cosmetic composition, additionally comprising ethanol in a content strictly greater than 15% by weight, with respect to the total weight of the composition, and also at least one water-soluble colorant and at least one fragrancing substance.
15. Method for the cosmetic treatment of keratin materials, in particular of the skin, or of clothing, comprising at least one stage of application, to said keratin materials and/or said clothing, of a fragranced composition as defined according to any one of Claims 1 to 13.
PCT/EP2023/069984 2022-07-19 2023-07-19 Fragranced cosmetic composition comprising at least one flavonoid compound, ethanol, a water-soluble colorant and a fragrancing substance WO2024017930A1 (en)

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