Perfumed cosmetic composition comprising at least one flavonoid compound, ethanol, a water-soluble coloring matter and a perfuming matter
Flavonoid compounds stabilize perfumed cosmetic compositions with high ethanol content, addressing color and odor instability issues while maintaining environmental sustainability.
Patent Information
- Application Number
- FR2022007386
- Authority / Receiving Office
- FR · FR
- Patent Type
- Patents
- Current Assignee / Owner
- Filing Date
- 2022-07-19
- Publication Date
- 2025-07-18
- Estimated Expiration
- 2042-07-19
AI Technical Summary
Existing perfumed cosmetic compositions with high ethanol content face challenges in stabilizing water-soluble colorants due to factors like oxidation, thermal reactions, and photochemical degradation, leading to color instability and unpleasant odors from synthetic stabilizers, which are not environmentally friendly.
Incorporating flavonoid compounds, such as luteolin, quercetin, and rutin, in combination with ethanol and water-soluble coloring matters, stabilizes the perfumed compositions by preserving color and odor over time, even under high ethanol conditions.
The combination effectively stabilizes the color and scent of perfumed compositions, ensuring long-term stability and environmental friendliness by using natural ingredients, reducing staining on clothing.
Abstract
Description
Title of the invention: Perfumed cosmetic composition comprising at least one flavonoid compound, ethanol, a water-soluble coloring matter and a perfuming matter Technical field
[0001] The present invention aims to propose a new perfumed cosmetic composition, for the field of perfuming keratin materials and / or clothing, but also for the care or cosmetic treatment of keratin materials.
[0002] Generally speaking, the formulation of environmentally friendly cosmetic products is becoming an important issue in order to satisfy a new consumer expectation, in particular that of natural and / or eco-designed products, i.e. products whose design and development take into account environmental impacts.
[0003] It is thus common to seek to replace synthetic compounds present in cosmetic compositions with natural and / or naturally derived ingredients.
[0004] These environmental issues concern all cosmetic products, particularly perfumed compositions.
[0005] It is known that a perfume is the result of a combination of different odorous substances, each providing a specific diffusing odor or "note" and evaporating respectively at different periods. More precisely, each perfume has what is called a "top note" which is the odor diffusing first when the perfume is applied or when the container containing it is opened, a "heart or body note" which corresponds to the complete perfume (emission for a few hours after the "top note") and a "base note" which is the most persistent odor (emission for several hours after the "heart note"). The persistence of the base note corresponds to the remanence of the perfume.
[0006] Human beings have always sought to perfume themselves and the objects around them or the places in which they find themselves, both to mask strong and / or unpleasant odors and to give a good smell.
[0007] It is common to incorporate perfume into a number of products or compositions, in particular cosmetic and dermatological products, such as fresh waters, toilet waters, perfume waters, perfume elixirs or extracts, aftershave lotions, treatment waters or even biphasic lotions.
[0008] In the preparation of perfume compositions, such as perfumes or eaux de toilette, the use of ethanol as a solvent is very widespread. Ethanol allows to properly solubilize the perfume ingredients used by the perfumer. It is a very good solvent that evaporates quickly, thus providing a sensation of freshness. Ethanol also has the advantage of being inexpensive and allowing the formulation of transparent compositions.
[0009] For such reasons, the majority of perfume compositions contain ethanol, generally present in high levels, typically in levels greater than 15% by weight of the total weight of these compositions.
[0010] For aesthetic and manufacturing cost reasons, perfumes are colored by adding an effective quantity of coloring matter to the formulation support (generally alcoholic or hydroalcoholic) rather than dyeing or lacquering the bottle, which is a more expensive industrial operation.
[0011] As coloring materials, mention may be made more particularly of water-soluble dyes, in particular natural or of natural origin, which, in a diluted form in aqueous media, provide the most intense chromatic coloring and as such are particularly interesting for the field of cosmetics.
[0012] Unfortunately, the use of colorants in the aqueous solute state poses difficulties, particularly in terms of color stability, with regard to perfumed compositions intended to incorporate them, in particular when the ethanol content is high, namely greater than 15% by weight.
[0013] In addition, mention should also be made of the classic degradations for water-soluble dyes, in particular due to the oxidation of oxygen in the air, thermal and photochemical reactions, in particular during prolonged storage, which can further alter the coloring of the composition.
[0014] Thus, it is of great interest to be able to stabilize the color developed in perfumed cosmetic formulations, and in particular in an alcoholic or hydroalcoholic medium, from water-soluble colorants, in particular natural or of natural origin, and this both over time, and when exposed to light and / or temperature and / or oxygen in the air. In addition, it is necessary to prevent the scent of the perfume products from evolving over time, whether in the presence of heat and / or light or not. Prior art
[0015] In order to ensure the stability of perfumed formulations, it has already been proposed to incorporate a filtering system and / or an antioxidant system.
[0016] Thus, a certain number of documents in the field of cosmetics, in particular EP 1 897 592 and WO 2005 / 042828 propose perfumed compositions, including in particular colorants, comprising combinations of UV filters as stabilizers, in particular of the [3,[3'-alkyl diphenylacrylate or a- cyano-[3,[3'-alkyl diphenylacrylate, such as octocrylene, dibenzoylmethane derivatives, cinnamates or camphor derivatives and triazines.
[0017] However, certain filters such as [3,[3'-alkyl diphenylacrylate or a-cyano-[3,[3'-alkyl diphenylacrylate compounds, such as octocrylene, are not always satisfactory for stabilizing the colors while preserving the smell of the perfumes.
[0018] Indeed, some filters may have an unpleasant odor left in the formula. Synthetic filters, such as ethylhexylmethoxycinnamate, are also not satisfactory for stabilizing the coloring materials of perfume solution. In particular, they prove to be less effective in terms of preserving the intensity of the color and / or the chromaticity of the colored solution in the light and / or over time.
[0019] Furthermore, the piperidinol derivatives used in some of these compositions have the disadvantage of generating yellowing of the toilet waters as well as a parasitic odor with a “chemical” connotation.
[0020] Also, certain particular benzotriazole and / or triazine compounds have already been described for stabilizing cosmetic compositions, such as eau de toilette. Combinations of these benzotriazole compounds with other particular sunscreens have also been defined for the purpose of stabilizing perfumes. However, these benzotriazole compounds, in particular Bumetrizole, are poorly soluble in eau de toilette, tend to recrystallize over time, in addition to having a low stabilizing power.
[0021] In addition to the potential problems mentioned above linked to their presence, generally speaking, the sunscreens proposed to date, such as ethylhexylmethoxycinnamate, are synthetic.
[0022] However, as mentioned previously, more and more users are looking for colored perfume compositions that are said to be “less chemical” and more environmentally friendly. They may perceive synthetic compounds in a negative way, in particular as compounds that are harmful to their health and to the environment. Thus, colored perfume compositions comprising synthetic sunscreens are not entirely satisfactory for consumers who prefer natural or naturally derived compounds to synthetic compounds.
[0023] What is more, these colored perfume compositions generally do not respect the principles of green chemistry.
[0024] It is therefore of great interest to find a way to stabilize the color of perfume compositions comprising a high ethanol content, if possible with natural products or those of natural origin.
[0025] Furthermore, it has already been sought to specifically stabilize natural dyes. or of natural origin water-soluble in cosmetic or food compositions.
[0026] In this respect, document WO 2017 / 162599 describes the stabilization of natural or naturally occurring water-soluble colorants using polymeric surfactants or specific fillers. Also, document WO 2009 / 031051 proposes stabilizing anthocyanin extracts with a stabilizing compound comprising a thiol group, in the field of food compositions.
[0027] However, these documents do not in any way concern the formulation of perfume compositions, even less those comprising a high ethanol content. Statement of the invention
[0028] There therefore remains a need to research new colored perfumed formulations, in particular alcoholic or hydroalcoholic ones, which remain stable over time and under the effects of light.
[0029] In particular, there remains a need to have colored perfumed cosmetic compositions, the evolution of the organoleptic properties of which, namely the odor and / or the color, in particular at least the color, is controlled over time, and this if possible by means of compounds which respect at least one of the twelve principles of green chemistry.
[0030] Furthermore, there is a need for such compositions whose formulation complies with at least one of the twelve principles of green chemistry, in particular comprising ingredients derived from green chemistry.
[0031] Finally, there remains a need to offer colored perfumed cosmetic compositions leaving few, if any, traces, particularly on clothing, during their use.
[0032] The present invention aims precisely to meet these needs. Summary of the invention
[0033] Thus, according to a first of its aspects, the present invention relates to a perfumed composition, in particular a cosmetic composition, comprising: (a) at least one compound corresponding to formula (I), or one of its geometric isomers, in particular optical isomers, of its tautomers, as well as its salts of organic or mineral acid or base, or of its solvates, in particular hydrates:
[0034] [Chem.l] O (J)
[0035] formula (I) in which: ZZZ2 represents a double bond or a single bond, R1 represents an atom or a group chosen from: - a hydrogen atom, - a hydroxyl, - a (Ci-C6)alkyl group, - a (Ci-C6)alkoxy group, - a mono- or di-saccharide sugar group, such as glycosylated, or a -O-mono- or di-saccharide sugar group, such as -O-glycosyl; R2 represents a hydrogen atom, a (Ci-C6)alkyl group or a mono-osidic or di-osidic sugar group, such as glycosylated, R3 represents a hydrogen atom or a (Ci-C6)alkyl group, n represents an integer between 1 and 3 and m represents an integer between 0 and 3; it being understood that: when m represents an integer greater than or equal to 2, the radicals R2 may be identical or different, and when n represents an integer greater than or equal to 2, the radicals R3 may be identical or different; b) ethanol in a content strictly greater than 15% by weight, relative to the total weight of the composition; (c) at least one water-soluble coloring matter; and (d) at least one fragrance substance.
[0036] The inventors have found, surprisingly, that the combination of a compound of formula (I) as defined above, within a perfumed composition comprising a high ethanol content, with at least one perfume substance and at least one water-soluble coloring matter, allows effective stabilization of said composition, in particular of its color.
[0037] Indeed, as is clear from the examples below, the composition according to the invention is stable, in the sense that the evolution of the color of the composition remains low over time, even under conditions simulating accelerated aging of the composition, in particular in a hydroalcoholic medium with a high ethanol content, and in light.
[0038] Thus, the invention also relates, according to another of its aspects, to the use of a compound of formula (I), as a stabilizer in a perfumed composition, in particular a cosmetic composition, further comprising ethanol in a content strictly greater than 15% by weight, relative to the total weight of the composition, as well as at least one water-soluble coloring matter and at least one perfuming substance.
[0039] Certain compounds corresponding to formula (I) have already been proposed in order to stabilize the color in food compositions, in particular in application US 2004 / 091589 A1 or 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.
[0040] However, these documents do not in any way concern perfumed compositions, even less containing more than 15% by weight of ethanol, whereas such specific compositions are precisely the cause of increased destabilization of the water-soluble colorants incorporated therein.
[0041] A composition according to the invention is intended in particular for the cosmetic treatment of keratin materials.
[0042] Thus, the invention relates, according to yet another of these aspects, to a method for the cosmetic treatment of keratin materials, in particular of the skin, comprising at least one step of applying to said keratin materials a composition according to the invention.
[0043] The invention also relates to a method for the cosmetic treatment of keratin materials, in particular the skin, or a garment, comprising at least one step of applying to said keratin materials and / or said garment, a perfumed composition according to the invention.
[0044] It is understood that the cosmetic treatment methods referred to in the present application are non-therapeutic.
[0045] A composition according to the invention is intended in particular to be used in order to perfume keratin materials and / or clothing.
[0046] Thus, the invention also relates, according to another of its aspects, to a method for perfuming keratin materials, and in particular the skin, and / or a garment, comprising the application to said keratin materials and / or said garment of the composition as defined above.
[0047] Advantageously, the content of water-soluble coloring matter(s) in the perfumed colored composition may be less than or equal to 300 ppm.
[0048] Indeed, the inventors have found that, thanks to the claimed combination, even a low content of water-soluble coloring matter(s) makes it possible to achieve a satisfactory chromatic intensity, while reducing the risks of stains forming on clothing during its application, compared to compositions comprising higher contents of coloring matter(s).
[0049] In the context of the present invention, and unless otherwise indicated, the following definitions apply:
[0050] By “perfumed composition” or “perfuming composition” within the meaning of the present invention, is meant any composition which leaves a perfume after application to keratin materials.
[0051] By "keratin materials" within the meaning of the present invention, is meant in particular the skin, the lips, the hair, the scalp, the eyelashes and eyebrows or even the nails, in particular the skin and / or the lips, and preferably the skin.
[0052] By "coloring matter" is meant any compound capable of coloring the perfumed composition, that is to say which absorbs in the visible spectrum, in particular so as to appear to the human eye in a color such as yellow, orange, red, violet, blue or green, in particular orange, red, violet or blue.
[0053] In other words, a perfumed composition according to the invention is said to be “colored”. By “colored” composition is meant a composition which appears to the human eye as a color in the visible spectrum, that is to say which to the eye is distinct from white or colorless, namely which absorbs in the range of yellow, orange, red, purple, violet, blue and green. Such a composition may be opaque or clear, preferably clear.
[0054] By "clear" in the sense of the present invention, it is meant that the composition is transparent, that is to say that it lets light pass through and the objects behind it appear clearly.
[0055] By "water-soluble" in the sense of the present invention is meant that the coloring matter, generally organic, natural or synthetic, is soluble in an aqueous phase or water-miscible solvents.
[0056] A perfumed colored composition may be in any form suitable for its application to keratin materials and / or clothing. It may in particular be in liquid or solid form, for example in powder form.
[0057] By "powder" is meant a composition in powder form, preferably essentially free of dust. In other words, the particle size distribution is such that the weight ratio of particles which have a size less than or equal to 50 micrometers (dust ratio) preferably less than or equal to 10 micrometers (dust ratio) is advantageously less than or equal to 5%, preferably less than 2% and more particularly less than 1% (particle size evaluated using a RETSCH AS 200 DIGIT particle size analyzer; Oscillation height: 1.25 mm / sieving time: 5 minutes). Advantageously, the particle size is between 10 pm and 500 pm. The “powder” of solid material(s) can be sieved to obtain particles of upper limit sizes corresponding to the orifices or mesh sizes of the sieve, particularly between 35 and 80 mesh (US). According to a particular embodiment of the invention, the particle size of the powder of solid natural material(s) is fine. According to the invention, a particle size of less than or equal to 900 pm is more particularly understood. Preferably, the powder consists of fine particles of size between 7 pm and 700 pm and better still between 100 nm and 500 pm.
[0058] For the purposes of the present invention, the term “perfuming substance” is understood to mean any perfume, any odorous raw material or aroma capable of releasing a pleasant odor, in particular as defined in the remainder of the text. “Perfuming”, “odorous” or “odoriferous” substances are synonymous for the purposes of the present invention.
[0059] A composition according to the invention is generally suitable for application to keratin materials, in particular topical application to the skin, and therefore generally comprises a physiologically acceptable medium, i.e. compatible with the skin.
[0060] It is preferably a cosmetically acceptable medium, that is to say which has a pleasant color, odor and feel and does not generate unacceptable discomfort, that is to say tingling, tightness, redness, likely to discourage the user from applying this composition.
[0061] For the purposes of the present invention, a “stabilizer” is intended to designate a compound capable of stabilizing the perfumed composition comprising it, in particular in terms of preserving its organoleptic properties against external aggressions, in particular light or temperature differences, in particular the color and / or the odor of said composition, and even more particularly the color of said composition.
[0062] A (Cx-Cz)alkyl group represents a linear or branched hydrocarbon chain comprising from x to z carbon atoms. For example, a (Ci-C6)alkyl group represents a linear or branched hydrocarbon chain comprising from 1 to 6 carbon atoms.
[0063] A (Cx-Cz)alkoxy group represents a radical -O-(CX-Cz)alkyl, in which the (Cx-Cz)alkyl group is as defined previously.
[0064] A “sugar” radical is understood to denote a monosaccharide, oligosaccharide or polysaccharide radical, in particular consisting of 1 to 5 saccharide units, more particularly 2 to 3, and preferably 2 saccharide units, linked by a covalent bond with the compound carrying the group. Examples of sugar radicals include sucrose (or saccharose), glucose, galactose, ribose, fucose, maltose, fructose, mannose, arabinose, xylose, lactose.
[0065] By "glycosylated" group is meant 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 bearing the group.
[0066] Preferably, the compound of formula (I) is chosen from natural compounds or compounds of natural origin.
[0067] By "natural" in the sense of the present invention, it is meant that the coloring matter is obtained directly from the earth or soil, or from plants or animals, via, where appropriate, one or more physical processes, such as for example grinding, refining, distillation, purification or filtration, or else from a biotechnological process, in particular from cell or microbiological cultures, for example of fungi or bacteria. So-called "natural" dyes or pigments include compounds which are present in nature and which can be reproduced by chemical (semi)synthesis.
[0068] By "of natural origin" within the meaning of the present invention, it is meant that the coloring matter is obtained from a natural substance having undergone one or more additional chemical or industrial treatments, resulting in modifications not affecting the essential qualities of this substance. As a non-limiting example of additional chemical or industrial treatment resulting in modifications not affecting the essential qualities of a natural compound, mention may be made of those authorized by control organizations such as Ecocert (Reference for organic and ecological cosmetic products, January 2003) or defined in recognized manuals in the field, such as "Cosmetics and Toiletries Magazine", 2005, vol. 120, 9:10.
[0069] According to the invention, a compound is considered to be natural or of natural origin when it is mainly composed of natural constituents, that is to say when the weight ratio of the natural constituents to the non-natural constituents which compose it is greater than 1.
[0070] Advantageously, the compound of formula (I) is a so-called “green” compound, namely that it complies with at least one of the twelve principles of green chemistry.
[0071] For the purposes of the present invention, the term "geometric isomer" is intended to denote any molecule of constitution identical to formula (I) defined above but whose spatial organization of atoms is different. In particular, it may be conformational stereoisomers, i.e. compounds differing by rotation around a single bond, or configurational stereoisomers, in particular enantiomers or diastereoisomers (or optical isomers), or even isomers of constitution, that is to say compounds differing by the sequence of atoms, in particular tautomers in the case of tautomerism equilibrium.
[0072] For the purposes of the present invention, the term "organic or mineral acid or base salt" is intended 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 adding an organic or mineral base or acid, in particular a cosmetically acceptable one, to the compound of formula (I). Examples of mineral bases that may be cited are hydroxides or carbonates of alkali metal, alkaline earth metal, such as sodium, potassium, calcium, ammonium, magnesium, lithium or sodium. Examples of organic bases that may be cited are amines or alkanolamines. Examples of acids include hydrochloric acid, hydrobromic acid, sulfuric acid, alkylsulfonic acids, arylsulfonic acids, citric acid, succinic acid, tartaric acid, lactic acid, alkoxysulfinic acids, aryloxysulfinic acids, phosphoric acid, acetic acid..
[0073] For the purposes of the present invention, the term "solvated" is intended to denote the form of the compound of formula (I) when the latter is associated with a solvent. Solvates include conventional solvates formed during the process for preparing the compound of formula (I). Examples of solvates are those obtained in the presence of water or a linear or branched alcohol, in particular ethanol or isopropanol.
[0074] For the purposes of the present invention, the term “flavone” means any compound comprising a 2-phenylchromen-4-one (2-phenyl-1-benzopyran-4-one) structural skeleton corresponding to the following formula:
[0075] [Chem.2]
[0076] For the purposes of the present invention, the term “flavonol” is understood to mean any compound comprising a flavone skeleton as defined above and substituted by a hydroxyl group in position 3, namely a skeleton corresponding to the following formula:
[0077] [Chem.3] O
[0078] For the purposes of the present invention, the term "flavanone" is intended to denote any compound comprising a flavone skeleton as defined above but not comprising unsaturation in the 2,3 position, namely a skeleton corresponding to the following formula:
[0079] [Chem.4]
[0080] The expression “at least one” is equivalent to “one or more”.
[0081] The expression “inclusive” for a range of concentrations means that the range limits are part of the defined interval.
[0082] The expressions “between ... and ...”, “includes from ... to ...”, “formed from ... to ...”, and “ranging from ... to ...” must be understood inclusively, unless otherwise specified.
[0083] Other characteristics, variants and advantages of the compositions according to the invention will become more apparent on reading the description and examples which follow. Detailed description Compounds of formula (I)
[0084] As mentioned previously, a perfumed composition according to the invention comprises at least one compound of formula (I), or one of its geometric isomers, in particular optical isomers, of its tautomers, as well as its salts of organic or mineral acid or base, or its solvates, in particular the hydrates:
[0085] [Chem.5]
[0086] formula (I) in which: represents a double bond or a single bond, R1 represents an atom or a group chosen from: - a hydrogen atom, - a hydroxyl, - a (Ci-C6)alkyl group, - a (Ci-C6)alkoxy group, - a mono- or di-saccharide sugar group, such as glycosylated, or a -O-mono- or di-saccharide sugar group, such as -O-glycosyl; R2 represents a hydrogen atom, a (Ci-C6)alkyl group, or a mono- or di-osidic sugar group, such as glycosylated, R3 represents a hydrogen atom or a (Ci-C6)alkyl group, n represents an integer between 1 and 3 and m represents an integer between 0 and 3, provided that: when m represents an integer greater than or equal to 2, the radicals R2 may be identical or different, and when n represents an integer greater than or equal to 2, the radicals R3 can be identical or different.
[0087] In formula (I) defined above, it is further understood that the -OR2 group(s) are carried by any one of the carbon atoms in position 5 to 8 of the flavone, flavonol or flavanone skeleton and that the -OR3 group(s) are carried by any one of the carbon atoms in position 2' to 6' of the flavone, flavonol or flavanone skeleton.
[0088] Preferably, the -OR2 group(s) are carried by any one of the carbon atoms in position 5 and / or 7.
[0089] Advantageously, in formula (I), m is 2 and the two -OR2 groups are carried respectively by the carbon atoms in positions 5 and 7.
[0090] According to one embodiment, the -OR3 group(s) are carried by any one of the carbon atoms in position 3', 4' and / or 5'.
[0091] Advantageously, in formula (I), n is 2 and the two -OR3 groups are carried respectively by the carbon atoms in the 3' and 4' positions, or n is 3 and the three -OR3 groups are carried respectively by the carbon atoms in the 3', 4' and 5' positions.
[0092] Advantageously, in formula (I), R1 represents an atom or a group chosen from: i) hydrogen, ii) a hydroxyl, and iii) a glycosylated or -O-glycosyl group.
[0093] Advantageously, in formula (I), each R2 independently represents a hydrogen atom or a glycosylated group, preferably a hydrogen atom.
[0094] Advantageously, in formula (I), each R3 independently represents a hydrogen atom or a methyl, preferably a hydrogen atom.
[0095] Advantageously, in formula (I), n and m, identical or different, independently represent an integer ranging from 1 to 3.
[0096] The compounds corresponding to formula (I) generically belong to the family of flavonoids, more precisely to the families of flavones, flavonols and flavanones.
[0097] Preferably, a composition according to the invention comprises a compound of formula (I) chosen from luteolin, quercetin, myricetin, rutin, hesperidin, na-rirutin, alpha-glycosyl rutin, quercitrin, isoquercitrin, morin, hesperetin, chrysin, apigenin, luteolin-7-O-glucoside, 6-hydroxyflavone, 7,8-dihydroxyflavone or tropoflavin, and mixtures thereof.
[0098] According to a particularly preferred embodiment, the compound of formula (I) is of formula (!') below, or one of its geometric isomers, of its tautomers, as well as its salts of organic or mineral acid or base, or its solvates, in particular the hydrates:
[0099] [Chem.6]
[0100] formula (!') in which: R represents an atom or group chosen from: i) a hydrogen atom, ii) a hydroxyl, iii) a mono- or di-saccharide sugar group, such as glycosylated, or a -O-mono- or di-saccharide sugar group, such as -O-glycosyl, preferably a glycosylated group or an -O-glycosyl group; iv) a (Ci-C6)alkyl group, and v) a (Ci-C6)alkoxy group, n and m represent, independently of one another, an integer between 1 and 3, preferably equal to 1 or 2.
[0101] In particular, the -OH groups are carried by any of the carbon atoms in position 5 and / or 7 and 3', 4' and / or 5'.
[0102] Advantageously, in the formula (!), m is 2 and the two -OH groups are carried respectively by the carbon atoms in positions 5 and 7.
[0103] According to one embodiment, the -OH group(s) are carried by any one of the carbon atoms in position 3', 4' and / or 5'.
[0104] Advantageously, in the formula (!), n is 2 and the two -OH groups are carried respectively by the carbon atoms in the 3' and 4' positions, or n is 3 and the three -OH groups are carried respectively by the carbon atoms in the 3', 4' and 5' positions.
[0105] The compounds of formula (I) and (!') in accordance with the invention are preferably chosen from natural compounds or compounds of natural origin.
[0106] They are preferably “green” compounds.
[0107] Preferably, a composition according to the invention comprises a compound of formula (I) or (!') chosen from luteolin, quercetin, myricetin, rutin, alpha-glycosyl rutin, and mixtures thereof, even more preferably chosen from rutin, alpha-glycosyl rutin, and mixtures thereof.
[0108] According to one embodiment, the compound of formula (I) is rutin.
[0109] According to another embodiment, the compound of formula (I) is alpha-glycosyl rutin.
[0110] The compounds of formula (I) or (!) can be found in many plant extracts, in particular grapes, berries, nuts, citrus peel, capers, olives, buckwheat, asparagus, raspberry, blackcurrant, plum, mango, green beans, rhubarb, blueberry, onion, quince, apple, cherry, broccoli, green or black tea leaves, as well as plants such as plants of the genus Citrus, Sophora Japonica, Eucalyptus macrorrhyncha, wild pansy, white mulberry, parsley, Ginkgo biloba, lovage, elderberry, Vitis vinifera.
[0111] The compounds of formulas (I) and (!') can be obtained by any method known to those skilled in the art, for example by extraction from a plant extract.
[0112] The compounds of formulas (I) or (!) defined above may optionally be introduced into a perfumed composition according to the invention in the form of an extract plant. For example, rutin can be implemented in the form of a bud extract of the Sophora Japonica plant.
[0113] A number of compounds of formula (I) or (!) are also commercially available, such as alpha-glycosyl rutin marketed by the company Qingdao Taitong Pharmaceutical.
[0114] A perfumed composition according to the invention may 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 preferably from 0.05% to 0.2% by weight, relative to the total weight of said composition.
[0115] Advantageously, the content of compound(s) of formula (I) is less than or equal to 0.1% by weight, relative to the total weight of the composition. Thus, a perfumed composition according to the invention may 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, relative to the total weight of said composition.
[0116] As mentioned above, the compound of formula (I) can be implemented in the form of a plant extract also called “raw raw material”, comprising one or more compounds of formula (I) as defined above. Thus, a perfumed 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), relative to the total weight of said composition.
[0117] In particular, said plant extract(s) are rich in compound(s) of formula (I), namely they may comprise a content of compound(s) of formula (I) ranging from 80% to 99% by weight, in particular from 85% to 95% by weight, relative to their total weight. Ethanol
[0118] As mentioned previously, a perfumed composition according to the invention comprises ethanol, in a content strictly greater than 15% by weight, relative to the total weight of the composition.
[0119] As already mentioned above, ethanol is commonly used in the field of perfume compositions as a solvent.
[0120] In particular, the ethanol may 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, relative to its total weight.
[0121] Alternatively, the ethanol may be 95 proof ethanol.
[0122] Advantageously, the ethanol is of natural origin, in particular of plant origin, namely that it is produced from biomass. Ethanol of natural origin is called “bioethanol”.
[0123] Advantageously, a composition according to the invention may comprise a (bio)ethanol content varying from 16% to 99.5% by weight, in particular from 25% to 97% by weight, more particularly from 35% to 95% by weight, even more particularly from 45% to 90% by weight, relative to the total weight of the composition.
[0124] In particular, a composition according to the invention may comprise a (bio)ethanol content ranging from 65% to 80% by weight, for example 68%, 70% or 78% by weight, relative to the total weight of the composition. Water-soluble coloring matter
[0125] As mentioned previously, a perfumed composition according to the invention comprises at least one water-soluble coloring matter, also called “water-soluble coloring”.
[0126] As mentioned previously, a coloring matter is capable of coloring the perfumed composition by absorbing in the visible spectrum.
[0127] As visual color and absorption wavelength associated with said color, the following colors may be cited: "yellow" = Xmax greater than 400 nm up to and including 440 nm, "orange" = Xmax greater than 440 nm up to and including 490 nm, "red" = Xmax greater than 490 to up to and including 520 nm, "purple" = Xmax greater than 520 nm and 560 nm, "violet" = Xmax greater than 560 nm to 580 nm, "blue" = Xmax greater than 580 nm up to and including 620 nm, "blue-green" = Xmax greater than 620 nm up to and including 650 nm, and "green" = Xmax greater than 650 nm up to and including 780 nm.
[0128] Advantageously, the water-soluble coloring matter suitable for the invention is capable of coloring the perfumed composition by absorption of the following colors: “orange” = Xmax greater than 440 nm up to and including 490 nm, “red” = Xmax greater than 490 to up to and including 520 nm, “purple” = Xmax greater than 520 nm and 560 nm, “violet” = Xmax greater than 560 nm to 580 nm, and “blue” = Xmax greater than 580 nm up to and including 620 nm.
[0129] Preferably, the water-soluble coloring matter is distinct from the compound of formula (I) as defined above.
[0130] In particular, a dye is water-soluble when its solubility in water, measured at 25°C, is at least equal to 0.01 g / L.
[0131] Preferably, the water-soluble coloring matter is chosen from natural or naturally occurring water-soluble coloring matters.
[0132] According to a particular embodiment, the water-soluble dyes suitable for the invention are derived from extracts of animals, bacteria, fungi, algae, plants used in their entirety or in part.
[0133] The water-soluble colorant(s) suitable for the invention are preferably derived from plant extracts or parts of plants such as fruits including citrus fruits, vegetables, trees, shrubs. Mixtures of these extracts can also be used.
[0134] Thus, the water-soluble coloring matter can be introduced into a perfumed composition according to the invention in the form of a natural extract.
[0135] Such extracts can be obtained by extraction from various parts of plants such as for example the root, wood, bark, leaf, flower, fruit, seed, pod or peel.
[0136] Among the plant extracts, we can cite extracts of rose leaves, gardenias, Clitoria ternatea or blue pea flower, turmeric rhizomes or carrot, sweet potato or radish peels.
[0137] Among the fruit extracts, mention may be made of apple extracts, grape extracts, or extracts of cocoa beans and / or pods.
[0138] Among the vegetable extracts, mention may be made of potato, onion peel and beetroot extracts.
[0139] Among the tree wood extracts, we can cite pine bark extracts, logwood extracts.
[0140] Mixtures of plant extracts can also be used.
[0141] As an example of water-soluble coloring materials more particularly suitable for the invention, mention may be made of natural or naturally derived water-soluble dyes, in particular dyes derived from natural orthodiphenol.
[0142] More particularly, the orthodiphenols 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 anthocyanins, in particular myrtillin or anthocyanosides; - orthohydroxybenzoates, for example gallic acid salts; - hydroxystilbenes, for example tetrahydroxy-3,3',4,5'-stilbene, possibly oxylated (for example glycosylated); - 3,4-dihydroxyphenylalanine and its derivatives; - 2,3-dihydroxyphenylalanine and its derivatives; - 4,5-dihydroxyphenylalanine and its derivatives; - dihydroxycinnamates; - orthopolyhydroxycoumarins; - orthopolyhydroxyisocoumarins; - orthopolyhydroxy-coumarones; - orthopolyhydroxyisocoumarones; - orthopolyhydroxychalcones; - orthopolyhydroxychromones; - quinones; - hydroxyxanthones; - 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 A1, A2, B1, B2, B3 and C1; - proanthocyanins; - tannic acid; - gallic acid; - ellagic acid; - neoflavanoles and neoflavanones, in particular derivatives of hematoxylin, hematein, brazilin and brazilein; and - mixtures of the preceding compounds.
[0143] Preferably, the orthodiphenols which can be used according to the invention are chosen from anthocyanidins, in particular cyanidin, Delphinidin, and Petunidin; anthocyanins or anthocyanins, in particular myrtillin; proanthocyanidins and in particular proanthocyanidins A1, A2, B1, B2, B3 and C1; proanthocyanins; and mixtures of the preceding compounds.
[0144] As examples of water-soluble coloring materials more particularly suitable for the invention, mention may be made of those chosen from: - pyran or pyranium colorants, in particular anthocyanins and anthocyanosides, preferably red radish extracts, sweet potato extracts, in particular purple sweet potatoes; and - polyene dyes chosen in particular from jasminoids, in particular those whose colored active ingredients have the following formula:
[0145] [Chem.7]
[0146] in which: R11 and R16, 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) (Ci-C6)alkyl, of preferably (Ci-C4)alkyl, in particular methyl; ii) a cycloalkylcarbonyl group in which the cycloalkyl group 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 (Ci-C6)alkyl group, preferably (Ci-C4)alkyl, in particular methyl; iv) sugar, in particular glycosylated, glycosyloxy; or v) sugar-C(O)-, and R12 to R15, identical or different, preferably identical, represent a hydrogen atom or a (Ci-C6)alkyl group, preferably R12 to R15 represent a (CrC4)alkyl group, for example methyl, as well as its geometric isomers, its salts of organic or mineral bases and its solvates such as its hydrates.
[0147] As examples of water-soluble coloring materials suitable for the invention, mention may also be made of red, blue or yellow gardenia extracts, carotenes, such as beta-carotene, paprika, and curcumin, the colored active ingredients of which have the following formula, or one of its geometric isomers, its salts of organic or mineral bases or its solvates, in particular its hydrates:
[0148] [Chem. 8]
[0149] in which R7, R8, R9 and R10 represent, independently of one another, a hydrogen atom, a hydroxyl group or a (Ci-C6)alkoxy group, preferably (Ci-C4)alkoxy, in particular methoxy, it being understood that at least one of the groups R7 to R10 represents a hydroxyl group.
[0150] Preferably, R8 and R10 represent a hydroxyl group, R7 represents a hydrogen atom or a (Ci-C4)alkoxy group, in particular methoxy, and R9 represents a hydrogen atom or a (Ci-C4)alkoxy group, in particular methoxy.
[0151] According to a preferred embodiment, the water-soluble coloring matter is chosen from: - pyran or pyranium colorants, in particular anthocyanins and anthocyanosides, preferably red radish extracts, sweet potato extracts, in particular purple sweet potatoes; - polyene dyes chosen in particular from jasminoids, in particular those whose colored active ingredients have the following formula:
[0152] [Chem.9]
[0153] in which: R11 and R16, 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) (Ci-C6)alkyl, preferably (Ci-C4)alkyl, in particular methyl, ii) a cycloalkylcarbonyl group in which the cycloalkyl group 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 (Ci-C6)alkyl group, preferably (Ci-C4)alkyl, in particular methyl; iv) sugar, in particular glycosylated, glycosyloxy; or (v) sugar-C(O)-; and R12 to R15, identical or different, preferably identical, represent a hydrogen atom or a (Ci-C6)alkyl group, preferably R12 to R15 represent a (CrC4)alkyl group, for example methyl; as well as its geometric isomers, its salts of organic or mineral bases and its solvates such as its hydrates; and - curcumin, the colored active ingredients of which have the following formula:
[0154] [Chem. 10]
[0155] in which R7, R8, R9 and R10 represent, independently of one another, a hydrogen atom, a hydroxyl group or a (Ci-C6)alkoxy group, preferably (CrC4)alkoxy, in particular methoxy, it being understood that at least one of the groups R7 to R10 represents a hydroxyl group; preferably R8 and R10 represent a hydroxyl group, R7 represents a hydrogen atom or a (CrC4)alkoxy group, in particular methoxy, and R9 represents a hydrogen atom or a (CrC4)alkoxy group, in particular methoxy, as well as its geometric isomers, its salts of organic or mineral bases and its solvates such as its hydrates.
[0156] As other examples of water-soluble coloring materials suitable for the invention, mention may be made of phthalocyanines and porphyrins, in particular complexed with a preferably transition metal (such as titanium, manganese, iron, cobalt, nickel, copper, zinc, in particular magnesium or copper), such as chlorophyll, chlorophyllin and their metal complexes, in particular their transition metal complexes, in particular titanium, manganese, iron, cobalt, nickel, copper, zinc, in particular magnesium or copper, preferably copper.
[0157] More preferably, a water-soluble coloring material suitable for the invention may be chosen from: i) Paprika, in particular that marketed under the name CAPSANTHIN / CAPSORUBIN by the company VITIVA; ii) Beta-carotene, in particular that marketed under the name BETA-CAROTHENE by the company VITIVA; iii) Red Radish extract, in particular that marketed under the name RAPHANUS SATIVUS ROOT EXTRACT by the company VITIVA, and whose coloring active ingredient is enocyanin; iv) Purple Sweet Potato extract, in particular that marketed under the name ANTHOCYANINS / IPOMOEIA BATAT AS ROOT EXTRACT by the company VITIVA, which is an extract of the roots of Ipomoea batatas, Convolvulaceae; v) Yellow Gardenia, in particular that marketed under the name GARDENIA YELLOW- GARDENIA JASMINOIDES FRUIT EXTRACT by the company HENAN ZHONGDA BIOLOGICAL; vi) Red Gardenia, in particular that marketed under the name GARDENIA FRUIT EXTRACT FOR WATER SOLUBLE RED by the company HENAN ZHONGDA BIOLOGICAL; (vii) Blue Gardenia, in particular that marketed under the name GARDENIA BLUE - HYDROLYZED GARDENIA FLORIDA EXTRACT WITH MALTODEXTRIN by the company HENAN ZHONGDA BIOLOGICAL; (viii) Curcumin, in particular that marketed under the name CURCUMA LONGA EXTRACT TBC by the company NATUREX; and ix) Blue Pea extract, in particular that marketed under the name CLITORIA TERNATEA FLOWER EXTRACT by the company NATURAL-SOLUTION.
[0158] According to a preferred embodiment, the water-soluble coloring matter is chosen from pyran dyes, polyene dyes, red and blue gardenia extracts or yellow, carotenes, paprika, curcumin, and mixtures thereof, in particular among paprika, beta-carotene, red radish extract, purple sweet potato extract, yellow, red or blue gardenia, curcumin, blue pea extract, and mixtures thereof.
[0159] According to a particular embodiment of the invention, the coloring matter(s) of the invention is(are) chosen from organic pigments.
[0160] Among the organic pigments of the invention, mention may be made of carbon black, D & C type pigments (in particular azo, anthraquinone, nitrated and tria-rylmethane), and lakes based on cochineal carmine, barium, strontium, calcium, aluminum, preferably D & C type pigments.
[0161] According to a particular embodiment of the invention, the coloring material(s) of the invention is(are) chosen from anionic, cationic, zwitterionic or neutral water-soluble dyes, and more particularly anionic dyes (i.e. commonly called “acid” direct dyes for their affinity with alkaline substances).
[0162] By "anionic dyes" is meant any having in its structure at least one CO2R' or SO3R' substituent with R' denoting a hydrogen atom or a cation originating from a metal or an amine, or an ammonium ion.
[0163] The anionic dyes may be chosen from acid nitro direct dyes, acid azo dyes, acid azine dyes, acid tria-rylmethane dyes, acid indoamine dyes, acid anthraquinone dyes, indigoids and acid natural dyes.
[0164] As anionic dyes suitable for the invention, mention may be made of dyes chosen from those of formulae (G), (G'), (J), (J'), (K), (K'), (L), and (M), following and their mixtures, in particular of formulae (G), (J) and (L) and their mixtures:
[0165] a) the anionic azo dyes of formulae (G) and (G') below:
[0166] [Chem. 11]
[0167] [Chem. 12] (G'}
[0168] formula in which R7, R8, R9, R10, R'7, R'8, R'9 and R'1O, identical or different, represent a hydrogen atom, halogen or a group chosen from: - alkyl; - alkoxy, alkylthio; - hydroxy, mercapto; - nitro, nitroso; - R°-C(X)-X'-, R°-X'-C(X)-, R°-X'-C(X)-X”- with R° representing a hydrogen atom, an alkyl or aryl group; X, X' and X”, identical or different, representing an oxygen, sulfur or NR atom with R representing a hydrogen atom or an alkyl group; - (O)2S(O-)-, M+ with M+ representing a hydrogen atom or a cationic counterion; - (O)CO—, M+ with M+ as defined previously; - R”-S(O)2-, with R” representing a hydrogen atom, an alkyl group, an aryl group, (di)(alkyl)amino, aryl(alkyl)amino; preferably a phenylamino or phenyl group; - R'”-S(O)2-X'- with R”' representing an alkyl, aryl group optionally substituted, X' being as defined previously; - (di)(alkyl)amino; - aryl(alkyl)amino optionally substituted by one or more groups chosen from i) nitro; ii) nitroso; iii) (O)2S(O-)-, M+ and iv) alkoxy with M+ as defined previously; - optionally substituted heteroaryl; preferably a benzothiazolyl group; - cycloalkyl; in particular cyclohexyl; - Ar-N=N- with Ar representing an optionally substituted aryl group; preferably a phenyl optionally substituted by one or more alkyl, (O)2S(O-)-, M+ or phenylamino groups; - or two contiguous groups R7 with R8 or R8 with R9 or R9 with R10 together forming a fused benzo group A'; and R'7 with R'8 or R'8 with R'9 or R'9 with R'10 together forming a fused benzo group B'; with A' and B' optionally substituted by one or more groups chosen from nitro; nitroso; (O)2S(O-)-, M+; hydroxy; mercapto; (di)(alkyl)amino; R°-C(X)-X'-; R°-X'-C(X)-; R°-X'-C(X)-X”-; Ar-N=N- and optionally substituted aryl(alkyl)amino; with M+, R°, X, X', X” and Ar as defined above; and in which: - W represents a sigma o bond, an oxygen atom, a sulfur atom, or a divalent radical -NR- with R as defined above, or methylene -C(Ra)(Rb)- with Ra and Rb, identical or different, representing a hydrogen atom or an aryl group, or Ra and Rb together form, with the carbon atom which carries them, a spiro cycloalkyl; preferably W represents a sulfur atom or Ra and Rb together form a cyclohexyl; it being understood that formulas (G) and (G') comprise at least one sulfonate radical (O)2S(O-)-, M+ or one carboxylate radical (O)CO—, M+ on one of the rings A, A', B, B' or C; preferably sodium sulfonate.
[0169] A titre d’exemple de colorants de formule (G) on peut citer : 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 ou sunset yellow ; et à titre d’exemple de colorants de formule (G’) on peut citer : Acid Red 111, Acid Red 134, Acid Yellow 38.
[0170] b) les colorants anthraquinones de formules (J) et (J’) ci-dessous :
[0171] [Chem. 13]
[0172] [Chem. 14]
[0173] formulas (J) and (J') in which R22, R23, R24, R2s, R26 and R27, identical or different, represent a hydrogen atom, halogen atom, or a group chosen among : - alkyl; - hydroxy, mercapto; - alkoxy, alkylthio; - optionally substituted aryloxy or arylthio, preferably substituted by one or more groups chosen from alkyl and (O)2S(O-)-, M+ with M+ as defined previously; - aryl(alkyl)amino optionally substituted by one or more groups chosen from alkyl and (O)2S(O-)-, M+ with M+ as defined previously; - (di)(alkyl)amino; - (di)(hydroxyalkyl)amino; - (O)2S(O-)-, M+ with M+ as defined previously; and in which: Z' represents a hydrogen atom or a group NR28R29 with R28 and R29, 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, n-butyl; ii) (O)2S(O-)-, M+ 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, preferably R° represents an alkyl group; - cycloalkyl; in particular cyclohexyl; Z, represents a group chosen from hydroxy and NR'28R'29 with R'28 and R'29, identical or different, represent the same atoms or groups as R28 and R29 as defined previously; it being understood that formulas (J) and (J') comprise at least one sulfonate radical (O)2S(O-)-, M+ or one carboxylate radical -C(O)O-, M+; preferably sodium sulfonate.
[0174] As examples of dyes of formula (J) we can cite: 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 as examples of dyes of formula (J') we can cite: Acid Black 48.
[0175] d) the nitrated dyes of formulae (K) and (K') below:
[0176] [Chem. 15]
[0178] in which R30, R3i and R32, identical or different, represent a hydrogen atom, a halogen atom, or a group chosen from: - alkyl; - alkoxy optionally substituted by one or more hydroxy groups, alkylthio optionally substituted by one or more hydroxy groups; - hydroxy, 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 previously; - (O)2S(O-)-, M+ with M+ as defined previously; - (O)CO—, M+ with M+ as defined previously; - (di)(alkyl)amino; - (di)(hydroxyalkyl)amino; - heterocycloalkyl such as piperidino, piperazino or morpholino; particularly R30, R3i and R32 represent a hydrogen atom; and in which: - Rc and Rd, identical or different, represent a hydrogen atom or an alkyl group; - W is as defined above; W particularly represents a -NH- group; - ALK represents a linear or branched divalent alkylene group, C1-C6; particularly ALK represents a -CH2-CH2- group; - n is 1 or 2; - p represents an integer between 1 and 5 inclusive; - q represents an integer between 1 and 4 inclusive; - u is 0 or 1; - when n is 1, J represents a nitro, or nitroso group; particularly nitro; - when n is 2, J represents an oxygen atom, sulfur, or a divalent radical —S(O)m— with m representing an integer 1 or 2; preferably J represents a radical -SO2-; - M' represents a hydrogen atom or a cationic counterion;
[0179] [Chem. 17]
[0180] present or absent represents a benzo group optionally substituted by one or more R30 groups as defined previously; it being understood that formulas (K) and (K') comprise at least one sulfonate radical (O)2S(O-)-, M+ or one carboxylate radical -C(O)O-, M+; preferably sodium sulfonate.
[0181] Examples of dyes of formula (K) include: Acid Brown 13, Acid Orange 3; examples of dyes of formula (K') include: Acid Yellow 1, 2,4-dinitro-1-naphthol-7-sulfonic acid sodium salt, 2-piperidino 5-nitro benzene sulfonic acid, 2(4'-N,N(2”-hydroxyethyl)amino-2'-nitro)aniline ethane sulfonic acid, 4-[3-hydroxyethylamino-3-nitrobenzene sulfonic acid; EXT D&C yellow 7.
[0182] e) triarylmethane dyes of formula (L) below:
[0183] [Chem. 18]
[0184] formula (L) in which: - R33, R34, R35 and R36, 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 a (O)mS(O-)-, M+ group with M+ and m as defined previously; - R37, R38, R39, R40, R41, R42, R43 and R44, identical or different, represent a hydrogen atom or a group chosen from: - alkyl; - alkoxy, alkylthio; - (di)(alkyl)amino; - hydroxy, mercapto; - nitro, nitroso; - R°-C(X)-X'-, R°-X'-C(X)-, R°-X'-C(X)-X”- with R° representing a hydrogen atom, an alkyl or aryl group; X, X' and X”, identical or different, representing an oxygen, sulfur or NR atom with R representing a hydrogen atom or an alkyl group; - (O)2S(O-)-, M+ with M+ representing a hydrogen atom or a cationic counterion; - (O)CO—, M+ with M+ as defined previously; - or 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; (O)2S(O-)-, M+; hydroxy; mercapto; (di)(alkyl)amino; R°-C(X)-X'-; R°-X'-C(X)-; ix) R°-X'-C(X)-X”-; with M+, R°, X, X', X” as defined previously; particularly R37 to R40 represent a hydrogen atom, and R4[ to R44, identical or different, represent a hydroxy group or (O)2S(O-)-, M+; and when R43 with R44 together form a benzo group, it is preferentially substituted by a (O)2S(O-)- group; it being understood that at least one of the cycles G, H, I or I' comprises at least one sulfonate radical (O)2S(O-)- or a carboxylate radical -C(O)O-; preferably sulfonate.
[0185] As examples of dyes of formula (L) we can cite: Acid Blue 1, Acid Blue 3, Acid Blue 7, Acid Blue 9, Acid Violet 49, Acid green 3, Acid green 5, Acid Green 50.
[0186] f) xanthene-derived dyes of formula (M) below:
[0187] [Chem. 19] R,, (V)
[0188] formula (M) in which R45, R46, R47 and R48, identical or different, represent a hydrogen atom or a halogen atom and R49, R50, R51 and R52, identical or different, represent a hydrogen atom, a halogen atom, or a group chosen from: - alkyl; - alkoxy, alkylthio; - hydroxy, mercapto; - nitro, nitroso; - (O)2S(O-)-, M+ with M+ representing a hydrogen atom or a cationic counterion; - (O)CO—, M+ with M+ as defined previously; particularly R49, R50, R51 and R52 represent a hydrogen or halogen atom; and in which: - G represents an oxygen atom, sulfur atom or an NRe group with Re representing a hydrogen atom or an alkyl group; particularly G represents an oxygen atom; - L represents an alcoholate O-, M+; a thioalcoholate S-, M+ or an NRf group, with Rf representing a hydrogen atom or an alkyl group, and M+ as defined previously; M+ is particularly sodium or potassium; - L' represents an oxygen atom, sulfur atom or an ammonium group: N+RfRg, with Rf and Rg, identical or different, representing a hydrogen atom, an alkyl group, possibly substituted aryl; L' particularly represents an oxygen atom or a phenylamino group optionally substituted by one or more alkyl groups or (O)mS(O-)-, M+ with m and M+ as defined previously; - Q and Q', identical or different, represent an oxygen or sulfur atom; particularly Q and Q' represent an oxygen atom; - M+ is as defined previously.
[0189] As coloring materials suitable for the invention, mention may in particular be made 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 mixtures thereof, more preferably chosen from FDC Red 4, DC Red 33, DC Orange 4, DC Yellow 5, DC Green 5 and FDC Blue 1, as well as mixtures thereof.
[0190] Among the natural direct dyes that can be used according to the invention as coloring matter, mention may be made of lawsone, juglone, alizarin, purpurin, carmine & carminic acid, kermesic acid, purpurogallin, protocatechaldehyde, indigo, isatin, curcumin, spinulosin, apigenidin, orceins, betanin (beetroot), metallic chlorophyllin, in particular copper, methylene blue, caramel, sandalwood, gardenia, spirulina and riboflavin.
[0191] Preferably, as water-soluble dyes suitable for the invention, mention may in particular be made 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, orthodiphenol derivatives, in particular anthocyanins (red radish, red cabbage, purple sweet potato, purple corn, black carrot, hibiscus, blue elderberry pea), caramel, sandalwood, gardenia, spirulina and riboflavin.
[0192] The water-soluble coloring materials suitable for the invention may be in the form of acid or base salts, in particular mineral or organic acids, in particular hydrochloric acid or mineral or organic bases, such as alkali hydroxides including sodium hydroxide.
[0193] The water-soluble coloring materials suitable for the invention may be glycosylated, that is to say, contain one or more glycosylated groups.
[0194] All the enantiomers of the coloring matters defined above can be suitable as coloring matters, as can the racemic mixtures.
[0195] The water-soluble coloring matter, in particular derived from natural extract(s), suitable for the invention may be in any form allowing its solubilization. in the perfumed composition, in particular in an aqueous, alcoholic or hydroalcoholic medium. It may in particular be in powder or liquid form, preferably in powder form.
[0196] For obvious reasons, the quantity of water-soluble coloring matter(s) present in a composition according to the invention is likely to vary significantly with regard to the shade or chromatic intensity sought by its presence.
[0197] Preferably, the water-soluble coloring matter(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 coloring matter(s) or the extract(s) containing them.
[0198] As regards the pure water-soluble coloring matter(s) b), the content in the perfuming composition containing them preferably varies from 0.0001% to 5% by weight, preferably from 0.001% to 3.0% by weight, more preferably from 0.01% to 1.0% by weight, and even more preferably from 0.1% to 0.5% by weight, of water-soluble coloring matter(s), relative to the total weight of said composition.
[0199] According to a particular embodiment of the invention, the total quantity of water-soluble coloring matter(s) contained in the composition varies from 1 to 300 ppm (part(s) per million), and more particularly from 1 to 200 ppm.
[0200] Advantageously, a content of water-soluble coloring matter(s) less than or equal to 300 ppm in the perfumed colored composition makes it possible to prevent the formation of traces during its application, in particular on clothing, regardless of the coloring matter used.
[0201] As mentioned above, the water-soluble coloring matter may be introduced into the perfumed composition of the invention in the form of a natural extract.
[0202] Thus, a perfumed composition according to the invention may comprise from 0.05% to 15% by weight of natural extract comprising a water-soluble coloring matter, relative to the total weight of said composition.
[0203] Preferably, a composition according to the invention comprises from 0.0001% to 20% by weight of the water-soluble coloring matter(s) of the total weight of the composition containing the coloring matter(s) or the extract(s) containing them, preferably: - when the water-soluble coloring matter(s) is / are pure, the content in the perfuming composition varies from 0.0001% to 5% by weight, preferably from 0.001% to 3.0% by weight, more preferably from 0.01% to 1.0% by weight, and even more preferably from 0.1% to 0.5% by weight, of the water-soluble coloring matter(s), relative to the total weight of said composition; - when the water-soluble coloring matter(s) is / are in the form of extract(s), the content in the composition of extract(s) 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, preferably from 0.3% to 3.0% by weight, and more preferably from 0.4% to 2.0% by weight, better still from 0.5% to 1% by weight of extract(s) in said composition, relative to the total weight of said composition. Fragrance substance
[0204] As mentioned previously, a perfumed composition according to the invention comprises at least one perfume substance.
[0205] Perfumes are compositions containing in particular the raw materials described in S. Arctander, Perfume and Flavor Chemicals (Montclair, NJ, 1969), in S. Arctander, Perfume and Flavor Materials of Natural Origin (Elizabeth, NJ, 1960) and in “Flavor and Fragrance Materials - 1991”, Allured Publishing Co. Wheaton, 111.
[0206] A perfumed composition according to the invention preferably comprises at least one perfuming substance chosen from essential oils, perfumes and aromas of synthetic or natural origin, and their mixtures.
[0207] These may 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, peroxides, saturated or unsaturated, aliphatic or cyclic.
[0208] According to the definition given in the 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 raw material, either by steam distillation, or by dry distillation, or by a suitable mechanical process without heating (cold expression). The essential oil is most often separated from the aqueous phase by a physical process which does not cause a significant change in the composition.
[0209] The choice of method for obtaining essential oils depends mainly on the raw material: its original state and its characteristics, its nature itself. The “essential oil / plant raw 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, color, solubility, volatility, enrichment or depletion in certain constituents.
[0210] Steam entrainment corresponds to the vaporization in the presence of water vapor of a substance that is poorly miscible with water. The raw material is placed in the presence of boiling water or water vapor in a still. The water vapor entrains the essential oil vapor which is condensed in the refrigerant to be recovered in liquid phase in a Florentine vase (or essencier) where the essential oil is separated from the water by decantation. The aqueous distillate that remains after steam distillation, once the essential oil has been separated, is called "aromatic water" or "hydrosol" or "floral distilled water".
[0211] Obtaining by dry distillation consists of obtaining the essential oil by distillation of wood, bark or roots, without adding water or water vapor in a closed enclosure designed so that the liquid is recovered in its lower part. Cade oil constitutes the best known example of this method of obtaining.
[0212] The cold expression method only applies to citrus fruits (Citrus spp) by mechanical processes at room temperature. The principle of the method is as follows: the zests are shredded and the contents of the secretory pockets that have been broken are recovered by a physical process. The classic process consists of exerting an abrasive action on the entire surface of the fruit under a stream of water. After removing the solid waste, the essential oil is separated from the aqueous phase by centrifugation. Most industrial installations actually allow the simultaneous or sequential recovery of fruit juices and essential oil.
[0213] Essential oils are generally volatile and liquid at room temperature, which differentiates them from so-called fixed oils. They are more or less colored and their density is generally lower than that of water. They have a high refractive index and most of them deflect polarized light. They are liposoluble and soluble in common organic solvents, entrainable by water vapor, very slightly soluble in water.
[0214] Among the essential oils that can be used according to the invention, mention may be made of those obtained from plants belonging to the following botanical families: Abietaceae or Pinaceae, for example conifers; Amaryllidaceae; Anacardiaceae; Anonaceae, for example ylang; Apiaceae, for example umbellifers, in particular dill, angenic, coriander, fennel, carrot or parsley; Araceae; Aristolochiaceae; Asteraceae for example yarrow, mugwort, chamomile, and helichrysum; Betulaceae; Brassicaceae; Burseraceae, for example frankincense; Caryophyllaceae; Canellaceae; Caesalpiniaceae for example copaifera (copahu); Chenopodaceae; Cistaceae for example cistus; Cyperaceae; Dipterocarpaceae; Ericaceae e.g. wintergreen; Euphorbiaceae; Fabaceae; Geraniaceae e.g. geranium; Guttiferae; Hamamelidaceae; Hernandiaceae; Hypericaceae e.g. St. John's wort; Iridaceae; Juglandaceae;Lamiaceae, e.g. thyme, oregano, bee balm, savory, basil, marjoram, mint, patchouli, lavender, sage, catnip, rosemary, hyssop, lemon balm, rosemary; Lauraceae, e.g. ravensara, bay, rosewood, cinnamon, litsea; Liliaceae, e.g. garlic; Magnoliaceae, e.g. magnolia; Malvaceae; Meliaceae; Monimiaceae; Moraceae, for example hemp, or hops; Myricaceae; Mysristicaceae, for example nutmeg; Myrtaceae, for example eucalyptus, tea tree, niaouli, cajuput, backousia, clove, myrtle; Oleaceae; Piperaceae, for example pepper; Pittosporaceae; Poaceae, for example lemongrass, lemongrass, vetiver; Polygonaceae; Ranunculaceae; Rosaceae, for example roses; Rubiaceae; Rutaceae, for example all citrus; Salicaceae; Santalaceae, for example sandalwood; Saxifragaceae; Schisandraceae; Styracaceae, for example benzoin; Thymelaceae, for example agarwood; Tilliaceae; Valerianaceae, e.g. valerian, spikenard; Verbenaceae, e.g. lantana, verbena; Violaceae; Zingiberaceae, e.g. galangal, turmeric, cardamom, ginger; Zygophyllaceae.
[0215] Mention may also be made of essential oils extracted from flowers (lily, lavender, rose, jasmine, ylang-ylang, neroli), stems and leaves (patchouli, geranium, petitgrain), fruits (coriander, anise, cumin, juniper), fruit peels (bergamot, lemon, orange), roots (angelica, celery, cardamom, iris, sweet flag, ginger), wood (pine wood, sandalwood, guaiac wood, rose cedar, camphor), herbs and grasses (tarragon, rosemary, basil, lemon grass, sage, thyme), needles and branches (spruce, fir, pine, dwarf pine), resins and balsams (galbanum, elemi, benzoin, myrrh, frankincense, opopanax).
[0216] Examples of fragrance substances include: geraniol, geranyl acetate, famesol, borneol, bomyl acetate, linalool, linalyl acetate, linalyl propionate, linalyl butyrate, tetrahydrolinalool, citronellol, citronellyl acetate, citronellyl formate, citronellyl propionate, di-hydromyrcenol, 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, benzoate benzyl, amyl salicylate, dimethylbenzyl carbinol, trichloromethylphenylcarbinyl acetate, p-tert-butylcyclohexyl acetate, isononyl acetate, vetiveryl acetate, vetiverol, alpha-hexylcinnamaldehyde, 2-methyl-3-(p-tert-butylphenyl)propanal,2-methyl-3-(p-isopropylphenyl)propanal, 3-(p-tert-butylphenyl)propanal, 2,4-dimethylcyclohex-3-enyl-carboxaldehyde, tricyclodecenyl acetate, tricyclodecenyl propionate, 4-(4-hydroxy-4-methylpentyl)-3-cyclohexenecarboxaldehyde, 4-(4-methyl 1-3-penteny 1)-3-cyclohexenecarboxaldehyde, 4-acetoxy-3-pentyl-tetrahydropyran, 3-carboxymethyl-2-pentylcyclopentane, 2-n-4-heptylcyclopentanone, 3-methyl-2-pentyl-2-cyclopentenone, menthone, carvone, tagetone, geranyl acetone, n-decanal, n-dodecanal, 9-decenol-l, , phenoxyethyl isobutyrate, phenylacetaldehyde dimethylacetal, phenylacetaldehyde diethylacetal, geranonitrile, citronellonitrile, cedryl acetate, 3-isocamphylcyclohexanol, cedryl methyl ether, isolongifolanone, hawpinonitrile, hawthorn, heliotropin, coumarin, eugenol, vanillin, diphenyl ether, citral, citronellal, hydroxycitronellal, damascone, ionones, methylionones, isomethylionones, solanone, irones, cis-3-hexenol and its esters, musk indans, musk tetralins, musk isochromans, macrocyclic ketones, musks-macrolactones, aliphatic musks, ethylene brassylate and their mixtures.
[0217] A perfumed composition according to the invention preferably comprises a perfuming substance chosen from essential oils, perfumes and aromas of synthetic or natural origin, and their mixtures.
[0218] According to a preferred embodiment of the invention, a mixture of different perfuming substances is used which together generate a pleasant note for the user.
[0219] Thus, according to a preferred embodiment, the perfumed composition comprises at least 1% by weight of a mixture of perfume substances, in particular of at least two distinct perfume substances, relative to the total weight of the composition, and preferably of at least three distinct perfume substances.
[0220] The perfuming substances will preferably be chosen so that they produce notes (head, heart and base) in the following families: citrus, aromatic, floral notes, particularly pink flowers and white flowers, spicy, woody, gourmand, chypre, fern, leather, and musk.
[0221] For obvious reasons, the quantity of perfuming substance(s) present in a composition according to the invention is likely to vary significantly with regard to the odor or odor intensity sought by its presence.
[0222] By way of illustration, a perfumed composition according to the invention may 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, preferably from 0.1% to 1.0% by weight of perfume substance(s), relative to the total weight of said composition.
[0223] As mentioned above, the perfume substances can be introduced into a perfumed composition in accordance with the invention in the form of a perfume concentrate.
[0224] The perfume concentrate may be a concrete or an absolute, preferably an absolute.
[0225] Thus, a perfumed composition according to the invention particularly comprises 1.0 % to 50% by weight of perfume concentrate, more particularly from 2.0% to 40% by weight, preferably from 5.0% to 30% by weight, more preferably from 10% to 20% by weight, for example 15% by weight, relative to the total weight of the com- position. Composition
[0226] A perfumed composition according to the invention can be presented in all the galenic forms conventionally used for topical application and in particular in the form of an alcoholic or hydroalcoholic solution or suspension, an emulsion of liquid or semi-liquid consistency of the milk type, obtained by dispersion of a fatty phase in an aqueous phase (O / W) or vice versa (W / O), or a suspension or emulsion of soft consistency of the cream type (O / W) or (W / O), or an anhydrous gel, or any other cosmetic form.
[0227] Preferably, a perfumed composition according to the invention is an alcoholic composition, namely comprising an alcohol or mixture of alcohols as solvent(s), or hydroalcoholic, namely comprising a mixture of water and alcohol as solvents.
[0228] According to a preferred embodiment, a perfumed composition according to the invention is an alcoholic or hydroalcoholic composition, preferably the composition comprises as solvent(s) ethanol, optionally mixed with water and / or pentylene glycol.
[0229] Preferably, the composition according to the invention is hydroalcoholic.
[0230] In addition to the ethanol present in a content strictly greater than 15% by weight, a composition according to the invention may also comprise other alcohols other than ethanol, called “additional alcohols”. Additional alcohols
[0231] The additional alcohols which are 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.
[0232] In particular, a perfumed composition according to the invention comprises, as solvent(s), water and (bio)ethanol optionally mixed with pentylene glycol.
[0233] 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
[0234] A composition according to the invention is preferably hydroalcoholic.
[0235] A hydroalcoholic perfumed composition according to the invention may comprise, in addition to water and ethanol, one or more water-soluble solvents distinct from the additional alcohols defined above.
[0236] By "water-soluble solvent" is meant in the present invention a compound liquid at room temperature and miscible with water (miscibility in water greater than 50% by weight at a temperature ranging from 20°C to 25°C and atmospheric pressure).
[0237] The water-soluble solvents that can be used in the composition of the invention may also be volatile. Among the water-soluble solvents that can be used in the composition in accordance with the invention, mention may in particular be made of C3 and C4 ketones and C2-C4 aldehydes.
[0238] Alternatively, a perfumed composition according to the invention may 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, or even is completely free of water. Polyols
[0239] A perfumed composition according to the invention may also comprise at least one C2-C32 polyol. For the purposes of the present invention, the term "polyol" should be understood to mean 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 room temperature. A polyol suitable for the invention may be a compound of the alkyl type, linear, branched or cyclic, saturated or unsaturated, bearing on the alkyl chain at least three -OH functions, in particular at least four -OH functions.
[0240] The polyols advantageously suitable for the formulation of a composition according to the present invention are those having in particular from 2 to 32 carbon atoms, preferably 3 to 16 carbon atoms.
[0241] Preferably, the polyol may be chosen, for example, from pentaerythritol, trimethylolpropane, glycerol, polyglycerols, in particular glycerol oligomers, preferably diglycerol, and mixtures thereof. Fatty body
[0242] A perfumed composition according to the invention may comprise one or more fatty substances which are liquid at room temperature and / or a fatty substance which is solid at room temperature such as waxes, pasty fatty substances, gums and mixtures thereof. For the purposes of the invention, the term "room temperature" means a temperature equal to 25°C.
[0243] Preferably, the fatty substances suitable for the present invention are liquid at room temperature and atmospheric pressure.
[0244] The oils can be polar or non-polar, of different chemical natures, alone or in a mixture.
[0245] In particular, polar oils that may be mentioned include: - hydrocarbon vegetable oils with a high triglyceride content consisting of fatty acid esters and glycerol, such as wheat germ oils, corn, sunflower, shea, castor oil and sweet almonds; - synthetic esters and ethers; - saturated fatty alcohols C12 to C26; and mixtures thereof.
[0246] Furthermore, the non-polar oils may be chosen in particular from silicone oils such as volatile or non-volatile, linear or cyclic polydimethylsiloxanes, liquid at room temperature (20°C + / - 5°C) and atmospheric pressure, linear or branched hydrocarbons of synthetic or mineral origin.
[0247] Examples of solid fatty substances that may be cited are waxes, in particular hydrocarbon or silicone waxes, of natural or synthetic origin, provided that these are compatible with the other components of the composition, and that they do not alter the properties, in particular the olfactory and color properties, of the perfumed composition.
[0248] Preferably, the fatty substances are vegetable oils. Examples of vegetable oils that may be mentioned are sunflower oil, virgin olive oil, refined sesame oil, etc. Surfactants
[0249] A perfumed composition according to the invention may also comprise one or more surfactants, anionic, cationic, non-ionic, zwitterionic or amphoteric.
[0250] As non-ionic surfactant, mention may be made in particular of fatty acid and sugar esters, in particular those chosen from the group comprising esters or mixtures of C8-C22 fatty acid esters and sucrose, maltose, glucose or fructose, and esters or mixtures of C14-C22 fatty acid esters and methylglucose. Examples of esters or mixtures of esters of fatty acids and sucrose, maltose, glucose or fructose include sucrose monostearate, sucrose distearate, sucrose tristearate and mixtures thereof, and examples of esters or mixtures of esters of fatty acids and methylglucose include methyl glucose distearate and polyglycerol-3, sold by the company Goldschmidt under the name Tego-care 450.
[0251] In addition, the perfumed composition according to the invention may comprise one or more co-emulsifiers. This or these co-emulsifiers may be chosen, for example, from C16-C22 fatty alcohols or C3-C6 polyol esters with C14-C22 fatty acids, and mixtures thereof. As co-emulsifiers, mention may be made, for example, of cetyl alcohol, stearyl alcohol, cetearyl alcohol (mixture of cetyl alcohol and stearyl alcohol), glyceryl stearate, and mixtures thereof, and preferably cetyl alcohol.
[0252] A perfumed composition may comprise from 0.01% to 10% by weight, plus part particularly from 0.1% to 5% by weight, and preferably comprises from 1% to 3% by weight, of surfactant(s) relative to the total weight of the perfumed composition. Preservatives
[0253] A perfumed composition according to the invention may further comprise at least one preservative.
[0254] By "preservative" or "preservative agent" is meant any cosmetically or pharmaceutically acceptable compound that prevents microbial (or microorganism) growth that may occur in cosmetic or pharmaceutical compositions, from their design, through storage, to their conventional use by consumers. As a preservative, we can notably cite 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 / 0471238961.0315191318090507.a01.
[0255] According to a particular embodiment, the preservative(s) are chosen from organic preservatives with an aromatic group.
[0256] A perfumed composition according to the invention may further comprise at least one preservative, in particular chosen from i) benzene carboxylic acids optionally substituted on the phenyl group by one or more groups chosen from hydroxyl, (Ci-Cio)alkyl and (Ci-Cio)alkylacarbonyl, as well as their base salts, in particular of alkali and alkaline earth metals, ii) hydroxybenzoic acid esters and 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] as well as its base salts, in particular of alkali and alkaline earth metals; as well as salicylic acid optionally substituted by a (Ci-C8)alkylcarbonyl group, preferably salicylic acid.The preservative(s) are in particular chosen from aryl(Ci-C6)alkanol and aryloxy(Ci-C6)alkanol, such as phenoxyethanol, parabens, such as propylparaben, methylparaben, butylparaben, ethylparaben, isobutylparaben, benzyl alcohol and / or chlorophenesin. Alkaline agents
[0257] A perfumed composition according to the invention may also comprise at least one alkaline, organic or mineral agent, for example an amine, in particular a (C2-C6)alkanolamine, in particular 2-amino-2-methyl-1-propanol, or mineral such as for example hydroxides of alkali or alkaline earth metals, such as hydroxide of sodium. Chelating agents
[0258] According to a particular embodiment of the invention, the composition comprises one or more chelating agents.
[0259] By "chelating agent" is meant a ligand or chelator which makes it possible to form a metal complex with a cation or a metal atom called chelated. Generally the chelating agent is an electron donor and the chelated is an electron deficient. The "chelate" is distinguished from the simple "complex" by the fact that the metal cation is fixed to the chelating ligand or chelating agent by at least two coordination bonds. The metal is thus "pinched" between the chemical functions of the ligand. The number of metal-ligand bonds in a ligand molecule defines the "denticity": we speak of bidentate, tridentate, tetradentate (or bidentate, tridentate, tetradentate) ligands or ligands. The central atom is linked to the neighboring atoms by at least two bonds, forming a ring structure, a chelate ring. The most stable chelate rings are the 5- and 6-membered chelate rings.Due to this effect, chelates are more stable complexes than monodentate ligand complexes with the same chemical functions.
[0260] 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 alkali metal salts, such as disodium EDTA or dipotassium EDTA, aminopolycarboxylic acids, such as ethylenediaminedisuccinic acid (EDDS), and their salts, in particular alkali metal salts, or one or more phosphate chelating agents such as alkali metal metaphosphate such as sodium metaphosphate, alkali metal hexametaphosphate such as sodium hexametaphosphate, tetraalkaline pyrophosphate such as tetrapotassium pyrophosphate, acids containing phosphorus, such as phytic acid, and their salts, in particular alkali metal salts or alkaline earth salts, such as the salts of ethylenediaminetetramethylenephosphonic acid, alkali metal phytate such as sodium phytate or potassium phytate,and mixtures thereof, preferably chosen from EDTA as defined above and alkali metal phytate such as sodium phytate. Metallic salts
[0261] According to a particular embodiment of the invention, the composition of the invention comprises one or more metal salts, metal complexes, metal oxides, metal oxanions, hydrates and their supported forms.
[0262] Preferably, a composition according to the invention comprises one or more metal salts.
[0263] More particularly, the metal(s) are of oxidation state I or II, more particularly lately II, preferably chosen from 1) Cu; 2) Fe; 3) Zn, 4) Mg and 5) Mn.
[0264] By "metal salt" is meant a compound other than alloys, i.e. the salt is made up of a metal combined with certain non-metallic elements.
[0265] The formation of metal salts results from an oxidative attack. The metal is oxidized into a cationic species and then combines with an anionic species to give a salt. This formation takes place by applying the principles and reaction of redox (chemical reaction during which an electron transfer occurs in which the atom which captures the electrons is called "oxidant"; the one which gives them up, "reducer"); or by chemical exchange reactions between a salt and another salt or an acid, in the presence or absence of atmospheric oxygen. These reactions are known to those skilled in the art.
[0266] Preferably, the salts according to the invention are soluble in water at a proportion of at least 0.0001 g / L.
[0267] The metal salts according to the invention can be introduced in solid form into the compositions or come from natural, mineral or thermal water, rich in these ions or even from sea water (Dead Sea in particular). They can also come from mineral compounds such as plant extracts containing them (see for example document FR 2 814 943).
[0268] By "metal complex" or "coordination compounds" is meant systems in which the metal ion, the central atom, is chemically bonded to one or more electron donors (ligands). A ligand comprising different coordinating groups (capable of coordination with a metal) gives rise to metal compounds corresponding to coordination sphere principles with a determined number of electrons (internal complexes or chelates), as described in Ullmann's Encyclopedia of Industrial Chemistry, "Metal complex dyes", 2005, pp. 1-42.
[0269] More particularly, by metal complex we mean: (i) metallic dyes or “metal-complex dyes” which are complex dyes derived from azo, azomethine, hydrazono, formazan dyes (free, bidendates, tridendates, quadridendates) such as those described in Ullmann's Encyclopedia of Industrial Chemistry, “Metal complex dyes”, 2005, pp. 1-42, which preferably comprise Cu and Mg; ii) compounds of the “aza
[18] annulenes” type or also called “(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, chap. 5, Aza
[18] annulenes, p. 123-160. The metal ion is then located at the center of said macrocycle linked by coordination to 2 hydrogen atoms to the nitrogen atoms of pyrroles, the metal can also be stabilized by one or more bidendate ligands or no; the metal ion being preferentially Mg2+ or Cu2+; particularly, the metal complex is: - a “metalloporphyrin” consisting of a skeleton with 4 pyrrole groups which are linked at their a,a' position by 4 methine groups and contain 16 sp 2 hybridized atoms, complexing a metal such as Cu, Mg; or - a “chlorin” (corresponding to a porphyrin in which an external C=C double bond of a pyrrole group has been reduced) complexed with a metal, preferentially Mg 2+, such as the chromophore of chlorophyll: chlorophyllin; - tetraaza analogue "phthalocyanines" of tetrabenzoporphyrins, such as Monastral Fast Blue B (CI Pigment Blue 15); Monastral Fast Blue G (CI Pigment Blue 16) (see "Color Chemistry," H. Zollinger, 3rd Ed., Wiley-VCH, 2003, chap. 5, Aza
[18] annulenes, p. 140); the sulfonylated derivatives Sirius light Turquoise Blue G (CI Direct Blue 86, Copper tetrasulfonic acid phthalocyanine) and "phthalocyanines" as described in Ullmann's Encyclopedia of Industrial Chemistry, "Phthalocyanines," 2005, pp. 1-34 which include Cu and Si.
[0270] By “metal oxide(s)” is meant the compounds of generic formula AVOV with A representing a metallic 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.
[0271] By "metal oxanion(s)" is meant the compounds of generic formula Z / Aï Ov with A representing a metallic element, Z representing an alkali metal such as Li, Na, 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.
[0272] By "supported form(s)" is meant the forms where the metal derivative b) is impregnated on a material called "support". The possible supports of these metal derivatives can be chosen from carbon, silica, alumina, optionally charged polymers comprising counter-anions or counter-cations (counter-cation or counter-anion of the metal species). For example, the polymers can be polyethylene glycol (PEG).
[0273] According to one embodiment of the invention, the metal salt(s) are chosen from (poly)hydroxyalkyl(Ci-Ci6)carboxyates of metals with oxidation state II, in particular (poly)hydroxyalkyl(Ci-Ci6)carboxyates of Fe II, Cu II, Zn II, Mg II and Mn II. In particular, the metal salt(s) are chosen from Cu gluconate, Fe gluconate, Zn gluconate or Mg gluconate, gluconates of metals with oxidation state II such as gluconates of Fe, Cu, Zn or Mg, lactates of metals with oxidation state II such as lactates of Fe, Cu, Zn or Mg. Preferably, the metal salts are gluconates of Fe, Cu, Mg or Zn, preferably Fe and Cu. Aqueous pH buffers
[0274] A perfumed composition according to the invention may 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.
[0275] The aqueous pH buffer(s) particularly suitable for the invention may be chosen from benzoic acid, maleic acid, fumaric acid, succinic acid and their salts, in particular alkaline or alkaline earth salts, for example sodium benzoate. Additional coloring matters
[0276] A perfumed composition according to the invention may also comprise one or more additional coloring matter, distinct from the water-soluble colorants defined above.
[0277] This (or these) coloring material(s) is (or are) preferably chosen from liposoluble dyes, particulate coloring materials, and their mixtures.
[0278] For the purposes of the invention, the term “liposoluble colorant” means any generally organic, natural or synthetic colorant, soluble in an oily phase or solvents miscible with a fatty substance.
[0279] The coloring particulate materials may be colored pigments (i.e. different from UV filter pigments), nacres and / or particles with metallic reflections.
[0280] For the purposes of the present invention, the term “pigments” means white or colored solid particles, mineral or organic.
[0281] The pigments are naturally insoluble in the liquid hydrophilic and lipophilic phases usually used in cosmetics. They can alternatively be made insoluble by formulation in the form of a lake, if necessary.
[0282] More particularly, the pigment is little or not at all soluble in hydroalcoholic media.
[0283] The pigments may be white or colored, mineral and / or organic, coated or not. Among the mineral pigments, mention may be made of metal oxides, in particular titanium dioxide, optionally surface-treated, zirconium, zinc or cerium oxides, as well as iron, titanium or chromium oxides, manganese violet, ultramarine blue, chromium hydrate and ferric blue.
[0284] These additional coloring materials may be present in a content ranging from 0.01% to 30% by weight relative to the total weight of the composition, in particular from 0.05% to 20% by weight relative to the total weight of the composition. Adjuvants
[0285] A perfumed composition according to the invention may further comprise any adjuvant usually used in the field of perfumes such as, for example, emollients or softeners, in particular sweet almond oils, apricot kernel oils, moisturizing agents, in particular glycerin, soothing agents, in particular α-bisabolol, allantoin and aloe vera; vitamins and their derivatives, essential fatty acids, propellants, peptizers, fillers, co-solvents, UV filters, stabilizers or preservatives other than the compounds of formula (I) as defined according to the invention, and mixtures thereof.
[0286] It is a matter of routine operation for those skilled in the art to adjust the nature and quantity of the adjuvants present in the compositions in accordance with the invention, so that the desired cosmetic properties thereof are not affected.
[0287] 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, relative to the total weight of the composition. Preparation of the composition
[0288] A composition according to the invention can be obtained by any method known to those skilled in the art for the formulation of colored perfumed compositions.
[0289] In particular, a perfumed composition according to the invention can be obtained by simple mixing, at room temperature, namely at a temperature ranging from 20°C to 25°C, of the compounds constituting the composition.
[0290] According to a particular embodiment, a perfumed composition according to the invention results from the mixture between a coloring solution on the one hand and a perfumed solution comprising the compound of formula (I) on the other hand.
[0291] Said coloring solution therefore comprises at least one coloring material, in particular as defined above, in a physiologically acceptable medium, in particular in an aqueous or hydroalcoholic medium.
[0292] Said perfumed solution comprises at least one perfuming 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 relative to its total weight, in a physiologically acceptable medium.
[0293] Said perfumed solution may itself result from a mixture between an intermediate perfumed solution, comprising at least one perfuming substance, in particular as defined above, in a physiologically acceptable medium, in particular in an aqueous or hydroalcoholic medium and a compound of formula (I) as defined above, directly or in solution in a physiologically acceptable medium, in particular in an aqueous or hydroalcoholic medium.
[0294] Alternatively, the compound(s) of formula (I) may be introduced, directly or in solution, into a perfumed composition, further comprising at least at least one perfuming substance, at least one coloring matter and ethanol in a content sufficient for the final composition to comprise strictly more than 15% by weight of ethanol relative to its total weight, in a physiologically acceptable medium.
[0295] It is within the skill of a person skilled in the art to adapt the conditions for preparing a perfumed composition according to the invention. Destination of the composition
[0296] The invention applies not only to perfuming products but also to care products, cosmetic treatment of keratin materials, in particular of the skin, including the scalp, and the lips, containing an odorous substance.
[0297] A composition according to the invention may thus constitute a composition for perfuming, caring for or cosmetically treating keratin materials, and in particular may be in the form of eau fraîche, eau de toilette, eau de parfum, aftershave lotion, care water, silicone or hydrosilicone care oil. It may also be in the form of a perfumed two-phase lotion (eau de toilette phase / hydrocarbon oil phase and / or silicone oil), body milk or shampoo.
[0298] The compositions according to the invention can be packaged in the form of bottles.
[0299] A perfumed composition according to the invention can be diffused using different systems such as sprays, aerosols, piezoelectric devices.
[0300] It can also be applied in the form of fine particles by means of mechanical or propellant gas pressurization devices. The devices according to the invention are well known to those skilled in the art and include pump bottles or "sprays", aerosol containers comprising a propellant as well as aerosol pumps using compressed air as a propellant. The latter are described in particular in US patents 4,077,441 and US 4,850,517.
[0301] The compositions packaged in aerosol form in accordance with the invention generally contain conventional propellants such as, for example, dimethyl ether, isobutane, n-butane, propane.
[0302] The compositions according to the invention are, according to a particular form of the invention, lotions and preferably have a viscosity ranging from 10 to 120 UD, more preferably from 30 to 120 UD, and even more preferably from 40 to 80 UD; the viscosity being measured on the Rhéomat TVe-05, at 25°C, rotation speed 200 rpm, spindle 1, 10 minutes.
[0303] These low viscosities make it possible to condition 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).
[0304] A perfumed composition according to the invention can also be found in the form body milk, or even in the form of shampoo.
[0305] The invention is illustrated in more detail by the examples presented below. Unless otherwise indicated, the quantities indicated are expressed as a mass percentage. Examples Measurement and evaluation methods
[0306] The stability of the compositions is evaluated by observing the evolution of the color over time, visually and using a Konica Minolta CM 3600A spectrocolorimeter (L*, a*, b*).
[0307] In particular, the compositions are poured into 50 mL borosilicate glass hot water bottles and then observed after storage for 2 months, under atmospheric pressure and under different conditions: a) In the refrigerator, at a temperature of 4°C; b) At room temperature, i.e. between 20°C and 25°C, away from 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 room temperature, namely between 20°C and 25°C, then in addition: el) 16 hours in an ATLAS brand SunTest CPS+ aging device, equipped with a Xenon lamp, an irradiating light source with a spectral distribution close to that of the sun, delivering an energy of 765 W / m2, simulating exposure to neon lights in a store; or e.2) 2 weeks in an oven at a temperature of 55°C, simulating an extreme condition for the perfume.
[0308] Storing the compositions for 2 months at 45°C simulates accelerated aging of the product corresponding to a 3-year lifespan.
[0309] The difference in DL intensity between a reference composition and a tested composition after storage under the conditions mentioned above can be calculated from the L*a*b values according to the following formula:
[0310] [Math.l] DL = L2 -
[0311] in which Li* is the color intensity of the reference composition and L2* is the color intensity of the tested composition after storage. Example 1 Preparation of coloring solutions
[0312] The coloring solutions Cl to C13 are prepared from the weight proportions as detailed in Tables 1 and 2 below.
[0313] The values are expressed as a percentage by weight, relative to the total weight of the coloring solution.
[0314] [Tables 1] Composé Cl C2 C3 C4 C5 C6 C7 c§ C9 Ethanol absolu qsp 100 w 100 - - - - - 99.7 99.5 Ethanol - - 63..0 63.0 - - - - - Eau distillée - - 27.0 27..0 qsp 100 68.0 49.0 - - Pentylène glycol - - - - 30.0 50.0 - - CàPSANTHWCAPSORDBIN (Vitiva) Q3 - - - - - - - - BETA-CAROTHENE (Vitiva) - LO - - - - - Raphanus SatjvusRoot EXTRACT (Vitivà) - - 10 - - - - - ÂNTHDCYANîNS / IPOMÔSIÀ Batatas Root Extract (Vitiva) - - 10 - - - - - GARDENIA ŸELLOW - GARDENIA Jasa&noiœs Fruit Extract (Heîian Zhongda BtolagïcaÇ - - - 0,1 - - - - GARDENIA FRUIT EXTRACT FOR Wàter Soluble .Red (Home Zhougda Biological) - - 2,0 - - - GARDENIA BLUE - HYDR.OLYZED Gardénia Florida Extract WlTH MALTQDEXTRIN (Henan Zhongda Biûlogical) - - - - - - L0 - - CURCUMA LONGA EXTRACT TEC (Nature?:) - - - - - - - 03 Clitorfa Ternatea Floâxer Extract (Fhtaaî&oLtion) - - - - - - - 0.5 Tableau l Compound CIO Cil C12 C13 Ethanol 70 70 70 70 Distilled water 29 J 29.7 29.7 29 7 Yellow 5 03 - - - Green 5 - 03 - - Red 33 - - 03 - Red 4 - - 03 Table 2 Protocol for preparing coloring solutions
[0316] The coloring compositions are prepared by dissolving the dyes in the appropriate solvent or mixture of solvents.
[0317] In particular, for a 100 g coloring solution, the necessary quantity of dye is weighed into a beaker. The quantity of solvents (ethanol, water and / or propylene glycol) is then added and the mixture is left to stir under magnetic stirring for 20 minutes. Example 2 Preparation of colored perfume compositions
[0318] Perfumed compositions PI, P2, P3, P4 and P5 according to the invention, and a perfumed composition P6, outside the invention, are prepared from the weight proportions as detailed in Table 3 below.
[0319] The values are expressed as a percent by weight, relative to the total weight of the fragrance composition. Compound PI Invention P2 Invention P3 Invention P4 invention P5 Invention P6 Hors invention Ethanol 78 78 78 78 7S 78 Water QSp 100 qsp 190 qsp 100 qsp 100 qsp 100 qsp ICC SOPHORA JAPHORA EXPORT JOPHORAVE (Japan Extract 85 - Gudm Layn Nateal) 0,1 - - - - - Alpha glucosyl RUHR (Qingdao Taitong Pharmcaeuâca!) - - - - - LUTÉÔLINE (Luteolm — Guifes Layti Nate'al) - - 0J - - A.fYRIŒnNE (Ampélidensis Extractis (Amsélidens) Gusselidence. Layn Natoal) - - - OJ - - QL^RCETINE - - - ... 04 - Perfume concentrate^“l 15:Û 15.0 15.0 15.0 15.C 15.0 Sohit-on dye Cl to C l 3 05 0.05 0.05 0.05 0.50 &Hsé fwsç'&é ; - msas of head of àæ® j^c^, csris?æH -«oSas nss®, - ses afe cwife ripe pæsiæ, rc^ cs^ et - sets ^sîes dk / ôaddfe ftpg^avg .toJ-j&ï, «tac, s^îsT. eto ; and&M f**} Parafa au Aps-tep^de. : - ses iæto a® We de npe a&w væi, citron, esc^-ptas, - 5«? Wes dfe c®«r de ftpe mx de coca Table 3
[0321] Protocol for the preparation of colored perfumed compositions PI to P6
[0322] 15 g of perfume concentrate are weighed into a beaker.
[0323] Ethanol at 95° is added to the perfume concentrate, then water is added.
[0324] For the PI composition, 0.1 g of extract containing at least 85% rutin (Sophora Japonica Bud Extract) is added and then the mixture is left under magnetic stirring for 10 minutes, in order to obtain a perfumed solution.
[0325] 0.05 g of the coloring solution is then added using a pipette.
[0326] Compositions P2 to P5 are prepared according to the same protocol, replacing the extract containing rutin with alpha-glycosyl rutin, luteolin, myricetin or quercetin respectively.
[0327] Composition P6, outside the invention, is prepared according to the same protocol, with the exception of the addition of compound corresponding to formula (I). Example 3 Stability tests
[0328] The stability of the colored perfume compositions is evaluated visually according to the protocol detailed above.
[0329] The evolution of the color of the compositions according to the invention (P1, P2, P3, P4 and P5) and outside the invention (P6), depending on the coloring solution used, is observed visually after 16 hours in the SunTest aging device. The results are detailed in Table 4 below. Composition Pô (Outside invention) Before aging Pé (Outside invention) After aging PI to P5 (Invention) Before aging PI to P5 (Invention) After aging Cl Clear - Orange Clear - Colorless Clear -Orange Clear — Orange C2 Clear - Yellow Clear — Colorless Clear - Yellow Clear — Light yellow C3 Clear - Red L clear - Colorless Clear - Red Clear - Orange red C4 Clear - Violet Clear - Colorless Clear - Violet Clear - Light pink C5 Clear - Yellow Clear - Colorless Clear - Yellow Clear - Light yellow Œ Clear - Violet Clear — Colorless Clear - Violet Clear - Pink C7 Clear - Blue Clear - Colorless.Clear - Blue Clear - Light Blue C8 Clear - Yellow L Clear -Colorless Clear -Yellow Clear - Light Yellow C9 Clear - Blue Clear -Colorless Clear - Blue Clear - Light Blue CIO Clear - Yellow Clear -Colorless Clear - Yellow Clear - Yellow Clear - Light Blue Clear -Colorless Clear - Light Blue Clear - Light Blue C12 Clear - Red Clear -Colorless Clear -Red Clear—Light Red C13 Clear - Fuchsia Clear - Colorless Clear -Fuchsia Clear - Pink . Tables » 4
[0331] The study was carried out with different perfume concentrates from different olfactory families, with similar results being obtained for each perfume concentrate.
[0332] For perfumed compositions PI to P5, according to the invention, the coloring is always visible, whatever the coloring solution tested, after aging in the SunTest device. Furthermore, no olfactory difference was noted after the SunTest.
[0333] On the contrary, composition P6, not comprising a compound corresponding to formula (I) as defined according to the invention, becomes colorless after aging.
[0334] Thus, the composition according to the invention retains its color significantly longer. Furthermore, no significant change in odor was noted during of time.
[0335] Furthermore, the compound of formula (I) used in the composition according to the invention is of natural origin.
[0336] In conclusion, the perfumed composition according to the invention is more stable over time than a composition not in accordance with the invention.
Claims
Claims
1. Perfumed composition, in particular cosmetic, comprising: (a) at least one compound corresponding to formula (I), or one of its geometric isomers, in particular optical isomers, of its tautomers, as well as its salts of organic or mineral acid or base, or its solvates, in particular hydrates: formula (I) in which: ------- represents a double bond or a single bond, R1 represents an atom or a group chosen from: - a hydrogen atom, - a hydroxyl, - a (Ci-C6)alkyl group, - a (Ci-C6)alkoxy group, - a mono- or di-saccharide sugar group, such as glycosylated, or a -O-mono- or di-saccharide sugar group, such as -O-glycosyl; R2 represents a hydrogen atom, a (Ci-C6)alkyl group or a mono- or di-osidic sugar group, such as glycosylated, R3 represents a hydrogen atom or a (Ci-C6)alkyl group, n represents an integer between 1 and 3 and m represents an integer between 0 and 3, it being understood that: when m represents an integer greater than or equal to 2, the radicals R2 may be identical or different, and when n represents an integer greater than or equal to 2, the radicals R3 may be identical or different; b) ethanol in a content strictly greater than 15% by weight, relative to the total weight of the composition; (c) at least one water-soluble coloring matter, said at least one water-soluble coloring matter being distinct from (a); and
2.
3. d) at least one perfume substance. Composition according to the preceding claim, said compound of formula (I) being chosen from luteolin, quercetin, myricetin, rutin, hesperidin, narirutin, alpha-glycosyl rutin, quercitrin, isoquercitrin, morin, hesperetin, chrysin, apigenin, luteolin-7-O-glucoside, 6-hydroxyflavone, 7,8-dihydroxyflavone or tropoflavin, and mixtures thereof. Composition according to any one of the preceding claims, said compound of formula (I) being of formula (!), or one of its geometric isomers, of its tautomers, as well as its salts of organic or mineral acid or base, or its solvates, in particular the hydrates:
4.
5. formula (!) in which: R represents an atom or group chosen from: (i) a hydrogen atom, ii) a hydroxyl, iii) a mono- or di-saccharide sugar group, such as glycosylated, or a -O-mono- or di-saccharide sugar group, such as -O-glycosyl, preferably a glycosylated group or an -O-glycosyl group; iv) a (Ci-C6)alkyl group, v) a (Ci-C6)alkoxy group, n and m represent, independently of each other, an integer between 1 and 3, said compound preferably being chosen from luteolin, quercetin, myricetin, rutin, alpha-glycosyl rutin, and mixtures thereof. Composition according to any one of the preceding claims, said compound of formula (I) or (!') being chosen from natural or naturally occurring compounds. A composition according to any one of the preceding claims, comprising from 0.01% to 5.0% by weight of compound(s) of formula (I),
6.
7. in particular from 0.03% to 2.0% by weight, preferably from 0.05% to 1.0% by weight, more preferably from 0.05% to 0.2% by weight, relative to the total weight of said composition. Composition according to any one of the preceding claims, said water-soluble coloring matter being chosen from natural or naturally occurring water-soluble coloring matters. Composition according to any one of the preceding claims, said coloring material being chosen from: - pyran or pyranium colorants, in particular anthocyanins and anthocyanosides, preferably red radish extracts, sweet potato extracts, in particular purple sweet potatoes; and - polyene dyes chosen in particular from jasminoids, in particular those whose colored active ingredients have the following formula: in which: R11 and R16, 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) (Ci-C6)alkyl, preferably (Ci-C4)alkyl, in particular methyl; ii) a cycloalkylcarbonyl group in which the cycloalkyl group 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 (Ci-C6)alkyl group, preferably (Ci-C4)alkyl, in particular methyl; iv) sugar, in particular glycosylated, glycosyloxy; or v) sugar-C(O)-; and R12 to R15, identical or different, preferably identical, represent a hydrogen atom or a (Ci-C6)alkyl group, preferably R12 to R15 represent a (CrC4)alkyl group, for example methyl; as well as its geometric isomers, its salts of organic or mineral bases and its solvates such as its hydrates. Composition according to any one of the preceding claims, said coloring matter being chosen from organic pigments, in particular chosen from D & C type pigments, and lakes based on cochineal carmine, barium, strontium, calcium, aluminum, preferably D&C type pigments, more preferably 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 their mixtures, even more preferably chosen from FDC Red 4, DC Red 33, DC Orange 4, DC Yellow 5, DC Green 3, DC Green 5, FDC Blue 1 and their mixtures.
9. Composition according to any one of the preceding claims, comprising from 0.0001% to 20% by weight of the water-soluble coloring matter(s) of the total weight of the composition containing the coloring matter(s) or the extract(s) containing them, preferably: - when the water-soluble coloring matter(s) is / are pure, the content in the perfuming composition varies from 0.0001% to 5% by weight, preferably from 0.001% to 3.0% by weight, more preferably from 0.01% to 1.0% by weight, and even more preferably from 0.1% to 0.5% by weight, of the water-soluble coloring matter(s), relative to the total weight of said composition;- when the water-soluble coloring matter(s) is (are) in the form of extract(s), the content in the composition of extract(s) 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, preferably from 0.3% to 3.0% by weight, and more preferably from 0.4% to 2.0% by weight, better still from 0.5% to 1% by weight of extract(s) in said composition, relative to the total weight of said composition.;
10. Composition according to any one of the preceding claims, said perfuming substance being chosen from essential oils, perfumes 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 perfuming substance(s), particularly from 0.001% to 8.0% by weight, more particularly from 0.01% to 5.0% by weight, and preferably from 0.1% at 1.0% by weight, relative to the total weight of said composition.
12. Composition according to any one of the preceding claims, the (bio)ethanol content varying from 16% to 99.5% by weight, in particular from 25% to 97% by weight, more particularly from 35% to 95% by weight, even more particularly from 45% to 90% by weight, relative to the total weight of the composition.
13. Composition according to any one of the preceding claims, in the form of fresh water, eau de toilette, eau de parfum, aftershave lotion, care water, silicone or hydrosilicone care oil, perfumed biphasic lotion, body milk or shampoo.
14. Use of a compound of formula (I) as defined according to any one of claims 1 to 4, as a stabilizer in a perfumed composition, in particular a cosmetic composition, further comprising ethanol in a content strictly greater than 15% by weight, relative to the total weight of the composition, as well as at least one water-soluble coloring matter and at least one perfuming substance.
15. Process for the cosmetic treatment of keratin materials, in particular the skin, or of a garment, comprising at least one step of applying to said keratin materials and / or said garment, a perfumed composition as defined according to any one of claims 1 to 13.