WO2016091937A1

WO2016091937A1 - Aqueous composition comprising hesperetin

Info

Publication number: WO2016091937A1
Application number: PCT/EP2015/079093
Authority: WO
Inventors: Vera Lucie ESTEVES; Chantal JOUY
Original assignee: L'oreal
Priority date: 2014-12-12
Filing date: 2015-12-09
Publication date: 2016-06-16
Also published as: FR3029783B1; FR3029783A1

Abstract

The invention relates to a composition c comprising: - hesperetin; - at least one vinylpyrrolidone homopolymer or copolymer; - at least one polyol; - water. Use for caring for, making up and/or cleansing keratin materials, especially the skin.

Description

Aqueous composition comprising hesperetin

The present invention relates to a composition, preferably a cosmetic composition, comprising hesperetin and at least one polyol.

Hesperetin is an organic compound of the flavanone family, which is a subgroup of the flavonoids. It is found in nature mainly in the form of its heteroside, hesperidin, which is present in fruits of the Citrus genus.

Hesperetin is an advantageous substance as an antioxidant, and for treating the signs of aging of the skin.

However, this compound, which is in solid form at room temperature and has a high melting point (220°C), is difficult to dissolve, and especially is sparingly soluble in water and glycerol.

Now, it is necessary for this compound to be formulated in a solubilized form, and especially in a high content, such as greater than or equal to 0.50% by weight, in order to fully exploit its activity, and it is also preferable for its solubilization to be maintained over time in order to avoid any recrystallization during the storage of compositions comprising such a compound.

The object of the present invention is, precisely, to propose a novel galenical formulation of hesperetin that can overcome the abovementioned drawbacks, in particular which is stable over time, and thus to incorporate this compound in a form that is solubilized and long-lasting, this compound especially being in a high content (such as a content greater than or equal to 0.50% by weight relative to the total weight of the composition). This novel galenical formulation of hesperetin makes it possible especially to improve the efficacy of the active agent for the treatment of keratin materials such as the skin. Specifically, the inventors have discovered, unexpectedly, that the combination of hesperetin with at least one polyol and at least one vinylpyrrolidone homopolymer or copolymer enables this compound to be solubilized while avoiding its recrystallization, especially after storage for two months at room temperature (25°C). More specifically, one subject of the invention is a composition, especially a cosmetic composition, comprising:

- hesperetin;

- at least one vinylpyrrolidone homopolymer or copolymer; - at least one polyol;

- water;

as defined below. The present invention also relates to a process for preparing such a composition, comprising the following steps:

1 ) preparing a solution A by mixing at least one vinylpyrrolidone homopolymer or copolymer and water, and

2) preparing a solution B by mixing hesperetin in at least one polyol, and then

3) mixing the solutions A and B.

Preferably, step 1 ) of said process is the preparation of a solution A by mixing at least one vinylpyrrolidone homopolymer or copolymer and water by simple placing in contact with stirring (for example magnetic stirring) at room temperature (20-25°C).

Preferably, step 2) of said process is the preparation of a solution B by mixing hesperetin in at least one polyol by heating, especially by heating at a temperature of 40-60°C, preferably at 50°C, for 10 minutes with stirring (for example magnetic stirring). Preferably, step 3) of said process is the mixing of solutions A and B by pouring solution A into solution B at room temperature (the pouring may especially be dropwise).

The present invention particularly relates to a process for preparing such a composition, comprising the following steps:

1 ) preparing a solution A by mixing at least one vinylpyrrolidone homopolymer or copolymer and water, especially by simple placing in contact with stirring (for example magnetic stirring) at room temperature (20-25°C), and

2) preparing a solution B by mixing hesperetin in at least one polyol, preferably by heating, especially by heating at a temperature of 40-60°C, preferably at 50°C, for 10 minutes with stirring (for example magnetic stirring); and then

3) mixing solutions A and B, preferably by pouring solution A into solution B at room temperature (the pouring may especially be dropwise).

Steps 1 and 2 of said process may be performed in any order.

Hesperetin is a compound of chemical structure: CH₃

OH O

Hesperetin is also known as · 3',5,7-trihydroxy-4'-methoxyflavanone, or (S)-2,3- dihydro-5,7-dihydroxy-2-(3-hydroxy-4-methoxyphenyl)-4H-1 -benzopyran-4-one (CAS No.: 520-33-2).

Hesperetin is especially available under the trade name Hesperetin Purified® from the company Ferrer Grupo-Exquim (Ferrer), or under the name · FMLT HespeSphere 1 .0® from the company Biospectrum, Inc., or under the name · GFX® from the company Industrial Research Limited, or under the name Jeju Citrus Aglyconoid Liposome® from the company.

Hesperetin (a) may be present in the composition according to the invention in a content ranging from 0.01 % to 10% by weight, more particularly in a content ranging from 0.05% to 5% by weight, relative to the total weight of the composition, preferably ranging from 0.1 % to 2% by weight, and preferentially ranging from 0.50% to 1 % by weight.

Preferably, hesperetin (a) is present in the composition according to the invention in a content of greater than or equal to 0.50% by weight, relative to the total weight of the composition, preferably in a content of greater than or equal to 0.90% by weight, relative to the total weight of the composition, more particularly in a content of 1 .00% by weight.

The composition according to the invention comprises a vinylpyrrolidone homopolymer or copolymer. Among the homopolymers, mention may be made of polyvinylpyrrolidones (PVP) of different molecular weights, the weight-average molecular mass of said homopolymer being measured by light scattering.

More particularly, the polyvinylpyrrolidones (PVP) are chosen from polyvinylpyrrolidones with a weight-average molecular mass ranging from 2000 daltons to 3 000 000 daltons, more particularly with a weight-average molecular mass ranging from 30 000 daltons to 2 000 000 daltons, preferably with a weight-average molecular mass ranging from 40 000 daltons to 1 500 000 daltons. In a preferred embodiment of the invention, said vinylpyrrolidone homopolymer(s) and copolymer(s) present in the composition are chosen from polyvinylpyrrolidone with a weight-average molecular mass ranging from 40 000 daltons to 80 000 daltons and polyvinylpyrrolidone with a weight-average molecular mass ranging from 900 000 daltons to 1 500 000 daltons.

By way of example, a polyvinylpyrrolidone in accordance with the invention is available under the trade name PVP K 30L® from the company ISP.

By way of example, a polyvinylpyrrolidone in accordance with the invention is available under the trade name PVP K 90® from the company ISP (Ashland).

Any type of vinylpyrrolidone copolymer may be used in the composition of the invention. The term "copolymer" means herein both polymers resulting from the polymerization of vinylpyrrolidone with only one type of monomer and those resulting from the polymerization of vinylpyrrolidone with several types of monomers, for example with two types of monomers leading to the production of a terpolymer.

Among the copolymers, mention may be made of polyvinylpyrrolidone/vinyl acetate (PVPA A), polyvinylpyrrolidone/butene; polyvinylpyrrolidone/decene, polyvinylpyrrolidone/hexadecene, polyvinylpyrrolidone/dimethylaminoethyl methacrylate (PVP/DMAEMA), polyvinylpyrrolidone/dimethylaminopropyl(meth)acrylamide, polyvinylpyrrolidone/(meth)acrylic acid/lauryl methacrylate, polyvinylpyrrolidone/vinyl acetate/itaconic acid, polyvinylpyrrolidone/vinyl acetate/vinyl propionate and polyvinylpyrrolidone/vinylcaprolactam/dimethylaminopropylacrylamide/acrylic acid or ester copolymers.

In a particular embodiment according to the invention, the homopolymers and copolymers are chosen from polyvinylpyrrolidones (PVP) and vinylpyrrolidone/vinyl acetate (PVPA A) copolymers.

These copolymers are commercially available, for example under the brand name Luviskol® (PVP and PVPA A) from the company BASF and under the names PVP-K or PVPA/A from the company ISP.

The vinylpyrrolidone homopolymer(s) or copolymer(s) may be present in a content ranging from 0.1 % to 15% by weight, preferably ranging from 1 % to 10% by weight, better still ranging from 3% to 7% by weight and even better still ranging from 5.0% to 7% by weight relative to the total weight of the composition. In a particularly advantageous manner, the vinylpyrrolidone homopolymer(s) or copolymer(s) are present in the composition according to the invention in a content of greater than or equal to 3.0% by weight and preferably in a content of greater than or equal to 5.0% by weight relative to the total weight of the composition.

According to a preferred embodiment, the mass ratio of said vinylpyrrolidone homopolymer(s) and copolymer(s)/hesperetin present in the composition according to the invention is at least equal to 3, for example ranging from 3 to 10 and preferably ranging from 4 to 6.

According to a preferred embodiment, the vinylpyrrolidone homopolymer(s) or copolymer(s) in accordance with the invention is a polyvinylpyrrolidone (PVP), and this said one polyvinylpyrrolidone and hesperetin are present in the composition according to the invention in a polyvinylpyrrolidone/hesperetin mass ratio which is at least equal to 10, preferably at least equal to 20, for example ranging from 10 to 50, preferably ranging from 20 to 40 and better still ranging from 25 to 35.

The composition according to the present invention comprises at least one polyol. According to the invention, the term "polyol" means a hydrocarbon-based chain comprising at least two carbon atoms, preferably from 2 to 50 carbon atoms, preferably from 4 to 20 carbon atoms, preferably containing from 2 to 10 carbon atoms and preferentially containing from 2 to 6 carbon atoms, and bearing at least two hydroxyl groups. The polyols used in the present invention may have a weight-average molecular mass of less than or equal to 1000 and preferably between 90 and 500.

The polyol may be a natural or synthetic polyol. The polyol may have a linear, branched or cyclic molecular structure. The polyol may be chosen from glycerol and derivatives thereof, and glycols and derivatives thereof. The polyol may be chosen from the group consisting of glycerol, diglycerol, polyglycerol, diethylene glycol, propylene glycol, dipropylene glycol, butylene glycol, pentylene glycol, hexylene glycol, 1 ,3-propanediol, 1 ,5-pentanediol, polyethylene glycols, especially containing from 5 to 50 ethylene oxide groups, and sugars such as sorbitol, and a mixture thereof.

More particularly, the polyol may be chosen from the group consisting of dipropylene glycol and butylene glycol, and a mixture thereof. Said polyol(s) may be present in a content ranging from 0.50% to 50% by weight, preferably ranging from 5% to 40% by weight and preferentially ranging from 10% to 30% by weight relative to the total weight of the composition.

The cosmetic composition according to the present invention comprises water.

The amount of water is not limited, and may range from 50% to 99% by weight, preferably from 55% to 95% by weight and more preferably from 70% to 90% by weight relative to the total weight of the composition.

According to one embodiment, said polyol(s) in accordance with the invention and water described previously may be present in the composition according to the invention in a said polyol(s)/water mass ratio which is at least equal to 10, preferably at least equal to 20, for example ranging from 10 to 50 and preferably ranging from 20 to 40.

In a particular embodiment of the invention, the composition according to the invention does not comprise any (or is free of) polyvinyl alcohol. The polyvinyl alcohols according to the invention may be polymers with different degrees of hydrolysis and/or different viscosities. Use may be made in particular of polyvinyl alcohol with a degree of hydrolysis ranging from 74% to 99% and/or with a viscosity ranging from 2.6 to 67 cps (2.6 to 67 mPa.s). As polyvinyl alcohol, an example that may be mentioned is the available under the trade name Celvol 205 PV Alcohol® from the company Sekisui Speciality Chemicals.

The compositions used according to the invention may comprise a physiologically acceptable medium, i.e. a medium that is suitable for the topical administration of a composition, i.e. that is compatible with human keratin materials such as the skin, the scalp, the hair and the nails.

According to the invention, a physiologically acceptable medium is preferentially a cosmetically acceptable medium, that is to say a medium which is free of any unpleasant odor or appearance and which is entirely compatible with the topical administration route.

According to the invention, the term "keratin materials" means the skin, of the body, face and/or area around the eyes, the lips, the nails, mucous membranes, the eyelashes, the eyebrows, bodily hair, the scalp and/or head hair, or any other area of bodily skin. More particularly, the keratin materials according to the invention are the scalp, the hair and/or the skin.

Preferably, the keratin materials according to the invention are the scalp and/or the hair. Preferably, the keratin materials according to the invention are the skin.

The term "skin" means all of the skin of the body, and preferably the skin of the face, neckline, neck, arms and forearms, or even more preferably still the skin of the face, in particular of the forehead, nose, cheeks, chin and area around the eyes.

As specified hereinbelow, hesperetin is advantageously present in the compositions in accordance with the invention in a dissolved form.

By way of example, the composition according to the invention may be intended to be administered topically, i.e. by application at the surface of the keratin material under consideration, such as the skin under consideration. The composition of the invention may be a cosmetic composition (i.e. intended for cosmetic purposes) or a dermatological composition. Preferentially, according to the invention, the composition is a cosmetic composition and even more preferentially a cosmetic composition for topical application.

The term "cosmetic composition" especially means a substance or a preparation intended to be brought into contact with the various superficial parts of the human body, in particular the epidermis, the bodily-hair and head-hair systems, the nails, the lips and the oral mucous membranes, with a view, exclusively or mainly, to cleansing them, making them more attractive, fragrancing them, modifying their appearance, protecting them, keeping them in good condition, or correcting body odors.

The compositions according to the invention may be in the form of aqueous solutions, aqueous-alcoholic solutions, oil-in-water (O/W) emulsions, water-in-oil (W/O) emulsions or multiple emulsions (triple: W/O/W or 0/W/O), or aqueous gels. These compositions are prepared according to the usual methods.

The composition may comprise at least one oil. As oils that may be used, examples that may be mentioned include:

- hydrocarbon-based oils of plant origin, such as liquid triglycerides of fatty acids containing from 4 to 10 carbon atoms, for instance heptanoic or octanoic acid triglycerides, or alternatively, for example, sunflower oil, corn oil, soybean oil, marrow oil, grapeseed oil, sesame seed oil, hazelnut oil, apricot oil, macadamia oil, arara oil, castor oil, avocado oil, caprylic/capric acid triglycerides, for instance those sold by the company Stearineries Dubois or those sold under the names Miglyol 810, 812 and 818 by the company Dynamit Nobel, jojoba oil and shea butter oil;

- synthetic esters and ethers, especially of fatty acids, for instance the oils of formulae R1 COOR2 and R10R2 in which R1 represents a fatty acid residue containing from 8 to 29 carbon atoms and R2 represents a branched or unbranched hydrocarbon-based chain containing from 3 to 30 carbon atoms, for instance Purcellin oil, isononyl isononanoate, isopropyl myristate, 2-ethylhexyl palmitate, 2-octyldodecyl stearate, 2-octyldodecyl erucate or isostearyl isostearate; hydroxylated esters, for instance isostearyl lactate, octyl hydroxystearate, octyldodecyl hydroxystearate, diisostearyl malate or triisocetyl citrate; fatty alcohol heptanoates, octanoates or decanoates; polyol esters, for instance propylene glycol dioctanoate, neopentyl glycol diheptanoate and diethylene glycol diisononanoate; and pentaerythritol esters, for instance pentaerythrityl tetraisostearate;

- linear or branched hydrocarbons of inorganic or synthetic origin, such as volatile or nonvolatile paraffin oils, and derivatives thereof, petroleum jelly, polydecenes, and hydrogenated polyisobutene such as Parleam oil;

- fatty alcohols containing from 8 to 26 carbon atoms, for instance cetyl alcohol, stearyl alcohol and a mixture thereof (cetylstearyl alcohol), octyldodecanol, 2-butyloctanol, 2- hexyldecanol, 2-undecylpentadecanol, oleyl alcohol or linoleyl alcohol;

- silicone oils, for instance volatile or non-volatile polymethylsiloxanes (PDMS) with a linear or cyclic silicone chain, which are liquid or pasty at room temperature, especially cyclopolydimethylsiloxanes (cyclomethicones) such as cyclohexasiloxane; polydimethylsiloxanes comprising alkyl, alkoxy or phenyl groups, which are pendent or at the end of a silicone chain, these groups containing from 2 to 24 carbon atoms; phenylsilicones, for instance phenyl trimethicones, phenyl dimethicones, phenyltrimethylsiloxydiphenylsiloxanes, diphenyl dimethicones, diphenylmethyldiphenyltrisiloxanes or 2-phenylethyl trimethylsiloxy silicates, and polymethylphenylsiloxanes;

- mixtures thereof. In the list of oils mentioned above, the term "hydrocarbon-based oil" means any oil mainly comprising carbon and hydrogen atoms, and possibly ester, ether, fluoro, carboxylic acid and/or alcohol groups.

The composition according to the invention may comprise substances that are solid at room temperature (25°C), for instance fatty acids comprising from 8 to 30 carbon atoms, such as stearic acid, lauric acid, palmitic acid and oleic acid; waxes such as lanolin, beeswax, carnauba wax or candelilla wax, paraffin waxes, microcrystalline waxes, ceresin or ozokerite, and synthetic waxes such as polyethylene waxes and Fischer-Tropsch waxes.

These fatty substances may be chosen in a varied manner by a person skilled in the art so as to prepare a composition having the desired properties, for example in terms of consistency or texture.

According to one particular embodiment of the invention, the composition according to the invention is a water-in-oil (W/O) or oil-in-water (O/W) emulsion. The proportion of the oily phase of the emulsion may range from 5% to 80% by weight and preferably from 5% to 50% by weight relative to the total weight of the composition.

The emulsions generally contain at least one emulsifier chosen especially from amphoteric, anionic, cationic and nonionic emulsifiers, used alone or as a mixture, and optionally a co-emulsifier. The emulsifiers are chosen in an appropriate manner according to the emulsion to be obtained (W/O or O/W emulsion). The emulsifier and the co- emulsifier are generally present in the composition in a proportion ranging from 0.3% to 30% by weight and preferably from 0.5% to 20% by weight relative to the total weight of the composition. For W/O emulsions, examples of emulsifiers that may be mentioned include dimethicone copolyols, such as the mixture of cyclomethicone and dimethicone copolyol sold under the name DC 5225 C by the company Dow Corning, and alkyl methicone copolyols such as the lauryl methicone copolyol sold under the name Dow Corning 5200 Formulation Aid by the company Dow Corning, and the cetyl dimethicone copolyol sold under the name Abil EM 90® by the company Goldschmidt. A crosslinked elastomeric solid organopolysiloxane comprising at least one oxyalkylene group, such as those obtained according to the procedure of Examples 3, 4 and 8 of document US-A-5 412 004 and of the examples of document US-A-5 81 1 487, especially the product of Example 3 (synthesis example) of document US-A-5 412 004, such as the product sold under the reference KSG 21 by the company Shin-Etsu, may also be used as surfactants for W/O emulsions.

For the O/W emulsions, examples of emulsifiers that may be mentioned include nonionic emulsifiers such as oxyalkylenated (more particularly polyoxyethylenated) fatty acid esters of glycerol; oxyalkylenated fatty acid esters of sorbitan; oxyalkylenated (oxyethylenated and/or oxypropylenated) fatty acid esters; oxyalkylenated (oxyethylenated and/or oxypropylenated) fatty alcohol ethers; sugar esters such as sucrose stearate; and mixtures thereof, such as the mixture of glyceryl stearate and PEG-40 stearate. The composition may be an aqueous gel, and may especially comprise common aqueous gelling agents.

In a known manner, the composition according to the invention may also contain adjuvants that are common in cosmetics or dermatology, such as gelling agents, film- forming polymers, preserving agents, fragrances, fillers, UV-screening agents, bactericides, odor absorbers, dyestuffs, plant extracts, cosmetic and dermatological active agents, and salts. The amounts of these various adjuvants are those conventionally used in the field under consideration, for example from 0.01 % to 20% of the total weight of the composition.

A further subject of the invention is a cosmetic process for treating keratin materials, comprising the application to the keratin materials, especially the skin, or the oral administration to an individual, of a composition as described previously.

Said cosmetic treatment process is non-therapeutic.

More particularly, a subject of the invention is also a cosmetic treatment process for caring for, making up and/or cleansing keratin materials, especially the skin, comprising the application to said keratin materials, especially the skin, of a composition according to the invention as described previously.

Said cosmetic treatment process for caring for, making up and/or cleansing the skin is non-therapeutic. More particularly, a subject of the invention is also a cosmetic process for preventing and/or treating the signs of aging of the skin, comprising at least one step of topical application to the keratin materials, such as the skin, of a composition according to the invention as described previously.

The signs of aging of the skin to be prevented and/or treated in the cosmetic process according to the invention may be chosen from wrinkles and fine lines, and/or for combating wizened, flaccid and/or thinned skin.

A subject of the present invention is also the cosmetic use of a composition according to the invention as defined previously, for caring for, making up and/or cleansing keratin materials.

More particularly, a subject of the invention is the cosmetic use of a composition as defined previously for caring for the skin, preferably for preventing and/or treating the signs of aging of the skin. In another embodiment, the invention relates to a cosmetic treatment process for caring for, making up and/or cleansing keratin materials, especially the skin, comprising the oral administration, to an individual, of a composition as defined previously.

In another embodiment, the invention also relates to the cosmetic use as defined previously, in which the combination of hesperetin and of at least one organic solvent as defined previously, or the composition comprising it, is used in a food supplement.

The expressions "between... and..." and "ranging from... to..." or "at least..." or "at the least..." should be understood as being limits included, unless otherwise specified.

The examples below of compositions according to the invention are given as illustrations with no limiting nature. The compounds are indicated as their chemical name or their INCI name.

The amounts of the ingredients are expressed as weight percentages.

Example 1 : Evaluation of the stability of the formulations

Preparation process:

The polymer (vinylpyrrolidone homopolymer (PVP)) is mixed in water by simple placing in contact with magnetic stirring at room temperature. The solution of hesperetin in its solvents (polyols) is then prepared, by heating at 50°C for 10 minutes with magnetic stirring. The solution of polymer in water at room temperature is poured therein.

Evaluation protocol:

The stability of the preparation obtained, stored at 4°C and at room temperature, is evaluated after 24 hours by macroscopic monitoring with the eye (observation of cloudiness or a deposit, if any), and by observation with a microscope under polarized light (presence or absence of crystals).

The following results were obtained for hesperetin with various evaluated combinations:

It was thus found, unexpectedly, that the aqueous composition 1 in accordance with the invention, comprising hesperetin at 1 % by weight, combined with a vinylpyrrolidone homopolymer (PVP) present in a content of 5% by weight, and also with polyols (dipropylene glycol and butylene glycol) in a total amount of 20.8% by weight, is stable at room temperature and at 4°C, and does not show any recrystallization of the hesperetin; the hesperetin is thus very well solubilized in this particular combination.

Example 2: Evaluation of the stability of the formulations

Preparation process:

Polymers (PVP or PVA) are mixed in water by simple placing in contact with magnetic stirring at room temperature. The solution of hesperetin in its solvents (polyols) is then prepared, by heating at 50°C for 10 minutes with magnetic stirring. The solution of polymer in water at room temperature is poured therein.

Evaluation protocol:

The stability of the preparation obtained, stored at 4°C and at room temperature (RT), is evaluated after 24 hours by macroscopic monitoring with the eye (observation of cloudiness or a deposit, if any), and by observation with a microscope under polarized light (presence or absence of crystals).

The following results were obtained for the combination of hesperetin with various evaluated polymers:

Ingredients in weight % Composition 2 in Composition 4 in Comparative relative to the total weight accordance with accordance with Example E of the composition the invention the invention

Hesperetin (Hesperetin 1 1 1

Purified^® from Ferrer Grupo)

Dipropylene glycol 20 20 20

(Dipropylene glycol LO+^®

from Dow Chemical)

Butylene glycol (1,2- 8.8 8.8 8.8

Propylene glycol Care^® from BASF)

Vinylpyrrolidone polymer

5 0 0

(PVP) with a weight-average

molecular mass ranging

from 40 000 daltons to 80

000 daltons (PVP K 30L^®

from ISP)

Vinylpyrrolidone polymer 0 5 0

(PVP) with a weight-average

molecular mass ranging

from 900 000 daltons to 1

500 000 daltons (PVP K 90^®

from ISP (Ashland))

Polyvinyl alcohol or PVA 0 0 5

(Celvol 205 PV Alcohol^®

from Sekisui Speciality

Chemicals)

Water 65.2 65.2 65.2

Evaluation of the stability Stability with Stability with Immediate

respect to respect to reprecipitation of recrystallization of recrystallization of the hesperetin the active agent the active agent at

at RT or at 4°C RT or at 4°C

(overnight) (overnight)

It was thus found that comparative composition E, comprising hesperetin at 1 % by weight, combined with a polymer which is polyvinyl alcohol (PVA) present in a content of 5% by weight, and also with polyols (dipropylene glycol and butylene glycol) in a total amount of 20.8% by weight, is not stable at room temperature and at 4°C, and does not show any recrystallization of the hesperetin.

It was thus found, unexpectedly, that the aqueous compositions 2 and 4 in accordance with the invention, comprising hesperetin at 1 % by weight, combined with various vinylpyrrolidone homopolymers (PVP) having different weight-average molecular masses, present in a content of 5% by weight, and also with polyols (dipropylene glycol and butylene glycol) in a total amount of 20.8% by weight, are stable at room temperature and at 4°C, and do not show any recrystallization of the hesperetin; the hesperetin is thus very well solubilized in these combinations in accordance with the invention.

Example 3: Composition according to the invention

A skincare composition(oil-in-water emulsion) having the following composition prepared:

Procedure:

Phase A was heated at between 80°C and 85°C until all the fatty substances had fully melted (about 85°C). Phase B was heated at 85°C. Phase A was rapidly added to phase B with very vigorous stirring for 10 minutes. The emulsion was cooled with slow stirring.

Phases C to D were added after cooling to room temperature. Phase E1 was prepared with stirring using a magnetic bar and added at the end of the preparation.

The composition is stable and homogeneous after storage for 2 months at 45°C.

This composition may be applied regularly to facial skin in order to attenuate the signs of aging of the skin.

Claims

1 . A composition comprising:

- hesperetin;

- at least one polyol;

- at least one vinylpyrrolidone homopolymer or copolymer;

- water.

2. The composition as claimed in the preceding claim, characterized in that hesperetin is present in a content of greater than or equal to 0.50% by weight, relative to the total weight of the composition, preferably in a content of greater than or equal to 0.90% by weight, relative to the total weight of the composition, more particularly in a content of 1 .00% by weight.

3. The composition as claimed in claim 1 , characterized in that hesperetin is present in a content ranging from 0.05% to 5% by weight, relative to the total weight of the composition, preferably ranging from 0.1 % to 2% by weight, and preferentially ranging from 0.50% to 1 % by weight.

4. The composition as claimed in any one of the preceding claims, characterized in that said polyol(s) are chosen from glycerol, diglycerol, polyglycerol, propylene glycol, butylene glycol, pentylene glycol, hexylene glycol, dipropylene glycol, diethylene glycol, 1 ,3-propanediol, 1 ,5-pentanediol, polyethylene glycols, and sugars such as sorbitol, and a mixture thereof.

5. The composition as claimed in any one of the preceding claims, characterized in that said polyol(s) are chosen from dipropylene glycol and butylene glycol, and a mixture thereof.

6. The composition as claimed in any one of the preceding claims, characterized in that said polyol(s) are present in a content ranging from 0.50% to 50% by weight, preferably ranging from 5% to 40% by weight and preferentially ranging from 10% to 30% by weight relative to the total weight of the composition.

7. The composition as claimed in any one of the preceding claims, characterized in that the vinylpyrrolidone homopolymers and copolymers are chosen from polyvinylpyrrolidones

(PVP), polyvinylpyrrolidones complexed with iodine, polyvinylpyrrolidone/vinyl acetate (PVPA A), polyvinylpyrrolidone/butene; polyvinylpyrrolidone/decene, polyvinylpyrrolidone/hexadecene, polyvinylpyrrolidone/dimethylaminoethyl methacrylate (PVP/DMAEMA), polyvinylpyrrolidone/dimethylaminopropyl(meth)acrylamide, polyvinylpyrrolidone/(meth)acrylic acid/lauryl methacrylate, polyvinylpyrrolidone/vinyl acetate/itaconic acid, polyvinylpyrrolidone/vinyl acetate/vinyl propionate and polyvinylpyrrolidone/vinylcaprolactam/dimethylaminopropylacrylamide/acrylic acid or ester copolymers.

8. The composition as claimed in any one of the preceding claims, characterized in that the vinylpyrrolidone homopolymers and copolymers are chosen from polyvinylpyrrolidones, preferably chosen from polyvinylpyrrolidones with a weight-average molecular mass ranging from 40 000 daltons to 1 500 000 daltons, particularly chosen from a polyvinylpyrrolidone with a weight-average molecular mass ranging from 40 000 daltons to 80 000 daltons and a polyvinylpyrrolidone with a weight-average molecular mass ranging from 900 000 daltons to 1 500 000 daltons.

9. The composition as claimed in any one of the preceding claims, characterized in that the vinylpyrrolidone homopolymer(s) or copolymer(s) are present in a content range from 0.1 % to 15% by weight, preferably ranging from 1 % to 10% by weight, better still ranging from 3% to 7% by weight, relative to the total weight of the composition, and is preferably greater than or equal to 5.0% by weight relative to the total weight of the composition.

10. The composition as claimed in any one of the preceding claims, in which the mass ratio of said vinylpyrrolidone homopolymer(s) and copolymer(s)/hesperetin is at least equal to 3, for example ranging from 3 to 10 and preferably ranging from 4 to 6.

1 1. The composition as claimed in any one of the preceding claims, in which the mass ratio of said polyol(s)/water is at least equal to 10, preferably at least equal to 20, for example ranging from 10 to 50 and preferably ranging from 20 to 40.

12. The composition as claimed in any one of the preceding claims, characterized in that it is in the form of a water-in-oil or oil-in-water emulsion, preferably an oil-in-water emulsion.

13. The composition as claimed in any one of the preceding claims, characterized in that it is a cosmetic composition.

14. A cosmetic process for treating keratin materials, comprising the application to the keratin materials, such as the skin, of a composition as claimed in any one of the preceding claims.

15. A cosmetic treatment process for caring for and/or making up and/or cleansing keratin materials, especially the skin, comprising the application to said keratin materials, especially the skin, of a composition as defined in any one of claims 1 to 10.