WO2016102402A1

WO2016102402A1 - Aqueous composition comprising a 4-(heterocycloalkyl)-benzene-1,3-diol compound, a c2-c4 monoalcohol, and a glycol

Info

Publication number: WO2016102402A1
Application number: PCT/EP2015/080652
Authority: WO
Inventors: Marie-Lise CHIRON; Véronique Chevalier
Original assignee: L'oreal
Priority date: 2014-12-22
Filing date: 2015-12-18
Publication date: 2016-06-30
Also published as: FR3030252B1; FR3030252A1

Abstract

The invention relates to a composition comprising: at least one 4-(heterocycloalkyl)-benzene-1,3-diol compound of formula (I); at least one C2-C4 monoalcohol; at least one glycol; and water. The invention also relates to the use of the composition for making-up, caring for and/or cleaning keratin materials, in particular the skin.

Description

An aqueous composition comprising a 4- (heterocycloalkyl) -benzene-1,3-diol compound, a C2-C4 monoalcohol and a glycol

The subject of the present invention is a composition, preferably a cosmetic composition, comprising a 4- (heterocycloalkyl) -benzene-1,3-diol compound, at least one C2-C4 monoalcohol and at least one glycol.

The 4- (heterocycloalkyl) -benzene-1,3-diol derivatives are compounds used for the treatment of cutaneous signs of aging and more particularly as a depigmenting agent for keratin materials.

However, these compounds which are in solid form at room temperature and have a high melting point (> 210 ° C) are difficult to solubilize. They are notably poorly soluble in water and glycerine.

However, it is necessary for this compound to be formulated in a solubilized form, and in particular at a high content, such as greater than or equal to 0.20% by weight, in order to make the best use of its activity and it is also preferable that its solubilization is maintained over time to avoid any recrystallization phenomenon during the storage of compositions comprising such a compound.

In fact the solubilized forms lead to a better bioavailability in the skin than crystallized forms whose crystal size is poorly controlled.

For the purposes of this application, the term "bioavailability" refers to the molecular penetration of the active agent into the living layers of the skin and in particular of the epidermis. It will be sought that the penetrated concentration is as high as possible, so as to increase the rate of asset reaching the living layers of the skin.

By "solubilized form" is meant a dispersion of the derivatives according to the invention in a liquid, in the free molecular state, in particular in uncomplexed form. No crystallization of 4- (heterocycloalkyl) -benzene-1,3-diol derivatives is visible to the naked eye or in cross-polarized light microscopy.

It is therefore sought to increase the solubility of these active ingredients but using limited amounts of solvents which reduces the cosmetic properties of the compositions. Compositions containing a high level of glycols provide a tacky and greasy feel of the skin.

The object of the present invention is precisely to propose a new galenic formulation of the 4- (heterocycloalkyl) -benzene-1,3-diol compounds making it possible to overcome the abovementioned disadvantages, and thus to incorporate these compounds in a form solubilized and durable over time, these compounds being in particular present at a high content. This new galenic formulation of the compounds 4- (heterocycloalkyl) -benzene-1,3-diol makes it possible in particular to improve the efficacy of the active ingredient for the treatment of keratin materials such as the skin. The compositions according to the invention make it possible to use lower amounts of glycols.

The inventors have in fact unexpectedly discovered that the combination of at least one 4- (heterocycloalkyl) -benzene-1,3-diol compound with at least one glycol and at least one C2-C4 monoalcohol makes it possible to solubilize this compound while avoiding recrystallization, especially after storage for 1 month at room temperature (25 ° C) and / or at 4 ° C and / or 45 ° C.

More specifically, the subject of the invention is a composition, in particular a cosmetic composition, comprising a composition comprising;

a) at least one glycol;

b) at least one C2-C4 monoalcohol;

c) water;

d) at least one 4- (heterocycloalkyl) -benzene-1,3-diol compound of general formula (I) 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 at least one C2-C4 monoalcohol and water, and

2) preparing a solution B by mixing at least one 4- (heterocycloalkyl) -benzene-1,3-diol compound in at least one glycol, and

3) mixing solutions A and B

Preferably step 1) of said process is the preparation of a solution A by mixing at least one C2-C4 monoalcohol and water by simply contacting 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 at least one 4- (heterocycloalkyl) -benzene-1,3-diol compound in at least one glycol by heating, in particular by heating at a temperature of 40-60 ° C, preferably at 50 ° C, for 10 minutes with stirring (eg magnetic). Preferably step 3) of said process is the mixing of solutions A and B by pouring solution A on solution B at room temperature (the pouring may be in particular drop by drop). In particular, the present invention relates to a process for preparing such a composition comprising the following steps:

1) preparation of a solution A by mixing at least one C2-C4 monoalcohol and water, in particular by simple contacting with stirring (for example magnetic stirring) at room temperature (20-25 ° C. ), and

2) preparing a solution B by mixing at least one 4- (heterocycloalkyl) -benzene-1,3-diol compound in at least one glycol, preferably by heating, in particular by heating to a temperature of 40- 60 ° C, preferably at 50 ° C, for 10 minutes with stirring (for example magnetic); then

3) mixing solutions A and B, preferably by pouring solution A on solution B at room temperature (the pouring may be in particular drop by drop).

Steps 1 and 2 of said method can be implemented in any order.

The 4- (heterocycloalkyl) -benzene-1,3-diol compounds according to the invention have the following general formula (I):

in which

R1, R2, R3, R4, which may be identical or different, represent:

- a hydrogen

a C1-C4 alkyl radical

a hydroxymethyl, a hydroxyethyl,

a C1-C4 alkoxycarbonyl,

a C1-C4 alkoxy,

- a hydroxyl R1 and R2 are interconnected and form a carbon ring with 5 or 6 carbon atoms with the carbon atom to which they are bonded and R3 and R4, identical or different, represent:

- a hydrogen

a C1-C4 alkyl radical

or

R1 and R4 are connected together and form a chain - (CH2) ₂ - or - (CH2) ₃ - and R2 and R3, which are identical or different, represent:

- a hydrogen

a C1-C4 alkyl radical

X represents an oxygen atom, or a sulfur atom.

Y represents a hydrogen, a chlorine atom or a fluorine atom.

m can take the values 1 or 2 and n can take the values 0 or 1 and when n = 0, then m = 1 or 2, and when n = 1, then m = 1. as well as the salts of the compounds of general formula (I), and their isomeric and enantiomeric forms.

Among the salts of the compounds of general formula (I), there may be mentioned preferably salts with an organic base or with an inorganic base.

Suitable inorganic bases are, for example, potassium hydroxide, sodium hydroxide or calcium hydroxide.

Suitable organic bases are, for example, morpholine, piperazine, arginine, lysine.

The compounds of general formula (I) may also exist in the form of hydrates or solvates.

Suitable solvents for forming solvates are, for example, alcohols such as ethanol or iso-propanol.

According to the present invention, the term C1-C4 alkyl denotes a saturated hydrocarbon chain, linear or branched, comprising from 1 to 4 carbon atoms.

According to the present invention, C1-C4 alkyloxycarbonyl denotes a carboxy radical substituted with an alkyl radical containing from 1 to 4 carbon atoms. According to the present invention, C1-C4 alkoxy denotes an oxygen atom substituted by a linear or branched saturated hydrocarbon-based chain containing from 1 to 4 carbon atoms. According to the present invention, the isomers are the cis and trans forms relating to the substituents on the heterocycloalkyl at the 4-position of benzene-1,3-diol.

According to the present invention, the compounds of general formula (I) that are particularly preferred are those for which:

R1 represents a hydrogen, a C1-C4 alkyl radical or a hydroxymethyl radical,

R2 represents a hydrogen,

R3 represents a hydrogen,

R4 represents a hydrogen,

X represents an oxygen atom

Y represents a hydrogen or a fluorine atom

m = 1 and n = 1, as well as the salts of these compounds of general formula (I), and their isomeric and enantiomeric forms.

Among the compounds of formula (I) falling within the scope of the present invention, mention may be made in particular of the following:

1: 4- (tetrahydro-pyran-4-yl) benzene-1,3-diol

2: 4- (tetrahydro-thiopyran-4-yl) -benzene-1,3-diol

3: 4- (cis-2,6-Dimethyl-tetrahydro-pyran-4-yl) -benzene-1,3-diol

4: trans-4- (2-methyl-tetrahydro-pyran-4-yl) -benzene-1,3-diol

5: cis-4- (2-methyl-tetrahydro-pyran-4-yl) -benzene-1,3-diol

6: trans-4- (2-Ethyl-tetrahydro-pyran-4-yl) -benzene-1,3-diol

7: cis-4- (2-Ethyl-tetrahydro-pyran-4-yl) -benzene-1,3-diol

8: trans-4- (2-Hydroxymethyl-tetrahydro-pyran-4-yl) -benzene-1,3-diol

9: 4- (2,2,6,6-tetramethyltetrahydro-pyran-4-yl) benzene-1,3-diol

10: 4- (tetrahydro-furan-3-yl) -benzene-1,3-diol

1: 4- (tetrahydro-thiophen-3-yl) -benzene-1,3-diol

12: 4- (6-Oxa-spiro [4.5] dec-9-yl) -benzene-1,3-diol

13: 4-Chloro-6- (tetrahydro-pyran-4-yl) -benzene-1,3-diol

14: 4-Fluoro-6- (tetrahydro-pyran-4-yl) -benzene-1,3-diol

15: 4- (2,2-Diethyl-tetrahydro-pyran-4-yl) -benzene-1,3-diol

16: 4- (tetrahydro-pyran-3-yl) -benzene-1,3-diol

17: trans-4- (5-Hydroxymethyl-tetrahydro-furan-3-yl) -benzene-1,3-diol 18: cis-4- (5-Hydroxymethyl-tetrahydro-furan-3-yl) -benzene-1,3-diol

19: trans-4-Fluoro-6- (5-hydroxymethyl-tetrahydro-furan-3-yl) -benzene-1,3-diol

20: cis-4-Fluoro-6- (5-hydroxymethyl-tetrahydro-furan-3-yl) -benzene-1,3-diol

21: trans-4-Fluoro-6- (2-hydroxymethyl-tetrahydro-pyran-4-yl) -benzene-1,3-diol

22: cis-4-Fluoro-6- (2-hydroxymethyl-tetrahydro-pyran-4-yl) -benzene-1,3-diol

23: cis-4- (8-Oxa-bicyclo [3.2.1] oct-3-yl) -benzene-1,3-diol

24: trans-4- (8-Oxa-bicyclo [3.2.1] oct-3-yl) -benzene-1,3-diol

25: 4-Fluoro-6- (tetrahydro-thiopyran-4-yl) -benzene-1,3-diol These compounds may be prepared according to the procedures described in application WO2010063773.

The compound 4- (tetrahydro-pyran-4-yl) -benzene-1,3-diol is particularly preferred.

compound 1

The compound (d) of formula (I) may be present in the composition according to the invention, in a content ranging from 0.001% to 10% by weight, relative to the total weight of the composition, more particularly in a content ranging from From 0.05% to 5% by weight, and preferably from 0.1% to 3% by weight, and preferably ranging from 0.25% to 2% by weight.

The composition according to the invention comprises at least one C2-C4 monoalcohol.

C2-C4 monoalcohols comprise a hydroxy group and 2 to 4 carbon atoms. Ethanol, propanol, isopropanol, butanol-1, isobutanol and mixtures thereof can be used. The C2-C4 monoalcohol is preferably ethanol.

The concentration of C2-C4 monoalcohol can range from 0.1% to 30% by weight, preferably from 0.5% to 15% by weight, preferably from 1% to 10% by weight relative to the total weight of the composition.

According to a preferred embodiment, the weight ratio C 2 -C 4 monohydric alcohol / compound d) of formula (I) present in the composition according to the invention ranges from 1 to 20, preferably from 1.5 to 10. The composition according to The present invention comprises at least one glycol. By glycol according to the invention is meant a hydrocarbon chain comprising at least 2 carbon atoms, preferably 2 to 50 carbon atoms, preferably 2 to 20 carbon atoms, preferably having 2 to 10 carbon atoms, and preferably having from 2 to 6 carbon atoms, and bearing two hydroxyl groups. The glycols used in the present invention may have a weight average molecular weight less than or equal to 1000, preferably between 60 and 500.

The glycol may be a natural or synthetic glycol. The glycol may have a linear, branched or cyclic structure.

The glycol may be chosen from diethylene glycol, propylene glycol, dipropylene glycol, butylene glycol, pentylene glycol, hexylene glycol, 1,3-propanediol, 1,5-pentanediol and polyethylene glycol, in particular having 5 to 50 ethylene oxide groups, and mixtures thereof.

More particularly, the glycol may be chosen from the group consisting of dipropylene glycol, propylene glycol, propanediol-1, 3, butylene glycol, and their mixture, and more particularly dipropylene glycol.

The said glycol (s) may be present in a content ranging from 0.5% to 60% by weight, relative to the total weight of the composition, preferably ranging from 5% to 50% by weight. % by weight, and preferably ranging from 10% to 40% by weight, relative to the total weight of the composition.

The cosmetic composition according to the present invention comprises water.

In a preferred embodiment, the amount of water in the composition according to the invention is greater than or equal to 20% by weight, preferably greater than or equal to 50% by weight, and more particularly greater than or equal to 70% by weight. weight relative to the total weight of the composition.

According to one embodiment, the said glycol (s) in accordance with the invention and the water described above may be present in the composition according to the invention in a mass ratio of the said glycol (s) / water, for example ranging from 0.1 to 10, and preferably ranging from 0.3 to 1.5.

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

According to the invention a physiologically acceptable medium is preferably a cosmetically acceptable medium, that is to say without odor, or unpleasant appearance, and which is perfectly compatible with the topical route of administration.

The term "keratin materials" according to the invention is understood to mean the skin, the body, the face and / or the contour of the eyes, the lips, the nails, the mucous membranes, the eyelashes, the eyebrows, the hairs, the scalp and / or the hair, or any other skin area of the body. 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 is the skin.

By "skin" is meant all of the skin of the body, and preferably, the skin of the face, décolleté, neck, arms and forearms, or even more preferably, the skin of the skin. face, including forehead, nose, cheeks, chin, eye area.

As specified below, the compound of formula (I) is advantageously present in the compositions according to the invention in a solubilized form.

By way of example, the composition according to the invention may be intended to be administered topically, that is to say by surface application of the keratin material in question, such as the skin under consideration.

The composition of the invention may be a cosmetic composition (either intended for cosmetic use) or dermatological. Preferably, according to the invention, the composition is a cosmetic composition and even more preferentially a cosmetic composition for topical application.

The term "cosmetic composition" is understood to mean 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 hair and hair systems, the nails, the lips and the oral mucosa, in particular view, exclusively or mainly, to clean, embellish, perfume, change the appearance, protect, maintain or repair body odors.

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

The composition may comprise at least one oil. As usable oils, there may be mentioned for example:

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

esters and synthetic ethers, in particular of fatty acids, such as the oils of formulas R 1 COOR 2 and R 10 R 2 in which R 1 represents the residue of a fatty acid comprising from 8 to 29 carbon atoms, and R 2 represents a hydrocarbon-based chain , branched or unbranched, containing from 3 to 30 carbon atoms, for example purcellin oil, isononyl isononanoate, isopropyl myristate, 2-ethylhexyl palmitate, stearate of octyl-2-dodecyl, octyl-2-dodecyl erucate, isostearyl isostearate; hydroxylated esters such as isostearyl lactate, octyl hydroxystearate, octyldodecyl hydroxystearate, diisostearyl malate, triisocetyl citrate; heptanoates, octanoates, decanoates of fatty alcohols; polyol esters, such as propylene glycol dioctanoate, neopentyl glycol diheptanoate and diethylene glycol diisononanoate; and pentaerythritol esters such as pentaerythrityl tetraisostearate;

linear or branched hydrocarbons of mineral or synthetic origin, such as paraffin oils, volatile or not, and their derivatives, petroleum jelly, polydecenes, hydrogenated polyisobutene such as parleam oil;

fatty alcohols having from 8 to 26 carbon atoms, such as cetyl alcohol, stearyl alcohol and their mixture (cetylstearyl alcohol), octyldodecanol, 2-butyloctanol,

2-hexyldecanol, 2-undecylpentadecanol, oleic alcohol or linoleic alcohol;

silicone oils such as volatile or non-volatile polymethylsiloxanes (PDMS) with a linear or cyclic silicone chain, which are liquid or pasty at room temperature, in particular cyclopolydimethylsiloxanes (cyclomethicones) such as cyclohexasiloxane; polydimethylsiloxanes comprising alkyl, alkoxy or phenyl groups, during or at the end of the silicone chain, groups having from 2 to 24 carbon atoms; phenyl silicones such as phenyltrimethicones, phenyldimethicones, phenyltrimethylsiloxydiphenylsiloxanes, diphenyl dimethicones, diphenylmethyldiphenyl trisiloxanes, 2-phenylethyltrimethylsiloxysilicates, and polymethylphenylsiloxanes;

- their mixtures. The term "hydrocarbon-based oil" in the list of oils mentioned above, any oil predominantly comprising carbon and hydrogen atoms, and optionally ester, ether, fluoro, carboxylic acid and / or alcohol groups.

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

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

According to a 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 1% 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, especially chosen from amphoteric, anionic, cationic or nonionic emulsifiers, used alone or as a mixture, and optionally a co-emulsifier. The emulsifiers are suitably selected according to the emulsion to be obtained (W / O or O / W). 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 the 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 Dow Corning, and alkyl dimethicone copolyols such as Laurylmethicone copolyol sold under the name "Dow Corning 5200 Formulation Aid" by the company Dow Corning and Cetyl dimethicone copolyol sold under the name "Abil EM 90®" by the company Goldschmidt. For O / W emulsions, mention may be made, for example, as emulsifiers, of nonionic emulsifiers such as oxyalkylenated (more particularly polyoxyethylenated) fatty acid esters of glycerol; oxyalkylenated fatty acid and sorbitan esters; oxyalkylenated fatty acid esters (oxyethylenated and / or oxypropylenated); oxyalkylenated fatty alcohol ethers (oxyethylenated and / or oxypropylenated); sugar esters such as sucrose stearate; and mixtures thereof such as the mixture of glyceryl stearate and PEG-100 stearate.

The composition may be an aqueous gel, and in particular comprise conventional aqueous gelling agents.

In a known manner, the composition according to the invention may also contain adjuvants which are customary in the cosmetic or dermatological field, such as gelling agents, thickeners, film-forming polymers, preservatives, perfumes, fillers, UV filters, bactericidal agents, odor absorbers, dyestuffs, plant extracts, vitamins, polyols such as glycerin, diglycerin, sugars such as sorbitol, cosmetic and dermatological active ingredients, and salts. The amounts of these various adjuvants are those conventionally used in the field under consideration, and for example from 0.001 to 20% of the total weight of the composition.

According to the invention the composition further comprises glycerine. The concentration of glycerine may range from 0.1% to 60% by weight, preferably from 1% to 50% by weight, preferably from 5% to 30% by weight relative to the total weight of the composition.

Advantageously, the composition according to the invention has a pH ranging from 3 to 7. Preferably, the pH of the composition ranges from 4 to 6.

More particularly, the subject of the invention is also a process for the cosmetic treatment of skincare, makeup, and / or cleaning of keratinous substances, in particular the skin, comprising the application on said keratin materials, in particular the skin, of a composition according to the invention as described above.

Said method of cosmetic treatment of care, makeup, and / or cleansing of the skin is non-therapeutic.

The subject of the invention is also a cosmetic process for the depigmentation, lightening and / or bleaching of keratin materials, in particular human skin, hair or hair, comprising the application to said keratin materials of a composition according to the invention. invention as described above.

The invention also relates to a cosmetic method for preventing and / or treating cutaneous signs of aging, comprising at least one application step topically on keratin materials, such as the skin, of a composition according to the invention as described above.

The cutaneous signs of the aging to be prevented and / or treated in the cosmetic process according to the invention may be chosen from the lines and wrinkles, and / or to fight against the skin withered, soft and / or thinned.

The invention also relates to the cosmetic use of a composition according to the invention as defined above, for the care, makeup and / or cleaning of keratin materials.

In another embodiment, the invention relates to a cosmetic treatment method for the care, makeup, and / or cleaning of keratinous substances, in particular the skin, comprising the administration, topically, to an individual, of a composition as defined above.

The expressions "between ... and ..." and "from ... to ...", or "at least ..", or "at least .." must be understood as inclusive, unless the opposite is specified. The following examples of compositions according to the invention are given by way of illustration and without limitation. The compounds are indicated in chemical name or INCI name.

The contents of the ingredients are expressed in percentage by weight.

Example 1: Evaluation of the stability of formulations

Method of preparation :

The solution of compound 1 in the glycols is prepared for 10 minutes with magnetic stirring. Water and glycerin and ethanol are then added at room temperature.

Evaluation Protocol:

The stability of the obtained preparation stored at 4 ° C. and at room temperature after 24 hours is evaluated by a macroscopic examination with the eye (observation or not of a cloudiness or a deposit) and by observation under a microscope under a light. polarized (presence or absence of crystals).

The following results were obtained with different associations evaluated: Compo 1 Compo 2 Compo 1A Compo 1 B comparative comparative invention

Compound 1 1, 5 1, 5 1, 5 1, 5

Dipropylene 15 22.5 15 30 glycol

Propylene glycol 3.75 7.5 7.5 3.75

Butylene glycol 1 1, 25 7.5 15 3.75

Ethanol 0 0 8 5.33

Glycerin 8 8 8 8

Water QSP 100% QSP 100% QSP 100% QSP 100%

Total amount 30% 37.5% 37.5% 37.5% glycols

Stability We observe We observe no steps

immediately immediately crystals crystals

one after 2 months after crystallization crystallization at 4 ° C and at 4 ° C of the compound 1 temperature compound and at

1 ambient room temperature

It has thus been found that, unexpectedly, compositions 1A and 1B in accordance with the invention are stable at room temperature and at 4 ° C., and show no recrystallization of compound 1, this resorcinol derivative is therefore very well solubilized in these particular associations.

Examples 2 to 4

The following compositions were prepared

Composition in% MA 2 3 4

Compound 1 1 0.5 1, 3

Dipropylene glycol 12 15 15

Butylene glycol 10

Propylene glycol 5

Glycerin 5 5 10

Disodium EDTA 0.2

Caprylyl glycol 0.2 0.2 0.2 phenoxyethanol

0.4 0.4 0.4

Polysorbate 60 0.7 0.7 0.7

Stearic acid 0.5 0.5 0.5

GLYCERYL STEARATE (and)

PEG-100 STEARATE (ARLACEL® 1, 6 1, 6 1, 6 165 FL from Uniqema)

Octyl dodecanol 1 1 1

Tocopherol 0.1

Cetyl alcohol 1 1 1

Isoparaffin (Parleam of NOF) 1 1 1

0.2 0.2 0.2 xanthan gum

Cyclohexasiloxane 1 1 1 1 1 1 1

Crosslinked homopolymer of acid

acrylamidomethyl propane

sulfonic acid partially neutralized to 2 2 2 ammonia (Hostacerin AMPS ^®

from Clariant)

Water QSP 100% QSP 100% QSP 100%

Ethanol 5 5

10

Stability No No Crystal Paste after crystals after crystals 2 months at 4 ° C 2 months at 4 ° C after 2 months and at and at 4 ° C and at room temperature ambient temperature

These compositions can be applied regularly to the skin of the face to reduce the signs of skin aging.

Claims

1. Composition comprising:

a) at least one glycol;

b) at least one C2-C4 monoalcohol;

c) water;

d) at least one 4- (heterocycloalkyl) -benzene-1,3-diol compound of the following general formula (I):

in which

R1, R2, R3, R4, which may be identical or different, represent:

a hydrogen,

a C1-C4 alkyl radical,

a hydroxymethyl, a hydroxyethyl,

a C1-C4 alkoxycarbonyl,

a C1-C4 alkoxy,

a hydroxyl,

or

R1 and R2 are interconnected and form a carbon ring with 5 or 6 carbon atoms with the carbon atom to which they are bonded and R3 and R4, identical or different, represent:

- a hydrogen

a C1-C4 alkyl radical

or

R1 and R4 are connected together and form a chain (CH2) ₂ - or - (CH2) ₃ - and R2 and R3, which may be identical or different, represent:

- a hydrogen

a C1-C4 alkyl radical

X represents an oxygen atom, or a sulfur atom.

Y represents a hydrogen, a chlorine atom or a fluorine atom. m can take the values 1 or 2 and n can take the values 0 or 1 and when n = 0, then m = 1 or 2, and when n = 1, then m = 1.

as well as the salts of the compounds of general formula (I), and their isomeric and enantiomeric forms, hydrates and solvates.

2 - Composition according to claim 1 characterized in that in the compound d) of formula (I):

R1 represents a hydrogen, a C1-C4 alkyl radical or a hydroxymethyl radical,

R2 represents a hydrogen,

R3 represents a hydrogen,

R4 represents a hydrogen,

X represents an oxygen atom

Y represents a hydrogen or a fluorine atom

- m = 1 and n = 1,

as well as the salts of these compounds and their isomeric and enantiomeric forms, hydrates and solvates.

3 - Composition according to one of claims 1 to 2 characterized in that the compound (s) of formula (I) are chosen from the group consisting of:

1: 4- (tetrahydro-pyran-4-yl) benzene-1,3-diol

2: 4- (tetrahydro-thiopyran-4-yl) -benzene-1,3-diol

3: 4- (cis-2,6-Dimethyl-tetrahydro-pyran-4-yl) -benzene-1,3-diol

4: trans-4- (2-methyl-tetrahydro-pyran-4-yl) -benzene-1,3-diol

5: cis-4- (2-methyl-tetrahydro-pyran-4-yl) -benzene-1,3-diol

6: trans-4- (2-Ethyl-tetrahydro-pyran-4-yl) -benzene-1,3-diol

7: cis-4- (2-Ethyl-tetrahydro-pyran-4-yl) -benzene-1,3-diol

8: trans-4- (2-Hydroxymethyl-tetrahydro-pyran-4-yl) -benzene-1,3-diol

9: 4- (2,2,6,6-tetramethyltetrahydro-pyran-4-yl) benzene-1,3-diol

10: 4- (tetrahydro-furan-3-yl) -benzene-1,3-diol

1: 4- (tetrahydro-thiophen-3-yl) -benzene-1,3-diol

12: 4- (6-Oxa-spiro [4.5] dec-9-yl) -benzene-1,3-diol

13: 4-Chloro-6- (tetrahydro-pyran-4-yl) -benzene-1,3-diol

14: 4-Fluoro-6- (tetrahydro-pyran-4-yl) -benzene-1,3-diol

15: 4- (2,2-Diethyl-tetrahydro-pyran-4-yl) -benzene-1,3-diol

16: 4- (tetrahydro-pyran-3-yl) -benzene-1,3-diol

17: trans-4- (5-Hydroxymethyl-tetrahydro-furan-3-yl) -benzene-1,3-diol

18: cis-4- (5-Hydroxymethyl-tetrahydro-furan-3-yl) -benzene-1,3-diol

19: trans-4-Fluoro-6- (5-hydroxymethyl-tetrahydro-furan-3-yl) -benzene-1,3-diol

20: cis-4-Fluoro-6- (5-hydroxymethyl-tetrahydro-furan-3-yl) -benzene-1,3-diol 21: trans-4-Fluoro-6- (2-hydroxymethyl-tetrahydro-pyran-4-yl) -benzene-1,3-diol

22: cis-4-Fluoro-6- (2-hydroxymethyl-tetrahydro-pyran-4-yl) -benzene-1,3-diol

23: cis-4- (8-Oxa-bicyclo [3.2.1] oct-3-yl) -benzene-1,3-diol

24: trans-4- (8-Oxa-bicyclo [3.2.1] oct-3-yl) -benzene-1,3-diol

25: 4-Fluoro-6- (tetrahydro-thiopyran-4-yl) -benzene-1,3-diol.

4 - Composition according to one of claims 1 to 3 characterized in that the compound of formula (I) is 4- (tetrahydro-pyran-4-yl) -benzene-1,3-diol. 5. Composition according to one of claims 1 to 4, characterized in that the compound (s) of formula (I) are present in a content ranging from 0.001% to 10% by weight, relative to the total weight of the composition more particularly in a content ranging from 0.05% to 5% by weight, and preferably ranging from 0.1% to 3% by weight, and preferably ranging from 0.25% to 2% by weight.

6. Composition according to any one of the preceding claims, characterized in that (s) said glycol a) is chosen from propylene glycol, butylene glycol, pentylene glycol, hexylene glycol, dipropylene glycol diethylene glycol, 1,3-propanediol, 1,5-pentanediol, polyethylene glycol, and a mixture thereof.

7. Composition according to any one of the preceding claims, characterized in that said glycol (s) is chosen from dipropylene glycol, propylene glycol, butylene glycol, and mixtures thereof.

8. Composition according to any one of the preceding claims, characterized in that the said glycol (s) is present (s) in a content ranging from 0.5% to 60% by weight, relative to the weight total of the composition, preferably ranging from 5% to 50% by weight, and preferably ranging from 10% to 40% by weight, relative to the total weight of the composition.

9. Composition according to any one of the preceding claims, characterized in that the C 2 -C 4 monohydric alcohol (s) is (are) chosen from ethanol, propanol, isopropanol, butanol-1 and isobutanol. mixtures thereof and is preferably ethanol.

10. Composition according to any one of the preceding claims, characterized in that the C2-C4 monohydric alcohol (s) is (are) present in a content ranging from 0.1% to 30% by weight, preferably from 0.5% to 15% by weight, relative to the total weight of the composition.

1 1. Composition according to any one of the preceding claims, in which the weight ratio of the said monoalcohol / compound d) of formula (I) ranges from 1 to 20, preferably from 1.5 to 10.

12. Composition according to any one of the preceding claims, characterized in that it further comprises glycerine.

13. Composition according to the preceding claim, characterized in that the glycerin is present in concentrations ranging from 0.1% to 60% by weight, preferably from 1% to 50% by weight, preferably from 5 to 30% by weight. relative to the total weight of the composition.

14. Composition according to 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.

15. Composition according to any one of the preceding claims, characterized in that it is a cosmetic composition.

16. A process for the cosmetic treatment of keratin materials comprising the application to keratin materials, such as the skin, of a composition according to any one of the preceding claims.

17 A cosmetic process for depigmenting, lightening and / or bleaching keratinous substances, in particular human skin, hair or hair, comprising applying to said keratin materials a composition as defined according to any one of the claims 1 to 15.