WO2020000229A1

WO2020000229A1 - Whitening composition

Info

Publication number: WO2020000229A1
Application number: PCT/CN2018/092991
Authority: WO
Inventors: Yu Huang
Original assignee: L'oreal
Priority date: 2018-06-27
Filing date: 2018-06-27
Publication date: 2020-01-02
Also published as: CN112739318B; CN112739318A

Abstract

Provided is a cosmetic composition comprising, in an oily phase: a) an anti-ageing and/or antioxidant and/or depigmenting agent; b) at least one compound selected from esters of citric acid corresponding to formula (I) in which R1, R2, R3 and R4 have specific definitions; and c) at least one surfactant chosen from oxyethylene fatty acid and polyol esters, having an HLB of from 10 to 14. It also relates to a cosmetic composition in the form of an oil-in-water emulsion, comprising: -an oily phase as mentioned above, and -an aqueous phase comprising water, wherein the oily phase is dispersed in the aqueous phase.

Description

WHITENING COMPOSITION

The present invention concerns a cosmetic composition comprising, in an oily phase:

a) an anti-ageing and/or antioxidant and/or depigmenting agent;

b) a specific ester of citric acid; and

c) at least one surfactant chosen from oxyethylene fatty acid and polyol esters, having an HLB of from 10 to 14. It also relates to uses thereof.

It is common for people with colored or dark skin to lighten the skin. They generally use for this purpose cosmetic compositions containing one or more depigmenting or whitening agents. The most commonly used substances are hydroquinone and its derivatives, kojic acid and its derivatives, azelaic acid, arbutin and its derivatives, vitamin C and its derivatives (e.g. ascorbyl phosphate magnesium, or ascorbyl glucoside) , or resorcinol and its derivatives. These substances are generally difficult to formulate, and thus require special formulation constraints.

Particularly, cosmetic compositions comprising resorcinol or one of its derivatives turn yellow, because said active agent is difficult to stabilize.

The conventional arts did not disclose or provide a solution for preventing or reducing the yellowing of such compositions.

There thus exists a need for formulating a stable whitening composition which effectively protects the depigmenting agent, such as phenylethyl resorcinol, from turning yellow. There is also a need for providing a composition which may be simply obtained by manual shaking, and which is stable over time.

The Applicant has now discovered that it is possible to formulate a cosmetic composition having the desired properties as described above. Specifically, the Applicant has discovered that it is possible to formulate a skin care composition, especially for whitening, which is stable, which avoids yellowing and which is easy to use and to obtain. Said composition allows stabilizing the depigmenting agent.

The present invention thus relates to a cosmetic composition comprising, in an oily phase:

a) an anti-ageing and/or antioxidant and/or depigmenting agent;

b) at least one compound selected from esters of citric acid corresponding to formula (I) :

in which R1, R2 and R3, which are identical or different, each represent H or a linear, branched or cyclic, saturated or unsaturated C1-C30 alkyl chain,

wherein at least one of R1, R2 and R3 is different from H, and

R4 represents H or a group R'4-CO-, in which R'4 represents a linear, branched or cyclic, saturated or unsaturated C1-C8 alkyl group, preferably said ester is acetyl tributyl citrate; and

c) at least one surfactant chosen from oxyethylene fatty acid and polyol esters, having an HLB of from 10 to 14.

Said composition is called “oily phase composition” or “oily phase composition of the invention” in the present application.

Said oily phase composition is transparent. Indeed, its formulation prevents its yellowing, and the depigmenting agent is stable.

The oily phase composition may be mixed with an aqueous phase composition. Said aqueous phase composition is also transparent. The mixture may be performed by simple manual shaking, and the resulting composition becomes white or milky. Said composition is stable.

Thus, the present invention further relates to a kit comprising:

- a first container comprising the oily phase composition of the invention, and

- a second container comprising an aqueous phase composition comprising water.

The present invention also relates to a cosmetic method for caring the skin, comprising the following steps:

- mixing the oily phase composition of the invention with an aqueous phase composition comprising water, in order to obtain a mixture, and

- applying said mixture to said skin.

The present invention also relates to a cosmetic composition in the form of an oil-in-water emulsion, comprising:

- an oily phase comprising:

a) an anti-ageing and/or antioxidant and/or depigmenting agent;

wherein at least one of R1, R2 and R3 is different from H, and

c) at least one surfactant chosen from oxyethylene fatty acid and polyol esters, having an HLB of from 10 to 14, and

- an aqueous phase comprising water,

wherein the oily phase is dispersed in the aqueous phase.

Said composition is called “composition of the invention” in the present application.

Unless mention of the contrary, the percentages are expressed by weight of the total weight of the composition.

Other subjects and characteristics, aspects and advantages of the invention will emerge even more clearly on reading the description and the examples that follows.

In that which follows and unless otherwise indicated, the limits of a range of values are included within this range, in particular in the expressions "of between" and "ranging from ...to ..." .

Moreover, the expression "at least one" used in the present description is equivalent to the expression "one or more" .

Throughout the instant application, the term “comprising” is to be interpreted as encompassing all specifically mentioned features as well optional, additional, unspecified ones. As used herein, the use of the term “comprising” also discloses the embodiment wherein no features other than the specifically mentioned features are present (i.e. “consisting of” ) .

By “stable” oily phase composition, it is meant that said oily phase composition is transparent after one week at 65℃, and after two months at 45℃.

By “stable” composition of the invention, it is meant that said composition does not show any demulsification or float after one week at 65℃, and after two months at 45℃.

Oily phase composition

The oily phase composition comprises, in an oily phase:

a) an anti-ageing and/or antioxidant and/or depigmenting agent;

wherein at least one of R1, R2 and R3 is different from H, and

R4 represents H or a group R'4-CO-, in which R'4 represents a linear, branched or cyclic, saturated or unsaturated C1-C8 alkyl group; and

Preferably, the oily phase composition does not comprise any aqueous phase. Preferably, the oily phase composition is anhydrous. By anhydrous, it is meant a composition comprising less than 1%by eight of the total weight of the composition, of water. Preferably, the oily phase composition is devoid of water.

Said oily phase composition is transparent, notably when observed with the naked eye.

Anti-ageing and/or antioxidant and/or depigmenting agent

The anti-ageing and/or antioxidant and/or depigmenting agent a) may be a UV filter. Said UV filter may be organic or inorganic. The UV filter is a UV filter routinely used in cosmetics. It may be chosen in the positive list contained in Annex VI of the Regulation (EC) No. 1223/2009, which specifies the list of UV filters authorized in cosmetics.

The UV filter can provide a UVA and/or UVB photoprotection.

Organic UV filters are chosen particularly among cinnamic compounds; dibenzoylmethane compounds; anthranilate compounds; salicylic compounds, dibenzoylmethane compounds, benzylidene camphor compounds; benzophenone compounds; β, β-diphenylacrylate compounds; triazine compounds; and benzotriazole compounds.

Inorganic UV filters are metallic oxide pigments. They are preferably metallic oxide particles with an average elementary particle size of less than or equal to 0.5 μm, more preferably between 0.005 and 0.5 μm and even more preferably between 0.01 and 0.2 μm, even better between 0.01 and 0.1 μm, and especially between 0.015 and 0.05 μm. They can be chosen particularly among titanium, zinc, iron, zirconium and cerium oxides or mixtures thereof.

Preferably, the anti-ageing and/or antioxidant and/or depigmenting agent a) is a depigmenting agent.

Preferably, the depigmenting agent a) is selected from the group consisting of resorcinol and resorcinol derivatives. A single type of resorcinol derivative may also be used, but two or more different types of resorcinol derivative may be used in combination. A combination of resorcinol and a resorcinol derivative or a combination of different resorcinol compounds may be used.

Preferably, the resorcinol derivative is a compound represented by formula (I) :

wherein

R ₁ independently denotes -A-B where A represents a single bond, a C ₁-C ₆ alkylene group, a C ₆-C ₁₂ arylene group, or a C ₁-C ₆ alkylene-C ₆-C ₁₂ arylene group, and B represents a halogen atom, -OH, -COH, -COOH, -CONH ₂, -NH ₂, a C ₁-C ₆ alkyl group, a C ₁-C ₆ alkoxy group, a C ₁-C ₆ acyl group, a carbocyclic group, preferably an aryl group, or heterocyclic group, preferably a non-aromatic heterocyclic group, each of which may be substituted with at least one substituent selected from the group consisting of a hydroxyl group, a carboxyl group, a C ₁-C ₆ alkyl group, a C ₁-C ₆ alkylene-OH, an amino group, -CONH ₂, -CONH-C _1-6 alkyl group and a C ₁-C ₆ alkoxy group;

x is an integer of 1 to 4, preferably 1 to 3, more preferably 1 or 2 and even more preferably 1; and

R ₂ and R ₃ independently denote a hydrogen atom, a C ₁-C ₆ alkyl group, or a C ₁-C ₆ acyl group,

or a salt, a solvate, an optical isomer thereof, or a racemate thereof.

The C ₁-C ₆ alkylene group may be a straight or branched divalent group.

The C ₁-C ₆ alkylene-C ₆-C ₁₂ arylene group may also be a straight or branched divalent group. Either the C ₁-C ₆ alkylene moiety or the C ₆-C ₁₂ arylene moiety may bond the dihydroxy benzene ring shown in formula (I) .

The aryl group as “B” may be a C ₆-C ₁₂ aryl group such as a phenyl group, a tolyl group and a xylyl group, or a naphthyl group.

The hetero atom in the heterocyclic group as “B” may be an oxygen atom, a sulfur atom and a nitrogen atom. A single heteroatom or a plurality of hetero atoms may be included in the heterocyclic group. As examples of the heterocyclic group, mention may be made of a furanyl group, a pyrrole group, an oxazole group, an isoxazolyl group, a thiazolyl group, an isothiazolyl group, an imidazolyl group, a pyrazolyl group, a pyranyl group, a pyridinyl group, a pyridazinyl group, a pyrimidinyl group, a pyrazinyl group, an indolyl group, an isoindolyl group, a benzofuranyl group, a quinolinyl group, isoquinolinyl group and an indazolyl group.

As examples of the non-aromatic heterocyclic group, mention may be made of a pyrrolidinyl group, an imidazolidinyl group, a pyrazolidinyl group, a piperidinyl group, a piperazinyl group, a morpholinyl group, and a tetrahydropyranyl group.

As examples of the compound according to formula (I) , mention may be made of: phenylethyl resorcinol, 2-methylresorcinol, 5-methylresorcinol, 4-methylresorcinol, 2, 4-dihydroxybenzaldehyde, 4-ethylresorcinol, 2, 5-dimethylresorcinol, 4, 5-dimethylresorcinol, 2, 4-dimethyl-1, 3-benzenediol, 3, 5-dihydroxybenzylamine, 5-methoxyresorcinol, 3, 5-dihydroxybenzyl alcohol, 2-methoxyresorcinol, 4-methoxyresorcinol, 3, 5-dihydroxytoluene monohydrate, 4-chlororesorcinol, 2-chlororesorcinol, 2’, 4’-dihydroxyacetophenone, 3’, 5’-dihydroxyacetophenone, 2, 6-dihydroxy-4-methylbenzaldehyde, 4-propylresorcinol, 2, 4-dihydroxy-1, 3, 5-trimethylbenzene, 3, 5-dihydroxybenzamide, 2, 6-dihydroxybenzamide, 2, 4-dihydroxybenzamide, 2, 4-dihydroxybenzoic acid, 2, 6-dihydroxybenzoic acid, 3, 5- dihydroxybenzoic acid, 2, 6-dihydroxy-4-methylbenzyl alcohol, 3, 5-dihydroxyanisole hydrate, 4-aminoresorcinol hydrochloride, 2-aminoresorcinol hydrochloride, 5-aminobenzene-1, 3-diol hydrochloride, 2’, 4’-dihydroxypropiophenone, 2’, 4’-dihydroxy-3’-methylacetophenone, (2, 4-dihydroxyphenyl) acetone, (3, 5-dihydroxyphenyl) acetone, 2, 6-dihydroxy-4’-methylacetophenone, 4-n-butylresorcinol, 2, 4-diethyl-1, 3-benzenediol, 3, 5-dihydroxy-4-methylbenzoic acid, 2, 6-dihydroxy-4-methylbenzoic acid, 2, 4-dihydroxy-6-methylbenzoic acid, 3, 5-dihydroxyphenylacetic acid, 2-ethyl-5-methoxybenzene-1, 3-diol, 4-amino-3, 5-dihydroxybenzoic acid, 3, 5-dihydroxyacetophenone monohydrate, 3, 5-dihydroxybenzylamine hydrochloride, 4, 6-dichlororesorcinol, 2’, 4’-dihydroxy-3’-methylpropiophenone, 1- (3-ethyl-2, 6-dihydroxyphenyl) ethan-1-one, 2’, 6’-dihydroxy-4’-methoxyacetophenone, 1- (2, 6-dihydroxy-3-methoxyphenyl) ethan-1-one, 3 (2, 4-dihydroxyphenylpropionic acid, 2, 4-dihydroxy-3, 6-dimethylbenzoic acid, and hexylresorcinol.

It is preferable that the resorcinol derivative be a compound represented by formula (Ia) :

wherein

R ₁, R ₂ and R ₃ have the same meanings as above,

or a salt, a solvate, an optical isomer thereof, or a racemate thereof.

It is more preferable that, in the above formula (Ia) :

R ¹ denotes –A-B where A represents a single bond or a C ₁-C ₆ alkylene group, and B represents a phenyl group or a tetrahydropyranyl group; and each of R ₂ and R ₃ denotes a hydrogen atom.

It is even more preferable that the resorcinol derivative be phenylethyl resorcinol.

It is also preferable that the resorcinol derivative be a compound represented by formula (II) :

wherein

R ₂ and R ₃ independently denote a hydrogen atom or an acetyl group;

A denotes a radical selected from:

a) -H;

b) –a C ₃-C ₈ cyclic or C ₃-C ₂₀ branched or C ₂-C ₂₀ unsaturated or C ₁-C ₂₀ saturated linear alkyl group which is optionally interrupted by one or more heteroatoms or moieties selected from N, O and -CO-or a combination thereof such as -NHCO-, -NHCONH-and/or is optionally substituted by one or more identical or different groups selected from:

i) -OR ₅

ii) -SR ₅

iii) -NR ₆R ₇

iv) -CONHR ₆

v) -CONR ₆R ₇

vi) -COOR ₆

vii) –NHCONHR ₆

viii) -C (O) C ₁-C ₄ alkyl

ix) a C ₅-C ₁₂ (hetero) aryl group optionally containing one or more heteroatoms selected from O, N and S and optionally substituted by one or more hydroxyls and/or by one or more C ₁-C ₈ alkoxy radicals;

x) a saturated or unsaturated, non-aromatic heterocycle having from 5 to 8 members and comprising one or more heteroatoms selected from O, N and S which is optionally substituted by one or more hydroxyls and/or by one or more C ₁-C ₈ alkoxy or C ₁-C ₄ alkyl radicals, it being possible for one of the members to be a carbonyl group;

c) –a C ₅-C ₁₂ (hetero) aryl group optionally containing one or more heteroatoms selected from O, N and S and optionally substituted by one or more hydroxyls and/or by one or more radicals selected from C ₁-C ₈ alkoxy or C ₁-C ₈ alkyl groups;

d) -NR ₈R ₉;

e) -OR ₄;

f) -C (O) NHR ₄;

g) C (O) C ₁-C ₁₀ alkyl,

where

R ₈ and R ₉, which are identical or different, denote a radical selected from:

a) -H;

b) –a C ₃-C ₈ cyclic or C ₃-C ₁₀ branched or C ₂-C ₁₀ unsaturated or C ₁-C ₁₀ linear saturated alkyl group which is optionally interrupted by one or more heteroatoms or moieties selected from N, O and -CO-or a combination thereof such as -NHCO-, -NHCONH-and/or is optionally substituted by one or more identical or different groups selected from -OR ₅;

c) a C ₅-C ₁₂ (hetero) aryl group optionally containing one or more heteroatoms selected from O, N and S and optionally substituted by one or more hydroxyls and/or by one or more C ₁-C ₈ alkoxy radicals;

it being possible for R ₈ and R ₉ to form, with the nitrogen which carries them, a heterocycle which has from 5 to 8 members and may contain one or more heteroatoms or moieties selected from N, O and -CO-and/or is optionally substituted by a C ₁-C ₁₀ hydrocarbon chain optionally containing one or more radicals selected from hydroxyl or C ₁-C ₄ alkoxy; R ₄ denotes a radical selected from:

a) -H

b) a C ₃-C ₈ cyclic or C ₃-C ₁₀ branched or C ₁-C ₁₀ linear saturated alkyl group which is optionally substituted by one or more identical or different groups selected from:

i) -COOR ₆,

ii) a C ₅-C ₁₂ (hetero) aryl radical which optionally contains one or more heteroatoms selected from O, N and S and is optionally substituted by one or more hydroxyls and/or by one or more C ₁-C ₈ alkoxy radicals;

c) a C ₅-C ₁₂ (hetero) aryl group which optionally contains one or more heteroatoms selected from O, N and S and is optionally substituted by one or more hydroxyls and/or by one or more C ₁-C ₈ alkoxy radicals;

R ₅ is selected from H and a C ₃-C ₈ cyclic or C ₂-C ₁₀ unsaturated or C ₃-C ₁₀ branched or C ₁-C ₁₀ linear saturated alkyl hydrocarbon group;

R ₆ and R ₇, which are identical or different, are selected from H, a C ₃-C ₈ cyclic or C ₂-C ₁₀ unsaturated or C ₃-C ₁₀ branched or C ₁-C ₁₀ linear saturated alkyl hydrocarbon group; a (C ₁-C ₄) alkyl-C ₆ (hetero) aryl group optionally containing a nitrogen atom, more particularly a benzyl group;

R ₆ and R ₇ may form, with the nitrogen which carries them, a heterocycle which has from 5 to 8 members and may contain one or more heteroatoms or moieties selected from N, O and -CO-and/or is optionally substituted by a C ₁-C ₁₀ hydrocarbon chain; h) a radical of formula (III) :

in which:

X denotes a C ₃-C ₈ cyclic or C ₃-C ₁₀ branched or C ₁-C ₁₀ linear saturated hydrocarbon chain or a C ₆-C ₁₂ arylene group such as phenylene, or a C ₁-C ₄ alkylene-C ₆-C ₈ cycloalkylene-C ₁-C ₄ alkylene group or a C ₁-C ₄ alkylene-phenylene-C ₁-C ₄ alkylene group, which is optionally substituted by one or more identical or different radicals selected from -OH, -COOR ₆ where R ₆ denotes H or a C ₃-C ₈ cyclic or C ₂-C ₁₀ unsaturated or C ₃-C ₁₀ branched or C ₁-C ₂₀ linear saturated alkyl hydrocarbon group;

R ₂ and R ₃ have the same meanings as above; and when A denotes a radical of formula (III) , all of the radicals R ₂ and R ₃ in the compounds of formula (II) are identical, or a salt, a solvate, an optical isomer thereof, or a racemate thereof.

The salts of the compounds of formulae (I) and (II) include conventional non-toxic salts of said compounds, such as those formed from an acid or from a base.

Salts of the compound of formulae (I) and (II) (when it comprises a quaternizable nitrogen atom) include the following:

- salts obtained by addition of compound (I) or (II) with a mineral acid, selected more particularly from hydrochloric, boric, hydrobromic, hydroic, sulphuric, nitric, carbonic, phosphoric and tetrafluoroboric acids;

- or the salts obtained by addition of compound (I) or (II) with an organic acid, more particularly selected from acetic, propionic, succinic, fumaric, lactic, glycolic, citric, gluconic, salicylic, tartaric, terephthalic, methylsulphonic, ethylsulphonic, benzene sulphonic, toluene sulphonic and triflic acids.

Also included are the salts obtained by addition of the compound of formula (I) or (II) (when it comprises an acidic group) with a mineral base, such as aqueous sodium hydroxide and potassium hydroxide, calcium hydroxide, ammonium hydroxide, magnesium hydroxide, lithium hydroxide, and sodium, potassium or calcium carbonates or hydrogencarbonates, for example; or with an organic base such as a primary, secondary or tertiary alkylamine, for example triethylamine or butylamine. This primary, secondary or tertiary alkylamine may comprise one or more nitrogen and/or oxygen atoms and may therefore comprise, for example, one or more alcohol functions; included more particularly are 2-amino-2-methylpropanol, ethanolamine, triethanolamine, 2-dimethylamino propanol, 2-amino-2- (hydroxymethyl) -1, 3-propanediol and 3- (dimethylamino) propylamine.

Also included are the salts of amino acids such as, for example, lysine, arginine, guanidine, glutamic acid and aspartic acid.

The salts of the compounds of formulae (I) and (II) (when they comprise an acidic group) may advantageously be selected from alkali metal salts or alkaline earth metal salts such as sodium, potassium, calcium and magnesium salts; and ammonium salts.

The salts of the compounds of formulae (I) and (II) (when they comprise a quaternizable nitrogen atom) may advantageously be selected from halides such as chloride and bromide; and from citrates, acetates, succinates, phosphates, lactates and tartrates.

The acceptable solvates of the compounds described in the present invention comprise conventional solvates such as those formed during the preparation of said compounds as a result of the presence of solvents. Examples include the solvates resulting from the presence of water or of linear or branched alcohols such as ethanol or isopropanol.

The optical isomers are more particularly enantiomers and diastereoisomers.

The linear or branched groups may preferably be selected from methyl, ethyl, propyl, isopropyl, butyl, isobutyl, tert-butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, undecyl, dodecyl, tridecyl, tetradecyl, pentadecyl, hexadecyl, heptadecyl, octadecyl, nonadecyl and eicosyl.

The saturated linear or branched alkyl groups may more preferably be selected from methyl, ethyl, propyl, isopropyl, butyl, isobutyl, tert-butyl, pentyl, hexyl, heptyl and octyl.

The C ₁-C ₄ alkoxy groups may preferably be selected from methoxy, ethoxy, propoxy and butoxy and more preferably methoxy.

The compounds of formula (II) preferably have the following meanings:

R ₂ and R ₃ independently denote a hydrogen atom or an acetyl group;

A denotes a radical selected from:

a) -H

b) -a C ₃-C ₈ cyclic or C ₃-C ₁₆ branched or C ₂-C ₁₆ unsaturated or C ₁-C ₁₆ linear saturated alkyl group which is optionally interrupted by one or more heteroatoms or moieties selected from N, O, -CO-and -NHC (O) -and/or is optionally substituted by one or more identical or different groups selected from:

i) -OH,

ii) C ₁-C ₄ alkoxy,

iii) -COOR ₆,

iv) -CONR ₆R ₇ where R ₆ and R ₇, which are identical or different, denote H or a C ₃-C ₈ cyclic or C ₂-C ₈ unsaturated or C ₃-C ₈ branched or C ₁-C ₈ linear saturated alkyl group;

v) a phenyl group which is optionally substituted by one or more hydroxyls and/or by one or more C ₁-C ₄ alkoxy radicals;

vi) a non-aromatic saturated or unsaturated heterocycle having from 5 to 8 members, comprising one or more heteroatoms selected from O, N and S, it being possible for one of the members to be a carbonyl group;

c) a C ₅-C ₁₂ aryl group such as phenyl which is optionally substituted by one or more identical or different radicals selected from OH, C ₁-C ₄ alkoxy and C ₁-C ₄ alkyl;

d) -NR ₈R ₉, where R ₈ and R ₉, which are identical or different, denote:

i) H;

ii) a C ₃-C ₈ cyclic or C ₂-C ₈ unsaturated or C ₃-C ₈ branched or C ₁-C ₈ linear saturated alkyl group which is optionally interrupted by an oxygen atom and/or is optionally substituted by a hydroxyl group or a C ₁-C ₄ alkoxy group such as methoxy;

iii) a C ₅-C ₁₂ aryl group which is optionally substituted by one or more hydroxyls and/or by one or more C ₁-C ₄ alkoxy radicals;

it being possible for R ₈ and R ₉ to form, with the nitrogen which carries them, a heterocycle having from 5 to 8 members, said heterocycle being able to contain one or more oxygen atoms and/or being optionally substituted by a C ₁-C ₆ hydrocarbon chain optionally containing one or more radicals selected from hydroxyl or C ₁-C ₄ alkoxy;

e) -OR ₄

f) -C (O) NHR ₄,

where R ₄ denotes a radical selected from -H, a C ₃-C ₈ branched or C ₁-C ₈ linear saturated alkyl group which is optionally substituted by one or more identical or different groups selected from:

i) -COOR ₆, where R ₆ is as defined above;

ii) a C ₅-C ₁₂ aryl radical,

g) a radical of formula (III)

in which X denotes a C ₃-C ₈ cyclic or C ₃-C ₆ branched or C ₁-C ₆ linear saturated hydrocarbon chain or a C ₆-C ₁₂ arylene group such as phenylene, which is optionally substituted by one or more identical or different radicals selected from OH or a C ₁-C ₆ alkyl group,

R ₂ and R ₃ have the same meanings as above;

and

when A denotes a radical of formula (III) , all of the radicals R ₂ and R ₃ in the compounds of formula (II) are identical.

The compounds of formula (I) more preferably have the following meanings:

R ₂ and R ₃ independently denote a hydrogen atom or an acetyl group;

A denotes a radical selected from:

a) H

b) a C ₃-C ₈ cyclic or C ₃-C ₁₆ branched or C ₂-C ₁₆ unsaturated or C ₁-C ₁₆ linear saturated alkyl group which is optionally interrupted by one or more heteroatoms selected from N and O and/or is optionally substituted by one or more identical or different groups selected from:

i) –OH

ii) C ₁-C ₄ alkoxy,

iii) -CONH ₂;

iv) -COOR ₆, where R ₆ denotes H or a C ₃-C ₄ cyclic or C ₂-C ₄ unsaturated or C ₃-C ₄ branched or C ₁-C ₄ linear saturated alkyl group;

vi) a saturated or unsaturated, non-aromatic heterocycle having from 5 to 8 members, comprising one or more nitrogen atoms, it being possible for one of the members to be a carbonyl moiety;

c) a C ₅-C ₁₂ aryl group such as phenyl;

d) -NR ₈R ₉, where R ₈ and R ₉, which are identical or different, denote H or a C ₃-C ₈ cyclic or C ₂-C ₆ unsaturated or C ₃-C ₆ branched or C ₁-C ₆ linear saturated alkyl group; or a C ₅-C ₁₂ aryl group such as phenyl;

it being possible for R ₈ and R ₉ to form, with the nitrogen which carries them, a heterocycle having from 5 to 8 members, it being possible for said heterocycle to contain an oxygen atom and/or being optionally substituted by a C ₁-C ₆ hydrocarbon chain optionally containing one or more radicals selected from hydroxyl or C ₁-C ₄ alkoxy;

e) -OR ₄, where R ₄ denotes H or a C ₃-C ₆ branched or C ₁-C ₆ linear saturated alkyl group which is optionally substituted by one or more identical or different groups selected from:

i) -COOH,

ii) a C ₅-C ₁₂ aryl radical such as phenyl;

f) a radical of formula (III)

in which X denotes a C ₃-C ₈ cyclic or C ₃-C ₆ branched or C ₁-C ₆ linear saturated hydrocarbon chain or a C ₆-C ₁₂ arylene group such as phenylene, which is optionally substituted by one or more hydroxyl radicals;

R ₂ and R ₃ have the same meanings as above; and

Preferentially, R ₂ and R ₃ = H for the compounds of formula (II) .

A number of embodiments of compounds of formula (II) are described below:

R ₂ and R ₃ = H, and A = H.

R ₂ and R ₃ = H, and A = C ₃-C ₁₆ branched or C ₁-C ₁₆ saturated linear alkyl group.

R ₂ and R ₃ = H, and A = C ₃-C ₈ branched or C ₁-C ₈ saturated linear alkyl group which is substituted by one or two hydroxyl groups and is optionally substituted by the group -SR ₅, where R ₅ = H or C ₁-C ₄ alkyl.

R ₂ and R ₃ = H, and A = phenyl or benzyl group.

R ₂ and R ₃ = H, and A = C ₃-C ₈ branched or C ₁-C ₈ alkyl group which is substituted by a phenyl group which is optionally substituted by one or more hydroxyl groups and/or C ₁-C ₄ alkoxy group.

R ₂ and R ₃ = H, and A = C ₃-C ₈ branched or C ₁-C ₈ saturated linear alkyl group which is substituted by a –COOH group, which is optionally substituted by the group SR ₅, where R ₅ = H or C ₁-C ₄ alkyl.

R ₂ and R ₃ = H, and A = C ₃-C ₈ branched or C ₁-C ₈ saturated linear alkyl group which is substituted by the group –COOR ₆, where R ₆ denotes a C ₁-C ₆ alkyl group, and is optionally substituted by a hydroxyl group and/or the group -SR ₅, where R ₅ = H or C ₁-C ₄ alkyl and/or phenyl which is optionally substituted by one or more hydroxyls, or an imidazole radical.

R ₂ and R ₃ = H, and A = C ₃-C ₈ branched or C ₁-C ₈ saturated linear alkyl group which is substituted by a –CONH ₂ group, which is optionally substituted by a hydroxyl or phenyl group which is optionally substituted by one or more hydroxyls, or the group–COOR ₆, where R ₆ denotes a C ₁-C ₆ alkyl group.

R ₂ and R ₃ = H, and A = group -OR ₄, where R ₄ denotes H, a C ₃-C ₆ branched or C ₁-C ₆ linear saturated alkyl group which is optionally substituted by a –COOH group or a phenyl group.

R ₂ and R ₃ = H, and A = -NR ₈R ₉, where R ₈ and R ₉, which are identical or different, denote H or a C ₃-C ₆ branched or C ₁-C ₆ linear saturated alkyl group or a phenyl group; it being possible for R ₈ and R ₉ to form, with the nitrogen which carries them, a heterocycle which has 5 or 6 members and may contain an oxygen atom, said heterocycle being optionally substituted by a C ₁-C ₆ hydrocarbon chain optionally containing one or more radicals selected from hydroxyl or C ₁-C ₄ alkoxy.

R ₂ and R ₃ = H, and A = C ₃-C ₆ branched or C ₂-C ₆ linear alkyl group interrupted by a –CONH-group and substituted by a COOH group.

R ₂ and R ₃ = H, and A = C ₅-C ₆ cyclic alkyl group interrupted by a –CONH-group.

R ₂ and R ₃ = H, and A = C ₅-C ₆ cyclic alkyl group interrupted by an oxygen atom.

R ₂ and R ₃ = H, and A = radical of formula (II) as described above in which X denotes a C ₅- C ₈ cyclic or C ₃-C ₆ branched or C ₁-C ₆ linear saturated hydrocarbon chain or a phenylene group, which is optionally substituted by one or more hydroxyl groups.

Among these compounds, more particular preference is given to the following compounds:

and also their salts, their solvates, their optical isomers and their racemates.

The above compounds can be prepared in accordance with, for example, the process described in WO 2012/079938.

Peferably, the depigmenting agent (a) is chosen from resorcinol, butyl resorcinol, and phenylethyl resorcinol.

Preferably, the depigmenting agent (a) is phenylethyl resorcinol, which has the following formula:

The other names are 4- (1-phenylethyl) -1, 3-benzenediol or 4- (1-phenylethyl) -1, 3-dihydroxybenzene or styrylresorcinol. This compound has the CAS number 85-27-8.

Such a compound is marketed under the name SYMWHITE 377 by the company Symrise.

The anti-ageing and/or antioxidant and/or depigmenting agent a) , preferably the depigmenting agent, may be present in the oily phase composition, in an amount of at least 1%by weight, preferably from 1%to 20%by weight, preferably from 2%to 10%by weight, and more preferably from 3%to 8%by weight relative to the total weight of the oily phase composition.

Citric acid ester (compound b)

The oily phase composition also comprises at least one compound (component b) selected from esters of citric acid corresponding to formula (I) :

in which R1, R2 and R3, which are identical or different, each represent H or a linear, branched or cyclic, saturated or unsaturated C1-C30 alkyl chain, wherein at least one of R1, R2 and R3 is different from H, and

R4 represents H or a group R'4-CO-, in which R'4 represents a linear, branched or cyclic, saturated or unsaturated C1-C8 alkyl group.

Such a compound is also called “citric acid ester” in the present application.

Preferably, R1, R2 and R3 are identical and represent a linear saturated C2-C10 alkyl chain, preferably C3-C6 alkyl chain. Preferably, R1, R2 and R3 are identical and each represent n-butyl radical.

Preferably R4 is R’4-CO-wherein R’4 is a linear saturated C1-C5 alkyl group, preferably methyl.

Preferably, said compound is chosen from acetyl tributyl citrate, triethyl citrate, tributyl citrate, triethyl acetylcitrate and triethyl-2-hexyl acetylcitrate.

Preferably, the citric acid ester is acetyl tributyl citrate. The oily phase composition preferably comprises acetyl tributyl citrate (component b) .

Acetyl tributyl citrate is the compound of the following formula:

Said citric acid ester is used as a solvent for the anti-ageing and/or antioxidant and/or depigmenting agent a) , in the present invention.

It may be sold under the name Uniplex 84 by Unitex Chemical.

Preferably, the citric acid ester b) is present in the oily phase composition, in an amount of at least 50%by weight, preferably from 55%to 98%by weight, preferably from 60%to 95%by weight, and more preferably from 65%to 80%by weight relative to the total weight of the oily phase composition.

Oxyethylene fatty acid and polyol ester

The oily phase composition also comprises at least one surfactant chosen from oxyethylene fatty acid and polyol esters, having an HLB of from 10 to 14 (component c) .

Preferably, the fatty acid is a linear or grafted, preferably grafted, fatty acid having 14 to 22 carbon atoms. Preferably it is isostearic acid.

Preferably the polyol is glycerin or sorbitol. Preferably the ester is a mono-, di-or triester, more preferably a triester.

Preferably, the surfactant c) is chosen from oxyethylenated glyceryl triisostearate (20 OE) and oxyethylenated sorbitan trioleate (20 OE) . More preferably, the surfactant c) is oxyethylenated glyceryl triisostearate (20 OE) .

Oxyethylenated glyceryl triisostearate (20 OE) is also known under the INCI name PEG-20 glyceryl triisostearate, and is sold under the name Uniox GT 20IS L by NOF Corporation.

The surfactant c) may be present in the oily phase composition, in an amount of at least 1%by weight, preferably from 1%to 20%by weight, preferably from 2%to 10%by weight, and more preferably from 3%to 8%by weight relative to the total weight of the oily phase composition.

Oily phase ingredients

The oily phase composition may also comprise further lipophilic ingredients, such as solvents or lipophilic active agents.

Preferably, the oily phase further comprises a solvent chosen from lipophilic derivatives of amino acids, such as glycine. Preferably the lipophilic derivative is isopropyl lauroyl sarcosinate, such as the one sold under the name Eldew SL 205 by Ajinomoto.

The solvent chosen from lipophilic derivatives of amino acids may be present in the oily phase composition, in an amount of at least 5%by weight, preferably from 5%to 40%by weight, preferably from 10%to 30%by weight, and more preferably from 15%to 25%by weight relative to the total weight of the oily phase composition.

Preferably, lipophilic active agents are salicylic acid derivatives, which include 5-n-octanoyl salicylic acid (capryloyl salicylic acid) , 5-n-decanoyl salicylic acid, 5-n-dodecanoyl salicylic acid, 5-n-heptyloxy salicylic acid and 4-n-heptyloxy salicylic acid. A highly preferred salicylic acid derivative is capryloyl salicylic acid (Trade name: Mexoryl SAB from Chimex) . It may be present in the oily phase composition, in an amount of at least 1%by weight, preferably from 1%to 10%by weight, preferably from 1.5%to 8%by weight, and more preferably from 2%to 5%by weight relative to the total weight of the oily phase composition.

Composition of the invention

- an oily phase comprising:

a) an anti-ageing and/or antioxidant and/or depigmenting agent;

- an aqueous phase comprising water, wherein the oily phase is dispersed in the aqueous phase.

In other words, the present invention also relates to a cosmetic composition in the form of an oil-in-water emulsion, comprising:

- an oily phase as previously described, and

The composition of the invention has a milky or white appearance.

All embodiments which apply to the oily phase composition further apply to the composition of the invention.

More specifically, regarding the amounts, the surfactant c) is preferably present in an amount of less than 1%by weight of the total weight of the composition, preferably from 0.1%to 0.9%by weight, preferably from 0.2%to 0.8%by weight.

Preferably, the anti-ageing and/or antioxidant and/or depigmenting agent a) is present in an amount of less than 1%by weight of the total weight of the composition, preferably from 0.1%to 0.9%by weight, preferably from 0.2%to 0.8%by weight.

Preferably, the citric acid ester b) is present in an amount of from 1%to 10%by weight of the total weight of the composition, preferably from 2%to 8%by weight, preferably from 3%to 5%by weight.

The composition of the invention also comprises an aqueous phase.

Aqueous phase

According to a particular embodiment, the composition comprises a quantity of water from 50%to 98%by weight, better from 60%to 97%by weight, and preferably from 70%to 95%by weight in relation to the total weight of the composition.

The water used can be sterile demineralized water and/or floral water such as rose water, cornflower water, chamomile water or linden water, and/or a spring or natural mineral water, such as for example: Vittel water, water from the basin of Vichy, Uriage water, la Roche Posay water, la Bourboule water, Enghien-les-Bains water, Saint Gervais-les-Bains water, Néris-les-Bains water, Allevar-les-Bains water, Digne water, Maizières water, Neyrac-les-Bains water, Lons-le-Saunier water, les Eaux Bonnes, Rochefort water, Saint Christau water, Fumades water and Tercis-les-bains water, Avene water.

The aqueous phase may comprise at least one solvent miscible with water. Said solvent may be chosen from polyols and alcohols, such as glycerin, sorbitol, glycols such as butylene glycol, propylene glycol, isoprene glycol, dipropylene glycol, hexylene glycol, polypropylene glycol, ethanol or propanediol.

Preferably, the aqueous phase further comprises at least one ingredient chosen from:

- non-ionic surfactants which are polyoxyethylenated (from 1 to 40 EO) and polyoxypropylenated (from 1 to 30 PO) alkyl C16-C30 ethers with an HLB value of 13.0 or less;

- oxyalkylenated sugar ethers, such as oxyethylenated methyl glucose ethers;

- hydrophilic gelling agents, preferably chosen from carboxyvinyl polymers modified or not, polymers of natural origin such as xanthan gum, and homopolymers and copolymers with an acrylamido propane sulfonic acid base; and

- their mixtures.

Among the non-ionic surfactants which are polyoxyethylenated (from 1 to 40 EO) and polyoxypropylenated (from 1 to 30 PO) alkyl C16-C30 ethers with an HLB value of 13.0 or less, one can quote PPG-6 Decyltetradeceth-30, which is also called Polyoxyethylene (30) Polyoxypropylene (6) Tetradecyl Ether. It may be sold as Nikkol PEN-4630 from Nikko Chemicals Co. Preferably, said non-ionic surfactant is present in an amount of less than 1%by weight of the total weight of the composition, preferably from 0.1%to 0.9%by weight, preferably from 0.2%to 0.8%by weight.

Among the oxyalkylenated sugar ethers, oxyethylenated sugar ethers are preferably used. Preferably, one can quote oxyethylenated methyl glucose ethers, such as methyl gluceth-20 such as Glucam E-20 Humectant sold by Lubrizol. Preferably, said oxyalkylenated sugar ether is present in an amount of less than 1%by weight of the total weight of the composition, preferably from 0.1%to 0.9%by weight, preferably from 0.2%to 0.8%by weight.

The hydrophilic gelling agent may be chosen from hydrophilic thickening polymers. More particularly, this thickening polymer can be chosen from:

- homo-or copolymers of acrylic or methacrylic acid or the salts thereof and the esters thereof and in particular the products sold under the names VERSICOL F or VERSICOL K by ALLIED COLLOID, UTRAHOLD 8 by CIBA-GEIGY, polyacrylic acids of the SYNTHALEN K type, and the salts, in particular sodium, of polyacrylic acid (with the INCI name of sodium acrylate copolymer) and more particularly a cross-linked sodium polyacrylate (with the INCI name of sodium acrylate copolymer (and) caprylic/capric triglyceride) sold under the name LUVIGEL EM,

- acrylic and acrylamide acid copolymers such as those sold in the form of their sodium salt under the names RETEN by HERCULES, sodium polymethacrylate sold under the name DARVAN N°7 by VANDERBILT, the sodium salts of polyhydroxycarboxylic acids sold under the name HYDAGEN F by HENKEL,

- polyacrylic acid/alkyl acrylates copolymers, preferably carboxyvinyl polymers modified or not, according to this invention, the acrylate/C10-C30-alkylacrylate INCI name Acrylates/C10-30 Alkyl acrylate Crosspolymer) copolymers are very particularly preferred such as the products sold by Lubrizol under the trade names PEMULEN TR1, PEMULEN TR2, CARBOPOL 1382, CARBOPOL EDT 2020 and more preferably PEMULEN TR-2,

- homopolymers and copolymers with an acrylamido propane sulfonic acid (AMPS) base, such as for example:

- polyacrylamidomethyl propane sulfonic acid partially neutralized with ammonia and highly cross-linked, sold in particular by CLARIANT, for example under the name HOSTACERIN

- copolymers of acrylamidomethyl /acrylamide propane sulfonic acid for example of the SEPIGEL or SIMULGEL type sold in particular by SEPPIC,

- copolymers of acrylamidomethyl /methylacrylate propane sulfonic acid of polyoxyethylene alkyl (cross-linked or not) among others of the ARISTOFLEX HMS, ARISTOFLEX TAC type, sold by CLARIANT,

- copolymers of acrylamidomethyl propane sulfonic acid and of hydroxyethyl acrylate, such as for example the acrylamidomethyl propane sulfonic acid /hydroxyethyl acrylate copolymer such as in particular the one used in the commercial product sold under the name SIMULGEL NS by SEPPIC, or the acrylamidomethyl propane sulfonic acid /hydroxyethyl acrylate copolymer such as in particular the one used in the commercial product sold under the name SEPINOV EMT 10 sold by SEPPIC (INCI name: HYDROXYETHYL ACRYLATE/SODIUM ACRYLOYLDIMETHYL TAURATE COPOLYMER) ;

- anionic, cationic, amphoteric or non-ionic chitin or chitosan polymers;

- cellulose polymers, in particular separate from alkylcellulose, chosen from hydroxyethylcellulose, hydroxypropylcellulose, hydroxymethylcellulose, ethylhydroxyethylcellulose, carboxymethylcellulose, and quaternized cellulose derivatives;

- vinyl polymers, such as polyvinylpyrrolidones, methylvinyl ether and malic anhydride, vinyl acetate and crotonic acid copolymer, vinylpyrrolidone and vinyl acetate copolymers; vinylpyrrolidone and caprolactam copolymers; polyvinyl alcohol;

- polymers of natural origin, possibly modified, such as: galactomannans and derivatives thereof, such as Konjac gum , Gellan gum, Carob gum, Fenugrec gum, Karaya gum, Tragacanthe gum, gum arabic, gum acacia, guar gum, hydroxypropylguar, hydroxypropylguar modified by sodium methylcarboxylate groups (Jaguar XC97-1, Rhodia) , ammonia trimethyl hydroxypropyl guar chloride, xanthan gum and the derivatives of xanthan;

- alginates and carrageenans;

- mucopolysaccharides such as hyaluronic acid, chondroitin sulfates;

- and mixtures thereof.

Preferably the hydrophilic gelling agent is chosen from carboxyvinyl polymers modified or not, polymers of natural origin such as xanthan gum, and homopolymers and copolymers with an acrylamido propane sulfonic acid base. Preferably, said hydrophilic gelling agent is present in an amount of less than 1%by weight of the total weight of the composition, preferably from 0.1%to 0.9%by weight, preferably from 0.2%to 0.8%by weight.

The composition of the invention may comprise additional ingredients. Said additional ingredient can be, for example, any colorant (pigment, dye...) particularly in the aqueous phase, and/or any pharmaceutically or cosmetically active agent. Depending on its use, functional active agents for skin treatment, such as UV filters, anti-oxidants and/or anti-wrinkle agents could be included in the composition.

The composition of the invention is obtained by mixing the oily phase composition with an aqueous phase composition. Such a mixture may be performed by simple manual shaking. Whereas the oily phase composition and the aqueous phase composition are each transparent, the mixture of the oily phase composition with the aqueous phase composition results in a white or milky composition. The aqueous phase composition comprises the ingredient (s) mentioned in the section “Aqueous phase” above.

The present invention thus relates to a kit comprising:

- a first container comprising the oily phase composition of the invention, and

- a second container comprising an aqueous phase composition comprising water.

Preferably, the first container is a pipette.

The kit according to the invention can be used in the packaging and dispensing device as disclosed in, for example, WO2017/127992, and the package filling assembly as disclosed in WO2017/127993.

Indeed, such a packaging and dispensing device allows an easy mixing of the two distinct compositions (i.e. oily phase composition and aqueous phase) before application. Preferably, the kit according to the invention is a packaging and dispensing device comprising:

- a container for storing the aqueous phase composition, said container comprising an opening;

- a pipette removably inserted in the container through the opening, said pipette extending along an axis and having a first dispensing end and a second end;

- a plug removably assembled to the dispensing end of the pipette, said assembled pipette and plug defining an inner compartment for temporarily storing the oily phase composition isolated from the aqueous phase composition ; and

- a pressure supply device comprising :

- a support assembled to the second end of the pipette ;

- a compressible chamber in fluid communication with the second end of the pipette ; and

- a first pressure member able to move relative to the support, between a first and a second configurations, so as to lessen a volume of the compressible chamber, thereby increasing a pressure in the inner compartment ;

wherein the pressure supply device comprises locking elements for maintaining the first pressure member in the second configuration with an increased pressure in the inner compartment.

Preferably, the kit according to the invention is a filling assembly comprising:

- a container for storing the aqueous phase composition, said container comprising an opening; and

- a pipette removably inserted in the container through the opening, said pipette having a first dispensing end and a second open end configured to be assembled to a pressure supply device; and

- a plug removably assembled to the dispensing end of the pipette, said assembled pipette and plug defining an inner compartment for temporarily storing the oily phase composition isolated from the aqueous phase composition,

the filling assembly comprising a holding element configured to hold the pipette inside the container in a predetermined position while maintaining at least one aperture within the opening, said aperture allowing for fluid communication between the outside and the inside of the container, so that the container and the pipette may be filled simultaneously with the oily phase composition and the aqueous phase composition respectively, before assembling the second open end of the pipette with the pressure supply device.

- applying said mixture to said skin.

Preferably, the mixing step is performed using the packaging and dispensing device, by releasing the oily phase composition, which is transparent, from the pipette to the container comprising the aqueous phase composition, which is transparent too. When mixing, the resulting composition (i.e. composition of the invention) becomes white or milky, and is then ready to use.

The invention will be better understood after studying the following non-limitative examples that form preferred embodiments of the method conforming to the invention.

Unless mentioned otherwise, quantities in the following examples are expressed as a percent by weight of the total weight of the composition (%w/w) .

Examples

Example 1 : tests with different ingredients

Formulas A to J of table 1 below were prepared as follows:

1. the water phase is prepared by mixing all the ingredients of the water phase at 70℃, until forming a homogenous mixture;

2. the oil phase is prepared by mixing all the ingredients of the oil phase at 60℃, until forming a homogenous mixture;

3. the oil phase and the water phase are manually mixed, with a weight ratio of 6: 94 at room temperature.

Formulas A, B, C, D and H are according to the invention.

Formulas A1, D1, E, F, G, I and J are comparative.

Besides, a further batch of each oil phase for each formula was prepared separately.

Viscosity was measured as follows:

The viscosity is generally measured at 25℃ with a viscosimeter RHEOMAT RM 180 with Mobile 2 adapted to the viscosity of the formula to be tested (mobile is chosen for having a measure between 10 and 90 for UD, i.e. Unit Deviation) , the measure being made after 10mn rotating the mobile inside the composition, with a shear of 200s ^-1. The UD values may then be converted in Poises (1 Poise= 0.1Pa. s) with a correspondence table.

More preferably, the composition contains a gelified aqueous phase.

Moreover, the following parameters of the mixtures were measured:

- the aspect of the mixture phase was evaluated after one week at 65℃, and

- the aspect of the mixture phase was evaluated after two weeks at 45℃.

The following parameters of each oil phase were measured:

- the color of the oil phase was evaluated after one week at 65℃, and

- the color of the oil phase was evaluated after two months at 45℃.

Results are indicated in table 2 above.

It appears that formulas A, B, C, D and H are the only ones which are stable under both tested conditions, while at the same time being showing an oil phase which is transparent.

Comparative formula A1 is stable but shows an oil phase of little yellow.

Comparative formulas D1, E and F demulsify after one week at 65℃, whereas the oil phase of comparative formula G turns brown.

Finally, comparative formulas I and J demulsify and show emulsion floats.

Thus, the formulas of the invention, which comprise at least acetyl tributyl citrate, are the only ones which are stable and show transparency of the oil phase. They are the single formulas which are able to ensure stability of both the active (phenylethyl resorcinol) and the emulsion.

Example 2 : Composition of the invention (milky fresh composition)

A milky fresh composition was prepared by mixing the following oil and aqueous phases:

Oil phase: this oily phase is transparent

Aqueous phase:

The composition of the invention is obtained by mixing the oily phase with the aqueous phase. It has a milky appearance, and has the following final formula:

Claims

Cosmetic composition comprising, in an oily phase:

a) an anti-ageing and/or antioxidant and/or depigmenting agent;

b) at least one compound selected from esters of citric acid corresponding to formula (I) :

in which R1, R2 and R3, which are identical or different, each represent H or a linear, branched or cyclic, saturated or unsaturated C1-C30 alkyl chain,

wherein at least one of R1, R2 and R3 is different from H, and

R4 represents H or a group R'4-CO-, in which R'4 represents a linear, branched or cyclic, saturated or unsaturated C1-C8 alkyl group; and

c) at least one surfactant chosen from oxyethylene fatty acid and polyol esters, having an HLB of from 10 to 14.
Cosmetic composition in the form of an oil-in-water emulsion, comprising:

- an oily phase comprising:

a) an anti-ageing and/or antioxidant and/or depigmenting agent;

b) at least one compound selected from esters of citric acid corresponding to formula (I) :

in which R1, R2 and R3, which are identical or different, each represent H or a linear, branched or cyclic, saturated or unsaturated C1-C30 alkyl chain,

wherein at least one of R1, R2 and R3 is different from H, and

R4 represents H or a group R'4-CO-, in which R'4 represents a linear, branched or cyclic, saturated or unsaturated C1-C8 alkyl group; and

c) at least one surfactant chosen from oxyethylene fatty acid and polyol esters, having an HLB of from 10 to 14, and

- an aqueous phase comprising water,

wherein the oily phase is dispersed in the aqueous phase.
Composition according to claim 1 or 2, wherein the surfactant c) is chosen from oxyethylenated glyceryl triisostearate (20 OE) and oxyethylenated sorbitan trioleate (20 OE) .
Composition according to any one of claims 1 to 3, wherein the compound b) is chosen from acetyl tributyl citrate, triethyl citrate, tributyl citrate, triethyl acetylcitrate and triethyl-2-hexyl acetylcitrate.
Composition according to any one of claims 1 to 4, wherein the anti-ageing and/or antioxidant and/or depigmenting agent a) is a depigmenting agent, preferably a resorcinol derivative represented by formula (I) :

wherein

R ₁ independently denotes -A-B where A represents a single bond, a C ₁-C ₆ alkylene group, a C ₆-C ₁₂ arylene group, or a C ₁-C ₆ alkylene-C ₆-C ₁₂ arylene group, and B represents a halogen atom, -OH, -COH, -COOH, -CONH ₂, -NH ₂, a C ₁-C ₆ alkyl group, a C ₁-C ₆ alkoxy group, a C ₁-C ₆ acyl group, a carbocyclic group, preferably an aryl group, or heterocyclic group, preferably a non-aromatic heterocyclic group, each of which may be substituted with at least one substituent selected from the group consisting of a hydroxyl group, a carboxyl group, a C ₁-C ₆ alkyl group, a C ₁-C ₆ alkylene-OH, an amino group, -CONH ₂, -CONH-C _1-6 alkyl group and a C ₁-C ₆ alkoxy group;

x is an integer of 1 to 4, preferably 1 to 3, more preferably 1 or 2 and even more preferably 1; and

R ₂ and R ₃ independently denote a hydrogen atom, a C ₁-C ₆ alkyl group, or a C ₁-C ₆ acyl group,

or a salt, a solvate, an optical isomer thereof, or a racemate thereof.
Composition according to any one of claims 1 to 5, wherein the anti-ageing and/or antioxidant and/or depigmenting agent a) is chosen from resorcinol, butyl resorcinol and phenylethyl resorcinol.
Composition according to any one of claims 2 to 6, wherein the surfactant c) is present in an amount of less than 1%by weight of the total weight of the composition, preferably from 0.1%to 0.9%by weight, preferably from 0.2%to 0.8%by weight.
Composition according to any one of claims 2 to 7, wherein the anti-ageing and/or antioxidant and/or depigmenting agent a) is present in an amount of less than 1%by weight of the total weight of the composition, preferably from 0.1%to 0.9%by weight, preferably from 0.2%to 0.8%by weight.
Composition according to any one of claims 2 to 8, wherein the compound b) is present in an amount of from 1%to 10%by weight of the total weight of the composition, preferably from 2%to 8%by weight, preferably from 3%to 5%by weight.
Composition according to any one of claims 1 to 9, wherein the oily phase further comprises a solvent chosen from lipophilic derivatives of amino acids, preferably isopropyl lauroyl sarcosinate.
Composition according to any one of claims 2 to 10, wherein the aqueous phase further comprises at least one ingredient chosen from:

- non-ionic surfactants which are polyoxyethylenated (from 1 to 40 EO) and polyoxypropylenated (from 1 to 30 PO) alkyl C16-C30 ethers with an HLB value of 13.0 or less;

- oxyalkylenated sugar ethers, such as oxyethylenated methyl glucose ethers;

- hydrophilic gelling agents, preferably chosen from carboxyvinyl polymers modified or not, polymers of natural origin such as xanthan gum, and homopolymers and copolymers with an acrylamido propane sulfonic acid base; and

- their mixtures.
Kit comprising:

- a first container comprising the composition according to any one of claims 1 or 3 to 10, and

- a second container comprising an aqueous phase composition comprising water.
Kit according to claim 12, wherein the first container is a pipette.
Kit according to claim 12 or 13, wherein it is a packaging and dispensing device comprising:

- a container for storing the aqueous phase composition, said container comprising an opening;

- a pipette removably inserted in the container through the opening, said pipette extending along an axis and having a first dispensing end and a second end;

- a plug removably assembled to the dispensing end of the pipette, said assembled pipette and plug defining an inner compartment for temporarily storing the oily phase composition isolated from the aqueous phase composition; and

- a pressure supply device comprising :

- a support assembled to the second end of the pipette;

- a compressible chamber in fluid communication with the second end of the pipette; and

- a first pressure member able to move relative to the support, between a first and a second configurations, so as to lessen a volume of the compressible chamber, thereby increasing a pressure in the inner compartment;

wherein the pressure supply device comprises locking elements for maintaining the first pressure member in the second configuration with an increased pressure in the inner compartment.
Cosmetic method for caring the skin, comprising the following steps:

- mixing the composition according to any one of claims 1 or 3 to 10 with an aqueous phase composition comprising water, in order to obtain a mixture, and

- applying said mixture to said skin.