WO2020126732A1

WO2020126732A1 - Composition comprising a monoglyceride, a tartaric ester of monoglyceride and a salicylic acid compound

Info

Publication number: WO2020126732A1
Application number: PCT/EP2019/084595
Authority: WO
Inventors: Phi-Oanh DINH; Marie-Lise CHIRON
Original assignee: L'oreal
Priority date: 2018-12-20
Filing date: 2019-12-11
Publication date: 2020-06-25
Also published as: FR3090335B1; FR3090335A1

Abstract

The invention relates to a composition, preferably a cosmetic composition, comprising at least one aqueous phase, at least one monoglyceride, at least one tartaric ester of monoglyceride, and at least one salicylic acid compound. The invention also relates to a cosmetic treatment method in which a composition as defined according to the invention is applied to keratin materials, and in particular to the skin. Introducing salicylic acid compounds into a composition comprising at least one aqueous phase, at least one monoglyceride, and at least one tartaric ester of monoglyceride not only does not destabilize them but also enables the skin absorption of these active ingredients to be improved and hence the effectiveness thereof to be increased.

Description

Title: Composition comprising a monoglyceride, a tartaric ester of

monoglyceride and a salicylic acid compound

Technical field

[0001 ] The invention relates to a composition, preferably a cosmetic composition, comprising at least one monoglyceride, at least one tartaric ester of monoglyceride, and at least one salicylic acid compound. More particularly, the invention relates to a composition, preferably a cosmetic composition, comprising at least one aqueous phase, at least one monoglyceride, at least one tartaric ester of monoglyceride, and at least one salicylic acid compound.

[0002] It is known practice to use salicylic acid compounds in topical compositions, notably cosmetic or dermatological compositions for example as a keratolytic agent for treating acne or as an anti-aging agent. Thus, documents FR-A-2 581 542 and EP- A-378 936 describe such compounds.

[0003] Salicylic acid compounds are of great interest in view of the biological effects thereof on the skin, specifically on the main clinical signs of skin aging, which are fine lines and wrinkles, the disorganization of the“grain” of the skin, changes in the skin complexion and a loss of firmness and tone of the skin. However, the use of these compounds presents a problem in that these compounds are in crystalline form and are insoluble or poorly soluble in water and in the fatty substances conventionally used in the fields of cosmetics and dermatology. Thus, introduced in unmodified form into topical compositions, they do not solubilize and remain in the crystalline state, making the use of the composition containing them ineffective for treating the skin.

[0004] These compounds can be solubilized in lower alcohols such as ethanol or isopropanol or solvents such as octyldodecanol, certain glycols, and short-chain fatty alcohols (less than C12). However, lower alcohols have the disadvantage of drying out and irritating the skin; it is thus preferable to avoid their use in body and/or facial care products. Moreover, these solubilizers can only be introduced in small quantities, otherwise the cosmetic qualities (softness) and stability of the compositions containing them may be impaired. [0005] Furthermore, the use of salicylic acid compounds in conventional oil-in-water emulsions tends to destabilize the emulsion, which then exhibits a phase separation of oil at the surface. The oil globules dispersed in the aqueous phase have a coarse appearance, rendering the emulsion non-homogeneous.

[0006] There is thus a need for compositions, notably cosmetic compositions, which are capable of conveying potentially high concentrations of salicylic acid compounds while at the same time being free of the undesirable effects described above.

[0007] It would therefore be particularly advantageous to be able to maximize the performance of the salicylic acid compounds, notably by having galenic formulas containing a high concentration of this active ingredient and exhibiting good cosmetic qualities.

[0008] There is also a need for compositions containing salicylic acid compounds which are stable over time.

[0009] For obvious reasons it would also be most particularly advantageous for these compositions to be capable of improving the effectiveness of these salicylic acid compounds.

Subject of the invention

[0010] A subject of the present invention is to propose, specifically, a novel galenic formulation of salicylic acid compounds that satisfies the expectations set forth above.

[001 1 ] More specifically, a subject of the invention is a composition, notably a cosmetic composition, comprising at least one monoglyceride, at least one tartaric ester of monoglyceride, and at least one salicylic acid compound.

[0012] The composition advantageously comprises an aqueous phase.

[0013] A composition according to the invention preferably contains a coagel phase.

[0014] Aqueous systems based on a combination of monoglyceride and a tartaric ester of monoglycerides are commonly known as coagels and have been used in food applications for some years to produce light margarines. A coagel generally comprises a three-dimensional matrix containing a continuous aqueous phase. A coagel is a complex system generally constituted of crystals of fatty substances percolated in an aqueous phase. Such a three-dimensional architecture can contain up to 98% of an aqueous phase.

[0015] These systems have been the subject of important structural studies. The following articles may be cited, inter alia: Liquid Crystalline Phases in the Structuring of Food Products, 1998, Lebensmittel-Wissenschaft und -Technologie, 31 , 387-396; Investigation of the Gel to Coagel Phase Transition in Monoglyceride-Water Systems (Langmuir 1998, 14, 5757-5763); Lipid organization and dynamics of the monostearoylglycerol-water system. A 2H NMR study (Chemistry and Physics of Lipids 109 (2001 ) 15-28); Rheological Characterization, Crystallization, and Gelation, Behavior of Monoglyceride Gels (Journal of Colloid and Interface Science 249, (2002) 412-422).

[0016] The use of these aqueous systems based on a combination of monoglyceride and a tartaric ester of monoglycerides, commonly known as coagels, for a cosmetic application is known from patent applications FR 3 007 643 and FR 3 007 644.

[0017] Introducing salicylic acid compounds into these systems not only does not destabilize them but also enables the skin absorption of these active ingredients to be improved and hence the effectiveness thereof to be increased.

[0018] The composition thus obtained is stable on storage. For example, no microscopic or macroscopic changes are observed at the end of six months or even one year at ambient temperature. Moreover, the composition has good cosmetic properties, notably good sensory properties and good skin elasticity.

[0019] In addition, the present invention enables the quantity of salicylic acid compounds introduced into the cosmetic compositions to be increased.

[0020] The compositions according to the invention preferably take the form of creams, foams or sticks. It is important to note that, when observed under a microscope, the compositions according to the invention, if they have the appearance of cosmetic creams, have a different structure from conventional emulsions, which are characterized for example by a regular layer of droplets. More specifically, the compositions according to the invention are characterized by a strongly birefringent appearance in polarized light, which is typical of their semi-crystalline nature. [0021 ] This semi-crystalline structure may be characterized in particular by X-ray diffraction at a temperature lower than the melting point of the lamellar phases. This technique is well known to those skilled in the art and is described at length in the literature.

Definitions

[0022] The composition according to the invention is intended for topical application and thus contains a physiologically acceptable medium. The term“physiologically acceptable medium” means here a medium that is compatible with keratin materials.

[0023] In the context of the present invention, the term“keratin material” notably means the skin, the scalp, keratin fibers such as the eyelashes, the eyebrows, head hair, body hair, the nails, and mucous membranes such as the lips, and more particularly the skin (body, face, area around the eyes, eyelids).

[0024] In the text hereinbelow, the expression "at least one" is equivalent to "one or more" and, unless otherwise indicated, the limits of a range of values are included in that range.

[0025] Unless otherwise indicated, the percentages of the constituents are expressed on a weight basis relative to the total weight of the composition.

Monoglyceride

[0026] A monoglyceride, or monoacylglycerol (MAG) is a glyceride formed by a fatty acid residue linked to a glycerol residue by an ester bond. They can be divided into two groups: 1 -monoacylglycerols and 2-monoacylglycerols, depending on whether the acyl group is in position 1 or 2 on the glycerol residue.

[0027] According to a particular embodiment, the composition contains as monoglyceride one or more monoglycerides comprising a saturated or unsaturated alkyl chain containing from 12 to 22 carbon atoms.

[0028] The monoglyceride preferably comprises a saturated or unsaturated alkyl chain containing 16 or 18 carbon atoms.

[0029] In the present case, interest is focused most particularly on 1 - monoacylglycerols, such as those of the following formula (example with C18):

[0030] [Chem.1 ]

[0031 ] The length of the fatty acid chain may range from C12 to C22. Esters of C16 or C18 monoglycerides are chosen by preference.

[0032] The starting material used is important to the extent that the monoglycerides used enable a coagel phase to be formed. In particular, monoglycerides containing less than 10% residual diglycerides are used. Stearates of monoglycerides are preferably used, for example those sold under the name DIMODAN HP by DANISCO or those sold under the name TEGIN 90 by EVONIK GOLDSCHMIDT.

[0033] The monoglyceride content of the compositions according to the invention generally ranges from 1 % to 20%, preferentially from 2 to 10%, and very preferentially from 3 to 8% by weight, relative to the total weight of said composition.

Tartaric ester of fatty acid monoglycerides

[0034] Tartaric esters of fatty acid monoglycerides are generally obtained by grafting a tartaric residue in position 3 of the glycerol residue of a 1 -monoacylglycerol.

[0035] The length of the fatty acid chain may range from C12 to C22, but esters of C16 or C18 monoglycerides will be chosen by preference. The tartaric ester of monoglyceride is preferably a diacetyl tartaric ester of monoglyceride comprising a saturated or unsaturated alkyl chain containing from 12 to 22 carbon atoms and preferably containing 16 or 18 carbon atoms.

[0036] More particularly, dialkyl (C1-C4) tartaric esters of C12 to C22 acid monoglycerides will be used. In the present case, interest is focused most particularly on diacetyl tartaric esters of C18 monoglycerides such as those of the following formula:

[0037] [Chem.2] ^. "

[0038] The invention covers the various isomers of tartaric acid and mixtures thereof, including racemic mixtures.

[0039] These ingredients and the uses thereof are described on pages 88 to 95 of the brochure Functional Ingredients for Food, published by DANISCO and available on the site http://www.danisco.com/.

[0040] These esters may be chosen from a tartaric ester of fatty acid mono- and diglycerides (additive E472d) and a monoacetyl tartaric ester of fatty acid mono- and diglycerides (additive E472e). Esters of monoglycerides and diglycerides having a purity in the order of 80% and more are primarily sought.

[0041 ] Mention may be made in particular of the product sold under the name PANODAN A2020 MB by DANISCO.

[0042] The content of tartaric ester of monoglyceride in the compositions according to the invention generally ranges from 0.05% to 2%, preferentially from 0.1 % to 1 %, and very preferentially from 0.1 % to 0.5% by weight, relative to the total weight of said composition. Typically, a content of tartaric ester of monoglyceride ranging from 0.2 to 0.5% by weight, relative to the total weight of said composition, is used.

Salicylic acid compounds

[0043] The salicylic acid compound present in the composition according to the invention is advantageously chosen from salicylic acid and the derivatives of the following formula:

[0044] [Chem.3] in which:

- the radical R denotes a linear, branched or cyclic saturated aliphatic chain

containing from 2 to 22 carbon atoms; an unsaturated chain containing from 2 to 22 carbon atoms, containing one or more double bonds that may be conjugated; an aromatic nucleus linked to the carbonyl radical directly or via saturated or

unsaturated aliphatic chains containing from 2 to 7 carbon atoms; said groups possibly being substituted with one or more substituents, which may be identical or different, chosen from (a) halogen atoms, (b) the trifluoromethyl group, (c) hydroxyl groups in free form or esterified with an acid containing from 1 to 6 carbon atoms, or (d) a carboxyl function in free form or esterified with a lower alcohol containing from 1 to 6 carbon atoms;

- R’ is a hydroxyl group;

- and also salts thereof derived from a mineral or organic base.

[0045] Preferentially, the radical R denotes a linear, branched or cyclic saturated aliphatic chain containing from 3 to 1 1 carbon atoms; an unsaturated chain containing from 3 to 17 carbon atoms and comprising one or more conjugated or unconjugated double bonds; said hydrocarbon-based chains possibly being substituted with one or more substituents, which may be identical or different, chosen from (a) halogen atoms, (b) the trifluoromethyl group, (c) hydroxyl groups in free form or esterified with an acid containing from 1 to 6 carbon atoms, or (d) a carboxyl function in free form or esterified with a lower alcohol containing from 1 to 6 carbon atoms; and salts thereof obtained by salification with a mineral or organic base.

[0046] The derivatives that are more particularly preferred are those in which the radical R is a C3-C1 1 alkyl group. [0047] Among the salicylic acid derivatives that are particularly preferred, mention may be made of 5-n-octanoylsalicylic acid (or capryloylsalicylic acid); 5-n- decanoylsalicylic acid; 5-n-dodecanoylsalicylic acid; 5-n-heptanoylsalicylic acid, and the corresponding salts thereof.

[0048] The salicylic acid compound is advantageously chosen from salicylic acid and 5-n-octanoylsalicylic acid.

[0049] The salts of the derivatives of formula [Chem.3] may be obtained by salification with a mineral or organic base. Examples of mineral bases that may be mentioned include alkali metal or alkaline-earth metal hydroxides, for instance sodium hydroxide or potassium hydroxide, or ammonia.

[0050] Among the organic bases, mention may be made of amines and alkanolamines. Quaternary salts, for instance those described in patent FR 2 607 498, are particularly advantageous.

[0051 ] The derivatives of formula [Chem.3] that may be used according to the invention are described in patents US 6 159 479 and US 5 558 871 , FR 2 581 542, FR 2 607 498, US 4 767 750, EP 378 936, US 5 267 407, US 5 667 789, US 5 580 549 and EP-A-570 230.

[0052] The salicylic acid compound(s) as defined previously may be present in the composition according to the invention in a content ranging from 0.01 % to 2% by weight, preferably from 0.05% to 1 .5% by weight and preferentially from 0.1 % to 1 % by weight, relative to the total weight of the composition.

Aqueous phase

[0053] According to a particular embodiment, the composition according to the invention comprises an aqueous phase.

[0054] According to a particular embodiment, the composition according to the invention includes an amount of water of at least 40% by weight, preferably ranging from 40 to 95% by weight and better still from 50 to 90% by weight, relative to the total weight of the composition.

[0055] The water used may be sterile demineralized water and/or a floral water such as rose water, cornflower water, chamomile water or lime blossom water, and/or a natural spring water or mineral water, for instance: Vittel water, Vichy basin water, Uriage water, Roche Posay water, Bourboule water, Enghien-les-Bains water, Saint Gervais-les-Bains water, Neris-les-Bains water, Allevar-les-Bains water, Digne water, Maizieres water, Neyrac-les-Bains water, Lons-le-Saunier water, Eaux Bonnes water, Rochefort water, Saint Christau water, Fumades water, Tercis-les-Bains water and Avene water. The aqueous phase may also comprise reconstituted spring water, i.e. a water containing trace elements such as zinc, copper, magnesium, etc., reconstituting the characteristics of a spring water.

[0056] The aqueous (or hydrophilic) phase of the composition according to the invention may also contain any water-soluble or water-dispersible additive. Water- soluble additives that may especially be mentioned are polyols comprising from 2 to 8 carbon atoms. The term “polyol” should be understood as meaning any organic molecule containing at least two free hydroxyl groups. Examples of polyols that may be mentioned include glycerol, glycols, for instance butylene glycol, propylene glycol, isoprene glycol, dipropylene glycol, hexylene glycol, polyethylene glycols and polypropylene glycol. According to a particular embodiment of the invention, the polyol is chosen from glycerol and hexylene glycol. Preferably, the polyol is glycerol.

[0057] Water-soluble additives that may also be mentioned include primary alcohols, i.e. an alcohol containing from 1 to 6 carbon atoms, such as ethanol and isopropanol. It is preferably ethanol. The addition of such an alcohol may notably be suitable when the composition according to the invention is used as a product for the body or the hair.

[0058] The amount of water-soluble or water-dispersible additives in the composition of the invention may range, for example, from 0 to 50% by weight, preferably from 0.5% to 30% by weight and even more preferentially from 2 to 20% by weight, relative to the total weight of the composition.

[0059] According to a particular embodiment of the invention, the composition has a pH of between 4 and 6, ideally close to 5, which makes it possible to optimize its stability.

Hydrophilic gelling agent

[0060] According to a particular embodiment of the invention, the composition comprises at least one hydrophilic gelling agent. In particular, aqueous gelling agents and structuring agents conventionally used by those skilled in the art will be used. These gelling agents may be particulate or non-particulate, synthetic or of natural origin.

[0061 ] Hydrophilic gelling agents that may be mentioned include, for example, carboxyvinyl polymers, such as the Carbopols (Carbomers) and the Pemulens (acrylate/C 10-C30 alkyl acrylate copolymer); polyacrylamides, such as, for example, the crosslinked copolymers sold under the names Sepigel 305 (CTFA name: polyacrylamide/C13-14 isoparaffin/Laureth 7) or Simulgel 600 (CTFA name: acrylamide/sodium acryloyldimethyl taurate copolymer/isohexadecane/polysorbate 80) by the company Seppic 2-acrylamido-2-methylpropanesulfonic acid polymers and copolymers, optionally crosslinked and/or neutralized, for instance poly(2-acrylamido- 2-methylpropanesulfonic acid) sold by the company CLARIANT under the trade name Hostacerin AMPS (CTFA name: ammonium polyacryloyldimethyl taurate) or SIMULGEL 800 sold by the company SEPPIC (CTFA name: sodium polyacryloyldimethyl taurate/polysorbate 80/sorbitan oleate); copolymers of 2- acrylamido-2-methylpropanesulfonic acid and hydroxyethyl acrylate, for instance SIMULGEL NS and SEPINOV EMT 10 sold by the company SEPPIC; cellulose derivatives such as hydroxyethyl cellulose; polysaccharides and especially gums such as xanthan gum; and mixtures thereof.

[0062] According to an embodiment, the hydrophilic gelling agent comprises at least one xanthan gum.

[0063] According to a preferred embodiment, the hydrophilic gelling agent comprises at least one acrylamide/sodium acrylamido-2-methylpropanesulfonate copolymer, optionally in inverse emulsion. An inverse emulsion such as Simulgel 600 (INCI name: acrylamide/sodium acryloyldimethyl taurate copolymer/isohexadecane/polysorbate 80) from Seppic may be used.

[0064] According to an embodiment, the hydrophilic gelling agent is a mixture of one or more of the compounds listed above.

[0065] According to an embodiment, the hydrophilic gelling agent is chosen from xanthan gum, copolymers of acrylamide and sodium acryloyldimethyl taurate and any mixture thereof. [0066] According to an embodiment, the active material content of the hydrophilic gelling agent ranges from 0.1 % to 5%, advantageously from 1 % to 3% by weight, relative to the total weight of the composition.

Oily phase

[0067] The composition according to the invention may also comprise an oily phase.

[0068] According to a particular embodiment, the composition of the invention comprises at least one oil chosen from Guerbet alcohols and derivatives thereof, and lipophilic amino acid derivatives.

[0069] Introducing these oils into the composition in accordance with the invention has the advantage of improving the homogeneity and stability of the composition, especially if the concentration of salicylic acid compounds is high, particularly if it is greater than 0.3% by weight of the total weight of the composition.

[0070] Thus, according to a preferred embodiment of the invention, the composition comprises at least one salicylic acid compound in a quantity greater than 0.3% by weight of the total weight of the composition and at least one oil chosen from Guerbet alcohols and derivatives thereof, and lipophilic amino acid derivatives.

[0071 ] The Guerbet alcohol derivative(s) may be, for example, Guerbet alcohol esters.

[0072] Guerbet alcohols are obtained by converting an aliphatic primary alcohol into a beta-alkylenated alcohol dimer via the following chemical reaction:

[0073] [Chem.4]

in which R is, in particular, a C8-C30 alkyl radical, preferably a C12-C24 alkyl radical and even more preferentially a C16-C20 alkyl radical.

[0074] This reaction requires the presence of a catalyst such as alkali metal hydroxides or alkali metal alkoxides, such as Raney nickel, and high temperatures. [0075] As Guerbet alcohols or Guerbet alcohol derivatives, mention may be made especially of octyldodecanol and octyldodecanol esters such as octyldodecyl myristate. Mention may be made in particular of octyldodecanol, such as the product sold under the name EUTANOL G by the company COGNIS (BASF) and the octyldodecyl myristate sold under the name DUB MOD by the company GATTEFOSSE.

[0076] The lipophilic amino acid derivative(s) that may be used in the composition of the invention may be chosen from the amino acid esters of the following formula:

[0077] [Chem.5]

R'1(CO)N{R^,2 l(R^,3)(CH2)n(CO)OR^,4 in which: n is an integer equal to 0, 1 or 2,

R’1 represents a linear or branched C5 to C21 alkyl or alkenyl radical,

R’2 represents a hydrogen atom or a C1 to C3 alkyl radical,

R’3 represents a radical chosen from the group formed by a hydrogen atom, a methyl group, an ethyl group and a linear or branched C3 or C4 alkyl radical,

R’4 represents a linear or branched C1 to C10 alkyl radical, a linear or branched C2 to C10 alkenyl radical or a sterol residue.

[0078] These amino acid esters and the method for synthesizing them are described in patent applications EP 1 044 676 and EP 0 928 608 from the company AJINOMOTO CO.

[0079] In formula [Chem.5] described above, the group R’1 (CO)- is an acyl group of an acid chosen preferably from the group formed by capric acid, lauric acid, myristic acid, palmitic acid, stearic acid, behenic acid, linoleic acid, linolenic acid, oleic acid, isostearic acid, 2-ethylhexanoic acid, coconut oil fatty acids, palm kernel oil fatty acids and hydrogenated palm kernel oil fatty acids. These fatty acids may also contain a hydroxyl group. Even more preferably, it will be lauric acid.

[0080] The -N(R'2)CFI(R'3)(CFI2)n(CO)- part of the amino acid ester is preferably chosen from the following amino acids: glycine, alanine, valine, leucine, isoleucine, serine, threonine, proline, hydroxyproline, b-alanine, aminobutyric acid, aminocaproic acid, sarcosine, or N-methyl-B-alanine.

[0081 ] Even more preferably, it will be sarcosine.

[0082] The part of the amino acid esters corresponding to the group OR’4 may be obtained from alcohols chosen from the group formed by methanol, ethanol, propanol, isopropanol, butanol, tert-butanol, isobutanol, 3-methyl-1 -butanol, 2-methyl-1 -butanol, fusel oil, pentanol, hexanol, cyclohexanol, octanol, 2-ethylhexanol, decanol, lauryl alcohol, myristyl alcohol, cetyl alcohol, cetostearyl alcohol, stearyl alcohol, oleyl alcohol, behenyl alcohol, jojoba alcohol, 2-hexadecyl alcohol, 2-octyldodecanol alcohol and isostearyl alcohol.

[0083] These amino acid esters may be obtained in particular from natural sources of amino acids. In this case, the amino acids originate from the hydrolysis of natural plant proteins (oat, wheat, soybean, palm or coconut) and then necessarily lead to mixtures of amino acids that subsequently need to be esterified and then N-acylated. The preparation of such amino acids is more particularly described in patent application FR 2 796 550, which is incorporated herein by reference.

[0084] The amino acid ester more particularly preferred for its use in the present invention is isopropyl N-lauroylsarcosinate of formula:

[0085] [Chem.6]

CH3-(CH2)10CO-N(CH3)-CH2-COO- CH2-( CH3)2.

[0086] This lipophilic derivative is sold in particular under the name ELDEW SL-205 by AJINOMOTO.

[0087] The oil(s) chosen from Guerbet alcohols and derivatives thereof and lipophilic amino acid derivatives may be present in the composition according to the invention in a content ranging from 0.03% to 15% by weight and preferably from 0.1 % to 7% by weight, relative to the total weight of the composition.

[0088] These quantities depend on the quantity of salicylic acid compounds present in the composition and are adjusted so as to solubilize them without destabilizing the coagel structure of the composition. [0089] For example, to dissolve 5-n-octanoylsalicylic acid and maintain the stability of the coagel, octyldodecanol or isopropyl N-lauroylsarcosinate should preferentially be used, and very preferentially a mixture of these two oils.

[0090] In particular, the quantity just necessary to solubilize the 5-n-octanoylsalicylic acid may be introduced.

[0091 ] According to a first embodiment, the composition in accordance with the invention comprises 5-n-octanoylsalicylic acid and octyldodecanol, with a ratio of 5-n- octanoylsalicylic acid to octyldodecanol of between 1 :8 and 1 : 14, preferably between 1 :9 and 1 : 1 1 and very preferentially 1 : 10.

[0092] According to a second embodiment, the composition in accordance with the invention comprises 5-n-octanoylsalicylic acid and isopropyl N-lauroylsarcosinate, with a ratio of 5-n-octanoylsalicylic acid to isopropyl N-lauroylsarcosinate of between 1 :2 and 1 :4, preferably between 1 :2.5 and 1 :3.5 and very preferentially 1 :3.

[0093] When the composition in accordance with the invention comprises a quantity of 5-n-octanoylsalicylic acid greater than or equal to 0.5, it preferably comprises a mixture of octyldodecanol and isopropyl N-lauroylsarcosinate in order to maintain the stability of the coagel and to solubilize the 5-n-octanoylsalicylic acid.

[0094] Preferentially, the ratio of 5-n-octanoylsalicylic acid to isopropyl N- lauroylsarcosinate is between 1 and 2, preferably 1 .5; the ratio of 5-n-octanoylsalicylic acid to octyldodecanol is between 3 and 8, preferably 5; and the ratio of isopropyl N- lauroylsarcosinate to octyldodecanol is between 2 and 5, preferably 3.3. The ratio of 5-n-octanoylsalicylic acid to isopropyl N-lauroylsarcosinate to octyldodecanol is preferably 2:3: 10; in other words, 0.75% isopropyl N-lauroylsarcosinate and 2.5% octyldodecanol are used to dissolve 0.5% 5-n-octanoylsalicylic acid, while 1 .5% isopropyl N-lauroylsarcosinate and 5% octyldodecanol are used to dissolve 1 % 5-n- octanoylsalicylic acid,

[0095] According to another particular embodiment, the composition of the invention comprises at least one oil chosen from silicone oils. The oil(s) chosen from silicone oils that may be used in the context of the invention may be volatile or non-volatile.

[0096] The use of these silicone oils enables the sensory properties of the composition to be improved while maintaining good stability of the coagel. [0097] The term“silicone oil” means an oil comprising at least one silicon atom, and especially comprising Si-0 groups.

[0098] For the purposes of the invention, the term "volatile oil" means any oil that is capable of evaporating on contact with the skin in less than one hour, at ambient temperature and atmospheric pressure. The volatile oil is a volatile cosmetic compound, which is liquid at ambient temperature, especially having a non-zero vapor pressure, at ambient temperature and atmospheric pressure, especially having a vapor pressure ranging from 0.13 Pa to 40,000 Pa (10^-3 to 300 mmFIg), in particular ranging from 1 .3 Pa to 13,000 Pa (0.01 to 100 mmFIg) and more particularly ranging from 1 .3 Pa to 1300 Pa (0.01 to 10 mmFIg).

[0099] According to a particular embodiment of the invention, the composition comprises at least one linear silicone oil. The linear silicone oils are preferably polyorganosiloxanes comprising alkylsiloxane repeat units, the alkyl groups preferably comprising from 1 to 6 carbon atoms and preferably being unsubstituted.

[00100] In particular, the linear silicone oils are chosen from polydimethylsiloxanes (INCI name: dimethicone), preferably of formula:

[00101 ] [Chem.7]

in which x is an integer chosen so as to have a fluid compound.

[00102] As linear silicone oils that may be used in the composition according to the invention, examples that may be mentioned include the PDMSs DC 200 Fluid 5 cSt, 10 cSt and 350 cSt sold by the company Dow Corning or the one sold by the company Wacker under the name Wacker Belsil DM 10.

[00103] When the composition comprises at least one silicone oil, the content thereof is generally between 1 % and 20% by weight, preferably between 2% and 14% by weight of the total weight of the composition. [00104] The composition according to the invention may comprise at least one additional oil different from the oils previously described.

[00105] As oils that may more particularly be used in the composition of the invention, examples that may be mentioned include:

[00106] - hydrocarbon-based oils of animal origin, such as perhydrosqualene (or squalane);

[00107] - hydrocarbon-based oils of plant origin, such as liquid fatty acid triglycerides 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 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 Cremer Oleo, jojoba oil and shea butter oil;

[00108] - synthetic esters and ethers, especially of fatty acids, for instance the oils of formulae R1 COOR2 and R10R2 in which R1 represents the residue of a fatty acid 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;

[00109] - linear or branched hydrocarbons, of mineral or synthetic origin, such as mineral oils (mixture of hydrocarbon-based oils derived from petroleum; INCI name: Mineral oil), volatile or non-volatile liquid paraffins, and derivatives thereof, petroleum jelly, polydecenes, isohexadecane, isododecane, hydrogenated isoparaffin such as Parleam® oil sold by the company NOF Corporation (INCI name: Hydrogenated Polyisobutene);

[00110] - fluoro oils, such as those which are partially hydrocarbon-based and/or silicone-based, for instance those described in document JP-A-2 295 912; [001 1 1 ] - ethers such as dicapryl ether (CTFA name: Dicaprylyl ether); and C12-C15 fatty alcohol benzoates (Finsolv TN from FINETEX);

[001 12] - mixtures thereof.

[001 13] The compositions according to the present invention may also include conventional cosmetic adjuvants chosen in particular from the additives typically used in cosmetics: pigments, mineral fillers, colorants, active ingredients, etc.

[001 14] The compositions according to the present invention may also include biological active ingredients (in particular, anti-aging, oily skin, lightening, anti-blemish, antiperspirant and antioxidant agents), UV filters, filmogenic polymers, diffusing fillers, oils, fatty substances such as fatty alcohols for example, moisturizers, emollients, etc.

[001 15] Needless to say, a person skilled in the art will take care to select the optional adjuvant(s) added to the composition according to the invention such that the advantageous properties intrinsically associated with the composition in accordance with the invention are not, or are not substantially, impaired by the envisaged addition.

[001 16] According to an embodiment, the method for synthesizing a composition according to the invention comprises the following steps:

[001 17] (i) mixing at least one monoglyceride, at least one tartaric ester of fatty acid monoglyceride and at least water;

[001 18] (ii) optionally raising the temperature of said mixture;

[001 19] (iii) maintaining the temperature of said mixture over time at a temperature above ambient temperature;

[00120] (iv) lowering the temperature of said mixture, optionally by adding a liquid at ambient temperature; and

[00121 ] (v) optionally adding a hydrophilic gelling agent.

[00122] In accordance with an embodiment according to the invention, the temperature of the mixture during step (iii) is between 50 and 80°C, advantageously between 55 and 65°C.

[00123] In accordance with an embodiment according to the invention, the length of time for which the temperature is maintained during step (iii) is between 10 minutes and 2 hours, advantageously between 30 minutes and one hour. [00124] In accordance with an embodiment according to the invention, the stirring speed during step (iii) is between 100 and 4000 revolutions/min, advantageously between 400 and 2000 revolutions/min.

[00125] In accordance with an embodiment according to the invention, the stirring speed and the temperature during step (iii) are adjusted so as to obtain a homogeneous, opalescent phase.

[00126] In accordance with an embodiment, the liquid added during step (iv) is or includes water.

[00127] In accordance with an embodiment, the liquid added during step (iv) is at ambient temperature.

[00128] In accordance with an embodiment, the stirring speed during step (iv) is between 1000 and 5000 revolutions/min, advantageously between 2000 and 4000 revolutions/min.

[00129] In accordance with an embodiment according to the invention, cooling to ambient temperature during step (iv) takes a time of between 1 and 20 minutes.

[00130] In accordance with an embodiment according to the invention, the hydrophilic gelling agent added during step (v) is chosen from those mentioned in the present invention.

[00131 ] The method for obtaining the compositions according to the invention and described above may also include one or more steps introduced at any point in the method, corresponding for example to the addition of the oily phase and of the salicylic acid compound.

[00132] The invention also relates to a cosmetic treatment method in which a composition as defined according to the invention is applied to keratin materials, and in particular to the skin.

[00133] A subject of the invention is also the use of a composition as defined above, and in particular of a composition comprising a coagel phase, for the formulation of salicylic acid compounds, especially in order to improve the skin absorption thereof.

[00134] The examples that follow will allow the invention to be understood more clearly, without, however, being limiting in nature. The starting materials are referred to by their INCI names. The amounts indicated are given as weight percentages of starting material, unless otherwise mentioned.

Examples

Comparative Example 1

[00135] Compositions 1 and 2 are prepared.

[00136] [Table 1 ]

[00137] Method for preparing composition 1 :

[00138] 1 - Preparation of phase B: Stir phase B at 55°C until the solid dissolves;

[00139] 2- Preparation of phase C: Stir phase C at ambient temperature until the solid dissolves;

[00140] 3- Introduce the mixture of phase A into a melter, maintain the temperature at 65°C for 45 minutes with stirring at 600 rev/m in until a homogeneous, opalescent phase is obtained;

[00141 ] 4- Add phase B to phase A with stirring at between 2000 and 4000 rev/m in, then homogenize for 5 minutes;

[00142] 5- Add phase C to phase A with stirring at between 2000 and 4000 rev/m in, then homogenize for 5 minutes;

[00143] 6- Modify the heat flow to cool, with vigorous stirring at between 2000 and 4000 rev/m in;

[00144] 7- At 40°C, add phase D with stirring and mix until a homogeneous, smooth, glossy phase is obtained.

[00145] Method for preparing composition 2:

[00146] 1 - Preparation of phase B: Stir phase B at 55°C until the solid dissolves; [00147] 2- Preparation of phase C: Mix phase C at ambient temperature;

[00148] 3- Introduce the mixture of phase A into a melter, maintain the temperature at 50°C for 20 minutes with stirring at 600 rev/m in until a homogeneous, translucent phase is obtained;

[00149] 4- Add phase B to phase A with stirring at between 2000 and 4000 rev/m in, then homogenize for 5 minutes;

[00150] 5- Add phase C to phase A with stirring at between 2000 and 4000 rev/min, then homogenize for 5 minutes;

[00151 ] 6- Modify the heat flow to cool, with stirring at between 2000 and 4000 rev/min;

[00152] 7- At 40°C, add phase D with stirring and mix until a homogeneous, smooth, glossy phase is obtained.

[00153] 8- At 30°C, add phase E with stirring and mix until a homogeneous phase is obtained.

[00154] Evaluation of the physicochemical stability of compositions 1 and 2

[00155] Samples of the two compositions, 1 and 2, were placed in storage for a minimum of 6 months at ambient temperature. They were then checked with regard to the following criteria: macroscopic appearance, microscopic appearance (optical microscope, 10x magnification, normal and polarized light), pH, viscosity.

[00156] The results obtained are shown in the table below.

[00157] [Table 2]

[00158] Conclusion: the two formulations are stable for at least 6 months when stored at ambient temperature.

[00159] Evaluation of the skin absorption of compositions 1 and 2

[00160] This evaluation is performed by characterizing the skin absorption of 5-n- octanoylsalicylic acid.

[00161 ] This skin absorption was evaluated in accordance with OECD Guidelines (OECD guideline for the testing of chemicals: guideline 428, skin absorption: in vitro method (13 April 2004)). The studies are performed on frozen skin obtained from plastic surgery following application of a finite dose of formulation (e.g. 5 mg/cm²) for 16 hours. The quantitative analysis is carried by means of a validated LC/MS/MS method, while skin absorption is measured in accordance with the definition provided by the SCCS.

[00162] A non-parametric statistical analysis based on R-estimators is used.

[00163] The table below presents the results obtained.

[00164] [Table 3]

[00165] These results clearly show the beneficial effect of the galenic formulation in a coagel composition according to the invention on the skin absorption of 5-n- octanoylsalicylic acid. Thus, when 5-n-octanoylsalicylic acid is formulated in a conventional oil-in-water composition, the skin absorption thereof is lower.

[00166] Taking these results into account along with those presented above in regard to stability shows that only a composition according to the invention is able to offer both good stability and an effectiveness that is probably superior to 5-n-octanoylsalicylic acid, given the increase in skin absorption that was found.

Illustrative Example 2

[00167] The following care composition is prepared. [00168] [Table 4]

[00169] Method for preparing composition 1 :

[00170] 1 - Preparation of phase C: Stir phase C at 55°C until the solid dissolves;

[00171 ] 2- Preparation of phase B: Stir phase B1 at ambient temperature until the solid dissolves, and then add B2 to B1 ;

[00172] 3- Introduce the mixture of phase A into a melter, maintain the temperature at 65°C for 45 minutes with stirring at 600 rev/m in until a homogeneous, opalescent phase is obtained; [00173] 4- Add phase C to phase A with stirring at between 2000 and 4000 rev/min, then homogenize for 5 minutes;

[00174] 5- Add phase B to phase A with stirring at between 2000 and 4000 rev/min, then homogenize for 5 minutes;

[00175] 6- Modify the heat flow to cool, with vigorous stirring at between 2000 and 4000 rev/min;

[00176] 7- At 40°C, add phase D with stirring and mix until a homogeneous, smooth, glossy phase is obtained.

[00177] 8- If necessary, add a sufficient quantity of phase E to adjust the pH.

[00178] Composition A thus obtained shows good stability over time. When applied to facial skin, it also shows good cosmetic and sensory properties.

Claims

[Claim 1 ] A composition, specifically a cosmetic composition, comprising at least one monoglyceride, at least one tartaric ester of monoglyceride, and at least one salicylic acid compound.

[Claim 2] The composition as claimed in claim 1 , comprising at least one aqueous phase.

[Claim 3] The composition as claimed in any one of claims 1 and 2, in which the monoglyceride(s) comprise a saturated or unsaturated alkyl chain containing from 12 to 22 carbon atoms.

[Claim 4] The composition as claimed in any one of claims 1 to 3, in which the monoglyceride(s) comprise a saturated or unsaturated alkyl chain containing 16 or 18 carbon atoms.

[Claim 5] The composition as claimed in any one of claims 1 to 4, in which the content of monoglycerides ranges from 1 to 20%, preferentially from 2 to 10% and very preferentially from 3 to 8% by weight, relative to the total weight of the composition.

[Claim 6] The composition as claimed in any one of claims 1 to 5, in which the tartaric ester of monoglyceride is a diacetyl tartaric ester of monoglyceride comprising a saturated or unsaturated alkyl chain containing from 12 to 22 carbon atoms and preferably containing 16 or 18 carbon atoms.

[Claim 7] The composition as claimed in any one of claims 1 to 6, in which the content of tartaric ester of monoglyceride ranges from 0.05% to 2%, preferentially from 0.1 to 1 % and very preferentially from 0.1 to 0.5% by weight, relative to the total weight of the composition.

[Claim 8] The composition as claimed in any one of claims 1 to 7, in which the salicylic acid compound(s) are chosen from salicylic acid and the salicylic acid derivatives having the following formula:

[Chem.3] in which:

- the radical R denotes a linear, branched or cyclic saturated aliphatic chain

containing from 2 to 22 carbon atoms; an unsaturated chain containing from 2 to 22 carbon atoms, containing one or more double bonds that may be conjugated; an aromatic nucleus linked to the carbonyl radical directly or via saturated or unsaturated aliphatic chains containing from 2 to 7 carbon atoms; said groups possibly being substituted with one or more substituents, which may be identical or different, chosen from (a) halogen atoms, (b) the trifluoromethyl group, (c) hydroxyl groups in free form or esterified with an acid containing from 1 to 6 carbon atoms, or (d) a carboxyl function in free form or esterified with a lower alcohol containing from 1 to 6 carbon atoms;

- R’ is a hydroxyl group;

- and also salts thereof derived from a mineral or organic base.

[Claim 9] The composition as claimed in claim 8, in which the radical R in formula [Chem.3] is a C3-C11 alkyl group.

[Claim 10] The composition as claimed in any one of claims 1 to 9, in which the salicylic acid compound is chosen from salicylic acid and 5-n- octanoylsalicylic acid, and it is preferably 5-n-octanoylsalicylic acid.

[Claim 11 ] The composition as claimed in any one of claims 1 to 10,

comprising at least one hydrophilic gelling agent.

[Claim 12] The composition as claimed in claim 11 , in which the hydrophilic gelling agent(s) are chosen from xanthan gum, copolymers of acrylamide and sodium acryloyldimethyl taurate, and any mixture thereof.

[Claim 13] The composition as claimed in any one of claims 1 to 12,

comprising at least one oil.

[Claim 14] The composition as claimed in claim 13, in which the oil(s) are chosen from Guerbet alcohols and lipophilic amino acid derivatives.

[Claim 15] The composition as claimed in claim 14, in which the Guerbet alcohol(s) are obtained by converting an aliphatic primary alcohol into a beta- alkylenated alcohol dimer via the following chemical reaction:

[Chem.4]

w

in which R is a C8-C30 alkyl radical, preferably a C12-C24 alkyl radical and even more preferentially a C16-C20 alkyl radical.

[Claim 16] The composition as claimed in any one of claims 14 and 15, in which the Guerbet alcohol is octyldodecanol.

[Claim 17] The composition as claimed in any one of claims 14 to 16, in which the lipophilic amino acid derivative(s) are chosen from the amino acid esters having the following formula:

[Chem.5]

R’ 1 (CO)N(R'2) fct(R’3)(CH2)n(CO)OR’4 in which:

n is an integer equal to 0, 1 or 2,

R’1 represents a linear or branched C5 to C21 alkyl or alkenyl radical,

R’2 represents a hydrogen atom or a C1 to C3 alkyl radical,

R’3 represents a radical chosen from the group formed by a hydrogen atom, a methyl group, an ethyl group and a linear or branched C3 or C4 alkyl radical, R’4 represents a linear or branched C1 to C10 alkyl radical, a linear or branched C2 to C10 alkenyl radical or a sterol residue.

[Claim 18] The composition as claimed in claim 17, in which in formula [Chem.5] the group R’1 (CO)- is an acyl group of an acid chosen from the group formed by capric acid, lauric acid, myristic acid, palmitic acid, stearic acid, behenic acid, linoleic acid, linolenic acid, oleic acid, isostearic acid, 2- ethylhexanoic acid, coconut oil fatty acids, palm kernel oil fatty acids and hydrogenated palm kernel oil fatty acids, which may or may not include a hydroxyl group, and it is preferably lauric acid.

#

[Claim 19] The composition as claimed in any one of claims 17 and 18, in which in formula [Chem.5] the -N(R'2)CH(R'3)(CH2)n(CO)- part of the amino acid ester is chosen from the following amino acids: glycine, alanine, valine, leucine, isoleucine, serine, threonine, proline, hydroxyproline, b-alanine, aminobutyric acid, aminocaproic acid, sarcosine, or N-methyl-B-alanine, and it is preferably sarcosine.

[Claim 20] The composition as claimed in any one of claims 17 to 19, in

which in formula [Chem.5] the part of the amino acid esters corresponding to the group OR’4 may be obtained from alcohols chosen from the group formed by methanol, ethanol, propanol, isopropanol, butanol, tert-butanol, isobutanol, 3-methyl-1 -butanol, 2-methyl-1 -butanol, fusel oil, pentanol, hexanol,

cyclohexanol, octanol, 2-ethylhexanol, decanol, lauryl alcohol, myristyl alcohol, cetyl alcohol, cetostearyl alcohol, stearyl alcohol, oleyl alcohol, behenyl alcohol, jojoba alcohol, 2-hexadecyl alcohol, 2-octyldodecanol alcohol and isostearyl alcohol.

[Claim 21 ] The composition as claimed in any one of claims 14 to 20, in

which the lipophilic amino acid derivative is isopropyl N-lauroylsarcosinate having the following formula:

[Chem.6]

CH3-(CH2)1 OCG-N{CH3)~€H2~COO~ CH2-( CH3)2.

[Claim 22] The composition as claimed in any one of claims 1 to 21 ,

comprising at least one oil chosen from octyldodecanol and isopropyl N- lauroylsarcosinate.

[Claim 23] The composition as claimed in any one of claims 1 to 22,

comprising a coagel phase.

[Claim 24] A cosmetic treatment method in which a composition as defined in any one of claims 1 to 23 is applied to keratin materials, and in particular to the skin.

[Claim 25] The use of a composition as defined in any one of claims 1 to 23 to improve the skin absorption of salicylic acid compounds.