EP1653919A1

EP1653919A1 - Cosmetic composition comprising a particular ester, and uses thereof

Info

Publication number: EP1653919A1
Application number: EP03755636A
Authority: EP
Inventors: Pascal Arnaud
Original assignee: LOreal SA
Current assignee: LOreal SA
Priority date: 2003-07-25
Filing date: 2003-07-25
Publication date: 2006-05-10
Also published as: US20070190003A1; WO2005018584A1; AU2003273476A1; JP2007516935A

Abstract

The invention relates to a composition in the form of a physiologically-acceptable medium containing a fatty phase comprising at least one ester resulting from the reaction of a polyol with a carboxylic acid, having formula (I), wherein: R1, R2 and R3 are radicals which are selected independently from optionally-functionalised alkyl, aryl, aralkyl radicals, and the combinations thereof. The invention also relates to the use of an ester having the aforementioned formula (I) in a cosmetic composition with performance properties, for example, in terms of colour and/or brightness and/or comfort and/or non-migration.

Description

Cosmetic composition comprising a particular ester and its uses

The present invention relates to a composition, in particular for making up or caring for the skin, including the scalp, both of the face and of the human body, of the lips or of the integuments of human beings, such as hair, eyelashes, the eyebrows or the nails, comprising a physiologically acceptable medium which contains a fatty phase comprising a particular ester. This composition has remarkable cosmetic properties, in particular of hold, and gives makeup or care properties of shine and / or comfort and / or non-migration. The composition of the invention may in particular be in the form of a makeup product for keratin materials (skin, lips, integuments) having in particular non-therapeutic care and / or treatment properties. It constitutes in particular a lipstick or a lip gloss, a foundation, a loose or compacted powder, a blush or an eyeshadow, a makeup base, a concealer, a tattoo product, a mascara, an eye -liner, nail polish, artificial skin tanning product, hair coloring or care product.

The use of silicone compounds in cosmetic compositions, in particular make-up compositions, is known to formulators. Mention may be made, for example, of patent EP-A-0407205 which describes a composition comprising the combination of a silicone gum and a silicone oil which makes it possible to obtain good properties of resistance, spreading and comfort of the composition.

These compounds give cosmetic compositions excellent sensory properties, in particular a non-greasy feel, spreading and slippery properties and make it possible, in particular, to obtain a particularly homogeneous film on the skin.

It is also known to use these silicone compounds with a view to increasing the hold of cosmetic compositions, in particular make-up, and / or reducing their migration. By "migration" is meant an overflow of the composition (and in particular of the color) outside the initial trace of the makeup, resulting in an unsightly effect. Migration is often cited by women as a major shortcoming of conventional lipsticks and eyeshadows.

Problems with poor hold are characterized by a change in color (toning, paling) generally as a result of an interaction with the sebum and / or sweat secreted by the skin in the case of foundation and eyeshadow or an interaction with saliva in the case of lipsticks. This forces the user to remake themselves very often, which can be a waste of time.

However, the silicone compounds can present compatibility problems (solubility) with other hydrocarbon compounds conventionally used in cosmetic compositions, which limits their use.

On the other hand, cosmeticians are currently looking for raw materials having optimal tolerance with respect to keratin materials, while exhibiting properties that respect the environment, which is not always the case with silicone compounds.

The applicant has found, surprisingly, that the particular esters according to the invention have properties equivalent to those of silicone compounds while having greater compatibility (solubility). This allows for greater diversity in formulations. In addition, the esters according to the invention have greater harmlessness with respect to keratin materials and can therefore be formulated in addition to or in substitution for the silicone compounds.

The use of such esters makes it possible to obtain compositions having good cosmetic and sensory properties, in particular of staying power, in particular of color, of non-migration and of comfort, non-irritating for keratin materials and having a more or less appearance. gloss adapted to the desire of consumers. Document EP 1 040 814 teaches nail varnish compositions containing an acrylic polymer, the ester of tert-butyl acid and of trimethyl-2,2,4-pentane-diol-1, 3, and a second solvent. organic. These varnish compositions have good properties of adhesion to the nail, of shine and are easily removed.

It has been described in US Patents 4,243,657 and US 4,224,311, cosmetic compositions containing mono or diesters of neo acid and diols. These compositions make it possible to improve the mechanical resistance of the hair to brushing and drying. They also have better oxidation stability.

Finally, the document WO 03/026698 describes diesters of diols. These diesters are esters of neopentanoic acid with unbranched alkylene oxides of formula HO (C _n H _2n O) _m H such that n is equal to 2 or 3 and m is between 2 and 4.

The first subject of the present invention is a composition comprising a physiologically acceptable medium containing a fatty phase comprising at least one ester resulting from the reaction of a polyol with a carboxylic acid of formula (I) below:

R

R., C COOH (I)

in which R ^ R ₂ and R ₃ are radicals chosen independently from alkyl, aryl, aralkyl radicals, optionally functionalized, and their associations, characterized in that said polyol is chosen from polyols comprising a carbon atom, located in alpha carbon carrying an alcohol function, which is trisubstituted by radicals chosen independently of one another from the alkyl, aryl, aralkyl radicals and their associations, at least one of the alkyl, aryl, aralkyl radicals containing at least one alcohol function, said polyol not being trimethyl-2,2,4-pentanediol-1, 3. A second subject of the present invention is a composition comprising a physiologically acceptable medium containing a fatty phase comprising at least one ester resulting from the reaction of a polyol with a carboxylic acid of formula (I) below:

R, in which R _{1 t} R ₂ and R ₃ are radicals independently chosen from alkyl, aryl, aralkyl radicals, optionally functionalized, and their associations, said acid comprising from 5 to 9 carbon atoms and said polyol not being a compound of formula HO (C _n H _2n O) _m H such that n is equal to 2 or 3 and m is between 2 and 4. According to these first two objects, the word “ester” according to the invention means, depending on the case, a monoester, a diester, a triester or more generally a polyester.

A third object of the present invention is a composition comprising a physiologically acceptable medium containing a fatty phase comprising at least one ester resulting from the reaction of a polyol with a carboxylic acid of formula (I) below:

R

R C COOH (I)

R ₃ in which R _{1 (} R ₂ and R ₃ are radicals chosen independently from alkyl, aryl, aralkyl radicals, optionally functionalized, and their associations, said ester comprising at least three ester functions.

According to the three objects of the invention, by "at least" one ester means one or more esters.

By "physiologically acceptable" is meant non-toxic and capable of being applied to the skin, the integuments or the lips of human beings.

The physiologically acceptable medium of the composition according to the invention is in particular cosmetically acceptable, that is to say pleasant in taste, in feel, in appearance and / or in odor, applicable for several days for several months.

By "functionalized" is meant a radical comprising a heteroatom, that is to say an atom different from the carbon atom (such as an oxygen, nitrogen, sulfur, fluorine atom) or a functional group such as a carboxyl group -COOH, hydroxyl -OH, amide - NHR or ester -COOR, R representing an alkyl radical.

The subject of the present invention is also the use of at least one of the esters described above, in a cosmetic composition, as an agent for imparting to the said composition hold properties, in particular color, and / or shine and / or comfort and / or non-migration.

Another object of the present invention is the use of at least one of the esters described above, in a cosmetic composition having hold properties, in particular color, and / or shine and / or comfort and / or non-migration. The present invention also relates to a cosmetic process for imparting to a film of cosmetic composition hold properties, in particular color, and / or gloss and / or comfort and / or non-migration, consisting in introducing into said composition at least one of the esters described above. The ester of the composition according to the invention can result from a total or partial esterification.

A total ester is an ester not comprising a free OH group, because all the alcohol functions of said polyol reacted with an acid molecule of formula (I), and because the acid of formula (I) does not include in its structure a hydroxyl group.

A partial ester comprises at least one OH group, which may be an alcohol function of the polyol which has not reacted with an acid function of the acid of formula (I). A partial ester may also result from the total reaction of a polyol with an acid of formula (I) such that at least one of the radicals R 1, R ₂ and R ₃ contains a hydroxyl group.

The ester of the composition according to the invention results from the reaction of a carboxylic acid of formula (I) with a polyol.

Carboxylic acid

According to the three objects of the invention, the carbon located in alpha of the acid function of the carboxylic acid of formula (I) is trisubstituted by a hydrocarbon group. This carbon atom is therefore directly linked to 4 carbon atoms and is called "neo" carbon. An acid comprising such a structure is called “neo” acid and will be designated in the following text. The radicals Ri, R ₂ and R ₃ are advantageously chosen independently from saturated alkyl radicals. The “neo” carboxylic acid can be a monoacid or a polyacid, ie at least one of the radicals R _{1 (} R ₂ or R ₃ contains a functional group -COOH. Preferably, the carboxylic acid is a monoacid.

The polyol can be a diol, a triol or a tetraol.

According to the second object of the invention, the carbon located in alpha of the acid function of the carboxylic acid of formula (I) is trisubstituted by radicals chosen independently from saturated or unsaturated, branched or unbranched aliphatic hydrocarbon radicals, comprising in particular from 1 to 5 carbon atoms, provided that the number of carbon atoms of the carboxylic acid of formula (I) is between 5 and 9.

The number of carbon atoms in the carboxylic acid of formula (I) preferably ranges from 5 to 7. The radicals R _{1 (} R ₂ and R ₃ are advantageously chosen independently from saturated alkyl radicals having from 1 to 5 carbon atoms. The radicals Ri, R ₂ and R ₃ are especially chosen independently from methyl, ethyl, propyl, isobutyl, isopropyl, butyl and pentyl, provided that the number of carbon atoms of the carboxylic acid of formula (I) is included ranging from 5 and 9.

According to the second subject of the invention, use is preferably made of a “neo” carboxylic acid chosen from neopentanoic acid of formula CH ₃ -C (CH ₃ ) ₂ -COOH, neohexanoic acid and neoheptanoic acid of formula C ₃ H ₇ -C (CH ₃ ) ₂ -COOH. Neopentanoic acid is preferred such that the radicals R 1, R ₂ and R ₃ are methyl radicals.

According to the first and third objects of the invention, the carbon located in alpha of the acid function of the carboxylic acid of formula (I) is trisubstituted by radicals chosen independently from the alkyl, aryl, aralkyl radicals, and their associations , these radicals can be identical or different.

By alkyl radical is meant a saturated or unsaturated, branched or unbranched aliphatic hydrocarbon chain, comprising in particular from 1 to 28 carbon atoms.

The word "branched" means at least one pendant hydrocarbon chain comprising at least 1 carbon atom.

By aryl radical is meant a radical derived from an aromatic cyclic compound by elimination of a hydrogen atom such as for example the phenyl or tolyl radicals. By aralkyl radical is meant an alkyl chain substituted by an aryl radical, for example of the R'-C ₆ H _{5 type} , R 'being a C ₁ -C ₅ alkyl, such as for example the benzyl or phenethyl radicals.

These alkyl, aryl or aralkyl radicals can be functionalized, which means that they can comprise in their structure a heteroatom, that is to say an atom different from the carbon atom (such as an oxygen atom, nitrogen, sulfur, fluorine) or a functional group such as a carboxyl group -COOH, hydroxyl -OH, amide - NHR or ester -COOR, R representing an alkyl.

Preferably, the radicals R ^ R ₂ and R ₃ are independently chosen from non-functionalized alkyl, aryl or aralkyl radicals.

According to the first and third objects of the invention, the radicals R ^ R ₂ and R ₃ are advantageously chosen independently from the saturated alkyl radicals _, preferably from the saturated alkyl radicals in CC ₁₅ , and better still, in C 1 -C ₆ such as for example the methyl, ethyl, propyl, isopropyl, butyl, isobutyl, pentyl, isopentyl, hexyl radical.

According to the first and third objects of the invention, the “neo” carboxylic acid advantageously comprises a total number of carbon atoms ranging from 5 to 30, and better still from 5 to 15, and better still from 5 to 10.

According to the first and third objects of the invention, use is preferably made of a “neo” carboxylic acid chosen from neopentanoic acid of formula CH ₃ -C (CH ₃ ) ₂ -COOH, neohexanoic acid, neoheptanoic acid of formula C ₃ H ₇ -C (CH ₃ ) ₂ -COOH, neodecanoic acid of formula C ₆ H ₁₃ -C (CH ₃ ) ₂ -COOH, and mixtures thereof. More preferably, the “neo” carboxylic acid is neopentanoic acid.

Polyol According to the first subject of the invention, the polyol is chosen from “neo” polyols, that is to say polyols which contain a carbon atom, located in alpha of the carbon carrying an alcohol function, which is trisubstituted by radicals independently selected from the alkyl, aryl, aralkyl radicals and their associations, at least one of the alkyl, aryl, aralkyl radicals containing at least one alcohol function. This carbon atom directly linked to 4 other carbon atoms is therefore a “neo” carbon as defined above.

Advantageously, the “neo” polyol contains a carbon atom located in alpha of the carbon carrying one of the alcohol functions which is trisubstituted by radicals chosen independently from saturated alkyl radicals, preferably alkyl radicals saturated with and better with CC ₆ , at at least one of the alkyl radicals containing at least one alcohol function.

As “neo” polyol, in particular, trimethylol propane of formula HOCH ₂ - C (C ₂ H ₅ ) (CH ₂ OH) ₂ , pentaerythritol of formula HOCH ₂ -C (CH ₂ OH) ₂ -CH ₂ OH are chosen. , neopentyl glycol and mixtures thereof.

The “neo” polyol advantageously comprises a number of carbon atoms ranging from 5 to 20, and preferably from 5 to 10. The polyol can be a diol, a triol or a tetraol.

As the neo diol, the neopentyl glycol of formula HOCH ₂ -C (CH ₃ ) ₂ -CH ₂ OH is chosen in particular.

According to the third object, the ester comprises at least three ester functions and it is obtained by reaction of a polyol with a carboxylic acid of formula (I). The polyol can comprise two or more hydroxyl groups, and the acid of formula (I) can comprise radicals R 1 and / or R ₂ and / or R ₃ functionalized by ester groups or alternatively the radicals. R ^ R ₂ and / or R ₃ are functionalized by an ester group In the case where only one of the hydroxyl groups of the polyol reacts with the acid of formula (I), the radicals Ri, R ₂ and / or R ₃ are functionalized by two ester groups.

If the polyol comprises two hydroxyl groups or if only two of the hydroxyl groups of the polyol each react with an acid of formula (I) then at least one of the acids of formula (I) which has reacted with the polyol comprises an ester group.

Finally, if the polyol comprises at least three hydroxyl groups, the acid of formula (I) having reacted with each of the hydroxyl groups of the polyol does not necessarily comprise at least one radical R, R ₂ and / or R ₃ functionalized by a group ester.

According to the second or third subject of the invention, the polyol can therefore comprise a number of carbon atoms ranging from 2 to 20, and preferably from 3 to 10. The polyol can be a diol, a triol or a tetraol . The polyol is preferably an aliphatic polyol whose backbone is saturated.

According to the second subject of the invention, the polyol can be chosen from ethylene glycol, propylene glycol, butylene glycol, polypropylene glycol, polyethylene glycol other than a compound of formula HO (C _n H _2n O) _m H such that n is equal to 2 or 3 and m is between 2 and 4, glycerol, diglycerol, triglycerol, isopentyl diol, sorbitol and their mixtures.

According to the third subject of the invention, the polyol can be chosen from ethylene glycol, propylene glycol, butylene glycol, polypropylene glycol, polyethylene glycol, glycerol, diglycerol, triglycerol, isopentyl diol, sorbitol and their mixtures.

According to the second or third subject of the invention, the polyol can be chosen from “neo” polyols as described above, for example trimethylol propane, pentaerythritol, neopentyl glycol, or their mixtures.

Ester

Preferably, the ester of the composition according to the invention is in liquid form at room temperature (25 ° C) and atmospheric pressure (760mm of Hg or 1.01.10 ⁵ Pa).

This ester is in particular an oil. By "oil" is meant any liquid non-aqueous medium which is insoluble in water at room temperature and atmospheric pressure.

According to the first subject of the invention, the ester used in the composition of the invention can be advantageously chosen from neopentylglycol (C ₁₅ ) di-neopentanoate, neopentyl glycol (C ₁₉ ) dneoheptanoate and mixtures thereof. (The C _n in parentheses represents the total number of carbon atoms of the cited compound).

According to the second subject of the invention, the ester used in the composition of the invention can be advantageously chosen from glyceryl trineopentanoate (Cι ₈ ), glyceryl trineoheptanoate (C ₂₄ ), and mixtures thereof . (The C _n in parentheses represents the total number of carbon atoms of the cited compound).

According to the third subject of the invention, the ester is a polyester and comprises at least three ester functions -COO-. It can be a triester, a tetraester or a pentaester. The polyester comprising at least three ester functions results from the reaction of a carboxylic acid of formula (I) with a polyol. The ester of the composition can result from a total or partial esterification (in the latter case, the ester comprises one or more free -OH functions). The ester advantageously contains no free hydroxyl group, in the sense that all of the hydroxyl groups of the polyol have reacted with a carboxylic acid molecule not containing a hydroxyl group.

According to the third subject of the invention, the carboxylic acid of formula (I) can be a monoacid or a polycarboxylic acid and the polyol can be a diol, a triol or a tetraol, said acid and said polyol being chosen so that their reaction leads to a total or partial ester comprising at least three ester functions.

The polyester preferably results from the reaction of a mono carboxylic acid of formula (I) with a triol (polyol comprising at least three hydroxyl groups). The polyester is preferably a total ester in the sense that it does not have a free -OH function. The polyester is for example glyceryl tri-neodecanoate (C ₃₃ ).

The ester of the composition according to the present invention can represent from 0.1 to 99.9%, preferably from 1 to 99% and better still from 5 to 90% of the total weight of the composition. It represents for example from 5 to 60% of the total weight of the composition.

Advantageously, the ester is in sufficient quantity to give the composition properties of shine and / or resistance over time and / or non-migration and / or comfort.

This ester can be prepared according to methods known to those skilled in the art. We can for example cite the following documents in which the synthesis of this compound is described: PAWLENKO Justus, Liebigs Ann. Chem. 663 (1963); M. FEFER and A. RUTKOWSKI, JAOCS 45, 5-10 (1968); B. PAULSEN, Chem. Ber. 104, 1281-1294 (1971); V.A. BOCHKOVA, J. Appl. Chem. USSR 46_, 1929-1932 (1973) and the patents US-A-3,441,600 and US-A-3,523,084 from the company SINCLAIR RESEARCH INC.

The amounts of the various ingredients of the composition according to the invention are given in percentages by weight relative to the total weight of said composition.

The composition according to the invention can also comprise at least one coloring agent which can be chosen from water-soluble or liposoluble dyes, pigments, nacres or pearlescent pigments and their mixtures.

By “pigments”, it is necessary to understand white or colored particles insoluble in the liquid fatty phase of the composition, intended to color and / or opacify the composition. By "nacres" or "nacreous pigments" is meant iridescent particles, in particular produced by certain molluscs in their shell or else synthesized, insoluble in the liquid fatty phase of the composition.

The term “dyes” should be understood to mean generally organic compounds which are soluble in fatty substances such as oils or in an aqueous-alcoholic phase.

The liposoluble dyes are for example Sudan red, D&C Red n ° 17, D&C Green n ° 6, β-carotene, soybean oil, Sudan brown, D&C Yellow n ° 11, D&C Violet n ° 2, D&C orange n ° 5, quinoline yellow, annatto, bromoacids. The water-soluble dyes are, for example, beet juice, methylene blue, caramel. The liposoluble and water-soluble dyes can represent from 0.001 to 20% of the total weight of the composition and better still from 0.1 to 6%.

The pigments can be white or colored, mineral and / or organic, coated or not.

Mention may be made, among the mineral pigments, of titanium dioxide, optionally surface-treated, zirconium or cerium oxides, as well as zinc and iron oxides (black, yellow, brown or red) or chromium, manganese violet, ultramarine blue, chromium hydrate and ferric blue. Among the organic pigments that may be mentioned are carbon black, pigments of the organic lacquer type of barium, strontium, calcium or aluminum, including those subject to certification by the Food and Drug Administration (FDA) (example D&C or FD&C) and those free of FDA certification like cochineal carmine lacquers. The pigments can be present in the composition in an amount of 0.05 to 40% of the weight of the final composition, and preferably in an amount of 2 to 20% for a non-pulverulent composition. For a pulverulent composition, they can represent up to 70% of the total weight of the composition.

The nacres or nacreous pigments can be chosen from white nacreous pigments such as mica coated with titanium or bismuth oxychloride, colored nacreous pigments such as mica titanium with iron oxides, mica titanium with in particular blue ferric or chromium oxide, titanium mica with an organic pigment of the aforementioned type as well as pearlescent pigments based on bismuth oxychloride. It is thus possible to use pigments with goniochromatic properties, in particular with liquid crystals or multilayers. The nacres can be present in the composition in an amount of 0.001 to 20% of the total weight of the composition, preferably at a rate of the order of 1 to 15%. In general, the coloring agents represent from 0.001 to 60%, and better still from 0.01 to 50%, and better still, from 1 to 40% of the total weight of the composition.

Preferably, the coloring agent is chosen from pigments, nacres and their mixtures.

According to one embodiment of the invention, the composition according to the invention also comprises at least one filler.

By "filler" is meant any colorless or white particle chosen from mineral or organic fillers, lamellar, spherical or oblong, chemically inert in the composition. Mention may be made of talc, mica, silica, kaolin, polyamide powders such as Nylon® (Orgasol® from Atochem), poly-β-alanine and polyethylene, powders of tetrafluoroethylene polymers (Teflon® ), lauroyl-lysine, starch, boron nitride, polymeric hollow microspheres such as those of polyvinylidene chloride / acrylonitrile such as Expancel® (Nobel Industry), particles of acrylic polymer, in particular of copolymer d acrylic acid such as Polytrap® (Dow Corning) and silicone resin microbeads (Tospearls® from Toshiba, for example), precipitated calcium carbonate, dicalcium phosphate, carbonate and magnesium hydro-carbonate, l hydroxyapatite, hollow silica microspheres (Silica Beads® from Maprecos), glass or ceramic microcapsules, metallic soaps derived from organic carboxylic acids having 8 to 22 carbon atoms, preferably 12 to 18 atoms carbon, for example zinc, magnesium or lithium stearate, zinc laurate, magnesium myristate, and mixtures thereof. These fillers can be treated or not on the surface, in particular to make them lipophilic. Preferably, the fillers have a particle size less than 50 μm and can represent from 0.01 to 35%, preferably from 0.05 to 25% and better still from 0.5 to 15% of the total weight of the composition, if they are presented.

The composition according to the invention may advantageously comprise at least one additional non-aqueous compound different from the ester used in the composition according to the invention, chosen from oils, fatty substances which are pasty at room temperature, waxes, gums, resins, lipophilic polymers and mixtures thereof. This additional non-aqueous compound can represent from 0.001 to 90% of the total weight of the composition, preferably from 0.05 to 60% and better still from 1 to 50%.

In particular, it also contains at least one wax. By “wax” in the sense of the present invention, is meant a lipophilic fatty compound, solid at room temperature (25 ° C.), with reversible solid / liquid state change, having a melting temperature above 30 ° C. which can range up to 200 ° C, a hardness greater than 0.5 MPa, and having an anisotropic crystalline organization in the solid state. The size of the crystals is such that the crystals diffract and / or scatter light, giving the composition a cloudy, more or less opaque appearance. By bringing the wax to its melting point, it is possible to make it miscible with oils and to form a homogeneous mixture microscopically, but by bringing the temperature of the mixture to room temperature, the wax is recrystallized from the oils of the mixed. The wax can be chosen from solid waxes at room temperature, such as hydrocarbon waxes such as beeswax, which may be modified, Carnauba, Candellila, Ouricoury, Japanese wax, cork fiber waxes or sugar cane, paraffin waxes, lignite waxes, microcrystalline waxes, lanolin wax, Montan wax, ozokerites, polyethylene or ethylene copolymer waxes, waxes obtained by Fischer-Tropsch synthesis, hydrogenated oils, fatty esters and concrete glycerides at 25 ° C. Silicone waxes can also be used, among which mention may be made of alkyl, alkoxy and / or polymethylsiloxane esters. The waxes can be in the form of stable dispersions of colloidal particles of wax as they can be prepared according to known methods, such as those of "Microemulsions Theory and Practice", LM Prince Ed., Académie Press (1977), pages 21-32. Preferably, the waxes used have a melting temperature at least equal to 45 ° C.

The wax can represent from 0.01 to 50%, preferably from 2 to 40%, and better still from 5 to 30% of the total weight of the composition. The gums which can be used in the invention are generally present in the form dissolved in an oil and the resins can be liquid or solid at room temperature.

The nature and quantity of gums, pasty bodies are a function of the mechanical properties and textures sought.

The additional oils can be hydrocarbon and / or silicone and / or fluorinated oils. These oils can be of animal, vegetable, mineral or synthetic origin. "Hydrocarbon oil" means an oil comprising mainly carbon and hydrogen atoms and optionally one or more functions chosen from the hydroxyl, ester, ether and carboxylic functions. As an example of an additional oil which can be used in the invention, mention may be made of: hydrocarbon oils of animal origin such as perhydrosqualene; vegetable hydrocarbon oils such as liquid triglycerides of fatty acids having from 4 to 10 carbon atoms such as triglycerides of heptanoic or octanoic acids or jojoba oil; linear or branched hydrocarbons, of mineral or synthetic origin such as paraffin oils and their derivatives, petrolatum; synthetic esters and ethers, in particular of fatty acids such as oils of formula R ₄ COOR ₅ in which R ₄ represents the remainder of an aliphatic carboxylic acid containing from 1 to 39 carbon atoms and R ₅ represents a hydrocarbon chain containing from 1 to 40 carbon atoms with 10 = R ₄ + R ₅ = 41 such as, for example, isononyl isononanoate, isopropyl myristate, ethyl 2- hexyl palmitate, octyl 2- stearate dodecyl, octyl 2-dodecyl erucate, isostearyl isostearate; hydroxylated esters such as isostearyl lactate, octyl hydroxy stearate, hydroxy octyl dodecyl stearate, diisostearyl malate, heptanoates, octanoates, fatty alcohol decanoates; certain polyol esters such as propylene glycol dioctanoate; fatty alcohols having from 12 to 26 carbon atoms such as octyl dodecanol, 2-butyloctanol, 2-hexyl decanol, 2-undecyl pentadecanol, oleic alcohol; - fluorinated oils possibly partially hydrocarbon-based and / or silicone-based; silicone oils such as volatile or non-volatile, linear or cyclic polydimethylsiloxanes (PDMS); polydimethylsiloxanes comprising alkyl, alkoxy or phenyl groups, during or at the end of the silicone chain, groups having from 2 to 24 carbon atoms; phenylated silicones such as phenyl trimethicones (such as phenyl trimethicone sold under the trade name DC556 by Dow Corning), phenyl dimethicones, phenyl trimethylsiloxy diphenyl siloxanes, diphenyl dimethicones, diphenyl methyldiphenyl trisiloxanes, 2-phenylethyl siloxysilicates, - and mixtures thereof. The additional oils can represent from 0.01 to 90% of the total weight of the composition, preferably from 0.05 to 60% and better still from 1 to 35%.

The composition of the invention may also comprise at least one additive usually used in the field concerned, such as water, antioxidants, preservatives, neutralizers, lipophilic gelling agents or non-aqueous liquid compounds, aqueous phase gelling agents, dispersants, cosmetic active agents, and mixtures thereof. These additives, with the exception of water which can represent from 0 to 80% and for example from 1 to 70 and better still from 1 to 60% of the total weight of the composition, can be present in the composition in an amount of 0 .0005 to 20% of the total weight of the composition and better still from 0.001 to 10%.

By "cosmetic active" means a lipophilic or hydrophilic compound providing a benefit to keratin materials and more especially to the skin and lips.

As cosmetic active agent which can be used in the invention, mention may be made of vitamins A, E, C, B ₃ , F, provitamins such as D-panthenol, soothing active agents such as α-bisabolol, Paloe vera, allantoin, plant extracts or essential oils, protective or restructuring agents such as ceramides, freshness active ingredients such as menthol and its derivatives, emollients (cocoa butter, dimethicone), moisturizers (arginine PCA), anti-wrinkle active ingredients, essential fatty acids, sunscreens, and mixtures thereof.

Of course, those skilled in the art will take care to choose any additional additives and / or their amount in such a way that the advantageous properties of the composition according to the invention are not or substantially not affected by the envisaged addition. The applications of the compositions according to the invention are multiple and relate to all cosmetic products, whether colored or not, and more particularly lip makeup products such as lipsticks or lip glosses and makeup products for the complexion, namely facial skin, such as foundations, concealer, loose or compacted powder, blush or eyeshadow, blush, make-up bases.

In a particular embodiment of the invention, the compositions according to the invention can be prepared in the usual manner by a person skilled in the art. They can be in the form of a cast product, and for example in the form of a stick or stick, or in the form of a cup usable by direct contact or with a sponge or in a hot water bottle. In particular, they find application as a poured foundation, blush or eyeshadow, lipstick, base or lip care balm, concealer product. They can also be in the form of a flexible paste or else a gel, a more or less fluid cream. They can then constitute foundations or lipsticks, lip glosses (gloss in English terminology), sunscreen or skin coloring products. The compositions of the invention may be anhydrous and contain less than 5% of water added relative to the total weight of the composition. They can then be presented in particular in the form of an oily gel, an oily liquid, a paste or a stick or also in the form of a vesicular dispersion containing ionic and / or nonionic lipids. They can also be in the form of a single or multiple emulsion with an oily or aqueous continuous phase, an oily dispersion in an aqueous phase using vesicles containing ionic and / or nonionic lipids. These dosage forms are prepared according to the usual methods of the fields considered. The composition according to the invention may be in the form of a composition, colored or not, for caring for the skin, in the form of a sun protection or make-up removal composition or also in the form of a hygienic composition. If it contains assets

^'Cosmetics, it can then be used as a care base or non-therapeutic treatment for the skin such as hands or face or lips (lip balms, protecting the lips from cold and / or sunlight and / or wind ), artificial skin tanning product. The composition of the invention can also be in the form of a colored make-up product for the skin, in particular the face, such as a blush, blush or eyeshadow, body make-up such as a semi tattoo product. permanent or lip makeup such as a lipstick or a lip gloss, possibly having non-therapeutic care or treatment properties, an appendage makeup product such as for example a nail polish, a mascara, an eyeliner, a product hair coloring or care. Preferably, the composition according to the invention is in the form of a lip makeup product such as a lipstick or a lip gloss or a complexion makeup product, namely the skin of the face, such as a foundation. A lip makeup product is advantageously in anhydrous form. A complexion makeup product is preferably in the form of an emulsion, in particular an oil-in-water emulsion. The composition according to the invention can be produced by known methods, generally used in the cosmetic field. The following examples are intended to illustrate, without limitation, the object of the present invention. The quantities are given in percentage by mass.

Example 1: Measures of viscosity and spreading properties of compounds according to the invention and according to the prior art. The inventors have compared the viscosities and spreading properties of the following compounds: The polydimethylsiloxane manufactured or sold by the company Dow Corning under the reference DOW CORNING ^® FLUID 200-5 cSt silicone oil which is commonly used in cosmetic compositions of the prior art. - Di-neopentanoate, neopentyl glycol manufactured or sold by BSI under the reference NEOFEEL 55 ^®, which is an ester as used in the composition according to the invention. 1.1 Viscosity measurements The viscosity is measured at 20 ° C. using a Brookfield "DV-II +" type LV viscometer with a number 1 mobile rotating at 100 rpm.

The results are given in Table I below: Table (I)

1.2. Measurement of spreading properties

A support is prepared consisting of an “ashless” filter paper with a porosity of 25 μm and a diameter of 90 mm, sold by the company Prolabo.

0.1 ml of the test compound is then taken which is deposited in the center of the filter paper, then it is allowed to migrate at 20 ° C.

After 20 min, the diameter of the task obtained is measured using a millimeter rule and then the area of the spot is calculated according to the following formula: area of the task = (π X (diameter of the task) ² ) / 4.

This surface measurement is carried out six times for the same compound. The spread of the compound corresponds to the average of the six surfaces obtained. The results are given in table (II) below. Table (II)

These results show that the polydimethylsiloxane 5 cSt and the neopentyl glycol di-neopentanoate have similar viscosities and spreading properties. It is therefore possible to replace the polydimethylsiloxane by the neopentyl glycol di-neopentanoate in a cosmetic formulation and to obtain similar cosmetic properties while having superior properties, in particular of non-migration. This is demonstrated in the following examples.

Examples 2 and 3: Sticks of lipsticks

The inventors compared the properties of two compositions according to the invention and the prior art as presented in table (III). The composition of Example 2 according to the invention contains neopentyl glycol di-neopentanoate and the composition of Example 3 (comparative) contains polydimethylsiloxane (5 cSt). Table (III)

"Mw = molar mass

Procedure

First, the pigments (phase D) are dispersed and ground in phase A using a three-cylinder mill.

At the same time, a Bentone ^® gel (phase B) is prepared by dispersing, using a high pressure homogenizer, Bentone ^® in the Parléam.

The pigments ground in phase A as well as the Bentone gel are placed in a pan in which the waxes are added (phase C), then heated at 100 ° C. for 2 hours and homogenized using a Rayner shaker. .

Phase E is then added along with the active ingredients (phase F) and the mixture is homogenized for 5 min then poured into an appropriate mold at 42 ° C to form sticks. The mold is then placed at -20 ° C for half an hour and then the sticks are removed from the mold.

Sensory evaluation The compositions of Examples 2 and 3 were applied by half-lips to a panel of 5 qualified people and evaluated according to different criteria.

The ratings on the different criteria are between 0 (not) and 10 (very) inclusive. The results are given in table (IV) below.

Table (IV)

( ^** coverage is the ability of a makeup composition to cover the support on which said composition is applied, in particular to hide imperfections).

The composition of Example 2 has non-migration properties superior to those of the composition of Example 3 (comparative), the other cosmetic criteria being equivalent to those of the composition containing polydimethylsiloxane (Comparative Example 3).

The composition of Example 2 has in particular excellent sliding properties, softness, coverage and agreeability to the application as well as comfort and hold of the composition film over time.

It also has good gloss properties on application and after application.

Neopentyl glycol di-neopentanoate can therefore advantageously replace polydimethysiloxane in cosmetic compositions in order to obtain the properties mentioned above. Example 4: Stick of lipstick

A composition according to the invention is prepared according to the procedure of Examples 2 and 3, containing glyceryl tri-neopentanoate manufactured or marketed by the company BSI under the reference NEOFEEL TNP ^®

Di-isostearyl malate 4.1

Oxypropylene lanolin wax 4.1 Polybutylene 8.2

Octyl -2 dodecanol 4.1

2-octyl dodecyl neopentanoate 0.9

BHT 0.04

Hydrogenated polyisobutene (manufactured or marketed qs 100 under the reference Parléam ^® by the company Nippon Oil and Fats)

Modified hectorite (Bentone ^® 38V from Elementis) 0.8

Polyethylene wax (Mw ^* = 500 g / mol) 10.8

Octacosanyl stearate 3.6

Hydrogenated coco-glycerides 5

Titanium dioxide 2.7

DC Red 7 2.2

DC Red 27 lake 1, 8

Yellow 6 lake 3

Iran oxides (Cl 77499) 2

Glyceryl tri-neopentanoate (manufactured or marketed 17.3 by the company BSI under the reference NEOFEEL TNP ^® )

0.3 tocopheryl acetate 0.3

Ethylhexyl methoxycinnamate 0.7

Perfume 0.2 ^* Mw = molar mass

We obtain a lipstick stick which allows the deposit of a film of lipstick of good behavior, comfortable, non-irritating and which migrates little if not at all.

Example 5: Water-in-oil Foundation

Preparing a foundation composition which contains, as ester according to the invention, the tri-glyceryl neopentanoate manufactured or sold by BSI under the reference NEOFEEL NPT ^®.

Oily phase

Glyceryl tri-neopentanoate (manufactured or marketed by the 29.4 company BSI under the reference NEOFEEL TNP ^® )

Cetyldimethicone copolyol (manufactured or marketed by the company 3

Goldschmidt under the reference Abil ^® EM 90)

Mixture of acetylated glycol stearate and tristearine (manufactured or 0.5 sold by Guardian under the reference Unitwix ^® )

Propylparaben 0.1

Aqueous phase

Water 57.2

Magnesium sulfate 0.7

Glycerol 5

Methylparaben 0.1

pigments

Yellow iron oxide coated with isopropyl triisostearyl titanate (ITT) 0.6

ITT coated red iron oxide 0.39

ITT coated black iron oxide 0.11

ITT coated titanium dioxide 2.9

Procedure The pigments are dispersed in 4% glyceryl tri-neopentanoate using a three-cylinder grinder (3 passages are carried out in the grinder). The rest of the constituents of the oily phase are weighed together and then heated to 70 ° C. The ground and then homogenized pigments are added to the oily phase with stirring with the Moritz stirrer (at a speed of 1000 rpm).

At the same time, the constituents of the aqueous phase are weighed together and then heated to

80 ° C.

The aqueous phase is slowly added to the mixture of oily phase + pigments while maintaining a minimum temperature of 50 ° C. during the addition and passing at a stirring speed of 3000 rpm ^"1 .

Then the mixture is gradually allowed to return to room temperature while maintaining agitation.

The foundation obtained is in the form of a cream. It has good holding properties while being comfortable.

Claims

CLAIMS Composition comprising a physiologically acceptable medium containing a fatty phase comprising at least one ester resulting from the reaction of a polyol with a carboxylic acid of formula (I) below:

R

R, C COOH (l)

R, in which RR ₂ and R ₃ are radicals chosen independently from alkyl, aryl, aralkyl radicals, optionally functionalized, and their associations, characterized in that said polyol is chosen from polyols comprising a carbon atom, located in alpha carbon carrying an alcohol function, which is trisubstituted by radicals chosen independently of one another from the alkyl, aryl, aralkyl radicals and their associations, at least one of the alkyl, aryl, aralkyl radicals containing at least one alcohol function, said polyol not being trimethyl-2,2,4-pentanediol-1, 3.

2. Composition comprising a physiologically acceptable medium containing a fatty phase comprising at least one ester resulting from the reaction of a polyol with a carboxylic acid of formula (I) below:

R R, in which R ^ R ₂ and R ₃ are radicals chosen independently from alkyl, aryl, aralkyl radicals, optionally functionalized, and their associations, said acid comprising from 5 to 9 carbon atoms and said polyol not being a compound of formula HO (C _n H2 _n O) _m H such that n is equal to 2 or 3 and m is between 2 and 4.

3. Composition comprising a physiologically acceptable medium containing a fatty phase comprising at least one ester resulting from the reaction of a polyol with a carboxylic acid of formula (I) below:

R

R ₁ C COOH (D

R in which R ^ R ₂ and R ₃ are radicals independently chosen from alkyl, aryl, aralkyl radicals, optionally functionalized, and their associations, said ester comprising at least three ester functions.

4. Composition according to one of the preceding claims, characterized in that the radicals R ^ R ₂ and R ₃ are chosen independently of one another from saturated alkyl radicals.

5. Composition according to one of the preceding claims, characterized in that the carboxylic acid is a monoacid.

6. Composition according to one of the preceding claims, characterized in that the polyol is a diol, a triol or a tetraol.

7. Composition according to claim 1 or 3, characterized in that the radicals R ^ R ₂ and R ₃ are chosen, independently of one another, from the saturated alkyl radicals Ci-

8. Composition according to claim 7, characterized in that the radicals R ^ R ₂ and R ₃ are chosen independently of one another from saturated C Cβ alkyl radicals.

9. Composition according to claim 1 or 3, characterized in that the carboxylic acid comprises a total number of carbon atoms ranging from 5 to 30, preferably from 5 to 15, preferably from 5 to 10.

10. Composition according to claim 1 or 3, characterized in that the carboxylic acid is chosen from neopentanoic acid, neohexanoic acid, neoheptanoic acid, neodecanoic acid and their mixtures.

1 1. Composition according to claim 2, characterized in that the carboxylic acid comprises from 5 to 7 carbon atoms.

12. Composition according to claim 11, characterized in that the carboxylic acid and is chosen from neopentanoic acid, neohexanoic acid, neoheptanoic acid and their mixtures.

13. Composition according to claim 1, characterized in that the polyol comprises a number of carbon atoms ranging from 5 to 20, preferably from 5 to 10.

14. Composition according to claim 1, characterized in that the polyol contains a carbon atom located in alpha of the carbon carrying one of the alcohol functions which is trisubstituted by radicals independently chosen from saturated alkyl radicals, at least one of the radicals alkyl containing at least one alcohol function.

15. Composition according to the preceding claim, characterized in that the saturated alkyl radicals are C 1 to C ₁₅ .

16. Composition according to the preceding claim, characterized in that the saturated alkyl radicals are d- C ₆ .

17. Composition according to claim 16, characterized in that the polyol is chosen from trimethylol propane, pentaerythritol and their mixtures.

18. Composition according to claim 16, characterized in that the polyol is neopentyl glycol.

19. Composition according to claim 2 or 3, characterized in that the polyol comprises a number of carbon atoms ranging from 2 to 20, preferably from 3 to 10.

20. Composition according to claim 2, characterized in that the polyol is chosen from ethylene glycol, propylene glycol, butylene glycol, polyethylene glycol different from a compound of formula HO (C _n H _2n O) _rn H such that n is equal to 2 or 3 and m is between 2 and 4, polypropylene glycol, glycerol, diglycerol, triglycerol, isopentyldiol, sorbitol and their mixtures.

21. Composition according to claim 3, characterized in that the polyol is chosen from ethylene glycol, propylene glycol, butylene glycol, polyethylene glycol, polypropylene glycol, glycerol, diglycerol, triglycerol, isopentyldiol , sorbitol and their mixtures.

22. Composition according to claim 1, characterized in that the ester is chosen from neopentylglycol di-neopentanoate and neopentylglycol di-neoheptanoate.

23. Composition according to claim 2 or 3, characterized in that the ester is chosen from glyceryl tri-neopentanoate and glyceryl tri-neoheptanoate.

24. Composition according to claim 3, characterized in that the ester is glyceryl trineodecanoate.

25. Composition according to one of the preceding claims, characterized in that said ester is in liquid form at room temperature (25 ° C).

26. Composition according to one of the preceding claims, characterized in that the ester represents from 0.1 to 99.9%, preferably from 1 to 99% and better still from 5 to 90% of the total weight of the composition.

27. Composition according to one of the preceding claims, characterized in that the ester is in an amount sufficient to confer on the composition properties of shine and / or resistance over time and / or non-migration and / or comfort .

28. Composition according to one of the preceding claims, characterized in that it further comprises at least one coloring agent.

29. Composition according to one of the preceding claims, characterized in that the coloring agent represents from 0.001 to 60%, and better still from 0.01 to 50%, and better still, from 0.1 to 40% by weight total of the composition.

30. Composition according to one of the preceding claims, characterized in that it further comprises at least one filler.

31. Composition according to one of the preceding claims, characterized in that the filler represents from 0.01 to 35%, preferably from 0.05 to 25% and better still from 0.5 to 15% of the total weight of the composition .

32. Composition according to one of the preceding claims, characterized in that it comprises at least one additional non-aqueous compound chosen from oils, fatty substances which are pasty at room temperature, waxes, gums, resins, lipophilic polymers and their mixtures.

33. Composition according to one of the preceding claims, characterized in that the additional non-aqueous compound (s) represent from 0.001 to 90% of the total weight of the composition, preferably from 0.05 to 60% and better still from 1 to 50%.

34. Composition according to one of the preceding claims, characterized in that it also comprises at least one wax.

35. Composition according to one of the preceding claims, characterized in that the wax represents from 0.01 to 50%, preferably from 2 to 40%, and better still from 5 to 30% of the total weight of the composition.

36. Composition according to one of the preceding claims, characterized in that it is in the form of a makeup and / or care product for the face or the body, the lips and / or the integuments.

37. Composition according to one of the preceding claims, characterized in that it is in the form of a makeup product for the facial skin.

38. Composition according to one of the preceding claims, characterized in that it is in the form of a lip makeup product.

39. Composition according to the preceding claim, characterized in that it is in anhydrous form.

40. Composition according to the preceding claim, characterized in that it is in the form of an emulsion, such as an oil-in-water or water-in-oil emulsion.

41. Use of at least one ester resulting from the reaction of a polyol with a carboxylic acid of the following formula (I): R ₂

R C COOH (I)

R \, 3

in which Ri, R ₂ and R ₃ are radicals independently chosen from alkyl, aryl, aralkyl radicals, optionally functionalized, and their associations, characterized in that said polyol is chosen from polyols comprising a carbon atom, located in alpha carbon carrying an alcohol function, which is trisubstituted by radicals chosen independently of one another from the alkyl, aryl, aralkyl radicals and their associations, at least one of the alkyl, aryl, aralkyl radicals containing at least one alcohol function, said polyol not being trimethyl-2,2,4-pentanediol-1, 3, in a cosmetic composition as an agent for giving said composition hold properties, in particular color, and / or shine and / or comfort and / or non-migration.

42. Use of at least one ester resulting from the reaction of a polyol with a carboxylic acid of formula (I) below: R ₁ C COOH (I)

R, in which R, R ₂ and R ₃ are radicals chosen independently from alkyl, aryl, aralkyl radicals, optionally functionalized, and their associations, characterized in that said polyol is chosen from polyols comprising a carbon atom, located in alpha carbon carrying an alcohol function, which is trisubstituted by radicals chosen independently of each other from the alkyl, aryl, aralkyl radicals and their associations, at least one of the alkyl, aryl, aralkyl radicals containing at less an alcohol function, said polyol not being trimethyl-2,2,4-pentanediol-1, 3 in a cosmetic composition having hold properties, in particular color, and / or shine and / or comfort and / or non-migration.

43. Use of at least one ester resulting from the reaction of a polyol with a carboxylic acid of formula (I) below:

R

in which R ₍ R ₂ and R ₃ are radicals chosen independently from alkyl, aryl, aralkyl radicals, optionally functionalized, and their associations, said acid comprising from 5 to 9 carbon atoms and said polyol not being a compound of formula HO (C _n H _2n O) _m H such that n is equal to 2 or 3 and m is between 2 and 4, in a cosmetic composition as an agent for giving said composition hold properties, in particular color, and / or shine and / or comfort and / or non-migration.

44. Use of at least one ester resulting from the reaction of a polyol with a carboxylic acid of formula (I) below:

R

R ₁ C COOH (I)

R, in which R ^ R ₂ and R ₃ are radicals chosen independently from alkyl, aryl, aralkyl radicals, optionally functionalized, and their associations, said acid comprising from 5 to 9 carbon atoms and said polyol not being a compound of formula HO (C _n H _2n O) _m H such that n is equal to 2 or 3 and m is between 2 and 4. in a cosmetic composition having hold properties, in particular color, and / or shine and / or comfort and / or non-migration.

45. Use of at least one ester resulting from the reaction of a polyol with a carboxylic acid of formula (I) below: R,

R COOH d)

R

in which R _{1 (} R ₂ and R ₃ are radicals chosen independently from alkyl, aryl, aralkyl radicals, optionally functionalized, and their associations, said ester comprising at least three ester functions. in a cosmetic composition as an agent for imparting to said composition of the holding properties, in particular of the color, and / or of gloss and / or of comfort and / or of non-migration.

46. Use of at least one ester resulting from the reaction of a polyol with a carboxylic acid of formula (I) below:

R

R., C COOH (I)

R, in which R ^ R ₂ and R ₃ are radicals chosen independently from alkyl, aryl, aralkyl radicals, optionally functionalized, and their associations, said ester comprising at least three ester functions. in a cosmetic composition having hold properties, in particular color, and / or shine and / or comfort and / or non-migration.