FR2838049A1 - Composition useful as a cosmetic make-up or care product has a fatty phase comprising a polyol ester of a trisubstituted acetic acid - Google Patents

Abstract

Composition with a fatty phase comprising a polyol ester of a trisubstituted acetic acid (I) is new. Composition with a fatty phase comprising a polyol ester of a trisubstituted acetic acid of formula (I) is new. R1-R3 = alkyl, aryl or aralkyl. An Independent claim is also included for imparting staying power, shine, comfort and/or non-migration properties to a film of cosmetic composition by including an ester as above in the composition.

Description

<Desc / Clms Page number 1>

 The present invention relates to a composition, especially for make-up or skincare, including scalp, both of the face and of the human body, of the lips or integuments of human beings, such as the hair, the eyelashes, eyebrows or nails, comprising a physiologically acceptable medium that contains a fatty phase comprising a particular ester. This composition has remarkable cosmetic properties, especially hold, and gives the 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 keratinous substances (skin, lips, superficial body growths) having, in particular, care and / or non-therapeutic treatment properties. It is especially a lipstick or a lip gloss, a foundation, a loose or compact powder, a blush, an eye shadow, a make-up base, a concealer, a tattoo product, a mascara, an eye -liner, a nail polish, an artificial tanning product for the skin, a product for coloring or hair care.

The use of silicone compounds in cosmetic compositions, in particular makeup compositions, is known to formulators. For example, the patent EP-A-0407205 describes a composition comprising the combination of a silicone gum and a silicone oil which makes it possible to obtain good properties for holding, spreading and comforting the skin. composition.

These compounds indeed confer on the cosmetic compositions excellent sensory properties, in particular a non-greasy feel, spreading and sliding 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 in order to increase the resistance of cosmetic compositions, in particular make-up compositions, and / or to reduce their migration.

By "migration" is meant an overflow of the composition (and in particular the color) out of the initial makeup pattern, resulting in an unsightly effect. Migration is often cited by women as a major flaw in lipsticks and classic eyeshadow.

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

However, the silicone compounds may have compatibility problems (solubility) with other hydrocarbon compounds conventionally used in cosmetic compositions, which limits its use.

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

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

The use of such esters makes it possible to obtain compositions having good cosmetic and sensory properties, especially withstand, in particular color, non-migration and comfort, non-irritating for keratin materials and having a more or less brilliant adapted to the desire of the consumers.

<Desc / Clms Page number 2>

dans laquelle Ri, R2 et R3 sont des radicaux choisis indépendamment parmi les radicaux alkyle, aryle, aralkyle, et leurs associations. The present invention therefore more precisely relates to 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 (1) below:

wherein R 1, R 2 and R 3 are radicals independently selected from alkyl, aryl, aralkyl, and combinations thereof.

The word ester, according to the invention, means a monoester, a diester, a triester or more generally a polyester. The ester of the composition according to the invention may result from a total or partial esterification (in the latter case, the ester has one or more free OH functions).

By at least one ester is meant one or more esters.

By physiologically acceptable is meant non-toxic and may be applied to the skin, skin appendages or lips of humans.

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

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 and aralkyl radicals, and their combinations, these radicals possibly being identical or different. This carbon atom is therefore directly bonded to 4 carbon atoms and is called neo carbon.

An acid having such a structure is called neo acid and will be so named in the rest of the text.

The term "alkyl radical" is intended to mean a saturated or unsaturated, branched or unbranched aliphatic hydrocarbon-based chain containing in particular from 1 to 28 carbon atoms.

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

By aryl radical is meant a radical derived from an aromatic cyclic compound by removal 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'-C6H5 type, R 'being a C1-C5 alkyl, such as for example the benzyl or phenethyl radicals.

These alkyl, aryl or aralkyl radicals may be functionalized, which means that they may comprise in their structure a heteroatom, that is to say a different atom of the carbon atom (such as an oxygen atom, nitrogen, sulfur, fluorine) or a functional group such as a COOH, OH, NHR or COOR group.

The subject of the present invention is also the use of at least one ester resulting from the reaction of a polyol with a carboxylic acid of formula (I) as defined above, in a cosmetic composition, as an agent for conferring on said composition of the

<Desc / Clms Page number 3>

 resistance properties, in particular color, and / or gloss and / or comfort and / or non-migration properties.

Another subject of the present invention is the use of at least one ester resulting from the reaction of a polyol with a carboxylic acid of formula (1), as defined above, in a cosmetic composition having holding properties, in particular color, and / or gloss and / or comfort and / or non-migration.

The present invention also relates to a cosmetic process for conferring on a film of a cosmetic composition holding properties, in particular color, and / or gloss and / or comfort and / or non-migration, of introducing into said composition at least one ester resulting from the reaction of a polyol with a carboxylic acid of formula (1) as defined above.

The neo carboxylic acid can be a monoacid or a polyacid, that is to say that at least one of the radicals R1, R2 or R3 contains a functional group -COOH. Preferably, the carboxylic acid is a monoacid. Preferably, the radicals R 1, R 2 and R 3 are independently selected from nonfunctionalized alkyl, aryl or aralkyl radicals.

Advantageously, the radicals R 1, R 2 and R 3 are independently selected from saturated alkyl radicals, preferably from saturated C 1 -C 15 alkyl radicals, and more preferably C 1 -C 6 alkyl radicals, for example methyl, ethyl, propyl or isopropyl radicals. pentyl, hexyl.

Advantageously, the neo carboxylic acid comprises a total number of carbon atoms ranging from 5 to 30, and better still from 5 to 15.

C3H7-C(CH3)2-COOH, l'acide néodécanoïque de formule C6H13-C(CH3)2-COOH, et leurs mélanges. A carboxylic acid neo chosen from neopentanoic acid of formula CH 3 -C (CH 3) 2 -COOH is preferably used, neoheptanoic acid of formula

C3H7-C (CH3) 2-COOH, neodecanoic acid of formula C6H13-C (CH3) 2-COOH, and mixtures thereof.

More preferably, the neo carboxylic acid is neopentanoic acid.

The ester of the composition according to the invention results from the reaction of a neo carboxylic acid as described above with a polyol.

By polyol is meant a linear or cyclic hydrocarbon chain, branched or unbranched, comprising at least two hydroxyl (OH) functions. The polyol may be chosen from diols, triols or tetraols.

Advantageously, the polyol comprises a number of carbon atoms ranging from 2 to 20, and preferably from 2 to 10.

Preferably, the polyol is chosen from the neo polyols, that is to say the polyols which contain a carbon atom, located in alpha of one of the alcohol functions, which is trisubstituted by radicals chosen independently from the alkyl and aryl radicals, aralkyl and their associations. This carbon atom directly linked to 4 other carbon atoms is therefore a neo carbon as defined above.

In this type of polyol, at least one of the alkyl, aryl and aralkyl radicals contains at least one alcohol function of the polyol, the alkyl, aryl and aralkyl radicals being as defined above.

Advantageously, the polyol contains a carbon atom located in alpha of one of the alcohol functions which is trisubstituted by radicals chosen independently from saturated alkyl radicals, preferably saturated alkyl radicals C1-C15, and better still Ci-Ce, at least one of the alkyl radicals containing at least one alcohol function.

<Desc / Clms Page number 4>

 The polyol that can be used to obtain the ester of the composition according to the invention may be chosen from propylene glycol, butylene glycol, glycerol, isopentyl diol and sorbitol, and mixtures thereof. Among these polyols, glycerol is preferentially chosen.

HOCH2-C(CH3)2-CH20H, le triméthylol propane de formule HOCHZ-C(C2Hs)(CH20H)2, le pentaérythritol de formule HOCH2-C(CH20H)2-CH20H et leurs mélanges. De façon préférentielle, le polyol est le néopentyl glycol. As the neo polyol, neopentyl glycol of formula

HOCH 2 -C (CH 3) 2 -CH 2 OH, 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 and mixtures thereof. Preferably, the polyol is neopentyl glycol.

Preferably, the ester of the composition according to the invention is in liquid form at ambient temperature (25 ° C.) and atmospheric pressure (760 mmHg or 1.01 × 10 5 Pa).

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

The ester used in the composition according to the invention may advantageously be chosen from neopentyl glycol di-neopentanoate (C15), neopentyl glycol di-neoheptanoate (C19), glyceryl tri-neopentanoate (C18) and tri-neoheptanoate. glyceryl (C24), glyceryl trineodecanoate (C33), and mixtures thereof. (The Cn in parentheses represents the total number of carbon atoms of the cited compound).

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 ester of the composition according to the present invention may 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 5 to 60% of the total weight of the composition.

Advantageously, the ester is in an amount sufficient to give the composition gloss and / or hold properties over time and / or non-migration and / or comfort.

This ester can be prepared according to the methods known to those skilled in the art. For example, the following documents can be cited in which the synthesis of this compound is described: PAWLENKO Justus, Liebigs Ann. Chem. 663 (1963); M. FEFER and A. J. 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 US-A-3,441,600 and US-A-3,523,084 to SINCLAIR RESEARCH INC.

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

By pigments, it is necessary to include white or colored particles insoluble in the liquid fatty phase of the composition, intended to color and / or opacify the composition.

By nacres or pearlescent pigments must be understood iridescent particles, especially produced by some shellfish in their shell or synthesized, insoluble in the liquid fatty phase of the composition.

By dyes, it is necessary to understand generally organic compounds soluble in fatty substances such as oils or in a hydroalcoholic phase.

Fat-soluble dyes are, for example, Sudan Red, D & C Red No. 17, D & C Green No. 6, (3-carotene, soybean oil, Sudan Brown, D & C Yellow No. 11, D & C Violet No. 2, D & C Orange No. 5, yellow quinoline, annatto, bromoacids.

<Desc / Clms Page number 5>

The water-soluble dyes are, for example, beet juice, methylene blue, caramel. The liposoluble and water-soluble dyes may represent from 0.001 to 20% of the total weight of the composition and better still from 0.1 to 6%.

The pigments may be white or colored, mineral and / or organic, coated or uncoated.

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

The nacres or pearlescent pigments may be chosen from white pearlescent pigments such as mica coated with titanium, or bismuth oxychloride, colored pearlescent pigments such as titanium mica with iron oxides, titanium mica with especially 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 liquid crystal or multilayer properties.

The nacres may be present in the composition in a proportion 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 more preferably from 0.01 to 50%, and more preferably from 1 to 40% of the total weight of the composition.

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

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

polyvinylidènelacrylonitrile telles que l'Expancel (Nobel Industrie), les particules de polymère acrylique, notamment de copolymère d'acide acrylique comme le Polytrap (Dow Coming) et les microbilles de résine de silicone (Tospearls de Toshiba, par exemple), le carbonate de calcium précipité, le dicalcium phosphate, le carbonate et l'hydro-carbonate de magnésium, l'hydroxyapatite, les microsphères de silice creuses (Silica Beads de Maprecos), les microcapsules de verre ou de céramique, les savons métalliques dérivés d'acides organiques carboxyliques ayant de 8 à 22 atomes de carbone, de préférence de 12 à 18 atomes de carbone, par exemple le stéarate de zinc, de magnésium ou de lithium, le laurate de zinc, le myristate de magnésium, et leurs mélanges. Ces charges peuvent être traitées ou non en surface notamment pour les rendre lipophiles. By charge is meant any colorless or white particle selected from inorganic 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-p-alanine and polyethylene, tetrafluoroethylene polymer powders (Teflon®). , lauroyl-lysine, starch, boron nitride, polymeric hollow microspheres such as

polyvinylidene acrylonitrile such as Expancel (Nobel Industry), acrylic polymer particles, especially acrylic acid copolymer such as Polytrap (Dow Coming) and silicone resin microbeads (Toshiba Tospearls, for example), precipitated calcium, dicalcium phosphate, magnesium carbonate and hydro-carbonate, hydroxyapatite, hollow silica microspheres (Silica Beads from Maprecos), glass or ceramic microcapsules, metallic soaps derived from organic acids carboxylic acids having 8 to 22 carbon atoms, preferably 12 to 18 carbon atoms, for example zinc, magnesium or lithium stearate, zinc laurate, magnesium myristate, and mixtures thereof. These fillers may or may not be treated on the surface, in particular to render them lipophilic.

Preferably, the fillers have a particle size of less than 50 m 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.

<Desc / Clms Page number 6>

 The composition according to the invention may advantageously comprise at least one additional nonaqueous compound different from the ester used in the composition according to the invention, chosen from oils, pasty fatty substances at ambient temperature, waxes, gums, resins, lipophilic polymers and mixtures thereof.

This additional non-aqueous compound may 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 contains, in addition, at least one wax. For the purposes of the present invention, the term "wax" is understood to mean a lipophilic fat compound, solid at room temperature (25 ° C.), with a reversible solid / liquid state change, having a melting temperature greater than 30 ° C. and up to at 200 ° C., a hardness greater than 0.5 MPa, and having in the solid state an anisotropic crystalline organization. The size of the crystals is such that the crystals diffract and / or diffuse the light, conferring on the composition a cloudy, more or less opaque appearance. By bringing the wax to its melting temperature, it is possible to render it miscible with oils and to form a homogeneous mixture microscopically, but by bringing the temperature of the mixture to room temperature, a recrystallization of the wax in the oils of the mixed.

The wax may be chosen from waxes that are solid at ambient temperature, such as hydrocarbon waxes, such as beeswax that may be modified, Camauba, Candellila, Ouricoury, Japan wax, cork fiber waxes or sugar cane, paraffin waxes, lignite waxes, microcrystalline waxes, lanolin wax, Montan wax, ozokerites, polyethylene waxes or ethylene copolymer waxes, waxes obtained by Fischer-Tropsch synthesis, hydrogenated oils, fatty esters and glycerides concrete at 25 C. It is also possible to use silicone waxes, among which mention may be made of alkyl, alkoxy and / or polymethylsiloxane esters. The waxes may be in the form of stable dispersions of colloidal wax particles such as may be prepared by known methods, such as "Microemulsions Theory and Practice", LM Prince Ed., Academy Press (1977), pages 21-32. Preferably, the waxes used have a melting point of at least 45 C.

The wax may 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 that can be used in the invention are generally in an oil-solubilized form and the resins can be liquid or solid at room temperature.

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

The additional oils may be hydrocarbon and / or silicone and / or fluorinated oils. These oils can be of animal, vegetable, mineral or synthetic origin. By "hydrocarbon oil" is meant an oil comprising mainly carbon and hydrogen atoms and optionally one or more functions selected from hydroxyl, ester, ether, carboxylic functions. As an example of additional oil that may be used in the invention, mention may be made of: hydrocarbon-based oils of animal origin, such as perhydrosqualene; vegetable hydrocarbon-based oils such as liquid triglycerides of fatty acids having from 4 to 10 carbon atoms, for instance triglycerides of heptanoic or octanoic acids or jojoba oil; linear or branched hydrocarbons of mineral or synthetic origin, such as liquid paraffins and their derivatives, petroleum jelly; esters and synthetic ethers, in particular of fatty acids, such as the oils of formula R 1 COOR 2 in which R 1 represents the residue of a higher fatty acid

<Desc / Clms Page number 7>

contenant de 1 à 40 atomes de carbone avec 10 s R + R2:9 41 comme par exemple, l'isononanoate d'isononyle, le myristate d'isopropyle, le palmitate d'éthyl 2-hexyle, le stéarate d'octyl 2-dodécyle, l'érucate d'octyl 2-dodécyle, l'isostéarate d'isostéaryle ; les esters hydroxylés comme l'isostéaryl lactate, l'octyl hydroxy stéarate, l'hydroxy stéarate d'octyl dodécyle, le diisostéaryl malate, des heptanoates, octanoates, décanoates d'alcools gras ; certains esters de polyol comme le dioctanoate de propylène glycol; - les alcools gras ayant de 12 à 26 atomes de carbone comme l'octyl dodécanol, le
2-butyloctanol, le 2-hexyl décanol, le 2-undécyl pentadécanol, l'alcool oléique ; les huiles fluorées éventuellement partiellement hydrocarbonées et/ou siliconées ; les huiles siliconées comme les polydiméthylsiloxanes (PDMS) volatiles ou non, linéaires ou cycliques ; les polydiméthylsiloxanes comportant des groupements alkyle, alcoxy ou phényle, pendant ou en bout de chaîne siliconée, groupements ayant de 2 à 24 atomes de carbone ; les silicones phénylées comme les phényl triméthicones (telles que la phényl triméthicone vendue sous le nom commercial DC556 par Dow Coming), les phényl diméthicones, les phényl triméthylsiloxy diphényl siloxanes, les diphényl diméthicones, les diphényl méthyldiphényl trisiloxanes, les 2-phényl éthyl triméthyl- siloxysilicates, - et leurs mélanges: Les huiles additionnelles peuvent représenter de 0,01 à 90 % du poids total de la composition, de préférence de 0,05 à 60 % et mieux de 1 à 35 %. having 1 to 40 carbon atoms and R2 is a hydrocarbon chain

containing from 1 to 40 carbon atoms with 10 s R + R2: 9 41 such as, for example, isononyl isononanoate, isopropyl myristate, 2-hexyl ethyl palmitate, 2- (2-) octyl stearate, dodecyl, octyl 2-dodecyl erucate, isostearyl isostearate; hydroxylated esters such as isostearyl lactate, octyl hydroxy stearate, octyl dodecyl hydroxystearate, diisostearyl malate, heptanoates, octanoates, decanoates of fatty alcohols; 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, oleyl alcohol; fluorinated oils that may be partially hydrocarbon-based and / or silicone-based; silicone oils, such as volatile or non-linear polydimethylsiloxanes (PDMSs), linear or cyclic; polydimethylsiloxanes comprising alkyl, alkoxy or phenyl groups, during or at the end of the silicone chain, groups having from 2 to 24 carbon atoms; phenyl silicones such as phenyl trimethicones (such as phenyl trimethicone sold under the trade name DC556 by Dow Coming), phenyl dimethicones, phenyl trimethylsiloxy diphenyl siloxanes, diphenyl dimethicones, diphenyl methyldiphenyl trisiloxanes, 2-phenyl ethyl trimethyl- siloxysilicates, and mixtures thereof: The additional oils may 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 comprise, in addition, 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 at a rate of 0 , 0005 to 20% of the total weight of the composition and better still from 0.001 to 10%.

By cosmetic active is meant a lipophilic or hydrophilic compound providing a benefit to keratin materials and more particularly to the skin and lips.

As a cosmetic active agent that may be used in the invention, mention may be made of vitamins A, E, C, B3, F, provitamins such as D-panthenol, soothing active agents such as a-bisabolol, aloe vera and allantoin. , plant extracts or essential oils, protective or restructuring agents such as ceramides, freshness actives such as menthol and its derivatives, emollients (cocoa butter, dimethicone), moisturizers (arginine PCA), anti-wrinkle active agents, 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 quantity in such a way that the advantageous properties of the composition according to the invention are not or not substantially impaired by the addition envisaged.

The applications of the compositions according to the invention are numerous and relate to all colored or non-colored cosmetic products and more particularly to lip makeup products such as lipsticks or lip glosses and make-up products for the complexion, namely facial skin, such as foundations, anticemes, loose or compacted powder, blushers, eyes blushes, makeup bases.

In a particular embodiment of the invention, the compositions according to the invention can be prepared in the usual manner by those skilled in the art. They may be in the form of a cast product, for example in the form of a stick or stick, or in the form of a cup that can be used by direct contact or with a sponge or in a hot-water bottle. In particular, they find an application as a cast foundation, make-up

<Desc / Clms Page number 8>

 cheeks or eyelids poured, lipstick, base or lip care balm, anti-cream product. They can also be in the form of a soft paste or gel, more or less fluid cream. They can then constitute foundations or lipsticks, lip glosses (gloss in English terminology), sunscreen products or skin coloring.

The compositions of the invention may be anhydrous and contain less than 5% added water relative to the total weight of the composition. They can then be in particular in the form of an oily gel, oily liquid, paste or stick or in the form of a vesicular dispersion containing ionic and / or nonionic lipids.

They may also be in the form of an oily or aqueous continuous phase single or multiple emulsion, oily dispersion in an aqueous phase by means of vesicles containing ionic and / or nonionic lipids. These galenic 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, of skincare, in the form of a sunscreen or make-up removing composition or in the form of a hygienic composition. If it contains cosmetic active ingredients, it can then be used as a basis for care or non-therapeutic treatment for the skin such as the hands or face or for the lips (lip balms, protecting the lips from the cold and / or the sun and / or wind), artificial tanning product of the skin.

The composition of the invention may also be in the form of a colored makeup product of the skin, in particular the face as a blush, a blush or eyeshadow, body makeup as a semi tattoo product -permanent or lip makeup such as a red or a lip gloss, possibly having care properties or non-therapeutic treatment, a make-up product for integuments such as, for example, nail polish, mascara, eyeliner, a product coloring or hair 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 makeup product for the complexion, 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, especially an oil-in-water emulsion.

The composition according to the invention can be manufactured by known methods, generally used in the cosmetics field.

The following examples are intended to illustrate in a nonlimiting manner the object of the present invention. Quantities are given as a percentage by mass.

EXAMPLE 1 Measurements of viscosity and properties of spreading of compounds according to the invention and according to the prior art.

The inventors have compared the viscosities and the spreading properties of the following compounds: polydimethylsiloxane manufactured or marketed by Dow Corning under the reference DOW CORNING FLUID 200 - 5 cSt which is a silicone oil commonly used in cosmetic compositions prior art.

<Desc / Clms Page number 9>

Neopentyl glycol di-neopentanoate manufactured or marketed by the company BSI under the reference NEOFEEL 55, which is an ester as used in the composition according to the invention.

1.1 Viscosity Measurements Viscosity is measured at 20 C using a Brookfield DV-II + type LV viscometer with a number 1 rotating at 100 rpm.

The results are given in the following table:
Table (I)

<Tb>
<tb> Compound <SEP> Viscosity <SEP> to <SEP> 20 C
<tb> (in <SEP> cP)
<tb> polydimethylsiloxane <SEP> 7.56
<tb> (DOW <SEP> CORNING <SEP> FLUID <SEP> 200 <SEP> - <SEP> 5cSt)
<tb> di-neopentanoate <SEP> of <SEP> neopentyl <SEP> glycol <SEP> 11.1
<Tb>

NEOFEEL 55 1.2. Mesure des propriétés d'étalement On prépare un support constitué d'un papier filtre sans cendre d'une porosité de 25 m et d'un diamètre de 90 mm, commercialisé par la société Prolabo.

NEOFEEL 55 1.2. Measurement of the Spreading Properties A support consisting of an ashless filter paper with a porosity of 25 m and a diameter of 90 mm, marketed by Prolabo, is prepared.

0.1 ml of the test compound which is deposited at the center of the filter paper is then removed and then allowed to migrate at 20 ° C.

After 20 minutes, measure the diameter of the task obtained using a millimeter rule and then calculate the surface of the stain according to the following formula: surface of the task = (# X (diameter of the task) 2) / 4.

This surface measurement is performed 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)

<Tb>
<tb> Compound <SEP> Spread <SEP> Spread <SEP> type
<tb> (in <SEP> cm2)
<tb> Polydimethylsiloxane <SEP> 29.8 <SEP> 2,3
<tb> (DOW <SEP> CORNING <SEP> FLUID <SEP> 200 <SEP> - <SEP> 5cSt)
<tb> Di-neopentanoate <SEP> of <SEP> neopentyl <SEP> glycol <SEP> 29 <SEP> 1,1
<tb> (NEOFEEL <SEP> 55 <SEP>#)
<Tb>
These results show that neopentyl glycol polydimethylsiloxane and neopentyl glycol di-neopentanoate have similar viscosities and spreading properties. It is therefore possible to substitute polydimethylsiloxane with neopentyl glycol di-neopentanoate in a cosmetic formulation and to obtain similar cosmetic properties while having properties, especially non-migration, higher. This is demonstrated in the following examples.

<Desc / Clms Page number 10>

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)

<Tb>
<tb> Materials <SEP> first <SEP> Example <SEP> 2 <SEP> Example <SEP> 3
<tb> (invention) <SEP> (comparative)
<tb> Phase <SEP> A
<tb> Malate <SEP> of <SEP> di-isostearyl <SEP> 4.1 <SEP> 4.1
<tb> Wax <SEP> of <SEP> lanolin <SEP> oxypropylenate <SEP> 4.1 <SEP> 4.1
<tb> Polybutylene <SEP> 8.2 <SEP> 8.2
<tb> Octyl <SEP> -2 <SEP> dodecanol <SEP> 4.1 <SEP> 4.1
<tb> Neopentanoate <SEP> octyl-2 <SEP> dodecylate <SEP> 0.9 <SEP> 0.9
<tb> BHT <SEP> 0.04 <SEP> 0.04
<tb> Phase <SEP> B
<tb> Polyisobutene <SEP> hydrogenated <SEP> (manufactured <SEP> or <SEP> qsp <SEP> 100 <SEP> qsp <SEP> 100 <SEP>
<tb> marketed <SEP> under <SEP> the <SEP> reference <SEP> Parleam #
<tb> by <SEP> the <SEP> company <SEP> Nippon <SEP> Oil <SEP> and <SEP> Fats
<Tb>

Hectorite modifiée (BentoneCBJ38V 0,8 0,8

Modified hectorite (BentoneCBJ38V 0.8 0.8

<Tb>
<tb> Elementis)
<tb> Phase <SEP> C
<tb> Wax <SEP> of <SEP> Polyethylene <SEP> (Mw * <SEP> = <SEP> 500 <SEP> g / mol) <SEP> 10.8 <SEP> 10.8
<tb> octacosanyl stearate <SEP><SEP> 3 <SEP> 6 <SEP> 3,6
<tb> Coconut glycerides <SEP> hydrogenated <SEP> 5 <SEP> 5
<tb> Phase <SEP> D
<tb> Titanium <SEP> dioxide <SEP> 2.7 <SEP> 2.7
<tb> DC <SEP> Red <SEP> 7 <SEP> 2.2 <SEP> 2.2
<tb> DC <SEP> Red <SEP> 27 <SEP> Aluminum <SEP> Lake <SEP> 1.8 <SEP> 1.8
<tb> Yellow <SEP> 6 <SEP> aluminum <SEP> lake <SEP> 3 <SEP> 3
<tb> Iron <SEP> oxides <SEP> (CI <SEP> 77499) <SEP> 2 <SEP> 2
<tb> Phase <SEP> E
<tb> Polydimethylsiloxane- <SEP> 17.3
<tb> (DOW <SEP> CORNING <SEP>#<SEP> 200 <SEP> FLUID <SEP> - <SEP> 5 <SEP> is)
<tb> Di-neopentanoate <SEP> of <SEP> neopentyl <SEP> glycol <SEP> 17.3
<Tb>

(NEOFEEL55)

(NEOFEEL55)

<Tb>
<tb> Phase <SEP> F <SEP> ~~~
<tb> Acetate <SEP> of alpha <SEP> tocopheryl <SEP> 0.3 <SEP> 0.3
<tb> Methoxycinnamate <SEP> Ethylhexyl <SEP> 0.7 <SEP> 0.7
<tb> Perfume <SEP> 0.2 <SEP> 0.2
<tb> * Mw <SEP> = <SEP> mass <SEP> molar
<Tb>
Procedure In a first step, the pigments (phase D) are dispersed and ground in phase A using a three-roll mill.

In parallel, a Bentone gel (phase B) is prepared by dispersing, using a high pressure homogenizer, the Bentone in Parléam.

The pigments ground in phase A and the Bentone gel # are put in a skillet in which the waxes are added (phase C), then heated at 100 ° C. for 2 hours and homogenized using a Raynerie stirrer. .

<Desc / Clms Page number 11>

Phase E is then added as well as the active ingredients (phase F) and the mixture is homogenized for 5 min and then poured into a suitable mold at 42 ° C to form sticks.

The mold is then placed at -20 ° C. for half an hour and then the sticks are demolded.

Sensory Evaluation The compositions of Examples 2 and 3 were applied by half-lips to a panel of 5 qualified persons and evaluated according to various criteria.

The ratings on the different criteria are between 0 (not) and 10 (very) inclusive.

The results are shown in Table (IV) below.

Table (IV)

<Tb>
<tb> Results
<tb> Evaluated <SEP> Criteria <SEP> Example <SEP> 2 <SEP> Example <SEP> 3
<tb> (Invention) <SEP> (Comparative)
<tb> A <SEP> the <SEP> application of the <SEP> stick <SEP> on <SEP> the <SEP> lips
<tb> slippery <SEP> 6.4 <SEP> 7
<tb> oily <SEP> / <SEP> fat <SEP> 4.8 <SEP> 4.8
<tb> sweetness <SEP> 7.8 <SEP> 7.4
<tb> sec <SEP> 2,8 <SEP> 2,6
<tb> sticky <SEP> 1.8 <SEP> 2
<tb> thickness <SEP> of <SEP> film <SEP> 4,5 <SEP> 4,8
<tb> homogeneity <SEP> of <SEP> film <SEP> 7 <SEP> 7
<tb> gloss <SEP> 5.8 <SEP> 5.6
<tb> coverage ** <SEP> 6.6 <SEP> 7
<tb> After <SEP> app
<tb> brightness <SEP> 5.4 <SEP> 5.4
<tb> sticky <SEP> 2.2 <SEP> 2
<tb> approval <SEP> of application <SEP> 7.1 <SEP> 7
<tb> result <SEP> makeup <SEP> 6.8 <SEP> 6.6
<tb><SEP> Quality <SEP> Product <SEP> 7.1 <SEP> 6.9
<tb> After <SEP> one <SEP> hour
<tb> comfort <SEP> 5.8 <SEP> 6.2
<tb> sticky <SEP> 2.4 <SEP> 2.1
<tb> holding <SEP> of <SEP> film <SEP> 6.8 <SEP> 6.5
<tb> migration <SEP> 2.8 <SEP> 3.8
<tb> gloss <SEP> 3,4 <SEP> 3,2
<Tb>
(** 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 greater than 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 in particular has excellent sliding properties, softness, coverage and amenity to application as well as comfort and holding the composition film over time.

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

Neopentyl glycol di-neopentanoate can therefore advantageously be substituted for polydimethylsiloxane in cosmetic compositions in order to obtain the properties mentioned above.

<Desc / Clms Page number 12>

Example 4 Lipstick Stick Examples 2 and 3 are prepared according to the procedure, a composition according to the invention containing glyceryl tri-neopentanoate manufactured or marketed by the company BSI under the reference NEOFEEL TNP # Malate di- isostearyl 4.1 Lanolin oxypropylenated wax 4.1 Polybutylene 8.2 Octyl -2 dodecanol 4.1 Octoyl-2-dodecyl neopentanoate 0.9 BHT 0.04 Polyisobutene hydrogenated (manufactured or marketed as 100 under the reference Parléam by company Nippon Oil and Fats) Modified hectorite (Elementis Benton 38V) 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 Iron oxides (CI 77499) 2 Glyceryl tri-neopentanoate (manufactured or marketed 17.3 by BSI under the reference NEOFEEL TNP Alpha tocopheryl acetate 0.3 Ethylhexyl methoxycinnamate 0.7 Perfume 0, 2 * Mw = molar mass A stick of lipstick is obtained which allows the deposition of a film of lipstick of good behavior, comfortable, non-irritating and which migrates little or not at all.

EXAMPLE 5 Founding composition A foundation composition is prepared which contains, as ester of the invention, glyceryl tri-neopentanoate manufactured or marketed by the company BSI under the reference NEOFEEL TNP # Oily phase Tri-neopentanoate of glyceryl (manufactured or marketed by the 29.4 BSI company under the reference NEOFEEL TNP #) cetyldimethicone copolyol (manufactured or marketed by the company Goldschmidt under the reference Abil EM 90) Mixture of acetylated glycol stearate and tristearin (manufactured or 0, 5 sold by Guardian under the reference Unitwix) Propylparaben 0.1 Aqueous phase Water 57.2 Magnesium sulphate 0.7 Glycerol 5 Methylparaben 0.1 Pigments Feroyl oxide coated with triisostearyl isopropyl titanate (ITT) 0.6 Red iron oxide coated ITT 0.39

<Desc / Clms Page number 13>

 ITT-coated black iron oxide 0.11 ITT-coated titanium dioxide 2.9 Procedure The pigments are dispersed in 4% tri-neopentanoate glyceryl using a three-roll mill (3 passes are made in the grinder) .

The rest of the constituents of the oily phase are weighed together and then heated to 70 C.

The crushed and then homogenized pigments are added to the oily phase with stirring at the Moritz stirrer (at a speed of 1000 rpm).

In parallel, the constituents of the aqueous phase are weighed together and then heated to 80 C.

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

The mixture is then allowed to gradually return to room temperature while maintaining stirring.

The foundation obtained is in the form of cream. It has good non-migration properties while being comfortable.

Claims (40)

 wherein R 1, R 2 and R 3 are radicals independently selected from alkyl, aryl, aralkyl, and combinations thereof.

 1. 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: 2. Composition according to one of the preceding claims, characterized in that the radicals R1, R2 and R3 are independently selected from saturated alkyl radicals. 3. Composition according to one of the preceding claims, characterized in that the radicals R1, R2 and R3 are independently selected from saturated alkyl radicals. C1-C15. 4. Composition according to one of the preceding claims, characterized in that the radicals R1, R2 and R3 are independently selected from saturated alkyl radicals. The It 5. Composition according to one of the preceding claims, characterized in that the carboxylic acid comprises a total number of carbon atoms ranging from 5 to 30. 6. Composition according to one of the preceding claims, characterized in that the carboxylic acid comprises a total number of carbon atoms ranging from 5 to 15. 7. Composition according to one of the preceding claims, characterized in that the carboxylic acid is a monoacid. 8. Composition according to one of the preceding claims, characterized in that the carboxylic acid is selected from neopentanoic acid, neoheptanoic acid, neodecanoic acid, and mixtures thereof. 9. Composition according to one of the preceding claims, characterized in that the carboxylic acid is neopentanoic acid. 10. Composition according to one of the preceding claims, characterized in that the polyol is a diol, a triol or a tetraol. 11. Composition according to the preceding claim, characterized in that the polyol comprises a number of carbon atoms ranging from 2 to 20. 12. Composition according to one of the preceding claims, characterized in that the polyol comprises a number of carbon atoms ranging from 2 to 10. <Desc / Clms Page number 15> 13. Composition according to one of the preceding claims characterized in that the polyol is selected from propylene glycol, butylene glycol, glycerol, isopentyl diol, sorbitol and mixtures thereof. 14. Composition according to one of the preceding claims characterized in that the polyol is glycerol. 15. Composition according to one of the preceding claims, characterized in that the polyol contains a carbon atom, located in alpha of one of the alcohol functions, which is trisubstituted by radicals chosen independently from the alkyl, aryl, aralkyl and their combinations, at least one of the alkyl, aryl, aralkyl radicals containing at least one alcohol function. 16. Composition according to one of the preceding claims, characterized in that the polyol contains a carbon atom located in alpha of one of the alcohol functions which is trisubstituted by radicals chosen independently from the saturated alkyl radicals, at least one of alkyl radicals containing at least one alcohol function. 17. Composition according to one of the preceding claims, characterized in that the polyol contains a carbon atom, located in alpha of one of the alcohol functions, which is trisubstituted by independently selected radicals alkyl radicals saturated with C1-C15, at least one of the alkyl radicals containing at least one alcohol function. 18. Composition according to one of the preceding claims, characterized in that the polyol contains a carbon atom, located in alpha of one of the alcohol functions, which is trisubstituted by radicals independently selected from saturated C 1 -C 6 alkyl radicals. at least one of the alkyl radicals containing at least one alcohol function. 19. Composition according to one of the preceding claims, characterized in that the polyol is selected from neopentyl glycol, trimethylol propane, pentaerythritol and mixtures thereof. 20. Composition according to one of the preceding claims, characterized in that the polyol is neopentyl glycol. 21. Composition according to one of the preceding claims characterized in that said ester is in liquid form at room temperature (25 C). 22. Composition according to one of the preceding claims, characterized in that the ester is chosen from neopentylglycol di-neopentanoate (C15), neopentylglycol di-neoheptanoate (C19), glyceryl tri-neopentanoate (Cie). , glyceryl tri-neoheptanoate (C24), glyceryl tri-neodecanoate (C33) - 23. 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. 24. Composition according to one of the preceding claims, characterized in that the ester is in an amount sufficient to give the composition gloss and / or withstand properties over time and / or non-migration and / or comfort . 25. Composition according to one of the preceding claims, characterized in that it further comprises at least one coloring agent. <Desc / Clms Page number 16>  26. Composition according to one of the preceding claims, characterized in that the coloring agent represents from 0.001 to 60%, and more preferably from 0.01 to 50%, and more preferably from 0.1 to 40% of the total weight. of the composition. 27. Composition according to one of the preceding claims, characterized in that it further comprises at least one filler. 28. 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. 29. Composition according to one of the preceding claims, characterized in that it comprises at least one additional non-aqueous compound chosen from oils, pasty fatty substances at room temperature, waxes, gums, resins, lipophilic polymers. and their mixtures. 30. Composition according to one of the preceding claims, characterized in that the additional non-aqueous compound or compounds 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%. 31. Composition according to one of the preceding claims, characterized in that it further comprises at least one wax. 32. 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 more preferably from 5 to 30% of the total weight of the composition. 33. Composition according to one of the preceding claims, characterized in that it is in the form of a makeup product and / or care of the face or body, lips and / or integuments. 34. Composition according to one of the preceding claims, characterized in that it is in the form of a makeup product for the skin of the face. 35. Composition according to the preceding claim, characterized in that it is in the form of an emulsion, such as an oil-in-water emulsion. 36. Composition according to one of the preceding claims, characterized in that it is in the form of a lip makeup product. 37. Composition according to the preceding claim, characterized in that it is in anhydrous form. 38. Use of at least one ester resulting from the reaction of a polyol with a carboxylic acid of formula (1) below:

 wherein R1, R2 and R3 are radicals independently selected from alkyl, aryl, aralkyl, and combinations thereof, in a cosmetic composition such as <Desc / Clms Page number 17>  agent for giving said composition holding properties, in particular color, and / or gloss and / or comfort and / or non-migration. 39. Use of at least one ester resulting from the reaction of a polyol with a carboxylic acid of formula (I) below:

 in which R 1, R 2 and R 3 are radicals chosen independently from alkyl, aryl and aralkyl radicals, and their combinations, in a cosmetic composition having holding properties, especially of color, and / or gloss and / or comfort and / or non-migration. 40. A cosmetic process for conferring on a film of a cosmetic composition resistance properties, in particular color and / or gloss and / or comfort and / or non-migration properties, comprising introducing into said composition at least one ester resulting from the reaction of a polyol with a carboxylic acid of formula (I) below:

 wherein R1, R2 and R3 are radicals independently selected from alkyl, aryl, aralkyl, and combinations thereof.