Thickening composition of polar or non-polar oils

Abstract

Thickening composition (C) of polar or non-polar oils (H2), comprising at least one oil (H1) and a poly(itaconate) (P)

Description

Title of the invention: Thickening composition of polar or non-polar oils

[0001] The present invention relates to a thickening composition of polar or apolar oils, to its manufacturing process and to topical formulations comprising this thickening composition.

[0002] There is a need to thicken oils in the cosmetics market. The formation of a gel requires the formation by a gelling agent of a three-dimensional network allowing the liquid phase or the solvent to be immobilized. To do this, several strategies can be implemented. They involve different types of interactions, weak (hydrogen bonds, hydrophobic / hydrophobic, etc.) and absorption / adsorption phenomena.

[0003] The thickening solutions currently proposed have interesting performances, significant advantages in terms of versatility, versatility, but also disadvantages, in particular the impact on the sensory properties of the formula, the formulation conditions. These substances are of different chemical natures: silica derivatives, clays, polymers of the polyamide type, polyacrylate, polyurethane, beeswax, hydrogenated vegetable oils or even esters or fatty amides of sugars.

[0004] Although there are already oil thickeners on the market, of different natures and performances, the relationships between the structures and their properties are not clearly identified, which constitutes the main scientific obstacle, because the objective is to find a structure obtained from materials of plant origin which would make it possible to present high performances with all types of oil natures (polar to non-polar), for different types of textures (compact to fluid) and interesting or at least non-prohibitive sensory properties (non-greasy, non-sticky, non-stringy).

[0005] One of the difficulties therefore lies in finding a single universal structure or substance that can effectively thicken, at low doses, all types of oils, from the most apolar to the most polar oils, the gelling mechanisms of course being different depending on the nature of the oil and the gelling agent.

[0006] A solution of the present invention is a thickening composition (C) of polar and / or apolar oils (H2), comprising at least one oil (H1) and a poly(itaconate) (P).

[0007] Said thickening composition (C) makes it possible to thicken oils (H2) of a polar nature and oils of a non-polar nature.

[0008] For the purposes of the present invention, the term “polar oil” denotes a hydrophobic compound which comprises in its molecular structure polar groups, namely capable of creating electrostatic interactions with water molecules, of the permanent dipole / permanent dipole type.

[0009] For the purposes of the present invention, the term “apolar oil” denotes a hydrophobic compound which cannot create electrostatic interactions with water molecules of the permanent dipole / permanent dipole type.

[0010] For the purposes of the present invention, the term “hydrophobic compound” means a compound which cannot physically interact with water.

[0011] For the purposes of the present invention, “oil” means a compound and / or a mixture of hydrophobic compounds, insoluble in water.

[0012] Preferably, the poly(itaconate) (P) will consist of: - by at least one monomeric unit derived from itaconic acid of formula (I) in free acid form or partially or totally salified

[0013] and - by at least one monomeric unit derived from a compound of formula (II):

[0014] with Y and Y' identical representing the radical -ORi, or Y and Y' different representing either the radical -OH or the radical -ORi, with Ri representing:

[0015] a) a linear or branched, saturated or unsaturated aliphatic hydrocarbon radical (IIa), comprising from 6 to 36 carbon atoms and optionally substituted with one or more hydroxyl groups,

[0016] or

[0017] b) a radical of formula (IIb) in which R2 represents a linear or branched, saturated or unsaturated, aliphatic hydrocarbon radical containing from 6 to 36 carbon atoms and optionally substituted with one or more hydroxyl groups: (Ilb)

[0018] Or

[0019] c) a radical of formula (Ile) in which R3-C(=O) represents a saturated or unsaturated, linear or branched hydrocarbon acyl radical containing from 12 to 24 carbon atoms, and more particularly a radical chosen from the elements of the group consisting of the dodecanoyl, tetradecanoyl, hexadecanoyl, octadecanoyl, eicosanoyl, docosanoyl, oleyl, linoleyl, linolenoyl or isostearyl radicals, and in which x represents a natural whole number greater than or equal to 1 and less than or equal to 5:

[0020]

[0021] (Island) Or d) a radical of formula (Ild) in which m represents a greater whole number or equal to 2 and less than or equal to 10:

[0022]

[0023] Or e) a radical of formula (Ile) in which o represents a greater whole number or equal to 2 and less than or equal to 4:

[0024]

[0025] Or f) a radical of formula (Ilf): (Island) (Ilf)

[0026]

[0027] Or g) a radical of formula (Ilg):

[0028]

[0029] (Ilg) h) a radical of formula (IIh) in which q represents an integer greater than or equal to 1 and less than or equal to 12, more particularly greater than or equal to 3 and less than or equal to 8: (Ilh)

[0030] , when Y and Y' represent the -OH radical, the carboxylic acid function then present in formula (II) is in free acid form or partially or totally salified.

[0031] For the purposes of the present invention, the term "salified" indicates that the acid function present in a monomer is in an anionic form associated in the form of a salt with a cation, in particular alkali metal salts, such as sodium or potassium cations, or as nitrogenous base cations such as the ammonium salt, the lysine salt or the monoethanolamine salt (HOCH2-CH2-NH4+). These are preferably sodium or ammonium salts.

[0032] By saturated or unsaturated, linear or branched aliphatic hydrocarbon radical, comprising from 6 to 36 carbon atoms, optionally substituted with one or more hydroxyl groups, is meant for the radical R1 of formula (IIa) and for the radical R2 of formula (IIb), as defined above: - Saturated linear alkyl radicals, for example n-hexyl, n-heptyl, n-octyl, n-nonyl, n-decyl, n-undecyl, n-dodecyl, n-tridecyl, n-tetradecyl, n-pentadecyl, n-hexadecyl, n-heptadecyl, n-octadecyl, n-nonadecyl, n-eicosyl, n-docosyl radicals;

[0033] - Unsaturated linear radicals such as octenyl, decenyl, un- decenyl, dodecenyl, tridecenyl, tetradecenyl, pentadecenyl, hexadecenyl, heptadecenyl, octadecenyl, nonadecenyl, eicosenyl, docosenyl, 4-dodecenyl, or 5-dodecenyl;

[0034] - Saturated or unsaturated, linear or branched aliphatic radicals, comprising 6 to 36 carbon atoms substituted by one or two hydroxy groups, such as hydroxydodecyl, hydroxytetradecyl, hydroxyhexadecyl, hydroxyoc-tadecyl, hydroxyeicosyl, hydroxydocosyl radicals, for example the 12-hydroxyoc-tadecyl radical.

[0035] - Radicals derived from isoalkanols of formula (1):

[0036] (CH3)(CH3)CH-(CH2)r-CH2-OH (1)

[0037] in which r represents an integer between 2 and 20, for example the radicals isodecyl, isoundecyl, isododecyl, isotridecyl, isotetradecyl, isopentadecyl, isohexadecyl, isopentadecyl, isooctadecyl, isononadecyl, isoeicosyl or isodocosyl;

[0038] Branched alkyl radicals, derived from Guerbet alcohols, of formula (2):

[0039] CH(CsH2s+1)(CtH2t+i)-CH2-OH (2)

[0040] in which t is an integer between 4 and 18, s is an integer between 2 and 18 and the sum s + t is greater than or equal to 6, and less than or equal to 22, for example the radicals 2-butyl octyl, 2-butyl decyl, 2-hexyl octyl, 2-hexyl decyl, 2-octyl decyl, 2-hexyl dodecyl, 2-octyl dodecyl, 2-decyl tetradecyl, 2-dodecyl hexadecyl, 2-tetradecyl octadecyl.

[0041] According to an even more particular aspect, in the definition of formulas (IIa) and (IIb) as defined above, R1 and R2 represent a radical chosen from at least one of the elements of the group consisting of the radicals n-hexyl, n-heptyl, n-octyl, n-nonyl, n-decyl, n-dodecyl, n-tetradecyl, n-hexadecyl, n-octadecyl, n-eicosyl, n-docosyl, 2-hexyl decyl, 2-octyl decyl, 2-hexyl dodecyl, 2-octyl dodecyl, 2-decyl tetradecyl, 12-hydroxy octadecyl.

[0042] According to a particular aspect, the poly(itaconate) (P) is a crosslinked poly(itaconate) (P).

[0043] For the purposes of the present invention, crosslinked poly(itaconate) (P) denotes poly(itaconate) (P) as defined above and further consisting of at least one monomeric unit derived from a polyethylene crosslinking monomer (AR).

[0044] By polyethylene crosslinking monomer (AR) is meant the compounds whose chemical formula comprises at least two ethylenic bonds and which make it possible to connect two or more polymer chains during the radical polymerization reaction involving the constituent monomers of the poly(itaconate) as described above. The polyethylene crosslinking monomers (AR) can be added to the monomers before the initiation of the radical polymerization process making it possible to prepare the crosslinked poly(itaconate) (P).

[0045] The polyethylene crosslinking monomers (AR) can also be constituents of the monomeric compositions involved in the radical polymerization process, such as resulting from the esterification between two or more itaconic acid molecules with a molecule of a polyol.

[0046] For the purposes of the present invention, the term “polyol” means an aliphatic molecule substituted by at least two hydroxyl groups.

[0047] Depending on the case, the solution according to the invention may have one or more of the characteristics below: - Composition (C) comprises between 20% and 80% by mass, preferably between 40% and 60% by mass, even more preferably between 43% and 57% by mass of oil (Hl) and between 80% and 20% by mass, preferably between 60% and 40% by mass, even more preferably between 57% and 43% by mass of poly(itaconate) (P); - the oil (Hl) is an oil found in liquid form at a temperature between 4°C and 45°C, preferably between 15°C and 45°C and even more preferably at a temperature between 15°C and 35°C; - oil (Hl) is a mineral or vegetable oil or a mixture of these two types of oils; - the mass ratio (P) / (H1) is between 5 / 1 and 1 / 5, preferably between 4 / 1 and 1 / 4, more preferably between 3 / 1 and 1 / 3, even more preferably between 1 / 2 and 2 / 1.

[0048] The mineral oils are preferably chosen from: • paraffins, isoparaffins or cycloparaffins such as: mixtures of alkanes and isoalkanes and cycloalkanes marketed under the names Emogreen™ L15, Emogreen™ L19, Emosmart™ L15, Emosmart™ L19, Emosmart™ V21, Isopar™ L, Isopar™ H, Isopar™ G or Isopar™ M, • White mineral oils, such as those marketed under the following names: Marcol™ 52, Marcol™ 82, Drakeol™ 6VR, Eolane™ 130, Eolane™ 150, • Linear alkanes containing 11 to 19 carbon atoms, and more particularly n-undecane, n-dodecane, n-tridecane, and even more particularly the mixture of n-undecane and n-tridecane, • Branched alkanes, containing 7 to 20 carbon atoms such as: isododecane, isopentadecane, isohexadecane, isoheptadecane, isooctadecane, isononadecane or isoeicosane, or mixtures of some of them identified by their INCI name: C7-8 isoparaffin, C8-9 iso-paraffin, C9-11 isoparaffin, C9-12 isoparaffin, C9-13 isoparaffin, C9-14 isoparaffin, C9-16 isoparaffin, Cl0-11 isoparaffin, Cl0-12 isoparaffin, Cl0-13 isoparaffin, Cl 1-12 isoparaffin, Cl 1-13 isoparaffin, Cl 1-14 isoparaffin, C12-14 isoparaffin, C12-20 isoparaffin, C13-14 isoparaffin, C13-16 isoparaffin, • Cycloalkanes optionally substituted by one or more radicals linear or branched alkyls, • Hemisqualane (or 2,6,10-trimethyl-dodecane; CAS number: 3891-98-3), squalane (or 2,6,10,15,19,23-hexamethyltetracosane), hydrogenated polyisobutene or hydrogenated polydecene.

[0049] The vegetable oils are preferably chosen from oils belonging to the family: • lipophilic esters of formula (IV),

[0050] in which R'2-(C=O)- represents a saturated or unsaturated, linear or branched acyl radical containing from eight to twenty-four carbon atoms, and R'3 represents, independently of R'2, a saturated or unsaturated, linear or branched hydrocarbon chain containing from one to twenty-four carbon atoms, the compound of formula (IV) representing, for example, methyl laurate, ethyl laurate, propyl laurate, isopropyl laurate, butyl laurate, 2-butyl laurate, hexyl laurate, methyl cocoate, ethyl cocoate, propyl cocoate, isopropyl cocoate, butyl cocoate, 2-butyl cocoate, hexyl cocoate, octyl cocoate, decyl cocoate, cocoate octyl and decyl, methyl myristate, ethyl myristate, propyl myristate, isopropyl myristate, butyl myristate, 2-butyl myristate, hexyl myristate, octyl myristate, methyl palmitate,ethyl palmitate, propyl palmitate, isopropyl palmitate, butyl palmitate, 2-butyl palmitate, hexyl palmitate, octyl palmitate, methyl oleate, ethyl oleate, propyl oleate, isopropyl oleate, butyl oleate, 2-butyl oleate, hexyl oleate, octyl oleate, methyl stearate, ethyl stearate, propyl stearate, isopropyl stearate, butyl stearate, 2-butyl stearate, hexyl stearate, octyl stearate, methyl isostearate, ethyl isostearate, propyl isostearate, isopropyl isostearate, butyl isostearate, 2-butyl isostearate, hexyl isostearate, isostearyl isostearate. ,

[0051] According to a particular aspect, the compound of formula (IV) represents cocoyl caprylate caprate such as that sold under the brand name DUB 810C, propyl cocoate, isopropyl cocoate, propyl palmitate, isopropyl palmitate, octyl palmitate. • triglycerides of formula (V)

[0052] in which R4-(C=O), R5-(C=O) and R6-(C=O), identical or different, represent an acyl group, saturated or unsaturated, linear or branched, comprising from eight to twenty-four carbon atoms, and more particularly an acyl group chosen from the elements of the group consisting of the octanoyl, decanoyl, dodecanoyl, tetradecanoyl, hexadecanoyl, octadecanoyl, eicosanoyl, docosanoyl, oleyl, linoleyl, linolenoyl or isostearyl groups.

[0053] By oil (H2) is meant the oils (H1) as defined above, and more particularly the mineral oils as described above and the compounds of formula (V) for which R4-(C=O), R5-(C=O) and R6-(C=O), identical or different, represent an acyl group chosen from the elements of the group consisting of the octanoyl, decanoyl and dodecanoyl groups.

[0054] The present invention also relates to a formulation for topical use (F) comprising a composition (C) as defined above. In other words, the formulation for topical use (F) comprises the mixture of the composition (C) and at least one oil (H2).

[0055] The expression "for topical use" used in the definition of formulation (F) as defined above, means that said formulation is prepared to allow its application to the skin, hair, scalp or mucous membranes, whether it is a direct application in the case of a cosmetic, dermocosmetic, dermopharmaceutical or pharmaceutical composition or an indirect application for example in the case of a personal hygiene product in the form of a textile or paper wipe or sanitary products intended to be in contact with the skin or mucous membranes.

[0056] Preferably, this formulation for topical use (F) will be a cosmetic formulation.

[0057] Said formulation for topical use (F) is generally in the form of an oily composition, in the form of a suspension, an emulsion, a microemulsion or a nanoemulsion, whether they are of the water-in-oil, oil-in-water, water-in-oil-in-water or oil-in-water-in-oil type.

[0058] Said formulation for topical use (F) may be packaged in a bottle, in a pump-type "bottle" device, in pressurized form in an aerosol device, in a device provided with an openwork wall such as a grid or in a device provided with a ball applicator (called "roll-on").

[0059] Generally, said composition for topical use (F) also comprises excipients and / or active ingredients usually used in the field of formulations for topical use, in particular cosmetic, dermocosmetic, pharmaceutical or dermopharmaceutical formulations, such as thickening and / or gelling surfactants, stabilizers, film-forming compounds, hydrotropic agents, plasticizing agents, emulsifying and co-emulsifying agents, opacifying agents, pearlescent agents, superfatting agents, sequestering agents, chelating agents, antioxidants, perfumes, preservatives, conditioning agents, whitening agents intended for bleaching hair and skin, active ingredients intended to provide a treatment action with respect to the skin or hair, sunscreens, mineral fillers or pigments, particles providing a visual effect or intended for the encapsulation of active ingredients,exfoliating particles, texture agents. ,

[0060] The mixture of composition (C) as described above and an oil (H2) will preferably be carried out at a temperature between 50°C and 85°C, more preferably at a temperature of 80°C. The homogeneous oily composition obtained is then cooled to room temperature, between 15°C and 30°C.

[0061] The thickening of the oil (H2) is finally assessed visually by qualifying the consistencies as liquid, viscous or gelled, by measuring a dynamic viscosity value.

[0062] For a composition (C) to be considered effective, the viscous or gelled aspects must at least be achieved.

[0063] The present invention also relates to a process for preparing a thickening composition (C) according to the invention, comprising the following steps: a. Production of a composition (C0) of mono- and / or oligoesters of itaconic acid comprising a compound of formula (II) and the compound of formula (I) in free acid form or partially or totally salified, b. Preparation of a mixture (Ml) of the composition (C0) produced in step a) with an oil (Hl), c. Polymerization of the mixture (Ml) initiated by introducing a thermal radical initiator into said mixture (Ml) obtained at the end of step b), and d. Recovery of composition (C).

[0064] By thermal initiator is meant in step c) of the process as defined above, a molecule which, placed at a temperature specific to said structure, generates the production of at least two radicals by homolysis of at least one covalent bond, said radicals making it possible to initiate radical polymerization.

[0065] According to a particular aspect, the thermal initiator is chosen from the elements of the group consisting of lauroyl peroxide, azo bis(isobutyronitrile) or AIBN, benzoyl peroxide or BPO, azo bis(2-methyl butyronitryl) or AMBN, 4,4'-azo bis(4-cyanovaleric acid) or ACVA, 2,2'-Azobis(2,4-dimethylvaleronitrile, cumene hydroperoxide, di-tert-butyl peroxide or tert-butyl hydroperoxide

[0066] The process for preparing the thickening composition (C) will preferably comprise one or more of the following characteristics: - The method comprises a step of removing at least part of the oil (Hl) included in the composition (C). This makes it possible to obtain more concentrated compositions (C), - polymerization is carried out at a temperature between 40°C and 80°C - in step b) a crosslinking monomer (AR) is added. - the crosslinking monomer is a diethylenic or polyethylene crosslinking monomer chosen in particular from ethylene glycol dimethacrylate, diethylene glycol diacrylate, ethylene glycol diacrylate, diallyl urea, triallylamine, trimethylol propanetriacrylate, methylene-bis(acrylamide). - step a) of producing a composition (CO) of mono- and / or oligoesters of itaconic acid comprises the following sub-steps: i. Introduction into a reactor of a bio-sourced alcohol or polyol selected from the elements of the group consisting of compounds in liquid form: • oligoglycerols with the following structure:

[0067] With m representing an integer greater than or equal to 2 and less than or equal to 10, • natural polyols with the following structure:

[0068] (H'b) HO^ X OH vag OH

[0069] With o representing a number equal to 2 (erythritol), or equal to 3 (xylitol), or equal to 4 (sorbitol), • dehydrated natural polyols with the following structure:

[0070] With X representing a hydrogen atom (erythritan), or the radical -CH2-OH (xylitan) or the radical -CH(OH)-CH2-OH (sorbitan), • aliphatic fatty alcohols of the following structure:

[0071] With RI representing a linear or branched, saturated or unsaturated aliphatic hydrocarbon radical, comprising from 6 to 36 carbon atoms and optionally substituted with one or more hydroxyl groups.

[0072] According to a particular aspect, RI represents an aliphatic hydrocarbon radical chosen from the n-hexyl, n-heptyl, n-octyl, n-decyl, n-dodecyl, n-tetradecyl, n-hexadecyl, n-octadecyl, oleyl, linoleyl, lino-lenilic, arachidyl, behenyl, erucyl or 12-hydroxystearyl radicals. • the a,co-diols of the following formula (H'e):

[0073] With q representing an integer greater than or equal to 1 and less than or equal to 12, • compounds of the following formula (H'f):

[0074] with R' 1 representing a linear or branched, saturated or unsaturated aliphatic hydrocarbon radical, comprising from 6 to 36 carbon atoms and optionally substituted with one or more hydroxyl groups.

[0075] According to a particular aspect, R' 1 represents an aliphatic hydrocarbon radical chosen from the n-hexyl, n-heptyl, n-octyl, n-decyl, n-dodecyl, n-tetradecyl, n-hexadecyl, n-octadecyl, oleyl, linoleyl, lino-lenilic, arachidyl, behenyl, erucyl or 12-hydroxystearyl radicals.

[0076] More particularly, the compound of formula (H'f) is batyl alcohol whose structure is as follows:

[0077]

[0078] OH (II'fA) • the compounds of formula (II'g) following: with R' 1-C(=O) representing a linear or branched, saturated or unsaturated hydrocarbon acyl radical containing from 12 to 24 carbon atoms, and more particularly a radical chosen from the elements of the group consisting of the dodecanoyl, tetradecanoyl, hexadecanoyl, octadecanoyl, eicosanoyl, docosanoyl, oleyl, linoleyl, linolenoyl or isostearyl radicals, and with x representing a natural whole number greater than or equal to 1 and less than or equal to 5. More particularly the compound of formula (II'g) is glycerol monostearate of the following formula; OH

[0079] O (II'gA) More particularly, the compound of formula (II'g) is polyglyceryl-6 laurate whose structure is as follows:

[0080] (II'gB), i. Addition to the reactor, placed under mechanical stirring, of itaconic acid (I), a polymerization inhibitor and then an esterification catalyst, ii. Maintenance of the medium present in the reactor at a temperature between 120°C and 180°C, under partial pressure, to carry out an esterification reaction, and iii. Recovery of a composition of mono- and / or oligoesters of itaconic acid. For the purposes of the present invention, the term “polymerization inhibitor” means compounds which, when added to monomers, regulate or rapidly stop the unwanted initiation of polymerization of said monomers; among these polymerization inhibitors, mention may be made of quinones, hydroquinone, methyl hydroquinone, 1,4-Benzoquinone, 2-tert-Butyl-1,4-benzoquinone, catechols such as, for example, 4-tert-Butylpyrocatechol-2,6-Di-tert-butylphenol, 6-tert-Butyl-2,4-xylenol, tert-Butylhydroquinone, 4-methoxyphenol, 2,6-Di-tert-butyl-p-cresol, aromatic nitro compounds such as nitrobenzenes, nitrophenols, nitrocresols, nitroso compounds, phenothiazine, 1,1-Diphenyl-2-picrylhydrazyl, and metal salts such as copper salts, such as copper (II) dibutyldithiocarbamate. - sub-steps i) to iii) are carried out at a temperature between 120 and 180°C, - sub-step iii) is carried out at a pressure of between 500 and 20 mbar and, more particularly, between 500 and 200 mbar, - sub-step iii) has a duration of between 30 minutes and 10 hours. - In sub-step ii) the polymerization inhibitor is chosen from 1,4-Benzoquinone, 2-tert-Butyl-l,4-benzoquinone, Phenothiazine, 6-tert-Butyl-2,4-xylenol, Copper(II) Dibutyldithiocarbamate, 1,1-Diphenyl-2-picrylhydrazyl, 2,6-Di-tert-butyl-p-cresol, 4-tert-Butylpyrocatechol-2,6-Di-tert-butylphenol, Hydroquinone, tert-Butylhydroquinone and 4-methoxyphenol. - In sub-step ii) the esterification catalyst is an acid chosen from sulfuric, hydrochloric, phosphoric, nitric, hypophosphorous, methanesulfonic, para-toluenesulfonic, trifluoromethanesulfonic acids and acidic ion exchange resins.

[0081] Note that when a fatty alcohol of formula (IId) is used, a composition (Alld) is then obtained containing a monoester of formula (Alldl) and / or a diester of formula (AIId2). (Alldl) O .jj< -'-'X ^r5 □ (Alldl') (AIId2)

[0082] Similarly, when an aco-diol of formula (IIe) is used, a composition (Aile) is then obtained containing a monoester of formula (Ilel) and / or diesters of formulas (Ilel') or (IIe2) comprising a single ethylenic bond and / or a diester of formula (IIe3) comprising two ethylenic bonds and / or a tetraester of formula (IIe4) comprising three ethylenic bonds. O (Hel) (IIe3) (He3') (IIe4)

[0083] The molar stoichiometric ratio (II'a) / (I) is greater than or equal to 0.25 and less than or equal to 2.0.

[0084] The molar stoichiometric ratio (Il'b) / (I) is greater than or equal to 0.25 and less than or equal to 2.0.

[0085] The molar stoichiometric ratio (II'c) / (I) is greater than or equal to 0.25 and less than or equal to 2.0.

[0086] The molar stoichiometric ratio (Il'd) / (I) is greater than or equal to 0.25 and less than or equal to 2.0.

[0087] The molar stoichiometric ratio (Il'e) / (I) is greater than or equal to 0.25 and less than or equal to 2.0.

[0088] The molar stoichiometric ratio (Il'f) / (I) is greater than or equal to 0.25 and less than or equal to 2.0.

[0089] The molar stoichiometric ratio (Il'g) / (I) is greater than or equal to 0.25 and less than or equal to 2.0.

[0090] The compositions of mono- or oligoesters of itaconic acid (A) are characterized by measurements of macroscopic indices (acid and ester indices) and by their residual itaconic acid content measured by High Performance Liquid Chromatography (HPLC) coupled to an Ultra-Violet (UV) detector with internal calibration.

[0091] Finally, a conversion rate of itaconic acid is determined. A conversion rate greater than or equal to 75% must be achieved to consider the proper progress of the esterification reactions.

[0092] As examples of foaming and / or detergent surfactants which can be associated with said thickening composition (C) as defined previously in said composition (F), there are anionic, cationic, amphoteric or non-ionic foaming and / or detergent surfactants.

[0093] Among the foaming and / or detergent anionic surfactants which can be associated with said thickening composition (C) as defined previously in said composition (F), there are the salts of alkali metals, alkaline earth metals, ammonium, amines, or amino alcohols of alkyl ether sulfates, alkyl sulfates, alkylamido ether sulfates, alkylaryl polyether sulfates, monoglyceride sulfates, alpha-olefin sulfonates, paraffin sulfonates, alkyl phosphates, alkyl ether phosphates, alkyl sulfonates, alkylamide sulfonates, alkylaryl sulfonates, alkyl carboxylates, alkyl sulfosuccinates, alkyl ether sulfosuccinates, alkylamide sulfosuccinates, alkyl sulfoacetates, alkyl sarcosinates, acyl isethionates, N-acyl taurates, acyl lactylates, N-acyl derivatives of amino acids, N-acyl derivatives of peptides, N-acyl derivatives of proteins, N-acyl derivatives of fatty acids.

[0094] Among the foaming and / or detergent amphoteric surfactants which can be associated with said thickening composition (C) as defined previously in said composition (F), there are alkylbetaines, alkylamidobetaines, sultaines, alkylami-doalkylsulfobetaines, imidazoline derivatives, phosphobetaines, amphopolyacetates and amphopropionates.

[0095] Among the foaming and / or detergent cationic surfactants which can be associated with said thickening composition (C) as defined previously in said composition (F), there are particularly quaternary ammonium derivatives.

[0096] Among the foaming and / or detergent non-ionic surfactants which can be associated with said thickening composition (C) as defined previously in said composition (F), there are more particularly alkylpolyglycosides comprising a linear or branched, saturated or unsaturated aliphatic radical, and comprising from 8 to 16 carbon atoms, such as octyl polyglucoside, decyl polyglucoside, undecylenyl polyglucoside, dodecyl polyglucoside, tetradecyl polyglucoside, hexadecyl polyglucoside, 1-12 dodecanediyl polyglucoside; ethoxylated hydrogenated castor oil derivatives such as the product marketed under the INCI name “Peg-40 hydrogenated castor oil”; polysorbates such as Polysorbate 20, Polysorbate 40, Polysorbate 60, Polysorbate 70, Polysorbate 80, Polysorbate 85; coconut amides; N-alkylamines.

[0097] As examples of thickening and / or gelling surfactants which can be combined with said thickening composition (C) as defined previously in said composition (F), there are optionally alkoxylated alkylpolyglycoside fatty esters, such as ethoxylated methylpolyglucoside esters such as PEG 120 methyl glucose trioleate and PEG 120 methyl glucose dioleate marketed respectively under the names GLUCAMATE™ LT and GLUMATE™ DOE120; alkoxylated fatty esters such as PEG 150 pentaerythritol tetrastearate marketed under the name CROTHIX™ DS53, PEG 55 propylene glycol oleate marketed under the name ANTIL™ 141; fatty chain polyalkylene glycol carbamates such as PPG-14 laureth isophoryl dicarbamate marketed under the name ELFACOS™ T211, PPG-14 palmeth-60 hexyl dicarbamate marketed under the name ELFACOS™ GT2125.

[0098] As examples of thickening and / or gelling agents which can be associated with said thickening composition (C) as defined previously in said composition (F), there are polysaccharides consisting solely of oses, such as glucans or homopolymers of glucose, glucomannoglucans, xyloglycans, galactomannans whose degree of substitution (DS) of the D-galactose units on the main D-mannose chain is between 0 and 1, and more particularly between 1 and 0.25, such as galactomannans originating from cassia gum (DS = 1 / 5), locust bean gum (DS = 1 / 4), tara gum (DS = 1 / 3), guar gum (DS = 1 / 2), fenugreek gum (DS = 1).

[0099] As examples of thickening and / or gelling agents which can be associated with said thickening composition (C) as defined previously in said composition (F), there are polysaccharides consisting of ose derivatives, such as sulfated gal-lactans and more particularly carrageenans and agar, uronans and more particularly algins, alginates and pectins, heteropolymers of oses and uronic acids and more particularly xanthan gum, gellan gum, exudates of gum arabic and karaya gum, glucosaminoglycans.

[0100] As examples of thickening and / or gelling agents which can be associated with said thickening composition (C) as defined previously in said composition (F), there are cellulose, cellulose derivatives such as methyl cellulose, ethyl cellulose, hydroxypropyl cellulose, silicates, starch, hydrophilic starch derivatives, polyurethanes.

[0101] As examples of stabilizing agents which can be associated with said thickening composition (C) as defined previously in said composition (F), there are microcrystalline waxes, and more particularly ozokerite, mineral salts such as sodium chloride or magnesium chloride, silicone polymers such as polysiloxane polyalkyl polyether copolymers.

[0102] As examples of solvents which can be associated with said thickening composition (C) as defined previously in said composition (F), there are water, organic solvents such as glycerol, diglycerol, glycerol oligomers, ethylene glycol, propylene glycol, butylene glycol, 1,3-propanediol, 1,2-propanediol, hexylene glycol, diethylene glycol, xylitol, erythritol, sorbitol, water-soluble alcohols such as ethanol, isopropanol or butanol, mixtures of water and said organic solvents.

[0103] As examples of thermal or mineral waters which can be associated with said thickening composition (C) as defined previously in said composition (F), there are thermal or mineral waters having a mineralization of at least 300 mg / l, in particular Avène water, Vittel water, Vichy basin water, Uriage water, Roche Posay water, Bourboule water, Enghien-les-bains water, Saint-Gervais-les-bains water, Néris-les-bains water, Allevard-les-bains water, Digne water, Maizieres water, Neyrac-les-bains water, Lons le Saunier water, Rochefort water, Saint Christau water, Fumades water and Tercis-les-bains.

[0104] As examples of hydrotropic agents which can be associated with said thickening composition (C) as defined previously in said composition (F), there are xylenes sulfonates, cumenes sulfonates, hexylpolyglucoside, 2-ethylhexylpolyglucoside, n-heptylpolyglucoside.

[0105] As examples of emulsifying surfactants which can be associated with said thickening composition (C) as defined previously in said composition (F), there are non-ionic surfactants, anionic surfactants, cationic surfactants.

[0106] As examples of emulsifying non-ionic surfactants which can be combined with said thickening composition (C) as defined previously in said composition (F), there are fatty acid esters of sorbitol, such as the products marketed under the names MONTANE™40, MONTANE™60, MONTANE™70, MONTANE™80 and MONTANE™85; compositions comprising glycerol stearate and ethoxylated stearic acid between 5 moles and 150 moles of ethylene oxide, such as the composition comprising ethoxylated stearic acid with 135 moles of ethylene oxide and glycerol stearate marketed under the name SIMULSOL™ 165; mannitan esters; ethoxylated mannitan esters; sucrose esters; methylglucoside esters;alkylpolyglycosides comprising a linear or branched, saturated or unsaturated aliphatic radical, and comprising from 14 to 36 carbon atoms, such as tetradecyl polyglucoside, hexadecyl polyglucoside, octadecyl polyglucoside, hexadecyl polyxyloside, octadecyl polyxyloside, eicosyl polyglucoside, dodecosyl polyglucoside, 2-octyldodecyl polyxyloside, 12-hydroxystearyl polyglucoside; compositions of linear or branched, saturated or unsaturated fatty alcohols, and comprising from 14 to 36 carbon atoms, and of alkylpolyglycosides as described above, for example the compositions marketed under the names MONTANOV™68, MONTANOV™14, MONTANOV™82, MONTANOV™202, MONTANOV™S, MONTANOV™W018, MONTANOV™L, FLUIDANOV™20X and EASYNOV™.;

[0107] As examples of anionic surfactants which can be associated with said thickening composition (C) as defined previously in said composition (F), There are glyceryl stearate citrate, cetearyl sulfate, soaps such as sodium stearate or triethanolammonium stearate, N-acylated derivatives of salified amino acids, for example stearoyl glutamate.

[0108] As examples of emulsifying cationic surfactants which can be associated with said thickening composition (C) as defined previously in said composition (F), there are amine oxides, quaternium-82 and the surfactants described in patent application WO96 / 00719 and mainly those whose fatty chain comprises at least 16 carbon atoms.

[0109] As examples of opacifying and / or pearlescent agents which can be associated with said thickening composition (C) as defined previously in said composition (F), there are sodium palmitate, sodium stearate, sodium hydroxystearate, magnesium palmitate, magnesium stearate, magnesium hydroxystearate, ethylene glycol monostearate, ethylene glycol distearate, polyethylene glycol monostearate, polyethylene glycol distearate, fatty alcohols comprising from 12 to 22 carbon atoms.

[0110] As examples of texturizing agents that can be associated with said thickening composition (C) as defined previously in said composition (F), there are N-acylated derivatives of amino acids, such as lauroyl lysine marketed under the name AMINOHOPE™LL, octenyl starch succinate marketed under the name DRYFLO™, myristyl polyglucoside marketed under the name MONTANOV™ 14, cellulose fibers, cotton fibers, chitosan fibers, talc, sericite, mica

[0111] As examples of deodorant agents which can be associated with said thickening composition (C) as defined previously in said composition (F), there are alkali silicates, zinc salts such as zinc sulfate, zinc gluconate, zinc chloride, zinc lactate; quaternary ammonium salts such as cetyltrimethylammonium salts, cetylpyridinium salts; glycerol derivatives such as glycerol caprate, glycerol caprylate, polyglycerol caprate; 1,2 decanediol; 1,3 propanediol; salicylic acid; sodium bicarbonate; cyclodextrins; metal zeolites; TRICLOSAN™;aluminum bromohydrate, aluminum chlorohydrates, aluminum chloride, aluminum sulfate, aluminum zirconium chlorohydrates, aluminum zirconium trichlorohydrate, aluminum zirconium tetrachlorohydrate, aluminum zirconium pentachlorohydrate, aluminum zirconium octochlorohydrate, aluminum sulfate, sodium aluminum lactate, aluminum glycol chlorohydrate complexes, such as aluminum propylene glycol chlorohydrate complex, aluminum propylene glycol dichlorohydrate complex, aluminum propylene sesquichlorohydrate complex; glycol, aluminum chlorohydrate polyethylene glycol complex, aluminum dichlorohydrate polyethylene glycol complex, aluminum sesquichlorohydrate polyethylene glycol complex.

[0112] As examples of waxes that can be combined with said thickening composition (C) as defined previously in said composition (F), there are beeswax, carnauba wax, candelilla wax, ouricoury wax, Japan wax, cork fiber wax, sugar cane wax, paraffin waxes, lignite waxes, microcrystalline waxes, lanolin wax; ozokerite; polyethylene wax; silicone waxes; vegetable waxes; fatty alcohols and fatty acids that are solid at room temperature; glycerides that are solid at room temperature. By "waxes" is meant in the present application the compounds and / or mixtures of compounds that are insoluble in water, having a solid form at a temperature greater than or equal to 45°C.

[0113] As examples of active ingredients that can be associated with said thickening composition (C) as defined previously in said composition (F), there are vitamins and their derivatives, in particular their esters, such as retinol (vitamin A) and its esters (retinyl palmitate for example), ascorbic acid (vitamin C) and its esters, sugar derivatives of ascorbic acid (such as ascorbyl glucoside), tocopherol (vitamin E) and its esters (such as tocopherol acetate), vitamins B3 or B10 (niacinamide and its derivatives); compounds showing a skin lightening or depigmenting action such as co-undecelynoyl phenylalanine marketed under the name SEPIWHITE™MSH, SEPICALM™VG, the monoester and / or diester of glycerol of co-undecelynoyl phenylalanine, co-undecelynoyl dipeptides, arbutin, kojic acid, hydroquinone; compounds showing a soothing action including SEPICALM™ S, allantoin and bisabolol;anti-inflammatory agents; compounds showing a moisturizing action such as urea, hydroxyureas, glycerol, polyglycerols, glycerolglucoside, diglycerolglucoside, polyglycerylglucosides, xylitylplucoside; plant extracts rich in polyphenols such as grape extracts, pine extracts, wine extracts, olive extracts; compounds showing a slimming or lipolytic action such as caffeine or its derivatives, ADIPOSLIM™, ADIPOLESS™, fucoxanthin; N-acylated proteins; N-acylated peptides such as MATRIXIL™; N-acylated amino acids; N-acylated partial protein hydrolysates; amino acids; peptides; total protein hydrolysates; soy extracts, for example Raffermine™; wheat extracts for example TENSINE™ or GLIADINE™;plant extracts, such as tannin-rich plant extracts, isoflavone-rich plant extracts or terpene-rich plant extracts; freshwater or marine algae extracts; marine plant extracts; marine extracts in general; such as corals; essential waxes; bacterial extracts; ceramides; phospholipids; compounds showing antimicrobial action or purifying action, such as LIPACIDE™ C8G, LIPACIDE™ UG, SEPICONTROL™ A5; OCTOPIROX™ or SENSIVA™ SC50; compounds showing energizing or stimulating property such as PHYSIOGENYL™, panthenol and its derivatives such as SEPICAP™ MP; anti-aging active ingredients such as SEPILIFT™ DPHP, LIPACIDE™ PVB, SEPIVINOL™, SEPIVITAL™, MANOLIVA™, PHYTO-AGE™, TIMECODE™; SURVICODE™; anti-photoaging active ingredients; active ingredients that protect the integrity of the dermo-epidermal junction; active ingredients that increase the synthesis of components of the extracellular matrix such as collagen, elastins, glycosaminoglycans; active ingredients that act favorably on chemical cellular communication such as cytokines or physical ones such as integrins;active ingredients creating a sensation of "heating" on the skin such as activators of skin microcirculation (such as nicotinic acid derivatives) or products creating a sensation of "coolness" on the skin (such as menthol and derivatives); active ingredients improving skin microcirculation, for example vein tonics; draining active ingredients; active ingredients with a decongestant purpose such as extracts of ginko biloba, ivy, horse chestnut, bamboo, ruscus, butcher's broom, centalla asiatica, fucus, rosemary, willow;skin tanning or browning agents, for example dihydroxyacetone (DHA), erythrulose, mesotartaric aldehyde, glutaraldehyde, glyceraldehyde, alloxan, ninhydrin, plant extracts for example extracts of red woods of the genus Pterocarpus and of the genus Baphia such as Pteropcarpus santalinus, Pterocarpus osun, Pterocarpus soyauxii, Pterocarpus erinaceus, Pterocarpus indicus or Baphia nitida such as those described in European patent application EP 0 971 683;agents known for their action of facilitating and / or accelerating the tanning and / or browning of human skin, and / or for their action of coloring human skin, for example carotenoids (and more particularly beta carotene and gamma carotene), the product marketed under the brand name “Carrot oil” (INCI name: Daucus Carota, helianthus annuus Sunflower oil) by the company Provital, which contains carotenoids, vitamin E and vitamin K;tyrosine and / or its derivatives, known for their effect on accelerating the tanning of human skin in association with exposure to ultraviolet radiation, for example the product marketed under the brand name “SunTan Accelerator™” by the company Provital which contains tyrosine and riboflavins (vitamin B), the tyrosine and tyrosinase complex marketed under the brand name “Zymo Tan Complex” by the company Zymo Line, the product marketed under the brand name Mela-noBronze™ (INCI name: Acetyl Tyrosine, Monk's pepper extract (Vitex Agnus- ; castus)) by the company Mibelle which contains acetyl tyrosine, product marketed under the brand name Unipertan VEG-24 / 242 / 2002 (INCI name: butylene glycol and Acetyl Tyrosine and hydrolyzed vegetable protein and Adenosine triphosphate) by the company UNIPEX, the product marketed under the brand name “Try-Excell™” (INCI name: Oleoyl Tyrosine and Luffa Cylindrica (Seed) Oil and Oleic acid) by the company Sederma which contains pumpkin seed extracts (or Loofah oil), the product marketed under the brand name “Actibronze™” (INCI name: hydrolyzed wheat protein and acetyl tyrosine and copper gluconate) by the company Alban Muller, the product marketed under the brand name Tyrostan™ (INCI name: potassium caproyl tyrosine) by the company Synerga, the product marketed under the brand name Tyrosinol (INCI name: Sorbitan Isostearate, glyceryl oleate, caproyl Tyrosine) by the company Synerga,the product marketed under the brand name In-staBronze™ (INCI name: Dihydroxyacetone and acetyl tyrosine and copper gluconate) marketed by the company Alban Muller, the product marketed under the brand name Tyrosilane (INCI name: methylsilanol and acetyl tyrosine) by the company Exymol; peptides known for their melanogenesis-activating effect, for example the product marketed under the brand name Bronzing SF Peptide powder (INCI name: Dextran and Octapeptide-5) by the company Infinitec Activos, the product marketed under the brand name Melitane (INCI name: Glycerin and Aqua and Dextran and Acetyl hexapeptide-1) comprising acetyl hexapeptide-1 known for its alpha-MSH agonist action, the product marketed under the brand name Melatimes Solutions™ (INCI name: Butylene glycol, Palmitoyl Tripeptide-40) by the company LIPOTEC,sugars and sugar derivatives, for example the product marketed under the brand name Tanositol™ (INCI name: inositol) by the company Provital, the product marketed under the brand name Thalitan™ (or Phyco-saccharide™ AG) by the company CODIF international (INCI name: Aqua and Hydrolyzed algin (Laminaria Digitata) and magnesium sulfate and manganese sulfate) containing an oligosaccharide of marine origin (guluronic acid and man-nuronic acid chelated with magnesium and manganese ions), the product marketed under the brand name Melactiva™ (INCI name: Maltodextrin, Mucuna Pruriens Seed extract) by the company Alban Muller, compounds rich in flavonoids, for example the product marketed under the brand name “Biotanning” (INCI name: Hydrolyzed citrus Aurantium dulcis fruit extract) by the company Silab and known to be rich in lemon flavonoids (of the type hesperidins); agents intended for the treatment of hair and / or body hair,for example, agents for protecting hair follicle melanocytes, intended to protect said melanocytes against cytotoxic agents responsible for the senescence and / or apoptosis of said melanocytes, such as agents mimetic of the activity of DOPAchrome tautomerase chosen from those, described in the European patent application published under number EP1515688 A2, synthetic molecules mimetic of SOD for example manganese complexes, antioxidant compounds for example cyclodextrin derivatives, siliceous compounds derived from ascorbic acid, pyrrolidone carboxylate of lysine or arginine, combinations of mono- and diester of cinnamic acid and vitamin C, and more generally those cited in the European patent application published under number EP 1 515 688 A2.

[0114] As examples of antioxidant agents which can be associated with said thickening composition (C) as defined previously in said composition (F), there are EDTA and its salts, citric acid, tartaric acid, oxalic acid, BHA (butylhydroxyanisol), BHT (butylhydroxytoluene), tocopherol derivatives such as tocopherol acetate, mixtures of antioxidant compounds such as DISSOLVINE GL 47S marketed by the company Akzo Nobel under the INCI name: Tetrasodium Glutamate Diacetate.

[0115] As examples of sunscreens which can be associated with said thickening composition (C) as defined previously in said composition (F), there are all those appearing in the cosmetic directive 76 / 768 / EEC amended annex VII.

[0116] Among the organic sunscreens that can be associated with said thickening composition (C) as defined previously in said composition (F), there is the family of benzoic acid derivatives such as para-aminobenzoic acids (PABA), in particular PABA monoglycerol esters, N,N25 propoxy PABA ethyl esters, N,N-diethoxy PABA ethyl esters, N,N-dimethyl PABA ethyl esters, N,N-dimethyl PABA methyl esters, N,N-dimethyl PABA butyl esters; the family of anthranilic acid derivatives such as homomenthyl-N-acetyl anthranilate; the family of salicylic acid derivatives such as amyl salicylate, homomenthyl salicylate, ethylhexyl salicylate, phenyl salicylate, benzyl salicylate, p-isopropanolphenyl salicylate;the family of cinnamic acid derivatives such as ethylhexyl cinnamate, ethyl-4-isopropyl cinnamate, methyl-2,5-diisopropyl cinnamate, p-methoxypropyl cinnamate, p-methoxyisopropyl cinnamate, p-methoxyisoamyl cinnamate, p-methoxyoctyl cinnamate (p-methoxy 2-ethylhexyl cinnamate), p-methoxy 2-ethoxyethyl cinnamate, p-methoxycyclohexyl cinnamate, ethyl-a-cyano-[3-phenyl] cinnamate, 2-ethylhexyl-a-cyano-[3-phenyl] cinnamate, glyceryl diparamethoxy mono-2-ethylhexanoyl cinnamate; the family of benzophenone derivatives such as 2,4-dihydroxybenzophenone, 2,2'-dihydroxy-4-methoxybenzophenone, 2,2',4,4'-tetrahydroxybenzophenone, 2-hydroxy-4-methoxybenzophenone, ; 2-hydroxy-4-methoxy-4'-methylbenzophenone, 2-hydroxy-4-methoxybenzophenone-5-sulfonate, 4-phenylbenzophenone, 2-ethylhexyl-4'-phenylbenzophenone-2-5 carboxylate, 2-hydroxy-4-n-octyloxybenzophenone, 4-hydroxy-3-carboxybenzophenone; 3-(4'-methylbenzylidene)-d,l-camphor, 3 (benzylidene)-d,lcamphor, benzalkonium methosulfate camphor; urocanic acid, ethyl urocanate; the family of sulfonic acid derivatives such as 2-phenylbenzimidazole-5 sulfonic acid and its salts;the family of triazine derivatives such as hydroxyphenyl triazine, ethylhexyloxyhydroxyphenyl-4-methoxyphenyltriazine, 2,4,6-trianillino-(p-carbo-2'-ethylhexyl-r-oxy)-l,3,5-triazine, 4,4-((6-(((1,1-dimethylethyl)amino)carbonyl)phenyl)amino)-l,3,5-triazine-2,4-diyl diimino) bis-(2-ethylhexyl) benzoic acid ester, 2-phenyl-5-methylbenzoxazole, 2,2'-hydroxy-5-methylphenylbenzotriazole, 2-(2'-hydroxy-5'-t-octylphenyl)benzotriazole, 2-(2'-hydroxy-5'-methylphenyl)benzotriazole; dibenzazine; dianisoylmethane, 4-methoxy-4"-tbutylbenzoylmethane; 5-(3,3-dimethyl-2-norbornylidene)-3-pentan-2-one; the family of diphenylacrylate derivatives such as 2-ethylhexyl-2-cyano-3,3-diphenyl-2-propenoate, ethyl-2-cyano-3,3-diphenyl-2-propenoate; the family of polysiloxanes such as benzylidene siloxane malonate. ;

[0117] Among the inorganic sunscreens, also called "mineral screens", which can be associated with said thickening composition (C) as defined previously in said composition (F), there are titanium oxides, zinc oxides, cerium oxide, zirconium oxide, yellow, red or black iron oxides, chromium oxides. These mineral screens can be micronized or not, have undergone surface treatments or not and can optionally be presented in the form of aqueous or oily predispersions.

[0118] The invention will now be described in more detail with the aid of the examples below. Examples according to the invention:

[0119] El - Preparation of compositions of mono- and / or oligoesters of itaconic acid (A) according to the invention:

[0120] Ell- Preparation of the composition of glycerol monostearate itaconates (Allg):

[0121] In a reactor at 135°C and with mechanical stirring, 108.5 g (1 molar equivalent) of glycerol monostearate (II'gA), 39.6 g (1 molar equivalent) of itaconic acid (I) and 1000 ppm ( / reaction medium) of 4-methoxyphenol (or MEHQ) are introduced. 0.5% ( / reaction medium) of a 50% aqueous solution of H3PO2 is then added and the reaction medium is placed under controlled vacuum at approximately 500 mbar. The esterification reaction begins (distillation of the water formed) and is continued for a period of 6 hours. After these 6 hours, 125.7 g of glycerol monostearate itaconates (Allg) composition are isolated and characterized as such without any additional steps.

[0122] E.1.2- Preparation of the composition of batyl alcohol itaconates (Allf):

[0123] The same procedure as that described in paragraph Ell- was implemented by replacing the 108.5 g (1 molar equivalent) of glycerol monostearate (II'gA) and 39.6 g (1 molar equivalent) of itaconic acid (I) with 50.3 g (1 molar equivalent) of batyl alcohol (Il'f) and 19.2 g (1 molar equivalent) of itaconic acid (I). 61.2 g of batyl alcohol itaconate composition (Allf) are isolated and characterized.

[0124] E.1.3- Preparation of the stearic alcohol itaconate composition (AIIdl7):

[0125] The same procedure as that described in paragraph Ell- was carried out by replacing the 108.5 g (1 molar equivalent) of glycerol monostearate (II'gA) and 39.6 g (1 molar equivalent) of itaconic acid (I) with 74.0 g (1 molar equivalent) of stearyl alcohol (II'dl7) and 35.9 g (1 molar equivalent) of itaconic acid (I). 100.3 g of stearyl alcohol itaconate composition (AIIdl7) are isolated and characterized.

[0126] E.L4- Preparation of the composition of laurate itaconates of polyglycerol-6 (Allah):

[0127] The same procedure as that described in paragraph Ell- was carried out by replacing the 108.5 g (1 molar equivalent) of glycerol monostearate (II'g) and 39.6 g (1 molar equivalent) of itaconic acid (I) with 160.1 g (1 molar equivalent) of polyglycerol-6 laurate (II'gB) and 32.3 g (1 molar equivalent) of itaconic acid (I). 102.4 g of polyglyceryl-6 laurate itaconate composition (AIHi) are isolated and characterized.

[0128] E.L5- Results and conclusions:

[0129] The analytical characteristics of all the compositions (A) prepared are collated in Table 1 below.

[0130] [Tables 1] Reference Compositio n(A) (II') (eq.mol / (D) Acid Number (mg KOH / g) ESTER Index (mg KOH / g) (Residual D (%>' Conversion (D (%)b) 5211 JG (II'a; m = 2) (0.33) Not measured Not measured 11.1 86.4 5212 JG (II'a; m = 2) (0.25) 345.1 347.8 21.1 76.6 5298 JG (II'a; m = 6) (0.5) 156.1 161.0 Not measured Not measured 5375 JG (Il'b; o = 2) (0.5) Not measured Not measured 12.0 84.8 5358 JG (Il'b; o = 3) (0.5) 285.2 315.8 14.6 79.9 5350 JG (II'b ; o = 4) (0.5) 265.3 295.6 12.5 82.2 5360 JG (II'c ; X = -CH(OH)-CH 2-OH) (0.5) 344.7 296.5 6.7 91.0 5228 JG (II'd ; p = 6) (1.0) 208.9 256.3 6.7 89.0 (AIIdl7) (II'd ; p = 17)(1.0) 77.9 150.8 3.6 89.9 5394 JG (II'd ; p = 17) (2.0) 61.1 102.5 0.2 99.0 5370 JG (Il'e ; q = 8) (0.5) 302.3 292.2 10.5 Not measured 5361 JG (Il'e ; q = 10) (0.5) 275.7 283.5 8.1 88.0 5302 JG (H'e ; q = 12) (0.5) 264.0 216.7 9.2 85.3 (Allf) (Il'f) (1.0) 115.2 120.9 6.5 79.3 (Allg) (Il'g) (1.0) 104.3 250.3 4.7 85.0 (Allh) (II'gB) (1.0) 74.0 124.3 4.0 Not measured

[0131] a)Determined by HPLC / UV in the presence of an internal standard,

[0132] b) Conversion rate = [1- ((mass composition (A) x % (I) residual) / mass itaconic acid at the start)] x 100.

[0133] -Table 1- Characteristics of the compositions of mono- and / or oligoesters of itaconic acid (A) prepared.

[0134] Overall, the esterification conditions as described above make it possible to isolate compositions (A) having ester indices of between 100 and 350 mg KOH / g, indicating the significant formation of esterified species.

[0135] In all cases, the acid numbers are greater than 0, between 60 and 350 mg KOH / g. These values ​​indicate that all the carboxylic acid functions of itaconic acid (I) are not esterified.

[0136] Finally, the conversion rates calculated from the final mass of composition (A) collected, the percentage of residual itaconic acid (I) contained in this final mass and determined by CPG as well as the mass of itaconic acid (I) used at the start, are systematically greater than 75% indicating a satisfactory progress of the esterification reactions.

[0137] E.2- Preparation of poly(itaconate) (P) according to the invention:

[0138] E.2.1- Polymerization of the composition of glycerol monostearate itaconates (Allg) in isopar™ M to obtain the composition (Cl):

[0139] In a reactor, 26.7 g of the composition (Allg) are dissolved in 28.1 g of Isopar ™ M. The solution is homogenized with stirring at approximately 400 rpm at a temperature of 50°C and then subjected to nitrogen bubbling for 45 min in order to remove oxygen from the medium. The medium is then heated to a temperature of 80°C. 110 mg of lauroyl peroxide are then added to initiate the polymerization reaction. The medium becomes more viscous. After 2 h, 55 mg of lauryl peroxide are then introduced. After holding for an additional 3 h, the composition (Cl) has a waxy appearance and is hot-packed.

[0140] E.2.2- Polymerization of the composition of glycerol monostearate itaconates referenced (Allg) in a coco-caprylate / caprate composition marketed under the brand name DUB 810 C) to obtain the composition (C2):

[0141] The same procedure as that described in paragraph E.2.1- was implemented by replacing the 28.1 g of Isopar™ M oil with 28.1 g of DUB 810 C. Composition (C2) was isolated.

[0142] E.2.3- Polymerization of the composition of batyl alcohol itaconates (Allf) in the DUB 810 C to obtain the composition (C3):

[0143] The same operating mode as that described in paragraph E.2.2- was implemented by replacing the 26.7 g of composition (Allg) with 26.7 g of composition (Allf). Composition (C3) was isolated.

[0144] E.2.4- Summary table:

[0145] [Tables2] Reference Composition (C) Monomer(s) of the Polymer (P) [mass ratio in the case of copolymer] Oil (Hl) Mass ratio (P) / (H1) (Cl) Composition (Allg) Glycerol monosterate itaconates Isopar™ M 0.49 / 0.51 (C2) Composition (Allg) Glycerol monosterate itaconates DUB 810 C 0.49 / 0.51 (C3) Composition (Allf) Batyl alcohol itaconates DUB 810 C 0.49 / 0.51

[0146] -Table 2- Characteristics of the polymers (P) and compositions (C) prepared.

[0147] E3- Evaluation of the thickening properties of the compositions (C):

[0148] At 80°C, 0.7 g of compositions (Cl) to (C3) is solubilized in 5 g of two oils (H2) different: Primol™ 352 and Emogreen™ L19. The solutions thus obtained are cooled to room temperature and their thickening is assessed visually.

[0149] The results obtained are gathered in Table 3 below.

[0150] [Tables3] Reference Composition (C) Primol™ 35 2 Emogreen™ L 19 (Cl) ++ +++ (C2) ++ Not measured (C3) ++ Not measured

[0151] ++: Viscous consistency,

[0152] +++: Gelled consistency,

[0153] -Table 3- Thickening properties of oils (H2) of compositions (C).

[0154] Generally, viscous or gelled consistencies were visualized for the two oils (H2) differing in their chemical structure and polarity.

Claims

Claims

1. Thickening composition (C) of polar and / or apolar oils (H2), comprising at least one oil (H1) and a poly(itaconate) (P), the poly(itaconate) (P) being constituted by: - at least one monomeric unit derived from itaconic acid of formula (I) in free acid form or partially or totally salified And - at least one monomeric unit derived from a compound of formula (II): with identical Y and Y' representing the radical -ORi, or different Y and Y' representing either the radical -OH or the radical -ORi, with Ri representing: (a) a linear or branched, saturated or unsaturated aliphatic hydrocarbon radical (IIa), containing from 6 to 36 carbon atoms and optionally substituted with one or more hydroxyl groups, Or b) a radical of formula (IIb) in which R2 represents a linear or branched, saturated aliphatic hydrocarbon radical or unsaturated, containing 6 to 36 carbon atoms and optionally substituted with one or more hydroxyl groups: Or c) a radical of formula (Ile) in which R3-C(=O) represents a saturated or unsaturated, linear or branched hydrocarbon acyl radical containing from 12 to 24 carbon atoms, and more particularly a radical chosen from the elements of the group consisting of the dodecanoyl, tetradecanoyl, hexadecanoyl, octadecanoyl, ei-cosanoyl, docosanoyl, oleyl, linoleyl, linolenoyl or isostearyl radicals, and in which x represents a natural whole number greater than or equal to 1 and less than or equal to 6: Or d) a radical of formula (Ild) in which m represents an integer greater than or equal to 2 and less than or equal to 10: OH(IId) Or e) a radical of formula (Ile) in which o represents a number integer greater than or equal to 2 and less than or equal to 4: Or f) a radical of formula (Ilf):

2.

3.

4.

5.

6. (Ilf) g) a radical of formula (Ilg): (Ilg) h) a radical of formula (IIh) in which q represents an integer greater than or equal to 1 and less than or equal to 12, more particularly greater than or equal to 3 and less than or equal to 8: (Ilh). OH q Thickening composition (C) according to claim 1, characterized in that it comprises between 20% and 80% by mass of oil (Hl) and between 20% and 80% by mass of poly(itaconate) (P). Thickening composition (C) according to one of claims 1 or 2, characterized in that the oil (Hl) is an oil found in liquid form at a temperature between 4°C and 45°C, even more preferably between 15°C and 45°C, and even more preferably between 15°C and 35°C. Thickening composition (C) according to one of claims 1 to 3, characterized in that the oil H1 is a mineral oil or of vegetable origin or a mixture of these two types of oils. Formulation for topical use (F) comprising a composition (C) as defined in one of claims 1 to 4. Process for preparing a thickening composition (C) as defined in one of claims 1 to 4, comprising the steps following: a. Production of a composition (CO) of mono- and / or oligoesters of itaconic acid comprising a compound of formula (I) in free acid form or partially or totally salified of formula and a compound of formula (II): n (he), with Y and Y' identical representing the radical -ORi, or Y and Y' different representing either the radical -OH or the radical -ORi, with Ri representing: • a linear or branched, saturated or unsaturated aliphatic hydrocarbon radical (IIa), containing 6 to 36 carbon atoms and optionally substituted with one or more hydroxyl groups, Or • a radical of formula (IIb) in which R2 represents a linear or branched, saturated or unsaturated aliphatic hydrocarbon radical, comprising from 6 to 36 carbon atoms and optionally substituted with one or more hydroxyl groups: (Ilb) Or a radical of formula (Ile) in which R3-C(=O) represents a hydrocarbon acyl radical, saturated or unsaturated, linear or branched, containing from 12 to 24 carbon atoms, and more par- in particular a radical chosen from the elements of the group consisting of the radicals dodecanoyl, tetradecanoyl, hexadecanoyl, octadecanoyl, eicosanoyl, docosanoyl, oleyl, linoleyl, linolenoyl or isostearyl, and in which x represents a natural whole number greater than or equal to 1 and less than or equal to 6: Or a radical of formula (Ild) in which m represents an integer greater than or equal to 2 and less than or equal to 10: (Ild) Or • a radical of formula (Ile) in which o represents an integer greater than or equal to 2 and less than or equal to 4: a radical of formula (Ilf): a radical of formula (Ilg): a radical of formula (Ilh) in which q represents an integer greater than or equal to 1 and less than or equal to 12, more particularly greater than or equal to 3 and less than or equal to 8: a. Preparation of a mixture (Ml) of the composition (CO) produced in step a) with an oil (Hl), b. Polymerization of the mixture (Ml) initiated by introducing a thermal radical initiator into said mixture (Ml) obtained at the end of step b), and c. Recovery of composition (C).

7. Method according to claim 6, characterized in that it comprises a step of removing at least part of the oil (Hl) included in the composition (C). ^Claim 8] Process according to one of claims 6 or 7, characterized in that the polymerization is carried out at a temperature between 40°C and 80°C. ^Claim 9] Process according to one of claims 6 to 8, characterized in that in step b) a crosslinking monomer (AR) is added. ^Claim 10] Process according to claim 9, characterized in that the crosslinking monomer (AR) is a diethylenic or poly-ethylene crosslinking monomer chosen in particular from ethylene glycol dimethacrylate, diethylene glycol diacrylate, ethylene glycol diacrylate, diallyl urea, triallylamine, trimethylol propane triacrylate, methylene bis(acrylamide).^Claim 11] Process according to one of claims 6 to 10, characterized in that step a) of producing a composition (CO) of mono- and / or oligoesters of itaconic acid comprises the following sub-steps: i) Introduction into a reactor of a biosourced alcohol or polyol selected from the elements of the group consisting of compounds in liquid form: - oligoglycerols of the following structure: r (n'a) | m 6 H With m representing an integer greater than or equal to 2 and less than or equal to 10, - natural polyols of the following structure: r 1 (II'b) HO XOH Y° OH With o representing a number equal to 2 (erythritol), or equal to 3 (xylitol), or equal to 4 (sorbitol), - dehydrated natural polyols of the following structure:. With X representing a hydrogen atom (erythritan), or the radical -CH2-0H (xylitan) or the radical -CH(0H)-CH2-0H (sorbitan), - aliphatic fatty alcohols of the following structure: RI--OH (H'd) With RI representing a linear or branched, saturated or unsaturated, aliphatic hydrocarbon radical containing from 6 to 36 carbon atoms and optionally substituted with one or more hydroxyl groups, - the a,co-diols of formula (II'e) following: r „ i (II ' e) hoT "Toh L jq With q representing an integer greater than or equal to 1 and less than or equal to 12, - compounds of the following formula (Il'f): (Il'f) with R' 1 representing a linear or branched, saturated or unsaturated, aliphatic hydrocarbon radical containing from 6 to 36 carbon atoms and optionally substituted with one or more hydroxyl groups, - the compounds of formula (II'g) following: (Il'g) with R' 1-C(=O) representing a linear or branched, saturated or unsaturated hydrocarbon acyl radical containing from 12 to 24 carbon atoms and x representing an integer greater than or equal to 1 and less than or equal to 6, ii) Addition to the reactor, placed under mechanical stirring, of itaconic acid (I), of a polymerization inhibitor then of an esterification catalyst, iii) Maintenance of the medium present in the reactor at a temperature between 120°C and 180°C, under partial pressure, to carry out an esterification reaction, and iv) Recovery of a composition of mono- and / or oligoesters of itaconic acid.

12. Method according to claim 11, characterized in that sub-steps i) to iii) are carried out at a temperature between 120°C and 180°C,

13. Method according to one of claims 11 or 12, characterized in that sub-step iii) is carried out at a pressure of between 500 and 20 mbar and, more particularly, between 500 and 200 mbar.

14. Method according to one of claims 11 to 13, characterized in that sub-step iii) has a duration of between 30 minutes and 10 hours.

15. Process according to one of claims 11 to 14, characterized in that in sub-step ii) the polymerization inhibitor is chosen from 1,4-Benzoquinone, 2-tert-Butyl-1,4-benzoquinone, Phenothiazine, 6-tert-Butyl-2,4-xylenol, Copper(II) Dibutyldithiocarbamate, 1,1-Diphenyl-2-picrylhydrazyl, 2,6-Di-tert-butyl-p-cresol, 4-tert-Butylpyrocatechol-2,6-Di-tert-butylphenol, Hydroquinone, tert-Butylhydroquinone and 4-methoxyphenol.

16. Process according to one of claims 11 to 15, characterized in that in sub-step ii) the esterification catalyst is an acid chosen from sulfuric, hydrochloric, phosphoric, nitric, hypophosphorous, methanesulfonic, para-toluenesulfonic, trifluoromethanesulfonic acids and acid ion exchange resins.