Process for preparing one or more mixtures of glucose esters and C12-C22 fatty acids by enzymatic means

Abstract

The present invention relates to a process for preparing one or more mixtures of glucose and C12-C22 fatty acid esters, comprising at least one step of esterifying one or more mixtures of C12-C22 fatty acids and glucose, carried out enzymatically in a medium comprising one or more polar organic solvents with a boiling point at atmospheric pressure of 200 °C or lower. The invention also relates to one or more mixtures of glucose and C12-C22 fatty acid esters that can be obtained by esterifying one or more mixtures of C12-C22 fatty acids and glucose, in the presence of at least one enzyme, in a medium based on one or more polar organic solvents with a boiling point at atmospheric pressure of 200 °C or lower.The present invention also relates to the use of at least one mixture of glucose esters and C12-C22 fatty acids, as defined above, and / or at least one composition comprising at least one such mixture of glucose esters and C12-C22 fatty acids, for the cosmetic treatment of keratinous materials, in particular human keratin fibers and / or skin.

Description

Title of the invention: Process for preparing one or more mixtures of glucose esters and C fatty acids 12 -C 22 via enzymatic pathway

[0001] The present invention relates to a process for preparing one or more mixture(s) of glucose esters and C[2-C22] fatty acids, comprising at least one step of esterifying one or more mixture(s) of C[2-C22] fatty acid(s) and glucose, carried out enzymatically in a medium comprising one or more polar organic solvent(s) with a boiling point at atmospheric pressure less than or equal to 200 °C, particularly between 50°C and 195°C, more particularly between 55°C and 193°C, preferably between 60 °C and 190 °C, more preferably between 75°C and 189.5°C, in particular between 100°C and 189 °C.

[0002] The invention also relates to one or more mixtures of glucose esters and Ci2-C22 fatty acids that can be obtained by esterification of one or more mixtures of Ci2-C22 fatty acids and glucose, in the presence of at least one enzyme, in a medium based on or on polar organic solvent(s) with a boiling point at atmospheric pressure less than or equal to 200 °C.

[0003] The present invention also relates to the use of at least one mixture of glucose esters and fatty acids in C12-C22, as defined above, and / or of at least one composition comprising at least one such mixture of glucose esters and fatty acids in C12-C22, for the cosmetic treatment of keratinous materials, in particular human keratinous fibers and / or skin.

[0004] The invention further relates to a process for the cosmetic treatment of keratinous materials, preferably of human skin and / or keratinous fibers, employing at least one mixture of glucose esters and C[2-C22] fatty acids, as defined above, and / or at least one composition comprising at least one such mixture of glucose esters and C[2-C22] fatty acids.

[0005] The present invention relates to the field of cosmetic treatment of keratinous materials, in particular human keratinous fibers, such as hair, eyebrows, eyelashes and / or body hair, in particular beard hair, moustache hair and / or pubic hair, and / or skin, in particular the scalp and areas of skin, in particular one or more alopecic or non-alopecic areas, preferably alopecic, covered with keratinous fibers as previously mentioned.

[0006] More particularly, the invention relates to the cosmetic treatment of human hair and / or eyelashes and / or skin, preferably hair and / or scalp.

[0007] Hair growth and renewal in humans are primarily determined by the activity of hair follicles and their dermo-epidermal environment. Their activity is cyclical and essentially comprises three phases: the anagen phase, the catagen phase, and the telogen phase.

[0008] The anagen phase (corresponding to the active or growth phase), which lasts several years and during which the hair lengthens, is followed by a very short and transient catagen phase lasting a few weeks. During this phase, the hair undergoes a transformation, the follicle atrophies, and its dermal implantation appears increasingly higher.

[0009] The terminal phase, which lasts a few months, corresponds to a resting phase, called the telogen phase. At the end of this resting period, the hairs fall out and make way for new hair follicles in the anagen phase so that another hair cycle can begin.

[0010] Hair is therefore constantly renewing itself, and of the approximately 150,000 hairs in a head of hair, at any given moment, about 10% of them are at rest and will therefore be replaced in a few months.

[0011] Alopecia, which refers to the accelerated loss of hair, eyelashes, eyebrows and / or body hair, generally occurs in genetically predisposed individuals and primarily affects men. This is then referred to as androgenetic alopecia, androgenic alopecia, or androgen-genetic alopecia.

[0012] Alopecia is essentially due to a disruption of hair renewal, which initially leads to an acceleration of the cycle frequency at the expense of hair quality and then its quantity. This results in a progressive thinning of the hair through the regression of so-called "terminal" hairs to the vellus stage. Certain areas are preferentially affected; in men, in particular, the temporal or frontal hairline and the upper part of the occipital region, while in women, diffuse alopecia of the vertex is more common.

[0013] Other causes can lead to significant hair loss, whether temporary or permanent. These include hair loss and alteration after pregnancy (or postpartum), during periods of malnutrition or dietary imbalances, or during periods of asthenia or hormonal dysfunction, such as may occur during or after menopause. Hair loss or alteration may also be related to seasonal phenomena.

[0014] Alopecia can also affect eyelashes, eyebrows and / or hair on any part of the human body and can cause aesthetic discomfort in the same way as alopecia affecting one or more areas of the scalp.

[0015] People thus subject to alopecia are increasingly resorting to cosmetic treatments to suppress and / or reduce the effect of alopecia, and in particular to decrease or delay the loss of hair, eyelashes and / or body hair, as well as to induce or stimulate their growth.

[0016] Such treatments generally consist of daily applications to the various alopecic areas of the human body, in particular to the alopecic areas of the scalp, such as the temporal or frontal temples in men, and / or areas of the body without hair, in particular on the face, including the beard, moustache and / or eyebrows, of cosmetic compositions comprising one or more anti-hair loss agents and / or agents capable of promoting regrowth.

[0017] For this purpose, among the agents capable of reducing hair loss and / or promoting the regrowth of keratin fibers and / or treating the scalp and areas of skin, whether alopecic or not, we can notably mention agents such as finasteride, minoxidil, aminexil or even stemoxydine.

[0018] Furthermore, O-acylated glucose derivatives, particularly glucose 6-O-linoleate, which is derived from a mixture of glucose esters and Ci2-C22 fatty acids obtained by esterification of vitamin F and glucose, are also known to induce and / or stimulate the growth of keratin fibers, especially hair, and to effectively reduce hair loss. Such O-acylated glucose derivatives have the advantage of being naturally present in the human body and are more stable over time than free fatty acids.

[0019] The mixtures of glucose esters and fatty acids in C12-C22 are most often obtained in several steps by way of chemical synthesis, for example by forming a mixed anhydride by reaction between pivaloyl chloride and the mixture of fatty acids in C12-C22, in toluene or tetrahydrofuran, at temperatures ranging from 0 to 5°C, then by esterifying the mixed anhydride thus formed with glucose, at a temperature of about 25°C in pyridine.

[0020] The mixtures of glucose esters and fatty acids in the Ci2-C22 group are thus obtained by heating and using petrochemical solvents, such as toluene and pyridine, to remove water from the reaction medium in order to shift the reaction towards the formation of esters. Alternatively, chemical synthesis processes can employ a Dean-Stark reaction to remove water from the reaction medium.

[0021] Such chemical synthesis processes have the disadvantage of implementing several purification steps in order to recover the mixtures of glucose and fatty acid esters in Ci2-C22, in particular steps of filtration of by-products, for example a step of trapping hydrochloric acid, produced during the formation of the mixed anhydride, by trimethylamine, steps of distillation, concentration, extraction and molecular distillation, involving the use of large quantities of organic solvents, for example toluene, pyridine, heptane and butanol, as well as a very large consumption of energy.

[0022] Furthermore, the chemically synthesized mixtures of glucose esters and fatty acids in Ci2-C22 are obtained in the form of a sticky, thick paste of brown or yellowish color which needs to be treated, for example by heating, in order to be subsequently handled for cosmetic applications.

[0023] Furthermore, chemical synthesis processes also have the disadvantage of leading to mixtures of esters formed at different positions on glucose, particularly for hexoses. Indeed, in the case of the chemical synthesis of glucose 6-O-linoleate, the preparation processes also lead to a mixture of six positional isomers corresponding to five esterification positions of glucose for each alpha and beta anomer. Thus, chemical synthesis processes of glucose 6-O-linoleate have the disadvantage of not being regioselective and regiospecific.

[0024] Furthermore, chemical synthesis processes generally result in the formation of mixtures of glucose and fatty acid monoesters in C[2-C22] and glucose and fatty acid diesters in Ci2-C22.

[0025] In other words, the chemical synthesis processes of mixtures of glucose esters and C[2-C22] fatty acids have the major disadvantages of still consuming too much energy, implementing a number of purification steps, inducing significant operating costs, using large quantities of organic solvents, forming mixtures of positional isomers on glucose and mixtures of monoesters and diesters, and leading to a non-crystalline and difficult-to-handle product.

[0026] In view of the foregoing, one of the objectives of the present invention is to overcome the aforementioned drawbacks, that is to say, to propose a method for the synthesis of at least one mixture of glucose esters and C[2-C22] fatty acids, in particular simpler to implement than the methods classically described in the prior art, for example in terms of the number of reaction steps and / or the number of purification steps, involving fewer solvents, capable of limiting the formation of mixtures of positional isomers on glucose and diesters, while leading to a product that is easier to handle and, above all, solid, whereas the chemical form was difficult to handle because it was of the "honey" type and had to be heated beforehand to be handled.

[0027] In particular, one of the aims of the present invention is to propose a process for the synthesis of at least one mixture of glucose esters and C12-C22 fatty acids having a better carbon footprint than the processes classically described in the prior art and which can be efficiently implemented for cosmetic applications, in particular for the cosmetic treatment of keratinous materials, in particular human keratinous fibers and / or skin.

[0028] Thus, one of the aims of the present invention is in particular to propose a process for preparing at least one mixture of glucose esters and C12-C22 fatty acids comprising at least one esterification step of at least one mixture of C12-C22 fatty acids and at least glucose, carried out enzymatically in a medium comprising one or more polar organic solvent(s) with a boiling point at atmospheric pressure less than or equal to 200 °C as defined above, particularly between 50 °C and 195 °C, more particularly between 55 °C and 193 °C, preferably between 60 °C and 190 °C, more preferably between 75 °C and 189.5 °C, particularly between 100 °C and 189 °C.

[0029] The enzymatic preparation process according to the invention thus makes it possible to achieve the objectives as described above, that is to say that it leads to one or more mixtures of glucose esters and C12-C22 fatty acids in a crystalline form, in particular in the form of a white powder easily handled for cosmetic applications, in particular for the treatment of keratinous materials, with a satisfactory yield while presenting an optimized implementation compared to the chemical synthesis processes described in the state of the art, in particular in terms of the number of reaction steps and / or the number of purification steps and / or fewer solvents.

[0030] The enzymatic synthesis process according to the invention makes it possible to produce one or more mixtures of glucose and C12-C22 fatty acid esters in crystalline form, with satisfactory conversion rates and yields while minimizing the number of purification steps, in particular the number of isolation operation steps, compared to the chemical synthesis processes classically described in the prior art.

[0031] In other words, the enzymatic synthesis process according to the invention makes it possible to achieve a gain in the number of purification steps, in particular the number of steps with isolation, while maintaining a satisfactory conversion rate and yields.

[0032] The synthesis process according to the invention makes it possible in particular to significantly reduce the quantities of solvents, in particular those derived from petrochemicals.

[0033] The enzymatic synthesis process according to the invention also has the advantage of being regiospecific and regioselective and of leading to cosmetic actives that are easily handled and capable of cosmetically treating keratinous materials, preferably human keratinous fibers and / or skin.

[0034] Thus the enzymatic synthesis process according to the invention makes it possible to minimize, or even eliminate, the formation of positional isomers on glucose in the mixture(s) of glucose esters and fatty acids in Ci2-C22 obtained.

[0035] Advantageously, the process according to the invention makes it possible to produce a mixture of glucose and fatty acid esters in Ci2-C22 in which the glucose is esterified predominantly at position 6.

[0036] Even more advantageously, the process according to the invention makes it possible to significantly reduce, or even eliminate, the formation of glucose and fatty acid diesters in Cj2-C22.

[0037] In other words, the process according to the invention advantageously leads to the formation of monoesters of glucose and fatty acids in Ci2-C22.

[0038] By way of example, the enzymatic synthesis process according to the invention comprising the esterification of vitamin F and glucose makes it possible to produce glucose 6-O-linoleate and to minimize, or even eliminate, the presence of positional isomers on glucose as well as diesters usually obtained by chemical means.

[0039] In other words, in the case of glucose 6-O-linoleate, the enzymatic synthesis process according to the invention allows for the selective production of glucose monoesters at position 6.

[0040] In addition, the process according to the invention generates less effluent(s) than a chemical synthesis process.

[0041] The enzymatic synthesis process according to the invention thus has a satisfactory carbon footprint while being efficient in obtaining a mixture of glucose esters and fatty acids in C[2-C22.

[0042] The invention also relates to a mixture of glucose esters and C[2-C22] fatty acids that can be obtained by enzymatic esterification of one or more mixtures of Ci2-C22 fatty acids and glucose in a medium comprising one or more polar organic solvent(s) with a boiling point at atmospheric pressure of less than or equal to 200 °C as defined above.

[0043] In other words, the invention relates to an O-acylated glucose-derived product that can be obtained by enzymatic esterification of at least one mixture of C[2-C22] fatty acids and glucose, as defined above.

[0044] The mixture of glucose esters and fatty acids in Ci2-C22 thus obtained is therefore particularly advantageous for use in cosmetic applications, in particular for the cosmetic treatment of keratinous materials, preferably human keratinous fibers such as hair, and / or skin.

[0045] Furthermore, advantageously, glucose is esterified at position 6 in the mixture of glucose esters and fatty acids in Ci2-C22 or the O-acylated glucose-derived product according to the invention.

[0046] Another object of the present invention is thus a composition comprising at least a mixture of glucose esters and C[2-C22] fatty acids or an O-acylated glucose-derived product as described above.

[0047] Similarly, the present invention relates to the use of at least one mixture of glucose esters and fatty acids in C[2-C22], as defined above, and / or at least one composition comprising at least one such mixture of glucose esters and fatty acids in C[2-C22], for the cosmetic treatment of keratinous materials, in particular of the skin, especially the alopecic or non-alopecic area(s) of the skin, and / or human keratinous fibers such as hair, eyebrows, eyelashes and / or body hair.

[0048] Another object of the present invention relates to a process for the cosmetic treatment of keratinous materials, preferably of skin and / or human keratinous fibers, such as hair, eyebrows and / or eyelashes, in particular hair, employing at least one mixture of glucose esters and C[2-C22] fatty acids, as defined above, and / or at least one composition comprising at least one such mixture of glucose esters and C[2-C22] fatty acids.

[0049] Other objects, features, aspects and advantages of the invention will become even clearer upon reading the description and example that follows.

[0050] In what follows, and unless otherwise indicated, the bounds of a range of values ​​are included in that range, in particular in the expressions "between" and "ranging from ... to ...".

[0051] Furthermore, the expression "at least one" used in this description is equivalent to the expression "one or more".

[0052] Furthermore, the expression "at least" used in this description is equivalent to the expression "greater than or equal to". Finally, in a manner known per se, a compound or group in "Cn" or "Cn" is designated as a compound or group containing "n" carbon atoms in its chemical structure.

[0053] By "glucose" is meant monosaccharides which are pentose sugars with the molecular formula C5H1O2O5; or hexoses with the molecular formula C6H2O6, in open acyclic forms (aldoses) or ketoses), or closed cyclic including all stereoisomers: the (L, D) enantiomers, (L, D) diastereomers and the alpha a and beta anomers [3.

[0054] Preferably, glucose is chosen from among the hexoses, D-glucose and more particularly a-D-glucose and [3-D-glucose, more particularly a-D-glucose.

[0055] Preferably, the aD-glucopyranose and [3-D-glucopyranose] forms of the following respective formulas:

[0056] [Chem.l] OH [Chem.l] OH HQ A****t*X---oh OH

[0057] Preferably glucose corresponds to a mixture of aD-glucopyranose and [3-D-glucopyranose forms, and possibly an open form of D-glucose and more preferably the quantity of [3-D-glucopyranose is greater than that of aD-Glucopyranose, and possibly than that of D-glucose in open form of which the latter is in a quantity less than that of [3-D-glucopyranose and that of aD-glucopyranose.

[0058] By "polar organic solvent" is meant a solvent comprising carbon atoms, hydrogen atoms, and one or more heteroatoms preferably selected from oxygen, nitrogen, and sulfur atoms. In particular, the polar organic solvent(s) are composed of atoms with different electronegativities, the electronegativity difference being between 0.4 and 1.7, forming polarized bonds between them.

[0059] By “practical solvent” we mean that the polar solvents according to a second criterion, proticity, that is to say the capacity of the solvent to release acidic H+ ions or to create hydrogen bonds, i.e. generally comprising hydroxyl or amino groups.

[0060] By "polar aprotic organic solvent" one can cite di(Ci-C6)alkylketones such as acetone, di(Ci-C6)alkylsulfoxide such as DMSO, (Ci-C6)alkylnitrile, heterocycloalkyl and cycloalkyl(Ci-C6)alkoxy such as pyridine, THF, or cyclopentylmethyl ether CPME, or (Ci-C6)alkylcarbonyl(Ci-C6)alkoxy such as tert-butylacetate TBA.

[0061] By "protic polar organic solvent" one can cite the (C2-C10)alkan(poly)ols preferably the (C2-C8)alkanols such as ethanol, 2-Methyl-2-Butanol (2M2B). Preparation process

[0062] The process according to the invention relates to a process for preparing at least one mixture of glucose esters and fatty acids in Ci2-C22 comprising at least one esterification step of at least one mixture of fatty acids in Ci2-C22 and at least glucose, carried out enzymatically in a medium comprising one or more polar organic solvent(s) with a boiling point at atmospheric pressure less than or equal to 200 °C as defined above, particularly between 50 °C and 195 °C, more particularly between 55 °C and 193 °C, preferably between 60 °C and 190 °C, more preferably between 75 °C and 189.5 °C, in particular between 100 °C and 189 °C.

[0063] For the purposes of the present invention, "enzymatic route" means that the preparation process comprises at least one esterification of at least one mixture of C[2-C22] fatty acids and at least one glucose, in the presence of at least one enzyme as defined below. C12-C22 fatty acid mixture

[0064] Preferably, the mixture of fatty acids in Ci2-C22 is a mixture of saturated and unsaturated fatty acids in C[2-C22, preferably a mixture of saturated and unsaturated fatty acids in Ci2-C20, even more preferably a mixture of saturated and unsaturated fatty acids in Ci2-Ci8.

[0065] Preferably, the mixture of fatty acids in Ci2-C22 comprises at least linoleic acid.

[0066] According to a preferred embodiment, the mixture of fatty acids in Ci2-C22 comprises at least linoleic acid and at least one fatty acid in C[2-C22] other than linoleic acid.

[0067] According to a preferred embodiment, the mixture of fatty acids in Ci2-C22 comprises at least linoleic acid and at least one fatty acid in C[2-C22] other than linoleic acid selected from oleic acid, palmitic acid and stearic acid and mixtures thereof.

[0068] More preferably, the C[2-C22] fatty acid mixture comprises at least linoleic acid, at least oleic acid, at least palmitic acid and at least stearic acid.

[0069] Preferably, the mixture of fatty acids in Ci2-C22 comprises: - 70 to 80% by weight of linoleic acid, - 10 to 20% by weight of oleic acid, - 1 to 8% by weight of palmitic acid, - 0.5 to 5% by weight of stearic acid, - 0 to 3% by weight of saturated or unsaturated fatty acids comprising a number of carbon atoms greater than or equal to 20, - 0 to 10% by weight of one or more other acids chosen from lauric acid, myristic acid, arachidic acid, behenic acid, lauroleic acid, myristoleic acid, palmitoleic acid, linolenic acid and / or mixtures thereof;

[0070] the contents being calculated in relation to the total weight of the mixture of fatty acids in Ci2-C22.

[0071] The mixture of fatty acids in Ci2-C22 is preferably vitamin F.

[0072] Mixture of glucose and fatty acid esters in C n -C 22

[0073] Preferably, the process according to the invention is a process for preparing a mixture of glucose esters and fatty acids in Ci2-C20.

[0074] More preferably, the process according to the invention is a process for preparing a mixture of glucose esters and fatty acids in Ci2-Ci8.

[0075] The process according to the invention is in particular a process for preparing at least one mixture of glucose and fatty acid monoesters in C12-C22, preferably a mixture of glucose and fatty acid monoesters in Ci2-C2o, more preferably a mixture of glucose and fatty acid monoesters in Ci2-Ci8.

[0076] Preferably, the process according to the invention is a process for preparing a mixture of glucose and C12-C22 fatty acid esters comprising at least one glucose and linoleic acid monoester.

[0077] According to a preferred embodiment, the mixture of glucose and C12-C22 fatty acid esters comprises at least one glucose and linoleic acid monoester and at least one glucose and C12-C22 fatty acid monoester different from the glucose and linoleic acid monoester.

[0078] According to a preferred embodiment, the mixture of glucose and C12-C22 fatty acid esters comprises at least one glucose and linoleic acid monoester and at least one glucose and C12-C22 fatty acid monoester, different from the glucose and linoleic acid monoester, selected from the glucose and oleic acid monoester, the glucose and palmitic acid monoester, the glucose and stearic acid monoester and mixtures thereof.

[0079] More preferably, the mixture of glucose and fatty acid esters in Ci2-C22 comprises at least the glucose and linoleic acid monoester, at least the glucose and oleic acid monoester, at least the glucose and palmitic acid monoester and at least the glucose and stearic acid monoester.

[0080] Preferably, the mixture of glucose esters and C12-C22 fatty acids comprises: - i) 70 to 80% by weight of glucose and linoleic acid monoester, - ii) 10 to 20% by weight of glucose and oleic acid monoester, - iii) 1 to 8% by weight of glucose and palmitic acid monoester, - iv) 0.5 to 5% by weight of glucose and stearic acid monoester, - v) 0 to 3% by weight of saturated or unsaturated fatty acids comprising a number of carbon atoms greater than or equal to 20; - vi) 0 to 10% by weight of one or more other glucose and acid monoesters selected from glucose and lauric acid, myristic acid, arachidic acid, behenic acid, lauroleic acid, myristoleic acid, palmitoleic acid, linolenic acid and / or mixtures thereof;

[0081] the contents being calculated in relation to the total weight of the mixture of glucose esters and fatty acids in Ci2-C22.

[0082] According to one embodiment of the invention, the mixture of glucose esters and fatty acids in Ci2-C22 comprises, preferably consisting of, i) a glucose and linoleic acid monoester (or glucose linoleate), ii) a glucose and oleic acid monoester (or glucose oleate), iii) a glucose and palmitic acid monoester (or glucose palmitate), and iv) a glucose and stearic acid monoester (or glucose stearate), which can be obtained by the preparation process as defined above.

[0083] Preferably in the mixture of glucose esters and fatty acids in C12-C22, the amount by weight of i) is between 70 and 80% such as 74% by weight, the amount of ii) is between 10 and 20% by weight such as 15% by weight, the amount of iii) is between 1 and 8% by weight such as 4%, the amount of iv) is between 0.5 and 5% by weight such as 3%, and v) from 0 to 3% by weight of saturated or unsaturated fatty acids comprising a number of carbon atoms greater than or equal to C20, the amount of vi) is between 0 and 10% by weight of one or more other glucose monoesters and acids selected from glucose monoesters and lauric acid, myristic acid, arachidic acid, behenic acid, and other fatty acids. lauroleic acid, myristoleic acid, palmitoleic acid, linolenic acid and / or mixtures thereof, it being understood that the sum of the quantity by weight of the mixture i)+ii)+iii)+iv) +v) + vi) represents 100.

[0084] Advantageously, the mixture of glucose esters and fatty acids in Ci2-C22 comprises at least glucose esterified at position 6.

[0085] Advantageously still, the mixture of glucose esters and fatty acids in Ci2-C22 comprises at least glucose 6-O-linoleate.

[0086] Preferably, the mixture of glucose esters and fatty acids in Ci2-C22 comprises at least 50% by weight, preferably at least 60% by weight of glucose 6-O-linoleate, more preferably greater than or equal to 70% by weight, relative to the total weight of the mixture.

[0087] More preferably, the mixture of glucose esters and fatty acids in Ci2-C22 comprises at least 70 to 80% by weight of glucose 6-O-linoleate, relative to the total weight of the mixture. Enzyme

[0088] The process according to the invention is a process for preparing one or more mixtures of glucose and fatty acid esters in Ci2-C20 in the presence of at least one enzyme.

[0089] Preferably, the enzyme(s) is / are a lipase-type enzyme(s). In other words, the enzyme(s) is / are chosen from among the lipases.

[0090] Lipases are enzymes belonging to the hydrolase family (EC 3.1) which can be produced by different groups of microorganisms such as bacteria, molds and yeasts, or any type of lipase present in eukaryotes and prokaryotes, in immobilized or free form.

[0091] Preferably, the enzyme is lipase B from Candida antarctica.

[0092] Candida antarctica lipase B, named by the Anglo-Saxon acronym CAL B, is a carboxylic ester hydrolase type protein (EC 3.1.1.3, triacylglycerol-acylhydrolase) of 317 amino acids.

[0093] According to a particular embodiment of the invention, the enzyme or enzymes used in the process according to the invention are free such as Lipozyme ® CalB.

[0094] The structure of Cal B is formed of a beta sheet consisting of 8 parallel strands linked together by 6 alpha helices. The catalytic triad of this lipase consists of a serine (Serl05), an aspartic acid (Asp187) and a histidine (His224).

[0095] According to one embodiment, the enzyme or enzymes used in the process of the invention are immobilized such as Novozyme 435.

[0096] The enzyme is preferably a lipase B from Candida antarctica sold under the trade name Novozym 435 by the company Novonesis.

[0097] The enzyme(s) may be present in the reaction medium at a content of 0.1 to 5% by weight, preferably at a content of 0.1 to 1%, better at a content of 0.1 to 0.8% by weight such that 0.6% + / - 0.05%, relative to the total weight of the medium. Medium

[0098] As indicated above, the preparation process according to the invention takes place in a medium comprising one or more polar organic solvent(s) with a boiling point at atmospheric pressure less than or equal to 200 °C, particularly between 50 °C and 195 °C, more particularly between 55 °C and 193 °C, preferably between 60 °C and 190 °C, more preferably between 75 °C and 189.5 °C, in particular between 100 °C and 189 °C.

[0099] The medium is preferably an organic medium, that is to say a medium comprising less than 10% by weight of water, preferably less than 5% by weight of water, more preferably less than 2% by weight of water, relative to the total weight of the medium).

[0100] According to a preferred embodiment, the polar organic solvent(s) with a boiling point at atmospheric pressure of less than or equal to 200 °C, preferably between 60 °C and 190 °C, more preferably between 100 °C and 189 °C, is / are a mixture of at least two different solvents, at least one of which is a protic polar organic solvent, in particular selected from alcohols comprising one or more hydroxy groups and comprising from 2 to 10 carbon atoms, in particular from 3 to 6 carbon atoms such as 2-methyl-2-butanol (2M2B).

[0101] More preferably, the polar organic solvent(s) with a boiling point at atmospheric pressure less than or equal to 200 °C, particularly between 50 °C and 195 °C, more particularly between 55 °C and 193 °C, preferably between 60 °C and 190 °C, more preferably between 75 °C and 189.5 °C, in particular between 100 °C and 189 °C, is / are a mixture of at least two solvents, at least one of which is a protic polar organic solvent as defined above and the other is an aprotic polar organic solvent, in particular selected from a di(Ci-C6)alkyl sulfoxide such as DMSO, a heterocycloalkyl or cycloalkyl(Ci-C6)alkoxy such as CPME, or (Cr-C6)alkylcarbonyl(Ci-C6)alkoxy such as TBA, more preferably a di(Ci-C6)alkyl sulfoxide such as DMSO.

[0102] According to another particular embodiment, the polar organic solvent(s) with a boiling point at atmospheric pressure less than or equal to 200 °C, particularly between 50 °C and 195 °C, more particularly between 55 °C and 193 °C, preferably between 60 °C and 190 °C, more preferably between 75 °C and 189.5 °C, notably between 100 °C and 189 °C, comprises only one type of aprotic or protic polar organic solvent, preferably aprotic, notably selected from a di(Ci-C6)alkyl sulfoxide such as DMSO, a heterocycloalkyl or cycloalkyl(Ci-C6)alkoxy such as CPME, or (Ci-C6)alkylcarbonyl(Ci-C6)alkoxy such as TBA, more preferably a di(Ci-C6)alkyl sulfoxide such as DMSO.

[0103] According to an advantageous embodiment, the medium comprises dimethyl sulfoxide (DMSO) and optionally mixed with 2-methyl-2-butanol (2M2B).

[0104] According to a preferred embodiment, the medium comprises only dimethyl sulfoxide (DMSO).

[0105] According to a preferred embodiment, the medium comprises dimethyl sulfoxide (DMSO) and 2-methyl-2-butanol (2M2B).

[0106] Preferably where the polar organic solvent(s) with a boiling point at atmospheric pressure of 200 °C or less, particularly between 50 °C and 195 °C, more particularly between 55 °C and 193 °C, preferably between 60 °C and 190 °C, more preferably between 75 °C and 189.5 °C, in particular between 100 °C and 189 °C, is / are a mixture of at least two different solvents, at least one of which is an aprotic polar organic solvent as defined above and at least one protic polar organic solvent as defined above, the weight ratio of aprotic polar organic solvent to protic polar organic solvent ranging from 5 / 95 to 40 / 60 (mass / mass), preferably ranging from 10 / 90 to 30 / 70 (mass / mass), better ranging from 15 / 85 to 25 / 75 (mass / mass) such as 25 / 75 (mass / mass).

[0107] According to a preferred embodiment, the medium comprises dimethyl sulfoxide (DMSO) and 2-methyl-2-butanol (2M2B) in a DMSO / 2M2B weight ratio ranging from 5 / 95 to 30 / 70 (mass / mass), preferably ranging from 10 / 90 to 25 / 75 (mass / mass).

[0108] Preferably, the process according to the invention is a process for preparing at least one mixture of glucose and fatty acid esters in Ci2-C22 comprising at least one esterification step of at least one mixture of fatty acids in Ci2-C22 and at least one glucose, carried out enzymatically, in a medium comprising one or more polar organic solvent(s) with a boiling point at atmospheric pressure less than or equal to 200 °C, particularly between 50 °C and 195 °C, more particularly between 55 °C and 193 °C, preferably between 60 °C and 190 °C, more preferably between 75 °C and 189.5 °C, in particular between 100 °C and 189 °C as defined above.

[0109] More preferably, the process according to the invention is a process for preparing at least one mixture of glucose esters and C[2-C22] fatty acids comprising at least one esterification step of at least one mixture of C[2-C22] fatty acids and at least one glucose, carried out in the presence of at least one enzyme selected from lipases, preferably Candida antarctica lipase B, in a medium comprising one or more polar organic solvent(s) having a boiling point at atmospheric pressure less than or equal to 200 °C, particularly between 50 °C and 195 °C, more particularly between 55 °C and 193 °C, preferably between 60 °C and 190 °C, more preferably between 75 °C and 189.5 °C, in particular between 100 °C and 189 °C. as defined above.

[0110] Even more preferably, the process according to the invention is a process for preparing at least one mixture of glucose and fatty acid esters in Ci2-C22 comprising at least one esterification step between vitamin F and glucose, carried out in the presence of at least one enzyme selected from lipases, preferably lipase B from Candida antarctica, in a medium comprising one or more polar organic solvent(s) with a boiling point at atmospheric pressure less than or equal to 200 °C, particularly between 50 °C and 195 °C, more particularly between 55 °C and 193 °C, preferably between 60 °C and 190 °C, more preferably between 75 °C and 189.5 °C, in particular between 100 °C and 189 °C, as defined above.

[0111] Advantageously, the process according to the invention is a process for preparing at least one mixture of glucose esters and C12-C22 fatty acids comprising at least 50% by weight, preferably at least 60% by weight of glucose 6-O-linoleate, relative to the total weight of the mixture, said process comprising at least one esterification step between vitamin F and glucose, carried out in the presence of at least one enzyme selected from lipases, preferably Candida antarctica lipase B, in free or immobilized form, in a medium comprising one or more polar organic solvent(s) having a boiling point at atmospheric pressure less than or equal to 200 °C, particularly between 50 °C and 195 °C, more particularly between 55 °C and 193 °C, preferably between 60 °C and 190 °C, more preferably between 75 °C and 189.5 °C, including between 100 °C and 189 °C, as defined above. Esterification stage

[0112] Preferably, the process according to the invention comprises at least one esterification in the presence of: - of at least one mixture of C12-C22 fatty acids, in an equimolar amount or in excess of the amount of glucose, preferably in an amount ranging from 1.1 to 2.5 equivalents, in particular in an amount ranging from 1.2 to 1.9 equivalents, of a mixture of C12-C22 fatty acids, and - at least glucose, preferably D-glucose, in an amount equal to or less than that of the C12-C22 fatty acid mixture, - at least one enzyme, preferably at least one enzyme selected from lipases, more preferably Candida antarctica lipase B, in a concentration ranging from 0.1 to 5% by weight relative to the total weight of the medium, - in a medium comprising one or more polar organic solvent(s) with a boiling point at atmospheric pressure less than or equal to at 200 °C as defined above, preferably a mixture of two polar solvents, one of which is a polar aprotic organic solvent as defined above, preferably DMSO, and the other is a polar protic organic solvent as defined above, preferably 2M2B, - preferably, esterification is carried out at a temperature ranging from 40°C to 80°C, preferably ranging from 50°C to 70°C such as 60°C.

[0113] More preferably, the preparation process according to the invention comprises successively, in a medium comprising one or more polar organic solvent(s) having a boiling point at atmospheric pressure less than or equal to 200 °C, particularly between 50 °C and 195 °C, more particularly between 55 °C and 193 °C, preferably between 60 °C and 190 °C, more preferably between 75 °C and 189.5 °C, in particular between 100 °C and 189 °C, as defined above: - at least the addition of one or more aprotic polar organic solvent(s) as defined above, preferably chosen from a di(Ci-C6)alkyl sulfoxide such as DMSO, a heterocycloalkyl or cycloalkyl(Ci-C6)alkoxy such as CPME, or (Ci-C6)alkylcarbonyl(Ci-C6)alkoxy such as TB A, more preferably a di(Ci-C6)alkyl sulfoxide such as DMSO; - at least the addition of glucose, preferably D-glucose, in particular a mixture of αD-glucopyranose and [3-D-glucopyranose forms, and possibly an open form of D-glucose; - at least the addition of one or more protic polar organic solvent(s) as defined above, preferably 2M2B, - at least the addition of at least one mixture of C12-C22 fatty acids, preferably in an equimolar quantity or in excess relative to the amount of glucose, preferably in an amount ranging from 1.1 to 2.5 equivalents, - at least the addition of at least one enzyme, preferably at least one enzyme chosen from among the lipases, more preferably lipase B from Candida antarctica.

[0114] Preferably, during the preparation process according to the invention, the temperature varies from -5 °C to 130 °C, particularly between 10 °C and 125 °C, 40 °C to 120 °C, preferably ranging from 50 °C to 80 °C such as 60 °C. Additional steps

[0115] The process according to the invention may optionally include one or more additional steps carried out after the esterification step(s), in particular implementation(s) to recover the mixture of glucose esters and fatty acids Ci2-C22 with a very high regiospecificity, or conversion rate.

[0116] At the end of the esterification step(s), the medium comprising at least the mixture of glucose esters and C12-C22 fatty acids can successively be filtered, heated to a temperature of -5 °C to 130 °C, particularly between 10 °C and 125 °C, particularly 40 °C to 120 °C, preferably from 50 °C to 80 °C such as 60 °C, possibly under reduced pressure, and then can be cooled to a temperature of -5 °C to 25 °C to obtain the mixture of glucose esters and C12-C22 fatty acids in a crystalline form.

[0117] According to a particular embodiment, the process according to the invention may include at least one further step of one or more polar organic solvent(s) having a boiling point at atmospheric pressure less than or equal to 200 °C.

[0118] According to a particular embodiment, once the esterification reaction is complete, the reaction medium (RM) is filtered and then: - either the MR is passed through one or more passes in so-called "short-path distillation" – also known as molecular distillation; and / or - the MR is passed in one or more passes in distillation called "scraped film"; - either the protic polar organic solvent(s) as defined above, preferably 2M2B is evaporated at a temperature between 50 °C and 65 °C such as 60 °C + / - 2 °C under a reduced pressure between 100 and 150 mbar and the aprotic polar organic solvent(s) as defined above, preferably chosen from a di(Ci-C6)alkyl sulfoxide such as DMSO, a heterocycloalkyl or cycloalkyl(Ci-C6)alkoxy such as CPME, or (Ci-C6)alkylcarbonyl(Ci-C6)alkoxy such as TB A, more preferably a di(Ci-C6)alkyl sulfoxide such as DMSO, the polar organic solvent(s) aprotic(s) is / are evaporated under a pressure less than or equal to 3 mbars, at a temperature greater than or equal to 90 °C, preferably between 100 °C and 120 °C such as 115 °C.

[0119] According to a particular embodiment, after the addition of the aprotic polar organic solvent(s) as defined above, in particular ethyl acetate, the residual DMSO and glucose from the MR are extracted with water and then optionally the reaction medium is passed in one or more passes by so-called "short path" distillation and / or said medium is passed in one or more passes by so-called "scraped film" distillation.

[0120] According to a particular embodiment of the invention, the MR is carried out using a Dean Stark apparatus at atmospheric pressure, followed by distillation under reduced pressure. In particular, the mixture of the invention is then crystallized by the addition of a polar aprotic solvent such as acetone and then filtered. It can then be re-packed in said solvent and dried under vacuum (such as ≤ 20 mbar), preferably at room temperature 25 °C, and optionally recrystallized in a polar organic solvent such as acetone or even a mixture of organic solvents such as acetone / ethyl acetate. According to one variant, the mixture is between 50 / 50 acetone / ethyl acetate and 90 / 10 acetone / ethyl acetate.

[0121] Advantageously, the mixture of glucose esters and fatty acids Ci2-C22 is obtained in the form of a solid, preferably in the form of particles, more preferably in the form of a white powder, with a good glucose conversion rate (greater than or equal to 30%).

[0122] Mixture of glucose esters and C nC fatty acids

[0123] The present invention also relates to a mixture of glucose esters and C[2-C22] fatty acids that can be obtained by enzymatic esterification of one or more mixtures of Ci2-C22 fatty acids and glucose in a medium comprising one or more polar organic solvent(s) with a boiling point at atmospheric pressure of less than or equal to 200 °C.

[0124] In other words, the present invention relates to a mixture of glucose esters and C[2-C22] fatty acids that can be obtained by the process according to the invention as described above.

[0125] In other words, the present invention relates to an O-acylated glucose-derived product that can be obtained by enzymatic esterification of at least one mixture of Ci2-C22 fatty acids and glucose in a medium comprising one or more polar organic solvent(s) with a boiling point at atmospheric pressure of less than or equal to 200 °C.

[0126] The mixture of glucose esters and fatty acids in C[2-C22] is as defined above.

[0127] Preferably, the mixture of glucose and fatty acid esters in C[2-C22] comprises at least one glucose and linoleic acid monoester and at least one glucose and fatty acid monoester in Ci2-C22 different from the glucose and linoleic acid monoester.

[0128] Preferably, the mixture of glucose esters and fatty acids in C[2-C22] comprises at least glucose esterified at position 6.

[0129] Preferably, the mixture of glucose esters and fatty acids in Ci2-C22 comprises at least glucose 6-O-linoleate.

[0130] Preferably, the mixture of glucose esters and fatty acids in Ci2-C22 comprises at least 50% by weight of glucose 6-O-linoleate, in particular at least 60% by weight of glucose 6-O-linoleate, relative to the total weight of the mixture.

[0131] More preferably, the invention relates to a mixture of glucose esters and fatty acids in Ci2-C22 comprising at least glucose 6-O-linoleate, preferably in a content of 75% to 80% by weight relative to the total weight of the mixture, which can be obtained by the process as defined above.

[0132] In other words, the invention relates to an O-acylated glucose-derived product comprising at least glucose 6-O-linoleate, preferably in a content of 75% to 80% by weight relative to the total weight of the O-acylated product, which can be obtained by the process as defined above. Composition

[0133] Another object of the present invention relates to a composition comprising at least one mixture of glucose esters and fatty acids in Ci2-C22 capable of being obtained by the preparation process as described above.

[0134] The mixture of glucose esters and fatty acids in Ci2-C22 is as defined above.

[0135] In other words, the composition according to the invention comprises at least one O-acylated product derived from glucose capable of being obtained by esterification, as defined above, by enzymatic means of at least one mixture of C[2-C22] fatty acids and glucose in a medium comprising one or more polar organic solvent(s) with a boiling point at atmospheric pressure less than or equal to 200 °C.

[0136] Preferably, the O-acylated glucose-derived product or the mixture of glucose and fatty acid esters in C[2-C22] comprises at least one glucose and linoleic acid monoester and at least one glucose and fatty acid monoester in Ci2-C22 different from the glucose and linoleic acid monoester.

[0137] Preferably, the O-acylated glucose-derived product or the mixture of glucose and fatty acid esters in Ci2-C22 comprises at least glucose esterified at position 6.

[0138] Preferably, the O-acylated glucose-derived product or the mixture of glucose esters and C[2-C22] fatty acids comprises at least glucose 6-O-linoleate.

[0139] More preferably, the product comprises at least 50% by weight, in particular at least 60% by weight of glucose 6-O-linoleate relative to the total weight of the product.

[0140] Preferably, the composition comprises at least one O-acylated product derived from glucose or at least one mixture of glucose esters and fatty acids in C12-C22 in a content ranging from 0.01 to 20% by weight, more preferably in a content ranging from 0.1 to 10% by weight, even more preferably in a content ranging from 0.5 to 5% by weight, relative to the total weight of the composition.

[0141] The composition may further comprise water and optionally one or more organic solvents.

[0142] Examples of organic solvents include C2-C6 alcohols such as ethanol and isopropanol; polyols and polyol ethers such as 2-butoxyethanol, propylene glycol, propylene glycol monomethyl ether, diethylene glycol monoethyl ether and monomethyl ether, as well as aromatic alcohols such as benzyl alcohol or phenoxyethanol, and mixtures thereof.

[0143] Preferably, the organic solvent(s) is or are chosen from C2-C6 alcohols, more preferably ethanol.

[0144] The organic solvent(s) is or are preferably present in the composition in a total quantity ranging from 1 to 60% by weight, more preferably from 10 to 50% by weight and even more preferably in a total quantity ranging from 15 to 40% by weight, or even from 20 to 30% by weight relative to the total weight of the composition.

[0145] Preferably, the composition comprises water and one or more organic solvents selected from C2-C6 alcohols, more preferably ethanol.

[0146] More preferably, the composition comprises water and ethanol.

[0147] Preferably, the composition comprises water and at least 10% by weight of one or more organic solvents, more preferably chosen from C2-C6 alcohols, and even more preferably from ethanol.

[0148] The water content may vary from 20 to 95% by weight, preferably from 40 to 90% by weight, preferably from 60 to 85% by weight, better from 70 to 80% by weight relative to the total weight of the composition.

[0149] Preferably, the composition comprises water and one or more organic solvents selected from C2-C6 alcohols, in particular ethanol; the organic solvent(s) being present in a content of at least 10% by weight, relative to the total weight of the composition, more preferably in a content ranging from 10 to 50% by weight, relative to the total weight of the composition.

[0150] The composition may optionally include further one or more additives such as those selected from cationic, anionic, amphoteric or zwitterionic surfactants and mixtures thereof, cationic, anionic, non-ionic, amphoteric polymers or mixtures thereof other than hydrophobic film-forming polymers and aqueous phase thickeners previously described, anti-dandruff agents, anti-seborrheic agents, vitamins and pro-vitamins including panthenol, sunscreens, sequestering agents, plasticizers, solubilizing agents, acidifying agents, opacifying or pearlescent agents, antioxidants, hydroxy acids, perfumes, preservatives and ceramides.

[0151] Of course, a person skilled in the art will take care to choose this or these possible complementary compounds in such a way that the advantageous properties intrinsically attached to the composition according to the invention are not, or substantially not, altered by the envisaged addition(s).

[0152] The above additives may generally be present in an amount of each of them between 0 and 20% by weight, relative to the total weight of the composition.

[0153] Cosmetic treatment process for keratinous materials

[0154] As previously stated, the invention also relates to a process for the cosmetic treatment of keratinous materials, preferably of skin and / or human keratinous fibers, such as hair, eyebrows and / or eyelashes, in particular hair, employing at least one mixture of glucose esters and fatty acids in Ci2-C22, as defined above, and / or at least one composition comprising at least one such mixture of glucose esters and fatty acids in Ci2-C22 as defined above.

[0155] The composition is as defined above.

[0156] The process according to the invention is preferably a cosmetic treatment process for keratinous materials, in particular hair, eyelashes, scalp, more preferably human hair and / or eyelashes, scalp in particular hair, scalp.

[0157] The process according to the invention preferably comprises at least the application on said fibers and / or on one or more areas of the skin of at least one mixture of glucose esters and C[2-C22] fatty acids, as defined above, and / or of at least one composition comprising at least one such mixture of glucose esters and C[2-C22] fatty acids as defined above.

[0158] The area or areas of the skin may or may be alopecic or not, preferably alopecic.

[0159] In other words, the area or areas of the skin may be one or more alopecic or non-alopecic areas of the human body.

[0160] The alopecic area of ​​the human body is preferably selected from the group consisting of an alopecic area of ​​the scalp, an area of ​​the face, in particular the beard, moustache or eyebrows, an area located on the free edge of the eyelids of human beings and / or any other alopecic area of ​​the human body.

[0161] Preferably, the alopecic area of ​​the human body is selected from the group consisting of an alopecic area of ​​the scalp, an area of ​​the face, in particular the beard, moustache or eyebrows and / or an area located on the free edge of the eyelids of human beings, more preferably an alopecic area of ​​the scalp and / or an area located on the free edge of the eyelids of human beings.

[0162] Preferably, the alopecic area of ​​the human body is an alopecic area of ​​the scalp, more preferably chosen from among the temporal temples, the frontal temples, the upper part of the occipital and / or the top of the skull.

[0163] The alopecic area of ​​the human body can be seen with the naked eye or by touch.

[0164] Thus the alopecic area of ​​the human body can be visible to the touch, that is to say that the area is covered with keratin fibers likely to be less dense to the touch.

[0165] The alopecic area may be partially or totally devoid of said fibers.

[0166] In particular, the treated alopecic area may be covered with finer and / or less pigmented keratin fibers, particularly finer, than non-alopecic areas.

[0167] The area or areas of skin may be one or more non-alopecic areas of the human body.

[0168] The non-alopecic area of ​​the human body is preferably selected from the group consisting of a non-alopecic area of ​​the scalp, an area of ​​the face, an area located on the free edge of the eyelids of human beings and / or any other area of ​​the human body.

[0169] The non-alopecic area of ​​the human body may be an area covered with keratin fibers that have been partially or totally shaved, an area pigmented differently from other areas of the human body, an area covered with undisciplined keratin fibers, or any other non-alopecic area of ​​the human body.

[0170] A non-alopecic area can also be an area of ​​skin covered by keratin fibers having a visual aesthetic appearance undesirable to the consumer.

[0171] Preferably, the non-alopecic area of ​​the human body is an area of ​​the scalp.

[0172] For the purposes of this invention, the term "non-alopecic zone" means a zone of the human body, in particular, an area of ​​skin not prone to alopecia.

[0173] Alopecia, which refers to the accelerated loss of hair, eyelashes, eyebrows and / or body hair, generally occurs in genetically predisposed individuals and primarily affects men. This is known as androgenetic alopecia, androgenic alopecia, or androgen-genetic alopecia.

[0174] Preferably, the process according to the invention is capable of cosmetically treating the loss, and / or slowing down the loss and / or promoting the regrowth, of keratin fibers as described above.

[0175] Preferably, the mixture or the glucose-derived O-acylated product, as defined above, or the composition as described above, can be applied to dry or moist keratinous materials, preferably moist, in particular alopecic areas.

[0176] Preferably, keratinous materials are washed before application of the composition as described above.

[0177] After application, the keratin materials are preferably left to dry, for example at a temperature ranging from 20°C to 40°C. Use

[0178] Similarly, the present invention relates to the use of at least one mixture of glucose esters and C12-C22 fatty acids, as defined above, and / or at least one composition comprising at least one such mixture of glucose esters and C12-C22 fatty acids, as defined above, for the cosmetic treatment of keratinous materials, in particular of the skin, especially the alopecic or non-alopecic area(s) of the skin, and / or human keratinous fibers such as hair, eyebrows, eyelashes and / or body hair.

[0179] Preferably, the use relates to the cosmetic treatment of human hair and / or eyelashes, of the scalp in particular of the hair, of the scalp.

[0180] More preferably, the use is intended to cosmetically treat the loss and / or promote the regrowth of said keratin fibers, preferably of hair and / or eyebrows, human eyelashes and / or body hair.

[0181] Preferably, the invention relates to the use of: - of at least one mixture of glucose and C12-C22 fatty acid esters comprising at least one glucose and linoleic acid monoester and at least one glucose and C12-C22 fatty acid monoester other than the glucose and linoleic acid monoester, and / or - of at least one composition comprising at least one glucose and linoleic acid monoester and at least one glucose and C12-C22 fatty acid monoester different from the glucose and linoleic acid monoester,

[0182] to cosmetically treat the loss and / or promote the regrowth of said keratin fibers, preferably of hair and / or eyebrows, human eyelashes and / or body hair.

[0183] The invention is illustrated in more detail in the following examples.

[0184] Examples: Enzymatic preparation of a mixture of glucose ester and vitamin F

[0185] Example 1: Mixture 2-methyl-2-butanol / dimethyl sulfoxide (DMSO) 75 / 25 mass / mass.

[0186] In a double-jacketed IL reactor equipped with a temperature probe, under mechanical stirring at 400 rpm, D-glucose (62.4 g) is solubilized in 158 mL (174 g) of dimethyl sulfoxide DMSO (boiling point = 189 °C) at a temperature of 65 °C.

[0187] After total solubilization of glucose, 146 g of vitamin F are added to the reactor followed by 679 mL (547 g) of 2-methyl-2-butanol (2M2B, boiling point = 102 °C) while maintaining the temperature of the reaction medium around 60 °C.

[0188] The enzyme sold under the trade name Novozym 435 or Lipozyme 435 (6.3 g) is then added to the reaction medium. The catalyst is an enzyme (lipase B from Candida antarctica) immobilized on acrylic resin beads; the enzyme is directly suspended in the reaction medium, followed by vacuum distillation of the dehydrated water / 2M2B mixture through an extemalized molecular sieve in a Soxhelt.

[0189] The mixture is kept under mechanical stirring at 400 rpm for a period of between 48 h and 70 h at a temperature between 50 °C and 65 °C such as 60°C+ / - 2 °C.

[0190] Once the reaction is complete, the reaction mixture is filtered and then: - either it has undergone one or more passes in what is called "short-path distillation" or "molecular distillation"; and / or - it has undergone one or more passes in distillation known as "scraped film" - either the 2M2B is evaporated at a temperature between 50 °C and 65 °C such as 60°C+ / - 2 °C under a reduced pressure between 100 and 150 mbars and the DMSO is evaporated under a pressure less than or equal to 3 mbars, at a temperature greater than or equal to 90 °C, preferably between 100 and 120 °C such as 115 °C.

[0191] After the addition of ethyl acetate, the residual DMSO and glucose from the reaction medium are extracted with water and then optionally the reaction medium is passed in one or more passes by so-called "short path" distillation and / or said medium is passed in one or more passes by so-called "scraped film" distillation.

[0192] The reaction medium is then carried out using a Dean Stark apparatus at atmospheric pressure, followed by distillation under reduced pressure. The mixture of the invention is then crystallized by the addition of a polar aprotic solvent such as acetone and then filtered. It is then re-pasted in said solvents and optionally recrystallized in a polar organic solvent such as acetone or even a mixture of organic solvents such as acetone / ethyl acetate. According to one embodiment, the mixture is between 50 / 50 acetone / ethyl acetate and 90 / 10 acetone / ethyl acetate, or even a mixture of organic solvents such as acetone and ethyl acetate, and then dried under vacuum (such as ≤ 20 mbar).

[0193] The glucose conversion rate is greater than 93% and the yield is greater than or equal to 45%. Example 2#: Dimethyl sulfoxide (DMSO)

[0194] In a 100 ml reactor equipped with a temperature probe, under electromagnetic stirring at 700 rpm, glucose (50g) is solubilized in 100 mL of dimethyl sulfoxide DMSO at a temperature of 60°C.

[0195] After total solubilization of glucose, 400 ml of vitamin F are added to the reactor while maintaining the temperature of the reaction medium around 60°C.

[0196] The enzyme sold under the trade name Novozym 435 (0.43g) is then added to the reaction medium.

[0197] The mixture is kept under magnetic stirring at 700 revolutions per minute for a period of 28 hours at a temperature of 60°C.

[0198] Once the reaction is complete, the reaction medium is filtered and then the dimethyl sulfoxide is evaporated at 60°C under a reduced pressure of 5 mbars.

[0199] The medium is gradually cooled to a temperature of 10°C in order to obtain the final product in powder form.

[0200] The conversion rate is 70% of glucose.

[0201] Example 3: Mixture of 2-methyl-2-butanol / aprotic polar organic solvent other than DMSO 75 / 25 mass / mass.

[0202] Example 3 was carried out following the experimental protocol of Example 1 and replacing the 75% 2M2B / 25% DMSO w / w mixture with 75% 2M2B / 25% aprotic polar organic solvent mixtures chosen from CPME (boiling point = 106 °C) and TBA (boiling point = 97 °C), w / w mixtures.

[0203] Thus the conversion rate obtained with the 2M2B / CPME mixture is 39% glucose, with the 2M2B / TBA mixture the conversion rate is 64% glucose.

Claims

Demands

1. A process for preparing at least one mixture of glucose and C12-C22 fatty acid esters comprising at least one esterification step of at least one C12-C22 fatty acid mixture and at least one glucose, carried out enzymatically in a medium comprising one or more polar organic solvent(s) having a boiling point at atmospheric pressure less than or equal to 200 °C

2. V-. A process according to claim 1, characterized in that the mixture of fatty acids in Ci2-C22 is a mixture of saturated and unsaturated fatty acids in C[2-C22, preferably a mixture of saturated and unsaturated fatty acids in Ci2-C20, even more preferably a mixture of saturated and unsaturated fatty acids in Ci2-Ci8.

3. A process according to claim 1 or 2, characterized in that the mixture of C[2-C22] fatty acids comprises at least linoleic acid and at least one C[2-C22] fatty acid other than linoleic acid, preferably selected from oleic acid, palmitic acid and stearic acid and mixtures thereof.

4. A process according to any one of the preceding claims, characterized in that the C[2-C22] fatty acid mixture comprises at least linoleic acid, at least oleic acid, at least palmitic acid and at least stearic acid, preferably the C[2-C22] fatty acid mixture is vitamin F.

5. A process according to any one of the preceding claims, characterized in that the mixture of glucose esters and C[2-C22] fatty acids is a mixture of glucose esters and C12-C20 fatty acids, preferably a mixture of glucose esters and C12-C18 fatty acids.

6. A process according to any one of the preceding claims, characterized in that the mixture of glucose and C[2-C22] fatty acid esters comprises at least one glucose and linoleic acid monoester and at least one glucose and C[2-C22] fatty acid monoester different from the glucose and linoleic acid monoester.

7. A process according to any one of the preceding claims, characterized in that the mixture of glucose esters and fatty acids in C12-C22 comprises, preferably consists of, a glucose and linoleic acid monoester (or glucose linoleate), a monoester of glucose and oleic acid (or glucose oleate), a monoester of glucose and palmitic acid (or glucose palmitate), and a monoester of stearic acid and glucose (or glucose stearate), and mixtures thereof.

8. A method according to any one of the preceding claims, characterized in that the enzyme(s) is (or are) selected from lipases, preferably from lipase B of Candida antarctica.

9. A process according to any one of the preceding claims, characterized in that the polar organic solvent(s) has a boiling point at atmospheric pressure between 50 °C and 195 °C, more particularly between 55 °C and 193 °C, preferably between 60 °C and 190 °C, more preferably between 75 °C and 189.5 °C, in particular between 100 °C and 189 °C.

10. A process according to any one of the preceding claims, characterized in that the polar organic solvent(s) is / are a mixture of at least two different solvents, at least one of which is a protic polar organic solvent, in particular selected from alcohols comprising one or more hydroxyl groups and comprising from 2 to 10 carbon atoms, in particular from 3 to 6 carbon atoms such as 2-methyl-2-butanol (2M2B);more preferably the polar organic solvent(s) with a boiling point at atmospheric pressure less than or equal to 200 °C, is / are a mixture of at least two solvents of which at least one is a protic polar organic solvent selected from alcohols comprising one or more hydroxy groups and comprising from 2 to 10 carbon atoms and the other is a polar aprotic organic solvent in particular selected from a di(Cr C6)alkyl sulfoxide such as DMSO, a heterocycloalkyl or cycloalkyl(Ci-C6)alkoxy such as CPME, or (Ci-C6)alkylcarbonyl(Ci-C6)alkoxy such as TBA, more preferably a di(Ci-C6)alkyl sulfoxide such as DMSO.;

11. A process according to any one of claims 1 to 10, characterized in that the polar organic solvent(s) comprises only one type of aprotic or protic polar organic solvent, preferably aprotic, in particular selected from a di(Ci-C6)alkyl sulfoxide such as DMSO, a heterocycloalkyl or a cycloalkyl(Ci-C6)alkoxy such as CPME, or (Ci-C6)alkylcarbonyl(Ci-C6)alkoxy such as TBA, more preferably a di(Ci-C6)alkylsulfoxide such as DMSO.

12. A process according to the preceding claim, characterized in that the polar organic solvent(s) is / are a mixture of at least two different solvents whose weight ratio of aprotic polar organic solvent / protic polar organic solvent varies from 5 / 95 to 40 / 60, preferably varies from 10 / 90 to 30 / 70, better varies from 15 / 85 to 25 / 75 such as 25 / 75.

13. A process according to any one of the preceding claims comprising at least one subsequent extraction purification step of one or more polar organic solvent(s) having a boiling point at atmospheric pressure less than or equal to 200 °C

14. V-. A process according to any one of the preceding claims characterized in that once the reaction is complete, the reaction medium (RM) is filtered and then: - either the RM is passed in one or more passes by so-called "short-path or molecular distillation"; and / or - the RM is passed in one or more passes by so-called "scraped film" distillation;- either the protic polar organic solvent(s) as defined above, preferably 2M2B is evaporated at a temperature between 50 °C and 65 °C such as 60 °C + / - 2 °C under a reduced pressure between 100 and 150 mbar and the aprotic polar organic solvent(s) as defined above, preferably chosen from a di(Ci-C6)alkyl sulfoxide such as DMSO, a heterocycloalkyl or cycloalkyl(CrC6)alkoxy such as CPME, or (Ci-C6)alkylcarbonyl(Ci-C6)alkoxy such as TBA, more preferably a di(Ci-C6)alkyl sulfoxide such as DMSO, the polar organic solvent(s) aprotic(s) is / are evaporated under a pressure less than or equal to 3 mbars, at a temperature greater than or equal to 90 °C, preferably between 100 and 120 °C such as 115 °C.;

15. A process according to any one of the preceding claims, characterized in that after the addition of the aprotic polar organic solvent(s), in particular ethyl acetate, residual DMSO and glucose from the reaction medium are extracted with water, and then optionally the reaction medium is subjected in one or more passes to so-called "short path" distillation and / or said medium is subjected in one or more passes to so-called "scraped film" distillation.

16. ». Mixture of glucose esters and Ci2-C22 fatty acids resulting from the esterification of at least one mixture of Ci2-C22 fatty acids and at least glucose, capable of being obtained by the preparation process as defined according to any one of the preceding claims.

17. A mixture of glucose and fatty acid esters in Ci2-C22, as defined in the preceding claim, comprises, preferably, i) a glucose and linoleic acid monoester (or glucose linoleate), ii) a glucose and oleic acid monoester (or glucose oleate), iii) a glucose and palmitic acid monoester (or glucose palmitate), and iv) a glucose and stearic acid monoester (or glucose stearate), capable of being obtained by the preparation process as defined in any one of claims 1 to 14;preferably the quantity by weight of i) is between 70 and 80% by weight such that 74% by weight, the quantity of ii) is between 10 and 20% by weight such that 15% by weight, the quantity of iii) is between 1 and 8% by weight such that 4% by weight, the quantity of iv) is between 0.5 and 5% by weight such that 3% by weight and v) from 0 to 3% by weight of saturated or unsaturated fatty acids comprising a number of carbon atoms greater than or equal to C20, it being understood that the sum of the quantity by weight of the mixture i)+ii)+iii)+iv) +v) represents 100.;

18. Composition, preferably cosmetic, comprising at least one mixture of glucose and fatty acids in Ci2-C22 as defined according to any one of claims 16 or 17.

19. Use of at least one mixture of glucose esters and C[2-C22] fatty acids, as defined according to any one of claims 16 or 17, and / or at least one composition as defined according to the preceding claim, for the treatment cosmetics of keratinous materials, in particular of the skin, including the alopecic or non-alopecic area(s) of the skin, and / or human keratinous fibers such as hair, eyebrows, human eyelashes and / or body hair.

20. A process for the cosmetic treatment of keratinous materials, preferably human skin and / or keratinous fibers, such as hair, eyebrows and / or eyelashes, in particular hair, employing on said keratinous materials at least one mixture of glucose esters and fatty acids in Ci2-C22, as defined in any one of claims 16 or 17, and / or at least one composition as defined in claim 18.

21. A method according to the preceding claim, for cosmetically treating the loss, and / or slowing down the loss and / or promoting regrowth, of keratin fibers such as hair, eyebrows, human eyelashes and / or body hair.