Purification method for one or more cosmetic ingredients by at least one electrodialysis

Abstract

The present invention relates to a method for purifying (PU) at least one aqueous medium based on at least one C-glycoside derivative corresponding to formula (I) (preferably corresponding to formula (I') or (I''), and optical or geometric isomers thereof, and / or solvates (e.g., hydrates) thereof, and at least one salt, comprising at least one step of electrodialysis (PU1) of the aqueous medium. The present invention also relates to a method for preparing (PR) at least one C-glycoside derivative as described herein, comprising at least one step of electrodialysis (PU) of at least one aqueous medium containing at least the C-glycoside derivative and at least one salt. JPEG2026518301000030.jpg41170

Description

Technical Field

[0001] The present invention relates to a method for purifying (PU) at least one aqueous medium based on at least one cosmetic ingredient, in particular at least one C-glycoside derivative corresponding to formula (I) described below, preferably corresponding to formula (I') or (I''), and its optical isomers or geometric isomers, and / or its solvate (e.g., hydrate) and at least one salt, the method comprising at least one step (PU1) of electrodialysis of the aqueous medium.

[0002] The present invention also relates to a method for preparing (PR) at least one cosmetic ingredient, in particular at least one C-glycoside derivative described below, the method comprising at least one step (PU) of purification by electrodialysis of at least one aqueous medium comprising at least said cosmetic ingredient, in particular at least one C-glycoside derivative and at least one salt.

Background Art

[0003] For example, methods for preparing water-soluble organic components having advantageous cosmetic properties on keratinous substances can result in the formation of one or more impurities in ionic form, which has been found to be generally cumbersome to minimize or remove without affecting the yield of the cosmetic ingredient being synthesized to some extent.

[0004] Furthermore, when such impurities are present with the final cosmetic ingredient, they can cause undesirable color, texture changes, or odors in the cosmetic composition using the ingredient. Therefore, such impurities can cause unpleasant and prominent odors, such as those of pungent and strong vinegar, and tend to manifest even after performing one or more purification operations, and have been found to be inconvenient and persistent even after formulation for consumers, and this tendency is increasing, because the current trend is to use fewer and fewer fragrances in cosmetics to hide or neutralize such odors.

[0005] Such impurities can also cause problems of compatibility with other additives optionally present in the final cosmetic formulation.

[0006] Such impurities can also be salts of acids or bases that will affect the pH in the aqueous medium. This effect is even more troublesome because the cosmetic active agent is isolated in the form of a concentrated aqueous solution.

[0007] In addition, the presence of such impurities, specifically inorganic and / or organic salts, can induce a significant increase in the viscosity of the aqueous reaction medium containing the cosmetic components, and thus, in some cases, it becomes difficult to obtain a concentrated solution of the cosmetic components intended for formulation.

[0008] As an example, C-glycoside derivatives are water-soluble organic compounds, and their properties are generally advantageous for use in stimulating the synthesis of glycosaminoglycans present in the dermis in the field of cosmetics, specifically in care compositions, specifically for imparting density and firmness to the skin (see, for example, (Non-Patent Document 1)).

[0009] C-glycoside derivatives such as xylose C-glycoside derivatives are generally synthesized from unprotected monosaccharides or polysaccharides (such as D-xylose and β-dicarbonyl compounds such as acetylacetone) in an aqueous medium in the presence of an alkaline agent by a reaction known as the Lubineau reaction (Non-Patent Document 2).

[0010] The Lubineau reaction is carried out using at least one alkaline agent (such as sodium bicarbonate or sodium hydroxide) present in an equimolar amount or in excess with respect to the monosaccharide or polysaccharide, preferably in excess, and depending on the nature of this alkaline agent, and / or depending on reaction parameters such as concentration and / or temperature, over a reaction time that can vary from 5 minutes to 20 hours.

[0011] However, such synthesis reactions exhibit a major pitfall: the formation of impurities, specifically in the form of salts, such as organic salts like sodium acetate, which can be very significant and difficult to reduce even by performing some conventional purification and / or washing operations.

[0012] At the end of this reaction, the aqueous reaction medium may be neutralized with at least one inorganic acidifying agent (especially hydrochloric acid) to convert the organic acid salt to an organic acid, specifically by converting sodium acetate to acetic acid, and then several cycles of water addition and distillation may be carried out to reduce the amount of organic acid to a commercially acceptable level.

[0013] However, neutralization of the reaction medium with at least one inorganic acidifying agent, such as hydrochloric acid, also results in the formation of a salt (specifically sodium chloride), which can be removed by precipitation with the addition of a water-miscible solvent, such as alcohol (specifically isobutanol or ethanol). To do this, a continuous distillation operation (specifically, a continuous distillation operation to remove water), followed by the addition of alcohol, can induce the crystallization of the salt, and then an optional washing operation can be performed, in which the amount of salt is reduced to an acceptable level in commercially available solutions intended for use in the cosmetic field by the addition of water in several cycles.

[0014] At the end of these various washing and / or purification operations, the resulting C-glycoside derivative may be pure and solvent-free, and subsequently, optionally, subjected to a hydrogenation reaction targeting the reduction of ketone functional groups in the C-glycoside derivative obtained from the β-dicarbonyl derivative to confer hydroxyl functional groups.

[0015] Specifically, cosmetic ingredients, particularly xylose C-glycoside derivatives such as β-D-xylopyranoside-n-propan-2-one, are subsequently subjected to a reduction reaction to obtain C-β-D-xylopyranoside-2-hydroxypropane.

[0016] However, washing and / or purification operations, including those performed several times in succession, cannot satisfactorily reduce the amount of ionic impurities generated during the synthesis process and / or impurities arising from ionic forms, especially on an industrial scale.

[0017] Specifically, such washing and / or purification operations have the disadvantage of having to be performed several times to sufficiently reduce the amount of impurities, and, if the impurities are foul-smelling, to minimize the odor caused by certain impurities such as acetic acid, which are unpleasant and should be avoided in cosmetic use.

[0018] Therefore, the continuous execution of these purification and / or washing operations has disadvantages, such as reduced yield, generation of additional organic wastewater, increased number of steps, and / or being cumbersome to carry out industrially, due to the need to reduce the content of organic acids (specifically acetic acid) and salts (e.g., sodium chloride) in the final cosmetic ingredients intended for cosmetic formulation for cosmetic use.

[0019] Furthermore, the use of organic solvents (specifically (non)polar aprotic organic solvents) during washing operations often has the disadvantage of not adequately reducing impurities, and also leads to additional washing or neutralization operations, in fact purification by chromatography and / or crystallization, which can negatively affect the yield. Such additional operations are also cumbersome to perform on an industrial scale. In addition, residual organic solvent content may remain in the solution of cosmetic ingredients used in the final cosmetic formulation, which is undesirable.

[0020] Furthermore, similar drawbacks to those described above have been found when it is desirable to reduce, or even minimize, the salt content in aqueous formulations based on one or more cosmetic ingredients (specifically, one or more C-glycoside derivatives).

[0021] As a result, conventional washing and / or purification operations performed to reduce the salt content in a medium containing at least one C-glycoside derivative do not yield satisfactory results for industrial-scale production that is specifically reproducible and robust, particularly in terms of yield and purity, for use in the cosmetic field. [Prior art documents] [Non-patent literature]

[0022] [Non-Patent Document 1] “Synthesis of Pro-XylaneTM: A new biologically active C-glycoside in aqueous media”, M. Dalko-Csiba et al., Bioorganic & Medicinal Chemistry Letters, 19(2009), 845-849 [Non-Patent Document 2] Rodrigues, F., Canac, Y. and Lubineau, A., A convenient, one-step, synthesis of β-C-glycosidic ketones in aqueous media, Chemical Communications, 2000(20), 2049-2050 [Overview of the Initiative] [Problems that the invention aims to solve]

[0023] There is a need for improved, industrially viable methods for separating and recovering C-glycoside derivatives from aqueous compositions.

[0024] Therefore, taking the above into consideration, it is actually necessary to adopt a novel method for purifying at least one aqueous medium comprising at least one cosmetic ingredient (particularly at least one C-glycoside derivative) and at least one salt, which does not exhibit the aforementioned drawbacks and specifically results in improved purity and higher yield, and its implementation is more optimized, especially industrially, in terms of product quality on an industrial scale, the number of purification steps, implementation, and / or the organic waste liquid generated.

[0025] In other words, one of the objectives of the present invention is to provide a method for processing at least one aqueous medium containing at least one cosmetic ingredient (particularly at least one C-glycoside derivative) and at least one salt on an industrial scale for cosmetic applications.

[0026] Specifically, one of the objectives of the present invention is to provide a method for preparing one or more cosmetic ingredients (particularly one or more C-glycoside derivatives) that minimizes impurities, including those that may produce unpleasant or offensive odors (for example, specifically irritating and strong vinegar-like odors resulting from the synthesis process), so that it can be efficiently carried out on an industrial scale for cosmetic applications.

[0027] Another object of the present invention is to provide a method for separating and recovering free acids generated during the synthesis of cosmetic components (particularly C-glycoside derivatives) in an aqueous solution containing at least one salt (particularly at least one acetate). [Means for solving the problem]

[0028] Therefore, one subject of the present invention is a method for purifying (PU) at least one aqueous medium, wherein the aqueous medium is - At least one cosmetic ingredient, in particular, formula (I) below [ka] It is at least one compound of the following: In formula (I), - SA' represents a monosaccharide or polysaccharide group containing up to 20 sugar units of the pyranose and / or furanose type, and of the L and / or D series, specifically up to 6 sugar units, preferably representing a monosaccharide, disaccharide, or trisaccharide, more preferably representing a monosaccharide, and the monosaccharide or polysaccharide group is substituted with at least one free hydroxyl group and optionally, optionally protected, at least one amine group optionally protected with an acetyl group R'-C(Y)-(R' represents a hydrogen atom or an (C1-C6) alkyl group, e.g., methyl, and Y represents O or S, preferably representing O). - The bond between SA' and -CH2X is a C-anomeric bond. - X represents a divalent group, -C(O)- or -CH(OR)-. - R is a hydrogen atom, C1~C 10 The alkyl group, preferably a C1-C4 alkyl group, such as methyl, or a (C1-C4) alkylcarbonyl group, such as acetyl, preferably represents a hydrogen atom. - R1 is saturated or unsaturated, linear or branched, cyclic or acyclic, preferably acyclic C1-C 10 This represents a hydrocarbon chain, preferably a C1-C4 hydrocarbon chain, which is more preferably saturated. compound, and one of the optical or geometric isomers of this compound, and / or one of the solvates of this compound, such as the hydrate, - At least one type of salt and Includes The method comprises at least one step (PU1) of electrodialysis of the aqueous medium.

[0029] Therefore, the purification method (PU) according to the present invention makes it possible to efficiently reduce the amount of salt and / or the conjugate acid form of the salt that exists as a mixture with at least one cosmetic component (specifically, at least one compound of formula (I)) in an aqueous medium.

[0030] This salt may result from at least one step of preparing the cosmetic ingredient, and / or from one or more washing and / or one or more neutralizing steps performed after at least one step of the method for preparing the cosmetic ingredient.

[0031] Therefore, the purification method (PU) according to the present invention makes it possible to efficiently reduce the amount of salt present in an aqueous medium as a mixture with at least one cosmetic component (in particular, at least one compound of formula (I)).

[0032] This salt may result from at least one step of preparing the cosmetic ingredient, and / or from one or more washing and / or one or more neutralizing steps performed after at least one step of the method for preparing the cosmetic ingredient.

[0033] Salts present in an aqueous medium may arise from at least one step of a method for preparing at least one cosmetic ingredient (particularly at least one compound of formula (I)), and / or from one or more washing and / or one or more neutralizing steps performed after at least one step of a method for preparing a cosmetic ingredient (particularly a method for preparing a compound of formula (I)).

[0034] Salts present in an aqueous medium can also arise from additions to the aqueous medium. Specifically, this may involve the addition of mineral acids, such as hydrogen halides, particularly hydrochloric acid, sulfonic acid, and carboxylic acids, such as acetic acid.

[0035] In other words, the purification method (PU) according to the present invention makes it possible to process any aqueous medium containing at least one cosmetic component (particularly at least one compound of formula (I)) and at least one salt, which may or may not be an impurity, for at least one cosmetic use, preferably for cosmetic use for the care of keratinous substances such as skin.

[0036] This purification method (PU) advantageously reduces the presence of at least one salt (which may or may not be an impurity) in the aqueous medium without significantly affecting the quality and / or purity of the cosmetic ingredients.

[0037] This purification method (PU) advantageously reduces the presence of at least one salt (which may or may not be an impurity) in the aqueous medium without significantly affecting the quality and / or purity of the compound of formula (I).

[0038] Specifically, this purification method (PU) makes it possible to significantly reduce the content of one or more ionic impurities (for example, those that are sources of unpleasant odors) that exist as a mixture with at least one compound of formula (I) in an aqueous medium.

[0039] This purification method (PU) further facilitates the preparation of commercially available solutions based on at least one cosmetic ingredient (specifically, at least one compound of formula (I)) for at least one cosmetic use, preferably for cosmetic use for the care of keratinous substances such as skin.

[0040] The purification method (PU) according to the present invention may be carried out after one or more steps of synthesizing at least one cosmetic ingredient (specifically, at least one compound of formula (I)), and / or after at least one step of washing and / or neutralizing an aqueous reaction medium containing at least one compound of formula (I).

[0041] Therefore, the purification method (PU) according to the present invention may be performed during the preparation process of one or more cosmetic ingredients preferably selected from the compounds of formula (I), for example, at the end of the preparation process, or after one of the steps of the process, for example, between steps of the process.

[0042] In addition, another object of the present invention is to provide a method for preparing (PR) one or more cosmetic ingredients preferably selected from compounds of formula (I), comprising at least one purification (PU) step (PU1) of electrodialysis of at least one aqueous medium containing at least one salt of the cosmetic ingredient (preferably a compound of formula (I)).

[0043] In other words, the present invention relates to a method for preparing (PR) one or more cosmetic ingredients preferably selected from compounds of formula (I), comprising at least one purification (PU) of subjecting at least one aqueous medium containing at least one cosmetic ingredient and at least one salt, preferably selected from compounds of formula (I), to at least one electrodialysis (PU1).

[0044] To put it another way, the present invention specifically relates to a method for preparing (PR) one or more cosmetic ingredients, preferably selected from compounds of formula (I), - At least one step (PRi) is performed in which at least one cosmetic component is synthesized, preferably selected from at least one compound of formula (I), and at least one salt of the cosmetic component (preferably the compound of formula (I)) is formed in an aqueous medium. 〇 Optionally, at least one washing and / or neutralizing step (PR0), preferably at least one step (PR0) to neutralize the aqueous reaction medium obtained from at least one of the synthesis steps (PRi), - At least one purification (PU) comprising at least one step (PU1) of electrodialysis of an aqueous reaction medium, which is at least the aqueous reaction medium and preferably contains at least the cosmetic component selected from compounds of formula (I) and at least one salt. Regarding methods including

[0045] According to a preferred embodiment, the present invention specifically relates to a method for preparing (PR) one or more compounds of formula (I), - At least one step (PRi) of synthesizing at least one compound of formula (I), and forming at least one compound of formula (I) and at least one salt in an aqueous medium, 〇 Optionally, at least one washing and / or neutralizing step (PR0), preferably at least one step (PR0) to neutralize the aqueous reaction medium obtained from at least one of the synthesis steps (PRi), - At least one purification (PU) comprising at least one step (PU1) of electrodialysis of at least the aqueous reaction medium containing at least the compound of formula (I) and at least the salt. Regarding methods including

[0046] Therefore, the preparation method (PR) according to the present invention makes it possible to achieve the above-mentioned objectives, namely, to obtain one or more cosmetic components preferably selected from compounds of formula (I) that have high purity in sufficient yield and exhibit particularly robust and reproducible optimized industrial-scale execution compared to processes conventionally employed in the prior art.

[0047] Specifically, the preparation method (PR) according to the present invention has the advantage of minimizing impurities in ionic and / or nonionic conjugated forms (for example, those that typically produce a pronounced and unpleasant odor, such as a pungent and strong vinegar-like smell), which are particularly time-consuming and difficult to remove by conventional washing and / or purification operations.

[0048] Specifically, the preparation method (PR) according to the present invention has the advantage of minimizing impurities in ionic form (e.g., their acidic form), which are particularly time-consuming and difficult to remove by conventional washing and / or purification operations (e.g., those that typically produce a pronounced and unpleasant odor, such as a pungent and strong vinegar-like smell).

[0049] This electrodialysis process (PU1) is advantageous in that it is possible to remove very large amounts of ionic impurities resulting from at least one synthesis process (PRi) and optionally from at least one neutralization process (PR0) performed using at least one inorganic or organic acidifying agent (preferably an organic acidifying agent).

[0050] The electrodialysis process (PU1) also advantageously allows for the removal of very large amounts of impurities in ionic and / or nonionic conjugated forms (e.g., their acidic form) arising from at least one synthesis process (PRi) and at least one neutralization process (PR0) which is optionally performed using at least one inorganic or organic acidifying agent (preferably an organic acidifying agent).

[0051] Subsequently, the method (PR) according to the present invention advantageously makes it possible to reduce the amount of fragrance that may be used to mask or neutralize unpleasant odors during the preparation of a cosmetic formulation based on at least one cosmetic ingredient (preferably a compound of formula (I)), and / or increase the range of such fragrances.

[0052] The method (PR) according to the present invention can efficiently reduce organic wastewater at the reactor outlet and can also limit the numerous solvent exchange and / or washing operations that are conventionally performed by the methods described in the prior art.

[0053] Specifically, the method (PR) according to the present invention is industrially more easily optimizable than conventional prior art methods (specifically, those involving several successive distillations to reduce ionic impurities as much as possible), thereby enabling the synthesis reaction to be processed in the same reactor having a format suitable for the batch being processed, and also enabling the purification and / or washing process to be processed.

[0054] The electrodialysis process (PU1) makes it possible to carry out the method according to the present invention in any reactor, thereby making the method according to the present invention industrially versatile and flexible.

[0055] Specifically, the step (PR1) of synthesizing the compound of formula (I) can be carried out in any reactor.

[0056] The method (PR) according to the present invention also has the advantage of not using organic solvents to reduce impurities arising from at least one of the synthesis steps, thereby improving its environmental footprint.

[0057] Therefore, the preparation method (PR) according to the present invention makes it possible to save the number of steps performed at the end of the synthesis reaction in order to reduce the content of impurities, facilitates the implementation of additional reactions of cosmetic ingredients at an industrial level, for example, facilitating the implementation of additional reactions (e.g., a step of reducing the compound of formula (I)) performed in a method for preparing cosmetic ingredients (specifically, the compound of formula (I)).

[0058] The preparation method (PR) according to the present invention also has the advantage of efficiently yielding several grades of cosmetic ingredients depending on the desired content of impurities resulting from the use of electrodialysis.

[0059] Therefore, the preparation method (PR) according to the present invention also has the advantage of efficiently yielding several grades of cosmetic ingredients (particularly compounds of formula (I)) depending on the desired content of impurities resulting from the use of electrodialysis.

[0060] Therefore, the preparation method (PR) according to the present invention makes it easier to control the content of impurities in the final solution intended for cosmetic use.

[0061] Other subjects, characteristics, aspects, and advantages of the present invention will become clearer by reading the following description and examples. [Modes for carrying out the invention]

[0062] In the text below, unless otherwise specified, boundary values ​​of a range are included in that range, especially in expressions such as "between ~" and "from ~ to ~".

[0063] Furthermore, the expression "at least one" used in this explanation is equivalent to the expression "one or more."

[0064] In addition, the expression "at least" used in this explanation is equivalent to the expression "greater than or equal to". Finally, in its own known sense, "C n A "Cn" compound or group refers to a compound or group that contains "n" carbon atoms in its chemical structure.

[0065] For the purposes of this invention, the term "cosmetic ingredient" is equivalent to "cosmetic surfactant" and refers to any compound having the desired activity in the field of beauty, for example, surfactants that have a biological effect after application to keratinous substances (e.g., non-therapeutic surfactants intended to prevent or treat signs of aging, such as moisturizing creams and moisturizers; surfactants that have an effect on barrier function, such as UV shielding agents; and / or any compound that alters the appearance of keratinous substances, such as colorants).

[0066] For the purposes of this invention, keratin material is understood to mean skin of the body, hands, legs, face, and décolleté, as well as skin, preferably hair, and more preferably skin, such as keratin fibers.

[0067] Within the scope of the present invention, the terms "purification (P)" and "purification process (P)" are used without distinction.

[0068] Within the scope of the present invention, the terms "alkaline agent" and "basicizing agent" are used without distinction.

[0069] The basicizing agent may be an inorganic alkaline agent, preferably an inorganic alkaline agent selected from the group consisting of alkali metal hydroxides or alkaline earth metal hydroxides, such as lithium hydroxide, sodium hydroxide, potassium hydroxide, alkali metal or alkaline earth metal (bi)carbonates, such as sodium (bi)carbonate or potassium, and mixtures thereof. The basicizing agent may be an organic alkali agent, preferably selected from the group consisting of mono(C1-C6)(hydroxy)alkylamines, di(C1-C6)(hydroxy)alkylamines, tri(C1-C6)(hydroxy)alkylamines (preferably tri(C1-C6)(hydroxy)alkylamines), aromatic saturated or unsaturated cyclic amines, such as pyridine, or non-aromatic substances optionally substituted with one or more (C1-C4) alkyl groups, such as tetrahydropyridine optionally substituted with one or more (C1-C4) alkyl groups, piperidine optionally substituted with one or more (C1-C4) alkyl groups, or piperazine optionally substituted with one or more (C1-C4) alkyl groups. Preferably, the alkali agent of the present invention is a tertiary amine.

[0070] Preferably, the basicizing agent is selected from the group consisting of alkali metal or alkaline earth metal hydroxides, specifically sodium hydroxide; alkali metal or alkaline earth metal (bi)carbonates, specifically sodium (bi)carbonate or potassium; and tri(C1-C6)(hydroxy)alkylamines, specifically tri(C1-C6)alkylamines, particularly triethylamine.

[0071] Preferably, the basicizing agent is inorganic.

[0072] More preferably, the basicizing agent is selected from the group consisting of inorganic alkali metal or alkaline earth metal hydroxides, alkali metal or alkaline earth metal (bi)carbonates, and mixtures thereof, specifically alkali metal or alkaline earth metal hydroxides, specifically sodium hydroxide.

[0073] The acidifying agent that can be used in the method according to the present invention can be any acidifying means known to those skilled in the art, for example, the use of an acidic resin, or the addition of an organic or inorganic acidifying agent (preferably an inorganic acidifying agent).

[0074] The acidifying agent can be inorganic, for example, sulfuric acid, phosphoric acid, sulfonic acid, or phosphonic acid, H + Hal - hydrohalic acid (Hal represents a halogen atom selected from the group consisting of chlorine, bromine, and iodine), preferably H + Hal - acid (Hal preferably represents a chlorine atom); preferably by the addition of an inorganic acidifying agent, specifically, an inorganic acid type, for example, sulfuric acid, phosphoric acid, sulfonic acid, or phosphonic acid, H + Hal - acid (Hal represents a halogen atom selected from the group consisting of chlorine, bromine, and iodine), preferably H + Hal - acid (Hal preferably represents a chlorine atom).

[0075] The organic acidifying agent can be selected from the group consisting of i) carboxylic acids, specifically (poly)hydroxy(C1-C6)alkyl(poly)carboxylic acids, such as acetic acid, tartaric acid, citric acid, and lactic acid, and ii) sulfonic acids, specifically (C1-C6)alkylsulfonic acids.

[0076] Purification method (PU) As shown above, the purification method (PU) is carried out in an aqueous medium containing at least one cosmetic ingredient (preferably at least one compound of formula (I)) and at least one salt.

[0077] In other words, the method (PU) is a treatment method by electrodialysis of at least one aqueous medium containing at least one cosmetic ingredient (preferably at least one compound of formula (I)) and at least one salt.

[0078] Therefore, the method (PU) makes it possible to process an aqueous solution containing at least one cosmetic ingredient (preferably at least one compound of formula (I)) and at least one salt.

[0079] aqueous medium The aqueous medium to be treated contains at least one cosmetic ingredient and at least one salt.

[0080] Preferably, the aqueous medium comprises at least one compound of formula (I) and at least one salt.

[0081] As shown above, the compound of formula (I) is the following formula (I): [ka] It supports, In formula (I), - SA' represents a monosaccharide or polysaccharide group containing up to 20 sugar units of the pyranose and / or furanose type, and of the L and / or D series, specifically up to 6 sugar units, preferably representing a monosaccharide, disaccharide, or trisaccharide, more preferably representing a monosaccharide, wherein the monosaccharide or polysaccharide is substituted with at least one free hydroxyl group and at least one amine group that is optionally protected, specifically an acetyl group R'-C(Y)-(R' represents a hydrogen atom or an (C1-C6) alkyl group, e.g., methyl, and Y represents O or S, preferably O). - The bond between SA' and -CH2X is a C-anomeric bond. - X represents a divalent group selected from -C(O)- or -CH(OR)-, - R is a hydrogen atom, C1~C 10 The alkyl group, preferably a C1-C4 alkyl group, such as methyl, or a (C1-C4) alkylcarbonyl group, such as acetyl, preferably represents a hydrogen atom. - R1 is saturated or unsaturated, linear or branched, cyclic or acyclic, preferably acyclic C1-C 10 This represents a hydrocarbon chain, preferably a C1-C6 hydrocarbon chain, more preferably a C1-C4 hydrocarbon chain, specifically a C1 hydrocarbon chain, which is more preferably saturated. This also corresponds to one of the optical or geometric isomers of formula (I), and / or one of the solvates of formula (I), such as the hydrate.

[0082] The phrases "C-anomeric bond" and "bond between SA' and CH2-X" are understood to mean that a portion of the sugar part SA' is connected to the rest of the molecule via the methylene group-CH2-, not by an oxygen-carbon OC bond (i.e., not by the carbon bond of the oxygen-methylene-CH2- of the sugar SA'), but by a carbon-carbon CC bond (i.e., the carbon of the carbon-methylene-CH2- of the sugar SA').

[0083] Within the scope of the present invention, SA' comprises a monosaccharide or polysaccharide SA group containing up to 20 sugar units as defined above, wherein SA is substituted with at least one free hydroxyl group.

[0084] In other words, SA' has the same meaning as SA and contains at least one free hydroxyl group (-OH).

[0085] SA' may represent a monosaccharide or polysaccharide group comprising up to 20 sugar units of the α or β anomeric, pyranose and / or furanose type, and L and / or D series, specifically comprising up to 6 sugar units, wherein the monosaccharide or polysaccharide comprises at least one free hydroxyl group and optionally at least one optionally protected amine group.

[0086] According to one embodiment, SA' is a monosaccharide group selected from the group consisting of glucose, galactose, mannose, xylose, fucose, arabinose, rhamnose, glucuronic acid, galacturonic acid, iduronic acid, N-acetylglucosamine, and N-acetylgalactosamine. More specifically, SA is a monosaccharide selected from the group consisting of D-glucose, D-galactose, D-mannose, D-xylose, L-fucose, L-arabinose, L-rhamnose, D-glucuronic acid, D-galacturonic acid, D-iduronic acid, N-acetyl-D-glucosamine, and N-acetyl-D-galactosamine.

[0087] Preferably, SA' is a monosaccharide selected from the group consisting of glucose, xylose, N-acetylgalactosamine, and fucose, more specifically, a monosaccharide selected from the group consisting of glucose, xylose, and fucose, and more specifically, xylose.

[0088] More preferably, SA' is a monosaccharide group selected from the group consisting of D-glucose, D-xylose, N-acetyl-D-galactosamine, and L-fucose, more specifically a monosaccharide group selected from the group consisting of D-glucose, D-xylose, and L-fucose, and more specifically D-xylose.

[0089] According to one embodiment, SA' is an oligosaccharide comprising a polysaccharide group selected from the group consisting of up to six sucrose units and composed of D-maltose, D-lactose, D-cellobiose, and D-maltotriose; a disaccharide combining a uronic acid selected from D-iduronic acid or D-glucuronic acid with a hexosamine selected from D-galactosamine, D-glucosamine, N-acetyl-D-galactosamine, or N-acetyl-D-glucosamine; and two xylose molecules linked via a 1,4 bond, comprising at least one xylose (preferably xylobiose) favorably selected from xylobiose, methyl β-xylobioside, xylotriose, xylotetrose, xylopentose, and xylohexose.

[0090] Preferably, SA' represents a monosaccharide group.

[0091] Preferably, SA' represents a monosaccharide group selected from the group consisting of glucose, specifically D-glucose; xylose, specifically D-xylose; fucose, specifically L-fucose; arabinose, specifically L-arabinose; rhamnose, specifically L-rhamnose; glucuronic acid, specifically D-glucuronic acid; galacturonic acid, specifically D-galacturonic acid; iduronic acid, specifically D-iduronic acid; N-acetylglucosamine, specifically N-acetyl-D-glucosamine; and N-acetylgalactosamine, specifically N-acetyl-D-galactosamine. Preferably, SA is selected from D-glucose, D-xylose, L-fucose, L-arabinose, L-rhamnose, D-glucuronic acid, D-galacturonic acid, or D-iduronic acid.

[0092] Preferably, SA' represents a monosaccharide group selected from the group consisting of glucose, xylose, N-acetylgalactosamine, and fucose, and more preferably, SA' is selected from the group consisting of glucose, xylose, and fucose.

[0093] Preferably, SA' represents a monosaccharide group selected from the group consisting of D-glucose, D-xylose, N-acetyl-D-galactosamine, and L-fucose, and more preferably, SA' is selected from the group consisting of D-glucose, D-xylose, and L-fucose.

[0094] More preferably, SA' represents a xylose group, and even more preferably, D-xylose.

[0095] As shown above, R1 is linear or branched, saturated or unsaturated, cyclic or acyclic C1-C 10 This represents a hydrocarbon chain, preferably a C1-C6 hydrocarbon chain, more preferably a C1-C4 hydrocarbon chain, and specifically a C1 hydrocarbon chain.

[0096] According to one embodiment, R1 represents a linear or branched, saturated or unsaturated, cyclic or acyclic, preferably acyclic C1-C6 hydrocarbon chain, more preferably a C1-C4 hydrocarbon chain, specifically a C1 hydrocarbon chain.

[0097] According to one embodiment, R1 represents a linear or branched, saturated or unsaturated, preferably unsaturated, cyclic, for example, cyclohexyl or cyclopentyl, or acyclic C1-C6 alkyl chain, more preferably a C1-C4 alkyl chain, specifically a C1 alkyl chain.

[0098] Preferably, R1 is linear or branched, preferably linear, saturated or unsaturated, preferably saturated, acyclic C1-C 10 This represents a hydrocarbon chain, preferably a C1-C6 hydrocarbon chain, more preferably a C1-C4 hydrocarbon chain, and specifically a C1 hydrocarbon chain.

[0099] Preferably, R1 is a linear, saturated or unsaturated, preferably saturated, acyclic C1-C1. 10This represents an alkyl chain, preferably a C1-C6 alkyl chain, more preferably a C1-C4 alkyl chain, and specifically a C1 alkyl chain.

[0100] Primarily, R1 represents a linear, saturated or unsaturated, acyclic C1-C4 alkyl chain, specifically a C1 alkyl chain.

[0101] Preferably, X represents a divalent group, either -C(O)- or -CH(OH)-.

[0102] For advantage, in equation (I), - X represents a divalent group, either -C(O)- or -CH(OH)-. - SA represents a monosaccharide group selected from the group consisting of D-glucose, D-galactose, D-mannose, D-xylose, L-fucose, L-arabinose, L-rhamnose, D-glucuronic acid, D-galacturonic acid, D-iduronic acid, N-acetyl-D-glucosamine, and N-acetyl-D-galactosamine, preferably a monosaccharide group selected from D-glucose, D-galactose, D-mannose, D-xylose, L-fucose, L-arabinose, L-rhamnose, D-glucuronic acid, D-galacturonic acid, or D-iduronic acid, and more preferably a monosaccharide group selected from D-glucose, D-xylose, or L-fucose. - R1 is a linear, saturated or unsaturated, preferably saturated, acyclic C1-C 10 The term represents a hydrocarbon chain, preferably a C1-C6 hydrocarbon chain, more preferably a C1-C4 hydrocarbon chain, and specifically a methyl group.

[0103] Preferably, the compound of formula (I) is of the following formula (I'): [ka] A compound that corresponds to, In formula (I'), - n is equal to 0 or 1, preferably equal to 1. - p is a various integer from 1 to 4, preferably the subscript p is equal to 3. - R1 has the same meaning as formula (I), and is preferably linear, preferably acyclic C1-C 10 This represents an alkyl chain, preferably a C1-C6 alkyl chain, more preferably a C1-C4 alkyl chain, and specifically a C1 alkyl chain. - X represents a divalent group, -C(O)- or -CH(OR)-. - R is a hydrogen atom, C1~C 10 The R represents an alkyl group, preferably a C1-C4 alkyl group, such as methyl, or a (C1-C4) alkylcarbonyl group, such as acetyl, and preferably, R represents a hydrogen atom. compound and one of the optical or geometric isomers of this compound, and / or one of the solvates of this compound, such as the hydrate. That is the case.

[0104] In other words, the compound of formula (I) is preferably selected from the group consisting of the compound of formula (I'), one of its optical or geometric isomers, and / or one of its solvates, such as a hydrate, and mixtures thereof.

[0105] Preferably, in formula (I'), the subscript n is equal to 1, and the subscript p is a various integer from 1 to 4, preferably the subscript p is equal to 3.

[0106] Preferably, the compound of formula (I) is the following formula (I''): [ka] A compound that corresponds to, In the formula (I''), - R1 has the same meaning as formula (I), and is preferably linear, preferably acyclic C1-C 10This represents an alkyl chain, preferably a C1-C6 alkyl chain, more preferably a C1-C4 alkyl chain, and specifically a C1 alkyl chain. - X represents a divalent group -C(O)- or -CH(OR)-, preferably -C(O)-. - R is a hydrogen atom, C1~C 10 The R represents an alkyl group, preferably a C1-C4 alkyl group, such as methyl, or a (C1-C4) alkylcarbonyl group, such as acetyl, and preferably, R represents a hydrogen atom. compound and one of the optical or geometric isomers of this compound, and / or one of the solvates of this compound, such as the hydrate. That is the case.

[0107] In other words, the compound of formula (I) is selected, more preferably, from the group consisting of the compound of formula (I'') and mixtures thereof.

[0108] Preferably, in formula (I''), R is a hydrogen atom.

[0109] Preferably, the compound of formula (I) is the following formula (I'''): [ka] A compound that corresponds to, In the formula (I'''), X corresponds to a divalent group, -C(O)- or -(CH)OH-, preferably -C(O)-. compound, and one of the optical or geometric isomers of this compound, and / or one of the solvates of this compound, such as the hydrate. That is the case.

[0110] The cosmetic ingredient (preferably the compound of formula (I) described above) may be present in an amount of at least 25% by mass of the active ingredient of the cosmetic ingredient (specifically formula (I)) relative to the total mass of the aqueous medium, preferably in an amount in the range of 25% to 80% by mass, more preferably in an amount in the range of 25% to 75% by mass, and more preferably in an amount in the range of 30% to 70%.

[0111] Preferably, the aqueous medium contains at least one compound of formula (I') in an amount of at least 25% by mass, preferably in the range of 25% to 80% by mass, and more preferably in the range of 28% to 75% by mass, based on the total mass of the aqueous medium.

[0112] More preferably, the aqueous medium contains at least one compound of formula (I'') or (I''') in a content of at least 25% by mass, more preferably in a content ranging from 40% to 80% by mass, and more preferably in a content ranging from 50% to 75% by mass, based on the total mass of the aqueous medium.

[0113] salt According to the general features of the present invention, the at least one salt is specifically different from a surfactant.

[0114] Preferably, the at least one salt is selected from the group consisting of inorganic salts, organic salts, and mixtures thereof.

[0115] Preferably, the at least one salt is of formula (IV): D y+ A w- (IV) Selected from the compounds, In formula (IV), y is an integer in the range of 1 to 3. w is an integer in the range of 1 to 3. A is an organic or inorganic anion, preferably an organic anion. D is an organic or inorganic cation, preferably an inorganic cation.

[0116] This salt remains electrically neutral, meaning that the absolute value of the sum of the negative charges of the anions is equal to the sum of the positive charges of the cations.

[0117] Preferably, in formula (IV), w is equal to 1 or 2, preferably equal to 1. y is equal to 1 or 2, preferably equal to 1.

[0118] Preferably, in equation (IV), w is equal to 1 and y is equal to 1.

[0119] A w- is nitrate (NO3 - ), carbonate (CO3 2- ), halides, specifically chlorides (Cl - It can be an inorganic anion selected from the group consisting of ), and more preferably, nitrate (NO3 - ), and halides, specifically chlorides (Cl - It can be an inorganic anion selected from the group composed of ).

[0120] A w- C1~C 18 Carboxylic acid, preferably C1-C 10 The organic anion may be selected from the group consisting of carboxylic acids, preferably C1-C6 carboxylic acids, more preferably C1-C4 carboxylic acids, even more preferably C1-C2 carboxylic acids, and even better preferably C2 carboxylic acids, and more specifically, it may be an organic anion selected from the group consisting of C1-C6 carboxylic acids.

[0121] Preferably, A w- C1-C1 is an organic anion, preferably linear or branched, cyclic or acyclic C1-C1 18 Carboxylic acid, preferably C1-C 10 Organic anions are selected from the group consisting of carboxylic acids, and more preferably from the group consisting of C1-C6 carboxylic acids.

[0122] Preferably, A w- This is a linear C1-C 18 Organic anions are selected from the group consisting of carboxylic acids, and more preferably from the group consisting of C1-C6 carboxylic acids.

[0123] Preferably, A w- These are C1-C4 carboxylic acids, preferably C1-C2 carboxylic acids, and even better, C2 carboxylic acids, such as acetate (CH3COO - It is an organic anion selected from the group consisting of ).

[0124] According to one embodiment, D y+ This can be an organic cation, preferably an organic cation selected from the group consisting of ammonium ions, phosphonium ions, imadazolium ions, pyrazolium ions, piperidinium ions, and piperadinium ions.

[0125] According to one embodiment, D y+ This is an inorganic cation selected from the group consisting of alkali metal cations and alkaline earth metal cations.

[0126] To have an advantage, D y+ These include alkali metal cations, alkaline earth metal cations, and ammonium ions (NH4 + It is composed of cations selected from the group consisting of alkali metal cations and alkaline earth metal cations.

[0127] Preferably, D y+ , calcium ions (Ca 2+ ), magnesium ions (Mg 2+ ), sodium ions (Na + ), and potassium ions (K + It is composed of ), specifically calcium ions and sodium ions, and more specifically, it is a cation selected from the group composed of sodium ions.

[0128] Preferably, the salt is given by the following formula (IV1): [ka] It supports, In formula (IV1), D + This has the same meaning as shown in equation (IV), and y=1, R2 is saturated or unsaturated, linear or branched, cyclic or acyclic, preferably acyclic C1-C 10 This represents an alkyl chain, preferably a C1-C6 alkyl chain, more preferably a C1-C4 alkyl chain, and specifically a C1 alkyl chain.

[0129] Preferably, R2 represents a linear or branched, saturated or unsaturated, cyclic or acyclic, preferably acyclic C1-C6 alkyl chain, more preferably a C1-C4 alkyl chain, specifically a C1 alkyl chain.

[0130] According to one embodiment, R2 represents a linear or branched, saturated or unsaturated, cyclic, for example, cyclohexyl or cyclopentyl, or acyclic C1-C6 alkyl chain, more preferably a C1-C4 alkyl chain, specifically a C1 alkyl chain.

[0131] Preferably, R2 is a linear or branched, preferably linear, saturated or unsaturated, acyclic C1-C2. 10 This represents an alkyl chain, preferably a C1-C6 alkyl chain, more preferably a C1-C4 alkyl chain, and specifically a C1 alkyl chain.

[0132] Preferably, R2 is a linear, saturated or unsaturated, acyclic C1-C2. 10 This represents an alkyl chain, preferably a C1-C6 alkyl chain, more preferably a C1-C4 alkyl chain, and specifically a C1 alkyl chain.

[0133] Primarily, R2 represents a linear, saturated or unsaturated, acyclic C1-C4 alkyl chain, specifically a C1 alkyl chain.

[0134] Preferably, in formula (IV1), D + This represents an inorganic cation selected from the group consisting of alkali metal cations and alkaline earth metal cations.

[0135] Advantageously, in equation (IV1), D + These include alkali metal cations, alkaline earth metal cations, and ammonium ions (NH4 + It is composed of alkali metal cations and alkaline earth metal cations, specifically sodium ions (Na + ), potassium ions (K + ), or ammonium (NH4 + It is a cation selected from the group consisting of ).

[0136] More preferably, in equation (IV1), D + This is sodium ion (Na + This represents ).

[0137] Preferably, the at least one salt is selected from the group consisting of alkali metal salts, alkaline earth metal salts, ammonium salts, and mixtures thereof.

[0138] Preferably, the at least one salt is selected from the group consisting of calcium salts, magnesium salts, sodium salts, potassium salts, and mixtures thereof, and more preferably from the group consisting of calcium salts, sodium salts, and mixtures thereof.

[0139] Preferably, the at least one salt is selected from the group consisting of C1-C6 carboxylic acids, preferably C1-C4 carboxylic acids, more preferably C1-C2 carboxylic acids, and even better, alkali metal salts of C2 carboxylic acids, such as sodium acetate.

[0140] Preferably, the at least one salt is selected from the group consisting of alkali metal salts, alkaline earth metal salts, ammonium salts, and mixtures thereof.

[0141] Preferably, the at least one salt is selected from the group consisting of calcium salts, magnesium salts, sodium salts, potassium salts, and mixtures thereof, and more preferably from the group consisting of calcium salts, sodium salts, and mixtures thereof.

[0142] Preferably, the at least one salt is selected from the group consisting of C1-C6 carboxylic acids, preferably C1-C4 carboxylic acids, more preferably C1-C2 carboxylic acids, and even better, alkali metal salts of C2 carboxylic acids, such as sodium acetate.

[0143] This salt may or may not contain impurities.

[0144] Preferably, the salt may be an impurity arising from, for example, at least one step of a method for preparing at least one cosmetic ingredient (preferably at least one compound of formula (I)), and / or an impurity arising from at least one step of at least one washing and / or purification method performed before, after, or during, preferably after, at least one step of a method for preparing at least one cosmetic ingredient (preferably at least one compound of formula (I)).

[0145] Preferably, the salt is an impurity.

[0146] The salt, preferably the salt of formula (IV), and more preferably the salt of formula (IV1), may be present in a content range of 0.05% to 50% by mass relative to the total mass of the aqueous medium, more specifically in a content range of 0.1% to 40% by mass, and more specifically in a content range of 0.5% to 30% by mass.

[0147] More preferably, the salt corresponding to formula (IV1) may be present in a content ranging from 0.05% to 45% by mass relative to the total mass of the aqueous medium, more specifically in a content ranging from 0.1% to 35% by mass, and more specifically in a content ranging from 0.5% to 25% by mass.

[0148] Preferably, the aqueous medium is - At least one compound of formula (I) as defined above, and - At least one salt that corresponds to formula (IV) defined above, and more preferably to formula (IV1) defined above. Includes.

[0149] Advantageously, this aqueous medium is - At least one compound of formula (I') as defined above, and - Corresponding to formula (IV1) defined above, at least one salt selected from the group consisting of alkali metal salts, alkaline earth metal salts, ammonium salts, and mixtures thereof. Includes.

[0150] More importantly, this aqueous medium is - At least one compound of formula (I'') as defined above, and - Corresponding to formula (IV1) defined above, at least one salt selected from the group consisting of alkali metal salts, alkaline earth metal salts, ammonium salts, and mixtures thereof. Includes.

[0151] Electrodialysis process (PU1) As described above, the purification method (PU) according to the present invention comprises at least one step of electrodialysis (PU1) of at least one aqueous medium containing at least the cosmetic ingredient (preferably the compound of formula (I)) and at least one salt as defined above.

[0152] In other words, the method (PU) according to the present invention comprises at least one step (PU1) in which at least the aqueous medium defined above is subjected to at least one electrodialysis (preferably one electrodialysis).

[0153] To put it another way, the aqueous medium defined above is transported to an electrodialysis machine in order to separate the salt from the aqueous medium.

[0154] Preferably, the purification method (PU) according to the present invention comprises at least one step (PU1) of electrodialysis of at least one aqueous medium containing at least one compound of formula (I) and at least one salt of formula (IV1), as defined above.

[0155] The method of the present invention involves performing an electrolysis step. Electrodialysis is a process known to those skilled in the art, and is an electrochemical process that makes it possible to extract ions (anions or cations) contained in a solution (see, for example, l'actualite chimique, L'electrodialyse et ses nombreuses applications [Electrodialysis and its many applications], F. Lutin-no.327-328, February-March 2009).

[0156] The principle of this process is to use charged (cationic or anionic) membranes, which are used to separate ions from a solution (especially an aqueous solution) using the driving force of a potential difference. Electrodialysis machines are often built on the principle of a filter press, consisting of a continuous membrane stack that may contain tens or even hundreds of alternating cationic and anionic membranes between two electrodes. The solution (feed solution, especially an aqueous solution) reaching the machine flows through various cells (i.e., the space between two continuous membranes (membrane pairs)). When a potential difference is applied between the two electrodes, positively charged cations in the feed solution move toward the cathode. These ions readily pass through the negatively charged cation exchange membrane but are held by the positively charged anion exchange membrane. Conversely, negatively charged anions move toward the anode, pass through the anion exchange membrane, and are held by the cation exchange membrane. Due to the arrangement of the ion-selective membranes, the moving ions are concentrated in each of the alternating cells of the stack. Thus, the ions removed from the aqueous feed solution are concentrated in two separate flows.

[0157] In summary, ion extraction is carried out by the movement of ions through at least two selective (anionic or cationic) membranes under the action of an electric field. Only anions can pass through the anionic membrane, and only cations can pass through the cationic membrane. By arranging several membranes in parallel that allow alternating passage of positive and negative ions, certain ions can be removed from a solution (especially an aqueous solution).

[0158] Therefore, electrodialysis can separate, concentrate, and / or purify C-glycoside derivatives such as the compound of formula (I) from aqueous solutions.

[0159] In some sections, ions are concentrated, while in others, ions are removed. Particles without an electric charge are not removed.

[0160] The method of the present invention may utilize conventional electrodialysis (ED) or bipolar electrodialysis (BPED).

[0161] According to one embodiment of the present invention, this method uses conventional electrodialysis.

[0162] The terms "conventional electrodialysis," or ED, or concentrated electrodialysis, are understood to refer to a device that performs the electrochemical separation of ions in a composition (specifically an aqueous composition) transferred from one membrane to the next by selective exchange using a DC voltage. Thus, conventional electrodialysis can be used to purify, concentrate, and desalt.

[0163] The term "bipolar electrodialysis" or BPED is understood to mean an ion exchange membrane electrodialysis apparatus that uses at least one bipolar membrane to split water into protons and hydroxide ions (i.e., to produce acidic and alkaline flows). Under the driving force of an electric field, the bipolar membrane separates water into hydrogen ions (H₂O₂). + ) and hydroxide ions (OH - ) dissociates into . The bipolar membrane is formed from an anion exchange layer and a cation exchange layer bonded to each other, and a very thin interface through which water diffuses from the external saline solution. With the anion exchange side facing the anode and the cation exchange side facing the cathode, hydroxyl anions are transported through the anion exchange layer and hydrogen cations are transported through the cation exchange layer. The bipolar membrane allows for the generation and concentration of hydroxyl and hydrogen ions on its surface. These ions can be used in an electrodialysis laminate to combine with salt cations and anions to produce acids and bases (or alkaline agents).

[0164] This process allows for adjustment of the solution's pH without the addition of alkaline agents or acids.

[0165] The membranes in an electrolysis apparatus are either anionic or cationic. Cationic membranes are often composed of sulfonated polymers or phosphorylated polymers, such as sulfonated polystyrene, while anionic membranes are often composed of polymers containing quaternary ammonium or phosphonium, such as polystyrene containing quaternary ammonium. Preferably, these membranes are sulfonated membranes and quaternary ammonium membranes.

[0166] Pretreatment may be necessary before electrodialysis. Suspended solids larger than 10 mm in diameter must be removed; otherwise, these solids may clog the membrane pores. Additionally, substances that can neutralize the membrane, such as large organic anions, colloids, iron oxides, and manganese oxides, exist. These interfere with the membrane's selective effect.

[0167] Prior to electrolysis, the composition may be filtered or passed through an ion exchange resin.

[0168] Prior to electrodialysis, the pH of the aqueous composition containing the cosmetic ingredient is higher than the pKa of the conjugate acid (weak acid) salt. Preferably, prior to electrolysis, the pH of the aqueous composition containing the C-glycoside derivative is at least 4, more preferably at least 5, even more preferably at least 6, and even more preferably at least 7. This pH can be adjusted using an alkaline agent or acid such as acetic acid, sodium hydroxide, or an alkaline agent such as a (bi)carbonate.

[0169] Anion exchange membranes or cation exchange membranes suitable for concentration by electrodialysis can be used in the method of the present invention. Such membranes are commercially available from Astom Corp. (Tokyo, Japan, e.g., Neosepta membranes), Tokuyama Co., Ltd. (Tokyo, Japan), and Ameridia (Somerset).

[0170] Conventional electrodialysis processes can be carried out using any commercially available electrodialysis unit. Such units are commercially available from various suppliers such as Valeo (France), Eurodia Industrie SA (France), EET Corporation (US), Ameridia (US), or Mega AS (Czech Republic).

[0171] Concentrated electrodialysis is preferably performed using a known configuration as an electrodialysis cell. This cell consists of a feed (diluent) compartment and a concentrate (brine) compartment formed by anion exchange membranes and cation exchange membranes placed between two electrodes. The electrodialysis process preferably uses multiple electrodialysis cells arranged in a known configuration as an electrodialysis stack, where alternating anion exchange membranes and cation exchange membranes form multiple electrodialysis cells. The number of cells in the stack can range from a few cells (e.g., 10 cells) to several hundred cells.

[0172] Electrodialysis parameters include, in particular, current density, cell voltage, current efficiency, diluent concentration, and concentrate concentration.

[0173] The amount of current (current density) determines the equivalent amount (in grams) of product transported through the membrane. Operating at high current densities can reduce the required surface area of ​​the electrodialysis cell. The current density is preferably balanced with an increase in cell voltage; however, this can lead to higher energy consumption.

[0174] The term "limiting current" is understood to mean the maximum current density that can be tolerated to avoid a sudden increase in cell voltage. The limiting current can depend on parameters such as the design of the laminate, the concentration of the composition (specifically aqueous compositions), and the temperature.

[0175] The current efficiency also determines the surface area of ​​the film required for the method of the present invention.

[0176] The term "current efficiency" is understood to mean the efficiency of an electrochemical process.

[0177] Current efficiency takes into account all potential parasitic phenomena occurring in the film stack (e.g., film permeation selectivity < 100%), physical leakage (resulting in impurities in the product, which can be reduced by optimized stack design and film selection).

[0178] According to a particular embodiment of the present invention, the ratio of electrical energy consumed per kg is 0.01 kW / h / kg to 0.2 kW / h / kg, and more preferably 0.03 kW / h / kg to 0.1 kW / h / kg.

[0179] Another important parameter is the concentration (conductivity) of the two flows. The conductivity ratio affects the current efficiency and limits the maximum concentration of the concentrate (brine) flow. Generally, the minimum concentration of the diluent is limited by conductivity considerations, due to the ohmic resistance of the diluent cell and the low limiting current at low conductivity. The minimum conductivity that can be assumed is about 0.5 mS / cm. The minimum starting concentration of the salt / cosmetic component (specifically a C-glycoside derivative) for performing concentrated electrodialysis is a concentration where the conductivity is preferably at least 10 mS / cm, more preferably at least 20 mS / cm, and even more preferably at least 30 mS / cm.

[0180] According to certain embodiments of the present invention, the composition (specifically, an aqueous composition) is preferably pretreated to remove impurities and particles (specifically, to remove acetic acid). Any pretreatment method known to those skilled in the art may be used, such as centrifugation, microfiltration, nanofiltration, ion exchange, or distillation (specifically, preferably distillation under reduced pressure).

[0181] If the membrane becomes contaminated with impurities, these impurities can be washed away using the current inversion solution, or conventional processes known to those skilled in the art, such as the use of dilute acid solutions, caustic solutions, and / or enzyme solutions.

[0182] The temperature range for conventional electrodialysis laminates or bipolar electrodialysis laminates is preferably 10°C to 50°C, specifically 35°C to 40°C.

[0183] The pH range of the electrodialysis laminate (especially conventional electrodialysis laminates) is preferably 3 to 8, and more preferably 4 to 7.

[0184] According to a particular embodiment, the conventional electrodialysis or bipolar electrodialysis of the present invention is performed at a temperature of 10°C to 50°C, specifically at a temperature of 15°C to 40°C, preferably at a temperature of 20°C to 35°C, for example, 25°C.

[0185] According to one embodiment, the method of the present invention specifically uses a conventional electrodialysis process that is carried out at a pH of at least 4, preferably at a pH of at least 5, more preferably at a pH of at least 6, and preferably at a pH of 8 or less.

[0186] According to a particular embodiment of the present invention, in the electrodialysis step of this method, a composition containing a salt / cosmetic component (specifically a C-glycoside derivative) (specifically an aqueous composition) is introduced into the electrodialysis laminate through a diluent compartment.

[0187] When this solution reaches the active region of the cell, the DC voltage moves positively charged cations to the cathode and negatively charged anions to the anode. When these ions reach the ion exchange membrane, the properties of this membrane determine whether they are blocked or allowed to pass through. Ions that can pass through the membrane are retained in the next compartment because the next membrane in their path will have the opposite charge. Thus, there are compartments where ions are removed and compartments where ions are concentrated. If the solution circulates rapidly through the stack, diluent and concentrated flows are obtained. The product may be a desalination flow, a concentration flow, or both.

[0188] Bipolar electrodialysis According to a preferred embodiment of the present invention, the method involves performing at least one bipolar electrodialysis or bipolar membrane electrodialysis step.

[0189] This bipolar electrodialysis may involve first contacting a concentrate obtained from conventional electrodialysis with the C-glycoside derivative of formula (I), followed by at least one bipolar membrane electrodialysis.

[0190] According to a preferred embodiment of the present invention, the method is performed by first executing a bipolar electrodialysis process without first performing a conventional electrodialysis process.

[0191] Bipolar electrodialysis can be performed using any available bipolar electrodialysis unit. Such units are commercially available from suppliers such as The Electrosynthesis Company, Inc. (US), FuMA-Tech GmbH (Germany), Solvay SA (Belgium), Tokuyama Co. Ltd. (Japan), Graver Water Co. (US), Tianwei, Membrane Technology Co. Ltd. (China), Ameridia (US), and Eurodia Industrie SA (France).

[0192] Any bipolar membrane suitable for bipolar membrane electrodialysis can be used in the method of the present invention. Such membranes are commercially available from Astom Corp. (Tokyo, Japan, e.g., Neosepta membrane), Tokuyama Co., Ltd. (Tokyo, Japan), Ameridia (Somerset, NJ, USA), Eurodia Industrie SA (Wissous, France), CelTech, Inc. (Fayetteville, North Carolina, USA), Eden Purification Systems (North Haven, CT, USA), Ion Power, Inc. (Bear, DE, USA), Minntech Corporation (Minneapolis, MN, USA), and GE Water & Process Technologies (Trevose, Pennsylvania, USA), Veolia, France.

[0193] The membranes sold by Veolia may include AR204, AR103, AR908, CR64, CR67, and CR61. The membranes may be supported, woven, or the polymer may be cast onto various fabrics. The different fabrics are indicated by the following single letter: R → Acrylic woven fabric, H → Heavy acrylic woven fabric, E → Polyester nonwoven fabric, T → Thin polyester nonwoven fabric, U → Ultra-thin polyester nonwoven fabric, P → Polypropylene woven fabric, N → Thin polypropylene nonwoven fabric. The name of each membrane type may be a combination of the membrane's chemical properties and supporting structure (e.g., AR103P, CR67T). The membranes have certain electrical resistance and permeability selectivity.

[0194] Ion exchange membranes such as Ionics have certifications such as NSF 61, 21 CFR 175, 176, 177, 178, 182 for drinking water; and EU 1935 / 2004 and EU 10 / 2001 for materials in contact with food.

[0195] According to a particular embodiment, the bipolar membrane electrodialysis of the present invention is performed at a temperature of 10°C to 40°C, specifically at a temperature of 15°C to 35°C, preferably at a temperature of 20°C to 30°C, for example, 25°C.

[0196] It is understood in this specification that a concentrated electrodialysis unit and a bipolar membrane electrodialysis unit may be incorporated into the same apparatus.

[0197] Various bipolar membrane electrodialysis configurations are possible and are described by the manufacturer.

[0198] By adding a bipolar membrane to a conventional electrodialysis cell, a three-compartment cell can be obtained. In such a case, the bipolar membrane is positioned on either the anion exchange membrane or the cation exchange membrane described above, forming the following three compartments: an acid between the bipolar membrane and the anion exchange membrane, a base between the bipolar membrane and the cation exchange membrane, and a salt between the cation exchange membrane and the anion exchange membrane.

[0199] A two-compartment cell can be obtained by adding a bipolar membrane and a cation exchange membrane, or by adding a bipolar membrane and an anion exchange membrane.

[0200] According to one embodiment of the present invention, alternating cation exchange membranes and bipolar membranes are used.

[0201] Advantageously, the electrodialysis process (PU1) is carried out at a pH in the range of 4 to 9, preferably at a pH in the range of 4.5 to 8.5, more preferably at a pH in the range of 5 to 8, and more preferably at a pH in the range of 6.5 to 7.5.

[0202] The electrodialysis process (PU1) is performed at a pH of less than 8 to efficiently reduce the content of ionic impurities (i.e., salt content) that preferably correspond to formula (II), and more preferably to formula (II').

[0203] The electrodialysis process (PU1) can be performed at a temperature in the range of 20°C to 50°C, and preferably at a temperature in the range of 25°C to 45°C.

[0204] Preferably, the electrodialysis process (PU1) is carried out by conventional electrolysis, and more preferably by conventional electrolysis at a "product" conductivity (i.e., before treatment) in the range of 50 to 0.05 mS / cm, preferably in the range of 40 to 0.2 mS / cm, measured at a temperature in the range of 20°C to 50°C.

[0205] According to one embodiment, the electrodialysis process (PU1) is performed by hyperbolic membrane electrodialysis at a product conductivity (before treatment) measured at a temperature in the range of 20°C to 50°C, in the range of 60 to 0.5 mS / cm, preferably in the range of 55 to 1 mS / cm, more preferably in the range of 50 to 10 mS / cm, and even more preferably in the range of 45 to 20 mS / cm. Preferably, the concentration of the cosmetic component (especially the C-glycoside derivative) is 10% to 70% by mass, specifically 20% to 60% by mass, and more specifically 30% to 50% by mass.

[0206] Preferably, the electrodialysis process (specifically, conventional electrodialysis) (PU1) is performed at a pH in the range of 5 to 8, more preferably at a pH in the range of 4 to 8, and at a temperature in the range of 20°C to 50°C, more preferably at a temperature in the range of 25°C to 45°C.

[0207] Preferably, the electrodialysis and bipolar membrane electrodialysis processes (PU1) are carried out at an alkaline pH (i.e., greater than 7), more preferably at a pH of 8 or higher, even better at a pH of 9 or higher, specifically at a pH of 9.5 to 12, and specifically at a temperature in the range of 20°C to 50°C, more preferably at a temperature in the range of 25°C to 45°C.

[0208] The electrodialysis apparatus specifically includes a first electrode constituting the anode and a second electrode constituting the cathode, thereby applying an electric field to all components of the electrodialysis apparatus between the first electrode and the second electrode when a DC source is applied.

[0209] Between the first electrode and the second electrode, the electrodialysis apparatus may include a series of compartments mounted in parallel and each formed by two membranes (specifically, an anionic or anion-exchange membrane, i.e., an anion-permeable and cation-impermeable membrane, and a cationic or cation-exchange membrane, i.e., a cation-permeable and anion-impermeable membrane). The anionic membrane and the cationic membrane are arranged alternately within the electrodialysis apparatus.

[0210] Therefore, each compartment is formed by anionic and cationic films that are spaced apart from each other.

[0211] In other words, the electrodialysis machine may be of a conventional type, containing a laminate of alternating cation exchange membranes and anion exchange membranes placed within an electric field generated by electrodes.

[0212] Between the first electrode and the second electrode, the electrodialysis apparatus generally includes a compartment called a dilution compartment, located in the center of the apparatus, within which the aqueous solution defined above circulates.

[0213] This dilution compartment is located between two adjacent compartments called concentration compartments. In other words, this concentration compartment is located next to this dilution compartment. In other words, this dilution compartment and concentration compartment are arranged alternately within the electrodialysis machine. To put it another way, this dilution compartment is sandwiched between two concentration compartments.

[0214] Therefore, during the circulation of the aqueous medium as defined above within the dilution section, firstly, under the effect of the electric current, the salt anions attracted toward the anode move from the dilution section to the concentration section by crossing the anionic membrane, and remain stuck within this concentration section due to the cationic membrane.

[0215] Secondly, the cations of the salt attracted to the cathode move from the dilution compartment to the concentration compartment by crossing the cationic membrane, and remain stuck in this concentration compartment due to the anionic membrane.

[0216] Therefore, this salt is extracted from a dilution section where an aqueous medium circulates, and the anions and cations of this salt are concentrated in the respective adjacent concentration sections.

[0217] Therefore, the electrodialysis process (PU1) can reduce the salt content in the aqueous medium as defined above.

[0218] Next, the aqueous medium according to the present invention, which contains at least one compound of formula (I) and is located within the dilution section, is recovered at the outlet of the electrodialyzer via a pipe.

[0219] Electrodialysis is advantageous in that it allows for the removal of a very large amount of impurities in ionic form from an aqueous medium containing at least the cosmetic component (preferably the compound of formula (I) as defined above).

[0220] Therefore, the electrodialysis process (PU1) makes it possible to obtain a salt content that is likely to be 10% by mass or less, preferably 5% by mass or less, more preferably in the range of 1% to 5% by mass, and even better in the range of 1.5% to 2% by mass, relative to the total mass of the dry extract containing the cosmetic surfactant.

[0221] In other words, at the end of the purification method (PU), the cosmetic component (preferably the compound of formula (I)) is preferably in the form of a dry extract containing at least 10% by mass or less, preferably 5% by mass or less, more preferably between 1% by mass and 5% by mass, and even better between 1.5% by mass and 2% by mass, of the total mass of the dry extract.

[0222] The aqueous medium or aqueous solution recovered in this manner can be used for cosmetic purposes.

[0223] Preferably, the purification method (PU) comprises at least one step (PU1) of electrodialysis of at least one aqueous medium containing at least one cosmetic ingredient (preferably at least one compound of formula (I) as defined above) and at least one salt preferably corresponding to formula (II), and more preferably to formula (II').

[0224] According to one embodiment, the purification method (PU) according to the present invention is a method using at least one aqueous medium, - At least one cosmetic ingredient, - Preferably at least one salt corresponding to formula (IV1) The method includes at least one step (PU1) of electrodialysis of an aqueous medium containing [the specified substance].

[0225] More preferably, the purification method (P) according to the present invention is at least one aqueous medium, - At least one cosmetic ingredient, - At least one salt corresponding to formula (IV1), particularly selected from the group consisting of alkali metal salts, alkaline earth metal salts, ammonium salts, and mixtures thereof. The method includes at least one step (PU1) of electrodialysis of an aqueous medium containing [the specified substance].

[0226] More preferably, the purification method (PU) according to the present invention is at least one aqueous medium, - At least one compound of formula (I’) as defined above, 〇 Preferably, in formula (I’), R1 is a linear C1-C 10 alkyl chain, preferably a C1-C6 alkyl chain, more preferably a C1-C4 alkyl chain, specifically a C1 alkyl chain, compound, - At least one salt preferably corresponding to formula (IV1) comprises at least one step (PU1) of electrodialysis of an aqueous medium containing it.

[0227] Even more preferably, the purification method (P) according to the present invention is at least one aqueous medium, - At least one compound of formula (I’’) as defined above, 〇 Preferably, in formula (I’’), R1 is a linear C1-C 10 alkyl chain, preferably a C1-C6 alkyl chain, more preferably a C1-C4 alkyl chain, specifically a C1 alkyl chain, compound - At least one salt corresponding to formula (IV1), particularly selected from the group consisting of alkali metal salts, alkaline earth metal salts, ammonium salts, and mixtures thereof comprises at least one step (PU1) of electrodialysis of an aqueous medium containing it.

[0228] Method for preparing at least one cosmetic active agent (PR) As shown above, the preparation method (PR) according to the present invention preferably has the following formula (I):

Chem.

[0229] For the purposes of the present invention, SA' corresponds to SA-OH, SA has the same meaning as SA' as defined above, and the hydroxyl group-OH is a free hydroxyl group.

[0230] Within the scope of the present invention, a compound of formula (IA) is a compound of formula (I) (wherein X corresponds to a -C(O)- group).

[0231] Within the scope of the present invention, a compound of formula (IB) is a compound of formula (I) (wherein X corresponds to a -CH(OR)- group and R is as defined above).

[0232] The method (PR) according to the present invention is particularly advantageous because the electrodialysis antibody (PU1) can efficiently reduce not only the salt content generated from the synthesis step (PR1) and / or the reaction step (PRii), but also the salt content formed at the end of the neutralization step (PR0).

[0233] Advantageously, the reaction step (PR1) is carried out in an aqueous medium. ○ At least one compound of formula (II), Preferably, an equimolar amount or an excess, preferably an excess, of at least one compound of formula (III) relative to the compound of formula (II), Preferably, the compound of formula (III) is present in an amount greater than 1, preferably in the range of 1 to 5, more preferably in the range of 1 to 4, even more preferably in the range of 1 to 3, even better in the range of 1 to 2, specifically in the range of 1 to 1.5 molar equivalents relative to the compound of formula (II). Compound of formula (III), ○ At least one type of alkaline agent, □ Preferably, at least one alkaline agent as described above, selected from the group consisting of alkali metal hydroxides and alkaline earth metal hydroxides, alkali metal (bi)carbonates and alkaline earth metal (bi)carbonates, and mixtures thereof, specifically selected from the group consisting of alkali metal hydroxides and alkaline earth metal hydroxides, and more preferably alkaline earth metal hydroxides, such as sodium hydroxide. An alkali agent that is present in an equimolar amount or in excess with respect to the compound of formula (II), preferably present in excess, □ Preferably, this alkali agent is present in an amount in the range of 1 to 5 molar equivalents, more preferably in the range of 1 to 4 molar equivalents, more preferably in the range of 1 to 3 molar equivalents, and even better in the range of 1 to 2 molar equivalents with respect to the compound of formula (II). Alkali agent is carried out in the presence of, 〇 Preferably, reaction step (i) is □ carried out at a temperature in the range of 30 °C to 80 °C, preferably in the range of 30 °C to 70 °C, more preferably in the range of 30 °C to 60 °C, and even better in the range of 30 °C to 50 °C. 〇 Preferably, the duration of this reaction is □ variable over 10 minutes to 10 hours, preferably 20 minutes to 5 hours, more preferably 30 minutes to 4 hours.

[0234] Preferably, reaction step (PR1) is carried out in an aqueous medium, 〇 Preferably, specifically, the addition of at least one compound of formula (II) to the aqueous medium at various temperatures of 30 °C to 80 °C, 〇 Preferably, after dissolving the compound of formula (II) in this aqueous medium, this temperature is advantageously lowered. 〇 Preferably, the addition of at least one compound of formula (III) to the aqueous medium containing at least the compound of formula (II). 〇 Preferably, the addition of an equimolar amount or excess, preferably excess, of at least one alkali agent (preferably an inorganic alkali agent) as described above with respect to the compound of formula (II) at a temperature preferably not exceeding 45 °C. 〇 Preferably, heating the reaction medium containing at least the compound of formula (II), at least one compound of formula (III), and at least one alkali agent to the reaction temperature described above. Preferably, at the end of reaction (PR1), the reaction medium can be cooled to at least 5°C, preferably at least 10°C, and more preferably at least 15°C. It contains a series of them.

[0235] Preferably, at the end of reaction step (PR1), the pH may be adjusted to a value of 8.5 or less, and more preferably to a value of 2.5 or more, and preferably the pH changes within the range of 2.5 to 8.5.

[0236] The neutralization step (PR0) may be performed simultaneously with or sequentially with the electrodialysis step (PU1), preferably sequentially with the electrodialysis step (PU1), and preferably before the electrodialysis step (PU1).

[0237] The neutralization step (PR0) advantageously allows for the neutralization of any excess alkaline agent present in the aqueous reaction medium obtained from step (PR1).

[0238] Preferably, the preparation method (PR) includes at least one neutralization step (PR0) which comprises at least one acidification treatment as defined above (e.g., the use of a resin or the addition of at least one acidifying agent (preferably an organic acidifying agent) as defined above).

[0239] Preferably, at least one electrodialysis step (PU1) is performed after the reaction step (PR1), or after one of the reaction steps (PRii), or between the reaction step (PR1) and at least one reaction step (PRii), and optionally after the neutralization step (PR0).

[0240] Advantageously, at least one electrodialysis step (PU1) is performed after the reaction step (PR1).

[0241] Similarly advantageously, at least one electrodialysis step (PU1) is performed between the reaction step (PR1) and at least one reaction step (PRii).

[0242] Therefore, according to a favorable embodiment, the method (PR) of the present invention is - At least one reaction step (PR1) as defined above, - At least one step (PR0) as defined above, which neutralizes the reaction medium obtained from step (PR1), - Optionally, at least one reaction step (PRii) as defined above, - At least one purification step (PU) as described above, preferably performed after reaction step (PR1) or optionally after reaction step (PRii), and more preferably between reaction step (PR1) and reaction step (PRii). Includes.

[0243] Similarly advantageously, at least one electrodialysis step (PU1) is performed after the neutralization step (PR0).

[0244] According to one embodiment, the method according to the present invention includes one electrodialysis step (PU1).

[0245] According to another embodiment, the method according to the present invention includes several electrodialysis steps (PU1).

[0246] According to one embodiment, at least one electrodialysis step (PU1) is performed after the reaction step (PR1).

[0247] According to another embodiment, the electrodialysis step (PU1) is performed at least once after the reaction step (PRii).

[0248] According to a particular embodiment, the electrodialysis step (PU1) is performed at least once after step (PR1), and the method of the present invention does not include step (PRii).

[0249] According to another embodiment, the method of the present invention comprises at least one step (PR1), preferably one step (PR1), and at least one step (PRii), preferably one step (PRii), wherein the electrodialysis step (PU1) is performed at least once after the at least one step (PR1) without being performed after step (PRii).

[0250] In yet another embodiment, the method of the present invention comprises at least one step (PR1), preferably one step (PR1), and at least one step (PRii), preferably one step (PRii), wherein the electrodialysis step (PU1) is performed at least once after the at least one step (PRii) without being performed at the end of step (PR1).

[0251] According to another embodiment, the method of the present invention comprises at least one step (PR1), preferably one step (PR1), and at least one step (PRii), preferably one step (PRii), wherein the electrodialysis step (PU1) is performed at least once after at least one step (PR1) and at least once after at least one step (PRii).

[0252] According to a preferred embodiment, the method of the present invention comprises one step (PR1) and one step (PRii), wherein the electrodialysis step (PU1) is performed at least once after step (PR1) without being performed at the end of step (PRii).

[0253] Reaction process (PRii) The preparation method (PR) may optionally further include at least one step (PRii) of reacting at least the cosmetic component.

[0254] The preparation method (PR) may further include at least one step (PRii) in which at least one compound of formula (I) (wherein X corresponds to a -C(O)- group, i.e., a compound of formula (IA)) is reacted to form at least one compound of formula (I) (wherein X corresponds to a -CH(OR)- group, i.e., a compound of formula (IB)).

[0255] According to an advantageous embodiment, the method (PR) according to the present invention further comprises at least one step (PRii) of reacting at least one compound of formula (IA) to form at least one compound of formula (IB).

[0256] Reduction process (PRii) The reaction step (PRii) is preferably the following synthesis route (B): [ka] This is a reduction process (PR2) carried out in an aqueous medium according to the following: During synthesis route (B), SA' and R1 have the same meanings as in equation (I).

[0257] Within the scope of the present invention, a compound of formula (I'B) is a compound of formula (IB) (wherein R represents a hydrogen atom).

[0258] In other words, the compound of formula (I'B) is the same as the compound of formula (I) (where X corresponds to the -CH(OR)- group, where R represents a hydrogen atom).

[0259] Preferably, the preparation method according to the present invention is - At least one reaction step (PR1) described above, - Optionally, at least one step (PR0) as defined above, which neutralizes the reaction medium obtained from the reaction step (PR1), - At least one reduction step (PR2) carried out in an aqueous medium according to the synthesis route (B) defined above, - At least one purification step (PU) as described above, performed before and / or after the reduction step (PR2), preferably before the reduction step (PR2). Includes.

[0260] The step of reducing the carbonyl group to obtain the alcohol group is carried out by conventional reduction methods known to those skilled in the art. For example, one can refer to the work Adv. Org. Chem., J. March, 4th Ed., John Wiley & Son, pp. 910-919 (1992).

[0261] The reduction step (PR2) may be a reduction, enzymatic reduction, or catalytic reduction carried out in the presence of one or more hydrides (specifically, hydrogen boride, e.g., NaBH4 or NaBH3CN).

[0262] Preferably, at least one reduction step (PR2) is reduction by catalytic hydrogenation.

[0263] Upon reduction, at least one reduction step (PR2) is advantageously hydrogenation carried out in the presence of at least one catalyst and optionally an acidifying agent. Hydrogenation may be carried out under conditions described, for example, in the literature (Heterocycles, M. Hashimoto and M. Takahashi, 77(1), 227-231 (2009)).

[0264] The catalyst is preferably a metal catalyst such as ruthenium (Ru), rhodium (Rh), platinum (Pt), iridium (Ir), nickel (Ni), or palladium (Pd), preferably ruthenium (Ru), more preferably a metal catalyst selected from ruthenium (Ru), rhodium (Rh), platinum (Pt), or iridium (Ir), and even better, ruthenium (Ru).

[0265] Preferably, the catalyst is supported, and more preferably, ruthenium supported on, for example, carbon (or graphite), alumina, AlSi, zeolite, or barium sulfate (BaSO4). According to one embodiment, hydrogenation is catalyzed by Rh on carbon (Pd / C) or Ru on carbon (Ru / C).

[0266] Preferably, the catalyst is selected from the group consisting of ruthenium on carbon (Ru / C), ruthenium on alumina (Ru / Al), ruthenium on AlSi, ruthenium on zeolite, or ruthenium on barium sulfate (BaSO4).

[0267] Preferably, this catalyst is ruthenium, for example, ruthenium on carbon (Ru / C).

[0268] Preferably, at least one reduction step (PR2) is carried out under a hydrogen pressure in the range of 2 to 100 bar, preferably in the range of 3 to 50 bar, more preferably in the range of 4 to 25 bar, even more preferably in the range of 5 to 15 bar, and even better in the range of 6 to 12 bar, for example, 10 bar.

[0269] Preferably, at least one reduction step (PR2) is carried out at a temperature that may be in the range of 20°C to 150°C, preferably in the range of 30°C to 100°C, and more preferably in the range of 40°C to 100°C.

[0270] Preferably, at least one reduction step (PR2) is carried out over a period of time that may range from 30 minutes to 30 hours, preferably from 45 minutes to 10 hours, and more specifically from 1 hour to 7 hours. Preferably, at least one reduction step (PR2) is reduction by catalytic hydrogenation in the presence of at least one catalyst (specifically ruthenium), under a hydrogen pressure in the range of 2 to 100 bar, and at a temperature in the range of 30°C to 150°C.

[0271] Preferably, at least one reduction step (PR2) is reduction by catalytic hydrogenation in the presence of at least one metal catalyst (particularly ruthenium).

[0272] Preferably, at least one reduction step (PR2) is reduction by catalytic hydrogenation in the presence of at least one catalyst (specifically ruthenium), under a hydrogen pressure in the range of 4 to 50 bar, and at a temperature in the range of 40°C to 100°C.

[0273] Preferably, at least one reduction step (PR2) is reduction by catalytic hydrogenation in the presence of at least one catalyst (specifically ruthenium), under a hydrogen pressure in the range of 5 to 25 bar, and at a temperature in the range of 40°C to 100°C.

[0274] Advantageously, at least one reduction step (PR2) is performed in an aqueous medium. -In the presence of: ○ In the presence of at least one compound of formula (I) (wherein X corresponds to the divalent group -C(O)-), ○ At least one catalyst, more preferably selected from the group consisting of palladium and ruthenium, specifically in the presence of ruthenium on carbon, - Under various hydrogen pressures of 2 to 50 bar, more preferably 4 to 12 bar, - At temperatures in the range of 40°C to 100°C Execute.

[0275] At the end of at least one reduction step (PR2), the reaction medium may be cooled to various temperatures between 15°C and 25°C, and then purged under an inert atmosphere such as nitrogen.

[0276] Next, the reaction medium obtained from step (PR2) is preferably filtered.

[0277] Preferably, the preparation method according to the present invention is ○ At least one reduction step (PR2) as defined above, Preferably, the reaction medium is subjected to at least one treatment with carbon black before, during, or after the reduction step (PR2), and more preferably, before or after the reduction step (PR2). □ At least one optional step of adding at least one acidifying agent or basicizing agent to the reaction medium obtained from the reduction step (PR2), 〇 At least one optional step (PR2) of concentrating the compound of formula (IB) in the reaction medium obtained from the reduction step (PR2), □ Preferably, at least one concentration step (PC) is carried out, specifically, preferably by distillation under reduced pressure. 〇 Optionally, at least one purification step such as filtration, 〇 At least one step of optionally adding at least one bactericide or bacteriostatic agent, preferably a bacteriostatic agent, preferably a bacteriostatic agent derived from glycol, for example, propylene glycol, pentylene glycol, or caprylyl glycol, more preferably propylene glycol. □ Preferably, the bacteriostatic agent (specifically propylene glycol) is present in a content ranging from 2% to 50% by mass, and more preferably in a content ranging from 5% to 40% by mass, relative to the total mass of the mixture containing at least one compound of formula (IB) and the bacteriostatic agent. □ Optionally, at least one purification process such as distillation. It contains a series of them.

[0278] Within the scope of the present invention, the term "biological" is understood to mean that propylene glycol is derived from a plant-derived compound.

[0279] Reaction process (PR3) The reaction step (PRii) is also the following synthesis route (B1): [ka] Accordingly, this may also be an addition or O-alkoxylation step (PR3) carried out in an aqueous or non-aqueous medium. During the synthesis pathway (B1), R is C1~C 10 This corresponds to an alkyl group, preferably a C1-C4 alkyl group, such as methyl, or a (C1-C4) alkylcarbonyl group, such as acetyl.

[0280] Advantageously, the method (PR) according to the present invention is, - At least one reaction step (PR1) as defined above, - At least one reaction step (PRii) corresponding to the reduction step (PR2) defined above, - At least one reaction step (PRiii) corresponding to the addition step (PR3) defined above, - At least one purification (PU) as defined above, performed between the reaction step (PR1) and the reduction step (P2), and / or at least after the reduction step (PR2), preferably between the reduction step (PR2) and the addition step (PR3), and / or after the addition step (PR3). Includes.

[0281] According to another alternative embodiment of the present invention, compound (I''B) is obtained by adding at least 1 molar equivalent of at least one nucleophilic compound RG (wherein R is as defined above, and G represents an electron-deficient atom or group such as an alkali metal, e.g., sodium, potassium, or lithium, or magnesium halide, e.g., MgCl) to (IA), specifically carrying out this reaction under an inert atmosphere and in a solvent (preferably a polar aprotic organic solvent, specifically an ether solvent, e.g., diethyl ether or THF), followed by a hydrolysis reaction.

[0282] An optional step for separating the excess compound of formula (III). Preferably, step (PR) may include at least one step of separating excess compound of formula (III) from the reaction medium obtained from step (PR1), specifically by distillation (e.g., vacuum distillation).

[0283] The step of separating the excess compound of formula (III) may be performed simultaneously with or sequentially to the neutralization step (PR0), preferably sequentially with the neutralization step (PR0), and preferably after the neutralization step (PR0).

[0284] According to one advantageous embodiment, process (PR) is: - At least one reaction step (PR1) as defined above, - At least one step (PR0) to neutralize the reaction medium obtained from step (PR1), - At least one step of separating excess compound of formula (III), which is performed simultaneously with or immediately following the neutralization step (PR0), preferably after the neutralization step (PR0). - At least one reduction step (PR2) as defined above, - At least one purification step (PU) as described above, preferably performed before and / or after the reduction step (PR2), more preferably before the reduction step (PR). It includes at least [this].

[0285] Packaging of the compound of formula (I) At the end of the method according to the present invention, the compound of formula (I) (wherein X corresponds to a divalent group -C(O)- or -CH(OR)-) can be packaged in the form of a dry extract (without solvent).

[0286] Preferably, at the end of the method according to the present invention, the compound of formula (I) (wherein X corresponds to a divalent group -C(O)- or -CH(OR)-) is a solution in a liquid containing at least 25% by mass of the active substance (cosmetic component, preferably the compound of formula (I)) relative to the total mass of the solution, and preferably in the range of 25% to 90% by mass.

[0287] Preferably, at the end of the method according to the present invention, the compound of formula (I) (wherein X corresponds to a divalent group -C(O)- or -CH(OR)-) is a solution in a liquid containing at least 20% by mass of the active substance relative to the total mass of the solution, and more preferably in the range of 20% to 90% by mass.

[0288] Preferably, at the end of the method according to the present invention, the compound of formula (I) (wherein X corresponds to a divalent group -C(O)- or -CH(OR)-) is a solution in a liquid containing at least 20% by mass of the active substance relative to the total mass of the solution, and more preferably in the range of 20% to 90% by mass.

[0289] According to one embodiment, a compound of formula (I) (wherein X corresponds to a divalent group -C(O)- or -CH(OR)-) is packaged in liquid, and the pH is adjusted to a target value by adding at least one basicizing agent or at least one acidifying agent, preferably to 3.5 to 7.

[0290] Method for preparing at least one compound of formula (I') Preferably, the method according to the present invention is a method for preparing (PR') one or more compounds of formula (I') as defined above.

[0291] The method according to the present invention preferably relates to the following formula (I'): [ka] It is at least one compound that corresponds to, In formula (I'), - n is equal to 0 or 1, preferably equal to 1. - p is a various integer from 1 to 4, preferably the subscript p is equal to 3. - R1 has the same meaning as in formula (I), and is preferably linear, preferably acyclic C1-C1. 10This represents an alkyl chain, preferably a C1-C6 alkyl chain, more preferably a C1-C4 alkyl chain, and specifically a C1 alkyl chain. - X represents a divalent group, -C(O)- or -CH(OR)-. - R is a hydrogen atom, C1~C 10 The R represents an alkyl group, preferably a C1-C4 alkyl group, such as methyl, or a (C1-C4) alkylcarbonyl group, such as acetyl, and preferably, R represents a hydrogen atom. compound and one of the optical or geometric isomers of this compound, and / or one of the solvates of this compound, such as the hydrate. A method for preparing (PR') the following: The aforementioned method, - The following synthesis scheme (A'): [ka] This is at least one reaction step (PR1) carried out according to the following: In synthesis pathway (A'), n is equal to 0 or 1, preferably equal to 1. 〇 p is a various integer from 1 to 4, preferably the subscript p is equal to 3. 〇 R1 and R2 are either the same or different, preferably the same, and R2 has the same meaning as R1 in formula (I'). 〇 D + is an organic or inorganic cation, preferably an inorganic cation, more preferably selected from the group consisting of alkali metal cations, alkaline earth metal cations, and ammonium cations (NH4+), and even more preferably selected from the group consisting of alkali metal cations and alkaline earth metal cations. The above reaction step (PR1) is carried out in an aqueous medium. ○ At least one compound of formula (II'), Preferably, at least one compound of formula (III) is present in equimolar amounts or in excess relative to the compound of formula (II'), □ Preferably, the compound of formula (III) is present in an amount greater than 1 molar equivalent relative to the compound of formula (II'), preferably in an amount in the range of 1 to 5 molar equivalents, and more preferably in an amount in the range of 1 to 4 molar equivalents. ○ Equimolar amount or excess, preferably excess, of at least one alkaline agent relative to the compound of formula (II'), □ Preferably, the alkaline agent is present in an amount ranging from 1 to 5 molar equivalents relative to the compound of formula (II'), and more preferably in an amount ranging from 1 to 4 molar equivalents. □ This alkaline agent is preferably an inorganic substance, more preferably selected from the group consisting of alkali metal hydroxides and alkaline earth metal hydroxides, alkali metal (bi)carbonates and alkaline earth metal (bi)carbonates, and mixtures thereof. Specifically, it is selected from the group consisting of alkali metal hydroxides and alkaline earth metal hydroxides, for example, sodium hydroxide. Reaction step (PR1) is carried out in the presence of to form at least one compound of formula (I'A1) and at least one compound of formula (IV1), - Preferably, at least one neutralization step (PR0), which includes acidification such as adding at least one inorganic or organic acidifying agent, preferably an organic acidifying agent, to the aqueous reaction medium obtained from step (PR1), - Selectively react at least the compound of formula (I'A1) to obtain formula (I'B1): [ka] This is at least one step (PRii) to obtain at least one compound corresponding to, In formula (I'B1), the subscripts n, p, and R1 have the same meaning as in formula (I). Preferably, the reaction step (PRii) is the reduction step (PR2) as defined above. Process (PRii), - At least one purification (PU) comprising at least one step (PU1) as defined above, of electrodialysis of at least one aqueous reaction medium comprising at least one compound of formula (I'A) or (I'B) and at least one compound of formula (IV1). This method includes [something].

[0292] The reaction step (PR1), reduction step (PR2), and purification step (PU), specifically the electrodialysis step (PU1), are as defined above.

[0293] Preferably, purification (PU) is performed after the reaction step (PR1), and more preferably, at least between the reaction step (PR1) and at least one reaction step (PRii), and / or at least after at least one reaction step (PRii), for example, after the reduction step (PR2).

[0294] Preferably, the reaction step (PRii) is the following synthesis route (B1): [ka] This is a reduction process (PR2) carried out in an aqueous medium according to the following: During the synthesis pathway (B1), - R1 has the same meaning as in equation (I).

[0295] Preferably, the reduction step (PR2) is reduction by catalytic hydrogenation as defined above.

[0296] Within the scope of the present invention, a compound of formula (I'A1) is a compound of formula (I') (wherein X corresponds to the divalent group -C(O)-).

[0297] Within the scope of the present invention, a compound of formula (I'B1) is a compound of formula (I') (wherein X corresponds to the divalent group -CH(OH)-).

[0298] Preferably, in reaction step (PR1), the molar ratio of compound (III) to compound (II') is 1 or greater, preferably 1 to 5, more preferably 1 to 4, more specifically 1 to 3, even better 1 to 2, specifically in the range of 1 to 1.5, and according to a particular embodiment, the molar ratio of compound (III) to compound (II') is greater than 1.

[0299] Preferably, the molar ratio of the alkaline agent / compound of formula (II'') is 1 or greater, preferably 1 to 5, more preferably 1 to 4, more specifically 1 to 3, and even better 1 to 2, and according to a particular embodiment, the molar ratio of the alkaline agent / compound of formula (II'') is greater than 1.

[0300] Method for preparing at least one compound of formula (I''') Preferably, the method according to the present invention is given by the following formula ('''): [ka] One or more compounds corresponding to the above, where X represents a divalent group -C(O)- or -(CH)OR-, and R represents a hydrogen atom. compound and one of the optical or geometric isomers of this compound, and / or one of the solvates of this compound, such as the hydrate. A method for preparing (PR'') the following: The aforementioned method, - The following synthesis scheme (A''): [ka] This is at least one reaction step (PR1) carried out according to the following: During synthesis pathway (A''), 〇 D + These include alkali metal cations, alkaline earth metal cations, and ammonium ions (NH4 + A cation selected from the group consisting of ), The above reaction step (PR1) is carried out in an aqueous medium. 〇 Preferably present in equimolar amounts or in excess relative to the compound of formula (II''), and preferably in excess, at least one compound of formula (III'), □ Preferably, the compound of formula (III') is present in an amount greater than 1 molar equivalent relative to the compound of formula (II''), preferably in an amount in the range of 1 to 5 molar equivalents, and more preferably in an amount in the range of 1 to 4 molar equivalents. ○ Equimolar amount or excess, preferably excess, of at least one alkaline agent relative to the compound of formula (II''), □ Preferably, the alkaline agent is present in an amount ranging from 1 to 5 molar equivalents relative to the compound of formula (II''), and more preferably in an amount ranging from 1 to 4 molar equivalents. □ This alkaline agent is preferably an inorganic substance, more preferably selected from the group consisting of alkali metal hydroxides and alkaline earth metal hydroxides, and more specifically selected from alkali metal hydroxides, such as sodium hydroxide. Reaction step (PR1) is carried out in the presence of to form at least one compound of formula (I'''A) and at least one compound of formula (IV2), - Preferably, at least one neutralization step (PR0), which includes at least one acidification step (PR0), such as adding at least one inorganic or organic acidifying agent, preferably an organic acidifying agent, to the aqueous reaction medium obtained from step (PR1), - Selectively react at least the compound of formula (I'''A) to produce the following formula (I'''B): [ka] This is at least one step (PRii) to obtain at least one compound corresponding to, Preferably, the reaction step (PRii) is the reduction step (PR2) as defined above. Process (PRii), - At least one purification (PU) comprising at least one step (PU1) as defined above, of electrodialysis of at least one aqueous reaction medium comprising at least one compound of formula (I''A) or (I''B) and at least one compound of formula (IV2). This method includes [something].

[0301] The reaction step (PR1) and the purification step (PU) are as defined above.

[0302] Preferably, purification (PU) is performed at least between reaction step (PR1) and at least one reaction step (PRii), and / or at least after at least one reaction step (PRii), for example, after reduction step (PR2).

[0303] Preferably, the purification step PU1 is performed after the reaction step (PR1) and before the reaction step (PRii).

[0304] Within the scope of the present invention, a compound of formula (I'''A) is a compound of formula (I''') (wherein X corresponds to the divalent group -C(O)-).

[0305] Within the scope of the present invention, a compound of formula (I'''B) is a compound of formula (I''') (wherein X corresponds to a -CH(OH) group).

[0306] Preferably, the molar ratio of compound (III) to compound (II'') is 1 or greater, preferably 1 to 5, more preferably 1 to 4, more specifically 1 to 3, even better 1 to 2, specifically in the range of 1 to 1.5, and according to a particular embodiment, the molar ratio of compound (III) to compound (II') is greater than 1.

[0307] Preferably, the molar ratio of the alkaline agent / compound of formula (II'') is 1 or greater, preferably 1 to 5, more preferably 1 to 4, more specifically 1 to 3, and even better 1 to 2, and according to a particular embodiment, the molar ratio of the alkaline agent / compound of formula (II'') is greater than 1.

[0308] Preferably, reaction step (PRii) is the following synthesis route (B''): [ka] This is a reduction step (PR2) carried out in an aqueous medium according to the following.

[0309] Preferably, the reduction step (PR2) is reduction by catalytic hydrogenation as defined above.

[0310] Preferably, purification (PU) is performed at least between the reaction step (PR1) and the reduction step (PR2).

[0311] A method for preparing at least one compound of formula (I') or (I'') may also include additional steps described with respect to a method for preparing at least one compound of formula (I).

[0312] The present invention will be described in more detail by the following non-limiting embodiments. [Examples]

[0313] Example 1: Preparation of -C-β-D-xylopyranoside-2-hydroxypropan-2-one (35% by mass) Step 1: Preparation of the compound of formula (I''') [ka]

[0314] Step 1: Lubineau reaction and purification by electrodialysis. Add water (1.04 kg) to the reactor at 20°C. Heat to 50°C, then add xylose (700 g) and stir until the medium is homogenized. Cool the mixture to 15°C and add acetylacetone (555 g). Add 50% sodium hydroxide solution (540 g) at a temperature below 45°C. Then heat the mixture from 30°C to 50°C for 30 minutes to 4 hours. Cool the mixture to 20°C and then acidify it to a pH of less than 6. Concentrate the medium to 30% to 60%.

[0315] Next, an electrodialysis pass is performed at a pH of 4.0 to 8.0 and a temperature of 25°C to 45°C until the acetic acid content is reduced to less than 10,000 ppm, and further to 6,000 ppm or less.

[0316] Next, this solution is brought into contact with carbon black, then optionally concentrated to a solid content of 30%–60%, and then the pH is adjusted to 6.0–7.0. The product is isolated in 90–95% yield.

[0317] Step 2: Hydrogenation [ka] A compound of formula (I') (2.08 kg) in an aqueous solution with an appropriate acetic acid content is introduced into a hydrogenation apparatus containing ruthenium on carbon (catalyst). This mixture is purged at least once with nitrogen, and then purged with hydrogen. This mixture may be heated to a temperature above 25°C, and then hydrogen is introduced under a maximum pressure of approximately 10 bar.

[0318] This mixture is heated to a temperature of 100°C or less under a pressure ranging from 8 to 12 bar for a period ranging from 2 to 7 hours. This hydrogenation reaction is carried out until the consumption of hydrogen is complete.

[0319] The reaction medium may be allowed to return to ambient temperature (20°C), and then optionally purged with an inert gas (nitrogen). The catalyst is then filtered, and the filtrate is optionally brought into contact with carbon black. This solution is concentrated until a solid content of 40% to 80% is obtained.

[0320] The pH of this filtrate is adjusted to an acidic pH (e.g., 4-6). To obtain a compound content of formula (I) of 20% to 90%, a glycol derivative such as propylene glycol may be added to the above solution as a solvent.

[0321] The product is isolated in solution with good yield (90-95%) and an acetic acid content of less than 20,000 ppm in the solution.

Claims

1. A method for purifying (PU) at least one aqueous medium, wherein the aqueous medium is - The following equation (I) 【Chemistry 1】 It is a compound of, In formula (I), - SA' represents a monosaccharide or polysaccharide group containing up to 20 sugar units of the pyranose and / or furanose type, and of the L and / or D series, specifically a monosaccharide or polysaccharide group containing up to 6 sugar units, wherein the monosaccharide or polysaccharide group has at least one free hydroxyl group and optionally at least one optionally protected amine group. - SA' and CH ２ The bond between -X and is a C-anomeric bond. - X represents a divalent group -C(O)- or -CH(OR)-, preferably -C(O)- or -CH(OH)-, - R is a hydrogen atom, C １ ~C １０ Alkyl alkyl group, preferably C １ ~C ４ Alkyl alkyl groups, for example, methyl, or (C １ ~C ４ ) Represents an alkylcarbonyl group, for example acetyl, preferably representing a hydrogen atom. -R １ R represents a saturated or unsaturated, linear or branched, cyclic or acyclic, preferably acyclic C １ to C １０ hydrocarbon chain, preferably a more preferentially saturated C １ to C ４ hydrocarbon chain, and specifically, R １ represents a linear or branched, saturated or unsaturated, cyclic or acyclic C １ to C １０ hydrocarbon chain, more specifically a C １ to C ６ hydrocarbon chain, even more preferentially a C １ to C ４ hydrocarbon chain, for example a C １ hydrocarbon chain. compound, - and one of the optical or geometric isomers of this compound, and / or one of the solvates of this compound, such as the hydrate. At least one cosmetic ingredient selected from, - At least one type of salt and Includes, The method comprises at least one step (PU1) of electrodialysis of the aqueous medium.

2. SA' represents a monosaccharide group selected from the group consisting of glucose, especially D-glucose, xylose, especially D-xylose, fucose, especially L-fucose, arabinose, especially L-arabinose, rhamnose, especially L-rhamnose, glucuronic acid, especially D-glucuronic acid, galacturonic acid, especially D-galacturonic acid, iduronic acid, especially D-iduronic acid, N-acetylglucosamine, especially N-acetyl-D-glucosamine, N-acetylgalactosamine, especially N-acetyl-D-galactosamine, and the method according to claim 1, wherein SA is preferably selected from D-glucose, D-xylose, L-fucose, L-arabinose, L-rhamnose, D-glucuronic acid, D-galacturonic acid, and D-iduronic acid.

3. R １ C is a linear, saturated or unsaturated, acyclic C １ ~C ６ Hydrocarbon chains, more preferably C １ ~C ４ Hydrocarbon chains, specifically C １ The method according to claim 1 or 2, characterized in that it represents a hydrocarbon chain.

4. The method according to any one of claims 1 to 3, characterized in that X represents a divalent group -C(O)- or -CH(OH)-.

5. The aforementioned cosmetic agent is given by formula (I''): 【Chemistry 2】 A compound of, In formula (I''), R １ And X represents a compound as defined in any one of claims 1, 3, or 4, as well as one of the optical or geometric isomers of the compound and / or one of the solvates of the compound, such as a hydrate. Preferably, formula (I'''): 【Transformation 3】 A compound of, In the formula (I'''), X corresponds to a divalent group, -C(O)- or -(CH)OH-, and preferably corresponds to -C(O)-, in the compound. This also represents one of the optical or geometric isomers of this compound, and / or one of the solvates of this compound, such as the hydrate. The method according to any one of claims 1 to 4, characterized in that

6. The method according to any one of claims 1 to 5, characterized in that the cosmetic component is present in an amount of at least 25% by mass of the active component of the cosmetic component with respect to the total mass of the aqueous medium, preferably in an amount in the range of 25% to 80% by mass, more preferably in an amount in the range of 25% to 75% by mass, and more preferably in an amount in the range of 30% to 70%.

7. The aforementioned salt is given by the following formula (IV) D ｙ＋ A ｗ－ (96) It supports, In formula (IV), y is an integer in the range of 1 to 3, preferably 1. w is an integer in the range of 1 to 3, preferably 1. A is an organic or inorganic anion, preferably an organic anion, and more preferably C １ ~C １８ Selected from the group composed of carboxylic acids, and more preferably C １ ~C １０ Selected from the group composed of carboxylic acids, and even better, C １ ~C ６ Selected from the group composed of carboxylic acids, D is an organic or inorganic cation, preferably an inorganic cation, more preferably an alkali metal cation, an alkaline earth metal cation, and an ammonium cation (NH ４ ＋ Selected from the group consisting of ) The method according to any one of claims 1 to 6, characterized in that

8. The aforementioned salt is given by the following formula (IV1): 【Chemistry 4】 It supports, In formula (IV1), D is an organic or inorganic cation, preferably an inorganic cation. R ２ This is saturated or unsaturated, linear or branched, cyclic or acyclic, preferably acyclic C. １ ~C １０ Hydrocarbon chains, preferably C １ ~C ６ Hydrocarbon chains, more preferably C １ ~C ４ Hydrocarbon chains, specifically C １ This represents a hydrocarbon chain. The method according to any one of claims 1 to 7, characterized in that

9. The method according to any one of claims 1 to 8, characterized in that the salt is present in an amount ranging from 0.05% to 50% by mass with respect to the total mass of the aqueous medium, more specifically in an amount ranging from 0.1% to 40% by mass, and more specifically in an amount ranging from 0.5% to 30% by mass.

10. The method according to any one of claims 1 to 9, characterized in that the electrodialysis process (PU1) is carried out at a pH of 4 to 9, and more preferably at a pH of 4.5 to 8.

5.

11. The method according to any one of claims 1 to 10, characterized in that the electrodialysis process (PU1) is carried out at a temperature in the range of 20°C to 50°C, preferably in the range of 25°C to 45°C.

12. The method according to any one of claims 1 to 11, characterized in that the electrodialysis step (PU1) is carried out in conjunction with conventional electrolysis, preferably specifically at a temperature in the range of 20°C to 50°C, with a pre-treatment product conductivity in the range of 50 to 0.05 mS / cm, more preferably in the range of 40 to 0.2 mS / cm.

13. The method according to any one of claims 1 to 12, characterized in that the electrolytic antibody (PU1) is carried out together with bipolar membrane electrolysis at a pre-treatment product conductivity in the range of 60 to 0.5 mS / cm, preferably in the range of 55 to 1 mS / cm, more preferably in the range of 50 to 10 mS / cm, and even more preferably in the range of 45 to 20 mS / cm, measured at a temperature in the range of 20°C to 50°C.

14. The method according to any one of claims 1 to 13, characterized in that, at the end of the electrodialysis process (PU1), the salt content is 10% by mass or less, preferably 5% by mass or less, more preferably within a range of 1% by mass to 5% by mass, and even more preferably within a range of 1% by mass to 2% by mass, based on the total mass of the dry extract containing the cosmetic component.

15. A method (PR) for preparing at least one compound of formula (I) as defined in any one of claims 1 to 5, - The following synthesis scheme (A): 【Transformation 5】 This is at least one reaction step (PR1) carried out according to the following: During synthesis route (A), 〇 R １ and R ２ They are either the same or different; R ２ R in equation (I) １ It has the same meaning as, 〇 SA' has the same meaning as in formula (I), 〇 D ＋ is an organic or inorganic cation, preferably an inorganic cation. The above reaction step (PR1) is carried out in an aqueous medium. ○ At least one compound of formula (II), ○ At least one compound of formula (III), and ○ At least one alkaline agent in an equimolar amount or in excess relative to the compound of formula (II) Execute in the presence of, Reaction step (PR1) brings about the formation of at least one compound of formula (IA) and at least one compound of formula (IV1) in an aqueous medium. - Optionally, at least one neutralization step (PR0) comprising adding at least one inorganic or organic acidifying agent to the aqueous reaction medium obtained from step (PR1), preferably an organic acidifying agent. - Selectively reacting at least one compound of formula (IA) to obtain the following compound (IB): 【Transformation 6】 The least one step (PRIi) is to form at least one compound corresponding to, In formula (IB), - SA, R １ , and R have the same meaning as in formula (I), process (PRIi), - At least one purification (PU) of at least one aqueous medium comprising at least one compound of formula (IA) or (IB) and at least one compound of formula (IV1), comprising at least one electrodialysis step (PI1) as defined in any one of claims 1 or 10 to 13. A method characterized by including the following.

16. The method according to any one of claims 1 to 15, characterized in that the purification (PU) is performed at least after the neutralization step (PR0).

17. The reaction step (PRIi) is the following synthesis route (B): 【Transformation 7】 This is a reduction process (PR2) carried out in an aqueous medium according to the following: During synthesis route (B), - SA', and R １ This has the same meaning as in equation (I), The method according to claim 15 or 16.

18. The method according to claim 15 or 17, wherein the reduction step (PR2) is reduction by catalytic hydrogenation, preferably reduction by catalytic hydrogenation using a metal catalyst, for example, ruthenium (Ru), rhodium (Rh), platinum (Pt), iridium (Ir), nickel (Ni), or palladium (Pd), preferably reduction by catalytic hydrogenation using ruthenium (Ru), more preferably reduction by catalytic hydrogenation using a metal catalyst selected from ruthenium (Ru), rhodium (Rh), platinum (Pt), or iridium (Ir), and even better, reduction by catalytic hydrogenation using ruthenium (Ru).

19. The method according to any one of claims 15 to 18, characterized in that the purification (PU) is performed after the reaction step (PR1), or between the reaction step (PR1) and the reaction step (PRIi), or after the reaction step (PRIi), preferably between the reaction step (PR1) and the reaction step (PRIi).

20. The method according to any one of claims 15 to 19, characterized in that the alkalizing agent in the (PR0) step is an inorganic alkaline agent selected from the group consisting of alkali metal or alkaline earth metal hydroxides, alkali metal or alkaline earth metal (bi)carbonates, and mixtures thereof, and more specifically is an alkali metal or alkaline earth metal hydroxide, and more specifically is sodium hydroxide.

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