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EP-4739665-A1 - PURIFICATION PROCESS COMPRISING ONE OR MORE COSMETIC INGREDIENTS WITH AT LEAST ONE ELECTRODIALYSIS

EP4739665A1EP 4739665 A1EP4739665 A1EP 4739665A1EP-4739665-A1

Abstract

The present invention relates to a process for the purification (PU) of at least one aqueous medium based on at least one C-glycoside derivative corresponding to the formula (I), preferably corresponding to the formula (I') or (I''), and the optical isomers or geometrical isomers thereof, and/or the solvates thereof, such as the hydrates, and at least one salt, comprising at least one step of electrodialysis (PU1) of said aqueous medium. The invention also relates to a process for the preparation (PR) of at least one C-glycoside derivative, as described herein, comprising at least one step of purification (PU) by electrodialysis of at least one aqueous medium comprising at least said C- glycoside derivative and at least one salt.

Inventors

  • WAFFLART, Florence
  • KOSTELITZ, Olivier
  • PARLY, Florence

Assignees

  • L'OREAL

Dates

Publication Date
20260513
Application Date
20240703

Claims (20)

  1. 1. Process for purification (PU) of at least one aqueous medium comprising: at least one cosmetic ingredient chosen from the compounds of formula (I) below: in which formula (I): - SA' represents a monosaccharide group or a polysaccharide group comprising up to 20 sugar units, in particular up to 6 sugar units, in pyranose and/or furanose form and of the L and/or D series, said monosaccharide group or polysaccharide group having at least one free hydroxyl group, and optionally at least one optionally protected amine group, - the bond between SA' and CH2-X is a bond of C-anomeric nature, - X represents a divalent radical -C(O)- or -CH(OR)-, preferably -C(O)- or - CH(OH)-; - R represents a hydrogen atom, a C1-C10, preferably C1-C4, alkyl group, such as methyl, or a (Ci-C4)alkylcarbonyl group, such as acetyl, preferably a hydrogen atom, - Ri represents a saturated or unsaturated, linear or branched, cyclic or acyclic, preferably acyclic, C1-C10, preferably C1-C4 hydrocarbon chain, which is more preferentially saturated; particularly Ri represents a linear or branched, saturated or unsaturated, cyclic or acyclic, C1-C10, more particularly Ci-Ce, even more preferentially C1-C4, such as Ci hydrocarbon chain, - and also one of the optical isomers or geometrical isomers thereof, and/or one of the solvates thereof, such as the hydrates, and - at least one salt; said process comprising at least one step of electrodialysis (PU1) of said aqueous medium.
  2. 2. Process according to the preceding claim, characterized in that SA' represents a monosaccharide group chosen from the group constituted of glucose, notably D-glucose, xylose, notably D-xylose, fucose, notably L-fucose, arabinose, notably L-arabinose, rhamnose, notably L-rhamnose, glucuronic acid, notably D- glucuronic acid, galacturonic acid, notably D-galacturonic acid, iduronic acid, notably D-iduronic acid, N-acetylglucosamine, notably N-acetyl-D-glucosamine, N- acetylgalactosamine, notably N-acetyl-D-galactosamine and preferably SA is chosen from D-glucose, D-xylose, L-fucose, L-arabinose, L-rhamnose, D-glucuronic acid, D- galacturonic acid, D-iduronic acid.
  3. 3. Process according to Claim 1 or 2, characterized in that Ri represents a linear, saturated or unsaturated, acyclic Ci-Ce, more preferentially C1-C4, in particular Ci hydrocarbon chain.
  4. 4. Process according to any one of Claims 1 to 3, characterized in that X represents a divalent radical -C(O)- or -CH(OH)-.
  5. 5. Process according to any one of Claims 1 to 4, characterized in that the cosmetic agent(s) represent a compound of formula (I”): (I”) in which formula (I”) Ri and X are as defined in any one of Claims 1, 3 or 4, and also one of the optical isomers or geometrical isomers thereof, and/or one of the solvates thereof, such as the hydrates; and preferably of formula (I’”): in which formula (I’”): X corresponds to a divalent radical -C(O)- or -(CH)OH-, preferably -C(O)-, and also one of the optical isomers or geometrical isomers thereof, and/or one of the solvates thereof, such as the hydrates.
  6. 6. Process according to any one of the preceding claims, characterized in that the cosmetic ingredient(s) is (are) present in a content of at least 25% by weight of active ingredient of cosmetic ingredient(s), preferentially in a content ranging from 25% to 80% by weight, more preferentially ranging from 25% to 75% by weight, more preferentially ranging from 30% to 70% relative to the total weight of the aqueous medium.
  7. 7. Process according to any one of the preceding claims, characterized in that said salt corresponds to formula (IV) below: in which formula (IV): y is an integer ranging from 1 to 3, preferably 1; w is an integer ranging from 1 to 3, preferably 1; A is an organic or inorganic anion, preferably an organic anion, more preferentially chosen from the group constituted of Ci-Cis, even more preferentially Ci-Cio, better still Ci-Ce carboxylic acids; D is an organic or inorganic cation, preferably an inorganic cation, more preferentially chosen from the group constituted of alkali metal cations, alkaline earth metal cations and ammonium cations (NHV).
  8. 8. Process according to the preceding claim, characterized in that said salt corresponds to formula (IV1) below: in which formula (IV1): D is an organic or inorganic cation, preferably an inorganic cation, R2 represents a saturated or unsaturated, linear or branched, cyclic or acyclic, preferably acyclic, Ci-Cio, preferably Ci-Ce, more preferentially C1-C4, in particular Ci, hydrocarbon chain.
  9. 9. Process according to one of the preceding claims, characterized in that the salt is present in a content ranging from 0.05% to 50% by weight, in particular in a content ranging from 0.1% to 40% by weight, more particularly in a content ranging from 0.5% to 30% by weight, relative to the total weight of the aqueous medium.
  10. 10. Process according to any one of the preceding claims, characterized in that the electrodialysis step (PU1) is carried out at a pH of between 4 and 9, more preferentially between 4.5 and 8.5.
  11. 11. Process according to any one of the preceding claims, characterized in that the electrodialysis step (PU1) is carried out at a temperature ranging from 20°C to 50°C, preferably at a temperature ranging from 25°C to 45°C.
  12. 12. Process according to any one of the preceding claims, characterized in that the electrodialysis step (PU1) is carried out with conventional electrolysis, preferentially at a product conductivity, before treatment, ranging from 50 to 0.05 mS/cm, preferably ranging from 40 to 0.2 mS/cm, measured in particular at a temperature ranging from 20°C to 50°C.
  13. 13. Process according to any one of the preceding claims, characterized in that the electrodialysis step (PU1) is carried out with bipolar membrane electrolysis with a product conductivity (before treatment) ranging from 60 to 0.5 mS/cm, preferably ranging from 55 to 1 mS/cm, more preferentially ranging from 50 to 10 mS/cm, even more preferentially ranging from 45 to 20 mS/cm, measured in particular at a temperature ranging from 20°C to 50°C.
  14. 14. Process according to any one of the preceding claims, characterized in that, on conclusion of the electrodialysis step (PU1), the salt content is less than or equal to 10% by weight, preferably is less than or equal to 5% by weight, more preferentially varies from 1% to 5% by weight, better still varies from 1% to 2% by weight, relative to the total weight of the dry extract containing the cosmetic ingredient.
  15. 15. Process for preparing (PR) at least one compound of formula (I), as defined in any one of Claims 1 to 5, characterized in that it comprises: - at least one reaction step (PR1) taking place according to the following synthesis (it) i) (iA) (wi) in which synthetic pathway (A): o Ri and R2 are identical or different; with R2 having the same meaning as Ri in the formula (I), o SA' has the same meaning as in the formula (I), o D + is an organic or inorganic cation, preferably an inorganic cation, said reaction step (PR1) being carried out in an aqueous medium in the presence: o of at least one compound of formula (II), o of at least one compound of formula (III), and o of at least one alkaline agent in an equimolar amount or in excess relative to the compound of formula (II), to result in the formation of at least one compound of formula (IA) and of at least one compound of formula (IV1) in an aqueous medium, - optionally at least one neutralisation step (PRO) comprising the addition of at least one inorganic or organic acidifying agent, preferably organic acidifying agent, to the aqueous reaction medium obtained from said step (PR1), - optionally, at least one step (PRii) of reacting at least said compound of formula (IA) to result in the formation of at least one compound corresponding to the following formula (IB): (IB) in which formula (IB): - SA, Ri and R have the same meanings as in the formula (I), - at least one purification (PU) comprising at least one electrodialysis step (PU1), as defined according to any one of Claims 1 or 10 to 13, of at least one aqueous reaction medium comprising at least one compound of formula (IA) or (IB) and at least one compound of formula (IV1).
  16. 16. Process according to the preceding claim, characterized in that the purification (PU) is carried out after at least the neutralization step (PRO).
  17. 17. Process according to Claim 15 or 16, characterized in that the reaction step (PRii) is a reduction step (PR2) taking place in an aqueous medium according to the following synthetic pathway (B): (IA) (FB) in which synthetic pathway (B): - SA' and Ri have the same meanings as in the formula (I).
  18. 18. Process according to Claim 15 or 17, characterized in that the reduction step (PR2) is a reduction by catalytic hydrogenation, preferably with a metal catalyst, such as ruthenium (Ru), rhodium (Rh), platinum (Pt), iridium (Ir), nickel (Ni) or palladium (Pd), preferably ruthenium (Ru) more preferentially a metal catalyst chosen from ruthenium (Ru), rhodium (Rh), platinum (Pt), Iridium (Ir), and better still ruthenium (Ru).
  19. 19. Process according to any one of Claims 15 to 18, characterized in that the purification (PU) is carried out 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. 20. Process according to any one of Claims 15 to 19, characterized in that the alkaline agent(s) of the (PRO) step is or are inorganic alkaline agents chosen from the group constituted of alkali metal or alkaline earth metal hydroxides, alkali metal or alkaline earth metal (bi)carbonates, and mixtures thereof, in particular alkali metal or alkaline earth metal hydroxides, in particular sodium hydroxide.

Description

DESCRIPTION TITLE: Purification process comprising one or more cosmetic ingredients with at least one electrodialysis The present invention relates to a process for the purification (PU) of at least one aqueous medium based on at least one cosmetic ingredient, notably at least one C- glycoside derivative corresponding to the formula (I), as described below, preferably corresponding to the formula (I’) or (I”), and to the optical isomers or geometrical isomers thereof, and/or the solvates thereof, such as the hydrates, and at least one salt, comprising at least one step of electrodialysis (PU1) of said aqueous medium. The invention also relates to a process for the preparation (PR) of at least one cosmetic ingredient, notably at least one C-glycoside derivative, as described below, comprising at least one step of purification (PU) by electrodialysis of at least one aqueous medium comprising at least said cosmetic ingredient and notably at least one C-glycoside derivative and at least one salt. Processes for the preparation of water-soluble organic ingredients having advantageous cosmetic properties, for example on keratin materials, may lead to the formation of one or more impurities, in an ionic form, which generally prove to be tedious to minimize, or even to remove, without impacting to a greater or lesser extent the yield of the cosmetic ingredient synthesized. Moreover, such impurities, when they are present with the final cosmetic ingredient, can generate a colour, a modification in texture or an odour which is not desired in the cosmetic compositions employing said ingredient. Thus, such impurities can be the source of an unpleasant and marked odour, for example a pungent and strongly vinegary odour, liable to manifest itself, even after one or more purification operations have been carried out, and to prove to be inconvenient and persistent even after formulation for consumers, all the more so since the current trend is to use fewer and fewer fragrances in cosmetic products to mask or neutralize odours of this type. Such impurities can also give rise to problems of compatibility with other additives optionally present in the final cosmetic formulations. Such impurities can also be salts of acids or of bases which will have an effect on the pH in an aqueous medium. This effect is all the more of a nuisance as the cosmetic active agent is isolated in the form of a concentrated aqueous solution. In addition, the presence of such impurities, in particular of inorganic and/or organic salts, can induce a considerable increase in the viscosity of the aqueous reaction medium comprising the cosmetic ingredient(s), thus making it difficult, in certain cases, to obtain concentrated solutions of cosmetic ingredients intended for the formulation. By way of example, C-glycoside derivatives are water-soluble organic compounds, the properties of which are generally advantageous in the field of cosmetics, in particular in care compositions, in order to be used to stimulate the synthesis of glycosaminoglycans present in the dermis and in particular to provide density and firmness to the skin (see, for example, the scientific paper entitled “Synthesis of Pro-Xylane™: A new biologically active C-glycoside in aqueous media”, M. Dalko-Csiba el al.. Bioorganic & Medicinal Chemistry Letters, 19 (2009), 845-849). C-glycoside derivatives, such as xylose C-glycoside derivatives, are generally synthesized by means of a reaction, known as the Lubineau reaction (Rodrigues, F., Canac, Y. and Lubineau, A., A convenient, one-step, synthesis of P-C-glycosidic ketones in aqueous media, Chemical Communications, 2000 (20), 2049-2050), from a monosaccharide or a polysaccharide which is unprotected, for example D-xylose, and a P-dicarbonyl compound, for example acetyl acetone, in an aqueous medium in the presence of alkaline agent(s). The Lubineau reaction is carried out with 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, for a reaction time capable of varying from 5 minutes to 20 hours depending on the nature of the alkaline agent and/or on the reaction parameters, such as the concentration and/or the temperature. However, such a synthesis reaction exhibits in particular the major pitfail of resulting in the formation of impurities, which are in particular in the form of salts, for example in the form of an organic salt, such as sodium acetate, the residual amounts of which can prove to be significant and difficult to reduce, even by carrying out several conventional purification and/or washing operations. On conclusion of this reaction, the aqueous reaction medium can be neutralized with at least one mineral acidifying agent, notably hydrochloric acid, in order to convert the organic acid salt into an organic acid, in particular by converting sodium acetate into acetic acid, then several